Got a few awkward ones from when i was younger. these ones are mostly just embarrassing on my end but i'll share them anyway
story 1:
in high school i was at a party one time and i started hooking up with this one chick who was basically known to be sketchy and slutty and i almost had sex with her but at the last second she was like 'sorry i don't sleep with people on the first date'. probably was on her period but was too embarrassed to say. the next morning when i had sobered up i was like thank god for that because she was sketchy. anyways a couple of weeks later she messaged me and was like 'hey you should come over today' and i was like 'oh yeah maybe' and then she said 'i want to have sex with you' and i was like 'hmm okay. well i dont know if i want to have sex but i'll come over anyway'. my mind was saying no but my dick was saying yes. i went over there and we put some stupid fucking movie on, i can't remember exactly what it was but i feel like it was monsters inc or something, like a kid's movie. we just laid on her bed, not even touching. i didn't make a move, i just went there and watched that dumb movie and then when it was over i was like 'alright well i'm going home now' and she was understandably just super cold and was like 'okay seeya'. didn't talk to her again. she ended up with like two kids by the time she was 19, don't know where she is now.
story 2:
so i had been fooling around with this other sorta sketch chick and we had made out a few times while hanging out but never taken it further. there was a lot of sexual tension so i picked her up in my car and then we went to a secluded spot and started making out. i was fingering her and actually did that long enough to make her come. then she was like 'it's your turn now' and she started rubbing my dick through my shorts and i basically just came straight away, like literally after seconds of her rubbing my dick through my shorts. i must have had some strange look on my face because she was like 'um... are you okay?' and i was like 'yeah... sorry i think we should stop now' and she was like 'wtf?' i was too embarrassed to tell her i had just came in my shorts and she hadn't even realised. we get back into the front seats of the car and it's super awkward. then in my post-nut depression i started to feel ashamed and i was like 'i don't think we should hang out anymore' and she started to cry. i dropped her off home and she would message me like weekly on social media for years afterward and i would just ignore it, i eventually just blocked her.
story 3:
when i was a bit older i lived in this sharehouse for a few years and i was the only dude living with 3 other chicks. i'd just broken up with my gf of 2 years and was getting a little bit unhinged without regular sex.
so first i started trying to hit on this one chick in the house who was probably the cutest one, but unfortunately had a bf. we would sit on the couch together and basically play footsies while we watched tv and just being touchy in general. a lot of sexual tension was building and we got super close to fucking but i think she realised i had broken up with my gf and it was like knowing that turned her off, like she originally thought we would both be cheating so it was okay or something and once she realised i was actually single she started to feel guilty? i didn't push it and let it go.
so i started to flirt with another girl in the house. this one was a fairly heavy girl and less attractive than the first but actually had a super cool personality and we got along pretty well. so one night we went to a party, had a few drinks and the party was lame so we went back to our place together and kept drinking in her room. one thing led to another and we were making out, then the lights went out and clothes came off. we got to the point where we were about to have sex and she was like 'do me from behind' so she turned over and as she got into the position on her knees with her ass pointed up at me i just got this overwhelming whiff of shit and it was over for me, my dick went limp. i didn't want to embarrass her so i was like 'ah fuck sorry... i just got nervous' and she started blowing me and it was just kinda pathetic because i couldn't get hard again. after that night it was awkward whenever we saw each other, i tried to be cool but she was hot and cold. we didn't get sexual again but there was one awkward time when she basically asked me to be her boyfriend and i was like 'nah' and she started crying in the kitchen and that other girl walked by. i guess the girls got to talkin' and then they all collectively decided i was a scumbag (which i probably deserved) and the rest of my time in that sharehouse was pretty shit, none of them talked to me. months later, on my last night there that girl messaged me at like 12am asking me 'are you still up?' i didn't respond then the next morning she awkwardly apologized for 'being a creep'.
after i moved out we still talked on messenger a bit and on new years eve she came to the same party i was at (obviously just to see me because she didn't know anyone else there) and i was hanging with her and her friend a bit. we were having a little bit of banter and at some point she said 'you couldn't even get it up to fuck me' and her friend started laughing super hard and i just smiled and bit my tongue. she was too naive and i was too nice to even respond to that. she followed me around for a while that night but i got super drunk and went on an adventure and ghosted her. after that we never spoke again.
i'm glad all those years are behind me now. makes me cringe to think about how awkward i was.
Topic: Awkward Sexual Experiences (Read 463618 times)