So. I attached The Pedant’s wrists and ankles to the corners of my bedframe and we kept on making out. He was still not fully hard (oh hey – that’s probably why he gave me “my turn” first – whenever he has erectile difficulties he deflects by focusing on me so ferociously that I hopefully don’t notice. But I do notice…).
And, y’know, I don’t especially care that The Pedant sometimes has an uncooperative penis. I’m good with just touching him and making him moan without any big end-goal in mind. But I think he feels like the end goal is supposed to be his orgasm, whether he actually wants one or not, and he’ll never admit that it’s not gonna happen; he’ll never give me explicit permission to, like, kiss and touch him for as long as it’s still fun for me, and then we can just go watch NetFlix or something. So I end up flogging away at him for hours until I’m actually sort of bored. But if he really is desperate to come and just having difficulties, I don’t wanna be all “bored now” and stop; that would be rude.
Anyway, as I set out to see how much I could make The Pedant swoon and whether I could get him hard, I remembered that he used to like his taint pressed on, back in the day. So I started doing that, and it got an even stronger reception than I’d remembered. And, interestingly, his responses seemed to raise in pitch and urgency the further back my fingers went, so that I ended up rubbing my lubed fingers right up against his asshole for quite some time.
Then I think he got hard enough that I could ride him, so I put a condom on him and did that for a little while (fully expecting that he wouldn’t come; this was me getting the stimulation I wanted). His erection faltered soon after though so I dismounted and went back to teh making out/nipple play/asshole-rubbing.
After a while I said “Tell me what you want” both because I was at a loss (he was clearly really enjoying what I was doing, but it wasn’t going anywhere and I was beginning to feel trapped in limbo) and because I just flat-out like hearing him articulate his desires.
The Pedant did his usual (and hot) thing of taking a few moments to be able to form words; he gets really immersed in physical sensations. Once he’d surfaced, he murmured “I want you to penetrate me.”
When The Pedant and I first talked about anal penetration, he said he’d tried it before and it did nothing for him, so I didn’t push the issue (although I secretly wondered if his previous partner(s) just didn’t do it right…like just stuck a finger straight in without targeting the prostate, for instance). Then one time in bed he asked for it, which startled and aroused me to no end, but afterward the consensus was “Nope, sorry, it was worth a shot but I’m still not into it.” And I really thought that was that. But now here we were again.
And so I ended up kneeling between The Pedant’s spread, cuffed legs, sliding one gloved/lubed finger into him (my god he was so tight…more so than I’d remembered) and jerking him off. For, like, ever. At one point he actually asked me to go deeper inside him, which was such a turn-on OMG. I got him right on the verge of coming several different times (and god, the way he squeezed my finger when he was close to the edge…) but he never quite went over. I think he asked me to go deeper still but I was already pushed into him so hard that I was basically taint-punching him with the rest of my knuckles, so there was no “deeper” to go. I did however tell him I had a toy he might enjoy (the Njoy Pure Wand, which The Bunny also enjoys taking far more deeply than my fingers can reach). He said he was open to that.
So I went and washed the Pure Wand, and ran it under warm water for a bit to heat it up (it’s made of stainless steel and would feel quite alarmingly cold on someone’s innards otherwise). And then I returned to the bedroom, lubed it and slid it fully halfway into The Pedant’s tight little ass – maybe more. I find it slightly awkward to wield the wand because it’s curved; I have to keep remembering that the part that’s inside my partner is at a steeper upward angle than the part I’m holding in my hand, and compensate accordingly. There was an adjustment period as the two of us figured out how I needed to hold the thing and whether I should wiggle it, thrust it, or not move it at all. But then the handjob resumed and once again he was right…at…the…edge. Moaning desperately and bucking his hips and sort of fitfully pulling against the restraints.
But I couldn’t get him over the edge, and then he needed a bathroom break so I withdrew and unclipped the cuffs from their moorings.
When he came back to bed, we snuggled up and I think even dozed off for a bit. Somewhere in there I said “So, when you said you never really enjoyed penetration before, could it have been because nobody went deep enough?”
The Pedant shook his head. “It’s about exploring it with the right person. I trust you.”
“I’m glad,” I said, trying to camouflage the slight shake in my voice. Few things make my heart beat faster than when a partner trusts me enough to be vulnerable with me, physically or emotionally.
“You were totally planning all of this when you initiated getting together with me, weren’t you?
“You initiated this get-together,” I reminded him.
“Oh. Right. Hey, you never told me the story of the sex club.”
So I told him the story and we had yet another annoying conversation where I was like “I’m not sure how bi I really am because vulvas freak me out” and he dismissed me and insisted that vulvas are awesome and I pointedly said “So are dicks” and he acted like his aversion to cocks made more sense than my aversion to vulvas because reasons.
This somehow led to me asking him if he’d ever suck a silicone dick (I forget how that happened but I’d wager The Pedant said cocks are gross because they’re attached to dudes, so I decided to play devil’s advocate and talk about lady-dicks). The Pedant deflected by saying “I’m not sure what the point would be.”
“The point is that the sight of a guy sucking my cock turns me on enormously. Also, I do have double-ended dildos where a little push/pull suction would have a direct visceral effect on me…”
“Ah,” The Pedant said. “Well in that case I can kind of understand it.” This, I think, is a sign of progress…I’ve joked around in the past about him sucking my cock and he was always just flat out NO NOT EVER NO NO NO EW. It seems like maaaaaybe he’s coming around.
I have to admit that I love the idea of…not exactly breaking a guy, and not pressuring him to do anything he doesn’t want to do, but like…bringing him around to the point where he’ll do things with me that he never thought he’d do. Maybe helping him discover that he had a submissive little bitch inside him the whole time. The Pedant comes off as brash and kind of an asshole most of the time, and when we first started sleeping together he was very much trying to be the take-charge stud – now I can make him go ecstatically nonverbal with just a touch, we spend most of sexytimes with him tied down and helpless, and he’s apparently started liking anal. Hawt.