by Rutger5

Don The Degenerate Doorman: Apartment 6B The Tipsy Fashionista
By rutger5 (An original story Copyright 2013)

Intro: Don the degenerate doorman ‘helps out’ drunk fashionista Emily.

It wasn’t the first time that Wednesday night that I stood and stretched my tired body to help prevent my muscles from cramping up on me. It was a quarter to eleven and my double shift was mercifully drawing to a close. Ivan, the regular doorman during the three to eleven shift had needed to take a few days off and as was often the case in the building some of us had filled the breach with me taking this particular shift.

Stan, the doorman who’d be relieving me to work the graveyard shift had already arrived and was in the locker room changing into his uniform. Stifling a yawn I headed outside to get a sniff of the pleasant spring air. It was a relatively quiet night in the heart of Manhattan and in spite of the seasonable May temperature the street was mostly deserted with only a few stragglers out and about.

I was just about to return to the lobby and in fact my hand was on the door handle when I heard a car pull up in front of the building. Turning I saw a yellow taxi had stopped there and it seemed as if the driver was engaged in an animated conversation with the passenger in back. Waiting out front in case it was necessary to hold the door I watched as the driver appeared to be pleading with the passenger until he threw his hands up in the air in apparent frustration. When he observed me watching he climbed out of the cab and headed in my direction.

“Hello sir” he said with a heavy accent “but maybe it is possible that you help me. You work in this building, no?”

“Yes I do. What seems to be the problem?” I inquired.

“My passenger says she lives here in building but I can’t get her out of the car. She give me the address and I drive her here but she is just sitting in the back crying. I think she is drunk, I don’t want to call police but what else can I do?”

“You did the right thing in coming to me, my friend” I told him as I walked to the cab and looked inside. “How much does she owe you?”

“Eighteen dollars sir.”

“Here you go. Can you print me a receipt while I help her out? For tax purposes” I explained as I handed him thirty dollars.

“Thank you sir. I get for you right away.”

I then turned my attention to the passenger huddled in the back seat who did indeed live in the building and I’d even held the door for her when she left earlier in the evening. She was subletting an apartment on the 6th floor from a long time tenant who was abroad for a year on business. Opening the door to the back seat I stuck my head inside after first removing my doorman hat.

“Good evening miss” I said in my most soothing tone “do you require any assistance getting out?”

“Huh, what?” she replied as she turned to look at me and her face was a mess.

Don’t misunderstand, she was a very striking and attractive young woman but at that moment her eyes were swollen and puffy and her mascara had left black streaks down the length of her face. Her designer blouse had what appeared to be a big wine stain on it while her short skirt had ridden up so high I caught a tantalizing glimpse of her black panties. Normally she was very put together with not a hair out of place but it was plain that something had upset her badly for when she’d left a few hours before she had seemed in high spirits. She stared blankly at me for a moment when sudden recognition lit up her pretty, tear stained face.

“I know you, don’t I? You opened the door for me tonight, right?”

“That’s correct miss and now I’m here to hold it for you again. You’ve arrived home.”

“Oh, did I? Okay” she replied after which she wiped the tears from her eyes then struggled to get out of the car.

I took a step back to give her some room and at that moment the cabby handed me the receipt which I took with a nod and slipped into my pocket. Fortunately for her I turned my attention back in her direction at that instant for no sooner had she clambered from the cab than she stumbled over the curb. Springing into action I caught her in my arms before she could execute a perfect face dive.

She had let out a shriek which was cut short when her body collided with mine and my strong arms encircled and drew her into my chest. It felt so nice having her soft, pliant body pressed against mine that for a moment I just cradled her. We remained like that until I realized we were standing on the street where anyone could see. My hands moved to her shoulders where they steadied her body before releasing her.

“Are you all right miss?” I asked her, my voice dripping with concern.

She took a minute to answer as she took stock of herself to make sure everything was okay before then blinking a couple of times as her big blue eyes met mine and she considered what I’d said.

“Yes I’m okay, but only because of you. Thanks for catching me, if you hadn’t…”

“Well no worries since I did. You ladies have to be careful when you wear such high heels” I told her in a matter of fact tone as my eyes fell upon the very high Jimmy Choo heels that adorned her seemingly perfect feet.

“Oh those, yeah they’re high, I think almost five inches. But it’s probably because I had too much wine to drink tonight.”

“Really. Well let’s get you into the building then so there won’t be any more problems tonight. May I offer you my arm, miss?” I asked solicitously.

“Okay, but I can trust you right…sorry I don’t even know your name. I suppose I should though, I’ve lived here for three months now.”

“No need to be sorry miss. My name is Don and yes you may trust me for I’m here to help” I told her as I guided her to the front door.

It took a bit of doing to hold the door open while still steadying her but I managed to accomplish this and get her inside the lobby before Stan managed to get off his lazy ass to hold the door. He saw the condition she was in and raised his eyebrows and all I could do was shrug helplessly in reply as I assisted her toward the elevators.

“Almost there now miss, we’ll have you in your apartment in no time” I told her like I would a child and it didn’t go over well with the drunk young woman for no sooner did I say it then she pulled free of me.

“First of all my name isn’t miss. I have a name – its Emily. And please stop patronizing me, I’m not two years old. I’m just a little tipsy is all.”

“I’m sorry Emily that I offended you, it wasn’t my intention. I was just hoping to get you home with no further complications. As soon as you’re safely there I won’t trouble you any further.”

