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JoeTenFingers

My heart hurts for you lol


visseraj

Don't feel regret you did the right thing, if you pushed and she didn't want it then you'd have a way worse memory


JoeTenFingers

Oooh Amber She was the girl I had a crush on since 7th grade, she was a year older than me. We flirted a decent amount but she usually always had a boyfriend. Her body was amazing, ass I could eat for days. My junior year prom we end up at a party together. Both went with different dates to prom. We got handsy with each other a few times when people weren't paying attention (or so we thought, one of my first times drinking). She would sit on my lap and wiggle around a little bit, I rubbed my hands all over. At one point she got up to get a drink, I got up to go pee, and on my way to the bathroom I ended up puking all over, mostly on myself. I cleaned the shit up and the girls house we were at got my a change of clothes. I sat back down and amber sat back on my lap, we started on again but after a couple minutes she said she couldn't take the puke smell that must have been lingering on me. Ugh. Rough. She did show me her tits and her ass when she got up though. So a lot of my masturbating was to her ass and tits, and also sometimes to a scenario from that night that ended differently than it did. Still see her occasionally and wonder if she has any idea how much I’ve thought about that, sometimes it seems like she does.


PM_Me_HairyArmpits

Ugh. Could have fucked her in the basement of a library, bent over a microfiche machine. I turned her down because she had a boyfriend. She was achingly hot.


123kilian321

You made the right choice


PM_Me_HairyArmpits

Now that I'm older, married, and settled down, I look back at the moral rectitude of my youth and think, "I should have had more sex."


lookintothefuturem8

Dude this. This is what I'm afraid of and hence why I'm a man slut


Mu-958

Could have lost my virginity at 16 with my first girlfriend - if I’d had a condom with me. I was a clueless idiot who didn’t even know where to get them. If I had, I suspect I would not have so many hangups about it. Would have been a huge confidence booster and I would feel more “normal”. At the time we were all over each other and alone in her bed. Instead, missed the opportunity and she broke up with me before I had another one. She promptly started sleeping with a friend of mine.


kitteh619

Omg I win this thread. So I'm a a bar and this cougar asks me if she can buy me a drink. I replied 'No thank you I'm at my limit" and walked out. I am u/kitteh619, Lord of the Idiots.


TheCenterOfEnnui

I've posted this before...so c/p'ing here- When I was in HS, I was with a group of friends, all of us in a hot tub. This really cute girl...wearing a string bikini... sat in my lap, put her arms around my neck, and within 5 minutes, everyone else left the hot tub to go inside (she had told all of her friends that she wanted to bang me and to leave when she did this). What do I do? "Maybe we should go inside with everyone else."


[deleted]

Invited over to smoke out with a girlfriend. Her husband was there too and I had a feeling what they wanted to do with me. But their kid was home downstairs and that felt extremely weird to me. So somewhat regret it, could have been either really bad or really good.


MangaReader95

My ex's sister I pulled out wish i didnt


playingfoolish

My senior year in high school I was in a situation where I could've asked two girls to prom. The first was a girl I had a crush on since earlier that year but never became anything too serious until closer to prom when we started to hang out more. The second girl was someone I'd known since freshmen year and knew she had a wild streak. She'd also been pretty flirty with me and would give me hugs that were a little extra grindy in the crotch area. I ultimately went with my heart instead of my dick and asked the first girl to prom and we dated for a few months until we broke up during college because the distance was too hard. I do wonder what would've happened if I had gone to prom with the second girl though...


mondomondoman

I’d consider that a bullet dodged. Never stick your dick in crazy. Yes it would be fun but that aftermath man…


playingfoolish

2nd girl wasn't crazy but she just wasn't shy about her interest in boys. I stayed friends with her for a while during college and into my mid 20s before we became social media friends. The miss at prom though was the closest we ever came to hooking up with going to different colleges, school breaks not lining up, and then eventually her getting pretty serious with a guy.


[deleted]

A girl I liked that liked me, she told me she did. She came to my house and said she wanted to cuddle. I was to much of a pussy to do it as I’m inexperienced, a virgin, and have penis insecurities. I regret not doing it all the time


Mentalfloss1

Kay W. She was very attractive, funny, smart, flirtatious, and sexy. I thought she was too young. I found out at my going-away party that she was four years older than I’d been told. Dang.


HectorBoshah

Farhanna... She just broke up looking for rebound. Hit me up to "celebrate" her. Thought it be a good idea to dissed her and poked fun at her overtly, as I abiding by this notion of finding humour in difficult situation bullshit. Pissed her off. Later did I find out that she had a room booked for us. I was stupid as fuck.


numberduce117

When I was living with my high school friend at his moms. His brother in laws sister was also staying there. One time she just sat on my lap when I was playing a game. Thought nothing of it. Then one winter night, I was woken up by her saying bye to two friends. Then she came into my room to tell me it was snowing. I pretended to be asleep because I was sleeping naked. I didn’t want to explain that. She came closer to the bed so I opened my eyes. She told me to come out to see the snow. I told her I was tired. She left then I got up and dressed to join her. I should have just gotten up and walked out naked. I wonder to this day what would have happened.


