After we established via text that The Pedant shouldn’t come over tonight after all – but that he would make it up to me on Thursday night – he suddenly asked “what do you get out of penetrating someone anally?”

I often subconsciously picture myself as some huge predatory animal like a leopard or wolf, and that question made my imaginary animal ears prick up with great interest. I had asked The Pedant a few visits back if he would ever let me strap-on fuck him. I can’t specifically remember what he said but it amounted to “probably not.” Which is sort of odd to me because he’s let me put a finger or two inside him and seemed to enjoy it at least a little bit, and to my mind this is the same act but done in such a way that my hands are free. Maybe he doesn’t realize that dildos come in finger size and imagines that pegging automatically equates to being fucked by a dick-sized toy.

At any rate,  he hasn’t extended an explicit invite to his back door in quite some time and this made me wonder if those two or three times with my fingers satisfied whatever curiosity he had and he was done with it.

Yet here he was wanting to know what I might get out of it.

I said, “The pleasure/reactions it causes the other person, mostly. But I suppose there’s a role reversal element, too. Being penetrated is a whole hell of a lot more vulnerable than being the penetrator. I like when someone…um. Opens up to me. 😛

“I see.” Pause. “Are you willing to be gentle with me?”

“Of course. I take the trust involved very seriously.” …And then, wondering if he was trying to obliquely air an old grievance: “Have I been ungentle before?” I was very careful with him in my fingerbanging pursuits, but there’s always the possibility that his idea of “gentle” is different than mine.

“No, but gentle touches get me off harder, and I know you enjoy watching me come harder.” Pause. “Over the next few days, I’ll let you know how to seduce me into letting you penetrate me.”

Um, I have penetrated him. But I’m assuming he’s following up on our last conversation on the subject; I assume he’s talking about being pegged, not anal penetration in general. And the idea of being permitted to peg him is deeply, deeply hot to me. Especially needing to seduce him into it, actually. It arouses me fiercely to believe that The Pedant actually loves ass play but kind of won’t admit it to himself. It’s feasible; he seems pretty into being a manly manly man, and craving being penetrated is culturally coded as a chick thing. It definitely wouldn’t fit in with his idea of himself. And so maybe he can’t quite bring himself to be all “hey, strap on and gimme the D.” Maybe he needs the illusion that he’s reluctant and I’m persuading him. And, okay, if he ends up needing that pretense all the time it might not be hot anymore. But what I’m hoping is that this is just one more step in a journey and eventually he’ll be begging for my cock and moaning from the feel of it inside him just as flagrantly as he moans from the feel of his inside me. And I want to be the only one he’s so unabashedly vulnerable with.

Just as a recap of the journey so far: when The Pedant and I first started dating and the subject of anal play came up (long before we ever went to bed together), he said a woman had put her fingers inside him before and it had done nothing for him. I assumed the activity was off the table and didn’t bring it up again. Much later, when we were doing bedroom stuff, he was all “you can penetrate me if you want.” So I did, and he made turned-on noises during the act, but afterward he said he’d only suggested the ass play for my benefit. He suggested it “for my benefit” again a few months later, still without me ever having brought it up. And then I think maybe a third time. It seemed to arouse him every time, but he claimed that it didn’t. When I asked him what it felt like to him, he said “It just feels like pressure” which may be a face-value statement since I was quite literally putting pressure on his prostate – but in retrospect I wonder if he may in fact have meant the pressure of a prostate orgasm building up. Most guys can’t identify the approach of a whole new kind of orgasm or describe it in those words; how could they, when it’s never happened before? …More recently, The Pedant brought over a blindfold and some other sexual accoutrements for us – including disposable gloves and lube. And now he’s open to being pegged. For my benefit, I suppose.

I mean, who knows, maybe he is only engaging in that stuff to please me. That, too, is kind of a hot idea; The Pedant giving himself over to me purely because he knows I’d like it.

But it’s hotter to picture him coming his brains out while I thrust in and out of him.

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