Category: First Time Virgin Sex Stories
Published: Sep 15, 2004
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The first week of sharing Margo's apartment with her was all I had hoped it would be. We had been lovers before, and would make love to each other many times again, but we did not live together as lovers. The apartment had a second bedroom which Margo had been using to store odds and ends. We cleaned that out to become my bedroom. We both shared Margo's bed for the first few days, but by Thursday night my somehow appropriately queen-sized bed arrived, and we each had our own room.
We came to an agreement right away on the, for lack of a better phrase, "sexual arrangements" for our place. On average, men tend to have their casual affairs outside of their living space while women tend to bring their sex home with them. If we held to that statistic, we would each need a place to be bedded by our lovers. We decided that whatever we did in the privacy of our own rooms with whomever we chose to do it, was our own business. The living room would be for mutual use for entertaining with our clothes on unless we were both entertaining the same lover, or the other one had previously announced her intentions of being out all night. The kitchen was our place, and off-limits to lovers. These arrangements worked well, and we held to them all the while we lived together.
The only problem I had was the need to keep my male job, so that I could pay my half of the rent. How I loathed getting up each morning, and putting on that stifling male clothing, and heavy shoes to trudge to work. The job was not difficult. I was the stockboy in the Children's Shoes Department of a famous 5th Avenue department store. The problem was that I had to do it as a male, and I no longer wanted to be male in any way! I had to find a way to change that, or at least the job. I did not yet know how to do it, but I knew I would somehow find a way.
As soon as I got home from work each night, I would shower, and change into some frilly lingerie borrowed from Margo. She was generous to a fault with me, but I could not continue to borrow things all the time. She had made me a present of the white outfit that I had worn on my first night in Drag, but a girl needs more than one outfit. There was but one answer. We had to do what every woman enjoys doing more than anything else. We had to go shopping!
Saturday morning was bright and breezy in New York City. It had been one week since my first night in Drag, and it was time to take the next step. Margo layed out the outfit I would wear after breakfast. There was a yellow based floral print skirt with a hemline that fell just above my knee, and a matching loose fitting jacket. To go with that was a light pastel green silk blouse, and green shoes and bag that were almost the same color as the blouse. Margo also let me wear the aqua lingerie set that she had worn last Saturday. I tucked my penis back into my crotch, and slipped on the panties. "Always dress to the nines when you go out shopping," Margo told me as we put our clothes on. "You get a lot better service from the tacky shopgirls when you look better than they do!" She was right.
I was shifting things from the pink purse to the one Margo had just given me when I came upon something I had almost forgotten in the rigors of moving that week. It was Peter's business card. Peter and I had danced at "The Gilded Grape" last Saturday night, and I promised to call him. I tucked the card into the frame of the mirror over my dresser. I did not want to forget to call on Monday when he would be back at his desk. I wanted very much to see him again.
We were ready to go out by 10:00AM, and the elevator whisked us to the street. Another womanly adventure lay ahead!
We hailed a taxi, and I got in first to slide across the back seat, so Margo could get in. I glanced at the driver, and caught him trying to sneak a peek up my skirt in the rear-view mirror as I passed along the seat. I was in a good mood, so I let my legs spread, and my skirt to hike up just enough to give him a flash of my thigh above my stocking top. He took it all in. I wonder what he would have thought if he had known that a little higher above that stocking top, my penis was neatly tucked away protected by my panties. He just got a very pleased look on his face, and said, "Where to, ladies!"
The cab weaved its way through the usual crush of midtown New York City traffic, and soon deposited us in front of "Macy's" at Herald Square. I treated the driver to another peek up my skirt as I slid out. He grinned appreciatively. I liked being a tease!
Margo led the way into the store. Macy's was its usual hubbub of activity, but soon we had shopping bags full of bras, garter-belts, blouses, skirts, stockings, dresses, jeans, shoes, make-up, and jewelry. We spent about $300.00 in all. "Just get your dressy things here," Margo advised. "We can get the everyday stuff cheaper else-where." We walked out of the store loaded, and walked up 34th Street to get some of that "everyday stuff" to add to our load.
