Who was the most unexpected person you ended up doing the dirty with?

Who was the most unexpected person you ended up doing the dirty with?

What do you think?

12 Points
Upvote Downvote

31 Comments

Leave a Reply
  1. The girl I lived next to when I was born.

    She moved when I was eight years old.

    I moved from the UK to Australia three years later.

    About fifteen years after that, we were both backpacking in The Philippines at the same time, so we decided to catch-up. And yeah.

  2. I’m gonna go with my now-ex-husband. He was from a vastly different culture and income bracket. When we met he was a rich Asian trust fund kid partying it up while in school, I was a divorced addict with no education who had grown up in a fundamentalist family and had only recently figured out he was gay. On paper we shouldn’t have worked. In practice we honestly didn’t work either, but damn if we didn’t give it a try

  3. A customer when I worked for a supermarket.

    I used to work the same shifts each week and had regular customers, with the regulars we got on really well and had a laugh. I was 19/20 at the time and she was in her 50s. It was near Christmas and I had served her just before my break. I went outside for a smoke and she was waiting for a taxi, we had a chat and she leaned in for a kiss. We swapped numbers and she invited me round. We ended up having sex, was unexpected looking back at it. At that point she was older than my parents

  4. Probably a girl I started going to middle school with in 1990. She was our prom queen. I saw her for the first time in seventeen years in 2014 and we were doing it probably less than a half hour after I walked through her door.

  5. A school mascot. I was just there to listen some guy talk, but … one thing leads to another thing and next thing you know, you’re in a car park gangbang.

  6. My friends elder sister who is 5 years elder to me.
    We were at a party where both my friend and her sister was present. She was going through a breakup. We were all drunk and at one time i was consoling her and we hugged the next thing i knew we were making out and we had sex on the terrace. My friend still doesn’t know about it and i have not talked to her sister after that night. Things became wierd.
    She was cute with a nice rack i still wish if i can fuck her again.
    I was 21 she was 26.

  7. my coworker from when I was in high school we never rlly talked or anything while we worked together other than about work and even then it was short but About a year after I quit we matched on a dating app and a year after that we got married

  8. One of my coworkers in buttfuck Nowhere, Alaska. I worked as a QA in a cannery and she was the quiet, weird girl. One day I noticed she was coming on to me and didn’t think much of it…except after working weeks without being able to touch my dick (we all slept in bunks with room mates), sleeping on 3-4 hours a night, and working around 90% men, I was going insane. The opportunity presented itself and next thing I know we are banging on the top of a stack of palettes and letting all that pepped up horniness out. Was fun, but I felt bad as she seemed to be wanting more than a fling.

  9. My sister in laws cousins daughter, who was my age. I lived with my brother and his wife, we went on a weekend vacation, met her relations by chance, me and the daughter talked, exchanged numbers, and both snuck out at night to fool around. She later said she felt bad about it and that it felt “almost incestuous”. I’d bet it had more to do with religious guilt, because it’d be hard for us to be any less related with how far that connection was.

  10. An old high school friend. I wasnt in the friend zone or anything there just wanst anything there as friends. Years after we graduate i see she put up a photo of herself on a quary shirtless faceing away from the camra flashing the highway. Nothing but flip flots and a bikini bottom. Kinda turned me on and messaged her asking why. She replied free the nipple. Having not seen an old friend we got lunch and caught up i drop her off we have a cigarette together and are talking. Next thing you know i made a comment about her photo saying something along the lines of “you know i only saw the back. How come the people on the highway got to see your chest and not me lol” just looking to see some boobs. We where on her padio so she makes sure nobody is looking or home yet. Pulls her shirt up and shows me. For a good minute. Out of nowhere i pinch one just because. Kinda see where it goes at this point. She bites her lip and i put my face in her chest. From there we go inside and i spend the afternoon with her catching up. At no point was i expecting to get laid but at the time she was better than most others i had been with. Nor did she we wanted to catch up with an old friend. She even said she will show them off cause its her body but when i grabbed it she just wanted to be touched more after. We fooled around for a few months never dated both wherent into one another romanticly only lust. In the event we are both single we still will meet from time ti time but respect one anothers relationships when in one.

  11. My friend’s cousin. I thought she was a lesbian. Her girlfriend was passed out on the floor next to us. I guess I was the only other option to get off? She had a wide vagina.

  12. The girl at sunglasses hut in the airport we did it in the storage room I slept like a baby on the flight hopefully there was no cameras in there lol

  13. My friends younger sister. We were both in our early twenties, bored and lonely, living out in the middle of nowhere. The relationship sputtered out pretty quickly, I think we both just needed the connection for a little bit.

Leave a Reply