19 Men And Women Confess To The One NSFL Sexual Encounter They 100% Regret


1. Just Skip This One If you don’t have a strong stomach

I dated a girl that didn’t really know much about…well anything, really, but more so her own lady parts. About 2 months into our relationship, sex started to become difficult. It wasn’t that the chemistry between us didn’t exist; we were both 18, and while I didn’t think of myself as ‘attractive’, this girl had a pornstar body with a sex drive to match my own, so sexy times were had all the time. Period? Shower sex 8 times a week, if I played my cards right anal wasn’t out of the question. Ass to mouth didn’t even phase this chick. I thought I was in love.

So, anyways, we’re two months into this thing. She’s not the brightest bulb in the book…at all, but I honestly didn’t give a shit. For example, she lived on the second story of a house that had windows all the way around it. She left the blinds up constantly, walked around naked all the time, yet couldn’t figure out why the 60-year-old man that lived next door (on the second story) was ‘always sitting in front of that window, watching me… it’s weird. I just don’t get it.’ GIRL, YOU LOOK LIKE A PORNHUB ADVERTISEMENT.

So, one day, we’re getting down and dirty….

I’m trying to get my dick in… wait why am I ‘trying’ to get my dick in. This should be a mechanical thing right now, like, all the prereqs have been met, panties are across the room somewhere, my dick could cut diamonds, the bed is a fucking slip and slide… Why the fuck can’t I get it in what the fuck…Oh.. there’s the head, okay… Ow… What the fuck ow, hold on girl, something isn’t right

So I at this point I’ve got the head and maybe an inch of staff in, and it feels like someone is standing on my dick. Tears are rolling down my face, she’s staring up at me with this pained looked on her face; I honestly thought I was going to have to call my brother in from another room with a hose to unknot us like a pair of dogs. So I start pulling back, and it fucking hurts. I honestly thought my dick was going to be ripped off. One of the most painful experiences in my life.

As my dick finally breaks free of this girls bear trap of a pussy, I feel something tear, but, not in me… and the most horrendous smell I’ve ever had the unfortunate luck to smell, starts wafting up from between us. My groin feels like I’ve been pissed on. Look down, it’s like a crime scene all over my lower half. Grab the trash can, start vomiting, share it so she can vomit, etc. Take her to the ER, she’s rushed back.

Turns out she had a cyst. I popped/ripped it trying to get my dick either in or out. It was only after she was out of the ER that she said ‘Yeah, it’s been a little painful when we fuck for the past month, but I kinda liked it.

TL;DR I want to vomit just remembering this.


2. Regret Renewed Every Day

Me: “This relationships making me miserable. I should get out.”

Her: “Sex?”

Me: renewed for six more months of misery.


3. Rag Doll Woman

She pretty much went limp and half catatonic once the clothes came off. She was lively and eager before that and back to her normal self afterward. I kept checking in with her and she was good with whatever I wanted to do, but would simply not actively participate or react. It was like fucking a drunk or sleeping person, except she was neither.


4. Dude Emulates Porn…Disappoints

He clearly learned sex by watching porn and has never been in a long term relationship. Think zero clitoral stimulation, awkward positions where you can think of nothing but the pain, uncomfortableness, or not hurting yourself, switching positions too frequently, unrelenting aggressive jackhammering or energizer bunny humping that lasts the entire session- which renders the vagina numb/sore, and cumming on tits or face without warning.


5. On The Day Of His Mother’s Funeral

When my mother died, my best friend’s girlfriend house-sat during the funeral, as a burglar-prevention gesture. When I came home, we talked for a while and then she jumped me. Yeah, she was preying on my emotional weakness that day, but I’d be lying if I said I wasn’t an eager participant. So I lost my virginity with my best friend’s gf on the day of my mother’s funeral. So very classy.


6. Trading BJs For Cuddles

He told me he gets blue balls and that it’s painful so he would guilt me into it every so often.

He would also never want to cuddle because he “can’t sleep like that”. Bitch I’m not asking you to fall asleep like that, I’m asking you for fucking affection. And I shouldn’t have to. I would bargain with him–I’d rub his back for 5 min if he cuddled with me for 5 min. He would talk me down to 3 min. And then during said 3 min he would guilt me into sex.

He was a gaslighter and a shitty human being. I didn’t see it at the time.


