I had been going out with Jo now for a month, and I was beginning to wonder if she really was serious about me – while we’d fooled around quite a bit, kissing and fondling, so far we had not actually gone to bed together. The opportunities never seemed to arise, or if they did, Jo would always make some excuse, or change the subject.
I was beginning to get frustrated, but in all other respects, Jo was perfect for me, so I felt I wouldn’t give up just yet – I really felt something for her that I hadn’t felt in a long time – perhaps it really was love this time. For once I was getting the same vibe from her as well – except for the sex thing. Ah well, having gone without for six months since Susan and I split, I could hang on a bit longer – I just hoped that this wouldn’t end up being a problem, and Jo was just waiting for the “right moment”.
Tonight, I hoped, would be the right moment. Jo was coming over and we were going out for a meal. I’d deliberately left the rest of the evening open, so hopefully she would come back to the flat and we’d finally get it on – that was the plan anyway. I felt a little anxious about the later part of the evening, but whatever happened, the first part would be great anyway. At seven on the dot, as planned, Jo breezed up to the entry phone and buzzed up. “Hi babe!” she squealed when I answered, and at a stroke my doubts were swept aside, replaced by a sudden pleasant feeling of anticipation as I pressed the door button.
Jo was stunning, it has to be said. As I opened the door to let her in, I had to mentally pinch myself that this beautiful girl, just twenty years old, was really going out with me, and this time it really seemed to be working for both of us. Her long strawberry-blond hair cascaded over her shoulders, framing her cute, round, face – large dark brown eyes, full lips and a button nose, perfectly set in a flawless complexion, with a fine dusting of freckles. She wore a little makeup, but only just enough to accentuate her eyes and lips without it being excessive. She smiled broadly and kissed me in greeting, lingering just long enough to let me know this wasn’t the usual hello kiss she used with her friends. I squeezed her gently as we kissed, feeling the womanly curves under her tight T-shirt. Jo was well-proportioned, with a curvaceous figure that was not stick-thin but not overweight either. Her breasts were quite small but filled her clothes well, with a well rounded and firm shape. So far, fondling her breasts had been as far as we had gone, so I knew them intimately. I looked forward to finally getting to know the rest of her delights soon. Jo always dressed stylishly, and today was no exception, the plain white short T-shirt offset with a short black skirt that hugged her smooth thighs, showing the curves of her fine bottom to good effect, and complementing the smooth pale skin of her shapely legs. She wore some classic black slingbacks which were quite high-heeled, which brought her height up to about 5-10.
The first part of the evening went brilliantly. We talked non-stop as we ate at one of the better restaurants in town, and Jo was giving me lots of very positive body language, as always – squeezing my hand and making lots of physical contact, smiling a lot and laughing, even at my poorer jokes. Jo’s perfume was a sophisticated and heady scent that set my pulse racing every time I caught its aroma, and that scent will forever burn in my brain, right back to this moment. I was thoroughly enjoying myself tonight and she was too. After we finished eating, I invited her back and she readily accepted, and we walked arm in arm back to the car. It was at this point I detected a change in Jo. She appeared to become a bit more nervous and a lot quieter as we drove back. At first I thought maybe she was apprehensive about what surely must be the inevitable consequence of the evening, and I was sort of right, as it turned out…
We cuddled on the sofa, sipping from a tall Vodka (sod the coffee…), and we had been at this point a number of times before, kissing, me pulling up her top, moving my hand lower… Jo abruptly broke off, clearly agitated. She looked unhappy. “What is it, babe?” I asked gently, taking her hand.
“I.. I have to tell you something” she said, not making eye contact.
“OK” I said, tensing, sensing her anxiety.
“I want you to know that I really think we have something good here…” she trailed off.
“But.” I completed her unfinished sentence. I hoped this wasn’t what I feared – dreaded – ever since I started to admit to myself my feelings for her.
“It’s not what you think. It’s worse.” she said.
“Darling,” I interrupted, “whatever it is just tell me. I can’t think of anything that would make me feel any less for you…” I stopped, perhaps I’d already said too much.
“This will”. She said, flatly.
“Just tell me. Please.”
