After my mother died, we had to leave our house and I ended up living in the apartment above my fathers shop. My sister had left home and my father remarried and moved out. By this time I was a teenager and I decided to stay in the apartment . That meant that I was left alone at night, a fact that gave me time to indulge in my secret passion: dressing up, trying on and wearing the dresses and skirts I found in the closet and every storage box in the attic. I began to experiment with cosmetics as best I could, and being a slim teenager I developed my ability to become the woman I wanted to be- and there was no doubt that I passed very well indeed. But there I was, all dressed up and nowhere to go.
During this period of my life my main transportation method was hitch hiking, which in those simpler days was the normal way to get around. Once when I was about 19, I was returning north from a trip to London and as usual I was trying to hitch a ride by the M1 motorway. I had been there about 40 minutes when a dark blue Jaguar pulled up and a (cute) guy about 32 leaned over and asked me where I wanted to go. I shared my intended destination and he said 'fine, hop in' so I did.
He was heading north to a destination about 10 miles short of my own, so I settled in to the lush leather seats and silently thanked the higher powers for bringing me such a plush ride- so far , score 1. It was only thinking back later that I realized that in an amazing cliche, the radio was playing the Kinks 'Lola'. Later I would learn how appropriate that was. His name was Terry and he told me he was heading home after a few days on business in London. We engaged in small talk for the next few miles. He was easy to talk to and really friendly. He asked me to reach back into the car to get a map, and as I did so I dislodged the bag on the back seat which fell to the floor. I scooped up the contents and noticed a copy of a TV magazine featuring a beautiful young TV on the cover. For a moment I was transfixed- I had never seen such a thing . I was frozen- not wanting to appear inquisitive and yet bursting to dive into the forbidden pages. He must have noticed as he glanced around and in a carefree manner he said
"There are some 'Tranny Mags' in there if you're interested, feel free to browse" as though it were a menu arriving to order lunch. I was dumbstruck and frozen like a deer in the headlights. I desperately wanted to explore that magazine but I couldn't move. My whole life to this point had been based on hiding this desire and now here I was in a situation that was very new. I needed to advance carefully.
"I ... um... er.. well I ... could, er...maybe ... " I uttered gracefully. He shot a look in my direction and a sly smile appeared on his lips. His tone now had become much softer and , well ...supportive.
"It's ok if you want to have a look. I like transvestites- no big deal. You know what a transvestite is I presume?"
" oh yeah " I mumbled trying desperately to cover my ignorance. As it happened I had come across the term a few days earlier in the newspaper reporting on sex change operations in Casablanca. Transvestites had been transformed into women and as their beaming smiles shot from the page I was introduced to the word. Whatever it meant the view of these delicious women on the page was enhanced by the knowledge they were men and I wanted to be there with them- somehow.
The next few miles were driven in total silence as I thumbed through the forbidden pages. From each one, the faces of pretty transvestites stared back, inviting me into their world of feminine allure. Terry's voice snapped me back into reality.
" You like ?" he asked. The moment of truth. Should I say anything? Should I break my own rule to 'never ever say anything to anyone'. As usual , all I could do was stammer.
"I....um .. I think they are..... well... " I flushed beet red. I wanted to tell him about my own desires , about the fact that I too felt comfortable in a dress and hi heels. But all that would come out was a mumbled response.
" I 'm not sure what to say " I offered up finally. Terry was seemingly amused by my apparent torture. He smiled and told me not to worry. Somehow I think he sensed my suppressed desires but valiantly held back.
"Look" he said finally. "I'm having a party at my place this evening. Why not detour and come on over and hang out. I have a few close friends coming over. It's no big deal and I think you might enjoy it".
I accepted immediately. I wasn't in any sort of mad rush and I liked this guy. He made me feel comfortable and there was the tranny thing. I didn't quite know what it was but I was intrigued and I wanted to find out more.
For the next ten miles or so we chatted and laughed at each others dumb jokes. Finally we pulled into a secluded driveway which lead to a beautiful old house that sat in it's own grounds. Terry pulled the car up to the front door and killed the engine. He turned to me and said
" Well here we are. It's not much but I call it home. Give me a hand with the bags and I'll show you your room".
'My room?' I thought, having expected to sleep on a couch. He took my bag into the front entrance hall and headed for the staircase that led to the upper floor.
"In here " he motioned, pointing with the bag to a doorway at the top of the stairs. The room was nothing like I expected. An overall Lilac shade greeted me as I took in an old oak bed in the middle of the room covered in layers of expensive duvets and pillows, all with a matching lilac floral pattern. On the opposite wall was a dressing table and mirror on which were placed a variety of grooming tools, hair clips, jars filled with cotton balls and so on. Overall the room had a very feminine feel and I instantly felt comfortable. Terry motioned off to a door on the opposite wall and indicated a bathroom. I had never seen such a thing as a private bathroom off the bed room and my wide eyed expression must have indicated as such.
"Don't worry," he said "This room used to belong to my sister but she doesn't live here any more. Go ahead and use anything you want to. There are even some of her clothes in the wardrobe" he said winking. That took me by surprise and I glanced back on a double take I saw the door closing as he left the room.
