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First Night Nerves

Nervous Tim becomes Tina and loses her virginity
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 three 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 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 once a week and never have an afternoon shadow.

As far back as my mid-teens, 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 and immediately got on well together. After a couple of weeks she suggested we went out to the cinema and it just went from there. We grew very fond of each other very quickly and after only nine months we moved into a flat together. 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 I 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 then took a deep breath and nervously 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 too. 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. Often 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 a girl actually could be in such a situation.

I knew 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 for nearly a year, 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 she told me that her current 'girlfriend' had been a bit more than the usual one night stand – in fact had been going on for three 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. "Okay, Debs. I'll meet for lunch. But not as Tina, just as Timothy, okay? 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?"

"Okay. 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 main 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.


Two weeks later, Debbie and I arrived in a nice, unpretentious central London hotel, chosen to attract as little attention as possible. The building was very pleasant, but anonymous, with a good restaurant and large rooms. Our plan, this first time, was for us all 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 while Barry and I would go 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, smiling knowingly. "You must have a special motivation tonight."

"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 was no bulge – 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 bubbles 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 absolutely 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 dinner was 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 okay, 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 the 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.

We kissed longer and longer, our mouths sliding over each other as he kneaded my buttocks. I felt his hand rise and the long zipper on the back of my dress being lowered. His hands slipped inside my dress and his fingers played up and down my spine, then downwards to toy with the back of my g string. His erection was even more obvious to me now. I lowered my arms from his neck and my dress slid easily off my shoulders to fall to the floor around my ankles. My bare skin pressed against his clothes and I could feel the animal heat of his body against mine.

Barry stood back to look at me. He shook his head. "God, Tina, you're lovely!" he gasped. I felt a warm glow inside. His fingertips stroked the skin of my shoulders and across my flat stomach. I raised my hands to his waist and deftly unfasten his belt, then unbutton his waistband. His zipper followed quickly and I lowered his trousers to the floor. A huge erection battled to escape from his pants. I eased them over his growing cock and lowered them to the floor. He kicked his shoes away and stepped out of his clothes.

Rising to my feet, I unbuttoned his shirt and slipped it over his shoulders. It fell away, leaving his wonderful body naked in front of me, his erection demanding my immediate attention. My hands lightly touched his firm chest, then the clearly defined muscles of his stomach – evidence of a six-pack very much present - as I sank to my knees and took his erection in one hand, cupping his testicles in the other. I began to pump my hand steadily up and down, feeling its strength and vitality, before opening my mouth and taking it in. Remembering my experiences in school and Debbie's technique, my tongue lapped over its smooth head and its tip sought out the ridge beneath. I took it further into my mouth and dragged my teeth along its sides. Barry moaned and ran his fingers through my hair. I licked along his ridge, down to his tight sack and back up to the head.

Bending my head and neck down lower, I took each testicle into my mouth in turn, working the shaft with my hand, before sliding a finger in between his buttocks to stroke the rim of his anus. I felt Barry tremble as I worked, and his cock, now back in my mouth, began to pulse. I moved my mouth smoothly up and down his shaft as he swayed back and forth, moaning quietly.

Eventually he must have felt too close to cumming because he suddenly lifted my head away. Taking my two little hands in his big one, he led me to the large bed where he turned me around and sat me on the edge. My stocking-clad feet barely touched the floor. Barry kissed me on the lips and pushed me onto my back.

With consummate skill, he lifted my legs and my g string was whipped away from me, leaving me exposed to his gaze and touch, my pale delicate core framed by the dark silk of my stockings and suspender belt. He bent over and kissed my navel, then his rough tongue licked my lower stomach and my skin coloured panties before his head dipped down and I felt his warm wet tongue between my buttocks. It felt incredibly exciting, but I began to feel anxious inside. I had never been this far with a man before. The tip of Barry's tongue suddenly slid into my anus. Again it felt wonderful but I was more afraid. I wriggled on the bed as Barry forced open my legs and his powerful body rose up over me. I began to tremble.