7. “I will kill any possible baby that was created during our debacle”

I dated a guy for about 3 months. We decided finally to do the deed. We both had one sexual partner previously, so we decided not to use a condom. Yes, I KNOW! We were stupid. Well, we get on the bed and proceed to try and get it on. He doesn’t kiss me, doesn’t do oral, and just flips me over on my stomach and lifts my butt into the air. Since I am not aroused due to the lack of foreplay, I am dry down there and he cannot insert. Well after 2 minutes of attempting to do so, he jumps up. I turn around and see him running to the bathroom. He has left me there naked to wait for him. When he comes back about 15 minutes later, I ask him what happened and he tells me that he came. Mind you no penetration occurred. So, I asked him how that happened and he tries to convince me that penetration did occur. The kid didn’t have a micro-penis so I would have felt it if that did happen. Then he starts asking me if I am going to take the morning after pill. I kept telling him no because we didn’t have sex, but he kept pushing it. He asked me to come into the kitchen, so I did. He took out a tequila bottle and tried to force me to drink it so that “I will kill any possible baby that was created during our debacle”. Just to let everyone know, this man was 21 years old and studying biomedical sciences at the university. Afterward, he drove me back home and during the ride told me that he wants to see other people and is not ready for a relationship. Well, about a year later, I decided to give us hooking up another shot. This time he ended up coming by me kissing his stomach and the area around his penis.


8. She Died

She died. Not during sex (that would’ve been awkward) but about 4 weeks later in a car accident.. if we hadn’t have hooked up that night I wouldn’t have had any feelings for her and wouldn’t have spent years feeling alone and miserable.


9. Realizing You’re Not Cheater Material

He was married. I was young and single and thought I didn’t care… until he touched me. I suddenly felt a pit in my stomach and couldn’t enjoy it at all. All I could do was think about his wife sitting at home. I felt so awful. I never saw him again. Though I’m sure he didn’t stop being unfaithful.


10. A Pet Snake Appears In This Story

Lost my virginity to my ex. We hadn’t talked till we broke up but as soon as we got into contact with each other we decided we might as well. It was so awkward. Didn’t even get it all the way in, and halfway through my pet snake (no pun intended) that had been missing for a few weeks decided to make an appearance. We haven’t talked since.


11. Killing Friendships

We were commuting to and from school, and one night she was talking about how she wanted to fuck. She was going through her phone and saying stuff like “why doesn’t anyone wanna fuck tonight?” over and over. I thought she was giving really obvious hints. So I pulled over in a dark spot and started making out with her. She enjoyed that and was giggling. Then we got in the back seat and I went down on her. It was bone dry the entire time, and she wouldn’t let me touch anything except her clit. We stopped about 30 minutes later and I took her home. It ruined our friendship, we used to be best buddies, but now I haven’t even talked to her in over a year.


12. ‘The Ring’ Claims Another Victim

She was giving me head on the basement couch while “The Ring” was playing (this was near the end). Volume is super low. It’s all going good, then I feel like I’m about to nut, roll over and look at the TV in ecstasy when I see this:

via YouTube

Now, at this point, I had completely forgotten about what we were watching, so I was utterly in shock. I thrust up really quickly (it was simply a reflex). Well, that triggered a reflex of its own, also known as her gag reflex.

Worst part? I still nutted a few seconds later after she managed to get out of there (not without graciously returning to me her half of the Domino’s pizza we had previously shared.)

What a great night that was. The best part? We’re going to the same college next year (let the good times roll!).


13. A Rough Way To Learn About Yourself

I hadn’t realised I need an emotional connection to really enjoy sex. We were nothing but pre-FWB’s and I cried after when he went up to have his shower.


14. Scared Into False Rape Charges

In high school her dad found out and she said I raped her. Cops got involved. She told the truth at the hospital while getting a rape kit performed. Ruined several years of my life.


15. Seriously though, don’t sleep with your friends

Not so much the consensual sex, but the whole follow-up, mostly timing.

I’m not unfamiliar with sleeping with friends and having FWB in my peer circle. But last summer I started getting a little crush on a really good friend of mine. Couple of caveats though. I’m 5’7″, she’s 6’0, though that didn’t really bother me. But, most importantly, even though we’re the same age (mid-twenties), she had never even kissed a guy before. She never really got male attention, partly because of her height I guess (her looks are okay), but mostly because of her personality. If you know her, she’s an amazing person and she’s hilarious. But she has a shield that she keeps up most of the time for people she doesn’t know and she can come over as being quite abrasive. On top of that, we live pretty different life styles and have some widely differing views on sexuality and relationships.

Nonetheless, I told her about my crush, but at first, she rejected me. I was fine with it and moved on after a few days, thinking it was probably for the better. But she came back on her rejection, but by that time I didn’t really have the crush anymore. We still ended up sleeping together for about a month. During which we were both confused about whether or not we should or shouldn’t pursue whatever it was we were doing.

