tagTranssexuals & CrossdressersBest of Both Worlds Ch. 02

Best of Both Worlds Ch. 02


The first chapter of Best of Both Worlds told how I got to know my shy blonde classmate Robyn, and discovered to my delight that she had a fully functional little cock, and described how we spent our first night together. So, maybe read that first.

I thought this would be a single-episode story, and much appreciate the reader who said s/he got off on it so much that s/he was looking forward to the sequel; and that got me thinking...


Robyn and I immediately began to spend as much time as we could together, both of us amazed to find a lover who fulfilled our most private erotic imaginings and fantasies. I'd like to tell you how our sex life together developed.

When we were together in the evening, Robyn liked to wear a loose skirt, and began to tease me as we talked by raising a knee and giving me a glimpse of her panties. The panties she always wore were plain and straightforward and quite tight, either simple white briefs or boy shorts, but in both cases panties that could hold her little cock in, and avoid any tell-tale bulge when she was wearing jeans. In the evenings she generally wore the simple white briefs, and soon realised how immediately I responded to these quick flashes; she would smile, and then give me a slightly longer look, before tucking her knees demurely down again beneath her skirt. But of course she was inviting me to look at her and respond to her, and she began to leave one knee raised as she talked, with her hands casually wrapped round it, but showing me the whole swathe of white cotton that covered her cock.

The first time she stayed sitting like this, we just went on talking; she was clearly amused that she could see how distracting her panty-play was, before we went off to bed and fucked each other silly. But the next evening I moved beside her on the sofa when she flashed her panties, and began to stroke her thighs, before reaching further to that band of cotton, gently feeling round the shape of her little cock and balls through the material, and thrilled to feel her tense and stiffen between my fingers. Soon her cock was hard and upright in her panties, and I went on tickling and softly stroking it through the white cotton, teasing her by touching her so gently, but also beginning to set up a steady rhythm with my hand as she pressed against me. And soon I felt that familiar tell-tale extra stiffening as she pressed her rigid little shaft against my hand, and she gasped as she spurted into her panties, with a delicious wet stain spreading out across the white cotton. I leaned forward and kissed the tip through the fabric as she finished coming, and sucked some of the sweet cum out of the cotton, before pulling the panties aside and gently licking the final drops from around her tip and her soft foreskin.

A few days later, we were sitting as usual after supper, and Robyn was smiling at me in a way that suggested that she had another surprise for me; and when she raised her knee I saw what it was. Instead of her usual demure panties, she was wearing a pair of loose, lacy French knickers -- the sort of knickers she could never wear in daytime because they would not hold her penis in place. The material was partly see-through, and I could clearly see the outline of her cock, and one of her little hairless balls was just showing, pressed sideways by the lacy edges of the knickers. Just showing herself to me like this was clearly exciting her, as her cock was pressing out against the material before I began to touch her. My first instinct was to plunge my face down on the lace and suck her through it, but I held back, but decided to do it all with my mouth and tongue. So, I pulled her thighs wide apart and knelt down between her knees, very softly kissing and licking the inside of her thighs as I watched her cock stiffen in the lacy panties. Soon I was licking around the little testicles, and teased her this way for a bit before I tucked her cock round the frilly edge of the panties and took the very tip between my lips, sucking up on it to pull her foreskin up and over it, before pushing the soft skin back off the tip with my tongue. And soon, without any extra pressure, I felt that magic extra hardening, and she was spurting into my mouth as I sucked on her tip.

When we slept together, we generally went off to sleep with me spooning her, her back to me and her soft round arse tucked into my groin, with my soggy, soft cock nestling between her bum cheeks, just touching the tight, moist hole it had recently been fucking. And often I woke up in this position, too, and reached around her to touch her big, puffy nipples before my hand found its way down to her groin and softly cupped her delicious little package of cock and balls. Of course this made my cock stiffen, and I quickly reached for some lubricant as my erection nudged her cheeks open, before reaching round again and beginning to stroke her shaft. Robyn would stir, and wriggle against my hard cock, and her own little shaft grew between my finger tips and the foreskin peeled off the tip. I think this sensation of her cock swelling and hardening between my fingers when she was half asleep was one of the most delicious things about our entire sexual relationship -- that sense that I could make her come to life like that. And then I would slip the tip of my cock into her anus, and feel my own foreskin pushed hard back by her tight sphincter, before I pushed past the barrier and began to move more freely inside her, while my hand toyed with her hard cock till we both came.