Barry must have seen the fear in my eyes because he suddenly stopped.

"Is everything alright?" he asked insistently. Then realisation dawned. "Have you ever done this before?"

I shook my head, embarrassed.


Another shake of my head.

"Do you want to?"

My turn to pause. A quick nod and a smile.

"Are you really sure?"

Another nod. Barry suddenly smiled and his body lost its tension.

"Well, my love, we will have to take it very slowly. We'll try it another, easier way." His mouth touched my ear as he whispered, "Roll over. Get on all fours."

I did as he said. I felt vulnerable but excited. Barry's soft, warm voice was reassuring as he said:

"Now rest your head on the pillow for a bit." I realised that, in doing this, I was leaving my bottom sticking up in the air before him, my cheeks parted and my anus fully accessible to him. My stomach churned but I did as he asked.

"Relax, Tina. Trust me," Barry whispered. I closed my eyes and tried to breathe more steadily.

I felt a strange wet feeling between my buttocks and realised Barry had poured some lubrication onto my anus. His warm, rough palm began to massage it into my skin and I felt warm. Then suddenly the tip of one finger just broke slightly into the tight grip of my sphincter. I felt my body react, trying to push him out, but he tried gently again and again until what at first felt like the size of a cucumber, but which was in fact only the tip of one finger up to the first knuckle joint, was inside me. He turned his finger around, working the lubrication into my passage. I tried to relax but my stomach was tight and there was a lump in my throat.

His finger still within me, more lubrication was poured onto my cleft and I felt a sudden shock as Barry worked his finger deeper into my bottom. He talked softly as he did so, his voice comforting and reassuring.

"Just going a little deeper now. Just a little deeper. There! One finger all the way in. You are a real virgin, Tina, aren't you?"

I felt at once exposed and vulnerable, but incredibly aroused at the same time. Barry turned his finger around inside me once again. It felt wet and huge and I felt an urge to push against it. I pressed backwards.

"God, Tina, you are keen." Barry laughed. "Now the next part is harder. I need to get another finger in alongside. Tell me if it hurts too much." I braced myself both mentally and physically for an invasion. I felt more lubrication on my buttocks and Barry's warm hand stroking my lower back and buttocks as he talked soothingly.

"Now, my little virgin, I'm just going to slide my finger in….now." I felt hard pressure on my anus, prying it open followed by a 'pop' feeling as something large was thrust into me. I felt my body involuntarily trying to push the invader out, but Barry held on firmly inside me until the spasm passed.

"That was a difficult bit. Now I'm just going to get you a bit more used to me." So saying, he twisted both fingers around within me, and moved them in and out a bit. My anus was sore already and the roughness of his knuckles as they passed in and out was making me sorer still.

"Now for a little stretch." And I felt cold air rushing into my insides as Barry forced his fingers apart, stretching my anus as wide as he could, fighting against my sphincter. I tried to relax myself, breathing as slowly as I could while my rectum was violated. Sensing my attempts, Barry stroked my buttocks further and kissed me on the small of my back. "Nearly there. Nearly there."

My guts felt as if I had swallowed a football, so new was the sensation, but there was a further shock to come as, without warning, Barry thrust two fingers from his left hand alongside those from his right. I cried out in shock and pain, and bit hard into the pillow.

"I'm sorry, darling. If I'd warned you, you would have tensed up and it would have hurt even more. The worst bit's over now." I whimpered in response, and Barry spoke further, whether trying to comfort me or to turn himself on, I couldn't tell.

"I wish you could see this, Tina. Four fingers in your anus, pulling you open. Making you ready. You're getting so loose, so open. Soon I'll be inside you properly."

And indeed I could feel myself yielding a little. The pain had reduced considerably and although I still felt the need to pee and push his fingers out, the urge was less now. He stretched me cruelly, holding me open with his hands. I felt as if he was tearing me apart. As he stretched me he whispered under his breath "Incredible. Incredible." I felt my body opening.

