Samantha, A Different Kind of Love Ch. 01

by Jaqui Lynne


It was early evening and the sun was low in the midwinter sky. Darkness would soon overtake the landscape. I thought for a while, what should I wear to entice her, and it came to me... something silky, sheer. I had just gotten out of the shower, wanting to be extra clean for tonight, and had smoothed lotion all over my body, my face and private areas. It was the soft and sensual scent of "Passion" from the body lotion that filled the room and my senses. She will love it, I thought. Getting into my sexy dark blue silk panties and garter with black nylons on my freshly shaved legs, I began to recall about how I had arrived here... this life and my relationship with "Sam".

I remembered women from my past and how I had allowed myself to be used by them. I had lived with and loved many of them, yet none of the relationships ever worked. Then there was Mandy, who had shown me things I never thought I would experience. She was definitely kinky and opened my mind to new experiences. But those things took their toll on her and me as well. But she opened the door for me, and I started seeing sexuality in a whole new light. I was always a rather sensuous man....partly because I thought women wanted their guy that way and partly because of my deep inner longings. I wasn't into the rough stuff. I was into intimacy and passionate love making with long sensual kisses. Not that I didn't like to pound the hell out of some hot cunt…but I aimed to please. I didn't think of myself as effeminate, yet I yearned to feel what women felt. I fantasized of role changing. While making love to a woman I tried to feel what she was feeling. If I could do that, I thought, I would understand what they wanted. I was then , and still am, a very good lover. But most women, even after being satisfied sexually, still wanted some slug that either had a bigger wallet or a bigger dick, or some asshole that treated them like shit. I didn't get it.

So my search for some semblance of happiness and psychological and physical fulfillment continued. That's where "Sam" came in. I met her at a cocktail party one evening, at the house of a friend that I had met a while back when Mandy and I used to see each other. Sam was dressed in a dapper black suit with pinstripes and a lavender silk tie. "He" was about 5'-10", the same as myself, and had dark brown hair, though a little 'longish' for a business man, I thought, and steely blue eyes. I remembered thinking to myself how smooth and soft his skin looked for a guy.

His face had no lines and was quite smooth in appearance which made him look fairly young, though someone at the party remarked that he was about thirty five. I'm not certain why I stared at him. I suppose I was intrigued by his slim, yet well toned physique, his flawless facial features, and his smile. And when he spoke his voice was soft as well. I didn't usually think of guys this way....but with Sam, well, there was just something different about him. There was a strange attraction that drew me to study him. He looked my way and I hoped that he hadn't caught me staring. He turned to someone and asked about me. The lady whispered something into his ear and then Sam walked towards me. I wasn't sure what it was, but even in his stride there was something different.

"Hi, I'm Sam," he said, reaching out his hand to shake mine.

I took his hand and introduced myself," I'm Alex," I responded. His eyes stared into mine, almost as if he was reading my thoughts. He smelled a little flowery, not feminine, but not really masculine either. I couldn't quite place the scent, but I knew I had come across it before now. His hand was soft, slightly smaller than my own, and he held onto mine for more than a couple of seconds as if to sense something. He let go, but there was an energy between us that lingered and tingled my nerves. He must have sensed it as well and he smiled at me, not taking his eyes from mine. We didn't really say much, as I was feeling a bit nervous, violated, perhaps, and I'm sure this beautiful "guy" understood that.

"Well," he said, "I have to work in the morning, so I need to get some sleep. It was quite nice meeting you, Alex, I hope we can meet again."

"What line of work are you in?" I queried, my words drawing him back.

"Oh, I run an insurance office downtown, and that's where I live. I've got a condo there so I don't have to commute too far." There was a pause, then he continued, "And what about yourself?" he asked.

Feeling just a little uneasy about revealing too much about my life to this stranger, I held back a moment before responding, " Well, I run the sales department at a small marketing firm uptown."

