Anal Extravaganza!!!!!!

So, there’s a new boy – a 25yo I met through FetLife. He looks a bit like Ashton Kutcher, facially, and his body is…pleasingly beefy. He’s got a bit of extra weight on him, so he’s not cut to the point where hugging him is like hugging a pile of boulders – there’s a softness. But his biceps are so huge he has a hard time finding t-shirts that fit him. I mock him for this: “Awwww, the poor hot boy can’t fit into normal human clothes. Hot boy haz a sad.”

I’m always dubious when a young’un claims to be a masochist. I’ve had a lot of guys say they wanted to be hurt but then get spooked over the tiniest little thing, like when I pulled their hair as I kissed them. This guy, though – we’ll call him The Jock – has some experience in this area. He’s played before with another dominant (one about my age, actually) and he knows at least some of what he likes.

And even if he hadn’t had any experience, he has that quintessential thing that masochists have – he sees me and recognizes me. When I start feeling toppy and sadistic, I get a predatory expression on my face that scares most people. With him, my inner monster leaped into my eyes and (metaphorically speaking) he looked at it, smiled, and said “Oh hi.”

He knew my monster. He welcomed it. He watched it with joyful fascination to see what it would do next.

This is all just by way of introduction. The thing I want to tell you is that I fucked his ass with a dildo the last time he was over. He’s fairly stoic when I do really mean ouchy things, but my gentle-yet-firm assfucking had him howling. It was super fun and I’m eager to experiment some more. I forget whether he said he’d ever done any ass play before but my feeling is there can’t have been much – maybe just him, experimenting alone and unable to thrust too fast because the angle was awkward. When I fucked him, he had the look of someone who was treading fairly unfamiliar territory.

When his ass was worn out and he needed to stop, we had missionary PIV sex (our first time). Turns out he’s a jackhammerer from start to finish – straight-up using me to jerk off into – and he takes a while to come, so I don’t think I’ll bother with that again unless I’m trying to get off at the same time. For a minute while he fucked me he put his hand around my throat and applied a bit of pressure, which…didn’t make me panic per se, but made me wonder if I should panic. I never got any kind of scary violating vibe from him but why would he ever think I would like to be choked? I knocked his hand off me and he got the hint and didn’t try again.

Oh, just as an aside: he’s really good at reading and transmitting body language and this has been an absolute pleasure for me. I don’t mind being super blunt in my intentions or using my words to negotiate, but with him I don’t always have to. One time I had his hands anchored to the corners of my bed and I was just kind of exploring him – caressing, biting, hitting, just kinda scoping out my options. At one point I ran my nails lightly down his side, and, all within the span of like three seconds:

  • He yelped and flinched.
  • My eyes lit up because I’d found a thing that makes reactions, and I like reactions.
  • I tentatively poised myself to run my nails over him again.
  • He made a “NOPE SERIOUSLY DON’T” face.
  • I said “ticklish in a bad way?” just to make absolutely sure I understood, and he nodded so I moved on to other things.

This seems like such a basic level of communication but I feel like most guys would not have read my “OOOH FUN LET’S DO THAT SOME MORE” signals, or would not have made such an obvious “NOPE” expression in return. So often when a guy makes a sound or a flinchy motion I have to ask “good or bad?” – sometimes several times. It’s not the end of the world that I have to do that. Butthis was a refreshing change.

Anyway, after the PIV I had him help get me off by continuing to fuck me with my dildo while I Hitachi’d myself, as usual.

What I love is that he gets the whole thing where my arousal and sadism are linked together. After I came, he was still sitting between my legs. I was all ragey from coming and I sat up, said “I mean this with affection…” and just started punching him in the chest as hard as I could and snarling “motherfucker” and hitting him some more. He took it and liked it. And then he crawled up the bed and snuggled me and stroked my hair and we dozed off for a bit.

So that was fun.

But the thing I really want to tell you about is when Mine came over the other day.

Mine had been saving up his orgasms, edging every day but never coming, for two weeks. I hadn’t asked him to do that – not directly, anyway. I did tell him once in passing that I’d like to fuck his ass while he was really pent up from abstaining, and see if the desperation would help push him over into a prostate orgasm. I’ve always wanted to see a guy have an orgasm without anyone touching his cock (whether it was from prostate stuff or just a Jason-Biggs-in-American-Pie situation). It’s been a huge fantasy of mine since basically forever. And Mine is more responsive to ass play than almost anyone I’ve played with, so I figured if anyone could get there, it’s him.