“Sure just like every other man I’ve met. Can’t wait to get away from me as fast as you can” she replied as she leaned against the wall for support.

There was no way I or anyone else for that matter would win with Emily in the condition she was in though her last words gave me a pretty clear insight into the reason why she was upset. During the time I hit the elevator call button I turned away from Emily for a second and when I looked back she was in the process of sliding down the wall until she wound up sitting on the rug.

“Whoops I don’t understand it, now I’m on the floor” she said with a giggle before bursting into tears.

Ignoring the elevator whose doors had opened I approached Emily and bent down to speak with her and as I did my eyes took a fast peek at her lower half. Her skirt was now almost up to her waist, not only revealing her long smooth legs but her black silk panties as well and the sight caused me to forget how tired I was and to think about other, sordid possibilities.

“Whenever you’re ready Emily I can help you to your feet if you like” I told her after tearing my eyes away from her naked limbs.

“Okay Don, I’m ready” she said brushing away her tears and then extending her dainty hand in my direction.

My hand gripped hers at which time she pulled herself up with some assistance from me. No sooner had Emily regained her feet however than she staggered into me when she tried to take a step forward at which time she wrapped her arms around me to steady herself. Like had happened before on the street when her body met mine all I could think about was how nice she felt pressed against me and I was reluctant to release her.

But with Stan not far away as well as the lobby under constant video surveillance I knew better than to prolong this so I gently removed her arms from me and pulled her into the elevator. Not wanting her to fall again I kept my hand on her shoulder as we rode up to the sixth floor. It wasn’t until we reached her floor and the doors opened that tipsy young Emily realized that her skirt had ridden up almost to her waist.

“Wait one minute, don’t want to give any neighbors a free show” she told me as she tugged it down and as she did my narrowed eyes watched her like a rapacious bird of prey.

After she finished she looked my way and her eyes widened when she saw my burning gaze fixed on her shapely posterior. For a second I thought she was going to say something but instead she smiled slightly and walked off the elevator in the direction of her apartment with me trailing behind. And unless I was mistaken Emily exaggerated the sway of her round hips as she weaved her way down the hall.

When we arrived at her door she began rummaging through her purse though from her muttered curses she was having a hard time locating her keys. Finally with a cry of triumph she pulled her hand out clutching a key ring at which time she managed to drop her open purse and scatter all the contents across the carpeted hallway in all directions.

“Don’t worry about that Emily” I told her “you open the door and I’ll get your stuff for you.”

She had looked like she wanted to cry again after she dropped her purse but my words seemed to placate her.

“Okay Don, thanks” she answered as I crouched down and began to gather together the spilled items.

There was her cell phone and wallet of course along with other things that were standard fare for a young woman living in the big city. She must smoke for there was a pack of light cigarettes with a lighter as well as a tin of mints and a tube of lipstick. The most interesting item to my mind was the pack of condoms which were thin for ‘greater sensitivity’ they claimed. Personally I had no need of such artificial means for I’d been snipped many years before but they showed that Emily was ripe for the picking. Stuffing all the items back in her purse I stood up by which time she had managed to open the door and disappear inside the apartment.

“Emily, I have your purse” I called out as I stepped inside the empty foyer. When there was no answer I called out again, this time a little louder “Emily?”

“Can you please come here for a minute Don” came her faint reply.

Closing the door I first put down her purse and my hat and then followed the sound of her voice which emanated from beyond the apartment’s living room. Down a hall and through the first door to the left I found her kneeling on the bathroom floor before the porcelain throne.

“I don’t feel so good Don” she said in a sad sounding voice.

“Do you want me to stay for a little while Emily?”

She nodded yes like a little girl would, her pale blue eyes pleading with me, but I was more focused on the swell of her buttocks as they strained against the tight skirt she was wearing. Many a time I’d fucked some drunken woman in a bar or club bathroom so I found her current position very arousing. On top of that I remembered when her skirt was by her waist and how sweet her ass had looked in her bikini panties. Needless to say my cock was half hard in my pants when I knelt down and gently stroked her auburn hair while pulling it back away from her face.

“Do you think you’re going to be sick?” I asked her in my kindest sounding voice.

“I’m not sure, I feel a little queasy. I didn’t eat much today and I drank too much.”

“Oh, you poor thing” I told her sympathetically. “You have to remember to pace yourself if you’re drinking and not do it on an empty stomach.”

“I’m sorry but I was so upset.”

“No reason to tell me you’re sorry Emily, just saying for future reference is all.”

“You’re right I know but I wasn’t thinking clearly. Do you know what its like to be told during appetizers that you’re getting dumped for someone else? And I thought we were out celebrating our one month anniversary tonight.”

“Well all I can say is he must be an idiot Emily to dump a lovely young lady like you.”

When I said that I saw more than one emotion cross her face rapidly although the sad look won out in the end.

“No, I wish that was the case but its not. This isn’t the first time something like this has happened to me. No he was right.”

“Emily you have to remember that a young man doesn’t know what he’s looking for and probably isn’t smart enough to realize what he has…”

“That’s not it Don. Malcolm isn’t young, he’s almost fifty and he knows what he wants and I’m not it is all.”

“Well there you go. Maybe the difference in ages was too much…” I began but before I could finish she started to shake her head no.

