First Night Nerves

(c)Tina & Tim 2003

My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over 3 years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and have always been very slim. I am blonde with blue eyes and very fair skin. Debbie is two inches shorter than me, with long brown hair and a lovely rounded figure, not in any way fat. We both enjoy fitness, dancing, dining out and the cinema.

Oh, I nearly forgot, we're both bisexual and I'm also a transvestite.

Always a slight, somewhat effeminate child, I was bullied mercilessly for much of my schooldays. I was academically bright, but preferred sports like tennis and badminton to team games, a fact that served to increase my torment as participation was never optional. I have always been slim and fair, but this was made more obvious during my teens when puberty seemed to simply pass me by. Despite having occasional girlfriends (as well as some well-concealed boyfriends) for several years, many of the boys still called me 'gay' and sometimes made obscene comments and gestures when I was near.

On the sports field I was often punched when the teachers weren't looking, and sometimes even when they were. To try and help protect myself, I spent hours and hours running and in the gym. My body became and remains is fit and well toned, but I can never seem to build much muscle no matter how hard I try.

Even now my voice is quite high, and I have little hair anywhere other than on my head. I need to shave only twice a week and never have an afternoon shadow.

As far back as my twelfth birthday when I spent a joyful few hours alone in my older sister Pam's bedroom, I have loved dressing as a girl. I don't mean just trying to squeeze into over-tight skirts and knickers, looking obviously like a man in drag. No, I have always taken the process very seriously and for two years now, with Debbie's help, I have been able to go out in public dressed as a girl and be convincing. I even get propositioned sometimes. I really love that, though I never take up the offers.

Debbie and I met at work. After a couple of weeks she suggested we went out to the cinema and it just went from there. We are very fond of each other as I say. After only 9 months we moved into a flat together, and we have lived together for over three years now. For the first six months everything was normal, just like other couples are, but then things gradually began to get a little strained. I remember so well that night when Debbie felt she couldn't hide things any longer and, over dinner in the kitchen, burst out with the earth-shattering news that she was bisexual and had been seeing a girlfriend for the last four weeks. I asked her if she wanted us to split up. She said no, that she loved me and found me attractive, but that she needed to see her girlfriends as well. I think she expected me to end it there and then. I didn't.

Instead tried to calm her down. I put my arm around her and hugged her. I told her I loved her more than this revelation could destroy and that I wanted to stay with her. She cried and eventually told me how she needed to be with another woman sometimes, but that she still loved me. She had found her 'friends' through the lonely hearts adverts in the newspapers but the latest 'friend' had threatened to tell me about their relationship so Debbie had felt she needed to tell me first. I told Debbie I respected her for telling me.

I then told her about my own little idiosyncrasies. How I had to dress as a girl to feel really me, how I had strong feelings towards other men and had had several liaisons in the past. She listened with no look of disgust on her face as I had feared, She did not pass judgement on me. I assured her that I hadn't acted on my feelings since I had been with her, but that they just wouldn't go away. To my amazement and relief, Debbie understood. She gradually became brighter and happier and promised to help me with my needs if I would understand her needs too.

And she was true to her word. I can't tell you what a relief it was not to have to hide my cross dressing from her. I think she found it fun. She was really helpful, giving me tips about ways to dress, putting on make-up, how to walk, how to talk. She introduced me to wigs, to shaving, to flirting, to underwear. She was an angel. Sometimes we would spend entire evenings in our flat as girlfriends, and I learned many of the important mannerisms and behaviour that made me more and more convincing as a girl.

Eventually, after months of training, Debbie thought I was convincing enough to go out with her in public as a girl. We went to the cinema – at least the darkness would keep the pressure off me, we thought. It all went astonishingly well. There was no sign of anyone noticing me, and we both returned to our flat so turned on that we immediately made love passionately while we were still almost fully dressed. I was still wearing my skirt and blouse!

After this success, we progressed to going out as girlfriends once a month. My name became Tina when I 'changed'. Only once did I think I had been discovered - we left the pub quickly and drove away before anything nasty could take place. Several times we were chatted up by boys and, yes, on two occasions I kissed an unsuspecting guy in a dark pub car park before we went home. Obviously I had to make sure things didn't go too far. I was amazed at how much in control the female actually was in such a situation.