I have a dildo that’s attached to a set of plastic “brass knuckles”; I bought it mostly because I loved the violent connotations but it’s also fantastically practical – way easier and more ergonomic than trying to hold the slippery base of a dildo in my hands and pump it in and out.

So I was moving this girthy, realistic dildo mounted on brass knuckles in and out of Mine, mixing up the speed and depth and seeing what worked. He loved it when I hammered him pretty fast and hard, but he kept asking for breaks. I’ve heard that guys will often get freaked out by the approach of a prostate orgasm (and/or think the building pressure means they have to pee, and therefore not want to release it) so after the third or so time that Mine said he needed a break, I asked him why he wanted to stop. Was it hurting, or just too intense? He said it was too intense. I was like “Well, as long as it’s not actually hurting, I mean…what do you think would happen if we just pushed through the intensity and out the other side?” He said he didn’t know but he was willing to try.

I started fucking him again with long, firm strokes – rhythmic and fairly fast but not jackhammering per se. This whole time, by the way, Mine’s hands were anchored to the bed; I knew how totally pent-up and desperate he was to come, and I wanted to torment him by making it so he couldn’t touch himself no matter how turned on he got.

My strokes with the dildo quickly brought him to the point of squirming and gasping again, and this time he didn’t tell me to stop. And then he cried out that he was going to come.

What happened next may be one of the most amazing moments of my sex life, ever. I maintained my thrusts at a steady speed – not wanting to change anything and maybe scare whatever was about to happen away – and Mine’s ass suddenly clenched harder than I thought possible, almost pushing me out. Then released. Then clenched again. Over and over, rhythmically. This was not something Mine was doing on purpose; this was his body taking over, and the contractions were so strong that I had to put my other hand on the brass knuckles, too, and use all the strength in both arms to keep the toy inside him. I surreptitiously watched Mine’s cock to see if anything was coming out. He howled and thrashed and clenched and howled some more (and nothing came out of his cock) and finally he sort of collapsed back into the mattress, sobbing in frustration, and told me he’d been right at the edge of a huge explosion but he’d lost it somehow. Watching him go through that had been so intense that I was feeling a little teary, too. Mine asked me to please free one of his hands from the restraints, and when I did, he put his arm around me and yanked me down into a hard one-armed hug.

I stayed lying on top of him like that and we talked about what had happened. He said he’d never felt anything like that before in his life. That it was definitely an impending orgasm, and would definitely have made him ejaculate had it gone to completion, and yet the sensations originated from an entirely different point than his usual orgasms. He thanked me for encouraging him to push past his fear of the intensity and keep going. He asked me what it was like from my side and I said I felt like a fisherman who had a huge blue marlin on the line and was trying desperately to reel it in. I sat up and briefly pantomimed fighting hard against a force of nature while panicking. Mine chuckled. He still seemed borderline tearful at having been so close to coming but not getting there. It was hot. He was really pent up.

Shortly after that I finally let him release all that tension. 😀

I definitely want to explore this some more. I’ve had times with other guys where they vocalized a bunch during ass play and maybe a bit of liquid dribbled out of their cocks and afterward it was like “I…don’t know what that was. Maybe an orgasm? Or an almost-orgasm?” but nothing – nothing – was ever as absolutely unmistakeable as what happened with Mine. There was no “maybe” about this. One day, I will take him all the way there. And then I’ll practice until I can get him there consistently. And then I’ll deliberately stop just short of the mark to make him cry. 😀




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2 responses to “Anal Extravaganza!!!!!!

  1. I really enjoyed this post. Having been on the receiving end of the orgasm Mine was about to have, I can tell you that it left me literally in tears of sexual bliss, confusion, wonderment and completely changed. It is indescribable and left me happily exhausted. My lover/wife/Domme and I both chase that experience and it has happened again but the first time was just such a miracle of the human mind and body for both of us that it must be like a junkie chasing their first and best high, we both want to have it happen over and over.

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