We continued the small talk for a short time, talking about George, who threw the party this evening and mutual friends. But Sam said he really had to go, he didn't want to risk being late for work tomorrow. He walked away and said goodnight to everyone he knew there, then went for his coat. As he donned a full length woolen coat, he reached into his pocket and pulled out a card. He came over to my side and handed it to me.

"Give me a call if you're downtown sometime. Maybe we can grab a coffee or lunch or something." I took his card as his index finger stroked mine when I took it. I knew this was a conscious move on his part and I wasn't sure how to take it. Was this guy was propositioning me? Of course he was, but knowing that women were really my taste, I didn't respond in kind. Though I was not turned on by men, there was a feeling of some mutual attraction here...and that worried me.

"Sure, that would be good," I said, sounding a little uneasy. I didn't know why I felt that way, as I had been the one observing him and taking in his gentle, easy voice and suave manner and encouraging his movements. I watched him as he turned and left. I remember wondering who was this guy ,really. He seemed womanly in some of his mannerisms, and yet he appeared as this finely tuned business man. Was he gay? Probably, and I wasn't into men...but he didn't seem like the gay men I had come across in the past. Perhaps he was just one of the metro-sexual guys that have recently sprung up on society, primping and polishing themselves in the fashion that most women do.

I left that evening, and tried not to think too much about the encounter. I just went about my work over the next several months and kept pretty much to myself.


It was Friday. I had to meet a client for lunch at "The Stock Exchange", a really high end restaurant downtown. I had been looking forward to this for some time, trying to close a business deal that I'd been working on for the last three months. Finally the meeting was going to take place and I wanted to impress my client by taking him to this well established business environ. The company was paying for it, of course, so the price of a ritzy luncheon was nothing compared to what the deal would mean if secured. The client was a man of sophisticated means and demeanor, all business. We had an elaborate lunch, a cocktail and then got down to business. Everything went as planned, and the deal was finalized. After another drink, hands shook, and we went our respective ways. I was a bit taken over by the alcohol and didn't want to risk driving back to the office, deciding to take a hotel room instead. Though it was only the middle of the afternoon, I had convinced myself to take the rest of the day off and start an early weekend. Hell, I thought, I deserved it. I checked into a nice hotel just across the street, the Manchester, a place that offered the finest amenities and I knew my boss was going to hit the ceiling once he saw the tab for this place…but fuck it, I thought, I just made him a small mint this afternoon. Once situated in my suite, I called the office and filled them in on the afternoon's events. Afterwards, I took a nap, wanting to be fresh for a night on the town. It had been a while since I had been down here and I thought I'd make the most of the opportunity. I slept for a while and woke at about 9 pm… I got up, got showered and then dressed. I had remembered to bring extra clothes, a pair of jeans, clean underwear, a fresh shirt. I just wanted to explore the city's nightlife, be in the crowd and have a good time. At 9:30 I went out and wandered the streets I once knew and came across an old familiar haunt..."The Foxtail Lounge"...I entered.

The place was filled with smoke and the smell of booze. Music, jazz, light, earthy, soulful sounds tapped upon my ears, rhythmic acoustics surrounded me, and I swayed to the beat that encompassed the small crowd of patrons. I found a table and sat down, ordered a whiskey and water and just enjoyed the music. There were some women hanging together out at one of the tables and I observed them for a while, wondering if I would be able to attract some company for the evening.

After a couple of drinks and getting into the scene a woman came up behind me and said," I think I know you...would you mind if I joined you?"

I turned and looked up at her and without clearly seeing her features and said, "You know me?" I was surprised that anyone here would have recognized me. Curious, I stood up to further examine the lady. I met her-eye to eye and I saw a beautiful face before me. With lights dashing about us, I could only stare at her piercing eyes, her full, glistening lips, her lovely smile. She had mid length reddish hair, a slim body, standing just slightly taller than me since she was wearing heels. She wore a short leather skirt with a low-cut blouse that revealed everything. She had small globe titties, no bra. I could see her nipples sticking out through the thin fabric of her blouse, almost as if begging to be touched.