"Get situated and then come downstairs and we can have a drink" he said departing.I took but a few minutes to get 'situated'. I wasn't carrying too much with me as I had been on the road for some time and most of what I did have was ready for the laundry. I wondered what I would wear for the party that night. I followed Terry downstairs and into the spacious kitchen and was greeted by a welcome glass of beer. Terry already had a glass of wine in hand.
" Come on in , make yourself at home " he said and I complied. We sat around a large kitchen table and chatted about this and that and before long an hour had passed. Terry was by this time the better side of two glasses of wine and was waxing lyrical. He talked about his life growing up in Sheffield, a scruffy Yorkshire steel town , how he escaped to London to become a fashion photographer. Things had not gone the way as planned and somewhere along the line he had started to do his own hair and makeup and to cut a long story short, he now made a very good living doing hair and makeup for other photographers. I didn't have much to add to this. I was still young and had no clear idea of where I was going or how I was going to get there. Terry once again asked me if I had a girlfriend and once more I told him 'no' I didn't.
"Do you mind if I share something with you " he asked.
"No, of course not" I replied. By this time the beer had had a smoothing effect on me and I think I was ready to hear anything.
"When I was younger, I enjoyed wearing women's clothes" he said in a matter of fact way. He sat back and let the words sink in, a comfortable smirk on his lips. I could tell that in some way the words had formed as a challenge, but I was too dumbstruck to fully take advantage at that time.
"Wow" was all I could muster, and then what seemed to obvious question "Do you still do that ?"
"Actually no, well, lets say not as much as I used to. For a while there I was contemplating going full time." He chuckled.
" A sex change? " I asked
"No, well not exactly. For a while I would go several days in 'drag' and not even think about it. Of course in those days I was a slim teenager, not unlike you are now, but eventually my body had a testosterone explosion and developed in more masculine ways and now it doesn't quite hold together like it used to. I might dress tonight but it's a special occasion."
"Tonight ? " I spluttered. "What do you mean?"
"Didn't I mention it " He said nonchalantly. "The party tonight has a drag theme" He turned to me and looked me in the eyes." I think it would be really great if you would let me dress you for the party. You might even enjoy it" he said playfully.
Enjoy it ? my heart skipped a beat and I couldn't quite believe what I was hearing. He wanted to dress me as a girl for tonight's drag party ? Had I died and gone to heaven? Every ounce of my being wanted to get out of the chair and scream 'YES!'. Unfortunately, I had years of self preservation tied up in a simple rule. Never ever tell anybody that I enjoyed wearing girls clothes. Ever, EVER !! Now, even though I could see that I was in a totally supportive situation I still couldn't bring myself to let go.
" what do you mean ? " I asked sheepishly
" Well," he said, getting up out of the chair and clearing away the glasses. " I think that you would make a really beautiful woman, and I can transform you into such a creature of delight that you will be the belle of the ball, and if you enjoy playing the girl, we can explore much more later after everyone has left. What do you say ? Give it a go?"
My stomach was in knot. I wanted to just say 'yes, of course, lets get started', but instead I couldn't catch my breath and all I could do was to look at the table. Sensing that I was uncomfortable with the proposition, Terry became very conciliatory and started to apologize for being so forward.
"I sensed it might be something you would be interested in" he said, "I thought after you had spent so much time with the magazines that you would want to check it out. I'm sorry. I misunderstood. If you want to leave I'll be happy to give you a ride" He said. It was now or never, I had to throw caution to the wind and take the opportunity. I looked up from the table as Terry was crossing the room to get his keys.
"Terry I would love that." I said. " I can't think of anything I would enjoy better. I have dressed before, in private but I've never told that to anyone else on the planet before. I guess I'm a little nervous. It's not every day I get the offer to transform." I felt a tear well up in my eye and I looked away not wanting to appear weak. "Don't cry," he said, crossing the room and putting his arm around my shoulder. I shook my head as if to say' don't be silly- me cry?' but I was crying, tears of joy and as I turned to him he enveloped me in a bear hug and comforted me. Smoothing away the tears he looked at me and said
"You will remember tonight for the rest of your life and I'm going to make sure you are the prettiest girl at the party."
