Best of Both Worlds

How did she know how to do that so skilfully? how did she sense how to hold, touch, lick, pump my cock with just the right pressure and timing -- so unlike the many occasions when cute girl had taken me in her mouth?

She came up now till she was lying against me, she still wearing her skirt and (I assumed) her panties, me naked and deflating after my climax. But soon I said, my turn, now, and moved round to kneel between her knees. As I did, she held me back for a moment and looked questioningly at me, and I responded with a reassuring smile, so that she let me part her knees, still covered by the loose skirt. I first stroked her thighs through the fabric, and then slipped my hands onto her bare calves, then her knees, and then, slowly raising her skirt, onto her thighs, and she sighed quietly as I began to stroke up and down the soft flesh of the insides of her thighs. I could sense that she was not really relaxed, and took it very slowly, relishing the textures of her without going any further for the moment.

But my hands were slowly working further upwards, and the tips of my fingers brushed a couple of times against the edge of the elastic of her panties. She again looked at me questioningly, and I again smiled my reassurance. And then the moment came, as I reached out to touch her between her open thighs, reached out towards the centre of those soft white cotton panties -- and found that I was feeling a rigid, hard cock.

She began to say, 'is that really OK, Jim?' But I gave her such a broad smile that I stopped the phrase on her lips almost before she had finished it. But I was also amazed, and asking myself whether, at some level, I had realised what I was going to find. I certainly hadn't explicitly asked myself whether she might be a she-male, but at the same time I had sensed something about her sexuality that had allowed me to talk to her about my sexual experiences and fantasies in a way I never could have with a woman.

But this wasn't the time for self-analysis. What I had in front of me and beneath my hand was the stuff of my dreams, of my most extravagant fantasies -- a beautiful, gentle, thoughtful, sexy girl, who had a hard cock. I lifted her skirt right up so that I could see its length; quite slender, and maybe only four or five inches long, but there was already a delicious wet stain of precum on her panties. And now it was my turn to peel the panties down, and the sweetest little pink tip appeared, uncut, like me, and virtually unsheathed, and I leaned over to kiss it and lick off that sweet bead of precum for a moment before pulling the panties right off, and she quickly undid and removed the skirt, too. And there she was in front of me, completely naked, and hairless, it seemed, and with this pale pink shaft with its much richer pink helmet jutting out so invitingly above a sweet little pair of balls and the crack between her bum cheeks.

Another moment of giving her the warmest and most reassuring smile, quietly breathing the words 'oh wow!' Then I put my mouth down and took her hard little shaft between my lips and cheeks, trying to take it deep inside me, and at the same time licking round the tip. It was the first time I had had a cock in my mouth, and I was astonished at the feel of it, as I rolled it around with my tongue and felt it moving inside me. After simply relishing the feel of it there for a while, I began to stroke her little balls and to touch the base of her shaft as she had mine, and to strike up a rhythm. I didn't know how easy it would be for her to come, but I soon found out, as she began to gasp and to push down on my shoulders with her hands, as if willing herself ever deeper inside me, and her hard little cock suddenly became much harder. Her breathing quickened as she began to gasp -- and then she was spurting deep down my throat, and I could feel the liquid as it pulsed out of her and she filled my mouth with her extraordinary salty cum.

A quiet pause, and I looked up at her and saw the broadest, most serene smile on her face as she whispered, 'thank you!' 'Let's go to my bedroom,' I replied, 'it's more comfortable there.' Utterly enthralled, I walked behind the swinging, round cheeks of her bum, realising just how much we had to talk about -- and how excited I was at the prospect of finding out the secrets of her sexual life, as she had already found out mine.

But talk wasn't top of the agenda yet, when we got to my bed -- tidily made up with clean sheets in the distant hope I might have her company, but without realising what sort of company that might be. First, we simply lay down and looked at each other, naked, face to face, but only touching by holding each other's hands. Time seemed to stand still as I gazed with utter delight at her tiny breasts with their buds -- and down to her little shaft, soft now, with its tip retreated into the foreskin, but moist with the final beads of her cum. And then we gradually began to kiss, deeply, fully, mouth to mouth, body against body, and I felt the delicious soft detail of her cock rubbing against mine -- and wasn't hers harder now that when I had been looking at it? mine certainly was. I reached down between us and had the thrilling experience of holding our cocks together in the same hand and feeling them both swelling as I gently squeezed them together.

