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This is the hottest and most memorable orgasm I've ever had.
It happened with a married Latina I hooked up with a few times, with her husband present. That of course is a whole story in itself, which I'll summarize as quickly as I can. I met this couple by responding to their Craigslist Casual Encounters posting. They were looking for a hung guy to have sex with the wife while the husband watched and took pics and video of the fun. It was their first time trying this. And after some back-and-forth, I was the guy who got this honor. No doubt I had a lot of competition.
You can see us in action in my latest pic, here.
Both the married couple and I wanted to play safe, naturally enough. Aside from the safety risk involved in going bareback with a stranger, there was the risk of pregnancy, since S. wasn't on any kind of birth control.
But when we first got into it for the first time, things got a little out of control. We got naked and were making out on my bed. S., while on top of me, started grinding - already risky behavior. But then she went further, grabbing my cock and rubbing it against her pussy. Well, at that point I lost all self control. Clearly, S. felt safe enough doing this (though, granted, she was a little drunk by this point). And I figured that there really wasn't much to worry about on my end, since from what those two had told me, neither of them had had sex with someone other than each other in years.
At any rate, overcome with lust, within seconds of S. rubbing the head of my cock against her pussy, I went for it: with a big thrust I plunged myself all the way inside her, and she gasped hard.
The deed having been done, I went for it. After stroking a bit from the bottom position, I flipped S. onto her back so that I was now on top (without ever pulling out from her), causing the husband to hornily murmur "Fuck". And I proceeded to fuck her savagely. I was barebacking this hot woman I had just met hard, while her husband was right there watching it happen, and the whole thing just blew my mind in the best way.
My flipping S. over had landed her pretty close to the edge of my bed, and my heavily pounding into her got her ever closer to the edge. I felt an orgasm coming on, and decided to give in to it rather than trying to prolong the action. But I did have the presence of mind to know that I couldn't come in S., that I'd have to pull out. And so I did, right at the critical moment. And my doing so pushed S. the final bit over the edge of the bed: as I got ready to cum she slid down to the floor, softly borne on a wave of blankets, her eyes locked with mine all the while.
And I came. Hard. It didn't seem right to facialize S., so I aimed for her tits. I've always been a pretty big cummer, and for whatever reason it was an especially big load even for me that I shot forth now. Several big spurts streaked S.'s tits, neck, and shoulders. The husband said "that's a lot of cum!" a nice confirmation that this was indeed a good load. S. didn't say anything: she just kept her eyes on mine throughout the cumshot, and only once I was fully done did she break eye contact to see the mess I had made on her.
The whole thing was hot for everyone involved - I would dare say hotter than what any of us had expected from the experience. At the same time, we were all worried about the risk we had just exposed ourselves to. In the next few days we got tested for STD's and showed the results to each other, confirming that there was nothing to worry about. We went on to have two more similar hookups, though we (mostly) stuck to safe sex from then on, confirmed cleanness notwithstanding.
The husband has sent me various photos and videos that he took of these hookups. And they're good, but none are as hot or as vivid as the images burned in my brain of that one orgasm, the hottest I've ever had.