Our worst episodes don't look quite so bad anymore …
Teenagers are morons. Kids these days can ask the Internet anything and get the right answer, but many of us just had to wing it when it came to sex questions. What are some signs that a girl is into you? Where the hell is the clitoris? Can Icy-Hot be used as lube? In the pre-Google days, you were out of luck, and other than asking your older brother (who was a complete asshole), you had no options.
And that's why there's so much comedy in sexual regrets.
The embarrassment machine that is Reddit asked, "What's your biggest sexual regret?" and the Internet didn't disappoint.
Met a girl known as "Quickie Nicki"
She came over to "study"
I tutored the shit out of her…couldn't understand why she looked so disappointed. Finally after studying, I made my move, we kissed, but she was so tired from studying, she just wanted to go home. She told my friend she totally wanted to f&#^ me, but didn't know I was so into studying.
I'm not…I just…didn't…realize…until…FML
TL:DR No quickie from Nicki for me
Rubbing toothpaste on my penis when I was a kid. Thought I was going to die.
So for this story it's important to know that as a high school kid I was ridiculously awkward and shy. Complete and total cringe-level, but here goes.
In high school, about 16 years old or so, had just finished an extracurricular contest with group and we were eating out at Pizza Hut. Finished up and the teachers paid out. I opted to go get myself a refill of my drink before we left, and walked up and asked the girl working at the counter (about the same age as me) for one.
Her response: "So, like, can I get your number?"
Me: "Uhm…. I don't have a phone."
Her: "What about like, a house phone?"
Me: "….we don't have a phone at my house."
Her: "What about like, a friend's phone?"
Me(in FULL panic mode now): "I…..don't have any friends???"
I ran out the door in a panic, didn't even take my drink refill from the counter.
I was madly in love with a friend of mine. She had always known I had feelings for her and visa versa. But I never tried anything, because either she was seeing someone or I was. Bad timing. Then it happened, I was single for a while and she just got out of a relationship. Sooo we started hanging out. A lot. Then one day she asked if I wanted to stay the night.
I was so happy to be able to sleep next to her. I wasn't going to try anything because I wanted to respect her and not rush her into a relationship, but damn did I want to fuck her. So that night, we're talking the whole night. About anything and everything. It gets late and we're getting ready for bed. I had jeans and a T-shirt on and she had a tight tank top on and booty shorts.
So I crawl in bed and she says this, "jeans aren't allowed in my bed." And I'm confused. If they weren't allowed, then I'd have to take my pants off. I tell her this and she said she doesn't care. No jeans. So I take them off. And while i knew she liked me, i didn't think she wanted to fuck me. And I just went to bed.
The fuck, younger me, the fuck.. You oblivious idiot.
Sleeping with my ex after we broke up. Months of her stalking me ensues.
my biggest regret is also one of my proudest moments, she was smoking hot, we clicked emotionally, had a few drinks at a party. Kinda bumped into each other in the kitchen, started making out like teenagers. She suggested we sneak into a bedroom. I got some sense, mumbled some stupid excuse and joined the bro's at the bbq. Her husband was in the next room and her kid was at home with the babysitter. The regret is that I really had more than lust for that woman, the pride is that I did not fuck up her marriage. Someone else may have, but it was not me.
I had a friend about 20 years ago who told me that when he was 16 his dad remarried. His new step sister was the same age as him and their parents were so wrapped up in their own shit they basically neglected them for weeks on end. They ended up fooling around out of boredom, then having sex. They got caught and sent to all sorts of counseling. He said they were telling him he was a preditor and shit. He was like "Dude, she wasn't really related to me, it's such shit"
I tend to agree. Leaving 2 16yr olds alone, with no adult supervision, is a terrible idea. They are not really brother and sister, they have no natural instinct to avoid sex with each other. You should feel no shame.
A couple years back I discovered my girlfriend at the time was cheating on me. I confronted her, and we broke up, but it wrecked me. I was all over the place.
She convinced me to go over one night, and I was so depressed I just wanted to get back to normal, and stupidly thought somehow we could get back together.
Anyway, things escalated. Bad decisions were made, and we started having sex. The sex itself was pretty standard, considering the situation, until at one point, just as I was about to finish, I noticed several hickies/lovebites on her neck and shoulder that I hadn't given her.
That one really hurt. And took a while to get over.
(And for anyone wondering, yes I continued to fuck her, and because it was fueled by anger or whatever, it actually felt pretty great)
When I was in high school I lost my virginity to a guy that was attractive, charming, funny, and refused to touch me after we had sex. He would be so sweet and into me before the act and then immediately after it was like a switch would turn off. After he came, he would turn over, look at the clock, and ask me when im leaving. It left me feeling so unwanted and unattractive, but in a sick way it made me try that much harder to keep his attention. I learned how to negotiate "cuddle time" with him and he would time it. I could get 10 extra minutes in bed with him if I was lucky. He convinced me that all guys were like this and if they weren't, they were probably gay.
This was only one of many manipulative behaviors he had and it left a big dent in my self-esteem. We continued to have a 5 year relationship that consumed the best parts of my teen and college years. I was so naive and I spent way too much of my time picking myself apart because of him.
The first time I had sex with a new parter and they held me after, I burst into tears because I thought they were just being nice at first. Turns out men really want intimacy, too.
Banging my ex's mom. Said mom was single and had been drinking, and decided that this was her chance to be really horny and seduce me.
I had been drinking and i needed absolutely no encouragement to bang someone who looked like a clone of my then-girlfriend but with bigger tits.
The sex was fine, and my ex never figured out. It's just weird that her mom still texts me when she's lonely.
I lost my virginity to the same person that took my identical twin brother's virginity the evening before in Mexico at an all inclusive resort. I didn't know, and she tried to hook up with him again the next night, he turned her down, and she came after me. That was an awkward next morning. At least she has a crazy sex story to tell people… How many people can say that they took a pair of twins' virginities?
Back when I was about 16 I went over to this girl I was talking to's house late at night and snuck in and spent the night. Now, being that I was a private school raised, sheltered young man I didn't have the social maturity to know that if a girl invites you to spend the night and sneak in her house…then you should probably just go ahead and stick your hand down her pants…needless to say I did not. I snuck out at about 5 am before her mom got up for work and walked 6 miles back home down a busy freeway. Definitely my nastiest case of blue balls and one of my biggest regrets.
When I was 8 I put my dick into a soap bottle. Dear god I can still feel it burn sometimes (this is my most upvoted comment god damnit).