I toyed gently with her for a while until she was completely hard again, while all the time my cock was hardening alongside hers, and she said, 'please, Jim, will you fuck me?'

She lay on her back with her knees up and opened her legs wide, a beautiful open woman's body, with her soft nipples and her fair, hairless skin, and the round cheeks of her butt showing as she lay there -- and with just that one extra, her hard little cock standing there like a giant erect clitoris. I knelt down between her knees, took that cock in my mouth again for a moment, but then kissed further down, licking across her tight little balls, their puckered skin holding them close beneath her shaft, and then on downwards, running my tongue down between the cheeks of her arse as she pulled her knees up to her breasts, and focusing on the little opening there. She gasped when my tongue first touched her anus, and wriggled as I gently probed it, trying to soften her and moisten her a little, to make my entry easier. At the same time, I couldn't keep my hands off her cock, and stroked it up and down in time with the movements of my tongue.

'Please, I want you,' she said, and I got up from her and found the tube of lubricant I had in my bedside closet. 'Let me moisten you,' she said, and she anointed her hand and softly took my cock between her fingers, while I lubricated her anus, pushing my fingers carefully past her sphincter and opening her out a little, before I knelt up over her, my cock standing out in front of me, as I looked down on her open body with its hard little girl-cock standing out against the bottom of her belly.

My cock was something different from my fingers, and she gave a little gasp when I began gently to push it into her. To start with, I just rubbed myself in and out of the opening, so that she was fully lubricated and could begin to relax, and then a push, another deeper gasp from her, and I was inside her. A pause, and then I began slowly to move in and out, with the amazing tightness of her sphincter holding my cock in place as I felt her wider channel inside. As I moved, I felt down and held her cock, at which she said, 'oh yes, please!' I began to find a rhythm with my hand and my cock together, and she began to move her hips in time with me, as I gently probed deeper inside her.

And this was the dream that I had had before, when I was fucking cute girl -- the vision of my cock deep inside a girl's body, but with a hard cock rearing up, for me to stroke and caress; but the reality, as I probed Robyn's anus and caressed her rod, was so much more intense than I could ever have dreamed.

Her movements began to quicken again and her cock to harden still more in my hand. 'Oh God,' she said, 'I'm going to come again,' and I suddenly felt my own climax welling up inside me as my cock brushed her prostate and her sphincter tightened around me. 'Me too,' I gasped, and the spasms hit us both together as I pulsed deep inside her butt, and her spasms matched mine, as her cum sprayed across my hand and onto her bare belly. My cock quickly slipped out of her wet distended butt-channel, and I rolled over to lie beside her, my hand still lightly holding her soggy, softening little cock.

We dozed for a little, our bodies curled round each other, until she stirred and said, 'I need to pee.' 'Me too, and I need to wash,' I replied, and followed her to the bathroom, still thrilling at the movement of her round ass-cheeks as she walked, and wondering how she would choose to pee, seated, or standing like a boy. She sat down and with a sigh and a quick smile began to pee, with her jet loudly splashing in the water, and I stood in front of her watching, but at first seeing nothing, as her little cock was turned down below her closed thighs. But when she saw me watching her, she gave a quick mischievous smile and opened her knees, and I saw the final squirts of pee coming out from between her rosebud-like foreskin. She watched as I in turn peed, and then we showered together, each soaping the parts of each other's body that needed the most attention. I softly pulled back her foreskin and stroked her exposed tip, and she did the same for me, carefully soaping the length of me and washing inside the foreskin; my hands also felt round and soaped between her butt-cheeks, tucking a finger carefully where my cock had just been and washing away the dribbles of my cum that were still trickling out of her.

