1

I accidentally put myself in debt by f**king my former accountant on his desk and messing up papers. It got cleared up, but it was an awful week and a half. -RealNCRranger

2

Confessed feelings to my coworker. It went down so badly that I quit on the spot the next day. -FlyingFoxandwings

3

Let my (ex) boyfriend dry-hump me for an hour on a bench outside after summer school.

The bad news: this bench behind our school was also beside a swimming pool. Where parents were taking their children for swim lessons. Eventually a staff member came out and yelled at us for being inappropriate. -hannlouiseols

4

I got asked to dog sit at a friend's parents house. She set me up with a blow up mattress in the living room.

I got a little bored so I called my gf and we proceeded to have video sex right there in the living room. I got a text the next day saying there are cameras in the living room and they are just for keeping an eye on their dog while they're away but if I wanted to I can turn them the other way.

I was pretty embarrassed after that one. -fishthe9

5

Took an escort from a bar in Shanghai back to my hotel. Got carried away after she started give me a blowjob and lost all sense of rational thought. No condom. She hopped on top and we had sex, no condom. She stayed the night and we proceeded to repeat 5 or 6 times, and had zero protection.

Spent the next 3 months thinking about every tickle and twitch in my wiener convinced it was an STI.

Luckily, no positive results. 10 years later, and I think I’m clear. -ReedFreed

6

Said I love you to my ex after like 6 months of semi-casual dating lol. -loc_nessmonster0

7

Gave him gas money to come down and pipe. Safe to say I didn’t get my money’s worth. -Downtown-Ad5424

8

I dated a girl for about 8 months. Broke up with her. Saw her mom at the bar about 4 months later. She took me back to the same house "to hang out with the family". I should add, that the mom was single and attractive. Ex girlfriend (her daughter) was not home at 1am. So I hooked up with the mom. Next morning was a bit weird when my ex showed up at 10. -franzsuperman

9

Jerked off after cutting jalapenos. Halfway through I knew it wasn't going to end well and just didn't give a shit. -Redright888

10

Jerked off to my crush's house on Google maps. -Shadow_gentleman

11

Willingly watched The Notebook. -2leewhohot

12

Hooked up in a parking structure with a random guy in Vegas. -jazzy_girl8297

13

Got pregnant... Stupidly got super excited and told my husband to c*m inside me and Christmas Eve turned into a very expensive present 9 months later. -Defiant_Chapter_3299

14

Was trying to get with a girl in college. We were texting and I asked her what she was up to, she said she was training for a marathon and going to the gym and asked if I wanted to come. I ended up running 9 miles before I tagged out. So now I know how far I'd go to get laid, it's up to 9 miles. -euesquecimeunome

15

About ten years ago I had a double lap dance in the back room of a strip club. They made promises and I gave them my credit card.

Nothing happened except me trying in vein to fight a 4 figure credit card charge. I am not a smart man. -justbrowsing987654

16

Got a porn site membership and forgot about it. 4 months and like 150 dollars later I realized my f**k up. -lervington123

17

Thought that my bottle of hand sanitizer was my bottle of lube. -heavy__dirty__soul

18

I had a seizure and instead of calling a doctor afterwards I convinced my gf that I was fine and we had sex. -kilorevz

19

I did give my beloved childhood teddy bear a facial. When the post-nut clarity hit I just sat cross-legged on the floor looking at the hot mess of semen and fur I created. -NootNootMFer

20

The Uber driver asked me if I wanted to smoke some DMT and f**k her. Probably should have wrapped it up that time. -bluepillcarl