When we were making love at other times of day, we usually fucked each other face to face. Robyn still liked sometimes to take the 'male' role and fuck my butt with her cock as she had done for the first time on that first evening we spent together. More often the active penetrator was on top, in our version of the missionary position, with the recipient lying with knees up to chest, to allow easy access to our bum-cunts. But sometimes we reversed it, and I particularly loved the occasions when she lay on her back, and I impaled myself on her cock and rode her till she came inside me, while she masturbated my hard shaft and made me spurt out across her belly.

One weekend morning we had gone back to bed with breakfast and newspapers, and I turned over with my back to her and began to doze. I don't know how long I slept, but I was brought back to wakefulness by the feeling of a very hard, urgent little cock slipping between my cheeks, and, still half asleep, I pressed back against her and felt her slip inside me as her hands felt round me, first for my hard, sensitive little nipples and then for my now-erect shaft, which quickly exploded in her hand as she slid her cock in and out past my sphincter and nudged my prostate.

And often we explored each other in a sixty-nine position. This might be a prelude to fucking, but at other times we just went on playing with each other, fascinated by the look of each other's genitals and the feel of the soft skin as we pulled it up and down each other's shaft, and by the way our foreskins rolled on and off our tips. There was something specially intimate about this time we spent with our heads tucked into each other's crotch, looking and toying and chatting, before the rhythm changed and we began to move towards cumming, usually in each other's mouths. We ended these sessions with deep French kissing that mingled our sperm. That came to have a special significance for us, as we realised how the mingling of our sperm in our mouths expressed the completeness of our physical union.

The bathroom was one of our play-places too. Robyn had discovered my fascination with peeing on our first evening together and she liked to let me watch her pee. Usually she peed sitting down with her knees together, but when I was watching she would open her knees when the flow was established, and I would kneel down and watch the jet, licking the remnants off her tip when she had finished. Sometimes, too, especially when she needed to pee while we were making love, she would pee standing up, 'like a boy,' as she said, and I would take the final spurts in my mouth. One time, we were showering together when she said she needed to pee, and I said, 'Go ahead, here,' and knelt down in front of her, feeling the jet across my chest and running down my belly onto my cock, and then leaned forward, only a couple of inches from her streaming tip, to take it full in my mouth. I couldn't swallow it all, and it flowed down my chin, but I drank what I could, delighted by the intense salty flavour and by the fact that I was taking another liquid from deep inside her deep inside me. This became a regular pattern when we needed to pee while we were making love. She didn't want to drink my pee, but loved it when I peed on her cock -- the hot jet quickly made it stand up to attention, and sometimes I sucked her off then and there, taking the remnants of my own pee in my mouth before it was joined by the spurts of her cum.

When we went out together in the daytime, she dressed simply and demurely as she had before, generally in jeans and a teeshirt or over-shirt, and always with a bra hiding her little pointed breasts. But she liked to dance, and, now that she had a companion who could keep her away from potentially awkward encounters, we often went to nightclubs, where she felt able to express herself far more freely as we danced, and for these evenings she generally wore a loose skirt, often without a bra. We most enjoyed the slow numbers where we could move face to face, me hardening in my pants against her, and feeling a reciprocal hardening in her tight panties, as her constrained little cock responded to mine. On the way home after one of these evenings, I was so excited after feeling her rubbing against me that she went down on me and sucked me to a climax in the club car park before we went home; I wanted to do the same to her, but she stopped me in case we got caught and her secret was unmasked. As soon as we were inside our front door, though, I gently pushed her to the floor and lifted her skirt, and tucked her little cock round the edge of her panties and sucked her to a climax.

These evenings clubbing became a regular habit, but one night she had another surprise in store for me. As we went in to the slow number, I felt her rubbing against me through her skirt, and realised that her cock was hardening without any constraint; she wasn't wearing any panties, and her little shaft, now rigid and upright, was bare beneath the fabric of her skirt. She knew that the lights were low and nobody would notice the odd contour of her skirt as we went to sit down after the dance, and she knew, too, how this would turn me on -- not only the feel of her, but also the knowledge that she was naked beneath her skirt. As we sat in a dark corner, she allowed me to slip my hand under her skirt and to stroke her shaft for a moment, but not to go any further at that point. I touched her again in the car park, but it was not until we got home that she would let me do more, and then she insisted that the feeling of power and exposure this had given her made her need to fuck me first -- she made me bend forward across the back of our sofa and took me urgently from behind, thrusting into my butt for only a few strokes before I felt the spurts of her cum jetting up inside me. Then she said, 'take me like that, too,' and my climax took no longer that hers, as I thrust into her, with her skirt thrown up off her bare butt, and her little hairless balls dangling below.