Terry left the room to go upstairs and draw a bath for me. I was ready for a bath as by this time I had had several days on the road. In those days I wore my hair long. I had a beautiful mane of black hair that was thick and wavy. I tied it in a ponytail for the most part but that didn't mean that by now it wasn't ready to be washed . As he had promised he went upstairs as I sat and composed myself and wondered what the night would bring. The knot in my stomach had only grown larger by this time and the anticipation of the transformation was almost too much to bear. That alone would have been enough to demand a few moments of inactivity to resolve, but in addition I was rock hard with anticipation. What did he mean by 'we can explore more after everyone had left.' I had never had sex with another man or even had the desire to explore, unless I was dressed and on several occasions I had wondered what it would be like to play the complete role of a girl. If things worked out maybe tonight I would find out. Eventually my hard-on softened enough for me to navigate movement and I followed Terry up to my room and into the en-suit bathroom which by now was full of steam and a delicious perfumed fragrance permeated the air. Terry had plied the bath liberally with bath salts and bubbles and I eagerly stripped off and climbed into the scalding water. It felt so good to be enveloped in the bubbles and I could feel the water softening my skin. I was blissfully hairless in those days and so I only had to worry about cleaning up a few errant facial hairs. I quickly took care of the facial hair with a razor that had been left on the side of the bath and the sat back and luxuriated in the steaming water. I could hear Terry moving around in the other room and finally he put his head around the door and mentioned he had left some skin products by the dresser. He wanted me to call him when I was ready and he would help me apply what was needed. I was too excited to wait and before long I had washed , shaved what I could and was drying myself with a huge fluffy bath towel. I decided I would jump into the role and I eventually wrapped the towel around myself as though I was already a young girl, making sure the top of the towel wrapped around my bust to maintain modesty by covering my breasts. With a smaller towel I rubbed my hair and then wrapped it up into a turban.
"Ok I'm ready " I called out and Terry appeared at the door with a smile on his lips.
"Very pretty" he offered, and I instantly felt myself blushing. "Come on dear, lets get you ready to get dressed" and with that he led me by the hand over to the dresser.
The top of the dresser was crowded with different products. Terry was not at all shy and soon I was covered in a sweet smelling skin conditioner that made my skin feel soft and sensitive. Over the course of the next few minutes I was rubbed, smoothed and generally pampered by my new teacher. He took away the towel covering my body, but sensing my nerves he slipped a silk robe over my shoulders and I reached back into the arms and tied it in front of me. The satin texture of the robe over my freshly shaved and conditioned skin sent spasms of delight racing through my loins. I sat in the chair and crossed my legs so Terry would not see my excited and enlarged member. This resulted in a very demure sitting position which Terry duly noted. Without a pause , the towel was whisked from my head and Terry set about playing with my long hair, fussing and prying with obvious confidence in what he was doing. Pretty soon he had snipped it into shape and piled it high with rows of large hair curlers. Then came the foundation for my cosmetics. He insisted on covering the mirror so I could not see his progress, but it was clear that he was now in his element as I willingly relinquished control to his obvious experience. I sat back and enjoyed as he applied layer after layer of foundation, blush, eye shadow, mascara, false lashes and finally lipstick. He then set about giving me a manicure and a pedicure a process that was less than pleasant, but much needed if the end result was pretty fingers and toes rather than hands that looked as though they had just built a house. Finally I sat in the chair blowing a set of freshly painted false finger nails in a silk robe and my hair in curlers. I still had no idea what he had done. I was about to discover he had changed my world. Leading me by the hand he took me over to the bed where my heart skipped a beat as I spied a collection of sexy lingerie he had laid out on the bed. In matching black satin and lace there lay a pair of exquisite panties alongside a beautiful corset waist cincher and a pair of black stockings. First of all he produced a gaff from the pile of neatly folded clothes and helped me into it, instructing me on how to place my penis in a way that resulted in a flat tummy. Next he helped me as I placed my feet through the legs of the panties and pulled them on over the gaff. He held the corset so I could pass each arm through the straps then gathered it behind me, first fastening all the clips then increasing tension on my waist with the laces. I could feel it getting tighter but before I had trouble breathing he lessened the laces and tied it off.
"Not too much for now" he said. "We can tighten that later if you want." Next he sat me down as he helped me on with each stocking, gathering the material so that my toe touched the end of the stocking first then he rolled each one up to the top of my leg, pausing only to gather the material along the way. Finally he passed the suspenders under my panties and clasped each one shut, capturing a piece of nylon in order to keep them up. Bidding me to stand , he pulled a pair of slinky sandals from under the bed and helped me as I carefully placed each foot into the high heeled shoes. My head was swimming. As always it was the addition of high heels that transported me into the world of Jessica , my feminine persona. Terry however had not yet finished. Pausing for a moment to get his bearings, he glanced over to the drawers in the dresser and in a moment he had a silky black slip in his hand. He again gathered the material and passed it over my head being careful not to touch my makeup. I wriggled and took the material down my body . It was snug but amazingly it was a perfect fit. I looked down at the satin skirt of the slip covering my stocking clad legs and let out a moan of delight. It was too much. I was glancing around for a mirror , desperate to see what wonders had been created but Terry was not yet finished.
"Not yet young lady" he scalded. "sit down and let me finish that hair". Painfully he removed all of the curlers and then started to brush it out. Seemingly changing his mind halfway through he had me stand up as he moved over to the closet. He returned with a beautiful black chiffon dress. I could see why he had chosen a slip. The material was translucent and had there not been a slip anyone could have seen what I was wearing underneath- a fact that didn't exactly bother me at the time. The dress had a modest plunge in the neckline to show off what cleavage I could muster. It was gathered at the waist then flared out in the skirt to rest just above my knees. I eagerly climbed into the bodice as Terry again turned me around and I felt the zip slowly run up my back to close at the top and seal me into bliss. Smoothing the skirt I sat down and crossed my legs. I could feel the two layers of nylon connect and felt the silky softness of that materiel. I couldn't help the urge to caress my leg with my hand. Terry continued to brush out my hair, teasing it into position as he worked to make it perfect. Finally, the moment was right and as he offered his hand and led me to the center of the room in front of a full length mirror covered with a sheet.
