50 Women Reveal The Raunchy Details Of Their Biggest Hookup Mistake Ever
In the morning he confessed that he'd been interested in me for years and that his dreams had come true and started talking about our future. It was very awkward.
By 
Brittany Cox
It happens. Horrible. Hookups. Get ready to cringe.
1. Checking my oil
I hooked up with this guy a few times who I had good chemistry with. He wasn’t bad in bed but he was so freaking awkward about sex.
We were making out naked, and he hadn’t touched me anywhere between my legs.He decides it’s penetration time and gets up to get the condom from the bedside table. Before opening the condom and putting it on, he reaches down and puts one finger inside me and takes it out in one movement, then puts the condom on. With no words. I felt like he was checking the oil.
2. We just had sex and then…
Had what I thought was just going to be a one night stand with a dude. In the morning he confessed that he’d been interested in me for years and that his dreams had come true and started talking about our future. It was very awkward.
3. Blood. Blood everywhere
Hooked up with this cute guy for a night, both of us just wanted a one night stand or a FWB at max. We started having sex and it was pretty great, felt good then suddenly he pulls out and his condom is COVERED in blood. Like covered. I got really freaked out and told him embarrassingly that my period is a little weird to which he said (to my horror) “it isn’t you, it’s me”.
I just looked at him trying to understand how he could have been on a period (my brain was not working) and then he took the condom off (which now had a mix of semen and blood in it, SORRY for the TMI) and showed me some stitches on his penis that had ripped during sex (he said I was too tight). He also said “can’t believe this happened again”. Thankfully nothing was on me, I washed up and left and we never spoke again.
— ynok822
4. Wow, this guy really sucks
The guy who I thought was using a condom but I guess in the middle of sex, he took it off (I was very drunk and didn’t notice). Did not even know until I was showing symptoms of chlamydia and I had to ask him about it. Biggest scare of my sex life.
5. Not exactly sex but
Met a guy at a bar. He seemed clean, law abiding, kind. He came over. Start making out, took off my bra, suddenly pulls a crack pipe out of his pants and asks if he can “do this quick here or should he use the bathroom?” Asked him to leave and he did. Kept texting me afterwards saying he doesn’t need to do it in front of me, he found a kmart parking lot to do it in and he can come back. I blocked him.
6. He started preaching for me
I wanted to hook up with a guy with abs. I found a guy online who had great pictures. He was skinny and tall. He was into bbw, and I was to small for his tastes but we agreed to hook up. He comes over to my place. We fuck like rabbits, cuddle a bit, then it’s time for him to leave.
He said God Bless before almost closing the door behind him. I snickered and said yeah. He stopped dead in his tracks. He asked what was that? I said I don’t believe in gods. Suddenly he turns on Christian boy mode and is compelled to witness to me. He says he’ll ask for forgiveness for the hook up and pray for me. He had guys give him blow jobs before but he’s not gay because god forgave him. I was just like… Omg leave.
— Virgoan
7. He started complaining about his wife
Hooked up with a pilot who was in my city just for one night. After we got done fucking, he started talking about his wife in Texas – and then his girlfriend in Atlanta called him with some drama. I just left then.
8. He cried after he came
I hooked up with an ex of mine a couple months after we’d broken up. I had ended the relationship, but it was because he didn’t want to move the relationship forward, because he “wasn’t sure,” so I figured it would be fine. Sex with him was always awesome, we weren’t together any more so no strings attached.
Yeah, the sex itself was great. But afterwards he just sobbed for a really long time about how much he missed me. The feeling was not mutual, and it was very awkward.
— Jilltro
9. We had sex outside a stranger’s house
Years ago, it was Valentine’s Day. I had broken up with a guy the night before, and some single friends and I went to the gay bar to dance. I met this dude there and we were flirting – he was cute, but nothing special, and there were some obnoxious aspects to his personality. For example, he was bragging about his paycheck and he took it out and showed it to me; I don’t remember the amount but I remember it wasn’t as impressive as he thought it was, lol.