“It isn’t that. The girl he left me for is only two years older than I am. It was the same thing that happened back in college with Professor Plumb only that time she was the same age as I am. No it’s me Don, no man wants a girl who can’t satisfy them in bed.”

It wasn’t often that I was speechless but Emily’s words caught me by surprise and I had no idea how best to reply to them. Staring at her sexy body as she knelt on the floor it was pretty obvious there was no issue there. Most men would give an awful lot for a chance to tap her so it must have been some other reason that was causing her problems. We remained like that for a few minutes and while we did I wracked my brain trying to formulate a plan to take advantage of the situation. Of course my eyes were feasting on her figure as I did, so when she spoke it broke the spell and made me look at her face.

“Don, you’re a man, can I ask you for some advice?”

“Certainly Emily, I’ll do my best” I replied.

“Thank you and please be honest, no matter what. Lying to make me feel better won’t help. I need the truth if I’m going to improve things.”


“What kind of girl does a man want? I don’t mean how she looks. I know some men like girls with blond hair or big boobs or whatever superficial preference. I mean what does he expect from her?”

That was a tricky spot she put me in but I saw an opportunity to turn it in my favor though I had to consider my words carefully or risk blowing it. The first thing was to delay her a bit to allow me to fine tune what I was going to say.

“I’ll be glad to answer you Emily but let me ask you something first. Are you feeling a little better? Because it would be more comfortable to not be having this conversation on the bathroom floor. Are you feeling up to getting off the floor and sitting down?”

She paused before answering but she nodded her head yes after thinking about it. Once I stood I reached down and helped Emily to her feet after which we went into the living room where she sat on the couch.

“Would you like some water to hydrate?”

“Yes please Don. You are so sweet” she told me and boy she had no clue.

If she knew what I was really thinking those wouldn’t have been the words out of her lips. Lips I was imagining wrapped around my hard cock as she sucked. In her refrigerator I found a pitcher of water with lemons in it so I poured her a glass. There were also two bottles of beer, they were light but beggars can’t be choosers so I removed one.

“Emily, I notice you have some beer as well. It’s been a long day and night for me, do you mind if I have one?” I asked her.

“Of course not, take one. Yeah I usually have some there, I guess you can take the girl out of Wisconsin but you can’t take Wisconsin out of the girl.”

“From the Midwest, huh? No wonder you’re so sweet and innocent” I replied making her blush while handing her the glass.

So a minute later I was sitting next to her on the couch and after drinking half the beer I turned her way.

“I could tell you what I like in a woman but that isn’t really what you want. First I need you to say why you think it’s your fault about things never working out.”

“Maybe because that’s what they tell me Don. Tonight Malcolm said he is too old to try and train someone to please him. ‘If you don’t know what to do by the time you’re twenty three then what’s the point?’ he said. And Professor Plumb called me a prude and said it was too bad I wasn’t Catholic because I’d have made a great nun.”

“Okay” I said holding up a hand to stop her from saying more and probably becoming more upset. “Let me ask you something and you answer truthfully. Do you like having sex Emily? Because you’re very attractive so most guys would have interest in you.”

She bit her lip before she answered and when she spoke her eyes darted about, not willing to meet mine.

“I do, I like sex Don. But I am kind of inhibited, I guess. I mean when I’m having it I have a good time and enjoy it but I’m pretty passive” she said in a voice barely above a whisper.

“But?” I added for I could tell she wanted to say more.

“Well, the thing is, I was raised a certain way. My mom died when I was young so it was just me and my father. He loves me I think, but he was never one to talk about things like emotions let alone about sex. When I first had my period he gave me a box of ‘feminine products’ as he called them and a textbook on human sexuality with a bookmark at the relevant section. He was a science teacher so to him that made sense, I guess.”

“So you had no woman to talk with about stuff growing up.”

“Well I talked with my friends some but it wasn’t like they were experts either plus of course the internet. So I kind of muddled my way through puberty. The only other guidance I got from him was when I was fourteen and a neighbor girl got pregnant. He told me in a solemn tone that he couldn’t imagine what her poor parents were going through, everyone in town knowing their daughter was a harlot as he put it. Needless to say I was very repressed and was too scared to date until much later than all my friends. Even when I started I didn’t let my father know because I knew he wouldn’t approve of any of the boys.”

“So if you don’t mind me asking how did you ever get beyond that to start having sex?”

“I don’t think I’ve gotten beyond my upbringing. That might be why I still have problems with men. I lost my virginity after the senior prom in high school but my ‘boyfriend’ if you can call him that was a total jerk who only cared about pleasing himself. So when I went away to college and Professor Plumb showed interest in me I thought finally here is my chance. He wasn’t some young guy only caring about himself and getting off, he was a mature man of the world who would treat me right. What a joke! He was a total sex maniac and I was just one in a long line of students he bedded. I didn’t care though and I would have continued going out with him but he dumped me for a less inhibited girl. Then I hoped when I moved to New York things would improve but it’s still happening to me.”

“Let me ask you about that. Why move here in the first place, this city has a reputation for being decadent?”

“That’s what my father said, Sodom and Gomorrah on the Hudson he calls this place. But the fashion industry is my life’s passion, that’s what I went to school for. I know right now I’m not good enough to be an actual designer but I took some business and writing courses to go along with those on design. Right now I’m working for a major designer while trying to write articles on fashion as a freelancer as well.”

“You also seem to favor older men, much older it seems. Any thoughts why?”