"Voila !" he cried , whisking the sheet from it's perch. I was stunned. Before me stood the most convincing and beautiful woman I had ever seen. My hair was falling in long curly waves, gathered in away that left no doubt as to the feminine intention of the style. My cosmetics were applied to perfection, he had stayed in a pale spectrum to contrast with my dark hair and dress and so the face of a pale, demure girl blinked out from under huge eyelashes. It was as though the dress had been designed especially for me. It clung to my body until the waist then fell to my knees in a beautiful gathering of material. I was speechless. I looked at Terry as though not quite comprehending as he smiled back, obviously proud of his accomplishment. I twirled back and forth making the skirt fly. I was truly in heaven."Ok nearly finished " he said crossing to the dressing table. He grabbed a small box and returned to where I still stood transfixed in front of the mirror. " Here try these" he said, attaching a pair off dangly earrings to each of my ears. Luckily it was the fashion to have pierced ears at that time so I had no trouble attaching the ear rings. Next he pulled out a gorgeous matching necklace of what I took to be feaux diamonds set in white gold. It was not until much later I learned that they were real diamonds. He turned me around and as I looked into the mirror he fastened the clasp behind my neck. It was perfect. The earrings and the necklace were indeed the finishing touch and I let out a gasp. I had no idea I could ever be so beautiful, and any apprehension about attending a party of strangers lifted away."Ok my dear" said Terry. :"Now it's time for me to get ready so if you will excuse me I'll be back shortly. Take a look around the closet area and try to find a purse you might like then relax. And don't mess up that makeup young lady !".
I was expecting Terry to return in a dress and heels but I was startled to see some time later that he had changed into a black suit with a ruffled shirt open at the collar. He looked very sexy and sophisticated. For some reason this made me feel slightly uncomfortable. I had assumed we would attend the party as sisters, or at least lesbian lovers, but now it was clear things were unfolding against a larger design. Terry must have sensed my apprehension. Taking my hand in his he sat down opposite me and began to speak in a soft tone.
"what's the matter" he asked "why so blue?"
" I'm Ok" I blurted" it's just , well I thought we would all be dressed. You had mentioned that you dressed as well- I just figured we would all be dressed. I just don't think I can do this if I am the only one dressed. I've never done this in public and, well frankly I'm a bit nervous."
"Of course you are- wouldn't be human if you weren't , but don't worry. I promise you will be fine and you WILL be the belle of the ball. I promise". His words were beginning to sound a little hollow. What had I let myself in for? It was one thing to think of dressing up to be with other TV's at a party - fun, fun, fun ! But what had this turned into ? My stomach returned to it's familiar knot and I felt myself become short of breath. In a way it was a feeling that was alarming and exciting all at the same time. I could tell that Terry was empathetic to my feelings, but he didn't back down. Once I had stopped squirming he continued.
"Look, I'm afraid I havn't been entirely truthful. It's true I am having some friends over this evening, they are TV's and we do intend to have a great party." I could feel he was about to add the word 'but...' "But., that's not entirely the whole story. You see, I have branched out into clothing design recently and tonight I intend to show my new line. It's rather unique because it is sized and designed to crossover between the TV lifestyle and regular women". He said pensively. " I want to exploit the marketing to play directly both to Women and Transgendered." He said. "I have a theory that most young boys play around with the idea of transvestism but for a variety of reasons they do not pursue it- I think that is one reason why our society frowns so much on it. It's because most of our native sons would rather be in heels and makeup for at least some part of their lives. Other cultures are not so condemning of the lifestyle and in India and Thailand it can be a badge of honor to have a Katoy as part of the family. Hell, in India they are respected members of the community." I didn't really care about what happened in India or Thailand (not until later when I found out how cute Thai katoy can be). What mattered to me was how the hell I was going to manage all of this. Why was I here?
"why me ?" I asked somewhat forlorn.
"I knew it had to be you when I saw you by the roadside this morning. You looked so vulnerable and I thought 'if that guy isn't what I'm looking for then to hell with it..When you picked up the magazine from the back and became so transfixed, I knew. You see, I can't do this with a seasoned transvestite, I need someone who is on the verge of admitting this to themselves, not a seasoned pro who exists behind an attitude that is so complete that nothing can get through to hurt them. I need innocence and you have it in spades my dear. Look at yourself" I cast an eye towards the mirror."Look how beautiful you are, and don't tell me you are eager to get out of that dress- I can tell- honey, you're a natural" he said gushingly.I knew I was blushing and I also knew I had no power to resist. He was right, I had never felt so comfortable in my life. I felt as though I belonged for the first time I could remember, and although I suspected it was all an illusion, I was ready to comply because deep down, I wanted to please my man.......which in itself was an utterly new sensation and one that left me slightly worried. I knew that if I could remain confident that I could probably pull this off, although that was a tall order. I was wearing delightful strappy sandals with a 4 inch heel which did wonders for my legs although they were a little hard to walk in gracefully. Terry sensed my concern and set about giving me a crash course in feminine deportment. I was an eager student, and in what felt like no time at all I was able to sashay comfortably. Terry was a great teacher- maybe the evening could be interesting after all.