“Well…” she sighed, “More than anything in the world I want to go to bed with you right now. I really do. I can’t believe how patient you’ve been with me – you’re very sweet, you deserve a medal for that.”
“So let’s do it babe” I said, smiling and gently squeezing her hand.
“I… can’t” she said. My mind was working overtime, trying to think of all the reasons that she might have – abuse, rape, medical problems, anything that might make a girl unable to have sex. I pulled her towards me, trying to comfort her.
“I undertand babe, whatever it is.. you can tell me”. For the first time, she made eye contact, her eyes filled with tears, though she was not yet crying.
“It’s not what you think” she repeated.
“I don’t know what I think babe, you’ll need to tell me. Whatever it is won’t make any difference – I… I, well, I think I’m falling in love with you – if there’s a problem let’s work through it”. There was a long silence. I hoped I hadn’t blown it by mentioning the ‘l’ word… it surprised me too, but seeing her sitting there in such a state, I felt an overwhelming tenderness and desire to help and protect her – love seemed to be it.
“I feel the same”, she finally said in a small voice. My heart leapt – this was wonderful! I hugged her, but she pushed me away, this time the tears flooded and ran down her face. This was not good.
“Please Jo, what’s the matter?” I pleaded, gently. “I’ve just had the most wonderful month of my life – you are wonderful. I know I don’t really know you yet but what could possibly be so bad that it would make me change my mind about you?”. Jo didn’t answer, but sat motionless for another minute or so.
“This.” she suddenly said, quite forcefully, standing up. She stood in front of me, a few feet away. In one swift movement, she pulled up her skirt with one hand and pulled down her knickers with the other, revealing a perfectly smooth, small cock. It looked a little like a Greek statue – smooth, white, the foreskin rather shrivelled and closed up, resting like a plump sausage on the pouch of her ridged balls, shrunk a little with cold. “There”. she said. “I’m pretty sure that changes your mind, doesn’t it?”. She held her pose for as long as it took to say this, then flopped back down on the sofa, crying her eyes out, curling up into a foetal position, inconsolable. My mind was reeling, I must admit that this possibility had simply not occurred to me – Jo was a transsexual.
The thing was, this revelation did not change my mind. It did not disgust me, or frighten or repel me. Jo was Jo, what she had between her legs didn’t change that. In fact I felt… relief. Obviously that was why Jo had been so reluctant to go to bed with me, or even let my hand wander up her skirt – she was afraid that when I found out I would reject her. Well, there was no question of that – I would just have to adapt. “Oh Jo…” I said, and pulled her into my arms. I kissed her wet cheeks tenderly, stroking her hair, rocking her in my arms. “Jo… it changes nothing. I understand why… I understand. Please darling, look at me”. She did, and I kissed her swollen lips, tenderly at first, but then more ardently as if to prove that I couldn’t care less. And the funny thing was – I couldn’t. Eventually, Jo spoke, croaky-voiced.
“You still want me? You still want… want… me?” she whispered, lost for words.
“Yes darling, it changes nothing about you, how I feel about you. I’m intrigued, and interested, surprised for sure, but it doesn’t make me love you less. How could it – it’s just a cock. Why, I’ve got one much like it myself”. I smiled, and for the first time since we got back to the flat, Jo did too. Her face came alive, shining through her tears. I kissed her again. “We’ll work something out”, I said.
“All my life I knew I should be a girl. I always used to say that’s what I wanted to be when I grew up. My parents gave up trying to make me be a boy when I was about eight. I think they realised it was never going to work. When I was twelve I started to see a therapist, and she confirmed what I already knew – genetically I was mostly female. They gave me hormone treatment from age 13. I always expected to have SRS eventually, but by the time I was about 16 I decided I didn’t want that after all. I’m proud to be who I am now, but… of course, sex has always been a problem – relationships have always been a problem. I could never come clean to the boys I went out with, I would always break it off before it came to that. I never knew how to handle it. With you though, things are… different – I knew I had to really face up to it this time.” I held her tightly in my arms. We’d talked now for hours, finally Jo was accepting that I wasn’t going to reject her now.
“So have you ever…” I asked. “No, I’m a… virgin”. Jo laughed, sheepishly. “I masturbate a lot though. Way too much actually.” She said this with no embarrassment – I felt really close to her.