“Well my high school boyfriend was my age and he was immature and selfish so I figured I’d be better off with someone older. I don’t know, older men seem more attractive and distinguished looking to me.”

Now I’m no psychiatrist (though I have held open the door for many) but you didn’t have to be Sigmund Freud to read between the lines in regard to what Emily really meant. So we sat there a while after this and I did my best to look like I was contemplating what she’d said when I was really plotting what was to follow. After finishing my beer I met her eyes then took a deep breath before speaking.

“Okay Emily, I believe I can help if you let me. I just need for you to answer another question. Do you ever masturbate?”

“Y-y-yes, s- s-sometimes.”

“How often? A lot?”

“N-n-no, not a lot. Every now and then when I get real worked up and need relief and there’s nobody to help me.”

“Do you use anything to masturbate, like a vibrator maybe?”

“No, I’ve never owned a vibrator in my life. Sometimes in the shower I let the water hit me there or I rub myself with a shampoo bottle or something.”

“Any other objects?” I asked while imagining Emily naked in the shower with the water hitting her clit which made my hard cock twitch in my pants.

“When I was younger sometimes I used my hairbrush.”

“Lucky hairbrush” I replied with a leer causing Emily to blush uncontrollably. “Now go get a brush.”

“You want me to get one now, but why?”

“To help you conquer your inhibitions Emily. Listen you don’t have to do anything you don’t want to but remember that I’m just trying to help. It’s up to you. But right now you’re open to change and the alcohol you had will help with that. If you do what I say we can get you over the hump I think. Your choice.”

“O-o-okay, I’ll do it” she said as she stood.

“Good girl, Daddy Don is proud of you” I said to raise the stakes higher.

She blanched when hearing what I called myself but it seemed as if she was serious about trying to change and without another word she walked from the room with my eyes locked on her ass as she did. Emily returned a couple of minutes later with a hairbrush in her hand and apprehension on her pretty face.

“Are you normally dressed when you masturbate Emily?”


“Well then maybe you should take off your clothes.”

I sat there impassively as she undressed but internally was another matter. My heart beat faster as each article of clothing came off and my cock swelled until it felt like it might burst. She had removed her blouse first and her full breasts looked spectacular even partially covered by her Agent Provocateur brassiere and when she removed that I felt my mouth go dry. She next unzipped her skirt and shimmied out of it leaving her only in her heels and black panties.

“Leave the heels on” I ordered her, my voice sounding hoarse to me.

She nodded then looked at the floor as she slipped her fingers under the waistband and slid her panties down. I let out a low whistle seeing her hairless mound and when I caught a glimpse of her pink as she removed the silky lingerie I had to stop myself from standing. Instead I clenched my hands into balls while my eyes devoured every inch of her nude form.

“Breathtaking is all I can say Emily, you are truly a beautiful young woman.”

“Thanks” she replied shyly.

“Now I want you to go to the window and open the curtains.”

“O-o-open the curtains?”

“Yes – open them now!” I demanded.

She swallowed hard but then her face took on a determined expression and as I watched she reached out and pulled the curtains wide exposing herself to any who could see into the sixth floor window.

“Now Emily sit your sexy ass on the windowsill so you’re sideways.”

Once she was settled with one leg resting on the sill and the other hanging down I stood and moved closer to her though I didn’t want to come close enough to make her feel uncomfortable.

“Play with your breasts to start with Emily, nice and slow if you don’t mind.”

After putting the brush on the sill her hands reached up and cupped her full breasts and then squeezed them, gently at first.

“Pinch those nipples now. Make them nice and hard” I instructed her and she wasted no time in following my words to the letter.

She let out a little gasp when they hardened from her touch and she threw her head back a little while biting her lip from the feeling it gave her.

“That’s it Emily. Just imagine all the men in the building across the street watching while you do this. They’re getting very turned on from what you’re up to. Right now some of them are getting hard and starting to play with their cocks imagining being with you. Does that thought turn you on?”

Emily looked at me after I said this and her mouth opened in surprise when she saw I was in the process of removing my swollen erection from my trousers. I smiled at her as my hand started to stroke my thick cock and already there was some pre-cum oozing out the slit.

“Move one of your hands to your pussy Emily.”

Her hand trembled slightly as it moved off her aroused nipple and down her body winding up at the sweet nexus between her thighs. While I watched Emily pet her little hairless pussy I continued stroking my rock hard cock and more than once I had to stop myself from going too fast. Better to let her overcome her inhibitions slowly rather then rushing her and having a setback with my plan.

“How does it feel playing with yourself, are you getting turned on yet Em?”

“Yes I am, it feels so good” she managed to reply as her breathing quickened from her body’s arousal.

“Is your pretty, pink pussy getting all wet and juicy?”

“It is, I’m so wet right now.”

“Then show me Emily. Spread your lips wide so I can see your juices, show Daddy Don.”

She gulped in reaction to my words but her slender fingers did what I asked and pushed her lips apart. I could see the sheen of fluids in her tiny twat as she opened it for my viewing pleasure when inspiration gifted me another idea.

“Bring your other hand down and put your finger in your pussy for me Em.”

When her fingertip slid inside it made a squishy sound as it entered after which Emily began to make mewing sounds but I didn’t let her keep it there too long.

“Okay, that’s enough for now, let me see your finger.”