Some short time later the first of the other 'girls' started to arrive. I was introduced as Jessica and that alone. I met each an every one of Terry's friends as they arrived, Amanda was first and arrived in a halter top, jeans and sandals. Terry instantly hustled her into the bedroom and in no time she too was wearing one of Terry's creations from his day wear line. Next he set about piling her long hair into a sophisticated bun and Amada was ready to rock! She was also really friendly with me and As Terry greeted each of the girls , Amanda took me under her wing and explained the way the night would go. First we would model daywear and then finish the night with evening gowns. Some of the models would be TV and others GG. I instantly assumed Amanda was a GG but later I was stunned to learn that she was not only a TV but part time, only really dressing to visit clubs and special friends. At this she winked and I felt my knees buckle. Luckily I don't think she noticed. The rest of the girls had arrived by this time. Nicole, a stunning colored girl was beautiful but distant. Angela had a cold so she was 'here for Terry' and took great pain to let everyone else know how she suffered. Patty was a sweet girl who seemed to be in a similar situation to me, somewhat nervous but excited at the prospects. I later discovered she was the GG of the crowd. Several other girls had arrived but I did not get a chance to meet as by now things had become quite chaotic. Terry was running around gathering girls, sewing seams, zipping up dresses and getting everyone ready. By now I was able to see a distinct style emerging in Terry's designs. His work seemed to fit into a category of retro Fifties wear; cascading skirts, cardigans, sleeveless blouses. All very pretty and very feminine. The girls looked stunning. I hoped I looked half as good.
I stood by the wall with my feet together and my hands clasped in front of my dress, hoping that I didn't stand out. The feeling of my nylons brushing up against my slip and skirt continued to send shivers down my spine. I was having the time of my life. All too suddenly Terry emerged and began to line up the girls. I was number two behind Amanda who turned around , squeezed my hand and gave me a small kiss of the cheek.
"Don't forget to stay confident" she said to me pointedly "Don't let them see you sweat and above all enjoy it- it'll be fun". Good advice although by this time I felt my legs had turned to stone and I was no longer capable of independent movement. My stomach had erupted in butterflies and I could feel myself beginning to well up at the prospect of stepping out into a crowd of strangers. All too suddenly Amanda stiffened her back, stuck out her chin and launched off onto the runway. Polite applause greeted her as she marched down the runway and paused at the end long enough to allow the audience to lust after her long feminine legs and hopefully notice the beautiful dress Terry had put on her. Terry leaned over to me and placing his hand in the small of my back he whispered
" Here you go darling... knock them dead."A soft push sent me in the direction of the runway, and as soon as my foot hit the carpeted deck it seemed my mind went blank and I started to move gracefully towards the end. I was aware of faces looking up at me, but I was not looking at them. I was in a world of my own where I had always been a woman and now I had the chance to display that feeling. Arriving at the end I spun around on one foot while placing the other at a jaunty angle. My hands had found a natural position on my hips and I could feel the skirts of my dress billow as I made the turn. I was aware of a slight gasp from the audience and in an instant I was amazed to hear significant applause and a few cheers. Without missing a beat I turned and walked gracefully but with purpose back to the waiting area. The applause accompanied me the whole way. Bursting through the curtain I was greeted by Terry and Amanda who gleefully congratulated me. Terry gave me a bear hug and as he pulled away he kissed me gently on the lips.
'Well done ..I knew it..I knew you would be perfect." He gushed. One by one the other girls marched out to show their costumes as Amanda took me upstairs to one of the bedrooms. Laid out on the bed and around the room was the most amazing collection of ladies evening gowns. Amanda picked the first one off the hangar, an amazing creation in taffeta and silk. She indicated to the second gown, a black velvet creation that swooped down to the ground leaving a small train.
"You're the girl of honor this evening " she said " You get to wear the expensive dress. Go on in there and let me help you into it then you can help me " I slipped out of my dress and hung it on the clothes hangar the gown had just come off. Amanda held the bodice up so I could carefully place each foot into it, then she helped me wriggle in and closed the clasp behind my neck. The gown felt wonderful. It still suited the earrings and necklace that Terry had given me earlier and so I was ready in no time. I helped Amanda squeeze into her dress and happily zipped it up in the back. It felt so good to be 'one of the girls' and she looked stunning. We returned to the waiting area to watch the other girls and waited for our next performance.
