Jumping In The Deep End

31 July 2008 | 2 Comments

About a week ago this guy contacts me – young, mid-20s, cute in a boy-next-door sorta way. He says he saw me on XTube and then the blog and it’s his fantasy to suck and get fucked by a guy with a Price Albert, but he says he’s only been fucked once before and he’s probably pretty tight…

I was game, but pretty busy with work, so wasn’t until tonight that we could hookup. He seemed nervous and tentative. He was still online asking questions when he should have left – was wondering if it was OK with me if he had a little dick, and was wondering if he was loose enough – said he couldn’t get his butt plug all the way up his ass… But eventually I got him to come over…

He arrives and he’s cute – cuter than his pic… He wanted to use the bathroom – no problem… When he came out he didn’t seem to know what came next. We kissed a bit. I felt his chest and realized he had pierced nipples… Off came his shirt and I played with his nipple rings and we kissed some more.

For someone who said he wanted to suck a pierced dick he wasn’t exactly getting down on his knees very quickly… My pants were off, my dick was totally hard and throbbing. We got his pants off and I realized he had a pierced dick as well – only not a PA – a frenum instead. And he wasn’t kidding about his dick being little. My thumb was possibly bigger than his hard dick… But I like that – a lot, so no problem there…

Eventually I got him sucking my dick after warning him about how it would hurt if the ring hit his teeth. He gave it a shot, but as I found when I sucked a guy with a pierced dick – the reality isn’t the fantasy… I’ve only met a few guys who could really deal with sucking my dick when it had the ring in it and they’re usually top notch cocksuckers with tons of experience.

So I took out the ring and let him continue to suck my dick. Since he had said he had only been fucked once, and it was obvious he was never going to be a top, I figured he must be an oral bottom. But I started wondering about that too… It wasn’t a bad blowjob, it just wasn’t the blowjob you’d get from a serious oral bottom…

What I really wanted to do was fuck him. I had him sniffing poppers while he sucked my dick, and so I had him do some more poppers and then went to fuck him… Well, he wasn’t all that tight (thanks to the poppers and him stretching his ass before he came over), but he definitely wasn’t used to getting fucked either. He was really sensitive…

It took a while for him to get used to my dick. And even then I couldn’t tell how much I could do. I found that when I pushed in deep he had a real problem taking me. So I stayed pretty shallow, but that was hard to do ’cause I had him legs up with me over him and it was so easy to go in deep – and it felt so good. It was sorta fun to watch him squirm, but at the same time I didn’t want to do anything that would make him insist on stopping…

In the middle of fucking he sorta fessed up that this was the second time he’d ever had sex (not just anal – but any sex)… He’d been pretty conservative in the past and was breaking out of his shell. I came from a similar background and understood where he was coming from. When you’re repressed everything is a fantasy and those of us who start repressed tend to let it all go and be pretty uninhibited. It didn’t surprise me that he’d gone out and gotten his dick and nipples pierced. And it was almost funny that he comes out sexually by getting me, of all people, to fuck him… He wasn’t wading in the kiddie pool – he was jumping into the deep end… Getting a rough fuck by a top with a pierced dick and getting bred.

Since he seemed pretty loose I asked if he wanted me to fuck him with the PA and he said yes… So I put it back in and then shove the ring up his ass. We had been using a lot of lube and it went up pretty easy. Once it was in, I went to work and just used his hole and fucked him pretty rough. It actually wasn’t all that rough, but for him it was rough… And he seemed to be loving it – it was what he wanted. Then I moved around a bit and was fucking him not so deep so the ring would go in and out of his ass a bit.

At about this point he started hurting. I pulled out a bit and noticed some shit, but not much, so I shoved back in, but he really was hurting, and when I pulled out again he noticed the shit… I went into the bathroom, took out the ring and washed off my dick.

When I went back into the bedroom he was sorta embarrassed – he didn’t realize that this was sorta par for the course when you fuck with a PA – it goes in places a dick doesn’t usually go. I’ve had my PA come out covered in shit before – he just had a little bit…

So I went back to fucking him, but he was really distracted by the shit and kept saying “oh shit” (ironically enough)… His head just wasn’t into getting fucked and I think my semi-rough fucking roughed him up a bit and he was genuinely sore. He was grinning and bearing it, but it was painful for him and he couldn’t get past the pain.

Finally he said he had to stop. Bummer. I tried to keep it going, but it just wasn’t going to happen… We laid and talked for a bit. I played with his tiny dick, his pierced nipples, of course his hole…

His hole was actually pretty excellent. Since he had been stretching it, it was pretty loose – it was a genuine hole and so incredibly fuckable… Of course, I got hard again and wanted to fuck. I got on top of him and took his arms and held them above his head. He had this huge grin on his face and then it struck me what he wanted… He wanted to be force fucked – raped… I mean his whole face lit up when I was restraining him…

My dick was hard and right at his ass, so I got up, put a little lube on it and shoved back in and then went back to holding his hands up above his head. I could tell it hurt him (though I think it was mostly a mind thing), but he was enduring it and sorta enjoying it. Then I shoved in deeper and at that point he couldn’t take it.

Damn, I really just wanted to fuck him hard and breed him, but he just couldn’t take it…

Finally things sorta wrapped up… Hopefully he’ll come back for more – so I can finish off what I started…