So this wasn’t someone I’d date but I was looking for a hookup and nothing more. We decided to leave the bar and go hook up. I was living with my parents at the time and he said he was too, but we could park in the driveway of his parents’ house and have sex there. I agreed (again, I was younger and had been drinking and i would NOT do this today).
So he directs me to his driveway, I get on top of him in the passenger seat, he puts on a condom, we have adequate sex, he comes and I’m just like ready to be done with this guy at this point. I’m back in the driver’s seat getting my clothes in order when a man comes out of the house.
I’m like, “Is that your dad?” He says no. I ask who it is. He says, “I don’t know, this isn’t my house!” All incredulous, like I was ridiculous for asking. I am PISSED now and I peel out of the driveway. I don’t want to fully cuss him out but I basically tell him he’s an idiot, an asshole, and to stop talking to me.
When I dropped him off by the bar we met at, he tried to convince me to drive him and his friend to a party. I had to yell at him to get out of my car.
I’ve had a few regrettable hookups, but that was probably the most shameful.
10. This is not okay
The guy who took the condom off, stuck it back in and ejaculated inside me, even though I was screaming no. Also it was pretty much the first time I’d ever had sex. (First guy hardly counted because he only got half his dick in before he came.)
11. More excited about chess than me
So i met this guy on tinder. He was really cute and we texted for a few days. One night i went out, got VERY drunk and decided I wanted to hook up.
So i text the guy at 5 a.m on a Saturday saying something like “wanna come play chess?” after he knew i was going out. It was the first time I was seeing him in person and I know it was reckless, but I was very very drunk and thought it was a good idea.
The guy comes in and we instantly start to make out and I start to direct him to my bed (I live in a small apartment, so the bed is not far from the door).
Everything is going as planned in my drunk head UNTIL he sees the chess game on my library… He grabs the box all excited, goes to my table and starts to prepare the game. I’m dumbfounded. But you know, I’m drunk, so i go like “fuck it”, get some coffee ready and start playing chess.
Needless to say, he absolutely destroyed me.
But it wasn’t over yet. He wanted to play AGAIN. By this point I’m not even that drunk anymore, so I didn’t even know how to handle the situation and started to realize what a bad idea this thing was. Let’s add to this that during all this time he was talking about this girl he had seen ONCE over six months ago. And he was very very socially awkward. Well, more like socially inept. But handsome, very handsome.
So we are at the middle of the second game when i get fed up with the whole situation and decide I am having sex or he is leaving. This time I manage to distract him from the game and we go to the bed and everything is back on track. But things keep getting worse as I wasn’t expecting was this guy to be HUGE. He had the biggest thing i had seen. Even in porn. I can’t even call that thing a dick. I was terrorized and also quite mad at the whole situation. Needless to say it was anatomically impossible to have sex.
At this point i’m more than convinced that I want this guy to leave and never see him again. And, good thing, he is leaving.
I should have mentioned before that this guy is aprox 1,95 mts and i’m only 1,57 mts.
When I’m saying good bye to him he makes some joke about my height and I make the horrible mistake of saying “yeah, my friends used to call me Juli from the shire”. Now, i’m not a huge fan of lotr and my friends aren’t either, but this guy was. he got SO excited about me saying that and he just came back in and started talking about the books and the movies and the Silmarillion. He talked to me about all this for maybe about an hour and half.
Eventually I kicked him out. It was around 10 am in the morning by the time he left. And we didn’t have sex.
12. He roared like a lion
My first one night stand. I met him at a club, thought he was hot (I may have been drinking) but he told me he lived with his teenage girlfriend but that they were broken up. He was 21, she was 17. (I know, I know. Red flag!)
Anyway I take him home and we hook up and when he comes he ROARS like some kind of bear or lion or something. That was pretty wtf. It wouldn’t have been so bad but I had three male housemates at the time and they found it absolutely hilarious. They roared at me every time I walked in the door for at least a year, and then explained the joke to everyone we knew. HA.