"It's time, babe. It's time," he at last mumbled in my ear.

I felt his fingers suddenly withdrawn and cold air rushing into me. Barry gasped, then I felt something very large and firm and slippery pressing against my wounded anus. I felt a sudden pressure and with a 'pop' it entered me, stretching me tight. A hard ball of heat began to form in my chest and I couldn't breathe. Barely pausing for breath, Barry pressed further into me and with a terrible burning feeling, I felt my guts being pried apart by a huge invading monster. I began to pant, my breath cut off by the beast in my throat.

"Nearly half way," said Barry and I felt faint. Surely there couldn't be more. "I'll try and move to loosen you."

As he said that, I felt the monster withdraw from me a little, then come flooding back in with force. I gasped and held the pillow tight against my face to muffle the sound. Again and again Barry moved with difficulty in and out of my tight, dry passage until my hips felt like jelly and I was sure I had peed myself. Barry was starting to grunt with the effort and his thrusts were getting stronger and stronger. I tried to concentrate on loosening up, on relaxing, on enjoying the feeling which was so alien. I was feeling tighter and tighter, the burning getting stronger with every thrust. I thought I would be sick on my pillow.

Then suddenly, incredibly, I felt my body yield. It was as if a tight elastic band had been undone inside me: one moment my body was trying valiantly to expel the invader, the friction burning my insides, the next moment my whole being seemed to open up and welcome him. I felt my sphincter give up the struggle and burst open wide to receive him. Barry must have felt it too as with a powerful thrust he sank deeply into me, burying his whole length in my now welcoming passage.

"Baby! You did it," he said, and his thrusts began in earnest. Sounds of two wet bodies colliding began to fill the room, mixed with Barry's increasingly loud grunts and my own stifled moans. The terrible burning became a wonderful strong warm wet feeling within me and my legs began to tremble beneath his onslaught. My breath came in short pants and within my panties I felt a leaking from my own surprisingly soft cock. Tears of pleasure began to form in my eyes and I buried my face deeper into the pillow. Above the passion I clearly remembered being called 'pillow biter' at school. God if they could see me now!

Barry's passion was driving him hard now, his climax rapidly approaching. He grasped my hips with both hands and his thrusts became even more violent, his balls slapping against me as he hammered into my body.

"Oh, baby! Oh, Tina… I'm going to cum." He gasped.

"Yes. Mmmm Yes!" was all I could mumble in reply. Within seconds I felt the powerful tension in Barry's body break as his hot seed cascaded out of his cock and into me. His body, racked with the spasms of his orgasm, twitched and trembled as his semen poured into my ass. His spasms slowed and with a sigh he collapsed across my back, pressing me face first into the bed, his cock still firmly within me. We lay in silence, motionless for a while, catching our breath.

"That was fantastic," he finally breathed into my ear. "Just the best." I felt really good inside as he softened within me. At last he put his hands on the bed, either side of my head, and raised himself up, gently pulling his flaccid cock out of my rectum.

He rolled alongside me. I rested my head on his shoulder, my long hair across his chest and he put his strong arm around me. I was trembling with excitement and the incredible feelings he had produced within me. Exhausted, we dozed for half an hour before the cooling air in the room roused us. Barry kissed me on top of my head.

"Bed time, darling," he said. I carefully stood up and walked unsteadily, my knees still weak, across the room to the bathroom. I closed the door and, leaning on the sink, looked apprehensively in the mirror. My hair was ruffled, my lipstick smudged, my eye makeup runny. There were red handprints on my hips and fingernail marks on my back. My buttocks were beginning to show bruises.

I felt deliriously happy.

Blessedly, my stockings were undamaged and I unfastened my suspender belt and rolled them down and off. The bra followed quickly. My skin coloured panties were still tightly in place. I carefully pulled them aside to allow my cock to hang down and I sat on the toilet to pee. As my buttocks parted, the cool air hurt my sore rectum. I reached down to touch myself and found my anus still gaping open. When I looked at my fingers I saw blood along with the white sticky fluid that dripped from me.