"I don't think so," I said, "I'm sure I would have remembered you, but you're more than welcome to join me." To which she let out a small chuckle. Yet, there was something familiar about her, as if I had seen that face before. But in the dim lounge light, it was difficult to be certain.

"Hi, Alex," she said , then waited for my stunned response. " I had hoped to see you again..." I didn't know what to say, I hesitated.... and then she went on, " I was so hoping you'd come around, or at least call me.... I mean... that's why I gave you my card." The card ...the card, I thought, trying to press my memory for a clue as to her identity. The voice seemed vaguely familiar, but I couldn't quite place it. Being a business man, I get cards all the time... who was this lovely creature, and why couldn't I recall her name? Surely I would have remembered her.

"It was at George's party, " she said, realizing my obvious confusion, " you were a bit shy, but I noticed you watching me...and I wasn't quite the "woman" then. I had to maintain my male image there," she continued," now, do you remember "the card"?"

"I....I...I'm not sure what to say…what to think," I said..."Is that really you... Sam," I asked, not believing this for a moment. Sam took my right hand and sat me down, taking her place at the empty chair beside me. Her left hand began caressing mine, and I felt a strange tingle of excitement as well as confusion fill my head. As I looked into her eyes, I saw that look that I now recalled from the night at George's place. It was true, this was "Sam".

"It's Samantha," she replied as she watched my face, eager to see if there was approval or rejection there for the words that she shared. I just stared into those lustful eyes, the eyes that I saw a few months back, the eyes that had then penetrated my mind and had left me with a feeling of wonder. She felt it, too. She felt the connection. I could see it, I could taste it. Overwhelming curiosity filled the moment we shared as we looked at one another. My mind reeled just a bit, partially because of the alcohol and partially from the intoxication of this mysterious woman, man…or whatever she was.

"I know you, Alex, I want you to know me, too," she paused for a moment then said,"...I want you to come with me." Having already had several drinks, I didn't much resist her overtures. I was stunned by the revelation, filled with curiosity, and simply complied with her request as she grabbed my hand, stood up and led us out of the club.

Samantha hailed a cab, one stopped, and we got in. She gave the driver an address and before long, we had arrived at her place. After a brief goodnight and a tip for the cabbie, she grabbed my arm and led me up the stairs to the lobby of her complex."Any problem," rang out a voice from a curious fellow as we passed through the lobby.

"No, no, I've got us under control," she replied as she guided me to the elevator, her right arm wrapped around my left. We entered the car and rose to the tenth floor. We entered her condo, whereupon she advanced to her stereo and turned on some easy music and then turned the lights down, creating a soft atmosphere. The place was nice, spacious and well appointed with various works of art. She obviously had good taste and must have had a pretty decent income to manage living in such a swank part of town. We sat down on her fine leather couch.

"I needed you here,...after I saw you at the club tonight, I had to see you ...I was upset that you hadn't called me.... then I remembered how sensitive you seemed to be. But I remembered what I felt.... what we felt that evening at George's place," she said, studying my reaction. "I really had thought of you quite a lot, and when I saw you this evening, well...I just had to take a chance."

I had to think about that for a moment before responding. "I'm not sure of what we have here, all I know is that you're a gorgeous woman.... or …well I'm not sure," I said, being blunt about the situation, and then I hesitated for a moment...trying to find the right words..." had I known you were this woman that I'm looking at right now...well, I might have thought differently," I explained," but I'm not into guys and I can't tell you why I was attracted to you that night, there was just something inexplicable about you that drew my attention."

"What are you looking for, Alex," she asked.

What kind of question was that, I thought. I had to think about that for a second. Was she really a woman pretending to be a man, or what if she were a guy trying to be a woman. I said, "All I want is what most people want, I suppose.....just to find some happiness and have some one special woman in my life to share it with."

Samantha took my hand me, pulling her legs up, positioned so that she was facing me at my left side. She glanced into my eyes and said, " Alex, I am really attracted to you....I don't know if you can see me now, ...past all the external stuff, but....I want you...I want you to see me as I really am." Her soft voice infiltrated my mind. "I live my life as a male....I run a business and have to keep my male facade in order to maintain my position....I can't reveal my real identity, or what I really feel and how I live when I'm not's quite a dichotomy, trying to maintain this double life."