But the worst part is that several days later, his 17 year old girlfriend shows up at my house, screaming and pounding on the door. I opened it because you know, neighbors and such. She was very, very obviously pregnant. And apparently they were absolutely NOT on a break. I felt bad but really, how the fuck was I supposed to know? This was way before social media (unless you count LiveJournal) Sadly I never ran into him again, because there were a lot of words I wanted to say to him for being such a scumbag.
13. I thought he was gonna use the vibrator
We were drunk, so at first he couldn’t get it up, and we started using a vibrator instead. I close my eyes to enjoy the moment, and when I open them again… he’s fucking me. Without a condom.
I got tested the next week and everything was ok, but that was a huge scare.
— msstark
14. I am a victim of the naked an
Met a guy online, agreed to meet up at a coffee shop and the head out to dinner. Get to the coffee shop. See a guy that kinda looks like the profile picture, hitting on some other girl. Her body language was very clearly “eww get this guy away from me”. Yeah I should have left then. Anyway The girl leaves and he makes his way over to me and says hi I’m Mike (because that was his name) You must be PB. La la la let’s go out to the restaurant. On the walk over (three blocks through down town at like 5:30pm) he suggests we just go back to his place and “just make out” for a while before dinner. I turn him down flat.
We get to dinner, the food is good, the service was beyond horrible. We have good conversations but I can tell that this isn’t going to go anywhere.
We decide to head out to the pub down the street to watch the Habs play (Hockey Playoffs). He asks if I mind if we stop at his Condo so he can change (he was still in a suit) before the pub.
I say sure why not, his condo was literally on the way to the pub. Fancy condo, right downtown, even had a doorman (I’ve always wanted a doorman).
Anyway go up to his condo and I’m sitting in his kitchen and he comes out of the hall way to the bathroom/bedroom NAKED and says “Hey baby like my Hard-on”.
I kid you not… I COULDN’T SEE HIS MICRO-DICK FOR THE FOREST OF PUBES. I laughed my ass off and noped my way out of there.
On the way out of the Condo the door man laughed and asked if the guy tried “The Naked man”.
He has never seen it work on a single girl “Mike” has brought home.
15. He kept begging me to let him take his condom off
So I go on a date with a guy I’ve known for a while, he makes dinner, conversation is good, great kisser, yay! Things start heating up, so we go to his room. He tries to put it in, and I say “Hold up, condom dude.” Then the whole time he keeps asking me to take it off.
Eventually I stop and have a serious conversation about boundaries, and how not only is a condom for my safety, but his too. I have to explain to him that it is entirely possible to have something and not have symptoms, or a small chance of pregnancy on my end. Like holy fuck, what kind of adult doesn’t know this?
16. 90 second shooter
Guy friend.
We hooked up a handful of times. He didn’t last more than 90 seconds each time.
We are in a group chat (I’m token female) and he always talks about slaying pussy and all the girls he’s banging. I don’t know if he has premature ejaculation problems with all of them but I never said anything to anyone about hooking up with him and I just kind of lol whenever he mentions his studliness
17. Some really bad FWBs
My last FWB. The guy simply had almost zero stamina. First BJ I gave him went like this: thup thup thup thup thup thup….squirt. Just that fast (I used thup because I don’t know how to type a sucking noise heh).
Well it was our first time together, so I figured he had stage fright. He recovered and we went to PIV. Shag shag shag shag shag….squirt. Just about that fast.
This happened a few more times, and I eventually scored an orgasm. Keep in mind that I am really easy to give an orgasm to, but he couldn’t muster that on a regular basis. TWO MINUTES is all it took usually for me, and he’d jizz out long before that. I finally got tired of it and told him to buzz off.
Another bad one was the first guy I met when I moved here. He was divorced, and complained that his ex wasn’t ever passionate. Sooo anyway, I was giving him this nice BJ. I’m pretty good at them, and never had a guy be totally silent the whole time…but this guy was. Not a single moan or peep or anything. And when he came, not a single indication that he enjoyed a single moment of it. And then sex was the same thing. No noises or anything at all. As I said, I am super easy to give an orgasm to, but after a few minutes, I tuned out and wanted it done. Mr Passionate was about as much fun as fucking a mannequin. I never called him back…at least my vibrator makes funny noises and doesn’t come in my mouth.
