My name is, or maybe we better make that was, Andy Moore. Recently I had my personal identification changed to Jamie Jo Moore and everyone I know now calls me Sissy.
My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,000.00 and an eighteen percent interest in an insurance company in Nashville, TN. I spent my college years in Nashville and liked the town so I moved there as soon as the estate was settled. I bought an elegant existing home in the Belle Meade area and accepted a do-nothing job with the insurance company.
My sex life was pitiful. At six-feet tall and 168 pounds on a slender frame I was no Adonis. I had long blond hair, green eyes and a pale complexion. I didn’t participate in outside activities, like golf or tennis, gravitating instead to upscale bars, indoor sporting events and invitation-only parties.
For millions of reasons some girls were attracted to me, but I was shy and self-conscious around women. I ran with a group of guys that liked to drink and party, but none of them were real lady-killers either.
My friend Luke and I were at the Tennessee Bar late one evening when a short blond beauty came drifting in. She was with two other gals, also knockouts. They drank, played the shuffleboard and danced together to some Latin jukebox music.
An hour or so after they arrived the blond walked over to where I was seated. She wore a sheer pale blue blouse leaving her navy-blue camisole clearly visible. Her nipples were prominent. Her breasts shimmied as she walked.
Standing very close to me she asked, “Do you dance?”
“No, Ma’am.” I stammered out. Her face was thin, Scandinavian. Her eyes were as blue as a summer sky. She wore little makeup, but her full lips were a delicious wet red.
She leaned over and whispered in my ear. “Do I look old enough to be your mommy?”
I was staring down her blouse at her beautiful bare breasts and it occurred to me that there would be some advantages to being her baby.
“No.” I said and almost added ma’am again, but I caught myself. “I mean I don’t dance to this kind of music.”
She smiled and leaned over to whisper in my ear again. “Do you fuck?”
I turned bright red and looked down. She turned and I watched her walk back to her seat. A navy blue, knee-length skirt corralled two fluid orbs. Her legs were full, smooth and bare. She had a classic, voluptuous body and a swing to her hips that would stop traffic in Times Square. When she reached her table, she said something to her friends and they all laughed. My friend Luke asked me what she said. I tried to blow it off, but he kept on and on so I finally told him.
“Damn, son. If I were you I’d take another look at that dame, get over there and tell her yes.”
Easy for him to say, I thought. I hated aggressive women, but Luke just wouldn’t let it go so I finally agreed to send her a bottle of champagne and see what happened.
I watched as my beautiful blond poured two glasses. Her stiletto heels assaulted the dance floor as she walked over to where I was sitting and offered me one of the glasses. Although she spoke in a normal tone, it seemed to me she used a bullhorn. “Here’s to fucking.”
I was sitting there holding my glass like a bump on a stump. She clinked her glass on mine and sipped the bubble wine. I might have been mistaken for a statue.
A broad smile revealed beautiful teeth. She waved her hand in front of my face and said. “Hello, anybody home?”
I snapped out of my trance, downed my drink and said. “Cheers.”
She sat her glass on the bar and extended her hand. “I’m Sheila. Sheila Taylor.”
“Hi, Sheila. I’m Andy Moore. Pleased to make you, I mean meet you.” I’d almost gotten a complete sentence out without making an ass out of myself.
She flashed another lovely smile and said. “Andy, that’s some line.”
I laughed, still in the grip of her delicate hand. “Let me buy your dinner and I’ll promise to come up with something better.” I said.
“I’ve eaten.” She said and handed me a card. “Call my cell tomorrow and we’ll see.”
Her card said she was the president of Cumberland Investments.
Our courtship lasted only ninety days. I learned she had an MBA and had parlayed a six-figure income with one of the Wall Street firms into a brokerage company of her own. She and her parents didn’t speak and mine were dead so we weren’t likely to have any in-law problems. She was adamant that she wanted no children, but she was a sexual machine with a voracious appetite. I, on the other hand, had limited sexual experience. My first time was with a neighborhood girl when I was fourteen. She was seventeen. We gyrated around with her on top and I ejaculated. What a thrill. My second experience was with a gay friend in college. I didn’t tell Sheila about the later experience, but it was obvious I was sexually inexperienced.
We were married in a civil service and honeymooned in Hawaii for a month. We returned home and settled into a comfortable routine. An outside observer might have called it normal and but, for those occasions when I dressed up in women’s clothes, it might have been.
I’ve been “dressing-up” since childhood and I never told Sheila. Like most transvestites, sneaking around to dress just added to the excitement. I shopped the Internet for hours before selecting the perfect items and had them shipped to my secret post office box. There was a small hidden room off the garage I had converted into a closet and dressing room.
This normal life was to change completely one afternoon about ten months after we married. I arrived home after work, threw my keys on a table in the foyer and walked into the den. It was a beautiful; richly appointed room with dark paneling, honey oak flooring and Turkish rugs. Sheila was lying naked on the floor. I recognized the woman next to her to be her former college roommate Jenny Renee Wilson. They were locked in a sixty-nine position, lapping away at each other’s pussies. I stood transfixed, both shocked and intrigued. After a few moments, Jenny looked up and said, “Get the fuck out of here.” Then she returned to work on Sheila cunt.
To this moment I’m not sure why I didn’t jerk her up and kick her skinny little ass. It wasn’t really about Jenny. It was about Sheila. I realized I was afraid to rile her and something deep inside me caved in. A newfound subservience guided my steps as I turned and left the house.
I drove to a small bar down the street and drank a couple of beers. An hour or so later it dawned on me it was the first of April, April fool’s day. I called home and Sheila answered the phone.
“Hello.” She said in a cheerful tone.
“April fools, right?” I said.
“Come home immediately.” She said.
As I traveled home, my April fool supposition gave way to a feeling of impending doom. My hand rattled the front door knob as I entered the house.
The sight as I entered our den was almost as shocking this time as it had been a few hours earlier. As before, I found them in the den. Sheila sat atop a barstool. Her soft shoulders and ample 36C breasts fell gracefully to a 22″ waist and 38″ hips. She was dressed in a white on white brocade corset. It was a straight-line design without cups, so it flattened her breasts against her chest and caused them billowed over its top. She wore no panties and sometime since I’d seen her last, her pussy had been shaved. Smooth and fat it protruded from her pubic bone like a flesh-colored peach. Her white stockings were attached to the corset with three garters to a side. She wore white single-banded sandals with 4″ spike heels. Her nails flashed red.
Jenny stood beside her, 5′ 7″ tall and very slender. Her short platinum blonde hair and the ringlets across her forehead gave her a severe 1920’s look. She wore a black leather waist cincher. Her bare B-cup breasts sat firmly on her smooth chest. Each long, thick nipple sported a silver barbell. Black leather garters supported her black fishnet hose. Her polished black, high-heel boots were laced up to just below her knees.
Haltingly, I stopped and faced them.
Sheila’s tone was businesslike. “You may strip, kneel and await our orders or you may pack and leave forever.”
The scene was surreal. I rubbed my chin, looked at Jenny and then at Sheila “Why are you doing this, darling?”
Sheila slid down from her stool, slowly sat her drink down and deliberately walked over to face me. She slapped me hard across the face with her open right hand as she said. “Strip bitch.”
I towered over her, rubbing my check. After a long moment, I made the last free-will decision I would ever make. I began unbuttoning my shirt.
“Fold you clothes carefully and place them on the coffee table.” Sheila said, as she returned to her seat.
“I told you the little fag would do it.” Jenny said looking at Sheila. She was absolutely giddy with excitement. “You can’t imagine how much fun this is going to be, our very own slave.”
I undressed and stood before them. My eyes were on Jenny because in my mind she had to be the catalyst for this unbelievable turn of events. She was very pretty, but at that moment, her pointed chin and small mouth struck me as shrewish.
“Get on your knees sissy and don’t eyeball me.” Jenny said.
I obeyed, starring at the floor.
In an ominous tone Sheila added. “It’ll be in your best interest not to ever look a woman in the eyes again, and I damn sure better not catch you looking at their tits or asses. My suggestion for you would be to develop a foot fetish.” She walked over and stood in front of me, cunt to nose so to speak. “Do you understand?”
“Yes.” I said.
“Yes. Is that how you address your superiors?”
“No. Ah, Ma’am. Ah, Mistress. I mean yes I understand, Mistress.”
Sheila continued. “We know about your girly clothes and your fag magazines. So, I’m sure you’ll be pleased to know you’ll be spending the rest of your life as a girl. You’ll be a maid and a slut, but a girl nonetheless. Do you understand?”
“What, no thank you.”
“Oh, thank you, Mistress.”
“Thank you, Mistress my ass.” Jenny said. “Look at his weenie. He’s getting hard.” She pounced on me, grabbed my face and forced me to look at her. “You love the thought of being in panties don’t you, bitch?”
“Yes, Mistress.” I said. I couldn’t turn my head, but I tried to avert my eyes from her.
“Yes, Mistress.” She said in a singsong, mocking tone. She released me, returned to the stool and added. “You best keep that thing in control around me or I’ll have it cut off.”
“Let’s establish a few ground rules.” Shelia said. “Never speak unless spoken to. You won’t need to ask questions because our instructions will always be perfectly clear. When addressing Jenny or me, you’ll refer to us with respect such as ma’am or mistress. Do you understand?”
“Yes, Ma’am, but.”
I didn’t get my question out. Sheila leaped from her seat and backhanded me across the face, knocking me off my knees. “But is not a part of your vocabulary ever again.” She calmed down, pointed to her left and asked. “Do you see the rug in that corner?”
All the floors in downstairs area of our home were honey oak and there were numerous fine rugs. The one to which she referred was a small silk Turkish. I looked first at the rug and then at my beautiful young wife. “Yes, Ma’am.”
She kicked me in the stomach. “Don’t look at me, bitch.”
“Yes, Mistress I moaned.” Clutching my stomach with both arms.
“When Jenny or I give you the command — Rug, you are to go to that rug and kneel down with your face on the rug and your ass in the air. You’ll most likely be punished. Do you understand?”
“Make him go now.” Jenny said in a playful tone. “He looked. He looked at you.”
“Go to the garage, get me a ping pong paddle and go to the rug.” Sheila said.
Naked, I headed toward the garage.
“Move your ass.” Sheila added.
Returning from my errand, like an obedient puppy, I handed the paddle to Jenny and assumed the position. I faced to the wall so I couldn’t see what was coming, but I heard the paddle on its downward swing. The pain was astonishing.
“Your turn.” Jenny said, apparently handing the paddle to Sheila.
After delivering two hard blows to my ass, Sheila placed the paddle on my ball sack and told me to spread my legs. Fearfully I complied.
“Do you think you can be a good girl now?” She asked.
Girl was my thought, but I was in the absolute wrong position to ask questions. “Yes, Mistress.”
“Then go back where you were and see if you can convince Jenny that you really want the life we’ve described.” Sheila said.
After I was kneeling in front of Jenny, I clamped my hands as if in prayer and looked at Jenny’s feet. “Please, Miss Jenny, please sissify me and humiliate me any way you wish. I’ll obey your every command.”
“My bet is you’ll live to regret those words.” Jenny said, then speaking to Sheila she added, “Get on with it baby.”
Turning to Jenny, Sheila asked, “What shall we call her?”
“What’s wrong with Sissy?” Jenny said.
“Nothing at all. As a matter of fact, I think that’s perfect, but we’ll need something for her ID.” Turning in my direction she asked, “What do call yourself when you are dressed in women’s clothes?”
“Jamie, Mistress. Jamie Jo.”
“Very well then. We’ll make everybody happy. Your ID will carry the name Jamie Jo Moore. Jenny and I will refer to you as, Sissy. Are we agreed?”
Resigned to my fate, I nodded in recognition not that I think they really wanted my approval.
Sheila laid a form on the ground in front of me. “This form will give me complete control of your money and your life. Signing it will be your last act as a man. Of course, you might prefer a nice divorce where all your transsexual inadequacies are made public.”
I signed it in two places and initialed it in two more.
She squatted in front of me to pick the papers up and kissed me on the forehead. “I did love you to a point, but my body requires a massive dick and you can’t help me there, can you?”
“No, Ma’am.” I said. She had never complained about my dick before. It wasn’t very big, but she had never complained.
“You’ll be an integral part of my sex life and you’ll be my obedient slave. I’m sure you’ll make me very happy.”
Sheila was still in a squat when Jenny walked over, put a hand on her shoulder and said, “I don’t have a massive dick.”
I’m sure I was not supposed to look, but Sheila kissed Jenny’s pussy and ran her tongue between the puffy outer lips. Then she said, “But you have the world’s most delicious pussy.” Moving up Jenny’s body Sheila kissed her tummy then cupped her left breast and put a metal filled nipple in her mouth. She stood, looked up at Jenny and said, “I wouldn’t trade you for a hundred dicks or a hundred of their stupid owners either.”
Turning to me Sheila said, “Rug.”
I wasn’t sure what I had done to aggravate her but I quickly assumed the position.
A few moments later Jenny told me to be still. I smelled alcohol as she wiped a place on my butt. She gave me an injection then told me to sit up. She handed me two pills and a glass of water. As I swallowed them she laughed and said, “Hormones, Sweetie. You’ll love what they do for you.”
I’m sure they meant this treatment to be cruel, but I had dreamed of being a girl all of my life and I was willing to pay the price to be one. Any price.
Sheila said, “There are some empty boxes in my bedroom. Pack all your male clothing. We’ll give them to the Goodwill. You’ll be moving to the spare room on the right at the end of the hall.”
The way the upstairs was laid out, a curved front staircase lead from the entrance hall to the double doors of the master suite. Down the hall to the left are the four guest bedrooms two on each side of the hall, each with a private bath. The rear stairway led downstairs to the kitchen.
Sheila continued. “Jenny and I’ll share the main bedroom. You’ll have some household chores, but never and I mean never go into our bedroom without Jenny’s or my permission. Do you have any questions?”
“We’ve setup the guest bathroom for your use. If you have anything left in my bathroom, put in the trash.”
I took me nearly an hour to get everything packed. I placed the boxes in the hall, disposed of my toiletries and returned to the den to find Jenny and Sheila sitting on the couch. I stood quietly with my eyes down.
Jenny said, “I think you’d be smart not to stand when we are seated unless you’re serving us.”
I sank to my knees. “Thank you.”
“Sheila, why don’t you call your hunk of meat? I’ll take Sissy to her room and get her acclimated.” Jenny said.
“That’s a plan.” Sheila said. “But just introduce her to phase one for the moment.”
Jenny saluted as if accepting a command.
I followed Sheila into my new bedroom and found they had been busy. The door to the room had been removed. The walls were painted a soft pink. There was a pink satin spread and several satin pillows on the bed. The dressing table, bureau of drawers and nightstands were white enamel. Framed pictures of nude male dancers dotted the walls, but the most startling change was the mirrored ceiling and recessed lighting. The room was very bright and very feminine.
“We’ll start in the bathroom.” Jenny said.
Someone had been busy there too. The door was gone. Everything was either pink or white. The ceiling and two opposing walls were covered in mirrors. As in the other room, it was very bright. My nakedness and Jenny beauty filled the room.
“Between electrolysis and hormones, shaving will not be as big a problem in the future, but for now I want you to start with a depilatory. Have you used one before?”
I was embarrassed to all hell and wanted to lie, but dared not. “Yes, Mistress.”
She winked and said. “Then you know it’s hard on your skin. I wouldn’t use it every day.”
She retrieved a large pink bottle from under the sink and handed it to me. I applied the smooth pink liquid to my arms, legs and torso. After the appropriate time expired I got in the shower. When I stepped out I was hairless from the neck down except for my genitals.
“I assume you’ve shaved as well.” She said handing me a can of feminine shaving gel and a razor. “Every morning I want you to carefully shave your legs, underarms and pubic area.” She touched the back of my leg, high and on the inside. “This area is hard to reach. You may find it easier to shave your underarms and back there while looking in a mirror, as you can see there are plenty available. She started a warm bath and added bubble bath. “Now get in the tub and shave.” She sat on the toilet and watched as I carried out her instruction.
When I was finished, I stepped out of the tub, accepted a large fluffy towel from Jenny and dried off.
“Your lotion is in the blue bottle. Put some in every pore of your body. Okay?”
“You’ll sleep in a plain cotton nightie?” Jenny said. “Have you ever worn a gaff?”
She handed me a garment that looked like bikini panties. “Put this on.”
I had it three-quarters of the way up my legs.
“Hang on.” Jenny said. “Push your balls up into your body and pull your dick and ball sack back between your legs.”
I did as instructed.
“Now pull the gaff up and use it to hold everything in place.” Jenny said.
I followed her instruction again. It felt good, like a girdle, but less restricting.
“You might as well wear these.” She handed me pair of white high-cut briefs. They were thin and stretchy with two lace accent panels on the front. I held them to my face. They smelled of powder like my mother used in her underwear drawer. The reminiscence caused pre-cum to dribble from my dick. The bra was a sheer, white 36A cup with a front closure and matching lace accents.
It was probably obvious how much I enjoyed putting the outfit on. How much I enjoyed putting it on in front of a real woman. I’d never been dressed in front of a real woman before. As I stepped into high-heel mules, I creamed my new gaff.
“In case you’d like to know, you look like a chubby transvestite fag. Have you ever sucked a cock?” Jenny asked.
Deflated, I answered. “Yes, Mistress. Once when I was in college.”
“Just once. Does that mean you’re not really a cock sucking fag?”
“Let’s go see what Sheila’s up to.” Jenny said.
She was up to or maybe it would be more appropriate to say down on a young Adonis. The object of Sheila’s attention was a tall, muscular blond. I’d lied when I said I only had sex with a man once. After the first time, I dropped to my knees, subservient to a cock I was hooked. My collage friend had let me dress in my female clothes and service him regularly. I would’ve probably done it in front of the administration building if he had asked me to, but he didn’t.
I’d always been attracted to men in the sense that good looking ones would give me a hard on. I’d fantasized about them and beat off to their pictures almost as frequently as I did women. My favorite masturbation fantasies involved slender young Asian she-males with flat-chests and long uncircumcised cocks.
Looking at Sheila’s hunk, there was no question in my mind I would suck this guy’s dick and offer him my ass. He was a wow! Sheila was on her knees sucking on his dick. It was the length of a polish sausage and half again as big around. It had been circumcised. The big beautiful head was a mouthful and Sheila was working it over.
“Your ex-wife is quite a cock sucker.” Jenny said. “When she has a real cock to suck.”
Ex-wife, Real cock, I thought. At some level, I was embarrassed even angry at what she was doing, but the bottom line was envy. My gaff was getting tight.
The stud said nothing, never cracked a smile. He indifferently pumped away. Sheila sucked, slobbered and moaned both hands partially wrapped around his pole.
“Get on your knees.” Jenny said in a low tone.
I was sure I wasn’t supposed to watch, but Jenny didn’t say anything and I was mesmerized. I’d seen stuff like this in porn movies, but it wasn’t my wife and it wasn’t so close. He stiffened, she became still and after a moment he popped out of her mouth.
Sheila walked over to where I was kneeling, leaned down and kissed me depositing the load in my mouth. It had been a long time, but I hadn’t forgotten the taste, the smoothness. I rolled it on my tongue, pushed it through my teeth and took a deep breath.
“It’s called snowballing.” Sheila said. “How do you like it?”
I didn’t know from snowballing, but I said. “Thank you.”
“Clean my friend up.” Sheila said.
I crawled over and positioned myself in front of him. As if an expert, I started at his balls and licked my way up the shaft cleaning as I went. I loved his musky odor and inhaled deeply. I pressed his meat to my cheek then kissed it several times moving toward its head. Opening wide I slid him into my mouth.
This prompted Sheila to grab a hand full of my hair and jerked me back. “I’ll let you know when I need your help. Besides, the entertainment is over for tonight.”
That’s when I noticed Jenny was recording my performance using a digital recorder.
“Your sissy friends on the internet will love this movie, won’t they?” Jenny asked.
My face begged for mercy, but I dared not ask for it.
“You know where all the best Tranny sites are, don’t you?” Jenny asked. “Will you help me post this movie in the morning?”
“Yes, Mistress.” I said then added a tentative, “Please.” It sounded like a plea for permission, but I hoped she recognized a veiled plea for mercy.
Ignoring my condition, she continued. “This will be the before movie. As we feminize you we will take some more. Do you think the members of your board of directors would like a copy?”
“We can always send them a copy later.” She said. “If we change our minds. For now, you can get to bed. See you in the morning.”
The lights in my room would turn down low but not out. It appeared I would have no privacy at all in my new life. As I stretched out in my pink bed, in my pink room, in my short cotton gown, the thought of a shot of Scotch entered my mind. I needed some help to sleep. For years I had used masturbation as a sedative, but I was confident that would be a mistake.