Terry had by now become somewhat frantic. Torn between guiding the girls onto the catwalk and making sure they changed into the correct gowns, he was trying to do too much and I think was missing the fun of the evening. Several people had begun to wonder around the house by now and I was trying to stay out of view as much as possible. My hair had be re-done and was now piled high in a very sophisticated bun with wisps of hair cascading down the side of my head. I was unaware when a voice alongside my ear crooned
"You are the best model I've seen tonight" I was startled by the voice and turning with some alarm I came face-to-face with a handsome man about 30 years old.
"Oh, well.... Thank you!" I managed to stammer, trying my hardest to modulate my voice to a higher pitch without sounding like something from Monty Python.
"Seriously, you just glowed out there. My name is Richard," he said holding out his hand.
"Jessica, and thanks for the compliment. I've never done this before" He started to laugh which instantly made me feel as though he saw through my act.
"Oh that's funny," he said " as if....". He arched his eyebrows as if to question my sanity and I realized he didn't believe me.
"No seriously " I protested.
"Well if that's the truth then I'm really impressed" he replied. " Do you live in London? I guess I'm asking if you would have dinner with me sometime soon?" The question hit me like a brick. I must have turned beet red and shifted uncomfortably. What did I say to this? The guy was handsome but I had never regarded myself as gay and right now the biggest problem I could see was that I wanted to. What was all that about? Luckily I was saved as Amanda interrupted and after an interested glance towards my new paramour, she asked me to follow her.
"Look I'm sorry, I have to go and I don't live in town so I think it might be difficult." I offered as Amanda pulled my arm.
"Take my card and call me then" he said fishing out a business card and carefully sliding it down the front of my dress. I fished it out and held it in my fingers as he disappeared into the crowd. 'Richard Hollister- General Dynamics' it said. I slid it into my purse. Never say never!
It was time for the second round. Amanda once more took the first pass and I followed closely behind. As I paused by the entrance, Terry came up behind me and I felt a hand outline the shape of my butt. Under normal circumstances I may have had a different reaction, but on realizing it was him it sent a shiver through me as he gently placed a mink stole over my shoulders.
"This dress was made for someone elegant and beautiful" he said. "The mink is elegant and you are beautiful so I think we're fine. Again, a gentle push and I was on the runway and gliding gracefully towards the audience. Once again there was an outbreak of applause as I flirted with the crowd as best I could. I turned at the end, paused and then turned again. I could feel the hem of the gown swishing across the floor and as I turned to return to the waiting area I glanced Richard Hollister applauding loudly and with a certain glint in his eye. Did he know? I made a mental note to ask Terry later.
Back in the waiting area the rest of the girls were lined up and ready to go. Amanda came over to where I was standing and gave me a big hug.
"You were fantastic" she gushed." You know you are the star of the show- everyone is talking about 'who the new girl is'. I pretended not to know of course," she said with a mischievous smile on her gorgeous lips. I was in a state of shock and I suggested we try to find some drinks as fast as we could to help me calm down. Just as I spoke a waiter passed with a tray of Champaign and Amanda and I each grabbed a glass. Moments later we were both searching out our second. One by one the girls finished the show and finally at the end we all gathered on the stage as Terry entered to accept a well earned round of applause. It seems the evening was a success. As the applause died down Terry turned to me and took me by the hand, leading me into the throng. I resisted just a little, still nervous that someone would 'read' me. He persisted and I was powerless to protest. One by one I was introduced to Terry's friends, mostly women in black who I assumed were all fashionistas. Each one pointedly asked my name and where I was from and thankfully Terry answered each one saying I was his secret weapon and that we were lovers so don't try anything. I found this to be slightly embarrassing at first, but as the evening wore on and the Champaign started to work it's magic I lowered my resistance and began to enjoy the idea of being the lover of this man. Terry held my hand for the most part except for when I closed in to him encouraging him to take me in his arms. His hand snaked around my back and more than once found its way to softly stroke my butt. His fingers would occasionally find my suspender clasps through the fabric and even though it was just a gentle stroke it made me wild. I could hardly contain myself.
Quite soon after the show people started to leave and before long there was only Amanda and a couple of other girls remaining. Terry was deep in conversation as Amanda came up to say good-bye.
"You were wonderful tonight Jessica and I really loved spending time with you. Can we get together soon? I think you and I need to go shopping so we can have some girly time together and talk about Men". she said finally glancing over at Terry. "Terry, you make sure you don't smother this delightful young girl. Leave some for the rest of us" She laughed and turned to leave. Glancing back at me she said softly "I mean it. You are so gorgeous but you need a woman's touch and that will open a lot of doors for you- if you want them to open." And she was gone. I made a mental note to follow through. She was captivating on so many different levels. I was sure I could lean a lot of things from her and that was part of it. I was also very attracted to he and that was part of it too. Talk about conflicted!