18. The cat watching wasn’t the worst part, but it didn’t help
I went on one date with this guy and he was really, really boring. When we texted he was so interesting and had a ton to talk about, but when we met, we had no chemistry and our conversation didn’t flow at all. I figured I’d give him another chance cause he was still kinda cute and really considerate and very well educated, so he could tell me a lot of cool stuff about plants and stuff.
Second date’s at his apartment and I show up and conversation is just plain dead despite all my efforts to keep it afloat. He’s got a cat and I’m petting it for like two hours, which is entirely uncharacteristic of me. I’m allergic to cats and the feeling of hair freaks me the fuck out.
Eventually he’s like ‘can I kiss you?’ and I figure yeah sure whatever we’ll fuck and get this over with and then I’ll go home. Unfortunately he’s legit the worst kisser I’ve ever kissed. His mouth keeps going around my mouth, like he’s just trying to eat my lips or something. I’m just like what the fuck I’ll just kiss something that’s not his face, but his entire body is like, salty? Maybe he was nervous or something I dunno.
We eventually move to his bedroom and we’re fooling around and he’s fuckin doin his darnedest to finger me but he’s got no clue what he’s doing and I’m so uninterested at this point that I’m just like whatever I’ve just gotta fake it and then we’ll fuck and then I’m out of here. His cat comes in the open door during my performance and sits on the bed next to me and he does nothing about it. It watches us.
When he’s done that he gets up to get a condom. I’ve got really bad eyesight, but I’ve taken my glasses off because this dude does not know how to keep his face off them. He comes back with a condom on and I feel like I can see that something is weird about it, but I just figure I’m imagining things. I should note now that his penis is small. Like, exceptionally small. This isn’t a problem at all for me; it’s just relevant.
He’s on top of me and the cat’s still watching and he just keeps saying my name and honestly if it was anybody else it’d be super hot but no I’m just nauseated by it. He’s taking a while so I suggest we move positions; I’m getting on top and I go to guide him back into me and something is Wrong.
The condom is missing. It’s not on the bed and it’s not on his dick. There’s only one place it could possibly be. I have to tell him twelve times to leave before he actually leaves the room. He just keeps moving slightly further away with his hands over his face knowing what’s happened and completely powerless to fix it. The cat does not respond to my instructions.
I fish the condom out of my body and tell him I’m leaving cause it’s weird. He says ‘yeah, that’s happened before…’ and what was an uncomfortable and embarrassing mistake between us turned into an egregious offense.
I ended up texting another guy I was dating who lived nearby and telling him the story and he told me to come over and I screamed a bit, cleaned up, and had a pretty nice time with the rest of my evening.
Later on I wrote the guy a long text saying pretty much ‘it’s not a problem that you need smaller condoms; it’s a problem that you use the wrong size and didn’t learn the first goddamn time. Also you need to practice kissing and I’m blocking you.’
19. Really creepy older guy
The guy I lost my virginity to. I met him when I was 13 and he was 20 – he was a family friend and I went to school with his younger brother. I harbored a huge, obsessive crush on him. I would fill journals talking about how much I “loved” him and wanted to be with him. For the most part he treated me like a little sister but there were times where I felt like he was flirting with me, and of course that got my hopes up. The main problem I saw wasn’t the age difference, it was the fact that he had a girlfriend.
Anyway, three years go by, I was 16 and he was 23. He and his girlfriend ended up breaking up and he randomly messaged me one day and told me about it. I was like “oh no, I’m so sorry to hear that” and he was basically saying “yeah, but it would make me feel better if there was someone I could have a secret rendezvous with” (he used those words lol). I had never even had my first kiss, but I saw this as my shot, like the thing that I’d been wanting for three years…. So I agreed, we hooked up, he kept pressuring me to go further and have actual sex. I didn’t really feel comfortable or ready but he told me that he loved me, he told me he wanted to “run away with me” so we could be together, shit like that (also, side note, I told him cheesy stuff like “oh I’ve wanted you for so long” and he told me that if I made a move on him back then he would have reciprocated…. which is FUCKING CREEPY AND DISGUSTING LOOKING BACK BECAUSE I WAS 13!!)…. So I eventually went with it. The very next day, he told me he was going to try to get back together with his ex. She turned him down.