“Yeah, well, don’t we all” I said. We both laughed. “Darling… maybe it’s too soon, I dunno… but if you wanted to, we could, you know,…” I trailed off.
“I’ll show you mine if you show me yours?” Jo beamed, her face radiating light.
I kissed her deeply and stroked her creamy smooth thighs. The thought of what awaited my fingertips just inches away was making me breathless with anticipation and erotic lust. My own cock was rock hard, straining inside my jeans, and Jo was squeezing it gently through the fabric. For a while, neither dared to go further, enjoying the moment of anticipation, savouring our last few moments of innocence. Jo made the first move, pushing back and pulling at my belt, releasing the clasp, then flipping the top button of my jeans open. She smiled, then slowly unzipped the fly, pushing the jeans down as best she could. My cock was oozing fluid profusely and had made a dark wet mark on my underpants, the pink head visible behind the damp fabric. “Ooh, what have we here?” Jo asked, pulling the pants down and over, allowing my cock to spring forward, throbbing. I had never felt so hard for such a long time. Jo bent and took my member in her tender mouth, sucking gently, stroking with her fingertips. My god it felt good! I almost came in a jerk as I felt her tongue caress the glans, but I managed to hold back. After a few minutes of this wonderful treatment, I could take no more without coming, so I gently pulled her up and kissed her deeply once again, tasting myself on her soft lips.
“So let’s see what this skirt is hiding” I said, “and this time let’s have a proper look”.
Jo giggled. “OK.” she said. I could already see something of a bulge in the front of her skirt, and Jo helped me to unzip the skirt and wriggle out of it, casting it to the floor. She wore lacy black silk knickers, very feminine, but the hard bulge they hid was unmistakeable. As we kissed, I pulled her knickers over and down, hooking them behind her soft smooth balls. Her cock was very hard, and now quite a bit larger than when I had first seen it, the head fully exposed and weeping clear juice. Somehow it looked very feminine – much smaller than my own seven inches, I guessed maybe 4 or 5. The thing that really stood out was the fact that it was utterly devoid of all pubic hair – completely bald, smooth and utterly delightful. A very faint whiff of hot sex caught my nostrils – I recognised the familiar sexy smell of warm cock – just enough to make me almost go crazy with lust. I took her smooth member in my hand, and still kissing her, I started to slowly masturbate her, drawing the foreskin back and forth over her glistening head. Her cock jerked involuntarily and a large globule of clear fluid bulged out, dribbling onto her flat stomach, trailing a thin string of sticky fluid. Jo moaned, whispering my name as we kissed, as I continued to slowly wank her cock.
In turn, Jo took my cock in her hand, and started to follow my movements, until we were jerking each other off, breathing hard and fast. I felt Jo was close to coming, and bent to take her penis in my mouth. It tasted a little bit salty, but far from unpleasant. I could feel the ridges on my tongue, at once a unique new sensation, yet strangely familiar. I continued to jerk her shaft, willing her to spurt into my mouth. I felt her tense, then go rigid, arching her back, moaning loudly. I felt the hot spurting come before I tasted it, and there seemed to be a lot of it. The splashes hit the back of my throat, almost making me choke, but I caught it, and savoured the slippery fluid between my tongue and the roof of my mouth. The taste was not unpleasant – slightly peppery, yet a little bland. I was so focused on these new sensations that I hardly noticed that Jo was almost yelling with pleasure as I slowly continued to wank her cock into my mouth, licking off the last drops – very gently – I knew all too well how it felt to be too rough just after the moment of coming. Jo’s body flopped back, limp. “Phew!” she cried, breathing hard in short raspy bursts. Her hand still gripped my own cock, but in the heat of the moment she’d stopped moving it. Swallowing her come, I was suddenly aware of the strange situation I found myself in with renewed clarity – here was Jo, my own beautiful long blonde Jo, the Jo I had dreamed and fantasised about for the last several weeks, half naked on my sofa, her small delicate hands wrapped firmly around my cock, and she’d just come, hard, right in my mouth! From her own rock-hard, hairless female cock!!! At once the full erotic reality of the scene hit my brain, and my balls responded. In a second, I felt the rising sap, unstoppable, and I just came in a huge, mad rush, right then. My spunk jetted out, white flying across and landing square on Jo’s T-shirt, followed by further spurts that landed shorter, on her exposed stomach, and yes, on her now slowly detumescing cock. I moaned in ecstasy, and the final dribbles oozed out and ran down across Jo’s pretty little fingers.