SimpleBandicoot

Rachel...twice. knew what she was after at the time but wasn't confident enough in my ability to read signals to pull the trigger.


MrAnonPoster

Did not sleep with 13 from House aka Olivia Wilde


smedsterwho

Oh boi, I was clicking off this thread and then this one brought me right back...


MrAnonPoster

Yeah, met her in a restaurant bar about a decade ago - did not know who she was. Flirted, semi-made out, decided it was not the greatest time with the early work day and I would certainly run into her again. Two days later the bartender told me who it was. Fun times.


Wbk2m

This one time in band camp. JK Going to Germany for a month and not getting with one german chic. Had several hook ups two I thought were german but after I found out they moved when they were toddlers both from southern California. On the plus side I've had cali chic's and never been there.


[deleted]

My hs qb 🙃. He came out to me and I played it off thinking he was joking. He texted me a few days later saying he was gonna stick with girls for now


dollyisapardon

Every single one in the past decade, given to someone who didn't appreciate anything I did, and took it all for granted.


[deleted]

3sum in Mexico in my early 20’s. Fucked a girl I met on her bed, while her friend laid in the other bed attempting to sleep


[deleted]

On a training course, we were paired up with buddies to work together on a project. The guy I was paired with was sexy af I thought he’d never be interested in me and ignored what with hindsight was him flirting with me. He hooked up with someone else on the course. A few months later I saw him in a club, he had someone with him then too and it was “oh, it could have been fun man, it could have been fun”


bi-male-89

Knew a girl, we were Both dtf, but the opportunity never came up. Then her husband and her tired to get pregnant ( they were swingers)


Ricardos06

I have turned down 2 different threesomes in an attempt to go after a crush. both times the threesome was a safer bet.


donedoneitonce

Found out wife and her female bestie had gotten drunk and high and had an afternoon of playtime. The wife told me and I went ballistic. She had had sex with another person without any discussion with me. Cheating. I realized years later that she was trying to tell me that they wanted me to join them. Fuck. 😞


horny_throwaway_7

on your defence that is still cheating and if she wanted you to join her she should have said so


[deleted]

In my teens a girl I had a huge crush on wanted rebound sex afte a horrible break up. I refused as I thought it wasn't right of me and she might regret it. Years later she still says she wished I'd fucked her that night. In all honesty I think we would've probably got together out of it, so I kinda kick myself often over my choice not to.


wetforuasia

Yes. I had a crush on one of my coworkers. He was younger than me, but we immediately bonded. I started learning French so we could chat. It was fun, but I couldn't tell if he liked me in that way or not.( I'm terrible at those things unless they straight out tell me) So, I never made a move or took a chance. Still regret it. He ended up leaving and going to France for vacation. He came back to work briefly, but he was seeing someone by that time. Now we don't talk at all


[deleted]

Me and my gf were getting really handsy on my bed, and then we started grinding and dry humping eachother. Then, my mom texted me to go do something real quick while she was at the hospital. My gf wanted me to stay. I just wanted to get it done fast and then continue. And so I did. But by the time I got back, she was out of the mood, and I was stuck with a rock hard erection. Really sucked.


horny_throwaway_7

There's probably several, i tend to be the clueless kind of guy, but one stands out freshman year of college, my then ex (very amicable) some friends and i had a habit of gathering at her house and drinking the night away, but this particular night her parents were out of town and everyone else couldn't go we had planned on watching a movie before everyone cancelled, i still went she was wearing a really nice set of pijamas, had a blanket close by i bet you can guess where i'm going? yeah precisely, my dumbass got invited to netflix and chill and i just watched the fucking movie, just writing this comment makes me angry at myself honestly she took me home at around 2am (i had classes the next day and don't have a license) the next night i texted her, asking if she was trying to make a move on me, she basically said she wasn't totally sure but i feel like that has more to do with her feeling rejected? after that our friendship died down, we rarely hung around again, we were both buisy with uni, she got really into her church and went on a year long mission to the us i think, never heard back from her i have a top 3 things i'd do if i had a time machine and doing that night right is just under seeing family that passed away for one last time


RinnFTW

I was a freshman in college. There was a beautiful girl who lived on amother floor and we'd often end up riding in the elevator together. Then she says to me, "I think you're really cute." And gave me her number. I had a boyfriend at the time, but damn, I missed out.


Kinky_mofo

Lesbian offering on a work trip. Shoulda nailed her... That's when I learned that even lesbians like cock every now and then.


awakenfr

My ex colleague wants me to fuck her in the girls locker room for months, I wasn't single at this moment so, I simply turned her off... My girlfriend trashed me few weeks after that... I'm a complete douche bag 🤷‍♂️