Now he’s almost 30 and has nothing going for him in his life, so that makes me feel a bit better. I’m about to turn 22 and I just think it’s funny looking back, how I thought he was soooo mature and amazing and “our connection transcends age” and stuff like that, but now being that age, the idea of going for someone under 18 is physically nauseating to me.
20. Headcase flipped out over a jacket
This happened around 8 years ago when I was doing the single parenting thing. Met a guy through a mutual friend, swapped numbers, and spent a few weeks texting back and forth. The guy was attractive, employed, funny and what I thought at the time, completely fucking normal.
So a few weekends later, I found myself child free and we’d planned him to come over for a few drinks and a movie.
I had a joint in my room that was given to me weeks earlier by a friend that I was waiting for the right time to hit. I’d offered, he was keen, so we roached that baby up over a chat and a laugh. The night went great, ended up in the bedroom and I explained he couldn’t stay the night as I wasn’t sure what time my daughter was being dropped off the next morning. He was cool with that.
Fast forward to next day I wake up to messages from him saying he’d left his jacket at my house, he needs it, and apparently needs it RIGHT NOW. Messages coming across rude as hell, which was odd. Again, I explain I’ve gotta stay home and wait for daughter, but he can call past quickly and grab it.
This wasn’t good enough apparently, and he keeps aggressively messaging me demanding that I bring it to him now. I tell him no, I can’t, and I’m not interested in keeping this conversation going, he knows where I live, come and get it. I’m waiting for daughter. I offer to drop it at his work the following day as I pass his work on the way to mine, still not good enough.
So later I receive a message telling me since I have now stolen his jacket, he wanted me to know he called the police and told them about the drugs at my house. Wtf!!
Turns out he really did too. The police arrived at mine a few days later, he told them I was growing weed!! They were great. Had a quick look around and found nothing, obviously. We had a chat and told them honestly what had happened. They were really good about it.
About 12 months later, I get a random apology text, and an invitation to dinner with him. I respectfully decline, and he tells me that he’s really upset I said no because he thinks he’s in love with me.
So that’s my regretful hook up. Dude was a headcase. A girl I went to school with started dating him a few years later, and her Facebook page is pretty interesting, he’s clearly a fucking nut job.
21. Fucked my math teacher
Hooked up with my math teacher when I was 14. Ugh. Wish I could take that one back. It took YEARS to process the emotional garbage.
22. It just got worse and worse
The guy I went on a date with because I was sad and he was funny. Turns out the funny guy thing was hiding Stage Five Clinger-itis. Sex was great but even though I was clear about what I wanted, he clearly wanted a relationship so I went along with it.
He started in with the I love yous in less than a month and made me (not really, but you know) say it in the middle of sex. When I broke it off because I met the man who would become my husband, he called me at work to tell me how disgusting I was.
Oh, and he gave me HPV.
OH, and I just found out recently, then he fucked my sister. What a prize specimen.
Don’t worry though, Tom. I might hate you but I’ll still never tell anyone your secrets.
23. Didn’t understand what we were
The hook-up itself was fine, but the next day he got pretty clingy and it was obvious he just wasn’t a ONS kinda guy. Which is fine, except I had explicitly said I was only after a ONS.
24. Tiny dicks
Two words: micro penis.
Happened on 2 separate occasions. One was inexperienced and i dont think he really had any clue, so i felt really bad for him. The other one was aware and super rough with foreplay to what i assume compensate. I kept trying to calm him down, every time i reached for his dick he would shove my hand away, then suddenly he puts on a condom is on top of me and kinda grinds agaist me twice and then cums (i think). I felt nothing. Years later i see on Facebook he’s gotten married. I wonder if they have some situation or arrangement to accommodate…
25. Let a frat boy take my virginity
I lost my virginity five years ago to a douchey frat guy who, last I saw, was smoking a gross cigar and wearing a Make America Great Again bucket hat in his Facebook profile picture.