We kissed, again and again, revelling in the love we’d found. For the first time in her life, Jo was experiencing physical love with another person, and for the first time in mine, I felt it really meant something.
“Darling?” Jo started.
“Yes, lover?”
“Shall we go to bed and really make love?” I hesitated. I wondered what she really meant – I wasn’t sure what she had in mind. I must have looked a bit doubtful, but before I could say anything, she smiled, took my hand and pulled me up off the sofa, dragging me towards the bedroom. “Don’t worry,” she said, “we’ll work something out.” She half winked, echoing my own words. We were in each others arms by the time we pushed open the bedroom door, kissing and laughing. I fumbled for the lightswitch, but Jo checked my arm. “Not yet” she whispered. We kissed passionately in the darkness, a chink of light from the hallway illuminating Jo’s face just enough that I had to gasp at her radiant beauty. Her perfume was still faintly fulminating off her glowing skin, and slowly, we undressed. She pressed her warm full body against mine, and I savoured the feeling of the two of us sharing that space so intimately. I was aware of the extra piece of flesh that pressed warmly against my groin – how could I not – and I started to feel myself get hard again. The effect was mutual – as I grew harder so did she. We both realised and giggled a little, but resumed the intimate caress, kissing and kissing. I fondled her pert breasts, which were both soft and firm, young, vital. Her nipples became erect at my touch, and I bent to suckle them gently. Jo moaned softly as I did so, arching her back and pushing her pelvis towards me, her hard rod jutting out, catching the light.
Pulling me towards the bed, Jo was fumbling around for something in her bag which she’d dropped on the floor. She pulled me onto the bed, and we rolled around for a few minutes, giggling in the darkness. It was strange to feel her body next to mine – so familiar, the soft feminine curves, yet pleasantly strange. Every time her cock pushed into my thigh, or against my own cock, it was a surprise, renewing with each glancing touch the erotic strangeness of the night. I felt her hands on my cock at last – they felt oddly wet, and after a second I realised she was rubbing some sort of oil or cream into it. There was a very mild burning sensation to the cream, which made me all the harder, and I heard some further squelching that I couldn’t quite place, then Jo threw her bag back on the floor and resumed our lovemaking. “Come on darling, it’s time” she whispered, and pulled me on top of her. Instinctively, I went through the motions of easing my weight down, feeling her thighs parting, her legs lifting and widening, as I had felt with other girls many times before. This time I felt a little puzzled, but needn’t have worried. Jo’s hand guided my cock smoothly below her hairless tight balls, and I felt her cock push against my pubic bone and felt the heat on my cock as I entered her. In the dark, it felt like any woman’s well-wetted vagina, tight yet yielding, hot, slippery yet gripping just the right amount. I pushed very slowly, afraid to hurt her, but her hand guided me in more forcibly, yet she never made a sound. I felt her smile as her lips brushed mine, my lips on her teeth. “Welcome home lover” she whispered, and after a further minute savouring the sensation “…now fuck me good, hear?”
I started to move my hips rhythmically, I needed no further encouragement. I could feel Jo’s hard cock pressed into my belly, and her hand slip down and begin to masturbate, as I slowly and fully fucked her beautiful arse. I can truly say it was the best lovemaking I ever had – and it was love, no doubt about it. We simply fucked like that, face to face, kissing, caressing, until finally I could hold on no longer and had to come. Jo sensed the time was right, and we began to slowly reach a simultaneous climax, until at the final moment, all motion stopped and I felt myself pumping hard into her bottom as a hot sticky sensation flooded between our two bellies. We both sighed and relaxed as the waves of orgasm passed, resting in that position, still kissing, our lips becoming sore. “Oh darling” Jo whispered, her voice a little hoarse, “that was just so… wonderful. I’m…” I think she was starting to cry, “…not a virgin anymore. Thank you lover, thankyou!” she cried. I said nothing, a little overwhelmed myself. If I’d said a word, we’d have both been in tears. I simply gazed at her with love, my eyes accustomed to the dark now, revealing her golden glow in the dim light. Her hair was cascading around her face, somewhat mussed up but very alluring, her firm tits heaving as her breathing gradually quieted.