I awoke the next morning, as if kissed by the proverbial Prince. I was dressed in women’s underwear and a soft cotton gown and it took me a moment to remember the source of this little miracle. I used the restroom, arranged my clothes and went to the sunroom. Sheila and Jenny were eating.
I dropped to my knees and said. “Good morning, may I have some breakfast?”
Sheila whirled around to face me. “Rug – you stupid bitch.”
I ran to the den. It was twenty or thirty minutes before they joined me. Sheila had a wide leather belt in her hand. Jenny tossed my gown over my back and pulled down my panties.
“You spoke without being spoken to, didn’t you?” Sheila asked.
“And what is our position on rules violations?” Sheila asked.
“Our position is zero tolerance.” I said.
As I spoke Sheila rained the first blow on my upturned ass.
The second blow followed quickly and seemed to energize her. I was screaming in pain and begging for mercy. More than a dozen blows fell before she stopped.
“Take her upstairs and get her ready, would you please.” Sheila said looking at Jenny.
Jenny escorted me to my room and told me to undress, bath and shave. She watched my every move and when I was finished she handed me the lotion.
“Every morning I want you up by 5:30. For breakfast you’ll find some diet shakes in the refrigerator. Drink one, bathe and shave paying particular attention to your face. You’ll wear a gaff, panties and a bra. We’re going to allow you some latitude in your dress. There are four pairs of women’s dress pants in your closet. They’ll fit you perfectly. There are four woman’s long-sleeve silk blouses. You can mix and match the colors. You’ll find a pair of women’s loafers in the closet. Get dressed now and meet us downstairs.”
“If you’ll hurry you can grab a shake for breakfast.”
I put my underwear on and selected a gold blouse. It had covered buttons and wide tight cuffs with three buttons each. It had a large floppy collar that was open to just above my bra. It screamed classy lady. My deep brown trousers were tight at the waist and wide at the hips. They had a side zipper and button. I slipped my bare feet into a beautiful pair of backless loafers.
From the neck down, the look was that of a very sophisticated young lady. From the neck up I was a young man. Overall, I was a transvestite or a submissive fag or both, but at that moment I really loved how I felt. I ran to the bathroom so I could get a good look and whirled around and around.
Downstairs, Sheila was dressed in a light gray suit with a white blouse like mine and high-heel pumps. “Let’s go.”
Go never entered my mind till then. I was dressed in woman’s clothes. I had no identification or money. However, the most important fact was that I had no choice. Not even a choice to speak. I trailed behind her like a rag doll.
“You’ll make it through the day if you keep your mouth shut. You dig.”
Our first stop was a beauty shop. Sheila knew everybody. They gave us adjacent spots and Sheila ordered manicures and pedicures. I was way beyond embarrassed. I sat like a mannequin starring at my knees just barely able to resist the urge to run or cry. The women working on me conversed with Sheila as if I didn’t exist. Sheila had her nails done in bright red. My fingernails and toenails acquired a smooth coat of frosted pink. I admired my fingernails. They looked longer and gave my hands a delicate appearance. That aside, I was never more grateful for anything than to be leaving the place.
Our second stop was a doctor’s office. Again, Sheila knew everyone. I was sure the people in the waiting room were starring and whispering, but we were shown back quickly. I stripped and put on a gown. The doctor came in, kissed Sheila and asked how Jenny was doing. After she checked my temperature, blood pressure etcetera, she took blood, stool, urine and sperm samples.
When she returned she said. “He’s fine. Did you give him the first dose?”
“Yes.” Sheila said.
“I’d like to give him some stuff intravenously. When are you going home?”
“About two hours.”
“Okay. That’ll work, but he’ll probably be very sick tonight and he’ll get sick right after you give him his injection the next couple of days. The cocktail we have him on is going to work quickly, but his body will resist.” The doctor said.
“I don’t care how sick the gets. Will he be okay?”
“Absolutely. It’ll be like a sugar overdose. That’s all.”
“Put the stuff in him.”
She filled two hypodermics and emptied the contents into my arm. Then she put a third into my hip. Finally, she gave me a small container of sweet clear liquid. It was psychosomatic, of course, but I felt sick at my stomach immediately. I got dressed and we left.
I recognized the office building we parked in front of to be that of my accountant. My supplication to God almighty went unnoticed and Sheila led us into Bill Carlisle’s office.
She kissed him on the cheek and said. “Hello, Bill.”
“Hi, Sheila.” He said and reached around to greet me. “Hi.” He got out before he assessed my condition. “What’s with the outfit?”
Sheila said. “Didn’t you know Andy was a transvestite?”
“No, I didn’t. I’ve never seen him like this.” Bill said.
“He always wore the underwear. He’s just getting a little bolder.”
“Bolder hell. He’s got tits.” Bill said.
“An under-wire bra works miracles.” Sheila said.
Nausea overtook me. I lunged for the wastebasket and vomited.
“Shit, Andy. What the fuck is wrong with you?” Bill asked.
I hovered over his wastebasket, retching. Bill offered his handkerchief. I accepted then went to his private bathroom. When I returned Sheila was speaking.
“Our taxes are due in two weeks and I can’t keep him out of my panty drawer long enough to help me. Can you help me get our affairs in order?”
“I just can’t believe my eyes, but I’ll be glad to help. Let me get a couple of things from the other office.”
While Bill was gone, Sheila gave me some instruction.
“These lists will help guide you through the various accounts. Do you have the checkbooks?”
“I think so.” Sheila said.
“Call Paul Carter down at First Bank. He knows Andy’s finances well. I’ll help you put the expenses together. I don’t believe there’ll be any problems.”
Following Sheila’s instruction I stood walked behind Bill’s desk and sank to my knees. “May I suck your cock?” I said looking up into his eyes.
“Andy, we’ve been friends a long time so I’m going to ignore that question, but I wish you’d leave and not come back till you get some help.”
Sheila stood and said, “I’m so sorry, Bill. He’s incorrigible.” Then she shook his hand and added. “I’ll call you tomorrow.”
I followed her out like a pull toy on a string, but I wasn’t the least embarrassed. It was a kick. My nipples pebbled from the sheer sluttish kick of it all. Of course, Mistress was not going to be happy I hadn’t accomplished the blowjob. Of course, I wasn’t happy about that either. It had been an awful long time since I’d worked a cock over and I was hungry for the experience.
The lower floor of our house was centered on a large entrance area. Double doors to the left lead to the den and a game room. Double doors to the right lead to the living room and a private office. Double doors in the center lead to a formal dining room, kitchen and sunroom. There were three bathrooms downstairs in addition to the five upstairs.
After breakfast the next morning, Sheila took me to the office. She fired the old computer up and had me help her load some digital pictures in a file named Sissy. She didn’t really need my help. She just wanted to shame me and have me understand her, not so veiled, threat. The pictures were from the night before. I was on my knees servicing her boyfriend. When she was finished she got up and told me to sit at the computer.
“Send an e-mail to your office and tell them you won’t be in anymore. Ask them to send proxy forms here so I will be able to control your stock.” Sheila said.
It seemed like a goofy thing to do, but after all I was a young millionaire. Maybe this was exactly the kind of flighty action they would expect from me. Sheila had been busy. She had a list of my financial accounts. She guided me through them. I transferred some and closed others. At the end of a couple of hours work, she assumed I was broke. She was just about right, but she hadn’t found two accounts. I had $250,000.00 in a Costa Rican account. The same bank held a $250,000.00 line of credit on the house in Nashville. Next, she had me help her change all my passwords to ones only she knew.
“I’m going to take care of you, but like most women you will live in fear of financial insecurity.” Sheila said. “Your life will be a series of mundane, repetitive tasks and if you find any satisfaction it will be because of my accomplishments or Jenny’s.”
“Thank you, Miss Sheila.” Referring to my former wife in cold subservient manner brought a tear to my eye.
As nonchalantly as if she were discussing the weather she said. “We’ll be leaving for Bangkok in the morning. Your surgery will be done there.”
“Surgery?” I said without thinking.
Sheila stood, pulled off her panties and stuffed them in my mouth. “Are you ever going to learn not to speak unless spoken to?”
I nodded dramatically. For a moment, the fear erased the shock, but reality returned. I was aware of sex reassignment surgery and I knew it could be done in many places around the world, but I didn’t want to lose my dick. I wanted to look like a girl, but I wanted my dick. There had to be some way to object before it was too late. Maybe Jenny would help. I became woozy and purged, including Sheila’s panties.
“You stupid fucking bitch.” She said as she popped me on the back of the head. “Get that cleaned up and get rid of the panties.”
I scurried away grateful for the opportunity to get out of her presence. When I was finished cleaning up the mess I went to my room. When Jenny arrived, I was still fully dressed.
“Get out of your pants and blouse.” Jenny said.
I did and sat on the bed.
“Lay down on your tummy.”
When I did, she pushed my panties aside and injected me with my hormones. I felt sick at my stomach. She gave me some cold fruit juice and a hand full of pills.
“You better rest for a while. Put on your gown, I’ll get you up after lunch and we’ll get you packed.”
“Thank you, Miss Jenny.” I managed.
It was closer to 4:00 that afternoon when Jenny rousted me. Packing was certainly no challenge. Gaffs, panties, bras, pants, blouses and loafers joined cotton gowns and my toiletries.
“Where’s your passport?” Jenny asked.
“It’s in the safe in the office.”
“Go downstairs and look in the refrigerator. There’s a strawberry shake in there for your dinner. After you eat, set your clock for 3:00 and try to get some rest. I’ll leave an outfit out for you.”
She grabbed a hand full of gown and tit then gave it a twist. “Keep your damn mouth shut.” Relaxing her grip, she added, “Please what?”
“Please don’t let them cut off my dick.”
“Go get your dinner.”
I had an edgy night and got up with the alarm. The bath was wonderful. I shaved and washed my hair. I decided to wear it combed back in a wet look.
I don’t know why, but the outfit was a shock. I put on my normal white gaff, panties and bra. The first additional item was white cotton knee-high socks. The shirt was a white silk cowgirl shirt with pink roses and piping. The pants were low-rider jeans in pink leather. My footwear was a pair of pink cowgirl boots. The belt was white leather with a big silver buckle. It read Sissy in big gold letters. A white cowgirl hat with a large pink rose in the hatband completed the outrageous look. I couldn’t have stood out any more if I were wrapped in a flashing neon sign that read FAG.
Shelia and Jenny were comfortably dressed in jeans, short-sleeve shirts and backless sneakers. They’d arranged for a limo and we were off. The trip to Los Angeles took six hours and once we made our connection it was nineteen more hours aboard Thai Airlines to Bangkok. One of the passengers pointed out that another name for Bangkok was Krung Thep. It was Thai for City of Angles. We were flying from the City of Angles to the City of Angles. Oh well, maybe that wasn’t important, but when you wear pink leather pants you need to know some interesting shit.
We were in first class and the flights were as comfortable as possible. I rested and could drink and eat normally although I still didn’t feel to spiffy. My appearance was a constant source of embarrassment, but by the time we arrived in Bangkok I think everyone had grown accustom to the show.
It was 1:00 AM local time when we checked into a suite at the Royal Orchid Sheraton. The rooms were opulent. The great room featured a domed skylight with chandelier. The furniture was French colonial. The entertainment center included satellite TV and a state of the art audio system. There was a long, well stocked bar with a huge balcony behind it. There were two bedrooms with canopied beds and Jacuzzis in the bathrooms.
Sheila and Jenny decided to get up at 7:00 to minimize the effects of jet lag. I was startled and disoriented when my clock went off. I was literally clutching my dick and probably had been all night. With no regard for the consequences I ran to my bathroom and masturbated. I was in the tub when Jenny walked in. She was already dressed.
“Breakfast is served. You need to get moving.”
I dressed in charcoal pants and a pale pink shirt. I ate a small breakfast on the floor by Sheila’s chair.
They gathered their belongings and Sheila said. “Let’s go.”
I was shaking with fear and they kept pushing me along. I looked like a prisoner in custody. By the time we got a cab I was crying, but they made no attempt to console me. We pulled into a clinic not far from the hotel. It was clean and the people were very nice, but of course they weren’t having their dick cut off. I sat sobbing with Jenny while Sheila made the arrangements. I was taken back to a private room and instructed to undress. Shelia and Jenny left without saying a word. Alone and afraid I felt like an abandoned child.
The day creep by interrupted by poking and prodding and tests. Late in the afternoon they put me on an IV. They either put something in the IV or I finally gave in to exhaustion.
I think my clock read 5:00 when they started moving me. My next recollection was numbing cold and then my room. My arms and chest were tied down. I couldn’t move and I hurt everywhere. There was a young nurse in my room. I tried to ask her about my condition, but the most noise I got out was a squeak. There was something wrong with my throat. She came to my side and offered me a drink through a straw. I accepted it and drifted off again.
I’m not sure what day it was, but I clearly remember the event. There was a bedpan between my legs and I was pissing through my dick. My dick was still there. This wonderful event triggered my complete and rapid recovery. My little nurse helped me get up and explained what they had done.
They had cropped some material off my earlobes to make them smaller. They had shaved my Adam’s apple and worked on my vocal cords. They had done a breast implant and removed some material from the bottom of my rib cage. They hadn’t touched my dick. I was so excited the nurse became concerned I’d bust a stitch.
I think it was the afternoon of the fifth day that Sheila and Jenny showed up. One of the doctors was with them. The three of them talked about me like I was an expensive pot. The bottom line was I would move back to the hotel. The doctor wanted to see me before I returned to the United States.
Comfortably ensconced in our luxurious surroundings I began to recover. I learned my mistresses had not been wasting their time. They had taken a three-day cruise down the Chao Phya River and had taken a private tour of the bridge on the river Kwai.
Jenny’s favorite place was a local nightclub named Christie’s Club. They claimed to have fifty hostesses and Jenny was trying to eat them all.
The second night I was out of the hospital they made reservations for the Calypso Cabaret and each hired an escort. Sheila’s date was a tall beautiful Frenchman. His accent was melodious. Jenny hired a very young local. She was short with straight black hair down to her waist. Dressed in formal wear, they made a striking ensemble.
It was early morning when they came clamoring into our rooms. I was asleep on the couch, but I quickly got to my knees to await their pleasure. Jenny took her Thai beauty to my bedroom. Sheila told me to join her and the hunk in her room. They striped, and let me tell you Sheila’s body was incredible. Speaking of incredible, he had an incredible dick hanging between his legs. Sheila got on the bed and spread her legs to the sky. With no foreplay, he shoved the dong into her glistening bald pussy. They were like a lion and a tiger locked in raw sex. It was hard to determine if they were fighting or making love. Sheila climaxed and howled like a wolf, but never let up. There was a literal sucking sound as he pistoned inside her. When he came he stiffened five times filling her to overflowing.
“Get over here, Sissy.” Sheila said, pounding the bed beside her.
I lay on my back next to her. Her Frenchman stood then she rolled over on top of me planting her sloppy pussy on my mouth. She hugged and kissed the Frenchman extolling his prowess while dumping his seed in my mouth. He dressed and left after Sheila rolled over drunk and spent. I went back to the couch. I didn’t sleep soundly, but I never heard Jenny’s little friend leave. After the doctor made his final visit, we stayed a couple of more days. Sheila and Jenny visited temples during the day and prowled during the night. They found a place owned by an American called The Cat House and stopped by the Hard Rock Café long enough to get us all a tee shirt, but their night life always seemed to gravitate to Christie’s Club.
I hadn’t had a real bath in nearly two weeks, but the morning we were to leave I was allowed one. My new breasts were tender, but I’d been given small implants and the swelling had really gone down. My ribs were uncomfortable, but tolerable. I didn’t recognize my own voice, but it didn’t hurt to talk. All in all, the trip to Thailand was a smashing success.
Jenny had bought me some new brassieres made for gals with breast surgery. They were very supportive and comfortable. I wore a white blouse and navy pants for the flight. Jenny insisted I wear navy knee-highs and navy pumps with one-inch heels. I still looked like what I was — a transvestite, but I had become a lot less sensitive to the opinions of others.
Our trip was long, but uneventful. I was glad to be home, but unbeknown to me the other shoe was soon to fall.
The first Sunday morning after we returned, I got my first glimpse of what my future life would be. And it was nothing short of terrifying. I was in the kitchen drinking my breakfast when Sheila walked in. I dropped to my knees.
“Finish your drink and go to your room.” Sheila said. “Jenny is waiting on you upstairs.”
There was a threatening tone to her voice. “Yes, Mistress.” I said.
I found Jenny standing in my bathroom naked save for a skimpy silk nightie. I went to my knees, eyes down.
“Sissy, you may not think so, but up to now your life as a woman has been easy. We’ve allowed you to put on panties and prance around like a girl. Well, those days are over. Going forward you’ll understand that we pay a heavy price for beauty and that we are abused.” She pointed at the vanity. “Under the sink you’ll find a large plastic lined, terry cloth sheet. When you are given the Toilet command, spread it out on the floor and lie down on your back.” She could see the confusion on my face. When we use the Toilet command you’ll be drinking piss. Now, doesn’t that sound like fun?”
I didn’t respond.
“You probably can’t answer until you try it, so get undressed and we’ll try Toilet.”
I didn’t understand why they were in such a foul mood and I had no intention of drinking piss. “No.” Involuntarily came out of my mouth. She was probably expecting it, but in any event, she moved like a cat. Before I could blink she kicked me in the nuts and I dropped like a sack of potatoes.
“You piece of shit, don’t ever say no to me. I’ll have your fucking tongue ripped out.”
I got out of my clothes, crawled over to the counter and started searching for the sheet. I spread it out and lay down on top of it. I could see my reflection in the ceiling mirror, naked and holding my nuts.
Jenny stepped across my chest with her right foot and knelt with her tummy to my face straddling my chest. I placed a hand on each of her soft white cheeks and pulled her to my face. She began to pee before I was ready, but my jaw flopped open and she filled my mouth with the hot, fetid fluid. My stomach was rolling, but the unrelenting flow left no option but to swallow.
Sheila was standing in the doorway watching the action. “Damn, Jenny you’re a real pisser.”
Both girls roared with laughter. Jenny finished and said, “Lick me clean toilet mouth.”
The vile ceremony took a more pleasant, sexual turn. I slowly licked at her pussy. She pushed back then slapped my face. It hurt. I was glad the toilet training was over, but I really wanted to service her pussy. I wanted to dress as a girl and service a girl.
Sheila, still leaning in the doorway, smiled and said. “Toilet.”
I could’ve fought my way out of the house and every cell in my body wanted to run, but the obedient little girl in me lay still. Sheila positioned herself over my face and began to pee. The fluid was very warm and splashing all over both of us. My eyes were closed, but I could hear the hissing stream exiting her body. The smell and taste were something less than shit, but beyond fowl.
As I gulped her fluid, Sheila was clapping her hands, wiggling her ass and singing at the top of her voice. “Go, Sissy. Go, Sissy. Go, Sissy.”
A few moments later it was finally over. Sheila got up, wiped her pussy and left the room.
“Wash your face and brush your teeth.” Jenny said. “There’s mouthwash in the crystal container on the counter.”
Jenny sat in a rocker in my room and watched as I completed my assignment. As soon as I finished she joined me and said. “I’m going to go over your morning routine. Your enema bag is in the linen closet. There’s also soap and a thermometer on the top shelf.”
My enema bag was a two-quart beauty with a double Bardex tip. Jenny gave me explicit instruction on mixing the soap and the water temperature. I hung the bag by the tub, expelled the air from the tube and put the first bulb inside me. With both bulbs pumped up I got on my knees with my butt in the air and opened the valve. At first, the warm rush felt good, but as my colon began to fill the pain began. By the time the last of the fluid was in me I was in severe pain. I shut the valve and stood. My belly was extended and walking was very uncomfortable.
“There’s a mechanical timer by the sink. You can expel the fluid in five minutes.” Jenny said.
I set the timer, stooped over with my hands on the counter and looked at myself in the mirror. Was there any way to do this every day for the rest of my life? The timer dinged, I sat on the toilet and removed the apparatus. As I relieved myself, Jenny explained she wanted me to douche a second time with plain warm water and that I didn’t have to hold that one.
After the second douche, Jenny continued, “Have you ever used a tampon?”
I hesitated a moment before admitting, “Yes, Mistress.”
She winked and said. “They’re in the top drawer of the vanity. Put one in you now and wear one all the time except when you sleep.”
I lowered the toilet seat, placed my right foot on the top and unwrapped the super plus tampon. I started to put it in my mouth for lubrication.
“There’s petroleum jelly in the same drawer. Use that.” Jenny said.
I bent over and pushed the tight cotton cylinder home.
“Start thinking of that hole as your pussy. Keep it clean and lubricated at all times.” Jenny started running a bath and added scented bath salts. “I want you to continue your shaving and bathing regiment.”
