Me and a Prostate

We were both finding our way, I think…certainly I was. He was going to be my very first fuck, and although I’d read the book (hehehe) I had little idea what it would really be like. It’s very different fucking yourself with a candle, which is something I did regularly at that time, and being fucked for real. 

It was, looking back, like a mini affair. We were only together for about three months, and even then it was quite off and on, but, well, you know what it’s like when you start having sex with someone. I suppose it was more friends with benefits than a love affair. I wanted to be fucked…he wanted to fuck me. In between times, we both saw other people. 

So, one afternoon, we were lying on his bed. I had gone back to his home after school and we had fucked. As I lay next to him Miss Brain tapped me on the shoulder, took control of my mouth and made it ask him, “is there anything you’ve always wanted a girl to do but haven’t asked for yet?” 

He became embarrassed and I knew I was onto something, but whether or not I could get him to tell me was another matter. It was when I was on my period and we didn’t fuck (I would have, but he wasn’t keen) that he finally told me, after much hesitation, that when he jacks off, he likes to have something up his bum. 

Now, I’d heard of this prostate thing, but didn’t have a clue where it was. I knew my bum hole was exquisitely sensitive, and maybe that’s what he meant. I also knew, from fingering my vagina, that I had many different areas up there. My G-spot is easily palpable as an area of rougher skin. Sometimes, I can feel my cervix too and moving it feels really good. Plus, if I hook a finger forward I can press on my bladder which feels amazing. The point I’m making is that it isn’t just a hole.

So, with him naked and me my bra and panties (he loved cumming on my bra and panties when I was on.) I began to Jack him. I had the presence of mind to take his lube with me as I lay between his splayed legs. I worked him up until I saw pre cum forming, and then I went in search of the mysterious prostate. 

Lubricating my finger was easy enough, I had overdone it on his cock and there was plenty of surplus around. Then I found his bum hole and pressed gently. My finger slid in easily and I felt around. Nothing. He said, “Deeper” and I figured what the hell and pressed in further which he obviously liked. For some reason, I though this hidden prostate was towards his back, so I gave a little press in that direction but I knew from his reaction that that was wrong. Again…”Deeper….please…and press towards my tummy, not my back.” 

So there I lay, his steel-like cock in my right hand and my left middle finger all the way up his bum. Then I turned my hand over so I could press my finger up towards his tummy. I could feel something hard and pressed it but not too firmly. He arched his back and uttered a sibilant, “Yesssssss”. But I didn’t know whether I should just maintain pressure or what I should do. Fortunately he supplied the answer. “Keep just that amount of pressure and…fuck me.” And so I fucked him with my middle finger up his bum. 

Well, his orgasm was enormous and better still, I felt it through his bum hole…the contractions weren’t unlike what I feel when I finger my bum and masturbate to orgasm. Well, a girl learns something new every day, it seems. 

It didn’t end quite there though. Over the next few days I would Jack him off in the same way. After one such time, I said “It’s similar to fingering a girl.” He responded immediately with “Sometimes, that’s what I imagine I am.” Miss Brain filed that one for later. 

Fast forward to my last period when we were a sort of item. Before I tell you about it I should mention that our sex life, while ‘ok’ wasn’t what you would call a fuck-fest of exploration, desire and discovery, and sometimes, I got the distinct impression that he was rather glad when I came so that he could, and then the sordid business could be over. But he did like me masturbating him during my time of the month. 

Enter Miss Brain. 

Again, we were in his bedroom, and I’d just told him my monthly visitor had arrived. He seemed quite excited and asked if we could ‘Do that thing’ as he called it. So we started kissing and slowly undressing until, as usual, he was naked and I was down to my bra and panties. Then Miss Brain took control. I reached around myself and undid my bra. By this time, he was lying on his back on the bed and I was on top of him, and when my bra fell off down my arms it landed squarely over his chest. Miss Brain caused me to say “Oh, THAT looks sexy!” I turned the bra the right way round, put it on him and reached underneath him. I had only intended to tuck the ends in, but he arched his back so I could fasten it….just. 

Now, suddenly, I knew not only where this was going, but also that our relationship…such as it was….was probably not going to last much longer. I felt a pang of sadness hidden amongst the sexual arousal. 

I slipped my panties off and Miss Brain turned into ‘bitch mode’. “A good girl should always have her panties on….and you are a good girl, aren’t you?” And almost dreamy, “Yes” came from him as I eased my panties up his legs, leaving his cock sticking out of the waistband. 

Then, the usual procedure, but this time, Miss Brain added a sound track. “God….you’re so wet. Have you been this wet in school all day, your panties are soaked.” He murmured something I didn’t quite catch, but his body language told me I was on the right track. After the usual masturbation to pre-cum, which was far quicker than usual, I asked “Has anyone fingered you before…have you ever had someone’s finger inside your vagina?” He shook his head, too lost in the world I had created for him to speak. I pulled the panties aside and slipped my finger up inside his bum telling him how tight his cunt felt and to trust me.

Then I proceeded to finger fuck him just the way he had taught me that he likes, but maybe a little firmer. I had no idea if prostates can be bruised by too vigorous stimulation (unlike cervices, which, I now know can be). All the time, I kept up a feminising dialogue for him which he really enjoyed, especially when I told him I was going to smell his panties and lick them. The moment I told him I could taste his cunt, he exploded…and yes…that’s the only possible word. It was far and away the longest orgasm I had ever seen in a guy before or since. Semen just kept coming….and coming and coming. Think of When Harry Met Sally, and you’ll be about right…IF YOU MULTIPLY IT BY A FACTOR. OF TEN. 

I loved having my finger deep up his bum though. There was definitely something naughty…taboo…whatever the damn word is.

We drifted apart shortly after this, although I did get to feminise him a couple more times, each time going further. The next day, for example, I got him into my complete school uniform. I even gave him a name…Jessica. 

You probably won’t be at all surprised to learn that he is now awaiting gender reassignment surgery. He’s been living as a girl for a little over a year now and is taking hormones and all the other things transsexual people have to do. It isn’t an easy path for him especially here. 

Oh, one more thing. His chosen girl’s name? 

Take a guess.