Our last stop was a wig shop on 5th Avenue near 35th Street. Margo seemed to know the owner, and introduced me to him. "Bobbi, this is Ira," she said. "Be very nice to him. All the girls like us get wigs here." Ira was about 55 years old, smelled of old cigars, and was rude enough to give my bottom a good feel while I looked at the wigs. Margo gave me a signal that I should not protest the intimate touch, and Ira continued feeling me up all the while we were in the shop. I tried to pretend not to notice, but it really bothered me quite a bit!
When Ira rang up the sale for the two wigs I bought, I saw why Margo had motioned to me that I should not complain. Ira had marked the bill "Shopworn", and taken 60% off the price! "He gets his jollies feeling up any Drag Queen that comes in," Margo said when we were back out on the street. "He's a pig, but it saves you some money." I was learning a whole new set of ethics on my way to becoming a woman.
The taxi deposited us back at our apartment, and we took my purchases inside. It was all we could do to carry it all. I had spent almost $500.00, but now I had a woman's wardrobe. I could live now as a woman full time if I wished. All that remained was to be able to have a job, and support myself as a woman.
That was what I wanted then above all else in the universe. I had never felt comfortable as a male. It took me a long time to figure out what was wrong, but now I knew. My childhood had started out normally enough, but I was never really interested in the things that the other boys in the neighborhood were.
= = * = =
I found sports boring. My father could never understand this, and showed his displeasure by all but ignoring me as I was growing up. When I was about 14 years old, I even tried to cultivate an interest in some of the things he liked in an attempt to get closer to him, but he put down my lack of knowledge of those things, and managed to strain our already tenuous relationship even further. I was just not what he wanted in a son.
If I did not get on well with the boys in the neighborhood, I did enjoy playing house with my sister and her girlfriends. The girls liked it because that way they had someone to play the "daddy", but I loathed that role. It did not suit me at all, but at least I was in the game that way. I did not know what was wrong with me. I only knew that I was different somehow, and that I did not seem to fit in completely with the "normal" groupings of childhood. I was 15 years old when I began to realize why.
I had only been 15 for a few months, but I already considered myself enough of an adult to act on my own. Apparently my parents agreed too one day when I found myself left alone at home. I had a slight cold, and I had talked my mother into letting me stay home from school. My father was at work, of course, my sister was in school, and my mother had to visit her sister in a hospital some distance from where we lived. "We're giving you a big responsibility," my mother announced as she was leaving. "Take good care of the house. I'll be back around three fifteen." With that she pulled her coat on, and left. I was alone.
I glanced at the kitchen clock. It was 8:30AM. If my mother was not due back until about three that left me six and a half hours to amuse myself on my own. I had not had breakfast yet, but I was not really hungry. I wandered through the house aimlessly looking around the rooms. There must be an instinct to do that in all of us. Sort of like some primordial animal surveying a new territory.
I stepped into my sister's room. I looked at the dolls lying about, and picked one up. This was the baby doll that we used when we played house. I had cradled it in my arms as its "daddy" many times before, but there had always been a little girl around to take it away from me. Today, however, I could hold it for as long as I liked. I vaguely thought about how much I liked being its "mommy" for a change, and noticed my sister's robe lying across the bed. I touched it, and thought, "Why not"
I stood and removed my pyjamas. I was naked in my younger sister's room. That was Freudian enough, but nothing compared to what was to come. I picked up the robe, and found a "baby doll" nightie underneath. I gazed at it for only a moment before I caught myself stepping into the panties, and pulling them up my legs. I had a little trouble getting my penis into them. It stood out rock hard from my body, and I had to lay it back against my tummy. I slipped the top of the nightie over my head, and felt the cool nylon fabric caressing my torso as it floated down over me. My nipples too were now erect, and I could just make out the outline of their little nubs poking into the fabric when I looked in the mirror.
I tugged the robe around me, put my feet into a pair of fuzzy slippers, and trembled all over. To this day I find it difficult to describe what I felt at that moment. Something changed in me. I felt real and alive at last! As a boy I always felt as if I were acting a role in costume in some strange play. This was different. I was normal, the way I should have always been. I picked up the dolly, and went to the kitchen for my first breakfast as a girl.
After breakfast I went back to wandering the house in the robe and nightie. This time I stepped into my parents' room. It was strange being there especially dressed as I was. This room had always been the inner sanctum of the whole house. As children we might run roughshod through the rest of our home, but we always stopped at the door to this room, looked in, and waited for specific parental permission to enter. There was something almost sacred about it. It smelled lightly of "Old Spice" and my mother's perfume. I walked slowly around the room taking it all in.