I shaved the backs of my legs and my pits then slipped into the tub to complete the job. I lay back and shut my eyes. While I soaked, Jenny plucked my eyebrows into a high arch, shaved my face and applied a mudpack. I was aware that she left and I relaxed. Clean inside and out I stepped out of the tub and dried off with a fluffy pink towel. I applied lotion to my body and touched up my frosted pink nails. Jenny returned to help me with my makeup and a short blond wig. I put on a white gaff and she helped me into a white corset.
“You’re still overweight, but we will help you with that. In the meantime, the corset will help with your figure.” She started tugging on the cords and asked. “How are your ribs?”
“I’m okay, thank you.”
That confession cost me another inch in my waist. She handed me pink stockings with lacy tops and I put them on.
“When you wear the pink outfit, wear the white heels and these.” She handed me a white leather collar and white leather bracelets. They had silver “D” rings attached every 90 degrees. “There’s a black set of bracelets and a black collar for those occasions you wear the black outfit.” She handed me five small locks. “Use these to lock your shoes, bracelets and collar in place. I’ll keep the key.”
The rest of my outfit included ruffled white panties, a set of crinolines, a pink French maids outfit and a little pink cap. I looked in the mirror and gasped. There was a tall passable woman looking back at me.
“Wear this outfit unless you are told otherwise.” Jenny said then she took me to my room and handed me a short white flannel gown. “You have four of these, wear one every night unless we lay out something else. Rinse out your bra, panties and hose every night and hang them in the bathroom to dry. Okay?”
“Use a cleanser on your face and apply lotion to your entire body. Remove everything from your pussy before you retire and lubricate it. I’d suggest you get up at 5:00. Do you have any questions?”
“I hope not because there will be no tolerance for mistakes.” She paused then took my hands in hers and kissed me on the cheek. “I know this has been rough. There’ll be more rough stuff, but if there’s a real woman inside you somewhere, you’ll survive.” As she left, she said. “Goodnight Sweetie, have breakfast ready at 6:30.”
I reveled in Jenny’s act of kindness. It took me forty minutes to prepare for bed and I laid my head down filled with fear, but determined to find that girl inside me and survive.
I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and filled the bag with a smile. Once I had the bag full, the system purged and the bulbs in place, I pranced around the room holding the bag above my head. I liked having the pumps hanging down from my body and slapping my bare legs. My playtime over I assumed the position and accepted the first load. At the proper time, I dumped it and took the second one. Putting a tampon in my pussy was always a kick. That morning it seemed even more special.
The bath was luxurious. I added bath oil to the bubbles and soaked before running a razor over my body. My nails were fine. I smoothed lotion over my entire body and powdered my genitals. Jenny was right I needed to lose some weight. It was a real struggle to get the corset on. It included full cups and adjustable straps, so my cute new breasts were held firmly in place. The panties were layer on layer of lace with a lot of spandex in their body.
I sat at my vanity, pulled on my stockings and attached them to the corset with white lace garters. My heels were single banded sandals with a strip of leather connecting the heel to the ankle strap. The leather strip had a built in “D” ring. The ankle strap was held closed with one of the small silver locks. As I stood I almost swooned. It’s such a charge to be on heels, especially 4″ heels. Then I noticed the time. It was 5:46 and I needed to get moving.
The crinolines were in a set, five layers to a set. The French maids outfit had a scoop neck and a very short skirt. Over the crinolines it covered nothing. My garters, ruffled panties and lacy stocking top were visible. The apron was shorter than my skirt, but the bodice and straps were layers of ruffles and improved on the stark cut of the dress. I did the best I could with my makeup and wig then clipped the cap onto my hair. The gal in my full-length mirrors was hot. Every guy on the planet would want to get into those ruffled panties. Unfortunately, there was no time to prance around. It was 6:04.
I had two places set at the table in the sunroom; hot tea prepared and toasted bagels ready when I heard the patter of bare footsteps down the hall. I had even set some fresh flowers on the table. I was beaming with pride. The breakfast was served; I was a vision in pink, and I had four minutes to spare.
Jenny was naked, her hair disheveled and she was rubbing her eyes as she entered the dining room. She said, “Toilet.” Then she turned and headed for the bathroom.
I’d been primping for an hour and a half and she hadn’t even looked my way. She was going to make me do that disgusting job before Mistress Sheila even got to see me. Up the stairs and down the hall, I got my sheet out and lay down. Jenny flopped her lovely pussy on to my mouth and started without so much as a fair thee well. With my tummy full I licked her a couple of times, but she was unmoved. She stood and left without a word.
I fixed my makeup and hair, brushed my teeth and hustled back to the sunroom.
“Hello, Sissy.” Sheila said.
I knelt between the two of them, eyes down. “Good morning.”
“Did you enjoy your breakfast?” Sheila asked.
Breakfast? I thought, but I’d learned my lesson about questions. Instead I said. “Yes. Thank you.”
“Don’t thank me. Thank Jenny she prepared it.”
I finally tumbled to the deal. “Thank you, Miss Jenny.”
After I’d cleared the breakfast dishes and loaded the washer I knelt before Sheila in the sunroom. She said. “Jenny is waiting in the living room. She’ll go over your household duties.” She held a steak knife loosely in her right hand. I didn’t remember setting it out, but her manner didn’t seem menacing.
“This whole operation was mostly about taking your money, but there’s a potential here for you to find happiness. Make no mistake, every time you fuck up I’m going to discipline you and I’m going to enjoy hurting you.” With that she placed the point of the knife on my left inner thigh, just above my stocking top. She pressed it to the point of pain and a trickle of blood.
“Yes, Mistress.” I said, eyes down, jaw clinched.
“Get out of here.”
Jenny had a day-by-day list of duties most of which were domestic in nature. I would be doing laundry, cleaning, polishing and vacuuming. I’d be responsible for breakfast and dinner every day. On weekends and holidays, I’d serve lunch.
“At this point we don’t want you to go outside, but that day will come. We’ll also do the shopping until you are more passable as a girl.”
“Thank you, Mistress.”
“I hope Sheila made it clear that our policy with you is no toleration. You make a mistake we’re going to hurt you.”
I rubbed my inner thigh, but she didn’t seem to find the event significant.
“We’ll enjoy taking our sadistic tendencies out on you. Of course, if you have little masochistic urges then all you must do is fuck up.”
We went through every room in the house except the master suite and she covered what was expected in every area every day.
“We don’t intend to trap you. We just want the work done and we want you to learn to be an excellent maid.”
“Like most servants you will be expected to perform sexual favors for your master and in your case, that includes toilet service.”
I nodded in compliance.
During the next couple of weeks I learned exactly what was expected of me. It had always been fun to sashay around in high heels. I found it was quite another thing to work in them for eight or ten hours. At the end of every day my feet and legs were killing me. To make things worse, the first time Jenny caught me with my seams crooked, she removed my shoes and beat the bottoms of my feet with a bamboo cane.
There were dozens of violations that drew various degrees of discipline. My first attempt at doing the laundry was a typical disaster. I hand washed several pairs of panties, but I mixed the colors. Everything ended up some color of red. I didn’t get the connection, but for the next two days they added Tabasco sauce to my second morning douche.
I had no training as a cook so it should have been no surprise when I overcooked some steak for dinner one night. They cut the steak in chunks and watched me remove my tampon and jam the pieces up my pussy. I wasn’t allowed to remove them until I retired.
Of all the outrageous tests, Jenny checked the baseboards in the den with a white glove. They didn’t pass. They didn’t even come close. I spent the afternoon in the corner, bent at the waist with my wrists attached to my shoes. They didn’t beat me, but it was the next morning before my back quit hurting.
There was something every day. It was obvious to me that a satisfactory job on my part was a pipe dream. They always found some minor infraction and delighted in punishing me. Their favorite targets were my nipples. The hormones had them puffy and sensitive. Over time, using tit clamps, they attached everything but the front bumper from a car to them.
After breakfast every day I was given a hormone injection and four different pills. I had no idea what the pills were and wondered if they were poisoning me, but I decided they had everything I owned so what would be the point.
Each mistress used me as a toilet once a week in lieu of one of my meals. When they had visitors, I was the entertainment. They would show me off then Jenny would piss in my mouth. Before they left, I would service every pussy or cock in the place.
My diet was a startling change. We used the sunroom on the backside of the house for most meals. The slanted ceiling and three outside walls were glass and the floor was a rich brown stone. There was an immaculately manicured garden surrounded by a high brick fence. I normally ate with my mistresses. The significant difference was that I sat crossed-leg between them on the floor for my meals.
They had continental breakfast most mornings. If they ate meat it was in small portions. I had a delicious diet shake. They ate lunch away from home except on weekends. On Saturday and Sunday, I served a half a deli sandwich with cold slaw, potato salad or a fruit cup. I had a delicious diet shake every day in my choice of flavors. Their evening meal was planned well in advance and included steaks, seafood and pasta, but the portions were tiny. I had a small salad with low-fat, low-cal dressing. Once a week I might get a small piece of chicken or fish. I was allowed a diet snack bar or a piece of fruit at 10:00 and 3:00. I kept fresh veggies cut in the refrigerator for all our use. My choice of beverage was water or water and I could have all I wanted if I wanted at least a gallon every day. They even had a bottled water chiller installed in my bedroom.
Sheila and Jenny jogged together most afternoons. While they jogged I changed into a two-piece yellow swimsuit for an hour or so of sunbathing. The bottom to my suit was T-backed and the top was like a normal back-closure brassiere. My tan lines became obvious. When they returned home we all did aerobic exercises, which meant I had to change clothes again. My exercise outfit consisted of a white gaff, white tights, a pink short-sleeved leotard and white sneakers with pink trim.
At the end of the first two weeks the bloom was off the rose. My feet hurt. I was hungry. I needed some sleep and most of all I was isolated. I needed a friend. When I signed away my manhood I was sure I wanted to be a girl. At that point I wanted a hamburger, a beer and the television clicker.
My plain cotton gown felt extra soft and comfortable that Friday night, but I was resolved to escape at the next opportunity, perhaps the next morning.
The strong resolve of the night before seemed to dissipate considering the morning sun and the Bardex in my twat. I had to admit to myself I was a sissy, a coward and a slave. I was dressed and setting breakfast on the table when Sheila walked into the kitchen.
“Sissy, make me a Bloody Mary.”
I really wanted to say — Zap You’re a Bloody Mary, but I settled for fixing her drink. A late night no doubt, I thought. By the time I served the cocktail, Jenny had joined her and they were disposing of the morning meal. I sat the drink by Sheila and knelt between them. To my amazement they were jabbering about me.
“His Mother had to know he was wearing her clothes. He’d have stained every piece of lingerie she had.” Jenny said.
“But she never said a word to him.” Sheila said. “Or at least that’s his story.”
“Denial?” Jenny asked.
“I guess. His Dad took a more positive approach. He gave him a good talking to, sent him to a shrink and tried to fix him up with a couple of young girls.” Sheila said.
“You can lead a horse to water.” Jenny said.
Sheila interrupted. “But you can’t change its spots.”
“You think he was born a transvestite?” Jenny asked.
“Beats me. I guess he could’ve been, but if makes any difference, I think he was abused as a kid.” Sheila said.
“Sexually?” Jenny asked.
“Yeah.” Sheila said.
“His Dad?” Jenny asked.
“More likely an Uncle or a neighbor. By the time he got to college he was wearing panties every day. He never missed a chance to suck his roommates cock.” Sheila said.
Jenny nodded along as Sheila continued with stories about my college days until they were finished with breakfast. Of the many forms of humiliation, I was experiencing, having intimate details of my life discussed in front me might have been the cruelest.
Sheila turned to me and said. “When you’re finished with the dishes, there’ll be an outfit on your bed. Comb your hair, don’t wear a wig and wash off your makeup. We’ll be ready to leave in thirty minutes so get moving.”
My outfit consisted of a gaff, white pantyhose, pink short shorts and a short pink open-mesh tee shirt that didn’t hide a thing including my belly. Tit clamps connected by a heavy chrome chain lay on top of the outfit. I assumed the white leather collar; white bracelets and white heels were appropriate.
Jenny and Sheila were waiting on me in the living room. They wore halter-tops, jeans and tennis shoes. They looked great. I looked like a shameless, transvestite slave and that status was accentuated when Jenny attached a leash to my collar. We were going outside and I had nowhere to hide.
The cowgirl outfit had been one thing and not a very good thing, but this outfit was way over the top. You could see my bare tits for Christ’s sake. I’d been to Bourbon St. and Frisco. I’d see transvestites and public bondage, but in those circumstances the people seemed more like entertainers than freaks. In this outfit, I’d engender disgust and loathing on the part of the observer. I fell to my knees and said. “Please.”
Sheila didn’t hesitate. “Rug.”
I followed her instruction.
After a few moments Sheila said. “Up on your knees.”
Using two short chains she attached my bracelets to the “D” rings on my shoes. She held my tee shirt up, increased the pressure of my tit clamps then scared me to death. She clipped a wire to the chain between my tits. She unzipped my shorts and pulled them down to my knees followed by my hose and gaff.
“I’m going to help you bend forward so you don’t hurt your face.” Sheila said.
My dick was hard as a rock and there was a pronounced tremble in my voice. “Thank you, Mistress.”
My face and upper chest were on the rug. My ass was in the air. Sheila pulled the wire from my tits back between my legs. She removed my tampon and pushed a cold cylinder into my pussy. I couldn’t see it, but the cylinder had a wire coming out of it and both wires terminated in plugs. I heard the plugs being pushed into receptacles on the wall and I heard the front door open. I didn’t see Sheila signal Jenny to push the doorbell.
My body snapped hard. The electricity ripped a path through me causing me to thrash around in pain. Inside I was screaming, but the sound didn’t come out until Jenny let up on the button.
Sheila slapped my ass with her open hand then asked. “On what basis do you think you have the right to refuse me anything?”
“Nothing, Mistress. I’ll do anything you ask.”
She signaled Jenny. I was on my side jerking spasmodically against my chains unable to escape. My shrieks came in waves.
The electricity stopped and Sheila said. “Your damn right you will. You’re anxious to go with us, now aren’t you?”
“Oh yes, Ma’am.”
“You’re a fucking liar.” Shelia screamed. She accented her point by ordering a short burst on the button.
“Oh please, Mistress. I’m confused. I don’t know what you want me to say.”
“I’m embarrassed and afraid.” The truth was rewarded with another series of zaps.
“You have no self, so how can you be self-conscious? You exist only for our pleasure and if you’re not certain we’ll take care of you then you’re in deep shit. Clear?”
“We’ll take you out in any condition we please, but we will stay within the law. If you see a woman keep your eyes on her feet. Look every man in the eyes, and then stare at his crotch and lick your lips.” She pulled the cylinder, unclipped the wire to my tit clamps and said. “Get cleaned up and put in a new tampon. We are late already.”
We drove to a medical building near the hospital. They paraded me across the parking lot, up the elevator to the third floor and into a large waiting room. I was embarrassed, but I sat in a corner starring at the crotch of a man directly across from me. After an interminable wait, I was shown to a dentist’s office. The doctor was very beautiful. She made no pretense about her passion for Jenny.
“Can we go to my office while Angie takes the impressions?” She asked Jenny.
Jenny didn’t answer. She just led the dentist away. Angie made x-rays of my mouth and took impressions. Sheila just sat in a chair and observed. When Jenny returned she told Sheila that everything would be ready in two weeks. I wasn’t allowed a question, but I sure had some.
Our next stop was a small strip mall near the University. Shelia and Jenny walked hand in hand looking in the shops. I trailed along behind a freak on a leash. When we were near the end of the mall they walked inside a shop, a tattoo shop. We were greeted by a short trim male with a ponytail. He was a walking billboard for his trade and sported a wide smile as he greeted my wife.
“Shelia, Jenny what a treat.” He put his arms around them both, but kissed Sheila on the mouth. Jenny stepped away and Shelia straddled one of his legs. As they embraced, she humped his leg like a dog in heat.
She whispered something in his ear and dropped to her knees. Jenny locked the front door. Sheila unzipped his leather pants and pulled them down to his knees. He wore no underwear. His legs were smooth shaven and there was an elaborate tattoo crawling up his left leg. His dick was long and slender, but the attraction was his Prince Albert. It clanked on Sheila’s teeth as she dropped his limp meat in her mouth. It didn’t stay limp long.
She slurped and bobbed running him down her throat and burying her nose in his pubic hair. I had no idea she could do such a thing, much less enjoy it so much. She moaned, rubbed his ass and played with his ball sack. He put his hands on her head and stiffened. She slapped his ass hard and took his load. He flopped out of her mouth; she walked over and gave me my second snowball.
The Tattoo man pulled up his pants, jerked Sheila away from me and kissed her again. “Thank you.”
“It’ll be your turn soon.” Sheila said with a smile. “But for the moment, we’re here on a mission.” Glancing my way, she said. “The slut with your cum in her mouth is Sissy. She needs some work.”
“Great. Let’s get to work.”
Jenny led me to a sort of chair. “Take off your top and shorts. Pull down your pantyhose and gaff.”
I complied and she pushed me back into the chair.
My clothes were embarrassing. My shaved nakedness was worse. Jenny released the clamp from my right nipple and rolled the nipple between her thumb and forefinger. The pain was staggering. I would have never believed it would hurt so much. I grabbed at her hand trying to stop it, to no avail.
“That really hurts, doesn’t it?” Jenny asked.
Pain sealed my lips.
Jenny attached my bracelets to the arms of the chair and ran a bungee cord from the right side of my collar behind the headrest to the left side of my collar. It effectively locked my head in place. She unlocked the ankle straps of my shoes and removed them, then pulled off my pantyhose and gaff. The chair had adjustable stirrups for my feet and Velcro strips to restrain my ankles and calves. To that point the restraints seemed non-threatening. When she buckled a leather strap across my lower chest panic set in.
Jenny put a sleep mask over my eyes before she removed the left nipple clamp and started rolling the nipple between her fingers. I jerked against my restraints and screamed. The most I accomplished was some big old crocodile tears.
I overheard Shelia say. “Yes, in 12-gage.” A few moments later she said. “This is for her navel.” There was some rustling of pages and then she said. “That’s it.” Moments later she said. “Let me show you.”
The chair flattened back and my legs were mechanically forced back and apart. Something touched me just to the right of my scrotum. I flinched, but wasn’t hurt. They touched me several times and then moved to the left side.
Tattoo man said. “Give me till 5:00.”
I heard the tumblers for the front door turn twice and the room went quiet.
Tattoo man wiped my ears with something then stabbed me. It startled me more than it hurt and I realized he was piercing my ears. He put a stud in that hole and stabbed me again. He repeated the process three times in each ear and said. “Keep very still I’m going to work on your lips.”
A machine buzzed. My lips were being pricked. They vibrated and jiggled. Again, I could stand the pain, but the darkness and uncertainty filled me with tension and fear. He worked on both lips for a while and then the machine went silent.
The moment he touched my left nipple I knew what was happening. I felt some pressure and a steady increase in pain then it was over. He fiddled around a moment or two, moved around to the right side and pierced my right nipple. Next came my navel. That was simple, a clamp, some pressure and an insertion. He went back to work on my lips for a while then took a break.
When he returned he said. “Stick out your tongue”
I complied and he grabbed it with a towel or something made from cloth. There was a lot of pressure on the bottom of my tongue and it hurt. I could feel the needle tearing its way through my tongue. The process stopped and then the insert was put in place. He helped me put my tongue in my mouth. The upper ball felt like it was the size of a marble. It wasn’t much smaller. I tried to say please stop, but it came out a lot closer to piss top. It was a freaky, unwanted, uncomfortable feeling. While I was contemplating my new piercings, he moved between my legs.
There was the rubbing or cleaning next to my scrotum, a clamping pressure then a short stabbing pain. Something was pushed under my skin, but he had to manipulate it. The pushing and pulling didn’t hurt, but I was totally baffled as to the purpose of the whole procedure. If one such course of action was curious imagine my shock as he repeated the process five times to a side. I was in a fog, but I was pretty sure I had twenty new holes and twenty new studs in my body. He clamped my philtrum and punched number twenty-one. He put something in the hole and a roll of cotton under my lip. I smelled a strong odor of glue.
Tattoo man left. When I was aware he was there again, he removed the mask. “Hello, Sissy.”
My response was an unintelligible, high-pitched shot at, “Hello, Sir.”
“Don’t try to talk. That thing in your mouth is going to take some getting used to.” He said.
He rolled a tray over and stood next to the chair on my right side. I couldn’t move my head enough to see anything.
“I’m gonna to do a little work around your eyes. It won’t take long and I’m not going to hurt you, but I want you to relax and stay still.”
