tagTranssexuals & CrossdressersBest of Both Worlds

Best of Both Worlds


My name is Jim, Jim Naylor. When I got to college, at the age of nineteen, I had a lot of things to sort out. I had spent my last year at school thinking almost constantly about sex, my eyes on fire for almost everyone I saw around me. Yes, I couldn't take my eyes off the girls in their teeshirts and short skirts in the summer, but in the boys' showers in the sports pavilion I couldn't tear my eyes away from the cocks, all shapes and sizes, circumcised and uncut, that I saw all around me. I longed to reach out and touch -- but what? those little breasts through the teeshirts, and feel the nipples harden between my fingers? or those soft cocks as the boys towelled themselves dry, and feel them stiffen and swell in my grasp? And when I masturbated with a pornographic magazine, did I come thinking of it being MY cock deep in those wet cunts, or was it one of the cocks that I wanted, in my hand and plunged into my own body?

At college, I could begin to explore, and in the summer at the end of my first year I began to date a cute blonde girl who smiled at me and talked a lot, and sat on the grass in a loose skirt showing me her white panties -- and then smiled a whole lot more when I kissed her. Yes, we went all the way; I was not her first, and she showed me how to touch and lick her, and invited my hard cock to slip deep between her lips into her soft wet little cunt. Delicious. Now that I was actually doing it, my head was even more full of sex, and I got to fuck her whenever we could -- in our rooms in the college residences, but also out in the park around the college, in the classrooms, and once in the women's toilets one evening, she sitting on my lap facing me, her skirt up round her hips and her little white panties pulled aside, as I sat on the toilet. She loved to suck my cock, but could never quite find the rhythm to make me come that way.

But my eyes were not only focused on her. I still felt that there was something missing, something not quite whole about that little lithe body with the little moist slit between her legs. As I fucked her, I sometimes found myself imagining that a hard cock was springing up out of her pubic hair, in place of her cute little clit. So I found myself drawn to the swimming pool; but it was the changing rooms after swimming that were the main attraction -- and the cocks I saw there, yet more cocks of all shapes and sizes being washed in the showers and dried with the towels, but it was only the owners of those cocks who got to touch them, and I could only dream about what it would be like to touch one apart from my own.

And then I did: late one afternoon I was drying after swimming with only one other guy there, a strong, big guy who looked as if he had been body-building, and with a cock to match. He noticed that I was looking at him; instead of turning away or covering himself up, he walked over to me, and stood stark naked with his long circumcised cock dangling in front of me, and asked me, 'you like it?' I paused, and he said, 'touch it, if you so like looking at it.'

I reached out and took his length in my hand, thrilled to feel it swell so rapidly in my hand. He reached out for me, too, and his touch instantly tingled through my body as he peeled back my foreskin and my cock hardened in his fist. That time, we quickly tossed each other off; I lasted only a very few seconds before I spurted across his thigh, and he didn't take much longer.

Life went on like this in my second college year. I still saw and fucked cute girl, but I also occasionally met the swimmer for hard, impersonal sex -- he liked to lubricate me and sodomise me, lying above me in the missionary position with my knees up to my chest, and I masturbated at the same time so that I came across my belly while he was impaling my butt. He wouldn't let me suck his cock and he never tried to suck mine -- it felt, as he fucked me, as if he was trying to persuade himself that I was a girl and that he was not gay. Yes, his cock excited me and gave me the sharpest pleasure as it brushed across my prostate as he thrust in and out of my butt. He gave me something that cute girl could not, but there was also something about his muscular strength and physical machismo that felt wrong, that left me feeling unsatisfied in my sexual imagination even while my spunk was streaming onto my belly and his into the condom up my butt.

Cute girl had a year abroad during my third year, and the swimmer had left the college; it seemed a good moment to pause and take stock, as I had led two such totally different sex-lives, had enjoyed both of them intensely in purely physical terms, but somehow felt that neither satisfied something deep inside me -- but I had no idea what that something was.