She removed her finger and presented it to me for approval and I took her hand in mine as my tongue slowly licked the tasty juices off it.

“Hmmm, you taste so good Em. Your puss is delish, I can’t wait to eat you” I told her. “Does that turn you on?”

“Oh God yes, I’m so turned on.”

“I’m so turned on Daddy Don” I corrected her. “Now play with your clit and you can put your finger back inside your hot little pussy as well if you like” I said as I released her hand.

“I’m so turned on…Daddy Don” she told me as her digit re-entered her channel.

“Slide it in and out” I told her and again Emily wasted no time in following my directive.

Her slender finger disappeared inside her only to re-emerge covered with her nectar before starting the process anew. Wanting to get a better view I moved closer to her and crouched so my face was on the same level as her sweet, fragrant pussy. There I watched her finger being gripped by her inner lips as it worked in deeper then it pulled back when I noticed the forgotten hairbrush sitting nearby. It was made of hard pink plastic and had a narrow handle before widening at the section where the bristles were attached.

“Emily I want you to take your finger out of your pussy and replace it with your hairbrush.”

“You want me to put it inside me? I’ve never done that before. I used to just rub it on the outside of me.”

“You mean you used to rub it on the outside of your pussy. I want you to use that word when that’s what you’re talking about, or you can say cunt if you prefer. You have to remember what we’re doing here is trying to cure your prudishness.”

“Okay, I’ll try but it’s not easy after all these years” she told me after taking a deep breath. “I used to rub it on the outside of my pussy Daddy Don.”

“Good girl Em. To start with then just do that and we’ll go from there.”

She picked up the brush and true to her word started to slide it back and forth in the furrow of her pussy. The rigid plastic handle split her wet lips as she moved it up and down while her other hand continued to play with her erect clit, alternating rubbing and pinching the erect nubbin.

“That is so fucking hot Emily, you’re turning me on so much. Damn you are one sexy girl, just the way your Daddy Don likes them. Now I want you to fuck yourself with the hairbrush, put in in your tight little pussy. Can you do that for me?”

Emily nodded her head and as I watched she adjusted the brush in her hand so the end was aimed at her wet opening. She let out a moan as it started to penetrate her and once a couple of inches had worked their way inside then her young body stiffened and tensed as her hand continued to feverishly rub her clit.

“That’s it baby girl, cum for me” I told her though by this time my words of encouragement were no longer needed.

Emily let out a wail after which she bit her lower lip hard as her pale face reddened and glorious orgasm overtook her. That was the final straw that broke my control and I could no longer take just remaining a spectator as the young woman climaxed in front of me. I rose from the crouch I’d been in and leaned my head forward until my mouth clamped on her erect nipple. Emily moaned and when my hand covered hers and guided the handle deeper inside her the moan became louder.

My lips released her nipple then kissed their way up until finding her sweet mouth and she tasted like wine to me. Emily eagerly responded to my kiss, in fact as soon as my mouth opened her nimble tongue slipped inside to wrestle with mine. During this our hands continued to work the hard pink handle in and out of her tight pussy as deep as it could go. Meanwhile my hard cock rubbed against the smooth, silky skin of her dangling leg leaving a trail of clear, sticky pre-cum wherever it touched and inflaming my passion to the boiling point.

With some reluctance I broke the kiss but only so I could sample Emily’s womanly essence. My mouth now worked down her aroused body from her slender neck to her hairless mound, leaving a trail of burning hot kisses wherever it went. Finally it zeroed in on her erect little berry and my lips closed around it and sucked hard while all the while I continued to fuck her with the brush handle.

This pushed Emily’s body into another orgasm, this one more intense than the last judging by her reaction. She thrashed about wildly and the fingers from her hand not on the brush dug into the flesh of my shoulder as she let out a series of low moans as she came. When her trembling subsided I released her clit from between my lips and straightened my body so I could look her in the eye.

Emily wore the expression of a satisfied woman though we had just begun and had much more to do before concluding. My hand guided hers in removing the brush from her pussy at which time I brought it up near her face. The handle was slick with her juices and I touched her lips with it.

“Suck on it Emily until none of your pussy juice is left there.”

Without batting an eye Em opened her mouth and slipped it inside and began sucking. By this time my cock was so hard and ached so badly that I didn’t know how I was still thinking straight but I had one more task to complete before thinking of my own satisfaction. I removed the brush from her mouth then stared at her until she blushed and cast her baby blues down unwilling to meet my gaze.

“How did you like the taste of your pussy Emily? Enquiring minds want to know.”

Her face got even redder from my bold question and she gave me no answer and continued to avoid making eye contact until my hand took her by her chin and tilted her pretty face up.

“It would’ve been polite if you gave me an answer but that’s okay Em. I know how good you taste and now so do you even if you’re not ready to say it. I think we’ve made good progress so far though we still have a ways to go. I have to say for someone so repressed you have managed to exceed my initial expectations. Masturbating by an open window so anyone can see is a step in the right direction, one might even say it’s naughty. And naughty girls need to be disciplined” I told her while making my voice harsher for the last sentence and causing Emily’s blue eyes to open wide from my tone.

I took one step back after which I spoke again.

“Get off the windowsill now and face outside Emily.”

She scrambled into position and once she had I pushed her upper half down so she was bent at the waist.

“Now put the palms of your hands flat on the sill and look straight out the window” I instructed her and as soon as she complied I used my foot to move one of her feet further from the other.

