He Told Me to Fuck Him!

Chris, Alison’s boyfriend is straight. Not ‘fiercely’ straight, and certainly not homophobic ally straight - he just likes vagina - in particular, Alison’s vagina - but then I quite like her vagina too!. Since that’s out of commission just now, as I’ve told you the arrangement is I fuck him twice a month. I get my desire for cock fulfilled, he gets a good fuck out of it, and Ali doesn’t feel guilty. Everyone wins. 

Sometimes he is tender and gentle, sometimes he is so desperate I get what amounts to a gloriously savage pounding….there will also usually, whatever his needs, be seconds and thirds the same afternoon.

So, this particular afternoon, we had fucked and were lying there, sweaty and satisfied, just talking about sex acts we had tried and liked, including those we had never tried but wanted to. (Not many of those in my case.) Chris told me that sometimes, when Ali goes down on him, she works a nice, wet slippery finger up his bum. “I shouldn’t like it,” he said, “but the thing is, I really did.” Why on earth he shouldn’t like it I don’t know, but it appeared he is one of those “if you play with my bum and I like it, it makes me homosexual” sorts, which, I admit, I found disappointing. I asked how far in Ali got her finger, and it turned out it was all the way -  Ali has long fingers. 

There was something in his tone that woke Miss Brain up. ‘He’s asking you to finger his bum’ she told me. Sometimes, I am less than astute when a hidden request it made and Miss Brain knows she needs to poke me with a stick sometimes. 

So, after about another fifteen minutes of sex chat, Chris began to become erect again, and I kissed him before kissing south and taking his cock in my mouth. What a pleasurable taste it is when a cock is covered with cunt on the outside, yet salty at its tip. Yummy! As I sucked him, very slowly I moved from gently caressing his balls to reach between my legs and get my middle finger well and truly wet - no problem there since I was dripping with both me and copious amounts of semen. The first touch or two at his bum mole was purely to spread the oily substance around, dipping back between my legs for more as needed, but then I began to ease my finger inside. 

He was tight. Tighter than Emily or Alison, but then both are used to anal stimulation, including being fucked ip the bum regularly. 

Time for another poke from Miss Brain. “Are you paying any attention here, you dumb bitch?” Charming, but then sometimes, Miss Brain can be insulting…deliciously so at times. She was, as she always is, quite right. Something had changed. Chris has his feet drawn up and his legs flopped wide apart. He cycles for sport, and, like most cyclists, has no leg hair….his legs looked quite feminine. I reported back to Miss Brain that I had, thanks to her, noticed the feminine position he was in, especially since when I’m sucking him off, he usually has his legs out straight and clamped tightly together. 

“You really can be so fucking slow at times….listen! Just….listen.” Down at the business end, blow jobs can get a little slurpy, especially if, like me, you like giving them as deeply as you can. There’s noise. So I cooled what I was doing down a grade or two and listened. Chris was whispering “Fuck me….fuck me….” Huh? What do I do with that? I already had a finger deep in his bum. 

“Oh for fucks sake” Miss Brain spat exasperatedly. “Here, let me.” She grabbed both the movement controls and my speech centre and made me stop everything apart from my finger up his bum. I knelt up on the bed and said “I could, you know…if you’d like me to.” He looked a little scared but said 

‘You could what?”

“I could fuck you”

“What…more than you’re doing already?”

I said ‘Yeah - let me show you.” 

Reclaiming my finger I bounced off the bed (mistake, since it sent a flood of semen onto the floor and down my legs) I grabbed ‘Mike’ and showed it to Chris. “We bought this for several reasons. First, it doesn’t look like those hideous scrappy things - it’s just a pair of panties to which you can attach a cock. Second, the cock concerned isn’t a 9 inch monster three inches across. In fact we deliberately chose this one which is a little on the small side. It’s good enough for vaginal fucking, maybe a bit small, but remember, Emily doesn’t have much experience of that. We really chose it for anal sex with each other. Precisely because of its size, and the fact it isn’t a rigid piece of plastic - there’s some give in it - so, if you want….” I left the sentence hanging just to see what he would say. 

In the end, he said nothing, and it was up to Miss Brain to slap me round the tits and remind me that silence breeds assent. “He doesn’t want to actually say yes, but look, you fucking moron, he has closed his eyes and relaxed his body - he’s just waiting for you, for fucks sake!” 