And then I met Robyn. She was doing the same course as me, starting after the Christmas break, a seminar of a dozen people. She was about five foot eight, two or three inches shorter than me, slender, but with a deliciously rounded arse that showed itself off when, as often, she was wearing Levis, and also, on occasion, when she wore loose skirts, demurely down below the knee. There was absolutely nothing showy about the way in which she presented herself. The tops she wore were simple shirts, with sweaters if need be, or white teeshirts, which at least showed me that her tits appeared to be very small but, it seemed, pointed, and that she wore a simple little white bra. Her hair was a soft slightly dull blonde, cut quite short so that is framed her face nicely, but left her neck bare. It would have been easy to overlook her, visually. In class, she intervened regularly, but quietly and unassertively, and only when she really had something to say, and that was usually something good.

Soon we began to chat after the classes, over coffee or a cold drink, until it became a habit that we would leave together and spend the next hour or so going over what had just happened in class; but we never saw each other at any other time. She appeared for class, we had our conversation, and she disappeared; I had no idea where she lived and how she spent the rest of her time. But gradually our conversations became longer, and we started to talk about the other students in the class and the teacher (a man who liked the sound of his own voice), and about our experience of the college. I realised that these conversations with her were becoming an important ritual, and that her presence, and her quiet intelligence and perceptiveness, were something I was coming to see as an integral part of my weekly life. But I still knew nothing about the rest of her life. I was left wondering about her sexuality, and speculating -- perhaps expecting -- that she was quietly gay; but there was something very elusive in the way in which she presented herself physically -- a sort of distance and detachment that was very hard to analyse.

One afternoon, after a seminar in which a couple of students had been particularly irritating, we talked for a while, venting our frustrations about the class, and then I suggested we went off and found a drink somewhere. I had been planning to make this move, and knew a bar not far off campus where we wouldn't be surrounded by familiar faces. She paused a brief moment and then, with a smile, said, 'yes, let's'. There, we talked some more, in very much the familiar register, but gradually I found myself relaxing and beginning to talk more about myself, about my feelings -- and about my sexuality. None of my regular friends knew about my encounters with the swimmer (I am sure they would have teased me if they had), but I found that I was telling Robyn about him, as well as about my time with cute girl, and about the pleasures I had found with both, but also that deep-level sense that neither felt quite right; and of course that meant I was telling her about the sense of confusion that I felt about my own sexuality. It somehow seemed so easy to talk to her about this, and not only because of the bottle of wine we were sharing.

I hadn't really thought about the pressure that my self-revelations would put on her, to talk to me in personal terms about her own life and experiences. She responded very alertly and thoughtfully, engaging with what I was saying and reacting very sympathetically. But she still gave away very little about her own experience, apart from a brief moment when she said, 'I know what you mean,' in response to my talking about my confusion; but she said no more about what she meant by that.

After the bottle was empty, we left the bar. I still knew nothing about where she lived, and she seemed to be going back to campus; I was going off to my apartment, and, as we parted, I reached out very quietly to kiss her cheek; she moved towards me, took my elbow in her hand, and brushed her cheek against mine. It was the first time that we had touched, and the feeling of her hand and cheek, though so light, sent a quick pulse through me. But then, after a smile and a quick thank-you, she was gone, and I went off alone to my apartment, where I found, for the first time, that I urgently needed to masturbate with her in my mind's eye, with the idea of sucking on those little breasts and cupping those round arse cheeks -- but oddly, not thinking about her genitals. And I came so well, so deeply, with a big smile of pleasure, as I imagined her smiling as I touched her.

A couple of weeks later, we were preparing for exams and I suggested she came over to my place so that we could revise together and talk through the issues that the course had raised. She readily agreed, and we spent a couple of hours more, over another bottle of wine, but without any more personal conversation. But at the end, the cheek-to-cheek kiss was noticeably slower and closer; and I was left again to my private and excited imaginings.

After the exams were over, I realised that we now had no more reason to meet, but she had already given me her email, so that we could exchange class-notes, and I now suggested we should meet for lunch one day the next week -- this time, just for the sake of meeting: this would be the big test of whether she would let me become her friend.

And Robyn said yes.