“Were you ever spanked when you were a girl?”

“N-n-no, my father didn’t believe in corporal punishment. He believed it was more productive to reason with me instead.”

“Well I can tell you that Daddy Don is a firm believer in spanking. In my opinion when you spare the rod you spoil the girl and that’s the root of your problem I believe. I’m not going to make the same mistake” I growled right before I brought the brush handle across her taut buttocks.

Emily let out a yelp when it connected with her supple ass and her body flinched a bit so I placed my free hand on the small of her back to hold her in place. For the next couple of minutes I rained down blows on her defenseless flesh as she squirmed and cried though I give her credit for not asking me to stop. I did my best to space the blows out and not hit the same spot too often while making sure every inch of her sweet ass received the attention it so richly deserved.

The reason I stopped wasn’t because I felt sorry for Emily or thought she couldn’t take more but it was my lust finally got the better of me. Since seeing her panties in the cab I’d desired her and my cock had been erect since she’d been kneeling on the bathroom floor and I couldn’t wait any longer. Dropping the brush to the floor I grabbed my shaft as I positioned myself directly behind her. When my swollen head first brushed against her wet sex she gasped and as I rubbed it on the outside of her lips it turned to a moan.

“Emily I want you to take hold of my hard cock and guide it to your pussy, but that’s only if you want me to fuck you.”

No sooner were the words out of my mouth then her right hand moved from the sill and reached back between her thighs. It was my turn to gasp when her warm hand wrapped around me and she wasted no time in bringing me to her gates of paradise. Once she positioned me at her hole I pushed forward, my head forcing its way inside her tight, pink pussy. It was slow going as she adjusted to me for I was much wider than the brush handle but through perseverance and Em’s natural lubricant progress was made until only a couple of inches of cock remained outside her.

“All right Emily, we’re almost there” I told her as I marshaled my energy for the final push. “When I say now I want you to push your ass back towards me, okay?”

She nodded her head in reply at which time I said okay. Emily pushed back while I thrust forward burying my cock to its limit as my pelvis collided with her ass and my swinging balls slapped her clit. My hands grabbed her hips which allowed me to pull her into my forward thrusts as we built up a fast rhythm. The room was soon filled with the scent of her arousal and the sounds of our coupling bodies meeting.

While watching my cock slide in and out of her clinging flesh I have to admit that my attention was drawn by the puckered rosebud just above her pussy. It seemed to be calling to me as I drove my cock to its limit a few inches beneath and I felt it would be a good test to see if Emily was winning the battle versus ingrained prudishness. However it would have to wait for I had no intention of stopping until I filled her pussy with my cum.

My body bent at the waist until my chest and stomach were brushing the soft skin of Em’s back and it felt hot to the touch and excited me further than I already was. My lips kissed the back of her sweaty neck as my hands slid from her hips and traveled to her swaying breasts which they seized roughly. I felt her pussy muscles contract on me when I grabbed her and she pushed her ass to meet me.

“That’s it Emily, fuck me like you mean it” I grunted as my hips increased their speed. “I can’t take much more of this, I’m gonna blow my load!”

My hands squeezed her pillowy breasts while I continued pumping as hard as I could until I felt it begin. I managed a couple of more thrusts when the sublime feeling of my balls releasing their semen overcame me as I drove deep in Em one final time. After that my body remained motionless as my cock swelled then spewed its thick, creamy ejaculate deep in Emily’s puss.

“Fuck yes! I’m cumming!” I called out as I fired spurt after spurt in her.

“Don, wait, don’t cum in me” she said in a sudden panic as she felt my discharge filling her vaginal tunnel.

“It’s too late for that Em, but no need to worry. I was fixed years ago so I can’t get you pregnant if that’s what you’re worried about” I whispered in her ear as the last drop of my cum seeped into her vagina.

With a groan I let go of her breasts then straightened my body before reaching down and encircling the base of my cock with my hand.

“Get ready Em, I’m going to pull out of you and when I do I want you to suck my cock clean of both our juices. Do you think you can do that like a real naughty girl would?”

“You just watch me Daddy Don” she replied in a determined voice after which I stepped back allowing my softening member to slide from her welcoming depths.

Emily was true to her word and as soon as I slipped free she turned around while staying bent over. Her hand grasped my shaft and a second later her mouth took my head inside and she kept going, swallowing more of me until my tip hit the entrance to her throat.

“That’s it Emily, don’t forget to use your tongue while you’re at it. Lick up all that cum from both of us.”

She did as I asked and once the part in her mouth was licked clean she pulled her mouth off me and then began to run her tongue on the section that hadn’t fit in her mouth. Not only was she doing a great job of removing fluids but her efforts were also helping me retain my erection for the most part. My hands took her by the shoulders and pulled her up to a standing position and once they had I kissed her dirty mouth hard.

Emily eagerly returned my kiss and letting my cock loose she wrapped her arms around my waist drawing our bodies close. My three quarter erection pushed into her belly due to our height differential as our tongues wrestled and we swapped spit until I broke the kiss.

“Your call Em, but what do you say about heading into your bedroom and continuing this there?”

“I say yes!” she told me while taking my hand and leading me from the window.

