1. She’s never getting back those three seconds of her life.
“Awful, quick and embarrassing. She was sweet though but she’s never getting back those three seconds of her life.”
2. I farted in her face. Twice.
“I farted in her face. Twice. We’re getting married in 9 months.”
3. Scene looked like a time lapse of a wilting plant.
“I was too nervous and anxious to keep it hard long enough for insertion. Scene looked like a time lapse of a wilting plant. She was kind and patient, though. A few minutes later and some more heavy petting I was ready to disappoint her properly. And boy, did I!”
4. I got her pregnant. We were 14 years old.
“I got her pregnant. We were 14 years old.
I ended up talking her into an abortion. I didn’t find out until months later that it was twins.
I know we were kids but there is a lot I would do differently if I could go back.”
5. I lost my virginity to my first girlfriend in high school while we were listening to a Weird Al album.
“I lost my virginity to my first girlfriend in high school while we were listening to a Weird Al album.
The song that was playing at the point of insertion was ‘Germs.’
It was awkward and uncomfortable and made me associate Weird Al (goddamn Weird Al, of all things!) with sex for years after that.
I regularly regret past me’s decisions.”
6. Took a rubber glove, rubber-banded that thing on, and took her to pleasure town for about 3-5 minutes.
“I was 14 and she was 15. Had my house to ourselves. We’ve dated for about a year at this point and decided the timing was finally right. We had the movie, The Collector on TV. Things got heated as we were making out and she said she was ready to go all the way. Boy, was I excited. Only problem was I was terrified of going raw thinking I’d get her pregnant from pre-cum or not pulling out quick enough. I also had no protection and for some reason thought you had to be 18 to buy it. So I did what any 14 year old horny boy would do. Took a rubber glove, rubber-banded that thing on, and took her to pleasure town for about 3-5 minutes. Afterwards she cried because she thought her first time would be more special. Me being selfish never thought that hey, maybe taking a girl’s virginity with one of your mom’ s nurses latex gloves isn’t very romantic. It all worked out in the end, we continued dating for about and 2 1/2 years and got a hell of a lot better than our first. Friends love this story so figured I’d share…sincerely, The Rubber Band Man.”
7. I put it in her butt by accident.
“Backstory: Me, my best friend (we will call him Chris), and my at the time girlfriend where at his house watching movies since his parents didn’t give a fuck what they heard. Someone could be screaming bloody murder and they wouldn’t so much as flinch.
Story: My girlfriend and I were sitting on the couch next to Chris, watching the collector. 45 minutes into the movie she snuggles up to me. My 14 year old brain was like ‘fuck yeah hot bitch to my left and watching a movie could life get any better?’
After a while she started squirming and I thought she was uncomfortable, so I started massaging her back (who said chivalries dead), found put she wasn’t wearing a bra. So like the good fellow I was, I massaged her titlits.
Keep in mind it’s pitch black and Chris couldn’t see a thing. After 5 minutes of this I turned to Chris and asked him if he could leave the room for a couple of minutes, he kinda just looked at me and gave me the biggest shit eating grin two 14 year olds could give each other.
Long story short I put it in her butt by accident, she screamed and I jerked off when I got home.”
8. We didn’t have a condom so we used Saran Wrap…I’m not kidding.
“Oh, Jesus… Both myself and girl were first timers at 16 and 17. I was 17.
We didn’t have a condom so we used Saran Wrap…I’m not kidding.
That girl ended up stalking my future girlfriends for the next 3 years until she was put into an asylum (for unrelated reasons).”
9. Awkward but humorous.
“Awkward but humorous. Both of us were virgins so neither of us knew what we were doing. We just kind of decided to try a bunch of different positions since we were already fucking anyway so it was more of a ‘Let’s see what [blank] feels like’ type of thing. I (the guy) actually managed to last a whopping 10 minutes which is pretty long given I had never even had a first kiss up until two weeks prior to the pipe laying. It was all very light hearted and goofy. We didn’t take it seriously, neither of us tried to be sexy or passionate and we just had an awkwardly fun time all around.”
10. Nervous, unsure, quick.
“Nervous, unsure, quick, my parents were at a ball game and there was only 1 door between me and my gf of the time and my sister and her friend…it was not very romantic at all and I honestly kind of regret it but she kind of pressured me into it and for a 16yo boy having a girl with her legs open in front of you, well…When in Rome.”
11. First time was with my wife. That was 9 years ago. Still happily together.
“For me it was great, first time was with my wife. That was 9 years ago. Still happily together. Have a great son too. Was a huge turnaround from being a loser that sat in front of a PC playing WoW all day.”
12. I was repeatedly able to make her orgasm, but I couldn’t cum at all.
“Bizarre. You know how the stereotype is that the guy cums and then can’t make the girl orgasm next. Well the opposite happened. I was repeatedly able to make her orgasm, but I couldn’t cum at all. She called me back a few times after that and the same thing happened. And I had NO sexual experience. So I don’t really understand. I haven’t had sex since then. I’m unsure of what to think. At first I thought I was asexual, because I never felt any enjoyment. But that can’t be true, because I DO have a sexual drive. I’m afraid I’ll be like this with the next woman I’m with.
You could not imagine how awkward it is be in at the hour mark of your sex session, and she’s saying ‘I reaaaally want to make you cum. Cum for me.’ Meanwhile, your dick is going soft IN HER. Like. Fuck dude.
Also, I have NO idea as to how I was able to satisfy her. She texted me afterwards telling me how great it was. But like. I’ve never done it before. So there’s no reason I should have been that good. But she’s the one who always asked me to come back for more, even when I’d make excuses as to why I couldn’t come over.
TLDR: I fucked her so hard that I’M confused.”