I arranged to pick her up on campus in my car, with a picnic in the trunk and a carefully planned itinerary which would take us to a park some way outside town where we could find some quiet space together. And the weather was kind: warm sunshine all day. And there she was, absolutely on time: wearing a loose check shirt over a white teeshirt, and a pretty, floral loose cotton skirt that came below her knees. We chatted casually as we drove to the park and walked through it, to the spot where I had planned we should stop and picnic -- an open grassy area but in a quite secluded part of the wood, where we were unlikely to see too many fellow-walkers. She liked the picnic I had brought too -- and the bottle of wine (more for her, of course, as I was driving).

We were sitting on the rug I had brought, in the patch of sunlight in this woodland glade, and after a while Robyn removed her shirt; there was one big difference from what I had seen before -- this time, there was no sign of a bra under her white teeshirt. Instead, the cotton clearly outlined what lay underneath -- two very tiny breasts, but each capped with very visible, extended pointed peaks; it seemed as if her breasts were really nothing but those nipples, but those nipples were so enticing. They were not erect now, but I imagined taking them between my lips and grazing them with my teeth, until the teats hardened to my touch.

She must have sensed my focused attention -- it was impossible to hide my interest; and soon it was she who gave our conversation a different turn, by asking me to tell her more about my sexuality, to elaborate on what I had told her before about being torn in different directions by very different desires. At first I hesitated, not being sure quite what to say and what sort of detail I could reveal, but she seemed so much at ease as she asked the question that I gradually felt able to tell her more -- not only about the almost painful pleasure that I had got from the swimmer's cock brushing my prostate, but also about my imaginings of a hard cock springing up from cute girl's groin as I fucked her. Here she reacted with a slight smile, and asked me straightforwardly what I had fantasised about doing to cute girl's little girl-cock. First, I told her, I'd like to tickle it gently with my fingers as I went on fucking her, but what I really dreamed of doing was going down on her, taking it softly between my lips and rolling my tongue around it as it stiffened and its tip emerged from the foreskin (I had always imagined it being uncut, unlike the swimmer's big member). I would then gently and rhythmically suck it, to see if I could make her come in my mouth.

It was very strange, talking in such detail like this about my fantasies. I felt as if I was going into a sort of trance that allowed me to conjure up these images, and of course my body reacted, too, and I began to stiffen in my loose summer trousers. But at the same time I was very aware of Robyn following my every word, looking intently at me with that slightly quizzical half smile, and occasionally shifting slightly as she sat on the rug, with the hard ground beneath. At one point, she moved her legs, and I caught a glimpse up her loose skirt, seeing pale thighs and a broad swathe of white cotton covering her crotch; my cock twitched eagerly, but it was only a momentary glimpse before her skirt again covered her.

By now we had finished the picnic and had drunk most of the wine. Robyn then announced she had to pee, and walked off into the edge of the wood. I could just see her where she stopped, and watched as she crouched down with her back to me; but the foliage around her meant that I could see no more. She came back, still with that slight smile, and I got up for my own pee, and followed her example, but standing, of course, with my back to her as I peed, in the edge of the wood.

When I got back I knew I had to make some sort of move. Before, I had been sitting opposite her; now I sat beside her, and much closer than before. We both knew that something had changed, and our conversation became aimless and halting for a moment -- commenting on the trees, the weather, and other trivial incidentals. And then I put my arm round her shoulder -- that crucial move that determines success or failure! Only a brief pause, and she leant gently towards me and put her head on my shoulder. I moved my hand to stroke her neck and her hair, and then turned to face her, inviting her face to meet mine. Her expression was very serious (no more half-smiles now) but she moved towards me until our lips touched -- not just cheeks this time. And then we began to kiss. Like everything else in this strange, quiet relationship, everything moved slowly; no suddenly opened mouths or plunging tongues, but instead lips gently brushed together, gradually more firmly, and then her lips opened a very little, as she momentarily touched my lips with her tongue, and accepted mine in return.