I stood before my mother's bureau. I was pretending to be the "mommy" of the house, and I wondered what a real mommy might keep in the drawers. I opened one, and saw a delicate pile of silk and lace. I took out a pair of my mother's panties, and held them up to look at. I knew at that instant what I had to do. The clothing of a little girl that I wore would suit me no longer. I was 15 years old, and enough of an adult to be left alone in the house for the day. Only the clothing of an adult woman would do.
I may have never been comfortable as a boy, but I could now feel comfortable as a girl. I needed to know if I could feel comfortable as a woman! Was this what I had been yearning for all of my 15 years I only knew that it felt right, and that it had aroused feelings and emotions in me that I wanted to explore!
I placed the panties on the bureau, and returned to my sister's room. There I stripped off the robe, nightie, and slippers, and placed them on the bed as I had found them. I picked up my pyjamas, and took them to my room. Then I returned to my parents' room, and stood in front of the bureau looking into the mirror at myself. I was nude, but I still clutched the dolly. I was about to go from little girl to woman. This baby doll was about to start growing up!
My hand fell to the panties on my mother's bureau, and I picked them up. I examined them slowly. They were white nylon with white lace panels at the sides. I swallowed hard, stepped into them, and pulled them up about my hips. The nylon felt cool against my skin. I felt a rush of excitement flow through me. They felt good! I looked down to see my penis straining against the filmy material. I pressed it up against my tummy, and looked into the open drawer.
My hands found a white nylon bra that almost matched the panties. I slipped my arms through the straps, and reached behind me to fasten it. I had some trouble with the catch at first, but soon had the bra secured around my chest. My tiny male breasts did only a little toward filling out the C-cups, but a couple of pair of stockings did the job nicely. I looked down at my brand new breasts. I wished in my heart that they were real!
After a moment of looking, I found a garter-belt and stockings. The garter-belt was soon around my waist, and the elastic top helped to hold my penis back against my tummy. The stockings were more of a problem than I expected, and it took me a while to figure out the best way to put them on, and hook up the garters. I managed to put a run in one of the stockings in the process, but I was too excited to care!
I looked at myself in the mirror standing in my parents' room wearing my mother's lingerie. I was far from beautiful. In fact I looked rather ungainly, but things felt right! I could not explain it, but in that lingerie, no matter how bad I looked, I felt like I belonged at last! Male clothing had always seemed heavy and encumbering, but these light whisps of nylon and lace made me feel alive! I had now to finish the job.
In the drawer was a white nylon half slip with lace trim. I put it on, and looked in the other drawers. They were filled with all sorts of pretty things. I wanted to try them all! I finally settled on a knitted pink top, and slipped it over my head. It clung deliciously over my breasts, and I took a moment to admire the way they looked in the mirror before moving to the closet. I had seen into my mother's closet before, and I knew what I wanted next was there. I quickly located the white skirt with the pink belt. I had seen my mother in this outfit before, and I had always liked it. I wanted to see how I looked in it.
At the bottom of the closet were the shoes. I took out a pair of white pumps with four inch heels, and tried them on. They were a little tight, but I could get into them. I stood unsteadily on them, and my eyes found the blonde wig on its form on the closet shelf. In a second it was on my head, and I returned to the bureau for a look.
In the mirror was a strange sight. There was a strange blonde girl staring back at me. She was rather plain, and perhaps not the prettiest girl I had ever seen, but the realization that she was me made my heart skip a beat! I had seen myself in mirrors before, but I had never paid much attention to the way I looked other than to ensure that my hair was parted properly. I looked the female me over very carefully.
The first thing I noticed was that my face appeared rather plain for a girl. It took me a moment to realize that it needed make-up. I looked down at the bureau, but saw nothing like what I thought I needed. I started looking through drawers. Soon enough I came upon the drawer where my mother kept her extra make-up. The tubes, bottles, jars, compacts, pencils, brushes, and boxes were a mystery. I spent quite a while sorting through them before I got an idea of what they were all for. Then I had to chose a color scheme. Since the outfit I was wearing was pink and white, I chose shades of pink. I decided against using nail polish then thinking that it would be difficult to remove before someone else came home.