A minute later found us again kissing as we stood in front of her bed. Seeing no need to delay things I pulled my mouth from hers with the intent of pushing her onto the mattress when I noticed it was covered by many scattered items of clothing. No doubt Emily like most women I’d known had tried on multiple outfits before deciding on a final one to wear that evening. Knowing she took fashion seriously and had some expensive designer clothes I bent and scooped the clothing up and tossed it onto a chair clearing a space where I then pushed her onto her back. She looked up at me with a little smile as I quickly began to remove my clothing.

No sooner had I undressed then I climbed on top of her and guided my cock into her well fucked pussy. Emily squealed as I worked back inside her and once I bottomed out her lithe legs wrapped around me. I ground my pelvis against hers and she did her best to match me, rotating her hips as much as she was able to in her current position. Her pussy was very wet and was dripping vaginal fluids which coated both our thighs and seeped down to the sheets below.

“I don’t know for sure Em, but I have a feeling you might have conquered your prudishness. Have to see if you can do this while sober but the signs look promising” I whispered in her ear as I repeatedly filled her pussy with my hard meat.

“Oh, I think you’re right, thanks to you Daddy Don” she groaned in reply and a minute later I felt her teeth clamp on my shoulder and her pussy contract on my cock as she came.

When her spasms subsided I figured now was the time to approach her on what I’d been desiring since first seeing her beautiful round ass. I re-positioned my body so my torso was perpendicular to the bed while kneeling on the bed as I continued to drive my full length inside her. After a minute or two my hands grabbed behind her knees and pushed her legs up to her chest. That allowed me to go even deeper in her tight little pussy and it felt so good that even though I wanted more I had to savor this for a little longer.

It worked out well for with her body the way it was Emily was soon crying out loudly and when I accidentally slipped out of her she gushed out a large volume of liquid soaking us both. Her face became even redder than it had been before.

“Sorry” she said quietly.

“Don’t be” I replied. “That’s a remnant of prudishness speaking. Remember that you are a sexual and desirable woman who’s in touch with her feelings and is proud when she squirts from a good fucking.”

“Okay, you’re right, I guess. Thanks Daddy Don for reminding me.”

“No problem Em, just doing my part.”

While I continued to hold her legs against her chest I shifted my body and climbed off the bed which let me lean in and kiss her soaked pussy. Eagerly I lapped up her juices until my chin was wet from them before moving a couple of inches south where my tongue flicked her brown hole.

“D-d-don, what are you doing?” she asked with a trace of panic in her voice.

I continued to lick her ass for another minute before pulling my tongue back so I could reply.

“It seems pretty clear that I’m giving you a rim job Emily. Why?”

“I don’t know, you aren’t planning to do anything, are you?”

“Uh oh, looks like I was wrong after all about you. Maybe Malcolm was right after all if me licking your ass is enough to bug you out.”

“No, it’s just that back when I dated that jerk in high school he talked me into letting him, you know, and it hurt a lot.”

“Do you mean you let him fuck your ass, is that what you meant?”

“Yes” she admitted sheepishly.

“I admit I do find that surprising Em that you let him.”

“I know and the truth is I let him do that before I let him do it the normal way. I heard that was a good way to keep a boy interested but stay a virgin.”

“Some girls just give blowjobs instead though I wish back when I was in high school the girls had done it your way.”

Now as this conversation went on I was licking her tight little butt hole as she spoke and stopping as I did and the longer it went on she began to squirm so I decided to up the ante and tickle her with my fingertip making her even crazier.

“He talked me into it and I only did it that one time” she gasped as I gently prodded her.

“Well I hope you’re not comparing me to him. I would think that I have a little more class than a high school boy and can do a better job.”

“Oh you’re in a whole different league, but you’re bigger than he was so it’s bound to hurt more.”

“Please Em, give me a little credit. Just relax and let me work my magic. If at any time you want me to stop all you’ll have to do is ask. Okay?” I said as I slid my index finger in her pussy to lubricate it.

“What the hell, why not I guess. I’ve done everything else tonight. But please go slow.”

“Of course my dear” I told her as I slid from her pussy and next pushed my fingertip in her tight backdoor. “Relax sweetie, I can feel you tensing up.”

“Sorry Daddy Don, I’m trying.”

“I have an idea. Why don’t you hold your legs to your chest to free both my hands.”

Once she did I was able to slide two fingers in her hungry pussy as the finger from my other hand continued to probe her ass. While doing this I would occasionally flick her clit with my tongue and soon Emily was getting into it judging by her moans and how her juices were dripping anew. Realizing that I had to keep moving forward I managed to squeeze a second finger in her ass and began to slide them in and out. As she began to loosen up I started sucking hard on her clit and the stimulation from both her holes being finger fucked at the same time proved too much for her to handle.

I’m not sure how many orgasms she had previously but this one was a doozy. Her internal muscles clamped so hard on my fingers that they were held hostage and her body thrashed about while she wailed like a drunken banshee. I waited until she calmed before moving my face close to hers and speaking.

“Well what do you say Emily, any chance I can fill that hot ass of your’s?”

“The way I feel right now I’d let you do whatever you want.”

My face broke into an ear to ear grin on hearing that and I wasted little time in getting in the proper position. The only change from our previous position when I’d been fucking her on the bed was that I slipped a pillow under her ass to raise it off the mattress some. The head of my cock was now brushing against her backdoor but I made sure to resume playing with her pussy before attempting to penetrate her butt.