I know Debbie went out with her 'other' girlfriends at least as often, That bothered me a little, but we agreed I would not ask her about her girlfriends as long as our own relationship remained strong and it seemed a small price to pay for her whole-hearted involvement in my new identity.

One evening, after this had been going on several months, I could tell that Debbie had something important to talk about. She had been preoccupied for hours and eventually I had to ask her what was wrong. Eventually Debbie told me that her latest 'girlfriend' had been a bit more than the usual one night stand – in fact had been going on for six months - and that Debbie wanted to see much more of her. I went silent, thinking that this would be the end of our relationship, but she went on. This friend, Monica, was married and her husband Barry knew all about her bisexual tendencies. Being bisexual himself, he didn't mind, but felt excluded by Monica's developing relationship with Debbie.

Debbie had, she confessed, told Monica about me and my 'preferences' and Monica had told Barry and Barry had said he really wanted to meet us. It seems Debbie and Monica had cooked up a plan in which the four of us would meet and, if we liked each other, could perhaps spend a night together in a hotel. Debbie would sleep with Monica, and – if we wanted to – Barry and I could sleep together. We would all have lunch together on a Saturday to see if we liked each other and if we did, book everything for two weeks afterwards.

Debbie looked at me in anticipation. "Well, Tim, what do you think?"

I pondered everything. "You shouldn't have told her about me, Debs."

"I know Tim. I'm sorry, but Barry was really keen and Monica tells me he's gorgeous. Please Tim. Say you'll at least meet them."

I thought about it. "OK Debs. I'll meet for lunch. But not as Tina, just as Timothy, OK? And I'm not promising anything. You know I'm not very experienced with guys. Did you tell Monica that?"

She smiled. "Of course. To be honest, I think that's part of your attraction. Shall I call her now?"

"OK. But just for lunch."

Three weeks later we were sitting in the Hark Rock Café with Barry and Monica, having lunch. I must confess I was exited despite myself. Monica had been right - Barry was simply a dream. Tall, tanned and muscular, he came over as sensitive and educated and honestly interested in me. I could feel butterflies in my stomach as he spoke to me, and he spoke to me a lot. After the min course had been cleared away I felt confident enough to tell him about my dressing; how I took it so seriously; how I loved Debbie but needed more, just as she did.

Barry was in his late 20s or early 30s. He told me he had been a professional footballer but was now 'in property' as he put it. As he relaxed more, he told me about his own bisexual desires and how he had found Monica's description of me too interesting to miss. Monica herself was young, small, blonde and very pretty, a stereotypical footballer's wife. I was not surprised that Debbie wanted her so much – indeed I rather fancied her myself. She was bubbly and confident and looked suited to Barry very well.

After a long lunch during which time seemed to fly by, Debbie and I went to the bar to discuss whether to go ahead. There was no real decision to be made. The answer from both of us was emphatically yes. When we returned to the table, it was obvious that Barry and Monica had been having the same conversation and the atmosphere became even more relaxed. It was with reluctance that we had to say our goodbyes and go our separate ways.

Another two weeks later, Debbie and I arrived in a nice, unpretentious central London hotel, chosen to attract as little attention as possible. The hotel was very nice, but anonymous, with a good restaurant and large rooms. Our plan was, this first time, for us to meet in the bar for drinks before dinner and then, if all was going well, after dinner for Debbie and Monica to go up to our room with Barry and I going to theirs. I felt very excited but even more apprehensive. I had never spent a full night with a man before, indeed my experience had been limited to kissing, heavy petting and the occasional oral sex.

Slow trains and a lack of taxis meant that we checked in late and had to go straight up to our room to get dressed for dinner. Debbie was herself excited, but I was relived that she made time to help me prepare.