“I love you Jo” I finally said, feeling my cock slip out at that moment.
“I love you too.” she said, smiling. We cuddled, and slept.
As morning broke through, flooding the room with sunny light, I woke first and smiled as I felt Jo’s warm body beside me and the events of the night before. I gazed at her sleeping features – her hair a pinky-yellow in the early light, spilling over the pillow chaotically, her lovely lips seemed to be almost smiling, puffy with sleep. Her closed eyes showed her naturally long lashes, flicking slightly with her dreams, some traces of eye makeup remained, the rest washed away by her tears of the previous evening. My eyes traced the smooth contours of her throat and shoulders, perfectly formed. I was still having a little trouble reconciling the knowledge that Jo was born male with the vision of feminine loveliness in front of me. There was not even a trace of a tell-tale Adam’s Apple, as her honey-smooth tinkling voice would have told me anyway. My thoughts wandered – did this mean I was perhaps gay? The thought didn’t bother me, but didn’t strike me as right either, yet the revelation of Jo’s secret had excited me, I recalled. Oh well, whatever. Jo stirred, breaking my train of thought, and turned over, flicking her hair back as she turned, still asleep. I spooned up behind her, my arm resting across her breasts, my cock hard, pressed between the soft round globes of her buttocks. Jo murmured, bit didn’t rouse.
My hand strayed lower, and I felt her cock, erect with her dreaming, and though I knew what to expect, it still felt excitingly different, sending a little shock of pleasure through me. I stroked it gently, feeling its smoothness. There was no sense of stubbliness around the base, I wondered how she got it so smooth – I’d ask her later. Her balls felt warm and slack, and moved gently of their own accord as I caressed them. I fell back asleep for a while, waking again as I felt Jo stirring, pushing back against me and murmuring pleasure. My hand was still holding her penis loosely, still hard. “Mmmm, that’s nice sweetheart” she said sleepily, rocking back and forth against me. After a few minutes she woke fully, and swung herself into a sitting position on the edge of the bed. “Where are you going?” I asked. “Just need to go to the loo, be right back”. I watched her as she walked out of the door, admiring her firm apple-shaped bottom and lovely legs. She didn’t even have narrow hips, I reflected – just the perfect womanly figure, and not too skinny. I could hear Jo peeing, loud and long. She hadn’t bothered to close the door and the sound travelled. I couldn’t see from where I lay, but I was curious whether she stood or sat… She came back into the room, and I watched her cock, now limp, swinging with each step, her balls firmly pouched up – it was cold in the flat. Smiling at me, she climbed back into bed, cuddling up. We kissed.
Over breakfast, Jo filled me in on everything I never knew about transgender issues, saying that she had been dying to discuss them with me these past few weeks. A few remarks that had made little sense at the time suddenly fell into place too – I think she had been trying to drop the occasional hint, unsuccesfully. She paused. “You know, it’s so great to finally be on the level with you. I feel so.. relieved, and it opens up so many possibilities now. You are wonderful. Thanks for… not rejecting me”.
“Was that really your first time? You seemed so… assured somehow.”
“Yes it was my first time. I have lots of fun toys though” she smiled. “I’ve never been into any sort of ‘scene’. I know there are clubs and bars for people like me, but they never appealed somehow. I often thought about going there just to find… anybody, but never did pluck up the courage. I always wanted to be normal, if that doesn’t sound bizarre.” I felt I understood – Jo was really the most lovely, natural, intelligent and witty girl I’d ever met – somehow the idea of her picking up strangers in a bar didn’t fit with my picture of her. “Funny thing is, I love sex. Or at least, I love to masturbate and play and fantasise. When I met you I so wanted to do it with you, I thought I would finally have to face the truth. I tried… but anyway…”
“Darling, it’s OK – there’s no way I’d let you go now, you’re so… special. I love you, and who you are. We’ll have all the fun and sex you want, starting right now!”