True to his word, he didn’t take long. He fiddled with his instrument several times and moved between my eyes. I had to assume he was applying permanent eyeliner and mascara. For my part, I couldn’t move but there was more fear than pain.
He sat the chair up, released my hands and put a sheet of paper in my right one. I held the paper up where I could see it was detailed aftercare instruction for the tattoos and piercings. “Sissy, you must follow these instructions carefully. I wouldn’t normally do this much work in a single session, but that’s what Sheila wanted. You must be especially careful with the work I did between your legs. If you get an infection from any of these piercings you could get very sick. As far as your speech is concerned, you’ll be able to speak more clearly in a couple of days.”
He removed the rest of my restraints and led me to a full-length mirror. I touched my lips. They were puffy and a light pink color. My hazel eyes were lined in black and highlighted in a soft blue-green. I tried to be careful and stick out my tongue. The tongue was swollen and the insert was very large.
Tattoo man smiled and said. “You can’t imagine how good that feels to the underside of a cock.”
I hit my tooth with the damn thing when I quickly closed my mouth. My ears contained simple silver studs. My nipples contained silver barbells with stirrups or doorknockers that pivoted freely on the barbell shafts. A silver oval plate dangled over my navel. It was engraved with a single word — Sissy. In rows along my scrotum were barbells complete with doorknockers. Of all the work, the most engaging was the tiny silver stud in my upper lip. It was like a beauty mark. I couldn’t take my eyes off it.
Pointing to a leather-covered table Tattoo man said. “Lay down on your stomach. Shelia wanted me to restrain you, but this won’t be too bad.” He buckled a wide belt across my back then attached each wrist to the belt. He spread my legs and restrained them to the corners of the table with Velcro strips. My tampon cord attracted his attention. He tugged on it lightly then slapped my ass. “You’re serious about this girl thing, aren’t you?”
I said nothing and the buzzing began. He worked on my left shoulder and then on the small of my back alternating between the two. I’m not sure how long I was on the table, but I was very uncomfortable. My arms and shoulders and hips hurt. Still, he continued to work.
“Wow, Terry.” I heard Jenny say. She had slipped up behind me. “That looks great.”
“Your next.” Terry said.
“I might just be.” Jenny said.
“This is just the outline. I’ll add the color later.” Terry said.
“Are you just about finished?” Sheila asked.
The buzzing stopped. “I am finished if you’re satisfied.”
“It’s terrific, but now that I see it I wish you could put a tiny dick on her.” Sheila said.
“No problem.” Terry said and the buzz began again.
When he finished, he released me and I sat up on the table. Sheila and Jenny began an inspection. Jenny flicked a nipple stirrup with a fingernail.
Sheila looked at my lip and said. “That thing in her upper lip is neat. I want one.”
“Now?” Terry asked.
Sheila seemed a bit unsure, but nodded and said. “Yes.”
He put her in the chair and prepped her lip. He used a local anesthetic he hadn’t used on me. While the chemical worked he went to his desk and retrieved a stud. I dared not look at Mistress Sheila directly, but I wanted to understand the process so I used my peripheral vision.
He clamped her lip and gently held it out as he pushed a needle in from the underside or inside of her lip. It slipped in as smoothly as a twig through a marshmallow. He inserted the stud and glued the nut in place. As in my case, he put a cotton pad under the lip and it was over. My stud was a small silver disc. Hers was a diamond. The effect was mesmerizing.
Sheila continued her inspection of me by saying. “Stick out your tongue.”
I did and Jenny said. “Holy cow.”
“It’ll be some dick pleaser.” Terry said.
“Or clitty pleaser.” Jenny said.
Sheila whispered something in Terry’s ear and he said. “No shit. I’ve got to have some of that.”
“You will.” Sheila said then handing me my clothes she added. “Go get dressed.”
I garbled out. “Yes, Ma’am.
In the dressing room I had a chance to see the tattoos. There were two small Egyptian cartouches side by side in the small of my back just above the panty line. On my shoulder was a young woman bent at the waist as if looking at the cartouches. She had large butterfly wings, full breasts and a tiny dick. I got dressed and we went home.
On the way home Jenny told me that my only duties for the next couple of days would be aftercare. “Keep your insides clean, but you can wear your gown and rest. You don’t have to talk until that tongue heals. There’ll be no housework or sex. If you feel up to it, there are some videotapes you can watch.”
I took some prescription sedatives and made it through the night, but the next morning was rough.
I didn’t mind douching, but that morning every time I moved something hurt. Jenny came in while I was on my knees and gave me my injection of hormones. I knew better than to drink on top of the sedatives, but Jenny and Sheila had left a fifth of Scotch in my room. I mixed a drink with no ice and sat in the rocker to watch a video.
As I might have expected the movies were of gay sex. I found I liked the big heavily muscled guys. I was also attracted to big balls hanging low and uncircumcised dicks. I watched long enough to finish my drink and went back to bed.
Mid-afternoon I woke again, made myself another drink and sipped at it while I soaked in the tub. After my bath I rinsed some underwear, put on a new gown, took two more pills and drifted off to sleep again. It was dark when I awoke. Sheila brought me some clear soup, crackers and a vanilla shake. She left without a word, but I was grateful for the meal.
That week was a drug induced blur. I didn’t see much of my Mistresses. I was served one liquid meal a day and I sleep. By Thursday morning I could speak well. The small stud in my upper lip was no problem. My ears were fine. My nipples and belly button were very sensitive. The rings along my scrotum were very uncomfortable, but not sore and my tattoos were okay.
“How are we feeling?” Jenny asked early Saturday morning.
“Much better, thank you.” I said in a clear soprano tone.
“You’ll have that cute little lisp from now on. It’ll make you sound even more feminine.”
I was still amazed at my feminine voice. “Thank you, Mistress.”
“I think I have just the thing to help with that tongue — Toilet.
I was crestfallen, but I knew the day had to come. I assumed the position and she released her stream. I drank it straight then began to lick her pussy. I thought the ball might fascinate her, but it didn’t. She stood and walked off.
As she was leaving she said. “I want you to return to your normal routine Monday.” Looking over her shoulder she said. “And no more booze.”
I really struggled to get through my duties Monday and Tuesday. Again, the big problem was my feet and legs. I had little contact with mistresses except for meals and aerobics.
Wednesday as I was preparing for bed Jenny walked in and said. “Sheila and I won’t be home till late tomorrow night. Don’t wait up. We’ve got a friend coming over Friday night at 8:00. Wear your black outfit.”
Friday afternoon I began getting ready at 5:00. I douched, did my nails and shaved my face. I made a scented bubble bath and shaved all over. My black corset was tight, but the tight cups soothed my sore nipples. I wore fancy black hose with seams up the back and big black satin bows at the top of the seams along with my black sandals. I pulled on a black gaff and black lacy panties. My black uniform and white apron completed the outfit. I applied my makeup, donned a platinum blonde wig and a little black cap. Twirling around I felt the pain of the last couple of weeks fade away. I looked like a beautiful girl because I was a beautiful girl.
I sashayed into the kitchen and dropped to my knees.
“Sissy.” Sheila said. “How are you feeling?”
“Very nice, Mistress. Thank you.”
“Rug.” Sheila said.
Naturally I was afraid, but this time there was good news. When the doorbell rang shortly before 8:00, I wasn’t hooked up to it.
“Sissy, we need a drink.” Sheila said. I got up from the rug, walked over to her chair and knelt next to her awaiting her command.
Shelia wore a short reddish orange nightie with spaghetti straps and a bodice of see through lace. Multiple layers of chiffon fell from an Empire waist to just below her crotch. She was bare legged with four-inch platform mules.
Jenny was spectacular. A black leather collar supported a chain mail top. A black leather band at its bottom hung just below her breasts. Her micro-mini was chain mail with black leather bands top and bottom. Her entire body was dusted in a silver powder. Her clear-plastic, backless sandals had four-inch steel spike heels. She was carrying a video camera.
Our guest was the young blonde male from my first night as a slave. He wore a tan short-sleeve shirt, khaki pants and open-weave leather shoes.
“What would you like, Alex?” Sheila asked.
“A beer is okay.” Alex said.
Sheila draped herself on Alex, her right hand rubbing his dick. “You don’t have to settle for okay.”
“Really, a beer is fine.”
Sheila turned her attention to Jenny. “How about you, Jenny Darling?”
“A little Jose would be just right.”
Sheila turned to me. “Bring us a beer in the bottle and two tequila shooters.”
When I returned they were seated and talking quietly. I served the drinks and knelt beside Sheila’s chair.
Sheila popped her shooter and said. “Let’s see what you got, big boy.”
Alex stood and removed his shirt. He was several inches taller than me and built like a Michelangelo statue. His skin was smooth and tan. He slipped off his shoes, loosened his pants and pulled them down. His whole body was hairless, tan and sculptured. Did I mention his dick? It was such a beauty. Even flaccid it looked like it was a foot long. He had a small bottle of oil. He poured some in his hand and began a slow sensual application to his chest, arms and thighs.
Sheila pointed at him and said. “Get him ready.”
I assumed she meant me and sprang into action. I knelt before him, cupped his balls in my left hand and kissed them. With my right hand, I started rubbing the monster’s head. I kissed and nibbled my way up the shaft. I put him in my mouth, but he jerked back.
I showed him my tongue ball and returned to my ministration. His cock was warm, almost hot, smooth and tasty. There was just no question. I loved cock.
“Get me ready.” Sheila said. She was on her back in the floor.
I dove between her legs and started licking her slippery bald slit. There was just no question. I loved pussy.
“Put him in me.” Sheila said.
Alex got between her legs. I spread her lips with two fingers of my left hand, grasped his meat in my right and guided him inside my wife. Jenny was practically on top of us with the camera.
“Can you spell cuckold?” Jenny whispered in my ear.
Sheila flipped off her shoes, locked her ankles behind his ass and impaled herself on his dong. She screamed for him to fuck her and slammed their bodies together. I don’t think a pussy is a bottomless pit, but she seemed to have no regard for her body. Her ass was off the ground and gyrating. During her first orgasm, she stopped moving long enough to grab two hands full of his hair and kiss him like she wanted to crawl inside his mouth, then she was back to fucking. Their bodies glistened with oil and perspiration. She was amid an orgasm when he stiffened and unloaded inside her.
“Get on your back Sissy.” Sheila said in an urgent tone.
I did so. She pushed Alex away, stood, straddled my chest and plopped her pussy down on my mouth. With my tongue inside her I started to suck. My reward came quickly. The slimy ropes of seaman practically fell out of her body. My tongue ball banged her clitty causing her to gyrate again. The taste, the smell and the heat had me creaming my panties.
When she came, she clamped my head with her legs and rolled over on her back. “Again.” She said.
Her next climax was all she could take. She pushed me away and told me to clean Alex’s dick.
I was busy with that wonderful task when she told Alex to take me to my room and fuck me. I thought I might have died and gone to heaven. Alex pulled me to my feet, and then picked me up in his arms. He was so powerful I felt like a little girl. I relaxed, put my arms around his neck and laid my head against his powerful chest.
He carried me to my room and sat me down on the bed. I told him I needed a quick stop in the bathroom. I pulled my panties and gaff off leaving my hose in place. Then I disposed of my tampon and smeared some KY on my pussy. I lay on the bed next to Alex and held my legs in the air. He needed no more encouragement. He put the head of his dick against my pussy and began to push. I grabbed him, kissed him and pushed back. Once he was in me I understood Sheila’s wild excitement. A man was inside me, moaning with pleasure. He was kissing me and fucking me. All to soon he came. Only then was I aware of Jenny and Sheila and the camera.
“Clean him up.” Sheila said.
His dick was covered in cum and smelled of feces, although I knew I was relatively clean inside. I would’ve kissed and licked on him all night, but as he grew soft, Sheila told me to get dressed for bed. I went to the bathroom and performed my nightly ritual. When I returned to the bedroom they were gone and I fell into a peaceful rest.
Saturday morning I awoke to a tender kiss from Jenny. It was the most startling event of my brief womanhood. “I’m so sorry, Miss Jenny. I didn’t hear the alarm.”
“Chill. It hasn’t gone off yet.” She said and kissed me again. I dared not reciprocate, but she was all over me. She was naked as a baby as she straddled my chest she said. “Let’s see what you can do with that ball.”
It was my first close look at her cunt. The skin on her lips was the same color and texture as her tummy and thighs. Her pubic bone protruded and her lips were fat. She had a thin strip of dark hair about one-inch wide by three inches tall above her opening. My first move was a slow lick, bottom to top with the flat of my tongue. Her little knobby was easy to find. I shoved my tongue inside her and moved it around then flicked her clitty as I came out. I tried to bang her clitoris with the tongue ball by flicking it in and out. It must have had some effect she grabbed my head with both hands and sort of aimed it at her sweet spot. As my next move, I trapped her clitty between my lips and sucked. At the same time, I lightly flicked it with the end of my tongue. When the skin on her back moistened I slowly pushed a finger into her rectum.
She cascaded over the top and screamed. “Shit, Sissy.” And fell limp.
I slowly licked her slit, but she was very sensitive and slid down my body. This time I returned her kiss with passion. Our lips slick with her juices, our tongues entwined.
She was looking in my eyes. “Girl, that was some first-class pussy eating.”
I looked down and said. “Thank you.”
“You won’t need to put on your maid outfit this morning. Just dress in the same outfit you wore to the tattoo shop.” She looked right in my eyes, smiled and added. “Toilet.”
There was no understanding this woman. A moment ago, you might have thought she was enamored with me. Now she wanted to shame me. Whatever. As soon as she moved I ran to the bathroom, got my rug and assumed the position. She dropped down on my mouth and released her warm stream. When she finished she stood and nonchalantly walked off.
I brushed my teeth and gargled before I douched. I had plenty of time, so I soaked in the tub and shaved. Clean, I put lotion on my body, made my bed and straightened my room before putting on my gaff. The mesh on little pink top allowed a clear view of my pierced nipples. I had to clip the chain over the barbells, but I left the jaws loose. The hot pants seemed to fit better. I was sure I’d lost quite a bit of weight. I was hungry all the time, but that’s one of the sacrifices a girl must make.
After breakfast, I did the dishes while they dressed. They emerged in white Capri pants, multi-colored halter-tops and low-heel white leather thongs. Jenny connected my wrists behind my back with a two-foot chain and then attached a leash to my collar. The chain restricted my movements, but the intent was obviously to accentuate my position of subservience.
We went to the same oral surgeon’s office. This time Jenny removed my leash and checked me in. Then she and Sheila left without saying a word. There I sat. A street walker with his/her wrists chained. I thought about removing the chain, but dared not. I just found a man’s crouch to ogle and allowed the other patients to think what they might. Shortly, the nurse asked for Sissy and I struggled to my feet. They put me in a chair and started an IV. My final thought before things went blank was terror. My next recollection was pain. Something was wrong with my mouth.
“Sissy. Can you hear me?” The doctor said.
I didn’t answer, so she asked again. I tried to put my hands to my face, but I was still restrained.
Sissy, it is Dr. Melon can you hear me?”
“Yes, Ma’am.” I managed.
“Are you okay?”
“My mouth hurts.”
“You’ll be fine. I’m going to let you sit for a moment.” She moved her tray in front of me and set a mirror on it.
I sort of drifted off again. I wondered why I needed a mirror and lost it again. My teeth had always looked bad. The girl in the mirror had a perfect set of tiny pearls. Who was she? Off I went. She was I. Searching my mouth with my tongue the fog parted and I realized my teeth were dentures. I just couldn’t stay conscious long enough to assess my condition. The doctor returned, waved something under my nose and I snapped into reality.
“Take these.” She said, handing me two pills and a cup of water. “Jenny is here for you.”
I was reasonably sure-footed, but Sheila supported me on the way to the car.
“Any questions?” Sheila asked.
I damn sure wanted to know why they’d removed my teeth, but I knew better than to ask. “No, Ma’am.”
“Satisfactory answer.” Sheila said. “Well, let me answer the question you’d like to ask. We had your teeth removed so you can suck big cocks better.”
“Thank you, Mistress.” I felt I had to say, but I was shattered by the extent to which they were modifying me.
Our next stop was the tattoo shop. Sheila walked in as if she owned the place. Terry was working on a slender teenage girl. Gold captive bead rings hung from her pert nipples and he was just finishing a yellow rose on her right breast.
Jenny was on her like a vulture. She took the young woman’s left nipple in her mouth and caressed it. Looking up at her young prey Jenny asked. “Does it hurt?”
The young woman seemed self-assured, unfazed. “Nope.”
Terry laid his tool down, wiped the breast and inspected his work. “You’re all set.” He said to the young lady.
Jenny took her hand. “Can we use your back room?”
Terry shrugged. “Sure.”
“I’m going down to the coffee shop.” Sheila said to Jenny. She unchained my hands and said. “Get your clothes off, Sissy.”
“I’ll be down in a while.” Jenny said to Sheila with a big smile.
I stripped and Terry took me to his table and laid me down, face up. He made a careful inspection of each piercing including the tongue, then turned me over. He strapped me down and started to work without a word. He was, I assumed, adding color to my tattoos. I still wasn’t totally conscious, but I was aware he stopped and started several times moving between my shoulder and back. Jenny and the teen had come out and left together sometime during the process.
Terry rubbed something on the cartouches and took a break. When he returned he began working on them, but not with the tattoo gun. It felt like he was sewing something. When he finished he left me on the table and started puttering around the shop. I couldn’t see Sheila and Jenny when they returned. They walked over to the table and inspected Terry’s work.
“Oh, my God.” Jenny said. “They’re incredible.”
Sheila touched my lower back and said. “I’ve never seen anything like it.”
“They’re very rare.” Terry said. “I’m real pleased.”
“What about down there?” Sheila asked.
“They need a little more time.” Terry said. “You want to come by Wednesday night?”
Sheila looked at Jenny then said. “Her mouth will need some time too, maybe we better wait till next Saturday.”
“Saturday is always good for me.” Terry said.
Terry helped me up and Jenny told me to get dressed. In the dressing room, I could see what everyone thought was so great. Terry had sewn silver metal thread around the outside edges of the cartouches. They were brilliant in color and three-dimensional. My little butterfly boy/girl was equally beautiful. Her wings were resplendent with all the colors of the rainbow. As I looked at my back, not only was it beautifully decorated, it was smooth and pretty. I still needed to lose some weight, but there was a definite taper from shoulders to waist to hips.
“Let’s go Sissy.” Sheila said.
Dressed, I chanced another look in the mirror. The cartouches were above my shorts. The butterfly and her tiny dick were visible through my mesh top as were my nipple piercings. My “Sissy” medallion dangled seductively over my navel. Pain or not, my smile could stop traffic.
Once home Jenny took me to my room.
“Here are the aftercare instructions for your mouth. We want you to do all your normal activities, but you will have some discomfort.” She held up a small plastic baggy. “If it gets to bad step out back and smoke one of these. I promise you wouldn’t care if I cut one of your heads off.”
“Thank you, Mistress.”
When my clock went off Wednesday morning Jenny was sitting naked in my rocker. Her legs were drawn up against her chest, her fat little cunt looking straight at me.
“Good morning.” She said with a smile.
I scrambled to my knees at her side. “Good morning, Miss Jenny.”
“You’re getting cuter every day.”
“How are your gums?”
“The new teeth feel okay.”
She stood and pulled me to my feet. She kissed me tenderly and ran her tongue over my gums. “Do you feel any bone spurs?”
“Ann Melon is the best. Whether it come to oral surgery or oral sex.”
I laughed. I didn’t know if I could laugh, but the play on words was funny and there hadn’t been a lot to laugh about lately. I fact I couldn’t remember laughing as a woman.
“Clean your pussy and we’ll shower together.” Jenny said.
She sat on the toilet and watched as I mixed the bag and put the contents in my body. She stood and gently rubbed my tummy while I waited.
“You look like your pregnant.”
“This part hurts a little.”
“Go ahead and dump it.”
While I took the second bag Jenny started the shower. We washed each other’s hair and ran soapy hands over one another’s bodies. I shaved her legs and she shaved mine. I thanked her by cupping her right breast and kissing it. I ran a hand over her soft belly, then ran it down between her legs and cupped her cunny. I was really beginning to feel like a woman, if albeit a lesbian. We dried off, applied lotion, powdered and made a mess, but I was ecstatic.
Jenny selected my yellow bikini top; a white gaff and white low-rise pedal pushers as my outfit. My shoes were white leather thongs with three-inch wedge heels. I had small breasts and my tummy wasn’t flat enough, but I was cute.
After breakfast, Jenny said she had the day off and that she and I were going to the beauty parlor.
I was on a leash when we arrived and I wasn’t at all sure of the protocol for male sissy slaves in a beauty parlor. The women didn’t seem to care and carried on a constant chatter among them. They did ask me for a nail color and after consulting Jenny, I told them I wanted frosted pink. We had facials, manicures and pedicures while they worked on our hair.