I turned to Terry as the last person left and slowly moved into his outstretched arms. As my hands felt the shape of his lapels, I could feel his hands caress the back of my gown and without thinking our lips met and he kissed me long and deep. I had no resistance and let out a soft moan as his tongue played with mine in a sensual probe. My hands found the back of his neck as our bodies came together in a loving and seductive embrace. I had never kissed a man in this way and although I knew I was in a new place, there was no resistance. It was as though I felt it natural to be doing this after a night learning to accept my feminine persona. I wanted him to kiss me and I too felt a burning desire to kiss him. Breaking away, he took my hand and led me up the stairs, past the door to my room and into the master suite. Holding the door for me, I stroked his chin as I passed, letting the mink stole slip from my shoulders as I entered the room. I crossed to the bed and paused while Terry approached me from behind. His arm passed over my waist as his lips found the lobe of my ear and then the sensitive area of my neck that made me moan again with delight. I could feel the zip on my dress start to slide down and before long I was stepping out of the gown to reveal my deliciously feminine lingerie. He didn't wait for me to remove any more as he pushed me back onto the bed. Our lips again locked in a passionate kiss as his hands explored my satin clad body. I too had exploration on my mind as I tugged at his jacket and then the belt of his pants. It seemed like an instant before I had his huge cock in my hand and I set about stroking the length of his shaft while our tongues did battle above. He was by now beyond restraint as I felt his fingers probe the edges of my panties and before long my own stiffened cock was firmly embraced by his willing fingers. I leaned back and let out a sigh of ecstasy that I thought could never be surpassed. That was until a few moments later when his tongue had left my lips and was now fully engaged in kissing the shaft of my cock. Skillfully his lips gently kissed the shaft starting at the base and working up to the engorged head. I cried out as his tongue slid over the head of my cock and gently descended over the entire organ. I thought I would explode. I had never felt such a wonderful sensation and I became so overwhelmed that small tears started to fall down my cheeks. I was gasping for him to stop - afraid that an ejaculation at this point would render me useless for the rest of the evening. Terry sensed my condition and pulled back just as the first few drops of pre-cum emerged from my glistening pussy stick. I managed to hold back the rest, and felt a compelling urge to return the compliment. Terry didn't take too much persuading. Laying back his huge cock beckoned me and I was only too happy to comply. I borrowed his technique of slowly kissing the shaft from the base until after a few minutes his entire cock was in my mouth. I slowly worked it in and out, each stroke taking it in a bit more until it was in my throat. I tried to take it in too far and suddenly gagged and had to stop for fear of vomiting.
"Don't worry, I've got you" Terry instantly whispered. We rested for a few minutes while I regained my composure. I lay back in Terry's arms while he stroked my hair. Before long we were both kissing again. The gagging moment had passed and my own erection reminded me that I had managed to stop the ejaculation. I was ready to go again. Terry momentarily pulled away and grabbed a small vial from the side table.
"Try this, " he said, unscrewing the top and holding it up to my nose.
"What is it? " I asked, somewhat alarmed.
"It's poppers" he said" I promise you will enjoy this." By this time I trusted him completely and I breathed in the chemical smell as he held it to each nostril. I became light headed as Terry too took a hit but was unaware of the influence of the drug until our lips met once more. Instantly I was lost in the most passionate kiss I had ever experienced. Our mouths were locked for what seemed hours as the effect of the poppers flooded through my brain, ignighting a passion I never knew I had. Unfortunately the effect wore off too quickly. I reached for another blast but Terry grabbed my hand "Not yet, if you take too much of it loses its effect and leaves you with a horrible headache. All good things in moderation. He rested for a while to let the effects of the poppers wear off. I lay with my head on his chest listening to his rhythmic heartbeat. As he dozed I played with his semi erect cock, marveling at the situation and somewhat alarmed by the fact that I was enjoying it so much. Terry stroked my hair and I could see form his cock that he was slowly re charging to go again. I leaned down and took the head of his cock between my lips and he let out a contented moan. Before long our lips were locked in passion and I could feel the hardness of his cock against my soft belly, moving rhythmically against me, little drops of pre cum softening the contact. My own cock again felt as though it would burst. The closeness of his body was driving me wild, but most of all, his manner was seducing me into a world I had only imagined. This was what it really felt like to be a woman. His gentle touch caressed my willing thighs and I gave myself to him completely. As he nibbled my ear lobe and again drove me crazy, he whispered into my ear
" Ready to pop that cherry" he asked.
"I'm ready for whatever you want to do my darling," I crooned back to him. Puling away for a moment he reached to the side of the bed and grabbed a tube from the bedside stand.
"Turn over" he commanded and I was only too willing to comply. Slowly he took a glob from the tube and began to massage it into my boy pussy. The sensations as his finger slid past the sphincter muscle shot through my body and I gasped at the sudden intrusion.
"This will make it easier for the first few times " he said with a knowing tone. "It's a special lube that desensitizes you so the stretch doesn't hurt so much. Leave it on for a few minutes. I'm going to the bathroom and when I get back it will be ready." And with that he slid from the bed and padded over to the bathroom. As he disappeared inside I took a few moments to catch my breath. Here I lay, in fine silk lingerie, my velvet evening gown strewn on the floor and my pussy lubricated for further engagement. What more could a girl want? I was about to find out.