My other arm now reached round her and began to stroke the side of her teeshirt, moving ever closer to her tiny breast, brushing towards this very visible little peak that I longed to take between my fingers. When finally I did, she immediately shivered at my finger on her nipple, but made no move to stop me, and I softly began to stroke her through the cotton, thrilled to feel the teat harden to my touch. At the same time she reached out to me and brushed her fingers across my little nipples through my shirt, and I shivered as she had: how could she know that my boy-nipples were so sensitive? And it was she who made the next move, unbuttoning my shirt and slipping her fingers into it, to brush the bare surface of my now-hard nipple. I gave a sudden deeper shiver, feeling that strange mini-climax that I had occasionally felt when I was touched, not on my cock, but on other very sensitive parts of my body.

I took this as an invitation, and pulled her teeshirt out from her waistband, and began to run my hand slowly up her belly and up to her breast. How extraordinary it felt! It had virtually no flesh around it, as I had realised, but the puffy nipple itself was like a rich soft fruit, protruding from her chest; and she shivered, just as I had, as I touched it, and shivered again as I very gently took it between my finger and thumb and rolled the soft skin with that harder centre to and fro. We were now kissing more deeply, our mouths open and our tongues playing against each other, tip to tip, and I could feel her gently moving against the ground as she sat on the rug, moving in time with my fingers as they played with her so-sensitive nipple.

Of course I was aroused by now, but I sensed that we couldn't go any further where we were in the woods; a few people had passed nearby, and there seemed no need to get into an awkward situation if anyone else appeared at the wrong moment. But it was Robyn who said, maybe we should go somewhere else, and I agreed at once.

We gathered our things and left the park, and she quickly agreed when I suggested we should go to my apartment. As we drove, our conversation went back into everyday mode, and when we got to my place we continued to chat for a while, seated side by side on the big sofa, as if nothing had happened. But very soon the conversation again became halting, as we both realised that the next step was just ahead -- whatever that step would turn out to be.

'You're sure this is what you want, Jim?' she said, turning towards me and looking at me questioningly.

And then we were kissing, mouth against mouth, tongue against tongue. As I felt to put my hands under her teeshirt again, she quickly pulled the shirt off, leaving her breasts quite bare, their big tips standing out vividly against her chest. I followed suit and took off my shirt, and then felt her flesh against mine for the first time, before leaning forward and taking a nipple in my mouth. A sharp intake of breath as the nipple hardened and she shuddered; I went on gently licking around the bud-like tip, occasionally sucking her slightly more firmly, and again making her shiver through her whole body. She reached out, too, to touch my nipple, and, saying 'my turn now,' she leant over to suck it, sending a startlingly intense pulse through my whole body.

To reach me better she kneeled on the floor beside the sofa, between my knees, and, as she leaned forward to suck my nipple her whole bare upper body pressed against me, and she could feel for the first time my erect cock inside my loose trousers. Of course she knew just where she was going now, and she slowly moved her mouth down to my belly, undoing my belt and unzipping my trousers as she did, revealing my full length through my small cotton briefs. She knelt back for a moment and looked down at the cotton-covered shaft that she had exposed, and then ran a hand slowly down my length, before reaching out with the other hand and beginning to work it up and down on me. But this didn't last long, and she began to peel down my briefs, smiling as she revealed the head of my cock, protruding out of my soft foreskin.

Without pulling them down any further at first, she lent over and planted a soft kiss on my tip, and began gently to lick round the base of the helmet -- perfect! just where I am most sensitive; and then, in a single move, she pulled briefs and trousers right off me, so that I was completely naked as she knelt between my knees. She now took my tip in her mouth again, and began to suck me, but also with her hands began to feel round and below my balls, touching so lightly that she was almost tickling me, and brushing down once or twice between my bum cheeks. She then began gradually to strike up a rhythm between her mouth and her hands, with one hand grasping the base of my shaft quite tightly while her soft moist lips teased around my helmet. It didn't take long for me to realise that I was on the way, and, as she sensed this, she began to pump the base of my shaft more vigorously, until I gasped, 'I'm about to come,' to give her the chance to take me out of her mouth. But instead she looked up at me for a second, and then wrapped her lips right around the tip until I exploded in spurts into her mouth. After the last spurt, she looked up again, this time with a much bigger smile, and a little trickle of my cum at the corner of her mouth.

Report Story

byHippoid© 0 comments/ 109466 views/ 35 favorites

Share the love

Report a Bug

3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: