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.