It was dark outside when they were finished. Jenny and I were the only customers and I assumed Jenny had some special arrangement. The beautician spun my chair so I could see my new do. Surprise. Surprise. I had short platinum blonde hair with ringlets across my forehead.
“It’s a twenties style. Very in.” The beautician said.
“Thank you.” I almost added Mistress.
As we left the building Jenny asked if I liked my hair. I knew I wasn’t allowed an opinion. I also understood the question.
“It’s just like yours and it’s one of your most beautiful features, Mistress. Thank you for allowing me to have the same style.”
When we got home I made supper without changing cloths. They had pasta primavera and wine. Sheila told me she had made me something special. It was in the black carafe in the refrigerator. I knelt by her chair and poured myself a glass of the liquid. It was yellow. I took a sip. It was piss, but it was very cold and it was hers. I enjoyed two glasses full.
After dinner I cleared the table, put the dishes in the washer and started a pot of decaf. I went to my room and sat on the bed with my knees pulled up to my chest. The day had been confusing and I was trying to sort it out. Over and over I had to admit to myself it didn’t make any difference what I thought about their actions.
Sheila walked in. “Put on your black collar and bracelets, a black garter and hose and your black heels. We’re waiting in the den.” Almost as an afterthought she said, “Leave your teeth here.”
When I arrived my mistresses were seated having coffee. I sank to my knees and awaited their pleasure.
“Hang this in the eyebolt.” Sheila said handing me a lightweight metal spreader bar about five feet long.
Someone had installed an eyebolt in the ceiling, several feet in front of one of the floor to ceiling windows. I got a two-step ladder from the kitchen and hung the spreader bar. I was about to return the ladder when Sheila told me to leave it. The two women walked over to where I was standing and I sank to my knees.
“Open your mouth.” Jenny said.
A small rubber dick protruded from the leather gag in her hand. She put the dick in my mouth and buckled the strap behind my head. She pulled me up and led me toward the spreader bar. Sheila was on the ladder. Jenny pushed my right arm up and Sheila attached my bracelet to the spreader bar. Sheila moved to the other side and they repeated the process attaching my left bracelet to the spreader bar. Jenny attached another spreader to the D-rings on my shoes, pushing my legs apart and suspending me slightly off the ground. My clitty stick, shriveled by hormones, hung limply between my legs.
Armed with long slender leather paddles they began to whip me. They worked on my butt, my piercings, my breasts, my navel, and between my legs. I bit down on the gag and cried. Once I started it was as if I had opened the floodgates. I’d never been one to cry but tears were running down my entire body. The beating was unrelenting. Each contact between the paddle and my flesh sounded like an exploding firecracker, adding an aural factor to my punishment. By stretching I could grab the spreader bar and move my body slightly, but it was to no avail. Blow after blow rained down on my slender defenseless frame until finally, it was over.
As they switched off the last light Sheila laughed and said, “Don’t worry about breakfast.”
Sometime during the night I was released. That exquisite pain at the point my limbs were release must have dulled my recollection of the events. I’m reasonably sure I was given the Toilet command and I hope I did an excellent job. In any event, I was still on the bathroom floor when I heard my mistresses stirring around the next morning. I got up, crawled under the covers on my bed and went to sleep.
It was nearly noon and I was off to a late start, but when I slipped into the tub my body refused to leave. Cleaned and powered and a vision in pink I whirled through my chores and was resting comfortable in my room when Jenny and Sheila got home.
Sheila found a lime green jog bra and a matching pair of long leg tights. She tossed them on the bed along with a pair of socks and baggy white shorts.
“Wear your gaff there are running shoes in the closet. We’re going jogging.”
This was my first time out in our neighborhood as a girl. Jogging with the girls would have been a lot of fun had it not been for the leash. It was only four blocks to the park. The weather was cool and the breeze up my shorts was a totally new sensation. The jogging path through the park was paved and bathed in the afternoon sun. It attracted a lot of our health-conscious neighbors.
I expected my condition would attract a lot of attention, but the attraction was an old one, three young women. The hunks would jog past me and compliment my mistresses on her pet. Then they would ask if I did any tricks. The lack of originality was uncanny. I was mortified when Tom Pepper appeared on my left shoulder. He worked for me until I quit and lived two streets over from us. He was tan and beautiful. He apparently didn’t recognize me and ran up beside Sheila.
“Hi, Tom. What’s up?”
“Everything’s fine. How bout with you?”
“Excellent.” Sheila said.
“What happened to Andy?”
“He left me.”
Tom came to a stop, obviously stunned by the news, and then sprinted to catch Sheila. “Why?”
“I don’t know. He quit his job and left me the same day.”
“How strange.” Tom said and then added. “What’s with the girl on the leash?”
“She’s my slave.”
That stopped him again. When he caught us again, he said, “What do you mean slave?”
“I mean she does anything I say, anytime I say.”
“Can we stop for a minute?” Tom said.
Our entourage stopped and Sheila said. “Tom this is my friend Jenny. We call our slave, Sissy. What do you want?”
“I hardly know where to start. Can we talk in private?”
“You and Jenny and I are in private.”
A big fluffy cloud held us in its shadow for a few moments before Tom continued.
“I’ve been wanting to call you. I wasn’t sure about Andy, but if he’s out of the picture, well I was going to ask you out. Of course, that’s before I see you out here with this.” He said, pointing at me. “Are you a dyke?”
Sheila kissed Jenny carefully placing a hand on one of Jenny’s breasts then said. “Sweetheart, am I a dyke?”
They both laughed and Jenny said. “I’m not sure, but I think that only applies if you wear a strap-on dildo while you’re eating my pussy.”
Sheila ran a single red tipped finger down Tom’s chest and said, “You’re real pretty so come over to our house anytime you want and I’ll fuck your brains out, but don’t insult Sissy.”
“Why do you need a slave?” Tom asked shaking his head side to side.
“That’s a good question. Let’s see if I can explain it to you.” Sheila looked around then offered my leash to Tom. “Take Sissy over to that little clump of bushes and she’ll explain it to your dick.”
“No fucking way.”
“Sissy, take your teeth out and show Tom your tongue.” As I did, she rubbed Tom’s crotch.
“You bitches are sick.” He shouted as he ran down the path in the opposite direction.
I put my teeth back in and we finished our run with only an occasional catcall.
When we got home I cleaned up, put my uniform on and made dinner. After dinner, I cleaned the table and did the dishes while Sheila and Jenny got a bath. They emerged wearing cut-offs, tanks and flip-flops.
“Let’s go for a little ride.” Jenny said, snapping my leash in place.
We drove downtown and cruised the Fourth Street area. There were a lot of girls and guys offering their wares. The storefronts were bright with neon and as seductive as a siren’s song. We pulled up in front of Tammy’s Video Arcade, Sheila handed me an envelope and told me to give it to the man behind the counter. It was only a short walk, but I was in a pink maid’s outfit. Of course, this was the red-light district, and I probably looked more normal than most so I got out.
The young man behind the counter smiled, accepted the envelope, opened it and went about the store collecting items. When he returned he had:
Two hot pink dildos (approximately
8″long and 6″ around)
Three butt plugs:
He laid the items on the counter. Every guy in the place was looking at me. “Do you need anything else, little lady?”
Little lady, I thought, but I said. “No thank you.”
He rang up the items, made change from money in the envelope and put everything in a plain black sack. Then he handed me a note that said I would give him a blowjob. I put my teeth in the bag, went behind the counter, got on my knees and unzipped his pants. My only thought was to get it over. Everybody in the store and everyone walking by could see me. That included Sheila, Jenny and any cops that might wander by.
When I got his dick out I changed my mind. It was thick at the base, uncircumcised and had a very small head. It resembled an ice cream cone with the point toward my mouth. I unbuckled his pants, and pulled pants and shorts down so I could get a better look. His big balls hung down in a long sack. I picked one up and put it in my mouth. The cone stiffened. I dropped the balls and slide the cone into my mouth. He responded to my tongue and ball, but I already had my nose in his pubic hair. It was a strange feeling as I withdrew. I sucked back and forth a few times. When he put his hands on my head I slipped I frosted pink finger into his ass and he came. It wasn’t a flood but I had to swallow twice to get it all down. The flavor was fabulous.
I left him standing there with his pants around his ankles, picked up my bag of goodies and ran to the car. As I got to the car, Sheila kept pulling forward a few car lengths at a time. I was running as fast as I could in my heels. Jenny was laughing and waving and then they were gone.
Standing in the middle of the street I jumped up and down in absolute rage, followed quickly by stark terror, followed by tears. In retrospect, there may have been some humor. A transvestite jumping up and down in the middle of the road on Fourth Street dressed in a pink maid’s outfit. It was a very bad area. Several store fronts were boarded up, others had iron bars in their windows and doors. Two winos were huddled by a short brick wall sucking on paper sacks. The traffic cruised by slowly. I felt like a porterhouse steak at the dog pound.
I needed a Kleenex and some pants or even a skirt and a plan. My first thought was that it was a prank; they’d be right back. I walked back up the street and stood by the video store. I thought the cap looked stupid, as if the rest of the outfit didn’t, so I took it off and put it in my sack. I put my teeth in and stood quietly next to the building avoiding eye contact with passersby. I didn’t have a watch so I had no sense of time, but I became convinced they weren’t coming back.
My next thought was a taxi. I needed some money. There was money in the bag. It turned out I had forty-three dollars and some change. I needed a phone. I knew the video shop was a bad idea. There was a well-lit convenience store at the end of the block. I decided to try it. The attendant was behind a bulletproof glass partition. He wouldn’t call a cab, didn’t have a phone book and wouldn’t give me any change unless I bought something. I hadn’t smoked in six years, but I bought a pack of cigarettes, a lighter and a cup of coffee. I walked outside, lit a cigarette and called information. I didn’t have anything to write with, but the operator dialed the number for me. They said there would be a cab in twenty minutes. I leaned against the wall, smoked my cig and drank my coffee. It ran through my mind that a lit cigarette was a weapon of sorts.
A car with three young men pulled up and asked me what I was doing. I said I was waiting on a ride. The driver got out, walked over and stood within inches of me. He hooked a finger in one of the D-rings on my collar held a hand on his crouch and said, “I’ll give you a ride.”
I took a drag on my cigarette and it came to me. I whispered. “I’m a vice cop you dip shit. Slip me twenty bucks, get in your car and get.”
He stepped back, looked around and reached for his wallet. He handed me a twenty-dollar bill, I kissed him and he hauled ass. I’m amazed my heart didn’t burst, but I’d pulled it off. The cab arrived a few minutes later and took me home. The meter read eighteen dollars and seventy-five cents. I gave the driver my friends twenty and the rest of the cigarettes.
Mistress Sheila answered the door with a scowl, “What the hell happened to you?”
I couldn’t believe my ears, but I decided I better play along. “I got lost, Mistress. I’m sorry.”
“How’d you get home?”
“I took a cab.”
She took the bag out of my hand and looked inside. “If you spent any of my money because of your stupidity, I’ll take it out of your ass.”
“Just some cigarettes, Ma’am. I bought him some cigarettes.”
“More likely you sucked his dick you little nympho. You ever heard of AIDS? If you introduce AIDS into this family you’re dead.”
“I promise I didn’t touch him.”
“Go to your room and get ready for bed. I’ll be there in a minute.”
I put my uniform up and rinsed my underwear. I removed my tampon, put on a gown and cupped my sensitive little breasts in the soft soothing material. I had a handful on both sides. In addition to the implants, I was sure they were growing. I washed my face and sat on the bed waiting for Sheila.
“Your five dollars short. Stand up and show me your tits.”
I was facing her. She attached clamps to my nipples and unscrewed the stop screws. The jaws were directly over the shafts of my barbells. My nipples screamed in pain. I was sure the pain would subside, but I closed my eyes and clinched my jaw. Sheila slapped me across the face.
“Pay attention, bitch. Pull up your gown and bend over the bed.”
She had a long slender cane. I heard the swooshing and when it ended, any thought of the pain in my nipples passed. The cane had taken a long slender bite out of my flesh and it fell four more times before she stopped. She left the room and returned with a thick salve, which she used to trace the path of the cane.
“You’ll have some great welts, but don’t worry they won’t scar. Turn around and let me see your breasts.”
I complied. She removed the clamp from my right breast and dropped it. It dangled from my left breast by the chain. She rolled the right nipple between her fingers and smiled. She deserted my right nipple and released the left one. The clamps clanked to the floor and she rolled my left nipple.
“You love the pain, don’t you?” Sheila asked.
“Then why is your clitty stick twitching?”
I didn’t have an answer. She told me to sit down and I did, but I immediately wished I hadn’t. She pulled one of the rubber dicks out of the sack and handed it to me.
“I want you to practice sucking this little darling and taking it deep down your throat. Saturday morning, I want you to demonstrate your abilities for us. As for your butt plugs, I’d wear this one tonight.” She handed me the pink one.
I stood, bunched my gown around my waist and put the plug in my mouth. The plug was smaller than a turd and wet with my saliva, it moved easily inside me. I dropped my gown and sat back down.
“Even I’m amazed at how obedient you are. I didn’t mean right this minute, but that’s fine.”
“In the morning, while you’re in the tub, I’d insert this one.” She handed me the purple one. “Anytime you have a plug in you, you don’t have to use a tampon. By Saturday I want the black one in you. Is that clear?”
“Yes, Mistress.” The purple one looked smaller than Alex, but the black one looked impossible. Still I’d given her the correct response. She turned and left the room.
“French toast in the morning.” She said over her shoulder.
I wanted some extra time to soak in the morning so I set my clock for 4:30, turned off the light and settled into bed. My teeth were on the nightstand. The head of the dong slipped easily into my mouth. It had an unpleasant chemical taste; still I pushed it slowly deeper. I suppressed my gag reflex, but as the head entered my throat it was too large to continue. I tried to flatten my tongue, but it didn’t help. I didn’t know if my throat would stretch or tear, but I did know what Sheila would do so I shoved hard one more time. The head of the thing slipped down my throat for a moment, then popped back out. It would take some work, but my throat was okay and I could get it down.
Stinging welts and visions of a plunging phallic made for a restive night. Fear of the new day woke me early.
The next morning I pulled off my gown. The welts were angry, but hadn’t bled. I pulled the butt plug, douched and shaved. The tub was wonderful. I just soaked for about ten minutes and rubbed my wounds.
I tried the purple plug and it went in easily, so I decided to try the black one. I couldn’t get it in. I couldn’t even get enough leverage to push hard. I got on my knees with the plug on the floor of the tub behind me and started easing down. I couldn’t get close. I pulled up then pushed down again. If I moved down another centimeter it felt like my asshole would tear in a hundred places. I jumped out of the tub, smeared my pussy with petroleum jelly and tried again. On the third push, down it felt like it was going. I pushed one more time, there was a massive stab of pain and it popped into place. I rested for a moment and the pain subsided.
I decided to leave it in place while I shaved my legs and did my hair. When I got out of the tub, my ass seemed bigger and I had an unexplainable desire to swing it. Since the plug didn’t hurt, I left it in place in lieu of one of my constant cotton companions.
I powdered my body and slipped on my corset. My natural breasts were peaking around the edges of the cups. This realization ran a tingle down my clitty stick and that tingle reminded me it had been weeks since I’d had an orgasm. It had been weeks I hadn’t had one and I hadn’t died. Maybe an orgasm just wasn’t as important as I’d always thought. I finished dressing and locked my collar and bracelets in place.
Sheila and Jenny came down together and seemed to enjoy breakfast.
“Show Jenny your ass.” Sheila said.
I faced away from Jenny, pulled down my panties and bent at the waist.
She traced a long slender finger along one of the stripes. “Impressive job, Baby.” She said to Sheila. She tapped the butt plug with a red tipped finger. “That’s a pussy full isn’t it, Sissy?”
“She’s got the black one in her.” Jenny said, to Sheila.
“She’s become quite an over achiever when it comes to doing my bidding.” Sheila said.
As Sheila left for work she gave me a list of additional chores and instructions for a large dinner. “There’ll be eleven for dinner. Wear your black outfit and be ready at 5:00.”
My mistresses were home shortly after 5:00. They were satisfied with my preparations and with me. They scurried back to their room to change for dinner. They emerged in the same outfits I’d seen them in that first day.
Sheila was in the white on white brocade corset, her breasts billowing over its top. She wore no panties and her hairless pussy lips pouted out beneath her flat belly. She wore white stockings and white sandals with 4″ spike heels. Her nails flashed red. Jenny wore her black leather waist cincher. The rings in her nipples were joined together by a heavy chrome chain. Black leather garters hanging from the cincher supported her black fishnet hose. Her polished black, high-heel boots were laced up to just below her knees.
The guests were couples except for Alex. They wore skimpy leather outfits (except for Alex) and the women were obviously dominant. I showed them to the dining room and served the wine. Dinner consisted of shrimp cocktails, chicken cordon bleu, Julianne potatoes and chocolate cheesecake. The conversation was polite and topical. I was a real French maid and nobody seemed to give me a second thought. After dinner Alex and the women retired to the den for brandy and cigars. The rest of the men sat at the table and chatted quietly over coffee as I cleared the table and loaded the dishwasher.
“Sissy, you and the boys come here.” Sheila said.
We obeyed. At her command, using short pieces of chain, they attached my shoes to the spreader bar. Then they hung me, head down, from the ceiling in front of the window. Using two more short pieces of chain they attached my bracelets to the spreader bar so that my back was down and parallel to the ground. A slight push caused me to swing. My cap fell off.
There was a sheet over an easel in one corner of the living room. Sheila removed the sheet and said, “Okay ladies, this is a Toulouse-Lautrec lithograph. It’s worth $1,500.00 and goes to the winner of tonight’s contest. Since Jenny won’t be competing, she will be the judge — the final judge.”
She moved away from the easel and continued. “The rules are simple. You will get your man hard any way you can, let him fuck you and fill you up. As soon as you can, you’ll walk over and position Sissy between your legs so she can suck your cunt clean. If you come while she is down on you, that turn is forfeited. Then you go back and get your partner ready again. The teams will start on fifteen-minute intervals and each team will have one hour. The team with the most trips to Sissy’s mouth wins. In case of a tie there will be a fuck off. The males will fuck Sissy in the mouth. The quickest to come wins. Again, Jenny will be the judge. Any questions?”
There were none and she walked over to me. “Open your mouth.” I did and she took my teeth.
It took Jenny a few minutes to get the teams on paper. The first cunt was clean-shaven and sported a gold ring around its clitoris. She was on me ten-minutes after Jenny said go. I sucked out three good globs then tried to hook my tongue ball inside her ring. She pushed me away. Jenny was suspicious and wouldn’t let her leave until she pushed a finger up her cunt. It came out wet, but Jenny was satisfied so she let her go.
My second pussy was covered in soft blond curls. My third was a thick musty black bush. The forth was my Mistress, fat and full. The last cream-filled delight was topped with a short heart-shaped brown mat. Mistress Sheila and the blond give me three loads and tied for first. My face was a wet sticky mess. Jenny took a damp cloth and cleaned me up. She even gave me a little peck on the cheek.
Blondie’s man was short and thin, but his cock head was nice and fat. I worked his underside with my tongue then sucked him down my throat. It was to be his fourth orgasm in an hour and a half, but with my gums and tongue on his shaft and my sucking throat, I got him there.
Alex was hard as a rock and ready. I was in a perfect position to take his big bad beauty. He slammed his rod down my throat, pumped me hard about a dozen times and dropped his load. No contest, Sheila kept the lithograph. While I remained hanging near the window, each of the losers beat their men. Everyone but Alex bid my mistresses goodbye and left. He took me down like I was a feather, sat me on the couch then kissed Sheila goodnight.
As soon as I could stand, I started cleaning the place up. Sheila unlocked the tiny locks on my wrists and neck.
Jenny was hot to trot and tugging on Sheila as she said to me, “We’ll have bagels and juice in the morning. Clean yourself up, but don’t get dressed until after breakfast. We have plans for the morning.” With that they bounded up the stairs, undoing clothes as they went and fell into bed together. I heard them giggling and carrying on for the next hour.
I try to be grateful for each new day, but Saturday’s had been pushing their luck lately. I douched myself and got in the tub. First things first, I greased my tiny hole and started working the black monster inside me. I ultimately had to sit on it again, but in it went. I shaved my legs and carefully inspected my body for unwanted stubble. I lay back in the warm scented water with my eyes closed and contemplated the dildo. I opened my mouth, reached over the side of the tub, picked up the phallus and pushed it home in a single smooth thrust. My throat no longer balked at such an intruder. I leaned back and moved the hot pink lover in and out. Satisfied I could handle my assignment for the morning I stepped out of the tub and dried off. I put on my collar; bracelets and shoes then went to the kitchen. I barely had the table set and breakfast laid out when Jenny appeared.
