That second bout of sex with The Pedant, btw, consisted of me attaching his left wrist and both ankles to the bedframe and then making him edge while I fingerbanged his ass.
The last time I made him touch himself for me, he lightly drew his foreskin up and down using only his fingertips; I assumed this was his habitual style. This time he left his foreskin pulled back and did the traditional fist-and-lube thing so now I feel like I’ve been picturing his masturbatory habits all wrong. You know, during the five hundred times I’ve gotten myself off to the idea of him getting himself off (wankception!).
I feel like such a creepy asshole saying this but for realz, The Pedant’s words contradict his actions all the damn time so I feel free to second-guess his stated wants. Like, he’s said once or twice that he doesn’t like me moving my finger inside him, he just likes me to press his prostate and hold still. But when I did move my finger, he would usually moan (and I am keenly attuned to his sounds and can tell a happy moan from an ouchy one). So this time around I experimented some more to figure out what he actually likes. I think when he told me not to move he meant that he wasn’t a big fan of the particular move I was doing at the time, which was thrusting in and out. A very tiny wiggle-motion of just my fingertip seemed to turn his crank, as did swirling my finger around like I was scraping frosting off the inside of a bowl.
And so I sat between his knees with my index finger buried to the hilt, moving around in different ways to see what got the best reaction. And The Pedant slowly stroked his cock until his body began to tense and his ass clenched around my finger and then his hand went still and I instinctively stilled mine, too. I’ve gotten very, very good at reading his body, so I managed to precisely ride the line of tormenting him without quite making him come. I knew just when to start moving again, when to back off. After a while The Pedant resumed jerking off for a few minutes, then stopped again; again I backed off for one long, breathless moment and then resumed stimulating him just enough to keep him squirming and moaning but without triggering an orgasm. It was sometime during one of these silent, breathless, don’t-move-or-he’ll-come interludes that I looked down at his gorgeous, sprawled, helpless body and flushed face and got all overwhelmed by the idea that he was giving himself to me. And jerking off in front of me, too, which I think probably embarrasses him a little bit and which I was worried he’d refuse to do. The feels overwhelmed me to a point where I thought I might burst into tears. I clenched my jaw and stifled it. I also really, really wanted to express my love and lust for The Pedant via beating him, but that is not a thing he would enjoy so I stifled that, too.
He resumed stroking himself for the third time, and after a few minutes I said, in conversational tones, “I figure after you get to the edge a few times I’ll put that stainless steel toy in your ass and then fuck you to the finish.”
The Pedant murmured something I didn’t catch. I asked him to repeat it. It was “I’ve been at the edge for a while now.” …Ah. That would explain the increasingly erratic quality of his stroking; he was so close that he had to take frequent mini-breaks to maintain things.
“Shall I retrieve the toy, then?” I asked.
I slowly, gently began to pull out of him, but he clenched reflexively and he’s crazy tight to begin with so I couldn’t move – at least, not without hurting him. I laughed lightly and said “You have to let me go…” I waited for him to relax a bit, started pulling out again, and once again he slammed shut on my finger to a point where I figured I’d better hold still. “Jeez, you’re like one of those Chinese finger traps.”
Only the very last segment of my finger remained inside him. I twitched it, just kind of to be silly, and to my surprise he gasped like crazy. I wasn’t even anywhere near his prostate; my fingertip was wedged squarely within the ring of muscle at his entrance. His hand slid back around his cock and pumped it a few times; then he removed it again. I continued wiggling my fingertip and he said “You’re gonna make me come if you keep doing that.” …Wow. This boy once told me that ass play did nothing for him and now he was on the verge of coming just from the very tip of my finger penetrating him, without either of us touching his penis at all. SO. FUCKING. HOT.
In retrospect I kind of wish I’d pursued that path – kept wiggling my finger and seen what happened. Would he indeed have come just from that? Would he have grabbed his cock again at the last minute to stroke through the orgasm, or would he have kept his hands at his sides and just spurted helplessly into thin air?
But ever since we started barebacking I can hardly bear to let him orgasm anywhere but inside me. It just makes me feel so close to him. I think he must feel the same way because the few times that I have tried to give him a hand job to completion, he’s almost always asked to be inside me in the end.
So I finally pulled out of him the rest of the way and replaced my finger with a warmed up and lubed stainless steel butt plug. Then I rode The Pedant to orgasm. He wasn’t as expressive as he usually is but it still seemed like a good one. Afterward, I undid the restraints and lay next to him and he promptly curled up with his head on my chest. It suddenly occurred to me that I think he usually adopts that position after PIV, as opposed to spooning me etc. I could be wrong about that. But maybe – just maybe – that specific configuration feels submissive to him and/or serves as aftercare. It’s an interesting thought.
On a whole other note, later that visit I asked him if he’s ever gotten off to a picture of me (I’ve text him some provocative shots before and never did know if they succeeded at arousing him). “Oh, yeah,” The Pedant said, instantly. “Not while staring right at the picture, or anything. Sometimes I need to use both hands. But yeah.”
I am mightily intrigued by the fact that he uses both hands sometimes when jerking off. I’d been curious for a long while as to whether he touches his own nipples during the act (the thought of him doing this turns me on, like, a lot) but it seemed like the kind of thing that would embarrass him if I asked directly. Now I think I have my answer. Or maybe he’s cupping his balls with his other hand or playing with his ass or who the hell knows. Pretty much the idea of him getting both hands involved is crazy arousing to me, regardless of what he’s doing.