I can take my panties off in less than a second, and it appears I can put a pair on just as fast. A good liberal squirt of ten of lube and I positioned myself between his still spread legs. Images of how he fucks me flitted through my head but were firmly rebuffed by Miss Brain. “Think of it as taking his virginity.” Well, no good thinking of when I lost my cherry - which was to a candle hall in my own right hand. But I’d heard enough from other girls who lost theirs to a cock to know how to proceed. 

Looking at Chris lying there, something definitely felt different….feminine…almost, dare I say, delicate? I had to move his feet out sideways to get where I needed to be and gently, very, very, very gently pressed ‘Mike’ against his bum. I felt some yielding and slowly, more slowly than you can imagine, I kept up just enough pressure to ensure movement. Not for the first time, I cursed the fact that of course, I coundt feel anything except a slight pressure against my pubic bone. What must it be like for guys who can feel something along the entire length of their shaft? 

So finally, I was so far inside that I had to remove my hand or i would get no further. The last centimetre or so slipped in and I just held still. His cock was like an iron Rod standing straight up in the air and leaking pre-cum profusely. Then there was that whisper “Fuck me. Please…fuck me.” And so I did. If anyone had fucked me that gently, I would kick them unceremoniously through the bedroom window, but Miss Brain was in charge now and clearly knew what should be done. Gently, in fact, barely moving at times. The look on his face was beautiful….pure, unfettered ecstasy. Now and then a “Faster” or ‘Harder” escaped his lips as barely more than a whisper. Throughout this his eyes were tightly closed and I can’t imagine what he was thinking about - Miss Brain instructed me in no uncertain terms not to inquire.

She did, however, make me lean forward and lie flat on top of him, his iron hard cock trapped against my tummy, and my legs extended between his - classic missionary! I fucked, Chris moaned and gasped and then his eyes screwed up and his brow furrowed and I didn’t need Miss Brain to tell me what was about to happen. He didn’t (much to my disappointment say ‘Cum in me’. In fact he didn’t say anything intelligible at all….instead, I felt wetness between us spreading rapidly across my tummy. I risked a quick look between us and was rewarded by a shot of semen, more powerful than any I have ever witnessed hit me square in the eye! The rest, I made sure, stayed between our bodies. 

Miss Brain told me to pull out just at the end of his orgasm. How the fuck do I know when that was? I didn’t, but fortunately Miss Brain could read the signs. As I pulled Mike out it prompted another angry-looking ejaculation which, given I was sliding down Chris’s body at the time, I was able to catch in my mouth. I really do like swallowing semen!

“Now” said Miss Brain, using her sternest teacher voice “don’t say a fucking word.” So, we lay there, as usual when we’ve just fucked. The fact that I’d just fucked him up the bum seemed to evaporate into the heavily sexual scent pervading the bedroom. 

Again, after a while of recovery, he began to talk, this time about Alison…about how she has told him everything about what we did to and with each other and how much had been incorporated into their sex life before the doctors had told her no more for a while. They role,play like we did, they pee for and on each other, they’ve role played Alison being me, and they’ve even used my panties - both of them together…this was just before I moved out. They’ve also, like me, indulged in age play, with both of them taking the under-age role in turns. I’m so glad Alison learned so much from me! 

It took Chris much, much longer to even begin to show signs of a third erection this time. Again, I felt that familiar poke with a stick from Miss Brain. I’d missed something. I miss nothing when I’m with another girl. Nothing. Ever. I pick up on the smallest nuance, the slightest hint. But I am just not as attuned or, ( it has to be admitted) as interested in men. The poke with the stick this time came from Miss Brain noticing the slightest imaginable change in his voice when he said the word ‘age-play’ and when he had said that Alison makes a great 15 year old.” Just an added huskiness… slight pause in the flow of the sentence. 

Both Ali and I are small boobed. Both Ali and I are on the short side, and both Ali and I have no pubes - well, I imagine Ali does by now. confined in hospital for two months now, she must look positively pubescent down there. 

I flopped back onto the bed, while Miss Brain cobbled together a quick scenario. It came in a micro-flash of something - inspiration? Guesswork? The workings of a deliciously perverted mind? Who knows? Who cares? 

I jabbed him hard with a finger which made him jump. “What the fu…?”

“Hey bro, can I ask you something kinda private?”

Before he could respond I ploughed on.

Well, I know you Jack off, right? And I know that when you do, this stuff comes out. Well, I was goofing around with my boyfriend and this stuff ended up on my tummy…look. Is it, you know, spunky…semen?” 

He slowly cottoned on that I was playing underage for him. 