Terry returned in a few minutes and slid into bed beside me. He kissed my lips and I reached out to him and kissed back. Our tongues once more went at it only this time I could feel his fingers explore my hole. It felt different, as though I was only feeling a portion of what was happening but my excitement grew when I realized Terry was now withdrawing two fingers and the sensation was wonderful. I turned to lie face down but as I did so he caught my arm and resisted my movement. Taking my leg he rested it against his shoulder and taking the other leg rested it against his other shoulder. I relinquished any form of control to him and lay back as he stuffed a pillow under my back. I could feel the tip of his cock pushing against my hole and as it slowly began to penetrate I realized the de sensitizing lube only worked so much. I began to panic as the pain grew and it felt as though he would split me. He took it very slowly and as quickly as it began the pain began to ebb and I could feel his cock inside me for the first time. Pausing to let the muscle adjust he slowly began the rhythmic pulse that would take me to ecstasy. Picking up speed, I began to feel the most amazing sensation as his cock tickled my prostrate. My own cock felt as though it would burst, but my thoughts were elsewhere. He was my man, fucking my pussy as I lay on my back. I had never felt so feminine and I didn't want it to stop.
"Oh god.... Terry this..... is fantastic" I gasped between strokes. "Please..... don't ...stop.." By now each time he thrust his cock into me I responded by arching my back to meet him. I could feel him getting closer and closer and I too could barely keep from shooting my load. In an increasing crescendo Terry began to indicate he was about to cum, and as he did so he reached down and caressed my cock. In an explosion of cum I shot out my load which landed on my chin and face. I didn't mind as my own thoughts were on the fact that I could feel Terry's cum filling my hole and dribbling down my leg. I could taste the sweetness of my own cum on my lips and licked it up in order to swallow it. Terry began to lick it from my face and pretty soon there was non left. I was not done however so I leaned down and liked his cum from the head of his softening cock. His groan indicated he had given all he could. We fell into each other's arms and before long sleep overtook us both.
By the time I awoke the following morning Terry had already risen and I could smell freshly brewed coffee. By now I was naked so I grabbed a blanket and wrapped it around my shoulders. Before I could leave the room Terry stood before me with two steaming mugs of coffee.
"Good morning" he said cheerily and paused to kiss me on the lips ever so gently. "Might I say that was a fantastic evening.. and the show wasn't bad either."I smiled and kissed him again before falling back into bed. "I have to rush because I have to be on a call downstairs in a few minutes. I've laid some fresh clothes out for you so why not get a shower, get dressed and come downstairs when your ready" he suggested , always in control. My own preference would have been to continue where we left off but I turned and drank my coffee as he jauntily left the room. For some reason I had assumed that my girl act was confined to the evening, and so I was delighted to see that the armchair that sat in the room was draped with what looked to be a print dress and some delicious looking lingerie. I couldn't wait to get dressed, but trying to be ladylike I rushed into the bathroom to shower and freshen up. I was meticulous about preparing myself and utilized several 'products 'I found in the bathroom. A liberal application of body cream softened my skin to the touch and I applied perfume and scented cream for quite some time. Returning to the room I slipped into the silk panties Terry had left for me laying on the arm of the chair. Alongside was a bustier that combined a bra and waist cincher and I took great delight in fastening the back alone. Next I gently unfolded my stockings up each leg, making sure the seam stayed straight up the back of my leg. I reached down to grab the dress, and noticed it was a black polka dot against a white background, while the collar and the belt that gathered it at the waist was the opposite print. The bodice fit snug emphasizing the silicone breasts that lay cupped beneath the silky fabric of the dress. The skirt splayed wide to just below my knee, made somewhat full by the lavish petticoat that lay beneath. I suspected it was one of Terry's creations as it had a distinctively retro feel. I loved it and it fit me perfectly. My adolescent girlish features suited the dress and stepping back to view the mirror I knew there was one final addition. I slipped into a pair of strappy sandals and bucked each strap around my ankles. Oh bliss I thought again. Straightening up and smoothing the front of my dress I remained transfixed in front of the mirror. I decided a pair of fifties dangling earrings would work well and I reached down to the jewelry box on the table. Inside I found several pairs, each one then taken out and tried against my ears to find the perfect match. I settled on a pair of simple matching earrings. I stood in front of the mirror for some time teasing my hair into different styles. It seemed as though my new look lacked something and strolling over to the closet I spied a wide brim hat. Taking it out I pulled it down on my head and cocked it at an angle. A pair of retro sunglasses with winged rims completed the Audrey Hepburn look and I could not have been happier. In my euphoric state I probably went over the top as I remember as I left the room my walk developed a definite sashay. I kept it up as I glided down the stair case and into Terry's study. As I entered the door I could see a look of approval cross Terry's face and the feeling I had enjoyed so much the night before was back. I spent the rest of the day in that gorgeous dress and later Terry took time away from business so he and I could refresh our sexual memories. Multiple times throughout the day Terry reminded me what it was like to receive my man and I loved every minute. Finally the time came for me to leave. Reluctantly I changed into drab and Terry gave mea ride home. My life was never to be the same again.