I did it once with this couple I used to fuck with, late 50's, both kinda bear type.
I had just started PREP so it was among my first times getting fucked bareback (my first time with them anyways), and I'd told them that trying DP was something I wanted to do since I always heard condoms could so we hadn't done it before
They'd both already fucked me for a while that evening so I was pretty stretched out but it still took forever to get them both in there, I took way too much poppers, and once they were in they really kinda just stayed there not moving much because it would hurt too much otherwise but it was still so fucking hot man
just the whole process of being between the two of them, feeling both their cocks prodding at my hole, one would fuck me for a bit, then the other, then you try again, and each time you're thinking that this is the time when they're both going in, but one of them slips out so you try again, etc. Them kissing me, encouraging me and also telling me dirty things, etc. They used to make me call "daddy" and "uncle", too, which I absolutely loved
It's honestly one of the hottest experiences I ever had but I don't know how much I'd want to repeat it. the feeling of having two dicks in you, in itself, wasn't amazing, it feels like when you first have anal and anything you put in feels huge and kinda painful. I'm not interested in fisting or anything like that and focusing too much on "i have to stretch out my asshole" would make it too weird for me I think
But it was incredible mentally, the building, not knowing what to expect, the whole "oh shit i'm really doing this" aspect of it and just feeling so slutty.
