[MF] When I was a twinky 20-something fresh out of college, I lost my anal virginity to a woman twice my age whom I barely knew.

When I was in my early 20s, fresh out of college, I was a skinny nerd who spent too much time on the internet and was exploring the world of fetish and BDSM. I wasn’t a virgin, but my real world sexual experiences to that point had been pretty lackluster for all involved!

I got chatting to a woman on a BDSM personals site who was about twice my age (guessing early-to-mid-40s). She seemed to get a kick out of how young and “innocent” I was. I was pretty good at flirting online in those days, and so I did a good job of pushing her buttons and getting her all riled up.

One night, after we’d both had some wine and were chatting away, she gave me her address and invited me over. I hurried over there as fast as my excited little feet would carry me. Part of me was worried that this was some kind of elaborate catfish and I was about to be mugged, but since I was in my early 20s, horniness overrode any sense of caution!