“I need to pee.”
We went to the bathroom and assumed our positions, but this time was a little different. The golden juice was the same but when Jenny finished she nuzzled my mouth.
I started work on her clitoris. I trapped it between my gums, sucked a vacuum around it and flicked it with my tongue. She moaned and dug her fingers into my hair. I released her clitty and drove my tongue deep into her vaginal opening. She arched her back and tried to maneuver back to the previous position. I tried to rub her engorged little bead with my tongue ball and heard the faintest, “Please.” I returned to my sucking and flicking. She grabbed her nipple rings and pulled as she reached the crescendo.
“Oh my fucking, God.” She said. As she stood, she looked at me and smiled. “Nice. Very nice.”
I took a moment to brush my teeth and ran back to the dining room to find Sheila and Jenny enjoying breakfast.
“Let’s see the plug.” Sheila said.
I faced away from her and bent at the waist.
“Sit at the other end of the table and deep throat the dildo while we eat.” Sheila said.
I provided the entertainment and they enjoyed a leisurely meal. I served coffee and cleared the table with the fake dong hanging out of my mouth. Afterwards, Jenny took me to my room and selected my outfit. I wore a white gaff. The full back panties were a delicate white lace. The bra had delicate straps, a single back closure and similar lace on the cups. The fibers of the knit tank top were dark blue, but the sleeveless top itself was virtually invisible and so short it barely covered my bra. She selected a short, dark blue pleated skirt.
“You may replace the plug with a tampon, if you wish. Your collar, bracelets and shoes are fine. Don’t worry about makeup. Okay?”
She kissed me lightly on the cheek and said, “Get a move on.”
I was waiting in the living room when they arrived. Sheila attached a leash and we were off.
I’d been getting laser treatments almost daily since we returned from Bangkok and despite my light-colored hair it didn’t seem like I was much less the ape. It was certainly no surprise when we parked in front of the beauty parlor. Jenny ushered me back to a private room and left me. I few minutes later, Hilda, a bulky woman in her mid-forties came in and grunted her normal greeting.
“Oh, you.” Hilda said.
She setup her equipment, then looked at my face through a lighted magnifying glass.
“Your face is actually getting there.”
She worked in fifteen-minute sessions, without saying a word. Between sessions she left the room and I was offered a cool fruit punch. It may’ve contained some rum. Regardless, it was good and I appreciated the break.
It was well into the afternoon when she said, “That’s all for today.”
She cleaned my face and applied a sweet-smelling cream then turned and left the room. Jenny had left me a note instructing me to get a cab home. There was money in the envelope with the note. It was very unusual; she had always picked me up after the previous sessions.
When I got home I found another note, and a key to my tiny padlocks. Sheila and Jenny had gone to a convention in Las Vegas and would return Wednesday. I was never allowed questions, but I knew Jenny was an anesthetist. I assumed the trip had something to do with her work although that wasn’t the only possibility. She and Sheila and several of their female friends had formed a coalition of sorts. There were some sexual aspects to the association, but they also shared professional services and networked with other women. That alliance might have been the catalyst for their trip.
The note indicated a Mistress Donna would be checking on me each morning. I was not to leave the house and not to masturbate. I could expect visitors at any time and if they had a key, I should treat then as my mistress or master. To me it seemed like a short vacation. I removed my collar, bracelets and shoes. I made myself a scotch and soda, slipped into my gown and settled into a big leather chair to watch TV.
I was startled into awareness early the next morning around 4:30. I’d fallen asleep or more accurately stated past out in the chair. Thank God, I hadn’t overslept. I decided to stay up and have a leisurely morning. I lay on my tummy in the bathroom, cleansed myself and inserted a tampon. After my bath, I powdered my body. I had a clean feminine smell. My body was round and smooth, my waist noticeable smaller. There was little muscle definition if in fact I still had muscles. I hadn’t picked up anything heavier that a skillet since I started on hormones. My face wasn’t as swollen as it had been in the past and I was anxious to see a baby faced me.
I was properly dressed in my pink outfit, drinking my breakfast. I never heard Mistress Donna enter the room.
“Well, well. If it’s not the pussy boy.”
I whirled to face her and said, “Yes, Mistress.” I quickly dropped my eyes and fell to my knees, but I saw enough to recognize her as Blondie from the party.
“I’m told you are very obedient.”
“Stand up and pull down your panties.”
I did as she instructed. She walked around behind me and gave my tampon cord a light tug.
“It’s my time of the month too, but you’re fine. Pull up your panties and sit over there.” She pointed to a chair at the head of the table.
“I know you’re a cuckold, but I’m told you’re also an able toilet slave. Let’s find out.” Donna said.
I got up and headed for the bathroom. She followed a few steps back and watched as I made my pallet, removed my teeth and lay on my back awaiting her pleasure. She discarded her shorts and pulled down her panties. I noticed the panty liner, but I didn’t see the tampon cord until it was in my face. I remembered her soft golden curls as she pushed them against my nose. The stream of pee was strong and very hot. I had no time for anything but the task at hand so I gulped her down and kept gulping until the stream stopped.
“Well done. Now eat the pussy.”
I’m not sure I could separate out a taste for the menses, but her gash had an oily slickness to it and an especially musky aroma. I took a long lick of her labia, and then plunged my tongue deep inside her. I could feel the cotton cylinder with my tongue. As I returned to licking her clitty I shoved a finger into her asshole. Only seconds later she screamed and clamped my head between her thighs. When she stood she picked up a camera and snapped a photo of my face.
“I’ll drop this on the net to Jenny. She’ll be so proud of you. She’s a big believer in sex during menstruation you know.”
“No, Ma’am. I didn’t.”
“I need a new tampon. Where do you keep them?”
I pointed to the drawer and she found a tampon. I got to my knees and watched as she placed her left foot on the commode. She pulled her tampon out and handed it to me. Her long smooth legs were a sight to behold. She unwrapped the new insert, swirled it in my mouth, spread her outer lips with her left hand and pushed the outer tube inside her body. With her right index finger, she pushed the absorbent pod home and then she pulled the empty tubes out of her body and handed them to me. The cord hung lazily between her lips.
“See yah in the AM, Sweetie.” She said as she left.
In the mirror I watched as I brought the spent tampon to my coated face. To kiss it or to taste it, I wasn’t sure. I reached inside my panties for my clitty stick then nearly jumped out of my skin.
“Just throw it away.” Donna said sticking her head back into the room. “Or I’ll have to tell Jenny you were sniffing tampons and masturbating.”
I fell at her feet and said. “Please don’t, Mistress. Please, you can’t imagine what she would do.”
“Just get cleaned up. I scarcely see a reason to bite the girl that eats me.”
I wrapped the tampon and tubes in toilet paper and put them in the wastebasket. While I was washing my face and hands Donna left, but over the next few days I felt as if I were working with the sword of Damocles over my head.
When my mistresses returned Wednesday night I had made a little Welcome Home sign and a pear and gelatin dessert. Friday morning Sheila told me that some of the girls would be over that night. They would want dessert and coffee at 7:00. She added that some of the boys would be delivering a load of equipment that afternoon. They would put it in the den and I was to leave it alone.
That afternoon Jenny helped me with my outfit. She started with an additional item. It was a white leather garter belt that laced in the back. It fit snuggly accentuating my slender waist and had D-rings sewn into the sides. We added white hose, white heels as well as the mandatory collar and bracelets. She offered no gaff so my tiny dick hung limply between my legs.
Next she sat me on the bed and removed my earrings. She had a chrome plate with two small screws welded to it. She pushed the screws through my ear piercings. She had another plate with a six-inch chain hanging from it. The screws in my ear fit through holes in the second plate. Small thumbscrews connected the two plates with my earlobe trapped between them and the chain brushing my shoulder. With that ear finished she duplicated the process on the other ear.
“You should replace your tampon with that black butt plug and use a lot of lubricant.”
Sheila and Jenny wore light cotton sundresses with spaghetti straps. Neither wore underwear. Both wore low-heeled leather thongs. As the other women arrived they were also dressed in light summer dresses and open-toed shoes. This turned out to be the same women that had attended the last party, a set of regulars if you will. The six of them sat at the table and ate strawberry shortcake with their Irish coffee. There was a constant prattle till about 8:30, when Jenny suggested they retire to the den. Everyone but Blondie had brandy. She wanted a Tequila shooter. They all smoked fat black cigars. Sheila invited me to join them for a drink and produced a large martini glass full of a gray slush. It was very cold, almost frozen.
“Bottoms up, Sissy.” Sheila said. “Compliments of the sperm bank.”
As I began to drink she added. “They don’t know where it came from, but they guarantee it is disease free.”
It was very tasty and a tummy full. As I finished it off they uncovered one of the items the guys had delivered earlier. It was a padded table with one step on the end.
“You need to kneel on the step, Sissy.” Jenny said.
I complied. She placed a rubber block between my knees and tightened a wide nylon strap over the calves of my legs and the block. I was spread and restrained. Adjustable nylon straps on the side of the table attached to the D-rings on my garter belt and pulled me face down on the table. Another strap was tightened across the backs of my legs.
Two of the other girls rolled a power unit into position between my legs. It attached to the step I was kneeling on with turnbuckles. They turned the power unit on and an arm began to piston back and forth. They adjusted the turnbuckles and when they were satisfied they removed my plug and put a dildo on the front of the arm. They pushed the head of the dildo into my pussy and sat back to admire their handiwork.
Sheila said, “Tonight’s contest centers around one of our favorite things, an orgasm. We will each fill out an estimate of how long it will take for Sissy to have one. The prize is a full body massage at Tike’s. After the longest guess is reached, if she hasn’t had an orgasm, that person wins and we will shut off the pleasure machine. As always, Jenny is the final authority.”
After Jenny got all the bets down, they flipped the first switch and the dildo began a deep vibration. The second switch caused the dildo to slowly rotate. Jenny squirted some lubricant on the intruder and flipped the final switch. The dildo started into me. It had a slightly curved tip and rotated so it eventually found my prostate. The direct stimulation took me near the edge of an orgasm before the tip rotated away. Anticipation helped as the dildo rotated into the proper place a second time. My clitty stick stiffened, when I climaxed I shot ejaculate directly on to the block between my legs. Jenny scooped up a glob and dropped it on to the dildo. The pleasure machine pushed the semen into my pussy. Jenny walked over and shut off the machine, but left the rod inside me
Pussy Ring won the massage with an estimate of four minutes, but I was the real winner. I’d had a powerful vaginal orgasm. My body had learning a wonderful new trick.
When Jenny approached, I assumed it was to release me. Instead she secured my wrists to the D-rings on my garter belt, removed my collar and buckled a strap around my head just above my eyebrows. She attached adjustable nylon straps between the D-rings on my headband and the D-rings on my garter belt. The process pulled my head back and prevented side-to-side movement. She walked around the table adjusting and tightening. When she was satisfied I couldn’t move she slapped my ass with her open palm. It left a nice red print and set off the equivalent of a feeding frenzy. Every girl in the place hit me at least once, each trying to outdo the last.
Meanwhile, Jenny had moved a second power unit to the front of the table. She secured it and adjusted the turnbuckles. The arm moved in the same manner as the one in my rear, but had an adjustable angle of travel. She watched the motion for a moment and set it to her satisfaction. She attached the chains dangling from my ears to another set of turnbuckles on the machine. The process set the distance between my mouth and the machine. Then she attached a transparent plastic tube with a solid round end to the arm. The tube was the size of a quarter. Inside the tube were five red balls. The balls were slightly larger than the inside diameter of the tube. She pushed down my chin, removed my teeth and laid four inches of the tube in my mouth.
Sheila explained the contest. “This time we will bet on how many of the balls Sissy can get down her throat before she has an orgasm. As a tiebreaker, we will again estimate the time to ejaculation. Any questions?”
When there were none she added that the prize would be another massage and asked Jenny to start.
Jenny whispered in my ear, “If you don’t get a least three balls, I’ll show them how the front door bell works.”
She started the front unit first. The tube ran smoothly down my throat. The angle of the machine and my throat were well matched and I had no gag reflex. All the balls were inside my mouth as the tube moved well down my throat. I could breathe; everything seemed okay so all I had to do was try to handle the balls. The rear machine started and just my luck, it was on my prostate.
I bit down on the tube behind the front ball. The combination wasn’t good. The tube was slick. My gums were slick and there wasn’t enough room between balls. On the next outward pass, I bit the ball as close to center as I could. It worked. It dislodged the front ball from the others. On the next pass, I bit down hard on the tube and moved the ball a couple of inches. My next effort pulled it to the end of the tube.
My pussy was tingling and that tip was coming around. I now had a ball running in my throat all the time and that added to my sexual excitement. I was working on the second ball when Jenny put her hand on my throat.
“Come feel this.” She said.
One at a time they placed a hand on my throat. They could apparently feel the ball moving in my throat. I had my own problems. I bit the hose as hard as I could and shut my eyes as the tip of the dildo danced on my prostate. The urge passed, but I wasn’t sure I could resist another. The second ball was loose and I moved it into place on the next pass. The girls all shouted two. The tip was coming around when the third ball came loose. I bit for all I was worth. The ball hit home, the tip hit home and I shot my wad in perfect unison.
Everyone had guessed three balls. Heart Shape was closest to the time.
Jenny began shutting down the machines and releasing my bonds. Standing close she said in a low tone, “You’re a lucky girl.”
I remained in my outfit, cleaned up as best I could and served everyone another drink. Sheila insisted I join them. The gray slush not only tasted good, it soothed my throat.
Jenny followed me to my room to help me with an outfit for the morning. “Let’s get theses off.” She said removing the plates from my ears. She installed my normal jewelry in their place. They had given me diamond studs for my top holes, delicate silver rings for my middle holes and three-inch silver hoops for my bottom holes.
Jenny reached under my bed, handed me a box with a big red ribbon and said. “Here’s a little surprise for you.”
I sat on my bed and opened the present. It contained panty and bra sets. The bras were front closure, under-wire with see-through cups and delicate lace piping. The panties were my first T-backs. They had see-through front panels and matching piping. The flimsy panties puzzled me. They didn’t come close to covering my gaff, but mine was not to reason why. There were two sets in white, two in black, one in midnight blue, one in red and one in yellow. Each set was tied in a silk ribbon of a matching color.
While I was opening my gift, Jenny selected a yellow sleeveless tank top made of a wide mesh and a low-ride yellow mini-skirt.
“In the morning I want you to wear these with your white collar and bracelets your white gaff and the yellow undies.” Jenny said. “These will look good on bare legs.” She handed me strappy sandals with four-inch heels that would lace half way up my lower leg. “Put your yellow ribbon in this.” She handed me a small shoulder bag in the shape of a sunflower.
“Oh, Mistress, my first purse. Thank you. Thank you, for all these beautiful things.” I wanted to kiss her, but dared not. When I opened the purse, I found a tampon, a lipstick, a compact and a tiny lace handkerchief. As she left she told me to serve a continental breakfast the following morning and that we would be going to the tattoo shop after breakfast.
My morning began as usual. For breakfast, I served croissants with real butter and orange marmalade. I substituted Mimosas for orange juice and brewed coffee with chicory.
Sheila and Jenny loved my meal, were in a festive mood and planned to go to an Italian art festival after they dropped me off at the tattoo shop. Shelia gave me an envelope and told me to take a cab home. They would see me that evening.
“Hello.” Jack said as I walked into his shop. He locked the door then said. “Take your skirt, panties and gaff off and lay down on the table.”
He restrained and spread my legs then got down between them and inspected the mysterious rings.
“Excellent.” He said. “First I want you to push your testicles up inside your body. Then I want you to grab your dick and ball sack from behind your leg and pull them back between your legs.”
He opened my purse, took the yellow ribbon out and started lacing it through the rings on each side of my scrotum. When he finished I was laced up like a shoe, effectively securing and hiding my clitty stick.
He removed the restraints and said. “You can let go and stand up.”
It was a most remarkable feeling of freedom. Nothing was hanging between my legs. I did a couple of deep knee bends to test the feeling. It was a miracle. I scampered over to a mirror. A neat little bow sat atop my puffy little pussy. I would never be the same.
“Can I put my panties on?” I asked.
The front panel reveled the bow and my pussy. The T-back framed my beautiful ass. I was giddy. I ran over to Jack and flung my arms around his neck. “Thank you. Thank you. Thank you.” Without thinking I kissed him on the lips. It startled us both. He held my shoulders and slowly pushed me away.
“Go lay down on the table. Face up.”
I was aware he was pulling off his boots and pants. He pulled me to the end of the table and positioned my mouth to take his dick. I removed my teeth and laid them beside me. His cock was very limp. He flopped the head with its metal attachment in my mouth. I was inexperienced, but I knew what he wanted, what he dreamed about. Using just my lips I moved over the sensitive area at the base of his head. I lightly scratched his balls as he grew. The view in front of him had to be exciting, pert tits with nipple inserts, a flat tummy with a navel insert, narrow waist, wide hips, a cute pussy, long slender legs, strappy sandals and beautiful feet with flashing nails.
Once he was hard, I reached behind him and grabbed his ass so I could control the tempo. I moved him in and out slowly rubbing my tongue ball along his shaft. When I reached his tip, I bang his Prince Albert with my tongue ball. It was an interesting sensation for me, probably even more interesting to him. I started to suck very hard and run his head against the roof of my mouth in short rapid strokes. When he started to match the rhythm, I slammed him down my throat, taking his entire length in one stroke. He pushed his tool in and out of me. When the head was in my mouth I sucked as hard as I could, forcing him to push hard to enter my throat. Then I would relax allowing him to drive deep inside me. When he started to breath hard and shorten the stokes, I pushed a finger up his ass and he popped. As he spent himself I held him tight in my mouth. His motion was almost unperceivable, but he moved slightly and climaxed a second time before he fell over on top of me.
“Top ten.” He said as he stood. “You might be a guy, but that was special. I’m going to give you the award.”
“What award?” I asked.
He was pulling on his pants and boots. He came over and positioned me on the table. “Put your teeth in.” He said and then started strapping me down. He tightened two straps across my legs, one across my hips and two across my chest. I couldn’t have moved if he stuck a hot poker up my ass. “You might want this.” He said offering me a stubby penis gag. I opened my mouth and accepted it.
He assembled his tools and positioned a mirror above my tummy so I could see what he was doing. In a beautiful forest green, he tattooed a wreath around my navel. At the bottom of the wreath was a small circle.
I became aware of something burning, but I couldn’t see anything in the mirror.
Jack was apparently finished. He rubbed his hand over my abdomen. “Your body is so beautiful.” He turned his back to me. In a blur, as he turned to face me again, I saw a wooded handle and a long rod. I never felt the heat. “One and two.” He said.
Between the one and the two I endured an unholy searing pain that seemed to last at least an hour. Long before I realized it was coming from me, I heard a blood-curdling scream and a muffled. “Fuck.” There was a vile smell of burnt flesh.
Jack plucked the gag from my gaping mouth and replaced it with a kiss. In just that moment the pain dropped dramatically. I moment later he rose slightly and said. “I know that hurt, but I meant it only as an honor. Nine women and now you wear this tribute. I hope you will wear it with pride.”
“Let me up you maniac.” I screamed
He smiled at me and said. “You need some time to cool down, mentally as well as physically. In a few minutes, I’ll put some ointment on your wound.”
“Does my Mistress know you were going to do this to me?”
“Know. I don’t think so. Sheila will be green with envy. She has begged me for one. All her friends, except Jenny, have been on their knees sucking and begging, but trust me they can’t hold a candle to you when it comes to sucking cock. I’ll tell you something the bitches will never understand. You made the head of my dick tingle. Hell, it’s still tingling.”
My anger had subsided and Jack had applied a soothing balm to the brand. I was still restrained, but I could clearly see it was a fleur-de-lis neatly centered in the circle below the wreath.
Jack finally let me up and offered me a cold beer. I accepted the beer and gave him a flirtatious slap across the face.
“That hurt.” I said.
“Get dressed and I’ll take you home.” Jack said playfully rubbing his cheek, this time he kissed me and he meant it.
When I got home my gown and a video were on my bed. There was a note to make myself a drink and watch the video. I undressed except for my ribbon, slipped on my gown and paddled into the kitchen. I made a large scotch and soda, went back to my room loaded the video and sat in my rocker to watch. It was the session where I was cuckold. At some level, I was ashamed I had so willingly offered up my beautiful wife. On another level, it was just a great piece of porno. There was a stirring in my new pussy as I watched. I had made another drink and reloaded the film when I realized I needed to pee. It was another magical moment, sitting on the pot to piss and reaching between my legs to wipe.
I was on the third run of the film when I heard the girls come clattering in. They came back to my room immediately.