13. Came three times in a 20-minute period. Didn’t know that was even possible.
“Came three times in a 20-minute period. Didn’t know that was even possible. First time: She was rubbing it and I came on my chest, embarrassing I know. 5 minutes later, second time: Giving me head, nutted while she was still sucking. The day I understood and lived that meme ‘When you nut and she keeps sucking.’ She came up after and said, ‘You taste yummy.’ I died a little. Also 5 minutes later, we had sex and I came inside her.
14. I was drunk, could barely keep it up, and couldn’t finish.
“I was drunk, could barely keep it up, and couldn’t finish. Pretty trash TBH. Was 19 at the time.”
15. I put a Trojan Ecstasy on inside-out. Dick went completely numb.
“I put a Trojan Ecstasy on inside-out. Dick went completely numb but I didn’t realize what I had done wrong. Was very rattled. I figured out what had happened, got a normal condom, and made it up to her.”
16. I lasted about a minute before I came.
“I lasted about a minute before I came. I felt bad, so I ate her out. 3/10.”
17. It took about three hours and we stayed up until 4AM, but it was absolutely amazing.
“It was amazing. We snuck away from our friends early like a couple of horny teenagers and took it back to my room. I was so nervous about it, but she helped me relax. She wasn’t a virgin so she knew what she was doing. I had no idea what I was doing because I am the biggest dork and low-key asexual. It took about three hours and we stayed up until 4AM, but it was absolutely amazing.”
18. Things got a little steamy until I literally slipped and fell down and hit my head while I was hard as a rock.
“We were both 18 and in her dorm. Her roommates were gone for the weekend so we were kicking it and having a grand old time. She had a shower fetish so she asked me to shower with her and I figured why not. Things got a little steamy until I literally slipped and fell down and hit my head while I was hard as a rock. Instead of asking if I was okay, she just hopped on and started riding me. Dazed sex was definitely an interesting experience that I did not enjoy. Would not recommend for first-timers. Did get better over time though so that was a plus.”
19. She was so tight she cried the whole time.
“Fucking awful. It was after prom, and she had grabbed those shitty small Durex condoms from the school health office. I wasn’t expecting for us to be finally killing our virgin status that night, or else I would have went and bought a box of good condoms. Couldn’t keep a hard-on the condom was so tight, and she was so tight she cried the whole time. 0/10 experience.”
20. I literally could not tell if I had penetrated.
More so in that I felt “’nothing.’ I believe she insisted on no-condom to try and alleviate that possibility but even “raw” I literally could not tell if I had penetrated. I kept mumbling “Maybe…Maybe I missed?” but she had all sorts of reaction faces so…I just…carried on until she was done and I was very…..very confused.
Second time with a condom (same lass) I think it strangulated me a little, looked like a choked mushroom down there but she shrugged her shoulders and said it looks okay to her. Felt something for like…half a movement….and then guilt-ridden repeat.
Now this only happened at 29. I’m 30 now. My “luck” with women is terribad, but I do legitimately fear something is derped down below and I’ll have to fake it in any future encounters. (My health is chronically bad in general but that area had always been the least problematic…err….on word of my hands at least >_>)
[EDIT] The consensus appears to be wank less. In my flacid defence….I WAS A 29 YEAR OLD VIRGIN.”
21. I had to nope out mere seconds after penetration due to my overwhelming apprehension of my own ejaculate.
“Horrible, I was 15 and it was with a girl I’ve come to realize is the closest we’ll probably get to Satan incarnate for a long time.
It was in the woods next to my middle school, with no condom. I had to nope out mere seconds after penetration due to my overwhelming apprehension of my own ejaculate.
I wish she just jacked me off to finish, but NO! Then a week later she blew me behind a store, less than 200 feet from my house.
She wouldn’t finish me, she made me finish me, and it sucked.
I wish it didn’t happen, as both times, my dick was better sucked by mosquitoes than her.”
22. She was pulling so hard I thought it was gonna rip.
“Mine was awful because she was pulling so hard I thought it was gonna rip. I wasn’t hard because of this and she just kind of shoved a semi in.
Not at all enjoyable. Be very careful who you choose to lose it to because I fully regret mine.”
23. I went down on her for like one second and it tasted terrible. Tasted like a mix of air freshener and some rotten nasty meat.
“Fucking gross…I was drunk on cheap champagne and my Dad’s GF at the time had this fat cousin who was hideous! I felt like I had to get it outta the way so I brought her upstairs to my room and she went to the bathroom and sprayed Febreze on herself. I could taste it. Omg and I went down on her for like one second and it tasted terrible. Tasted like a mix of air freshener and some rotten nasty meat. That taste still gives me nightmares. Her chin had a slight stubble and she had so much acne… Oh god and I finished on her stomach…ugh… I forgot her name but she’s married now.”
24. Worst 40 minutes of my life.
“It all started going downhill right after we removed our clothes and I blurted out I’m a virgin coz I was so nervous before we began. She laughed and thought I was gonna cum quick but lo and behold…
She gave me the hardest erection of my life through oral but then made me lose it during penetration because she kept making some really hard, concern-raising ‘umph’ noises, had a flushed face of clear discomfort and pain every time I thrusted and kept pushing me back so as to stop me from going too deep (I can only assume that 3rd part).
When she asked me why I lost it, I couldn’t bear to tell her that her body language was saying No despite her real desire to have sex so I just said I had exam stress.
Worst 40 minutes of my life.”
25. The most wonderful thing about it was having a girl like me so much she was willing to take part of me into her body.
“The actual sensations were lovely after years of jerking off. But the most wonderful thing about it was having a girl like me so much she was willing to take part of me into her body. I’ve since learned that it’s not really so deep as that with most women, but at the time it blew my mind. Years of insecurity just vanished in one ten-minute romp on a pile of laundry.”