We also liked to go out into the local park at weekends with a picnic, and to sit on a big rug spread on the ground. Again, Robyn would wear one of her loose skirts, and would give me glimpses of her white panties as we sat there eating. We would then make out, getting an extra thrill from the fact that nobody who might see us would realise that she had a cock tucked in her panties. I would occasionally brush my hand across her groin as we kissed, heightening our excitement as I felt how hard she was and how tightly pressed her cock was against the cotton that held her in. When we got home, of course, we would quickly ease our tensions, often fucking almost fully dressed, with only her panties off and my pants unzipped, pretending that we were still out there in the park in full public view, and arousing ourselves still more by talking dirty, imagining who might be watching us from behind a nearby tree and wondering if he -- or she! -- could see that Robyn had a hard little pink cock.

One day we were picnicking, and I wondered why Robyn was not giving me the usual teasing glimpses of her panties, but instead was keeping her skirt carefully drawn forward over her knees; at the same time I realised that this was not because she was cross with me, as she was chatting and laughing even more animatedly than usual. After we had finished eating, I was sitting facing her when, finally, she raised her knee for a brief moment, and -- could I believe it? -- it looked as if she was naked under her skirt. I looked at her questioningly, and she raised her knee again, and there it was -- her cock, completely bare and semi-erect, its tip pressing out of her foreskin and her little balls tight beneath her shaft.

We went on talking haltingly for a moment, but our minds were on other things, and she was waiting to see how I would react to this blatant and tantalising teasing. I moved over to lie beside her as she sat, resting on my elbow with my head by her knees, and began gently, with my hand, to stroke her bare thigh. Both of her knees were raised, and I could slip my hand beneath them, with the position of my hand hidden by her skirt. If she could tease me like this, I thought, I could tease her a little, too; and she clearly had no idea what I had in mind or what I could do, in this very public space. So, I softly brushed the underside of her thighs with my fingertips, feeling her wriggle at my touch across her soft sensitive flesh, but not at first moving my hands any further. Her raised knees were together now, and I could imagine her cock tucked down below her thighs; gradually my finger tips began to brush further up, till they touched the crease where her thighs met her pert round butt-cheeks, but for a moment I avoided that little sideways movement that would touch her cock.

But of course I wanted to touch her there just as much as she clearly wanted me to, and, first with my knuckles, I brushed across her balls, and then tickled them with my fingertips, but didn't immediately feel her shaft. She was so hard that it was standing up rigidly in front of her, and when I finally reached up to her tip, I found a huge bead of precum on her, which I licked off my finger before replacing my hand and touching her more, all across her balls and penis and down between the closed cheeks of her bum. Still teasing her a little, I kept my touch gentle and unfocused for a bit, but then took her shaft between my fingers and began to rub her more purposefully. She was as excited as I was, and soon I felt that wonderful, telltale extra stiffening that told me she was about to come, and she spurted into my hand. I put my palm across her tip as she came so that I could catch as much of her spunk as possible, and removed my hand when her spasms had ceased, and then -- openly in front of her and the world -- licked it clean, relishing the thick globs of sweet sticky white cum, before we kissed and I passed some of her fluids back into her mouth.

We both knew it was my turn now, and I manoeuvred my thighs beneath her legs as she sat, still with her knees raised, and with her skirt covering us. When I was touching her, it was not so obvious what we were doing, but now it became pretty clear, though nothing could actually be seen. I unzipped my jeans and at once my hard cock popped out, and I nudged it down below her balls towards the tight little divide between her bum cheeks. At the angle that we were to each other, I could not quite penetrate her, but the feeling of her cheeks close around my cock, and the sensation of my very moist tip tickling the crinkled entry to her anus, brought me off very quickly, leaving my sperm spattered all across her tight little entry and up between her buttocks. And when I moved out from under her thighs, she slipped a hand under herself, brought it up, covered with my sperm, and licked it clean, before kissing me deeply and returning some of my fluids to me.

That summer was full of carnal revelations. We relished all the ways we could touch and fuck each other, and knew that this was the beginning of a long, intense, fulfilling relationship. The autumn came, and the beginning of the college year, and our life together was happy and settled; but it didn't lose its excitement, and part of that was because of the return to the college, after her year abroad, of the cute girl I'd been fucking before I met Robyn. But that story is for another chapter.

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