Posted this elsewhere, but after doing all that typing, I wanted a backup somewhere.
The roughest was the first time with this particular guy, but we had been talking and texting daily for over a year, had met in person for dinner and to hang out for a day before, and were very, very comfortable with each other. We had also talked about limits, kinks, safewords, what was and wasn’t ok, etc at length. Although the uncertainty and “stranger factor” probably did help make it hot as well.
We met at a motel and I had made a point to dress up – short skirt, heels, stockings & garters with nothing underneath. He walked in, we hugged, we kissed, he grabbed me by the hair & put my on my knees. It quckly went from a blowjob into straight-up facefucking. I swallowed his cock down to his balls, so he pulled back out then slammed it it, while pushing my head down. He held me there for a while as and after he came, trying to make me gag (I wasn’t sure, but he told me later he wanted to see if he could make me puke on it). Then he had me strip and was calling me his dirty fucking whore and all sorts of things while I got naked and fingered myself for his amusement.