I applied the make-up the way I thought it should be applied. I am sure that I looked nothing short of grotesque, but maybe it was not all that bad after all. I do know that I looked very different when I was finished, but I also felt all the more female. I felt the way it seemed I should feel. I knew in my heart that this was right. It was now 11:45AM. I was starting my first day as a woman, and I had almost four hours of it ahead.
I spent quite some time just looking at myself in a number of mirrors. I wanted to see my new female incarnation from as many angles as possible. No matter what view I took, I liked what I saw! Gone were the shapeless clothes of my male self! Gone were the angular male features un-softened by make-up! Gone was the feeling of rough wools and cottons against my skin! Gone was the lanky boy who never could fit into the role into which he was cast by some perverse misalignment of genetic material!
In his place was the soft female form into which he should have been moulded from the first. The feeling of satin and lace caressed her delicate flesh. The subtle shadings of her make-up blended her features into a soft balance. The clothing fitted and enhanced her form to set it off at its best.
I felt wonderful! It did not matter that I would probably not have passed as a woman on the street that day. I knew that such things would come in time. All that I cared about was that I had found the real me at last! The best part of that was that I liked HER!
When most people consider making major changes to their lifestyle, the first things that they picture themselves doing are the things that appear to be the most spectacular, or the most fun. I had just made such a major change to my lifestyle. Indeed, visions of dancing until dawn in a long sequined evening gown flowed through my mind. Even at that moment I could picture myself doing it. What really happened, however, was something much more mundane. I went downstairs, and made myself some lunch. It was such a simple thing, but the doing of simple things that day affirmed and validated the woman that I had become. The spectacular is usually done by a character in a dream, but the mundane is done by real people every day. I was indeed real as a woman, and I did those "every day" things to prove it.
Doing all of those mundane things made me feel very good indeed. I walked all over the house just to listen to the click of my high-heels as I walked. I moved in the chair and on the sofa in the living room while I sat watching television just to see the different ways that my skirt as I changed position. I bent, twisted, and moved in as many ways I could think of to catch glimpses of different parts of my now female anatomy in different ways. I did all that I could that a woman might do that day. I had a lot of time to make up for.
I liked the way that my female clothing felt. By 1:30PM, I was becoming sexually aroused by that fact, and all that had happened that day. Somehow I found myself back in my parents' room staring at myself in the mirror. I wondered what would I look like to a man. I slid my skirt up to expose the creamy skin above my stockings. I liked how that looked! I did it again. Soon I was sexually teasing myself in the mirror. My hand went to the zipper at the back of my skirt. I undid it, and slid the skirt to my feet. I was doing a striptease for myself, and I was enjoying both sides of it!
Before long I wore only panties and bra, and I lay down on my parents' bed. I had never layed there before. It always seemed almost sacred. This was where my father fucked my mother! I looked down my body to see my penis straining against the thin panties that I wore. It seemed to harden even more with the thoughts of them together here! I touched it, and a shiver ran through me. I rubbed at the bottom of the head with just the tip of my middle finger like a woman masturbating her clit. My breath came in excited gasps. I bounced my ass on the bed thinking of what it could be like to have a man fucking me! My release was copious. I came in long spurts. It soiled my panties, but I did not care. I had found what I should always have been!
The clock said 2:20PM. My mother would soon be home. I arose, and took off the bra and wig. I carefully placed everything back where I had found it. Then I went to my room for a robe, and went into the bathroom. I was just starting to take off my make-up when I heard my mother entering the house. She called to me from downstairs, and I ans- wered that I was going to take a bath. I got the last of my make-up off when I realized that I was still wearing my panties. I slipped them off, and held them up for a look before putting them into the pocket of my robe. My mother would think that they were lost in the laundry. They really were my panties now!
= = * = =
Margo and I plopped into two chairs in the living room of the apartment we now shared. Boxes, bags, and packages from our shopping spree to get me a complete female wardrobe lay all about the room. I was tired! I kicked off my high-heeled shoes to give my feet a rest. I knew Margo wanted to go to "The Gilded Grape" tonight as she did every Saturday night, but I was not sure that I was up for it. I did want to wear some of my pretty new things, and I liked the atmosphere of the club, so I knew that we would wind up there.