I felt my vagina clench up in regret.
— ladydece
26. Tricked me into cheating
Guy I had a crush on for years starts hitting on me, he says he’s on a break with his GF so we fuck. His dick is disappointingly short, he didn’t even try to make me cum, and the next day he’s posting pictures with his girlfriend publicly saying how much he loves her. So obviously not on a break. I was dumb to believe that lie especially since I know he has a history of cheating.
27. It was just boring
My first “boyfriend”. We only dated for about six weeks. This was about six years ago, before I even knew what I liked in a man and really anything about myself. We met at work, and started seeing each other after he got rejected by another coworker.
The sex was boring and I didn’t feel anything, even though he was my first. He was also boring and I never had fun with him. He couldn’t hold a conversation and all he did was smoke weed and watch sports. I think it was a hookup because it wasn’t a loving relationship at all. We weren’t even friends
28. Banging a dude got him fired
I might’ve gotten a guy fired from his job.
He was in town for a couple months on work, and we’d talked about hooking up. He just wanted some female company while he was here, and I wanted something with no strings.
What I didn’t know was that he wasn’t supposed to have people in his room, his coworker had the room next door, and they had to be up super early the next morning.
I’m not quiet. I tried to keep it down, because we were in a hotel and I wanted to be respectful. So I didn’t wake up the whole floor or anything, but his neighbor certainly heard.
The sex was just okay, although he was very nervous. I would’ve given him another shot, but he said he didn’t feel like he could risk it again. Never heard from him again after that, not sure if he ended up getting fired or in just big trouble.
— MzHartz
29. Was drunk 2 months straight destroyed friendship
I had just been broken up and was still very much in love with my ex. We had been friends for years before we dated. I went on a 3 month bender after we broke up (young and dumb). He was in a different state so I hung out with our friend group alot and ended up sleeping with a friend of ours. Now that really wouldn’t be a problem, but said friend has had a crush on me the entire time we had known each other (going on 10 years at that point) and after we had sex, he started getting super romantic and stuff. It was…awkward for me. I’ve never felt like that for said friend. We only slept together because I was so fucking drunk.
I literally woke up to him pulling my hand to his bedroom and we’d slept in the same bed plenty of times so I didn’t think anything of it. Next thing I know, we’re having sex. I really regretted it. We ended up having sex a few more times because I just felt so fucking guilty and couldn’t say no. He was always looking at me with such fucking hope and I felt nothing for him. I was still crying my eyes out anytime I thought to much of my ex. I stopped inviting myself over and made myself scarce. He stopped talking to me . We’re still friends on FB and he seems to be doing great tho so I’m really happy for him.
He was a terrible lay tho. His breath always stunk and he always wanted to make out. He was very well endowed but didn’t really know how to use it very well… and I was young and usually drunk so I never said anything.
I wish we’d never slept together. It really tainted our friendship. But I don’t think we would have stayed friends anyway in the long run.
30. His friends burst in, also he was a creep
Hooked up with a guy because I was horny and bored. He wasn’t particularly attractive but he was a friend and I enjoyed hanging out with him. He also talked a pretty big game. I got to his apartment and it was a total mess. He was kind of aggressive but not in a wholly unsexy way so I went with it. Minimal foreplay and a really small penis (maybe 3 inches) later, I couldn’t feel anything and I just really wasn’t into it.
He forgot some friends were coming over and he’d forgotten to cancel plans with them and we got interrupted, so I went to the bathroom. The bathtub was clogged and half filled with water and tons of hair. I left pretty much immediately. Could NOT handle that.
Later, he messaged me and told me he didn’t have an orgasm (as if I’d be surprised? Or that I should do something about it? I’m not sure). I said “Oh, well, neither did I.”
In the end, he turned out to be a creep. He decided it would be appropriate (a few years later) to message me because I’d posted a few (very unsexy) pole fitness videos on my instagram and tell me that it gave him erections. I pointed out that he had a girlfriend. His response? “yeahhh.” I blocked him after that.