Semen, I thought. My lover's semen.

I carefully removed my wig and locked the door then turned on the shower and stepped inside. The warm water felt wonderful and I washed myself all over with lots of shower gel, feeling my aches and bruises melt away. The soapy suds made my newly ravaged anus sting, but I didn't care.

At last I turned off the water and dried myself on a large fluffy white towel. I pulled on one of the bathrobes hanging on the back of the door, carefully secured my wig back on my head, and stepped back into the bedroom.

The room was in darkness. Light from the bathroom shone directly across the bed and I saw Barry asleep neatly on one side under the bedclothes. The sheets on the other side were turned down to welcome me. I turned off the light, tiptoed across the room, dropped my robe and slipped naked into bed beside Barry where I snuggled close to his warm powerful body. I fell asleep.


I opened my eyes to the sound of the room's kettle boiling. Barry stood near the window, a white towel wrapped around his waist, making tea. He turned towards me.

"Good morning – Tina?" he asked, his intonation asking me to confirm I was still a girl. I nodded, feeling disoriented, unsure how to greet my new lover. "Tea?" he asked. I nodded again.

"Mmm, please."

"How do you feel this morning?" he asked, his voice showing he really wanting to know.

"Sore, I'm afraid. And a little battered."

"I'm sorry. Perhaps I got carried away."

"No!" I insisted. "You were perfect. I couldn't have asked for more."

"And you don't regret it?"

"Not one minute, Barry. I loved it all."

Barry carried the two cups of tea to the bed and sat down. I sat up next to him. We sipped the hot liquid in silence. It tasted horrible and we both burst out laughing. My giggles made me wriggle on the bed and a burst of pain from my bottom shot through me. I winced.

"Will it always be so painful?" I asked, unconsciously assuming there would be other occasions to find out.

"No, darling. You're not a virgin any longer. As long as you don't go too long without .. someone … your body will get used to it. Eventually it won't hurt at all – it will all be pleasure."

"I'm really glad my first time was with you," I said, running my fingers down his muscular arms. "You were so gentle for such a strong man."

"I couldn't have been anything else with you." He kissed me lightly on the lips, then kissed me again more passionately. Our mouths opened, our tongues touched and we melted together again. Barry pushed me back on the bed and lay alongside me, his face over mine, kissing me deeply. My arms went around his back and my legs rose.

His towel fell away from his body and his cock rose strong and proud before my eyes. I felt overwhelmed with desire, my newly experienced body aching for him again. I kissed him with real passion as he deftly manoeuvred himself between my legs. He knelt between my thighs and looked down on me. I smiled, my long hair fanned out over the pillow, naked beneath him.

Reaching over my shoulder, Barry took the tube of lubrication from the bedside table and spread some on his fingers. Looking me straight in the eyes, he began to rub it over his erection. I arched my back a little, desire filling my eyes. He placed a hand under each of my knees and lifted them up and apart. My legs bent and opened wide, exposing my panty-covered genitals and my reddened rectum. Barry spread more lubrication on his hand and began to massage it into my soreness. The coldness of the jelly made me gasp, but compared with the burning it felt wonderful. Barry's fingers slipped easily into my anus, still weakened by the previous night's lovemaking.

"Now let's do it properly," he said hoarsely, and lowering his body between my knees, placed the tip of his cock against my aching entrance. He pressed himself into me.

My body opened immediately to welcome him. Joy must have shown clearly on my face as he slid smoothly his full length into my warm, moist channel because his face, merely inches from mine lit up with delight. My legs rose and wrapped themselves around his slim waist, leaving him free to plumb the deepest recesses of my body. I felt him drive powerfully into me until his wiry pubic hair grated against my sore buttocks. I traced patterns on his strong chest with my fingernails and felt moisture running down my cheeks. He rested in me, giving my body time to adjust. I felt his invasion in my belly, in my chest, in my throat. I stroked his face as he smiled at me and held him tighter with my legs.

