Died my hair black. My roommate was doing it and the girl helping him was redonkulously hot. She came into the living room and told me, "We have some extra dye, I think you would look hot with black hair."I looked at her in that lime green tube top and said, "That sounds like a GREAT idea!" I found out I was allergic to hair dye when, 3 days later, my head swelled up and I looked like that orc general that attacked Minas Tririth in Return of the King with a full head of Elvis-black hair. It took a whole month of medication for it to go away as my head was bright red under the hair and secreting a fluid that made my hair hard as a rock. u/berkeleyjake

In my senior year of high school, I was supposed to take AP tests all day. It would've looked good for college. Well, all the other grades had the day off, and my boyfriend was a year younger, thus being a grade below me. He picked me up to take me to "school", and since his mom worked all day, we went right to his house since we couldn't do mine because my parents worked from home. It went great until his mom came home to check on him. So he basically shoved me into his closet. It wouldn't have been a problem except it wasn't even like a full closet. It was half the size of standard closets. She left and then decided to come back and bring him lunch. I was in that closet for over 2 hours, and my phone was at 10% when i first crawled in there. I ended up just sitting in the dark for about 45 minutes of it. u/The_Real_LadyMacbeth

Connected with a friend's ex who I knew had feelings for me. Went to "catch up" over lunch, ended up spending all day drinking with her, then fingered her at the outdoor area of an absolutely packed bar. Neither of us were staying in places we could have people spend the night, so hired a late Hotel room ($$$). Get in the door, she immediately vomits all over the room and spent the next 2 hours crying on the floor saying she loved me while I did my best to clean up. u/chvch-nz

Paid for a porn subscription that I didn’t realize I was still paying for until 1.5 years later. $1135 for one orgasm. u/BusinessFamous1237

I alllllmost jerked off while driving down the highway once, but then I thought if they found my mangled corpse in the wreck with my hand around my dick, my family would be really disappointed. So my brain won that battle. u/Beginning-Bed9364

when i was a kid my dad would frequently take me to his job and give me meaningless tasks to “help him out.” he was a property manager for a secure gov building, federal guards at the doors etc. anyways he had his office in the basement and was left alone down there by everyone else in the building, he would smoke cigarettes down there, blast music etc. when i was 13 i went with him to work one day and he gave me the job of using an electric sander to take grime off of copper pipes in one the machine rooms. i was left alone to my task for hours and about an hour in i realized how incredibly powerful the vibration was on the sander. one thing led to another and i ended up grinding the handle of the sander on my dick. after i finished i remember even at 13 saying to myself “you’re really weird dude.” never told anyone, till now. u/No-Tailor5120

Jerked off in principal's office to his daughter's picture. u/SuvenPan

Decided to masturbate into a urinal because I was bored and horny studying for finals when I was in college. I studied in an empty classroom in the creepiest old building on campus so that I could be completely focused and not be distracted. I hadn't seen anybody in that building for 3 hours so I didn't feel the need to lock the bathroom door or do my business in a stall like a normal person. So I'm going to town on myself and suddenly the bathroom door opens and I stop mid-fap (foreskin noises stops suddenly). I just stood there holding my erect penis for a second, put it back in and leave without making eye contact. Still have no idea who that person was, but they definitely knew what I was doing and that I'm fucking weird. u/PMME_ur_lovely_boobs

I was helping my dad close up the sailboat for the winter. We took the seat cushions out and the long one's had to go in the car between us, kind of stacked up like a wall so we could only see each others heads. Teenage hormones kicked in on the hour ride home and I proceeded to rub one out while looking out the window. Many moons later I told my brothers who then proceeded to tell my dad. "I always wondered why you were so quiet on that trip" u/Hantsypantsy

Jerked off at the top of a mountain, looking over my city, as doing something "forbidden" was a interesting idea. Well the view was amazing, but I was scared to get caught. Looking back, if someone would caught me, i had serious issues now. u/TheLegende11

Paid $1200 for a private room at hustler in Vegas, threw the strippers a wild card and said… y’all sit down while I strip for you…. Wtf was I thinkin u/Novel-Persimmon7752

Girl offered to jerk me off if I let her copy my answers off of one of our finals. I thought it was going to be sometime after, but nope, it was right there during a lecture. Being a typical young guy of course I wasn’t gonna reject the offer. Still surprised to this day we weren’t caught. u/Scarface397

Bailed a chick out of jail once. $200. She then got so drunk she peed on my couch and tried to bang my mom. Took her shopping and just left her there. Never talked to her again. u/colcunnilingus

When I was in the 8th grade my teacher was a MILF. It was during English, while everyone was working on their essays I was busy rubbing one out under the table. Finished in my boxers, then the post nut clarity kicked in and I realized I had to wear those boxers all day. u/Bloodhound2910

Paid $2 for a massage app on my xbox that was supposed to make my controller vibrate. It didn’t do anything for me and I forgot to refund it so now I just have this random ass massage game in my library. u/spxdergirl