“Let’s see.” Jenny said.
I dropped on my knees in front of them with my knees wide apart and pulled up my gown.
“You cock-sucking whore.” Sheila said. “Get on the fucking rug.”
I raced to my position.
“What’s wrong?” Jenny asked Sheila.
“Didn’t you see her stomach?” Sheila said in a loud, agitated tone.
“She has a new tattoo.”
“Damn it, Jenny. That’s no tattoo it’s his fleur-de-lis.”
“And.” Jenny said.
“And, every woman you know has spent hours on her knees trying to earn that award.”
“And our little girl did. And you are jealous.” Jenny said.
Sheila thought a minute smiled and said. “Yes. Yes, I am and I’m going to beat her butt raw.”
“Beat her if you wish, baby, but not for this. She was only doing what we trained her to do.” Jenny said.
By this time they had made it to the den. Sheila flopped down in a chair and said. “Sissy, get your ass over here.”
I scampered over and knelt by her side.
“Stand up, pull off your gown and put your foot here.” Shelia said to me while patting the arm of her chair.
I stood and assumed the position. She traced her finger over the wreath then touched the brand. I flinched.
“Did it hurt?” Sheila asked me.
“I’m glad. You shameless cock sucker.” Sheila said.
I knew better than to say anything.
She ran her fingers over my new pussy. “That is unbelievable.” She turned to Jenny and said. “Look, Jenny. It’s really good.”
Jenny pushed and prodded at me. “Does it hurt?”
“No, Ma’am. It’s very comfortable. I love it. Thank you both so very much.”
“Rug.” Sheila said, but this time without the rancor in her voice.
“What’s wrong now?” Jenny asked.
Sheila hugged Jenny and kissed her. “Not a thing my love. It was the only way I knew to stop her from prattling on like a teenage girl about her new pussy.” They laughed and hugged and kissed with passion. “Help her to bed and then join me. Would you darling?”
Jenny removed the locks on my bracelets and collar and kissed me goodnight. I slept that night with my pussy laced up, a happy girl.
Monday morning I was told to wear my red panties, bra and ribbon; my white collar, bracelets and heels and a red sleeveless dress. Sheila and Jenny ate breakfast, got dressed and loaded me in the car. They dropped me off in front of the beauty parlor and Jenny said.
“If Hilda finishes today. You should give her a tip.”
I went inside with that disgusting thought rolling around in my mind. Hilda carefully inspected my face and made some minor adjustments. She had me remove my dress and panties, lie down on a table and put my heels in stirrups. She always spent several minutes pawing my body to no purpose. I felt I had no choice. I had to submit, but it was repulsive.
When she started she worked in silence for fifteen-minute shifts. The job progressed more rapidly and with a lot less trauma to my skin than my previous sessions. She removed my ribbon and worked on my clitty stick and ball sack, but the best I could tell she left the slender patch of hair above my clitty. By noon we were finished and I made my offer.
“Ms. Hilda, I’d like to give you a tip, but I’m not allowed to have money. Could I please service your pussy?”
She seemed to expect the question. She unbuttoned her lab coat and pulled off an enormous pair of panties. She told me to lie on the floor and began the monumental job of getting on her knees. When she finally lowered herself on to me my head was engulfed in white flab, bushy black hair and a rank odor. I wanted to gag, but that would’ve been a mistake. Instead I began looking for the knobby little key to my freedom. To my delight she had one and I found it. I worked it over with my newly acquired aplomb. Her orgasm shook my entire body. My face and hair were wet with her fluids. My nose was flooded with her aroma.
“Your handler said not to wash your face until you got home.” With that instruction, she struggled to her feet and left the room.
The woman in the mirror was beautiful, but I felt like a slut. I wanted to be clean. My mistresses and their friends were one thing, but that pig was over the top. Without any options, I set off for home my face painted with shame. The cabby didn’t seem to notice my condition nor was he repelled by my odor. He simply took me home and dropped me off.
Sheila and Jenny were waiting when I walked in, dressed in their corsets and heels. I knelt before them.
Jenny inspected my face and in so doing caught a whiff of me. “That damn Hilda would gag a maggot. Get cleaned up and douche.” She unlocked my white collar and bracelets. “Put on the black set. Wear a black garter belt; black mesh hose and your black heels. You won’t need a plug or a tampon and move your cute ass.” She emphasized her remark with a slapped on my butt.
I bathed and washed my hair — my wonderful hair. It was easy to dry and curl and oh so chic. I powdered all over and laced myself with a black ribbon. My crouch had some blotchy red areas, but my body was beautiful. My weight was at 138 pounds. My breasts were firm, perky and overflowed a B-cup. I was slender with a flat tummy, small waist and long legs. I applied red lip-gloss to my lips and admired my lovely smooth face and incomparable smile.
I was so comfortable; I entered the den with a lilt to my step and dropped to my knees. Doom set in immediately as Jenny began to attach the spreader to my wrists. Sheila and Jenny worked together to hang me to the ceiling hook. Then using two short chains they attached my heels to the spreader bar. I was strung up, belly down. Using small round rings that would hook over my barbells they attached a ten-ounce weight to each of my nipples. I couldn’t believe the intensity of the pain.
Sheila pushed a gel into my pussy and I knew what that meant, the fucking shock machine. Jenny attached the leads to my elongated nipples, put a rubber mouthpiece in my mouth and gave the weights a push. When she tapped the control I lurched, the weights bounced and my back made a cracking noise.
“We’re going to dinner. Our friend will keep you entertained while we’re gone.” Jenny said.
This was my worst nightmare. I could hear the timer running and I was sure to get another jolt any time. When the first one hit it was hardly a tickle. I assumed they were set for random strength as well as random timing. I tried to harden myself for the next big one, but I couldn’t. The timer ran, my nipples hurt and nothing happened. After an eternity, I heard the front door open and my mistresses came clamoring into the room.
Jenny said. “Well Sissy, I see you’re still hanging around.”
Sheila removed one of the weights and said. “Did you enjoy our little joke?”
“Yes, Mistress. Thank you very much.”
She removed the other weight and the electrodes. Between the two of them they got me back on the ground. I fell to my knees as much from exhaustion as from respect.
Jenny said. “Don’t worry about breakfast. Just get yourself off to bed.”
Over the next couple of weeks there was a marked change in our relationship. I did my work, but there were no hassles. I jogged without a leash. I was told to select my own clothes. I did the shopping and ran errands. In short, I was just one of the girls, the subservient one, but one of the girls nonetheless. My life seemed comfortable, perhaps too comfortable.
After two reasonably quiet ones, I wasn’t surprised when, my Saturday started normally. Sheila joined me in the kitchen as I was preparing breakfast.
“Toilet.” She said.
I scrambled into the bathroom, nuzzled her warm box and accepted her golden gift. She finished, but made no effort to move so I started to love on her.
She thumped me on the forehead and said. “Stop that.” I settled down and she continued, still sitting on my face. “Sissy, we’ve completed your physical modifications and we’re satisfied with your attitude and deportment, but I really wonder if you understand how challenging a woman’s life can be? Jenny and I can’t always be there to protect you. I real woman knows how to control a man even when she’s on her knees.” She paused then added. “Maybe even more than ever when she’s on her knees. Do you understand?”
“Yes, Mistress.” I managed. She had moved back away from my mouth.
“You and your cute little voice. You’re such a doll.” Sheila said. “We’re going to give you a little test and I want you to understand you’ll be on your own. You’ll be with strangers and we won’t be able to protect you.”
“Now you’re frightening me.”
She tenderly stroked my head and held my chin up so I was forced to look at her. “That’s the point little girl. If a man finds that thing between your legs he could get violent.”
“Really? I doubt it, but we’re going to find out. Your outfit will be on your bed after lunch. You won’t need your bracelets, collar or shoes. Be downstairs promptly at 1:00.”
“Now get breakfast ready.”
I spent the morning in shorts and a halter doing my chores. I drank my shake for lunch and when I had their lunch on the table, I ventured upstairs to see my outfit. There was a pair of white denim bib overalls on my bed. The legs had been cut off and a transparent plastic sleeve about six inches wide by two inches tall had been sewn onto the bib of the overalls. A colorful sign had been slipped into the sleeve. It was the letter “I” followed by a red heart followed by the picture of a rooster. There was a long slender chain laying on the overalls and a note instructing me to use it and one of my locks to lace my pussy. The chain had a series of small rings along its ends. I powdered myself and got the chain in place. It worked well. The overalls barely covered my nipples much less my breasts. My little sunflower purse was on the bed so I picked it up. As I bounded down the stairs, one could see up my pant legs. My pert tits giggled provocatively under the small bib.
“Are you ready?” Jenny asked me.
I had no underwear, no shoes and unless they had added something to my purse, no money and no identification, but they knew all of that.
“Yes, Miss Jenny.” I replied.
We drove south of Nashville on highway 70.
“Help us pick out a cozy bar.” Sheila said. “I could use a drink.”
As we went blazing by it, I picked the Dew Drop Inn. Sheila found a spot, turned around and went back. She parked in the far corner of the blacktop parking lot and turned to face me.
“We will be back here at 10:00. Any woman as pretty as you should have a wonderful time between now and then.” Sheila said. “Now get out.”
I knew I had no choice and I thought I understood the challenge so I popped out and watched as the car drove off. I checked my purse. As expected I found a lipstick, a compact, a handkerchief and a tampon. I didn’t need to, but I touched up my makeup and headed for the bar. The inside of the bar was as black as a cave and it took a second for my eyes to adjust. There was a couple of old guys at the bar. A clean-cut man with a barrel chest was behind the bar. I went over and took a seat on a tall bar stool.
“Can I help you with something, little lady?” The bartender asked.
“No, Sir. I just need to rest a minute.”
The bartender pointed to a sign over his shoulder that read no loitering then said. “You can’t hang around here.”
“Please, Sir. I won’t cause any trouble. My feet hurt.”
“If you’re old enough, I’ll serve you a drink. You can rest while you drink it.” The bartender said.
“I don’t have any money, but I’ll help you clean up or something.”
The bartender came around and looked at me. “Where are your shoes?”
“I lost them.”
“Lose your bra too?”
“No, Sir. I don’t need one.”
“I think I’ll take you up on that or something. Follow me.” The bartender said.
“The little filly is with me Mike.” One of the men at the bar said.
The bartender gave him a hard look then said. “Okay, Sid.”
I ran over and hugged my benefactor. “Thank you, Mr. Sid.”
“Would you like a drink?” Sid asked me.
“Yes, Sir. I’d like whatever you’re drinking.”
“Mike, give us a couple of draft beers.” Sid said to Mike then turning to me he said. “You’re a polite little filly. What’s your name?”
“Thank you, Sir. My name is Sissy.”
We sat and talked through three of Sid’s four unhappy marriages. I encouraged him to touch me and gave him little peeks at my breasts. Mid-afternoon a few more male patrons drifted in. I had no trouble collecting ten bucks for the jukebox and started an outpouring of country and western music. I had never danced as a woman. I gyrated, wiggled, giggled and laughed. I had never known such fun. I had returned to my seat and was chatting with Sid when I felt a hand on my right breast.
“Hi, Sid.” The tall ugly owner of the hand on my breast said. “Who’s the doll?”
“Hi, Carl. This is my friend Sissy.”
Carl moved his rough hand to my nipple and rolled it between his fingers before whispering in my ear. “I wish I had a little pussy.”
I said. “Don’t we all.” But I doubt he got it, so I added. “I wish I had $50.00.”
He got that real clear. As I turned he removed his hand, looked at my little sign and asked. “What does that mean?”
I pointed at the “I” and said. “I.” I pointed at the heart and said. “Love.” I pointed to the rooster and said. “Cock.”
He was literally vibrating, his voice nervous as he said. “I need to show you my truck.”
When we got to his truck he started fumbling with my clothes. The tampon in my purse and my tongue ball helped him decide on a blowjob. I knelt in the floor on the passenger’s side and placed my teeth on the seat. He put two twenties in my pocket and I dropped my bib so he could play with my tits and barbells. I got his dick out; it was short, circumcised and smelly. He cussed and bounced around as I practically sucked his seed straight out of the sack. It happened so quickly I was out the passenger side door before he could say a word. As I hitched up my overalls I watched him stick his tender dick in his pants. I blew him a kiss and headed for the bar.
Back inside I bought Sid a couple of beers and we covered his fourth uncaring wife. Turned out none of his wives would give him their ass and that was what he really wanted.
“Let’s go in the back room. I’d love to have you in mine.”
He giggled like a schoolgirl and said. “No, I couldn’t. I was just making conversation. Really.”
I French kissed him and rubbed his dick. I felt one of his big rough hands sliding up my leg and across my ass.
“My ass is warm and tight.” I whispered.
Sid stood, said something to Mike and went to the back room. I followed him a few minutes later. He stood and I knelt. I unbuckled his pants and pulled them and his briefs down. He might have been sixty, but he had a gorgeous hairy dick with massive heavy balls. I slipped my teeth in my pocket, held one ball in each hand, then kissed and licked them. He responded and I worked his shaft over with my tongue ball. I don’t believe he’d ever had such a massage. When he was good and hard, I stood and stepped out of my overalls. His eyes were wide with lust. I pulled my tampon, dropped it in the trash and bent over some beer cases. He could see what he had. He touched my clitty stick before positioning his dick at my rectal opening. He was forceful. Perhaps mad with lust or mad because of the deceit, but his cock was exultant. The pounding he was giving me only hastened his climax. He spent himself inside me and collapsed on my back.
“Thank you, Sissy. You’re wonderful.” Sid said.
To confirm his assessment I got on my knees in front of him and carefully licked his cock and balls clean. After I had him tucked away, he watched as I put a fresh tampon in place. It must have been an erotic dream come true. He started kissing my buns, licking my pussy and fiddling with my cord. I relaxed and let him play. He pulled out his dick and started whacking himself off. His desire sated he deposited a load on my backside. He used a bandanna to wipe me clean, kissed my cartouches then turned me to face him. We embraced and he wrapped me in his powerful arms.
“I want you to marry me.” He said. “I have money. I’ll make you happy.”
No wonder this guy had been married four times I thought, but I said. “Thank you, Sid. I’m flattered, but my mistress wouldn’t be too happy.”
This seemed to soften his desire, I got dressed and we returned to the bar. The next few hours sped by. As a male, I’d never been anything special on the pool table or shuffleboard. Dressed as I was, the boys just couldn’t seem to keep their minds on the game.
Every guy in the place made it his job to fondle my breasts. A couple of guys even had a hand inside my overalls rubbing my tummy and navel ring. They just had to see it so I showed it to them.
One of the guys was named Cody. He was tall and slim dressed in jeans and boots. His ass was compact and there was a long fat bulge on the inside of the right leg of his jeans. When I dropped my bib to reveal my navel jewelry, he turned the bill of his ball cap to the rear and kissed all around my wreath. He pressed my pants down, kissing as he went. I let him get as far as my pubic hair before I gave him a love tap and pulled my cloths back on.
I sat at his table and watched him play pool until he went to the bathroom. When he did I was right behind him.
“Can I help you?” I asked him once we were inside the bathroom.
“Probably not.” Cody said with a wonderful smile. “Just here to recycle some beer.”
I grabbed the waistband of his jeans and pulled him into a stall. It didn’t take much effort. With Cody facing the toilet, I knelt on his left side. I slowly unbuckled and unbuttoned his jeans and work them down his legs, that middle leg was stunning. It was about the size of Alex, but the circumcised head was twice as long. I took my teeth out, put them in my pocket and showed my tongue ball. That being my best come hither move. I held his meat in my right hand and pointed it toward the toilet. As the stream poured into the bowl, I ran my left hand through it then touched my wet fingers to my lips.
“Damn girl, you’re about kinky. Aren’t you?” Cody said.
I pointed to the sign on my bib. “No. I just love cock.”
When he was finished, I didn’t shake him off. I just put him in my mouth. The head of his cock was not only long it was spongy. Using my tongue, I pressed it against the roof of my mouth repeatedly. It was like eating soft candy. While I was having a wonderful time, Cody was not. He started pushing with that tight ass. When I opened my throat, he entered and groaned in pleasure. I rubbed the underside of his dick with my tongue ball as he withdrew. As he fucked my face I looked up at him. He had a dreamy, contented expression. Mine would have been the same except my mouth was distended. When his cum started to flow I held him in the front of my mouth so I could wash the fluid around in my mouth and taste every morsel. He pulled out and I showed him my cum-coated tongue.
“I wish you’d take me to the bathroom every time I needed to go.”
As I stood I said. “I’d like that too.”
Cody hugged me and French kissed me. “Thank you, Sissy.”
My feet and knees were black from the filthy floor so I stayed behind to clean up when Cody left. Using hand soap and paper towels I did an acceptable job. I returned to Cody’s table and we played partners pool for $2.00 a stick. He ordered a microwave pizza. We drank, ate and by 9:30 I was up another $40.00. I truly hated to leave. Jenny and Sheila were on time and pumped me for every detail of my adventure. I thought Sheila was going to go back and get her a piece of Cody. When we got home I bathed, primped then joined Jenny and Sheila in the kitchen. They invited me to join them for a Scotch and soda. Sitting at the table no less.
Jenny walked over, stood behind me and massaged my shoulders. “You’re soft as a baby’s butt.”
“Thank you, Mistress.”
“You could make any man happy, but how do you think you’d do in a fight?”
I giggled. “Why would I get in a fight?”
“I’ll see you in the morning, Tiger.”
With that she and Sheila went to bed. I cleaned up the kitchen and retired.
It was almost ninety days after my journey to womanhood had begun when I awoke the next morning to find Jenny sitting in my room, watching me.
“Good morning, sleepy head.” She said in a pleasant tone. “Clean your bottom and we’ll shower together.”
I complied immediately. In less than ten minutes we were in the shower together. I shampooed her hair and then she shampooed mine. She didn’t say a word so, of course I didn’t. I soaped her shoulders and breasts. She turned to face me and reciprocated. I ran a soapy hand across her smooth flat abdomen and down between her legs. She fondled my balls and dick. I stiffened.
“I told you once I didn’t like that.”
I pushed it down. “Yes, Mistress. I’m sorry. Please forgive me.
“Maybe I was wrong.” She said and turned off the hot water drenching us in bitter cold.
Never has a man been so soft so quick, but she didn’t leave. Instead, she splashed around and pushed me under the showerhead. I would have liked to play, but I was unsure of my position so I just moved away and allowed her to push me back. Just short of blue, she jumped out and I followed. We found big fluffy towels and dried off. With towels tucked neatly across our breasts, we stood at the vanity combing our hair. We looked enough alike to be sisters.
She told me to wait and went to her room. When she returned she had an armload of stuff.
“Lace yourself and put this under the laces.”
She handed me an old fashioned sanitary napkin. After I was laced she handed me a white spandex jog bra. I put it on and watched as she put on an identical one herself. Next, we each donned white panties and real boxer shorts. They were white with a black stripe. She had socks and white leather boots for both of us. The boots laced up four or five inches above our ankles. We looked like a couple of female Boxers.
“Leave your earrings here.”
I put them on the dresser and picked up my collar.
“You won’t need that stuff today.” Looking at the clock she said, “Let’s get going. We’re late.”
We drove downtown in silence and parked in front of an old building that had been converted to apartments. We rode a freight elevator to the second floor and entered an enormous room that contained only a prize fighting ring. Sheila, Blondie and Pussy Ring were standing at ringside.
Sheila walked over and kissed Jenny. She looked at me and said, “Hello, Sissy.”
“Are you sure you want to do this?” She asked Jenny.
“Let’s get it on.”
With that the three of us got in the ring. Sheila handed us each a pair of Spandex gloves.
“Put those on so you don’t break a nail or scratch one another. Sissy, this will be a wrestling match, best two out of three. You must pin both shoulders for a count of three to win a round. You may not hit with a closed fist, pull hair, gouge eyes or bite. I will referee and there will be a short break between rounds. Sissy, if you lose this fight, we will go home and play with the doorbell. Any questions?”
“What if I hurt Miss Jenny?” I asked
“If I were you, I’d worry about winning.” Jenny said.
“Go to your corners and come out fighting.” Sheila said.
All I wanted to do was go to my corner and hide. I was in the proverbial no-win situation, but I moved tentatively toward the center of the ring. Jenny was in a crouch moving my way. Before I could defend myself, she kicked me between the legs. The small audience cheered. It really didn’t hurt. My balls were up in my body, I was laced up and I had the napkin. I did instinctively bind at the waist. She grabbed my right arm and spun me 270 degrees into the ropes. When I came off the ropes, she leg-whipped me in the stomach. I dropped. She flipped me over and sat on my face and chest with her back to me. When I tried to flip her off, she cupped her hand and pounded my gut. I think the move was illegal. I heard the referee’s bam, bam, bam and I had lost round one. The girls (all four of them) were jumping up and down, doing high-fives and generally having an exciting time. I found some water in my corner, sat down and took a swig.
