I [M] lost my virginity to an older woman I met off Craigslist.

This happened when I was 22. When the casual encounters page could still be found on craigslist. I’m now 28. I had been trying for a couple months, to find a woman who would like be my first fuck. A few close calls, but everything kept falling through. Until one day in October. I get an email, from somebody who is interested. She’s 38 years old(let’s call her Rachel), from my home town, and is turned on by the thought of taking the virginity of a much younger man. We exchange numbers pretty quickly. We’re talking through text while trimming weed. She sends me some nudes of herself. I am instantly turned on. She is incredibly hot, a milf to die for. I told her I was turned on, and my cock was now hard. She asks to see! I of course, happily oblige. Take two pictures of my cock , and send them to her. (I am working, but I’m alone in a shack, on somebody’s property, with 2-3 pounds of weed on the table in front of me.) She is impressed by my size, and how nice my cock looked. It doesn’t take long for her to ask to meet me later that night. I was in shock, I was about to be laid for for the first time. We agree on a time I’d pick her up.

Fast forward to that night.
I pick Rachel up in my car, and drive to spot she knows of that’s off in the woods. Rachel is about 4’10, 38 years old, petite, perfectly stacked boobs, 3X ddd’s, tattoos on a third of her body. We make small chit chat, see what I wanted, agreed no condoms. She had her tubes tied, and we’re both free of disease.
We begin to make out in the car, I start fondling her beautiful breasts (as any horny young guy would) as she starts massaging my cock through my pants as it’s growing in size. Takes it out of my pants and is gently stroking it for a couple minutes. All the clothes eventually come off, and I’m climbing into the passeger seat of my tiny car. I take a moment and admire this naked woman about to sit on my cock and ride me to orgasmia. She starts to lower herself, and guiding the shaft with one hand into her very wet and warm pussy. I’m in the pleasure zone now boys. Everything was just amazing, sucking on her titties, the hickies on my neck. Rachel is riding my cock for 10 minutes or so before I finally cum inside of her. Giving her a nice cream pie. We just sit there for a couple minutes, breathing heavy, and kissing. My cock is just pulsing inside of Rachel at this point.

We then get out of the car and walk around a bit in this open space, that’s in the forest. Cool October air, almost a full moon out as well. Go back over to the car and just cuddle while leaning against it. I was ready to go again after a little bit, but she had to get back home. So we got dressed and cleaned up. Drove her back to the place she was staying at, talked about meeting up again at some point. Made out with some tongue, said goodbye.

I wish there was a part two to this story. But there’s not. We never did hook up again after this. I’ve since this time have moved away from my hometown, live halfway across the country now. Me and Rachel are friends on Facebook now. Have spoken never spoken about this night to each other.
But I still think about Rachel sometimes when I jack off.

Tldr; An older woman from the Casual Encounters section of Craigslist, asked to see Dick Pics. She proceeded to take my virginity.

Source: reddit.com/r/gonewildstories/comments/dgl1kq/i_m_lost_my_virginity_to_an_older_woman_i_met_off