Wrapped in towels, we went back to my bed, and she began to talk. Her name as a boy had been Robin -- of course! But by the time she was twelve or so she had come to feel increasingly uncomfortable about boyishness; she had an older sister, and had a few times tried on her white cotton panties when nobody else was in the house, and it was in a pair of her panties that she had had her first erections, and then, when she was fourteen, her first climax. However, through her high school, she had gone on living as a boy, dressing very anonymously and sheltering, as best she could, from all the adolescent byplay by being a nerd and immersing herself in her school work. She found many of the girls in her class very pretty, but she hadn't felt turned on by the idea of touching them -- or of them touching her cock; and when she masturbated she found that the images before her eyes were from the boys' changing rooms, where she had first glimpsed other cocks, most of them bigger than hers. She loved the feeling of stroking her own cock, but came increasingly to imagine that it was a special sort of clitoris, and that it was a boy's mouth around it as she stroked herself to climax.

She had gone to college, too, as a boy, again focusing on her studies and keeping herself to herself, but watching, constantly watching, to see how the rest of her generation engaged with each other, flirted with each other, kissed each other. And beneath her boy clothes she now was always wearing girls' panties, as she liked the way they held her cock close to her body, and when she went to the men's toilets she always used a cubicle, because of the panties she was wearing, but also because she found she liked to pee sitting down with her knees together, so that when she looked down all she could see was a little V of pubic hair. But she still loved to masturbate, and filled many pairs of used panties with the spurts of her cum.

There had been a moment in the second semester when everything had come to a head, and she had gone to the counselling service to talk about her predicament. The first counsellor -- a man -- hadn't been very sympathetic, but had referred her to someone else who took her situation very seriously. This second counsellor -- a woman -- realised that Robin really did think of herself as a woman and wanted to live as a woman; she asked her carefully whether she wanted to have the full operation. This was a question that had been bothering Robin, as part of her felt that she should indeed have a cunt, but at the same time she loved what she thought of as her magic clitoris, and loved the feelings it gave her when she masturbated, and she could not envisage losing this. The councillor suggested that she should start some sort of hormone treatment, but should try to strike a balance so that she wouldn't lose the sexual use of her cock. She had taken this advice, and had found that the slight changes in her body -- less body hair, enlarged nipples -- hadn't stopped her cumming.

But she was still living outwardly as a boy, as Robin. In the spring break she had summoned up the courage to tell her mother about her feelings (her father had left them, years before), and had been amazed by her sympathetic and understanding response; she must have guessed, Robyn realised, that something like this was going on. But they had both realised that, if she was going to live as a woman, if Robin was going to become Robyn, she would need to move to a different university. So, in her second year, she had joined the college where I was studying, now as Robyn and living as a woman, her girl-cock tucked safely into her panties, but brought out in the privacy of her room so that she could play with it, and think about her lips closed around the tip of a boy's cock as she coaxed her own to spurting climaxes in those panties.

She had dressed as unobtrusively and as anonymously as she had when I first met her, a year later. She had never wanted large breasts, and at first had needed to put a little cotton wool into her bras, but now her breasts had grown enough for her to wear an A-cup with no padding. Understandably, she had been frightened at the prospect of getting sexually involved and wary of attracting too much attention from boys. She had had one boy take an interest in her, and they had begun to kiss, and she had let him stroke her little breasts, which had sent tingles all through her, but she had had to take great care not to let him sense the little shaft that hardened in her panties as he touched her nipples. She did, though, touch him, and happily he had seemed well satisfied by the attentions of her hand and her mouth; she developed her skills as a cock-sucker so as to bring him off before he wanted to get inside her panties. And she now had ample memories to play with as she stroked herself to climaxes after their encounters, imagining his cock between her lips.

He had left the college at the end of that year, and in the next -- the year we were now in -- she had had just one sexual encounter, but one that had alarmed her as much as exciting her. At a party she had for once had too much to drink (she was normally very careful about this), and had found herself flirting with a boy and then kissing, and had gone back to his room with him. She sobered up quickly when she got there, realising what she was doing, and hoping that he was as drunk as he seemed; she told him that she liked it from behind, and had managed to pull down her panties and take him up her butt without letting him feel any further forward beneath her skirt. He had come very quickly and had immediately rolled over and gone into a drunken sleep; she had no idea whether he had thought he was fucking a cunt. But, despite her anxiety and her fears of being unveiled, she also had been excited by the feeling of his spurts deep inside her arse; more fuel for her solo sessions, masturbating into her panties.