"Well, Bobbi," said Margo at length, "shall we put these things away" It took me a moment to gain my feet, but soon we were in my bedroom with all of the parcels. Margo sat on the bed opening things, and passing them to me to be put away. I only had a minimum of male clothing there. Just enough so that I could work at my male job until I could find work as a woman as I knew I would, and that clothing I kept tucked away in the bottom drawers of the bureau. There was plenty of room for the things I had just purchased.
"We should get ready to go out soonbbi," saidMargo said as the last soft and lacy piece of my new feminine attire was gently placed in the drawer. "All rightaidwas all I said in response. I was tired, but I sort of did want to go out. I had to live in male clothing all week at my job, so I relished every moment I could spend as a woman. Margo worked as a woman as a clerk in a store, and I too wanted a job as a woman. That all made the time that I could spend in a dress all the more precious to me. I knew that a shower and a change of clothes would perk me up enough to go out.
There were two other problems to going out with Margo that evening. Margo liked going to "The Gilded Grape" on Saturday nights, and Margo liked going to "The Gilded Grape" on Sunday, Monday, Tuesday, Wednesday, Thursday, and Friday nights too! The problem was that Margo was an alcoholic! She kept it enough under some control so that it did not affect our situation together then, but it caused quite a number of problems for us later as it got worse. I enjoyed a drink or two at the bar, of course, but I did not want to try to keep up with her drink for drink as she always tried to get me to do.
The other problem was that Margo turned tricks for cash with some of the men who liked Drag Queens that came into "The Gilded Grape" to supplement her income. She had gotten me into doing that once, and I would probably do it again, but I did not want to tonight. She usually took them to one of the sleazy hotels in the Times Square area, so I would have the apartment to myself for a while later tonight when I came home. Bringing a trick up here was reserved for only a few of her special regulars like Frank who we had brought here last week. I just wanted to somehow insure that I could watch television later without having to listen to the sounds of Margo getting fucked in the next room.
I had a word with Margo about all of this while we were getting showered and dressed. I told her that I wanted to try some things on my own when we went out that night. After all, I had been in public for a week as a woman, but she had been with me to advise and direct for every minute of that time. I told her that I appreciated her help, but I wanted to see how I could handle things as a woman for myself. It was as much true as it was a ploy to get around the problems, and perhaps more true than anything else. I did want to feel what it was like to be a woman on my own.
Margo took it well, and went along with it. "So the little bird wants to fly on her own," she joked. "That is fine with me. It's about time that you did! You are as much woman as I can make you now. The rest is up to you!" I knew that she was right. I thought that I was just getting by a couple of problems, but the time had come for me to leave the nest. I was a woman now, and if I wanted to continue being one, I had to go out on my own, and do it.
This Baby Doll was growing up a little more. It had started with the panties from my mother's bureau four years earlier, and this was the third step. For a moment my mind wandered back to that second step in between when I lost my virginity to a man!
It was only about four months after the first time I had dressed as a woman in my mother's clothes that it happened. I was left alone a few other times since that first day in Drag, and each time I headed directly for my mother's bureau to dress. I was getting better at it, and I even seemed to be having some of the same feelings toward things that a woman might have. At 16 years old I was awakening sexually more and more each day, and that sexual awakening was in an attraction to men as sexual partners, and not to women. It just felt natural that way to me.
I fantasized about what it might be like to be seduced by a man as a woman. I would lie in my parents' bed in one of my mother's filmy nighties, and pretend that I was being made love to by a man. I would hold one of my father's king-sized pillows to me making believe that it was my man. I would slide the hem of the nightie up to my belly, and roll onto my back. Then pull the pillow on top of me, and masturbate to climax while bouncing on the bed as if I was being fucked by a man. I wanted it to happen for real! I did not have long to wait.
I grew up in Union City, NJ. Not very far from where we lived was a vacant lot on the edge of the Hudson River Palisades. Looking straight down from the cliff, you could see the entrance ramps for the Lincoln Tunnel. Looking out across the river, you could see New York City. In the lot was the ruins of the foundation of an old building. A few people would sit on the ruins or park in the lot to watch the ships on the river, and just enjoy the view. You could also find a rather treacherous path or two that led down the cliff to some more secluded ledges for sitting and watching. This all amounted to the local "Lover's Lane" in the evenings. I, however, was a daytime watcher, and so was an older man who seemed to enjoy watching me more than the river!
He was about 35 years old, or maybe a year or two younger when we met. He worked a night shift, and sometimes spent the afternoon sitting on the wall, and watching the river like I did after school. I know now that he was cruising almost anyone who came into the lot, bit in those days I was still a little naive to such things.
He was about 6'1" tall with black hair, and looked very Italian. He was well muscled, but with just a tiny bit more tummy than he should have to make his physique perfect. We had talked a few times, so I knew that his name was Donb but not much more about him. I was about to learn a great deal more on that day!
I was sitting on the wall watching a cruise ship dock on the other side of the river when he sat down beside me. We greeted each other, and talked for a while about the ship. While we were talking, a car with a man and woman inside pulled into the lot behind us. Don and I took little notice at firstb but after a little while I turned to see the couple in the car kissing, and the man touching the woman's breast.
Don looked too for a moment, and turned back to me saying, "Do you think he'll get a feel of her pussy too" I replied with only a smile, but as I did I shifted my seat a bit, and touched my crotch. In my youth, I was getting somewhat excited by the scene. I was also thinking of what it would be like to be that woman getting my breast, and maybe my pussy, felt by that man! I knew that I wanted it to happen, but I was not yet able to understand it either.
Don saw what I was doing, and picked up his cue. "Are you getting hard," he whispered to me. I was surprised by his question, but somehow I think I actually grasped that he was propositioning me. I knew that I wanted it to happen, but I did not know what to say next. In a halting voice, I said, "I don't know." "Would you like me to feel it, and see," Don asked in a low voice. Nervously I nodded, and his right hand slowly moved to my crotch.
I jumped slightly as Don's hand touched me. My penis throbbed with pleasure as he held it between his thumb and forefinger through my trousers. It grew harder as he fondled it. My breathing came more quickly now, and I looked up to see him smiling at me. I wanted to fall into his arms, and kiss him right there and then, but we were in public view in broad daylight. I ached for more of what was happening to me!
"Yes, you're getting a nice hardon there," Don said. "I live in the apartment house down the street. Would you like to get a little more comfortable with me" I needed no further encouragement. I wished that we were there already. A quiet "Yesidwas all I said, and we were off. I glanced into the car as we passed. The man had his hand up under the woman's skirt now. She and I were both getting our "pussiesidfelt that day!
Don and I were soon in his apartment. I hoped that he would take the lead in this, for I was not sure of what to do, or what would happen in this, my first time! I need not have worried. Don sat on the sofa. "Strip for me, honey!," he ordered. I slowly took off all of my clothes, and stood nude for him to look at. I could see the bulge in his trousers, and yearned to touch it. I walked to him, and he reached up to play with my now fully erect penis. With it in his hand, I sat down next to him.
Don's arms enfolded me, and we kissed a long probing kiss. I had never kissed a man in that way before, but it was wonderful! I matched every movement of his tongue in my mouth with a response from my own tongue. Then my left hand dropped to the lump in his pants. It felt huge! Much bigger than my own penis, and I felt that I had to know what it was like. "Mmmm!," Don murmured. "You're a hot one, honey! I like that. Come on!"
Don stood and pulled me to my feet. Standing, he took me in his arms for some more kissing and feeling. I could feel the hardness of his cock pressing into my naked thigh through his pants. He broke the clinch after a few minutes to take my hand, and lead me into his bedroom. I did not resist. I wanted him to have me as soon as possible!
In the bedroom, Don turned down the double bed, and then took me into his arms for another kiss. Then he lay me down on the bed, and stood over me. He stripped off all his own clothing as I watched. The curly black hair on his head was matched by a forest of curly black hairs all over his body. To this day, I am most turned on by men with hairy chests.
At last Don removed all but his briefs. I stared at the bulge in them. I knew what was making that bulge, and I wanted to take it in every way that he wanted to give it to me! I stared even more when he stripped away the underpants, and I got my first good look at his cock. I thought it was one of the most wonderful cocks I had ever seen. It was about seven inches long with its straight slender shaft ending in a beautiful circumcised head. I had to touch it!
Don lay down on the bed next to me, and took me in his arms. My hand touched him on his ribs, and began to make its way downward on his body. As we kissed in that sensuous embrace, it reached his hip. I liked the feel of Don's flesh, and the warmth of his body pressing close to mine as I lay in his arms. Something about all of this felt right to me. I had only felt this way before when I was in Drag in my mother's clothes. I felt like the woman I was in this man's arms. I closed my eyes to better savor his probing kisses, the touch of his hands on my body, and the feel of his skin against mine.