On her instructions, once in our room I began by taking a long bath in which, with Debbie's help, I shaved myself all over. Using her lady's wet razor and scented shaving foam, I carefully shaved my legs, all my pubic hair and all the fine hairs from between my legs, around my bottom, my stomach and chest. I shaved my armpits and upper arms, finishing with my own razor on what passed for stubble on my face. The sharp blade scraping over my skin was bright and refreshing and I rose from the water feeling smooth and clean and extremely naked. I dried myself with a large white bath towel, and began to smooth creamy moisturiser all over my skin, from my feet to my hairline. It felt cool and soothing, my skin incredibly soft and sensitive. I had washed my hair in the bath, fighting with Debbie for the dryer, and prepared to dress in the way she and I had developed over the last months.

Reaching between my legs, with great care, I placed my fingers on my unneeded testicles and eased them upwards into my body, tucking them deep inside the skin between my legs. They felt uncomfortable for only a second, then I felt them no longer. I folded my soft cock downwards over my now empty scrotum and slipped over it some skin tight, skin coloured panties which held my unthreatening manhood firmly in place. The panties had a low cut front, and had two separate rear straps rather than a single thong, which went neatly into the fold of skin beneath each buttock before joining the waistband above. Once they were in place, it was difficult to see the panties and with pleasure I ran my hands over the smooth unbroken line of my flat stomach and down between my legs. There was no obvious sign of my masculinity. My skin was soft and feminine.

Satisfied, I sat on the toilet seat and carefully applied nail vanish to my toe and finger nails. I walked awkwardly into the bedroom to talk to Debbie while they dried.

"You're looking the best I've seen you." She said. "You must have a special motivation tonight." Debbie smiled knowingly.

"You're looking very sexy too." I replied. "I hope she's worth it."

"She is, Tim, she is."

Ridiculously, I felt a bit jealous then and went back into the bathroom. I put on my deodorant and face creams and sat down again on the toilet. The seat felt cold against my bare buttocks as I expertly rolled on a pair of long back stockings. The smooth material against my skin felt exciting and I stood in front of the mirror to see the effect so far. With more satisfaction, I saw the pale skin of my slender legs and firm bottom set off to good effect by the blackness of the silk. I fastened on a matching black suspender belt and clipped the stocking tops to its straps. I felt even better. Finally I slipped on a black lace G String and pulled it up between the cheeks of my bottom. The strip of material rubbed across my anus and thrilled me. A further check in the mirror told me I was doing well. My flat stomach fell away smoothly to my upper thighs. There as no trace of anything masculine.

A tight black silk padded bra completed the ensemble. I liked the effect even more. Thanks to Kate Moss and the other flat chested supermodels, I reflected, my absence of appreciable breasts would not arouse attention. It might even serve to make me more attractive. The irony was extraordinary.

I walked back into the bedroom, feeling good and knowing I looked good. Debbie was sitting at the dressing table dressed in almost identical underwear, as planned. Her hair was naturally light brown and fell over her shoulders. We inspected each other, each pleased with the other's presentation.

"You're going to be good tonight." Debbie told me.

"Ooh, I hope not." I replied archly.

Together we dressed in matching short black cocktail dresses and medium high black shoes, helping each other with the high zip fastenings. I pulled a long brown wig onto my short hair and secured it there. Its tresses fell over my shoulders just like Debbie's. I brushed it until it shone.

Sitting next to Debbie on the stool, I carefully, as she had taught me, put on very light make up. So many men overdo it, Debbie had said. Using only eye liner and lipstick we both tried to make the most of our features and giggled as we began to look more and more alike. A little perfume and, for each of us, a thin gold necklace and bracelet bought specially for the occasion completed the effect. We stood back, looked at each other, looked in the full length wardrobe mirror and burst out laughing.

We had done it well. We had done better than well. We looked like twins or at least like sisters. And we looked good. Debbie opened a small bottle of champagne and poured two glasses. We toasted each other, my stomach bursting with butterflies, and drank the bubble down quickly. Holding hands, we went out of the room for dinner.

As we entered the bar area, Debbie nudged me and pointed to Barry & Monica sitting at a corner table. Barry looked gorgeous, dressed in a dark blue suit and white open-neck shirt which showed off his tanned skin to perfection. With his jacket off, his strong arms and powerful chest were obvious attractions. I couldn't keep my eyes off him. Seated across the table was his wife Monica, strikingly wrapped in a short red dress that clung to her slim figure. She looked very sexy, I thought despite myself.

Barry ordered drinks for us all and we drank each other's health.

