I suspect the dude from the other night wishes I would put his penis in my vagina. Last few times we were scheduling a session and I asked what sorts of things he’d like to do, he told me he wanted me to “have my way with him.” Nothing more specific than that, and when I gave him a hand job like usual he seemed vaguely disappointed, so I’m guessing intercourse was what he was trying to hint at. I wish he’d just say that’s what he wants. TBH I might be willing to do that – for more money. His dick is big enough that the $100 he pays me for an hour just isn’t gonna cut it. But I’m also happy enough with how things are that if he’s not hinting at intercourse, I don’t necessarily wanna put it on the table.

The other night I brought lube and nitrile gloves with me and asked him (after some foot worship and wrestling around on the floor) if he might like to try some ass play. He kind of didn’t even seem to know why a guy would want to do that – like obviously he knows that anal sex on a guy is A Thing but maybe he didn’t know that the prostate is up in there and that it’s basically the dude g-spot.

I was honest with him – I said that it’s not guaranteed to be the best thing ever. I said that in my experience, some guys love prostate play, some find the sensation kind of confusing the first time because it’s so new but they end up asking for more and loving it, and some just end up feeling “meh.” He said he was willing to try.

I’m pretty sure he falls into the middle camp. While I had my finger inside him he kept saying “that feels weird” – but while I palpated his prostate, I used my free hand on his dick and he came faster and shot further than usual – an astounding roostertail of jism that arced right over his head and hit the wall.

He’d hosted for a change, and as he drove me home he still periodically said “that felt so weird” in a contemplative tone. I’m not gonna push him to try it again, but I have a feeling he’ll ask. 😀

Also, I’ve found a bunch of erogenous zones on this guy that drive him absolutely crazy to a point where he seems almost afraid of the feelings he’s experiencing and tries to block me or flinch away (I always check in with him at that point and he says what I’m doing does feel good). I love when I can get a guy to that state. If there had been a good way of securing him spread-eagled so I could force him to take what I dished out and see how loudly I could make him scream, I would have. But we weren’t on my home turf.

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