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!

I found my way to her apartment door and knocked hesitantly. She opened the door and pulled me inside. She was red haired and heavyset — I don’t mean fat, but sturdy and strong — smoking a cigarette and wearing a leopard print nightgown. She looked me up and down and laughed at how skinny and frail I was compared to her, calling me a “wuss.” She ordered me to strip down, then pulled a pink lace teddy over my head, plopped a curly blonde wig onto my short boyish hair, and led me into the bedroom.

There wasn’t a lot of discussion. No talk of safe words or limits or anything like that. She tied my wrists to the headboard and proceeded to subject me to an hour of cock and ball torture: tying my shaft up with twine, slapping it around, squeezing the balls until they felt like they would explode, grinding my cockhead into the rough bedsheets…. The only things she would say would be to gruffly snap “Shut up!” if I cried out too loudly, or purr “Good girl!” if I accepted the pain without complaint.

Eventually, when I was a broken down mess, she unbound my hands and announced that one of two things was happening next. “You’re fucking me or I’m fucking you. Choose.” You can probably guess what my answer was. I asked her, very politely, “You fuck me, please?”

She laughed and called me a “wuss” again, and then rummaged in a dresser drawer until she produced a ribbed blue dildo and harness. She handed me a bottle of lube while she strapped it into place, then lay back on the bed and told me to lube her up. I ran my shaking hands all over that big wobbly cock, lightheaded with the knowledge that it was about to take my anal virginity.

When it was suitably greased up, I mounted her reverse cowgirl style, and slid my asscheeks down onto her thighs. I distinctly remember moaning with delight as I felt her slick cock sliding inside of me. It was at this point that I realized there was a mirror on the dresser opposite the foot of her bed, and so as I bounced up and down on her thick cock, feeling the rubber ribs rolling across my sphincter, hearing her laugh loudly at my excitement, I got to watch the whole thing happening to me in real time.

We played together a few more times before going our separate ways. It’s been ten years and that night is still one of the most intense sexual experiences of my life. In a lot of ways I’m still chasing the high that I felt that night. Thank you for reading!