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About a year ago I confessed in another sub to being a hopelessly horny old goat, constantly masturbating thinking about my adventures from my younger days and wishing I could have some new ones. Here I am, once again too horny to sleep, reading reddit late into the night, and I find this sub. I like to give a bit back to subs I've enjoyed when I can, so here's a story from my (somewhat) younger days...
This happened a bit over ten years ago, when I was around 40 and craigslist personals were still a thing. I'd posted an ad as an older man looking for a young woman who wanted to have some fun and got a rare reply from an actual person. She was 19 and lived a bit out of my area, perhaps a forty minute drive, and she mentioned I'd have to be very quiet because she was still living with her family while she attended the local community college.
Contrary to the impression you sometimes get reading places like this sub, there don't seem to be all that many young women interested in much older men, so of course I agreed to drive down to meet her after exchanging a few emails. We didn't exchange phone numbers, just using craigslist's anonymous email thing, so it wasn't until I parked in front of the house across the street and pulled out my phone to send her a message telling her I was there that I saw she'd sent me a couple of messages while I'd been on the road, saying she'd heard someone walking around the house and maybe this wasn't a good time.
But I was already there so I sent the message anyway, not knowing whether she'd even respond. Fortunately she did, said it was now all quiet, and she'd come open the door for me. When she did I found she was a cute, somewhat curvy Latina with short hair. We snuck quietly through the living room and down the hall to her room, where we exchanged a bit of awkward, whispered small talk, the only part of which I remember is that she said she was on the pill and didn't want me to use a condom. Sometimes being the male version of a stupid slut, that was fine with me. Eventually I asked if she wanted to proceed and she said yes.
I kissed her, undressed her, and explored her young body with both my hands and my mouth, eventually burying my head between her legs until she came as she held her comforter pressed to her face to try to stay quiet. She returned the oral favor a bit before we moved on to the main event and I fucked her in a variety of positions for perhaps half an hour before finally filling her up while she rode me.
After a few minutes catching our breath she said she was getting tired, so I got dressed and she put on a robe and snuck me back out the front door. I wished her goodnight, and we never spoke again.
I still think of that night occasionally, and wish that craigslist was still around and that I might find another young woman who likes older men, and who might invite me to come sneak into her bedroom and have my way with her in the middle of the night.
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- 3 years ago
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