31 People On Their Biggest Sex Regrets

X Redditors Divulge Their Most Shameful Sexploits. Found on r/AskReddit.

1. snackburros

I only tell this story online, but I fucked some Harvard Square pit rat crustpunk train-hopping chick in the bathroom of Great Scott (I think?) in Allston, Mass. Boston Redditors will know how dirty this is. Also I caught chlamydia from it.

2. QueueHead

I had sex with a friend’s mother several times when I was very young. She was and still is married to my friends father. I’m not going to tell anyone about that.

3. genericblackmale

A watermelon that I microwaved when I was a teenager. It was a beautiful night.

4. philuhbuster

It was during my junior year at a Big Ten school. I was in the residence halls with a friend who was an RA, in the building with all the athletes. I met one of the first year football players. (We met at a residence hall event), we started talking and he jokingly said something like, “Dude you’re kind of cool for a gay guy.” This seemed a little off kilter for me, so I decided to just run with it instead of challenging it, I made some joke and he laughed. We hit it off so well that we started hanging out a few times with my friend and some of his residents whenever I visited. Then he asked me to come play super smash brothers with him (for Nintendo 64, obviously). Eventually push came to shove and we ended up fooling around. He is still in the closet and I think still on the team. I am not a fan of outing people, so I wouldn’t tell anyone. Sadly we never talked again, he hit it and quit it.

5. butthole_balls

Nobody. I’ve had sex with nobody, and my friends have no idea. They all think I’ve probably been around, and get laid a fair amount. Nope. Not even once.

6. Jabberminor

Not quite sex, but a handjob from a 33-year-old goth lady who had an 8 year old son that slept in the same bed as her. Also, she was married, but was getting a divorce.

How did we connect? We both really like Guinness.

7. dirtydruggiealt

Not intercourse, but I let a chubby guy who was 15 years my senior suck my dick and lick my asshole in exchange for crystal meth. I’m straight.

8. ceilingkat

I slept with my best friend’s ex-boyfriend less than a week after they broke up. He was my friend for 4 years and I met her through him. While they were together I got an earful about how good he was in bed. She wasn’t lying. It never went anywhere, we all graduated. She still doesn’t know.

9. JimmyGrimble11

I had sex with my ex-girlfriend’s sister the week before we got engaged. My ex was 19 and her sister was 16. I was 19. Found out that I was taking her virginity shortly after it started.

10. daaaabear

I had sex with this ketamine/crack dealer who was a complete whore. I didn’t realize how bad she was until I saw her doing a foil of crack right in front of me. That was a mistake.

11. sleptwithbestfriend

Mindy the prostitute in an Amsterdam Brothel.


Bill Murray, because who would believe me?

13. Taco_bowl

Well, I suck at life, but I had sex with my best friend’s boyfriend. I worked with my best friend and was just going to keep it quiet, but it ended up happening a few times more and I got pregnant. Clearly, we no longer speak and I’m raising a baby with a man I knew less than three months. Make smart decisions, kids.

13. YourWebcamIsOn

My wife, hii-yo!

14. Ghotiyz

I fucked my sister’s best friend on my sisters birthday whilst my sister was passed out drunk.

15. SanchoSailor

I was living with my girlfriend and her childhood best friend and her boyfriend. Her boyfriend and my girlfriend worked really shitty night shifts and we were left spending a lot of time together. For 3 months nothing happened between us. One night she just started showing up in my bed. We were having sex 2-3 times a week on average for about a year. Neither of our SO suspected anything and we never told. I broke up with the girl after we all moved out to do our own things and they are still best friends.

16. thisnameisawful

A really fat hooker with a name that wouldn’t, over the phone, lead one to believe that its owner was almost 300 pounds. But I was deploying in two days, so it didn’t matter.

17. ron2838

Met a older woman online, had drinks, asked me to fuck her in the ass, I did, then left and never saw her again. A year later found a girl, fell in love. Together for almost a year and go to meet her parents after we get engaged. Her mom and I recognize each other right away and we get the deer in the headlights look, we never spoke of it. Her husband and my wife will never know.

18. DrumCorpsAlum

I left my virginity in the back end of a fat girl in New Jersey.

19. Thestreak03

Back when I was into drugs I had a few sexual encounters I wasn’t too proud of. This one takes the cake though. I went over to my ex gf’s house to smoke with her and her lesbian gf. We got tweeked out and decided to do some naked hot tubbing. I don’t know what it is but there is something about meth that makes me insanely horny and being with two very attractive women in the tub got me going and I got a hard on. My ex’s gf said she wanted to watch me fuck her gf and I happily obliged. Halfway through the lesbian said that she would let me fuck her, she had never been with a man before, if I let her put a dildo in my ass. It took me about 5 seconds to say sure why not and ended up having one of the best threesomes of my life. My friends do know about it, I’m very open and not ashamed of my past.

20. SleepingGiant70

I once tried my left hand.

21. RatemyCock_

I got drunk and had sex with my uncle (not blood related) I am a male and not gay.

22. throwawaycreeper4551

19-year-old high school student. I am 36. She says she likes me because I’m “not creepy.” She’s the first girl to be really into me in a decade. I’d say “don’t judge me,” but you should. I’m certainly judging myself. Hard.


The chocolate donut from when I was 15. My parents were out and I was desperate. Ended up with a dick smelling like chocolate, so no regrets.

24. juic3box

I had sex with a pregnant girl who basically begged for it. She said, and I quote, “Best part about being pregnant is you can’t get pregnant!” So basically she rode me to the DVD menu of Alice In Wonderland (the original version) on loop. Strange music and quite awkward. Yeah. Her and I don’t talk.

25. UrNameXIV

I drunk fucked my step-sister, twice.

26. de4thpowers

I banged my middle and high school bullies girlfriend on their anniversary. He was varsity quarterback, she was a head cheerleader. Absolutely zero regrets. Also, put it in her butt.

27. yosoju

That guy from Craiglist…oh man.

28. smellslikepuke

My best friend’s girlfriend. Not to avoid fights and hurt feelings, but because it was actually his idea, and he stayed in the room and watched me fuck her. It would just be a weird story to tell people…

29. datbiiitch

Hopefully this will stay buried. I had sex with my best friend’s brother. Who is now in prison for multiple counts of sexual assault on a child. -_-

30. dseif19

My ex-girlfriend, again.

31. poncho_goblin

I had sex with a mentally disabled woman on her period. It was a weak time for me as a person. Thank god for condoms. Thought Catalog Logo Mark

Like this, read this: I Probably Shouldn’t Have Done That.


More From Thought Catalog