BendingOverForNote: I am reposting this with the editing I should have done better at the first time.
Put an ad on Craigslist and had a guy message me, he told me he was black and asked, "will that be a problem" and I said no, no problem, thinking to myself that's a bonus. He came to my motel room and after a little chit chat, he pulled his pants off laid on the down on the bed and I started sucking him. He had a nice cock about 8” and thick and I managed to get almost all of it down my throat as I bobbed up and down on it he started moaning, so not wanting him to shoot a load in my mouth I stopped blowing him and went into the bathroom and retrieved the complimentary hand lotion, lubed him up, climbed on top and slowly lowered myself on his cock. I moved up and down on his cock for a bit and then, I thought, well, it would be better if I get on my hands and knees and let him fuck me from behind. (passive position) But it didn't go well, for some reason it felt very painful as he entered me, and I tried to squirm away, but he wasn't hearing it, he grabbed me by my hips and just pushed it in. It became bearable after a few, I don't remember how long he fucked me, 2 minutes, 10? But I told him again that it was hurting, he said "hold on I'm almost there" and then he buried himself in me and shot his load. I quickly scooted forward on the bed and his cock popped out, and as it did I felt something warm on my thigh and thought, great I just made a mess. But, turned out it was just his cum that shot out of me. First and only time I had cum squirt out of me. Phew.
In hindsight, that was a good fuck and I have masturbated remembering it.