I was a bit warier to start round two. I managed to grab her around the neck with my left arm. I rolled to my right, flipping her across my body and hard onto the canvass on her back. I thought I had her, but she pushed my left elbow and slivered away. I was still on my back when she dropped a knee in my stomach. That sat me up; she grabbed my right arm and bent it behind my back. Jenny was kicking my ass and I didn’t seem to have the strength to stop her. She held my arm while she locked her legs around my waist and started squeezing. She has on her side and I was on my back. The pain was intense. She still had my arm. I couldn’t break loose so she pulled it higher and clamped down again with her thighs.
“You want to quit, little girl?”
I tried to shrug her off to no avail. She got two of the fingers on my right hand in each of her hands and started pulling them apart. I wanted to quit and she sensed it. She let go of my arm and rotated up on her knees with my waist still trapped. As she moved to a standing position, my shoulders were trapped. I couldn’t get loose and started to cry. Bam, bam, bam and I lost the match. Jenny relaxed her grip and eased down on top of me.
“Don’t cry precious. It’ll be alright.” Jenny whispered. She kissed me and ran her fingers through my hair. Then she kissed me again. This time it was with passion. She rolled on her side and pushed her thigh between my legs. She wrapped her arms around me and plunged her tongue deep into my mouth. At that moment, I was the most shocked person on the planet. It hit me that I was in love with this beautiful little lesbian and in some bizarre way she loved me. I was going to be abused to the point of death anyway so I relaxed my guard and returned Jenny’s passion.
“Okay you two. Enough is enough.” Sheila said. “Let’s get out of here.”
Jenny was silent on the way home, but when we got there she told me to go to my room, get cleaned up and dress in the outfit on my bed. It was the black collar and bracelets, a black garter belt, black mesh hose and black heels. She also told me not to join them in the den until 5:30, which was over six hours. This was cruel and inhuman treatment. I had nothing to eat and only water to drink. I knew they were going to hurt me bad and I had hours to stew about it. I was stinky so I decided to take a quick shower and try a nap. I did drift off into an anxious sleep, but it was only 2:00 when I got up and found a TV tray with a BLT, chips and a coke sitting in the middle of my room. This new kinder, softer mistress had me off balance.
Time crawled by. I lay on the bed again and thumbed through a couple of women’s magazines. At 3:30 I decided to try the crossword puzzle. I couldn’t spell my name, but I had a dictionary and plenty of time. I was board in ten minutes and quit at twenty.
I removed my toenail polish and repainted them, and then I decided to do my fingernails. Around 4:30 I got in the tub to soak, but I took my mind with me and I couldn’t relax. I washed my hair knowing it would take some time to dry and style. By 5:20 I was dressed and ready to go. I paced the room until the precise time and stepped into the den at 5:30.
Sheila, Jenny and their four lady friends were seated in a semicircle. They were resplendent in cocktail dresses of rich dark colors wine, green, blue, bronze, brown and charcoal. I knelt in front of them. Between us were whips, plugs, the shock machine and the spreader bar.
Jenny started a videotape recorder. I could hear Sheila’s dress rustle as she approached. “We’re going out shortly, but first we have decided to dispose of Sissy. Snuff her out if you will.”
The videotape and the word snuff engendered visions of my body with a bleeding throat. I fell to her feet crying, “Please, Mistress. Please don’t kill me. I’ll be good.”
Sheila removed my collar and kissed my neck. “I’m not going to hurt you, Jamie. I’ve always loved you.” She removed my bracelets and kissed my wrists. “Please get to your feet and meet our friends.”
I looked her in the eyes for the first time in ages. “I don’t understand.”
“It’ll be clear soon. Meet our friends.” Sheila said.
“Make that — Okay Sheila.”
I already knew that Blondie was Donna. Pussy Ring was Kathy. Heart-Shaped was Melinda and Black Bush was Pam.
“Some Champagne Jamie?” Jenny said.
I decided to see what would happen. I looked at Jenny and said. “Yeah, Jenny.”
She kissed me. “Now you’ve got it, baby.”
“Before we have our Champagne. I have a present for you.” She led me up the stairs to their bedroom, the forbidden room, and in we went.
She handed me a brightly colored bag. Inside was a pair of black pantyhose. I removed my heels, garter belt and hose. Then I slipped on the pantyhose. Next, she gave me a shoebox. Inside was a pair of high fashion, black patent heels. They had square toes and rectangular heels. From her closet, she retrieved a black sheath.
“Would you like to replace your Sissy medallion?” She asked as she handed we a diamond stud pin for my navel.
“Boy would I.” I said, but I couldn’t get the job done my eyes had moistened so Jenny helped me. I stepped over to the mirror. My waist was so small my hips looked like they were hanging from a string. The diamond stud glittered like a headlight.
The gown was strapless and had a huge bow in the back. I stepped into it and Jenny zipped me up. It had a built-in bra and the bodice flared up and out from the waist. It was stunning. I was stunning. I was stunned.
She sprayed me with a lovely scent. Then she helped me with an elaborate rhinestone necklace, long rhinestone earrings and a flashy rhinestone bracelet. Then she surprised me again. She dropped to one knee, slipped a diamond engagement ring on my left ring finger and said, “Jamie, will you marry me?”
I just stood there.
She said, “Say yes, silly.”
“Yes, silly.” I said.
She rose, we kissed and hugged. She handed me a similar ring, I dropped to one knee, slipped it on her hand and said. “Jenny, will you marry me?”
“Yes, silly.” Jenny said.
We added some rings and a dressy watch to my outfit, touched up our makeup and joined the other girls in the den.
“She said yes.” Jenny announced, holding up our hands.
Everyone cheered and Sheila handed me a small black patent leather handbag. Donna distributed the Champagne and proposed a toast. “To the union of friends.”
We downed the bubbly and I went digging in my purse. There was a driver’s license in the name of Jamie Jo Moore, sex female, weight 140 and height 6′ 0″. There were a couple of credit cards and $200.00 cash. There was a key chain, lipstick and a compact. Girly stuff yah know.
“Oh, God Sheila. How will I ever thank you?”
“Well, now that you brought it up.” She said with a broad smile. “Let’s talk.”
Sheila told the girls to meet us at Athena’s later that evening. They filed by and kissed Jenny and me and congratulated us. As we touched cheeks and made kissing noises, I couldn’t help but think about kissing them a few nights back a few feet lower. After they left, we sat at the table with a bottle of dry wine.
“This all started several months back. I hadn’t been with Jenny since we got married, but she was here one afternoon and she lit me up. The orgasm was explosive, as it always is with her. Afterwards I was bitching because you didn’t bring me off.” Sheila took my hand and continued. “I don’t know what the deal was with us, but I never got off. Maybe it was too small a dick or too big a pussy or maybe I just didn’t want to be married. Or maybe it was you running around in panties. Anyway, I was unhappy and Jenny doesn’t like men to start with, so we were having an exciting time bashing you.”
Jenny interrupted addressing me. “Darling, I think I should explain the thing about men. When I was twelve, my vile fucking Father started making me suck his dick. When I started to ovulate, he started fucking me unless I was having my period, then he fucked me in the ass. Every night he was on top of me, pounding me with his dick and mauling my tender budding breasts.”
I walked over, hugged her and whispered. “What a piece of shit. I’m so sorry.”
She kissed me and wiped away my tear.
I sat back down and she continued. “Just before my fifteenth birthday I carried a razor blade to bed one night. When he climaxed and pushed inside me, I reached between us and cut him. I didn’t cut it off, but I promise you one thing, he never fucked anyone again. My dear mother got him to the hospital. When she got home she confessed to knowing the whole story. I left that night and have never seen them since. I did literally blackmail them into supporting me until I got out of college.”
“Of course she spent most of her college career between my legs.” Sheila said with a giggle.
“Remind me, please. Where was your tongue during that time?” Jenny jabbed.
They smiled; Sheila blew her a kiss and then continued with her story. “Somehow we got from your tiny dick to the fact that Jenny wanted a baby. I offered your services, but she didn’t want a stud. She wanted me to divorce you, marry her and adopt a family. You can imagine my reaction to children. I who wanted my tubes tied when I was six.”
Jenny picked the story up from there. “We started knocking the pieces around. Sheila wanted some studs. You wanted to be a girl, or thought you did and I wanted a baby. If you really wanted to be a girl, then you and I could live together. Sheila would be free and you could impregnate me. With one more leap we decided you and I could marry and raise our babies.”
Sheila said. “We had Jen checked and found she was a virtual baby factory. We had your sperm checked and you’re virile. During our next strategy session, the big problem seemed to be your commitment to femininity. We thought it was one thing to wear a bra and another thing all together to have real breasts.”
“Jamie, dear. You understand.” Jenny said. “I just couldn’t have a hairy, smelly male in my life.”
“Of course, I understand.”
“Well.” Jenny continued. “We started out with the idea of some tests for you in drag. Then we moved to the thought of feminizing you and humiliating you as a woman.”
“After Jen and I started down that road, I’ll admit I got turned on by dominance. The first time we met with Jenny’s friends, they were full of suggestions. Things I had never dreamed of doing. I was so turned on I creamed in my panties.”
“She did a lot more than cream the first time my friends brought their studs and put a dick in every cavity of her body. You’ve never seen such a sight.”
“Once we had a plan, we committed to a date and began.” Sheila said.
“What would you have done if I didn’t go along?”
“We had some points of no return as far as your feminization was concerned, but I intended to divorce you no matter what. Jen was only going to accept you if you loved being a woman, no matter what.”
Jenny walked over beside me, leaned down, kissed me and said. “I’ve never been hot for a man, but I’m on fire for you.”
“Does that mean I’m going to get lucky tonight?”
“Baby.” Jenny said as she softly touched my cheek. “With the hormones, we’ve had you on that little thing down there is worthless as tits on a boar hog, but I promise you’ll be ready in time for our wedding night.”
“Okay, my beautiful bride to be, let’s paint our town hot pink.”
Our night on the town launched nearly four weeks of preparation for the wedding. We were unable to find a local minister that would marry us so we decided to be married in San Francisco. We also wanted to honeymoon in Maui. The ideal time for Jenny to become pregnant was around July 22 so that became our wedding date. We decided not to concern ourselves about cost and turn this into an event not only for us, but for our friends as well.
Sheila and Jenny arranged to be off for two months. Sheila would give me away. Donna would standup with Jenny. Melinda would serve as Matron of honor. Kathy and Pam would be our bridesmaids. Kathy and Donna wanted to take their slaves. Sheila, Melinda and Pam wanted to pick up partners along the way. That gave us a travel group of nine.
We decided to rent a private jet. We would fly to Frisco the afternoon of the twentieth so we’d have time for a trip to the beauty shop. We would marry the morning of the twenty-second and fly to Maui right after the wedding.
We spent two full days in bridal shops. I saw what I wanted on our first stop, but we visited seven shops and tried on dozens of gowns. Jenny liked a dress like the one I liked so we agreed on hers. We decided that all the other women would wear powder blue cocktail dresses. We spent hours shopping for every accessory and crawled home every night exhausted but happy.
The twentieth finally rolled around. We rented a limo and a small truck for the luggage. We made the rounds picking up our sisters as we went. By the time we got off the ground we were flying and high. Predictably, the first order of business was membership in the mile-high club. We decided we were two males short of a load, so the pilots were pressed into duty. At one point, my bride-to-be was flying the plane while Sheila serviced both pilots. Did I mention Jenny couldn’t fly? Oh, well.
We checked into the Hyatt at Fisherman’s Wharf and decided on a girl’s night out. The seven of us prowled the area and hopped the bars before settling on dinner at The Waterfront Restaurant and Café. After dinner Jenny and I broke off from the group walked by the bay and talked. It was after midnight when we crawled into bed. I was in love in a way I never believed was possible.
We slept late the next morning and ate a light breakfast before heading to the salon. We had manicures and pedicures in silver polish. We had our hair done including color, complete facials and full body massages. Before we left, Jenny arranged for the beautician to be at our room at 8:00 the next morning.
Back at our room I felt like a new woman. Jenny kissed me then said the word I thought I’d never hear again.
I couldn’t believe my ears, but I complied. She sat on my chest and I nuzzled her pussy waiting for my gift when she stood.
“Get up my love.” She said offering her hand. “I thought it only fair that you understand who wears the pants in our family, understand it before we get married. You’re passable now. You could walk out of here and never look back.”
“No I couldn’t. I couldn’t live without you. I adore the ground you walk on. The eliminations from your body taste like ambrosia.” I held her hands to my lips and kissed the backs of each of them. “Your desires are my reason for living.”
She reached down, held my face in her hands and kissed me. “Tomorrow starts forever Darling. Now let’s get you ready for our last fling.”
I used a white ribbon and white silk T-back panties. I didn’t need a bra. My simple cotton dress was lime green with spaghetti straps. My shoes were white leather thongs. I added one ring for fun. When Jenny joined me, she was similarly attired except her dress was a pale orange.
“And we’re off.” Jenny said.
Off, in this case, was The Stud club and a night of gay and lesbian frivolity. At one point, I was a contestant in a girl or boy contest. Six of us volunteered to come up front from the audience. By a show of hands everyone guessed our sex. Forty-four of fifty-three voted I was a girl. It was by far the most lopsided error of the night.
Jenny and the girls started a chant of, “Show your dick.” I thought for a moment I was going to have to. The show and the jokes were a lot of fun, but we turned in early. After all tomorrow was the big day.
I completed my morning cleansing ritual and had breakfast in the room. Jenny had moved down to Sheila’s room for the morning. I showered and shaved being careful not to get my hair wet. I smoothed my skin with lotion, powdered then laced my pussy and stared at myself in the full-length mirror. I grabbed the perfume atomizer, sprayed it away from me and ran through it like a nymph vaulting a stream.
My panties were high-cut briefs covered in lace. My corset was strapless and by the time I got it cinched my waists was at twenty-three inches, our previously agreed upon target. I’d never worn silk stocking before they were delightful. My traditional “something blue” was a fancy garter. I wore low-heel pumps figuring to slice into the height difference between Jenny and me.
I was dancing the Tennessee waltz to imaginary music
when the beautician showed.
“Are you through with Jenny.” I asked.
“How does she look?”
“Like an angel, Miss. She was the prettiest girl I’d ever seen until I saw you.”
I was too overjoyed to speak, but my smile said it all. She applied a little more color and some gloss to my lips, made up my face and touched up my eye shadow. I was to wear an embroidered headband and a two-tier, elbow length veil. She set it in place and coiffed my do. Jenny had borrowed our jewelry from a friend. The necklace consisted of delicate clusters of diamond-encrusted hearts in a fine web of platinum wire. The earrings matched. I walked slowly around the room, looked at my engagement ring and slipped on my Rolex. My gown hung on the door to the bathroom. I touched it. I was sure I’d swoon if I put it on, but it was that time.
The young beautician helped me step into the strapless A-line. It was white satin with white embroidery and a split front overskirt. I thanked her for her help and gave her a hundred dollars.
The nuptials were to be held in a room two floors down. Sheila escorted me down after extolling my beauty to the point of embarrassment. I heard the wedding march, the doors opened and there was wonderland. The room had been made over into a garden including trees. There were baskets of flowers everywhere. The aroma was intoxicating. At the end of a pedal covered path stood my bride. She was more beautiful than Aphrodite and cast an ethereal glow.
Transfixed, Sheila had to give me a tug to move. Slowly we glided to Jenny’s side.
“Dearly beloved . . .”
“With this ring . . .”
“I now pronounce . . .”
She raised my vale and I raised hers. We kissed and it was over I was Mrs. Jamie Jo Wilson. Two hours later we were cuddled together in the back of the plane on the way to Maui, adrift in a sea of love.
We had two suites and two cottages at the Royal Lahaina Resort. Everyone met in our room for champagne. The view was breathtaking and the company charming, but we had other things on our mind.
As we started for the hot tub Jenny said. “Take this.” She handed me a small gray pill and removed my ribbon.
“Is it Viagra?”
“This stuff makes Viagra seem like a sugar pill.” Jenny said.
Jenny began a carefully conceived plan centered on bringing me near a climax then backing off. She slipped me into her mouth and put her fingers inside me. With a slender vibrator, she deftly manipulated my prostate.
We abandoned the tub for lotion and powder and multi-layered chiffon negligees. We sat on the divan, sipped our wine and watched a movie. It depicted a beautiful young transvestite being ravished by her equally beautiful young mistress.
The flickering screen, the moonlit night and scented candles spun an intoxicating web. Jenny’s warm mouth ministered to my nipples and my clitty stick. I was barely cognizant of the movement that put me inside her vagina. The silky folds licked me to hardness, kissed me to climax and absorbed my fluid. I lay spent beneath her. Her kiss was so tender it might have been a last goodbye, but the morning found us in a lover’s embrace.
“Good morning my love.” Jenny said.
“Good morning my most precious bride.”
“How about a little fun in the sun?” Jenny asked.
“Let’s do it.”
I cleaned myself and put a tampon in me before we showered together. Our bikinis were tiny and sheer. We wore pareus in a mock attempt at modesty, leather thongs and big floppy hats. Jenny ran her fingers over my cartouches.
“I’ll have my cartouches done when we return.” Jenny said.
“Do you know what they mean?”
She ran her fingers through my hair. “Are you trying to tell me you’re a natural blonde?” She said and started to giggle.
After a moment it struck me. “Of course, you know.”
“One of them says Jenny the other says Jamie.”
My eyes moistened as we hugged. “I love you, Jenny.”
“I love you too.” Jenny said. “Now shake your bottom.”
We had breakfast with the girls. The big news was Sheila’s new Italian. She said his name was Joseph, but she had nicknamed him Cavallo.
“That’s Italian for Horse.” She smiled and held her hands about two feet apart. “If you know what I mean.”
Everyone roared with laughter and held their hands at various distances apart.
“I didn’t want to distract you lovers last night so I thought I’d give you this today.” Sheila said handing each of us an envelope.
Mine contained a check for $500,000.00. In stunned silence, I handed it to Jenny and accepted the contents of her envelope. It was the deed to the house in Nashville.
Jenny spoke for both of us, offering both items back to Sheila. “We couldn’t accept this.”
“I don’t know why. It was Jamie’s anyway. I just took my cut off the top. Besides, I’ve taken a loft downtown. You’ll need the house for the kids.” Sheila said.
Jenny grabbed Sheila and they danced around the dining room like a couple of brash teenagers. After breakfast Jenny and I walked down to the beach and swam. It was a tender intimate time. We might have been the only people on the planet.
That afternoon we met the girls at the Hard Rock for lunch. They all had male companions and we got to meet The Horse. I’ll have to tell you he was mighty fine looking.
That night we had dinner at The Horse’s hotel. Jenny and I decided to go as man and wife, Jenny as the man me as the wife. It was a hoot. We turned in early and re-enacted the night before with the same result, I put my seed in her body.
Our days followed a similar pattern for the next couple of weeks. We did get up early one morning and take a helicopter up the mountain to see the sunrise. We parasailed and took dinner cruises and walked and swam and made love. One of Pam’s paramours had a villa on the big island, so we all jetted over for a long weekend of fun and great food.
Our last night there was a gala on one of the yachts and we were invited. Jenny and I wore matching outfits of black all nude pantyhose, black one-piece bathing suits, bright multi-colored cummerbunds, black men’s full-dress tails jackets, black patient high-heel pumps and top hats. I figured the men would be all over us and they were, but it was the women that couldn’t keep their hands off us. All in all, Maui and amour made for a memorable honeymoon.
Jenny Elizabeth was born thirty-two weeks after we returned from Hawaii. We experienced the awe and magic that is a child. She became the center of my life and I loved every minute of it. Jenny would feed her late at night and I would rock her back to sleep. I couldn’t feed her but I had two fabulous pacifiers.
Beth was two when Jenny and I chartered a ship to cruise the Greek isles and try for a second pregnancy. Our second daughter, Renee Ann was born eight months later. Jenny didn’t want any more children. As a matter of fact, she had tired of copulation and our relationship had reverted to form. She was a dominant and I her submissive wife. I gave her pleasure on demand and received little in return, but we were inseparable companions and friends. She worked and planned our life. I spent full time taking care of the children and the house. I found I loved our gardens and spent time almost every day working in them. Our life was fantastic.
These days we see Sheila and the gang regularly for sex and for fun. They are all like Aunts to our babies and I am often the star attraction for sadistic sex. My taste in sex has moved more and more to men and there are always plenty around.
Jenny keeps one or two sissy boys in training always. I’ve never developed enough of a vicious side to punish them, but I do occasionally rat them out to Jenny or threaten them to gain sexual favors.