When she had met me, she told me, she hadn't at once thought of me sexually, and had been very relieved that I had not come on to her, but had seemed satisfied by just talking and hanging out with her. She had been surprised by the first occasion when we had gone to the bar and I had begun talking about my own sexual ambivalence, but, as she thought about it afterwards, she had become more and more interested, and had begun to wonder whether she might be able to reveal her secret to me -- and yes, she had begun to imagine it was my cock she was sucking as she masturbated. She had thought hard about whether she should reply to my message after the examinations, realising that this would open the door to a friendship of a different sort, but had decided to take the risk.

And the final decision, she said, had been oddly easy, when I had told her, in the park earlier that day, about my fantasy of cute girl having a cock I could masturbate while I fucked her, and then suck to climax. Robyn still hadn't known whether I would find the reality exciting (some fantasies are best left as that, as mere fantasies), but she realised that she needed to let me reveal her sex, and live with the consequences, whatever they were. And now she knew she hadn't made a mistake.

While she talked, I said virtually nothing, but held her gently and looked into her eyes, reassuring her that I was with her all the way; and as she began to talk about her sexual experiences I began to feel myself hardening again, but resisted the temptation to start of touch her sexually; I knew that she needed to get to the end of her story, and I wanted to hear it, to understand how she had been able to let me so far into her life -- and her secret.

'I need to pee again,' she said as she finished. I followed her into the bathroom. 'Do you want to watch?' she said, 'if you do, maybe I should do it standing up. That'll feel very strange -- I haven't done it that way for years!'

So she stood in front of the bowl so that I could watch her, and she held her cock as she began, rolling the little foreskin back as the jet sprayed out of her. After a moment I reached out and touched the little tip, and she took her hand away, letting me hold it and feel the pulse of the jet running through it. I quickly knelt down so that I could see it more closely, and, as the continuous jet gave way to quick little spurts, I reached forward and took one of them in my open mouth; and as she finished I took the whole tip of her cock between my lips, licking round the tip and under the foreskin to clean her -- and to thrill myself.

But the greatest thrill was that she began to stiffen again in my mouth. I sucked and licked her as she stood in front of the toilet, gradually taking her further and further into my mouth as she grew longer and harder. She looked down, seeing my erection, rigid and ready again. 'Maybe we should go back to the bedroom,' she said with a smile.

This time we lay down in a sixty-nine position; I didn't want to stop sucking that little hard fair-skinned cock, and she didn't want to let go of me. She moved her lips on my cock, letting me fuck her mouth as I licked up and down along her length. But I didn't want us to come again this way. There was one more dream to fulfil -- I wanted her to ride me. With cute girl, I had sometimes fucked her while lying on my back with her sitting across me, but I had felt most excited in this position when I was not penetrating her, but lying with my erect cock standing out in front of her as she rubbed her clitoris against the base of my shaft; sometimes she had masturbated my cock in this position and sometimes I had; but I made myself come by imagining that the cock I could see in front of me was springing out of her loins and not mine. That image, of cute girl with a real cock, had been one of the most vivid memories I had held on to when I masturbated.

And now I could fuck a real girl with a real girl-cock that I could masturbate while I was impaled deep in her butt-cunt. I lubricated myself again and entered her more easily than last time, and she began to ride me, with little sighs each time my cock penetrated her more deeply. But my focus was on what was in front of her -- on her little cock, fully hard now, and moving slightly each time I thrust in and out of her. I reached out and began very lightly to touch her up and down the length of her shaft, and then grasped it and began to rub it more firmly, delighting in the reappearance of her foreskin around the tip each time I pulled my hand up on her, and then seeing the tip -- a rich purply pink now -- re-emerge with the downward movement of my hand. The sight of this very soon brought me off, deep up her butt-cunt; she then collapsed across my body and my cock slipped out of her, and we lay holding each other tightly for a moment.