I moved my hand a little further down, and felt the first brush of his pubic hair under my fingertips. I played with my fingers in his curly black bush causing Don to writhe a bit with pleasure. His hand had been caressing my penis all the while. I wanted to return the favor, but I was hesitant. I was having the normal virgin's nervousness about Don's. I wanted very much to feel it. I wanted to hold it in my hands, and get to know every inch of it. I knew that I had to do it. I mustered all of my courage, and my hand moved lower.
My hand then touched Don's cock! A shiver of pleasure ran through me, and Don moaned in ecstasy. I had, of course, touched my own penis innumerable times before, so I expected this to be the same, but it was not. I do not know why. A cock is a cock, and basically all men's sexual hardware is similar, but Don's cock did not feel like my penis. I liked the way it felt, but it felt different.
I played with Don's cock for a very long time, and felt it grow long and hard in my hand. I was enjoying this. I ran my fingers all over his cock, and rolled the shaft between my palms. I weighed his balls in my hands, and gently kneaded his scrotum. I let myself be guided by what I knew I liked to have done to me, and by my desire to explore all of this man. I was caught up in the experience! This is what I wanted. I knew the woman I was from the times alone in Drag. I would now be able to fulfill the full potential of that woman with this man. He was welcome to every part of my body in any way that he wanted it. His pleasure was all I was for at that moment.
Don then moved to take his full pleasure with me. "I want you now!," he growled into my ear with an urgency I had never heard from anyone before. He gripped me tightly, and rolled me onto my stomach. "Hold still!," he ordered, and I felt a cold lump of Vaseline squirt onto my asshole. I flinched at first but wiggled my ass in anticipation of my imminent deflowering as I felt Don's fingers rub the jelly into my anus.
Then there was something other than a finger at my ass. I immediately knew what it was, and I let out a small prayer that I could take it enough to satisfy my man. I felt Don push at my tender, young, virginal bottom, and felt my flesh spread as he forced his way deep inside of me! I felt as if I was being impaled on a peg as my asshole spread wider and wider to accept him into me.
It hurt! It hurt like nothing I had ever felt hurting before, but it felt very good at the same time. The spasms of pain rippled through me, but soon subsided to a level that I could ride along with the ripples of pleasure that alternated with them. This was what I had wanted, and now I was getting all that I had hoped for!
Don rode me for some minutes. I reveled in every stroke, and gasped in ecstasy every time he drove that wonderful cock of his into me. I wanted it to go on for a very long time, but then there was something different in Don. His movements became erratic, and his body stiffened noticeably. He drove his cock deep into my bowels with a violence I had not felt from him before. He groaned a deep guttural growl, and I felt the warmth of his cum filling me! My man had cum inside of me! I had been well and truly fucked! I had lost my virginity!
After a while, Don rolled off of me, and lay beside me on the bed. He pulled me to him, and kissed me again. I looked at the time, and realized that I had to get home for dinner. I dressed quickly, kissed Don in good-by assuring him that I would seem him again soon, and headed for home. My ass squished a bit while I walked. I thought about my first fucking all the way home, and on into that night. This baby doll was really growing up!
Margo was staring at me from the doorway to my room. "Are you coming," she asked. I snapped out of my daydream, and replied, "Yes! I'll be right with you!" I had finished dressing, so all there was to do was slip my wrap about my shoulders, and leave. Margo and I were soon on the street, and headed for "The Gilded Grape" again. I was a woman now in every way that I could be at that point in my life. I was enjoying it, and I wanted more. I would soon find just that!
We spent a good deal of the first few months of living together in that sort of routine. A lot of my life at this time revolved around "The Gilded Grape", and the people that I met there. Margo would go there almost every night, but I tried to hold it to just weekends with an occasional foray in the middle of the week. It was not that I did not like the place. I just felt that I had more things to do on my way to becoming all the woman I could be than just hanging around in bars with the other Drag Queens.
I had a long way to go on the road that I had chosen for myself. I wanted to be sure that I was doing it the right way, and the Gay and closet-Gay men and transvestites in there were not the ones that I wanted to do it with. There was another life that I wanted, and that was where I fitted in with people like the woman I was.
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