"Here's to a successful evening." He said. "Just me and three beautiful women." He turned to each of us in turn. "Debbie. Monica. Tina." I shivered when he spoke my name like that. We drank and chatted, keeping the conversation light. The waiter brought us our menus and we chose our meals with care. More drinks followed and eventually our meals were ready.

As planned, we had two separate tables. Debbie and Monica sat in a far corner of the large restaurant; Barry and I sat in a booth along the wall. My stomach was even more full of butterflies and I found my appetite had evaporated. I tried hard to eat to balance the drinks I had taken but my head was a little dizzy already.

The food arrived and was very good. My stomach settled a little as we talked. Barry was bright and interesting company, asking all about me, my plans for the future and my dreams. He told me about their house in Portugal and their recent holiday in Florida. As the dessert menus arrived and neither of us felt able to eat more, I felt Barry's hand on my thigh under the table. It sent a shiver down my spine and I froze a little. With some difficulty, he began to tell me how he had been bisexual most of his life but had only recently felt able to do anything about it. As he talked his hand slid up my thigh towards my crotch and I opened my legs a tiny bit for him.

His other hand reached over to touch my fingers as they rested on the tablecloth. He took the tips of my fingers between his and squeezed, looking me directly in the eyes. I lowered my eyes, unused to such attention, but enjoying every second. I shook my hair and smiled at him as the coffees arrived. We drank them too quickly, our mouths getting a little scalded in the process.

We looked over at the girls in the corner table. Their heads were close together and they were talking animatedly. Their knees were touching and they were holding hands. I felt a bit jealous once again and pointedly turned my attention back to Barry as he finished his coffee.

"Are you feeling tired?" he asked.

"Not really." I replied.

"Good! Shall we go upstairs, then?" He said with a broad smile. I paused. This was it, I thought. I nodded and rose slowly, straightening my dress. Seeing me rise, Debbie and Monica also stood up and casually crossed to our table.

"Everything OK Tina?" she asked me with a meaningful look.

"Just fine, Debs." I replied with an equally meaningful wink.

"Shall we share a lift then?"

We all crossed to the bank of elevators. Debbie pushed the call button and we waited impatiently. Eventually one arrived and we crowded in, Barry politely allowing the three ladies to go ahead of him. The doors hummed closed and we began to rise.

At the fifth floor we stopped. Debbie asked Barry to hold the doors and she almost ran along the corridor to our room. She disappeared inside and returned to the lift with my small overnight bag which she pressed into my hands.

She leaned close to me and whispered "Good luck Tina." into my ear, then took Monica by the hand and led her to our room. The lift doors closed just as the two of them disappeared from sight. The lift began to rise again. This time it stopped on the eighth floor. The door opened. My heart was hammering in my chest.

"This is our floor, Tina." Barry said in a hushed voice and took me by the hand. Taking my bag under his arm, he led me to the door of their room and fumbled for the key. His hands trembled slightly as he opened the door and ushered me inside. My stomach was once again in turmoil and my knees felt weak. I tried hard to remember my previous boyfriends and all Debbie had told me.

The lights were low, a bottle of champagne open on the bar top and a huge bed was in the centre of the room. Barry turned the room's radio on and the air was filled with classical music. He locked and chained the door and removed his jacket again. His firm chest muscles were exaggerated by shadows in low light. He poured two fresh glasses of champagne and brought one over to me. I thanked him and the glasses clinked together. I drank too quickly, out of nerves. Help me, Debbie, I thought. What should I do? I looked at Barry. He was a lovely personality in a gorgeous body. A perfect partner for an inexperienced girl. Suddenly I knew what to do.

To my surprise I found the confidence to take the lead and walk boldly if slowly towards him. Without a word he turned square on to me and I raised my arms around his neck, tilting my head back, my hair falling softly over my shoulders. He bent his neck and we kissed. It was a tentative kiss, testing each other out. We both liked what we found, and we kissed longer and harder. Soon our mouths were open and our tongues were entwined, passion at last taking over. I pressed myself against him and his hands found my buttocks. He pulled me more firmly into his body and I felt with weakening knees, his erection within his trousers. It felt so good knowing that I had caused that to happen.