He began to pump in and out of me in long, smooth thrusts. I looked into the face of my lover as his muscled body drove his cock into and out of my abandoned anus and rectum. Over and over, his measured strokes brought delight to my insides as again and again his large cock penetrated me, the pressure against my prostate bringing pleasure beyond description. Ripples of warmth emanating from my insides flowed through my whole body.

His strokes gradually became faster and harder and my own pleasure became stronger and sharper until with a groan, his face screwed up tightly and with one, two, three fierce thrusts that banged my head hard against the bed head, I felt once again his warm, sticky release within me. His body went stiff as the last few drops of semen were pumped out of him, then he gently lowered himself on top of me.

His weight pressed down on my body and I loved it. My arms encircled him and I hugged him close, feeling his muscular chest pressed against my own, his firm biceps either side of my face. His eyes were soft and dewy as he recovered his breath, and never left mine. My legs wrapped themselves tightly around his motionless body as if afraid to release him. I felt his erection, deeply embedded within me, retreating slowly as he softened inside me. Sweat from his forehead dropped onto my face, salty and fresh. I smelt his masculine body, felt his powerful frame and wondered at the intensity of this new joy in my life.


A while later, showered, make up removed and dressed once again as a boy in my tight jeans and a white T shirt, I followed Barry's masculine frame into the dining room for breakfast. The girls were seated in the window at a table for four and we crossed to join them. Debbie looked up at me questioningly and raised her eyebrows. I smiled and nodded, noticing the flushed look on her cheeks. We had agreed not to ask each other any questions about our night time activities, but we each had the other's mobile number programmed into our phone in case of emergency or extreme unhappiness. Neither of us had needed it.

I sat down gingerly opposite Monica and ordered coffee. Barry preferred tea. The room was light and busy, the breakfast buffet against the back wall. After a few rather stilted 'Good mornings', Barry stood and crossed to the food table, followed by Monica. Debbie leaned across the table to me.

"How was it?"

"We agreed not to ask!"

"Go on – you look half stoned, and you're walking funny!"

"What?" I almost shouted, horrified. Debbie was giggling. "Well … it was great. Really great! Thank you so much for … for … well, for everything." I kissed her lips across the table. "But I am sore." I blushed. "How did you get on?"

Debbie looked dreamy eyed herself. "Monica is a lovely person," she said enigmatically.

"That's about as good as it gets with you." I laughed and kissed her once again.

"Watch that, I'll get jealous," interjected Barry, returning with a large plate of bacon and eggs. As he sat down, Debbie and I rose to get our breakfast. As we reached the buffet table she asked me.

"Well, would you like to do it again?"

"Oh yes. Yes please. But I'm not sure Barry was expecting a … well, a virgin."

"Barry has already told Monica that he thought you were wonderful. They want to see us again – perhaps before Christmas. Would you like that?"

I thought for a minute. "As long as we're still a couple. It mustn't damage our relationship."

"It won't, Tim. I love you. You know that."

"I love you too."

It took nearly a full week for my body to return to nearly normal – but having lost my virginity, it could never be quite the same again. Each trip to the toilet reminded me of the wonderful way in which Barry took my cherry, as I now think of that night.

On the Monday afternoon at work, a bouquet of flowers arrived for me, addressed to Timothy. They were beautiful. I opened the card at my desk, the others very curious. It read:

Dearest Tina, I loved our time together on Saturday. I hope you enjoyed it too. I would love to see you again, with or without the girls. Call me. With love Barry.

I slipped it into my pocket unobserved.

We now meet Barry and Monica several times a year, in new and exciting hotels all over Europe. They have a baby now and are very much in love, but we all still really appreciate the freedom to explore the other side of our sexuality. We trust each other completely.

I could never have an affair with another woman, I believe that would be wrong, but my relationship with Barry is different and, most importantly, acceptable to Debbie who I still love madly.

Debbie and I still go out as girlfriends and will always do so as long as I can still pass for a real girl. I know in a few years that will become difficult – so I'm making the most of life now.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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