With that said, she pulled off the red, mid-length wig she wore that evening. There was her real hair, as I remembered it, not so short, dark brown, slightly matted from the wig. She used both hands and mussed up her hair, shaking out the flatness imposed by her wig. Her lips glimmered in the low light, a pinkish-red color. Her mouth was beautiful, full lipped and asking to be kissed.

"I am curious, though," I said, listening to her admissions," about …," I hesitated, feeling a bit awkward asking what I was about to ask,"…well, are you Sam or are you something else?" There I said it.

Samantha got closer to me. She took my right hand and placed it on her right breast. There was definitely a breast there. It was a small mound that protruded out about an inch. Her nipple was large and she was obviously excited. She took my left hand and placed it on her other breast.

"I am becoming a woman," she said, " I have been taking hormones for a few years now, but no one else knows....and as for my business....they can't," she blurted, " I am successful as a man and I maintain my facade for the sake of what I need to accomplish, I don't think the company would understand, and I'm not certain how anyone would take it if they discovered my change."

"Eventually, though, as you continue your development it is going to be much more difficult to hide your feminine self," I said. "Hell, I'm convinced that you're a woman now, so how do you hide your obviously feminine act like a very sensuous woman?"

"I act, and portray myself as a sensitive male, leaving others to question my real identity and my breasts are small enough to cover up with my padded suit coat without revealing anything. I've always been somewhat effeminate, so personality-wise, I haven't changed much to those around me. But I do have a plan, it's just going to take a little time to implement it. And what about you… what do you think of my form?"

I looked at her body, looming over me now as I was sinking into her soft leather sofa. Her small, yet prevalent breasts and excited nipples were nearly caressing my lips as she moved closer to me, her right arm on the back of the sofa, behind my head. "You're quite a woman to me," I said as I pulled her by the back of her head towards me...her lips close to mine. Then I let my lips come even closer and my breath touched her with a gentle it all right? It was. Her lips fell firmly upon mine, her wet tongue parting my lips and glancing upon my tongue. Soon our mouths were completely engaged in oral edification, tongues licking each other in a sensuous rhythm, a full French kiss.

I didn't know what would happen next, but right now, at this moment, I was letting go and feeling incredibly aroused with her mouth planted on mine. This went on for several minutes, as we groped one another, our mouths never parting. Her breath was warm and the scent of her perfume filled my senses, and I was now completely ensconced in the sensations we shared. After several minutes, she pushed me back, trying to let us both catch our breath. She panted and was perspiring a bit, as was I. She slowly got off the couch, trying to stand up and regain her composure, nearly falling as she did. I tried to catch her, but she managed to recover on her own. She moved gracefully towards the wet bar as I watched her, my eyes glued to her slim, feminine form. She unstrapped her high heeled shoes, bending over and letting me see her panties, and long, luscious legs, then continued to the bar. The move was intentional, I thought, loving the way she teased. Her legs were bare, no nylons or pantyhose to obstruct the view of her silky smooth skin. Seeing her silhouette in the dim light, I could see the soft curves of her body...the decidedly female shoulders, shapely legs. If she hadn't been born a woman, she should have.

She poured a couple of glasses of scotch at the bar, but before making her way back with the drinks she lit several candles and turned the lights off. Now everything seemed to arouse my already heightened senses. I watched her and thought about that night at George's. It seemed like a long time ago, but had Samantha appeared then as she did now...I probably would have tried to hit on her then. Seeing her now she certainly seemed more feminine than anything.

She sat down next to me, staring into my eyes, handing me the drink. I no longer saw that "male" business man from that night. The smooth skin, the lips, the fragrance...all made sense to me and why she was so enticing then, even though posing as a man.

"Cigar?" she asked as she pointed to a small humidor on the coffee table.

"Well, yes, that would be good...goes nicely with scotch, don't you think?" I said.

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