“Well, yeah, it is, but you really shouldn’t be doing this at your age you know, I mean how old are you now, 15?” (Time to push the envelope in two directions at once. 

“Well, that’s fucking charming! You’re my brother! You should know I’m 14!” The twitch in his cock told me that, as usual, Miss Brain had got it spot on - again - (don’t you just hate some people?)

“Ok sis, well, it certainly looks like cum, and smells like it…ew…go and wash! I don’t want another guy’s cum on my bed!” I skipped off to the bathroom as ‘fresh young and innocent’ as I could remember. 

Then I came back (having made sure my tummy and cunt were both semen-free zones. 

By this time, Chris’s own brain had woken up, formed some kind of wireless network link with mine, and they were handshaking (?is that the right expression? Computer geeks please correct me) like things possessed. 

‘Look - you shouldn’t be fucking around with boys yet 0 certainly not to the extent that you get spunk all over your tummy, AND you’re too grown up now to bounce stark naked into your own brother’s bedroom. 

I said “awww, you  don’t mind! Anyway, remember when we used to wrestle?” and so saying, I launched myself on him. Chris is way stronger than me even if we hadn’t been pretending, so him pinning me was easy, by now he was fully hard again, aand his cock was riding my clit nicely, a little wriggle and….

‘Ow!…Ohhh.” 

“Oh fuck…I’m sorry….I didn’t mean…I’ll take it out.”

“No! Wait a second….you’re hardly in anyway….just, be still for a second….there, that’s better….maybe…maybe if you push it in a bit further?”

“But you’re my sister.”

“Yeah, and you’re my brother…..so?”

He pushed a little and I cried as my imaginary hymen tore. This time he only paused for a second before pushing right up me. 

“Fuck, sis, your so fucking tight!”

“And you feel like a baby’s arm in there, you’re splitting me apart…but in a good way.”

i won’t bore you with the rest of it. Suffice it to say there was lots of re-establishing the brother/sister and underage spect of it before finally, I almost forced him to cum in me and, as I put it ‘…knock me up.” 

I’ve written about forbidden fruits before. Forbidden fruits in reality are different from forbidden fruits in fantasy land. 

When he’d gone and I was cleaning up, Miss Brain informed me that under no circumstances was I ever to bring ip the fact that he had thoroughly enjoyed me fucking him up the bum with him. Ever. “This is new and very uncertain ground for him. He has to process it, and even though he loved every second of his feminisation, and you fucking his bum, he may still end up filing it in the ‘never again’ drawer. Some guys are like that. 

This, I just don’t understand. With me, it’s “Never put off till tomorrow what you can do today, because if you do it today and like it, you can do it twice tomorrow.” I feel guilty about nothing I have ever done sexually, from my early attempts at masturbation, to popping my own cherry, to panty-peeing, to vaginal and anal sex, to oral (and swallowing) to lesbianism, to fucking my sister, and on one spontaneous spur of the moment thing, my dad. It all felt great, and no-one, not ‘society’, not anyone is going to give me a moment’s guilt about any of it. 

If I had been ready, I would definitely have fucked ‘illegally’-whatever that means. I know girls who fucked as young at 13. Good for them. They weren’t, as we seem to be told these days, ‘manipulated’ ‘coerced’ ‘groomed’., although I accept these things do happen, and the perpetrators of them need castrating, or in the case of female perpetrators *( and the simple fact that there are fewer female perpetrators does not, for one second, reduce the serious, appalling nature of their crime) well, sterilisation for them too. The girls I knew who had sex underage we’re totally in charge of their own bodies, and their own sexualities. 

In general - well, certainly among the girls I know well - girls seem to be far more honest with themselves about what they like, and what turns them on. Good for them! Boys have a macho stereotype that gets in the way of complete honesty. Chris likes…no, loves, his bum fingered and fucked….he apparently likes a bit of feminisation too, yet he only indicated either subliminally. It took Miss Brain to hook up on the signals. 

I knew boys who liked wearing their sister’s panties. Not because they liked their sister’s cunt stains between their legs. The two boys I knew who did this always ‘borrowed’ clean ones. They just like female things. Panties were all they could get away with in school, but one of those two boys I once gave a complete makeover too. I asked him what the best part was. I was expecting him to say trying on my school uniform, or one of my dresses, or maybe the makeup. But no. The best part for him was when I clipped a soft, cotton trainer bra around him and adjusted the straps to fit. 

Sex is wonderful - all aspects of it - all facets - all combinations - in all its sweaty, messy, smelly glory. 

Bring it on.