So for the next minute I jammed my fingers deep in her and as she got into it I began pushing into her sphincter. She grunted and groaned a little but I slowly continued until my head forced past the ring and disappeared in her anus. Once that happened I stopped pushing but kept my hand busy playing with her. By watching her face I saw she was handling it well so I resumed my effort and worked some more cock in her until half my length was inside her.

It felt so awesome on my flesh, tight and hot and forbidden. My hips then began to slowly work back and forth while my brain thought ‘Yes I’m fucking Emily in the ass!’ In spite of me taking it easy and only being partially in her I was having to put in my best effort not to cum from her being so tight. The girl must poop only tiny rabbit pellets from how small her channel felt to me. Not that it was a bad thing, just I had to go nice and slow, sliding half my length in before pulling out and leaving only my head ensconced.

My fingers continued to probe her pussy and by this time I had curled them so they could stimulate her g-spot with each thrust. The next time she squirted I took the opportunity to work my cock deeper in her ass until with a final push my balls hit her ass. I waited a minute as her body adjusted to this further intrusion before moving more though by this time I knew she was handling it well.

“Oh my hot little Emily, I want you to do something baby. Use one arm and hand to hold your legs in place so you can play with your hairless pussy with the other. Can you do that for me baby?”

She opened her half lidded eyes and nodded to me. “Yes I can do it Daddy Don.”

“That’s a good, naughty girl Em” I said as I removed my fingers from her and brought them to her mouth.

There was no need for me to say anything this time as she parted her lips and swallowed them, her tongue licking them clean. Once they were I removed my fingers and grabbed hold of her hips with both hands as I adjusted my hips slightly.

“Well, how do you taste Em? I asked you before but you didn’t answer me.”

“Hmm, I taste awesome Daddy Don” she replied fighting back laughter it seemed to me.

But she did as I asked and brought her hand to her sopping pussy and began to pet it.

“Oh fuck Emily! Your hot little ass is going to make me cum. I’m going to give you a cum enema baby girl” I grunted as I felt my face flush while my heart beat like a jackhammer gone wild.

After another few thrusts my body stiffened as I swelled in her anal vise then my balls released their load. My head fired it deep inside her and irrigated her bowels with my white, sticky fluid. In spite of me gasping for breath from my exertions I had to lean in and kiss her sweet, burning lips again. Her hand ran through my hair while we kissed and our bodies slowly came down from the heights of passion.

Finally with a groan I withdrew what was left of my erection from her and managed to roll onto my back. Leaving no doubt that she had overcome her prudishness, at least for this night, Emily crawled between my legs and took hold of my spent cock. After locking her blue eyes on my more pedestrian brown ones she started licking and sucking on my cock which had just sodomized her. After a minute of this beautiful torture Emily stretched out beside me and rested her auburn hair on my shoulder while keeping hold of my cock.

“That was so nice Daddy Don” she whispered in a sleepy voice. “You’re staying the night, right?”

“I’d love to baby girl, if you want. I have to be back on duty at seven in the morning so if I don’t stay here I’d have to sleep on a chair in the locker room downstairs to make it back in time. Of course I’d much rather be with you than a lonely old chair.”

“Good, you stay here. My alarm is set for early anyway and this way you can shower in the morning.”

“That’s a good thing, otherwise all day people would give me strange looks for smelling like Emily in heat.”

She giggled and snuggled closer to me as I closed my eyes and let the sandman take me away. The next morning I actually woke before the alarm for my body was trained to rise early in order for me to make it to work on time. I smiled as I took in the wonderful sight of Em’s naked sleeping body as I slid out of bed. After a quick shower I crept back into the room and gathered my clothes together. I dressed in the living room before silently exiting the apartment.

The electric razor I kept in my locker came in handy as I shaved after which I headed to the lobby. I could tell by Stan’s expression he was jealous but what can I say. It’s good to be Don the doorman. To make it up to him I bought him a coffee and bagel to go with my own before assuming my place at the front desk.

Later that morning Emily approached the desk after she left the elevator and it was the normal version with not a hair out of place but there was a look of uncertainty on her flawless face.

“Good morning miss” I said to her, my face a mask.

“Morning. I just want to thank you for last night. I know I wasn’t myself and you were very helpful.”

“Not at all miss, I assure you the pleasure was all mine” I replied and though my expression remained impassive my eyes reflected a lot more.

“No Don, not only your’s.”

After saying that she turned and headed to the door which Jose held open for her. Later it was around noon and I was manning the front door so Jose could eat when he approached me.

“Don, you have a call on the lobby phone. She says she’s a tenant and asked for you by name.”

“Okay thanks. Once I take the call I’ll come back to the door.”

“Hello this is Don, how may I help you?” I spoke into the receiver.

“Hi Don, this is Emily. I was wondering if I might have your cell number. There’s something I wish to send you.”

“Certainly miss” I replied after which I told her what she wanted.

It was around twenty minutes later and I was back at the front door when I felt my phone vibrate and before I could get to answer it happened again. Opening it I saw I had received two messages with attachments. The first was a picture of what appeared to be two bare female legs sitting on a toilet with a vibrator between them and the second showed the same vibrator buried inside one of the sweetest, barest pussies I’d ever had the pleasure of tasting. This picture had a text message which read ‘Don, I bought a vibrator today but I’m not sure if I’m doing it right. Maybe you can help me later. Em’

My fingers quickly tapped out a reply as I felt my groin swell with blood. ‘I’ll be glad to assist you anytime Emily. What time will you be arriving this evening?’