We ended up agreeing that it was probably a bad idea for us to try a relationship and we should end it. So we did. She was okay with the decision, but it still hurt a bit, because she had never felt so much at ease with someone and had never received that kind of attention.

Then, less than a week later, I went on a Tinder date with a girl. I’m not the type to easily fall in love with someone (truly in love, not a crush) and I wasn’t looking for anything serious. Neither was she, she had even broken off things with previous FWBs when they started getting feelings, as she didn’t want a relationship. But, we both fell in love almost instantly. It took less than two weeks for us to make it ‘official’, and the reason it took that long is because we both felt it would be ridiculous to do it earlier.

Needless to say, the first girl was a bit hurt by the whole ordeal and it kind of damaged our friendship. But, things have been worked out, though she still can’t stand my SO. She says the thing that hurt the most was the timing. She didn’t mind me getting someone new (she knew I would), and that she’s actually very happy for me. She just wished it had taken a bit more than 3 weeks.


16. Breaking His Dry Spell

I’m not shallow (at least I tell myself that) and give everyone a chance. this girl I’ve known since high school and was fairly cute in high school messaged me on Facebook. Before I knew it we were planning to meet up for some fun. she had to be at least 75 pounds heavier than her pictures suggested, her face looked nothing like the pictures; for a second I honestly thought the wrong person had stepped into my car or maybe her sister or something used her profile to meet me…me being the thirsty fuck I was and her telling me I could do whatever I wanted to her made me go through with it.

She said less than 20 words from the time she got in my car to the time I took her back home (she was super talkative online). It’s not like I’m expecting her to get all dressed up or anything but she looked like she had just woken up and was wearing what she slept in the night before. She was also the worst kisser ever. Like an aggressive vacuum on my face with a rapist for a tongue. As soon as we finished I realized not only did I feel less of a connection than when we spoke online, I also felt disgusted that I basically was catfished (albeit, they were her pictures just very old and maybe touched up) and still decided it was ok since she was willing to have sex.

I picked up some fast food on the way home and smelled her on my fingers while I was about to take my first bite. I pulled over and threw up almost too fast to get my car door open. I couldn’t eat, not because I was still gagging, but the shame after that made me feel horrible like I’d just ruined my life. Worst sexual experience ever.

I’ve stopped talking to people online, I haven’t had sex since then, and I can remember the smell and can’t eat at jack in the box anymore because of her box smell burned into my head. The worst part is I’m not ashamed of how she looked or that she was nothing like the person she was online, it was the impersonal feeling I felt like I was supposed to pay her or something since it was literally, hi, fuck, bye. I know now without any sort of connection between our personalities I’ll literally hate myself into vomiting after sex, never knew that about myself and wish I didn’t have to learn it. 0/10 never again even if this dry spell lasts the rest of my life.


17. “Date With Bae”

He told me that his newly pregnant girlfriend had just dumped him. He even showed me that she had blocked him on all social media. I said “fuck it” and we started being friends with benefits for a couple weeks. I later saw her tagging him in facebook posts with shit like “date with bae.” Like a day after we had just fucked too. I’ve been cheated on before, and I don’t want to be a third party to cheating ever again. This is why I have trust issues.


18. Ouch!

Moaning the name of her ex.


19. “Stretch Me Out And Cum Inside Me!”

Oh my goodness this happened last week. Worst experience ever. There was this cute girl I had met working earlier this year and we had been texting. I asked if she wanted to study with me and she suggested we do it at my place. Sure. Then she asks for wine. Sure? I could tell she was kinda immature for her age but I just went with it. After like 20 minutes of studying she lead me to my bed and the vibe was super chill but could realize she was a little tipsy. After one glass. And asked for another. So I grabbed one as well just kinda going with the flow. She is being super flirty and I am enjoying myself, until, she starts crying about her friends. I try to help but she is just hysterically crying at this point. Ok. lemme getchu a tissue. Being playful and she starts to laugh again. When I walk away she chugs my wine and I am just kinda like wtf. Gets on top of me and while she is grinding on top of me starts balling again. WTF. I am super uncomfortable and say, “I am going to take you home” She becomes even more hysterical and like yells, “I WANT YOU TO STRETCH ME OUT AND COME INSIDE ME” jumps off, runs into the bathroom and pukes…. nooooooooooooo you need to go home. It’s not even 8 in the evening at this point. Kick her out because she refuses for me to drive her, so fine, damn get a friend to drive you. I went over to my neighbor’s house and told her about it because she could hear some shit going on and both watched this drunken girl stumble into her friend’s car and drive away. It was so bad lol.

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