31. He was a total sociopath
Got involved with a sociopath.
He seemed incredibly charming and interesting at first. In my misguided and inexperienced (deeply in denial lesbian) opinion, he was also a good lay, so I thought I’d struck fwb gold.
Turned out to be a manipulative ass who did a lot of damage to my self esteem and sense of self worth. He would switch between emotion dumping while expecting me to play therapist and constantly putting me down and making fun of me. I was so under his influence that I was willing to tolerate almost anything from him, which I now regret because I could have been seriously hurt.
Also he was terrible in bed. The year we knew each other he never once kissed me or did any sort of foreplay. He never even tried to get me off. Bastard also gave me HPV.
I look back now and have no clue why I was so enamored with him. He was an unattractive, boring, toxic man baby that no one liked.
I deeply regret the experience because I let myself be treated like crap. And I kept going back for more. I was pathetic, desperate. I never want to be that person again.
32. He fucked me as I vomited
I was 17 and me and this dude had awesome chemistry. Like he was a great kisser and our conversations flowed naturally. We had been talking for about a year off and on and he finally came to town again so I was just ready to fuck him by then.
We get super drunk at a party, head to the guest room and I immediately vomit into the trash can. He somehow is cool with that and keeps trying to kiss me and I’m drunk so fuck it I guess. Then he doesn’t touch my vagina even tho I go down on him and he flips me on my stomach and did not warn me he was gigantic and just shoves it in. My soul left my body. After 12 pumps, I counted, he finishes on my back and falls asleep. 1/10.
33. Study abroad sex nightmare
Oh god. I was studying abroad and met this dude at the club. I was looking to broaden my horizons and let loose a little and he was attractive and fun, so I thought, why not? We didn’t do anything more than make out that first night and I should have left it there because he was a terrible kisser. But then I wouldn’t have this story!
We texted for a few days while I went on a trip, and he took me out when I got back. I drank a little too much, took him home, yadda yadda. But wait, he forgot a condom. I snagged one from my roommate and I thought we would be good to go from there. I tried to set some mood lighting but he was not having that. He pulled my shades and made it absolutely pitch black in my room before we even got naked. I tried to turn a lamp on and he politely requested that I leave it off. Ooooookay dude.
So we started messing around and it quickly became obvious that he didn’t know what he was doing. The foreplay consisted of me trying to go down on him and him stopping me, and then he proceeded to jackhammer me WHILE BEING COMPLETELY SILENT. Not a peep. I tried to switch things up but he wanted missionary and that was it. I didn’t even know when he finished, he just stopped.
I wish I could say I learned my lesson, but I thought he might have just been nervous so when he asked me out again I said yes. Exact. Same. Performance. Right down to the forgotten condom. I was done after that.
34. I let him keep thrusting even when it hurt
Letting him keep thrusting even though I was in a lot of pain, because I wasn’t confident enough to stop the sex from finishing. Believing him when he said he had no STD’s and it was okay to keep going even when the condom broke. He finally finished and decided on his own that “no condom” also meant “okay to straight up jizz inside” me.
He was honestly a nice guy besides the jizz part, and never knew I objected to any of this. Luckily he was telling the truth about being clean. He cuddled with me intensely the whole night and I lay there wanting to die. Never texted him back after that, very sad for him.
I’ll never forget how spineless I was at 21.
35. Tinder English teacher was actually MARRIED
I met a guy on Tinder who seemed really cool. He was an English teacher (I majored in English) whose views seemed to completely align with mine (I now realize he’d just listen to my opinions and mirror them or when we’d disagree on something he’d say he was joking and then agree with me). He said he was basically divorced, they were in the final parts of the process and that everything would be finalized soon, but if he understood if I wasn’t comfortable with that. I should’ve noped out of there then, but I felt like he was being honest from the get go and that I should give him a chance. He constantly told me to always be honest and if I ever felt weird about hooking up to tell him.
He was really attractive and was good at foreplay, even though he never lasted more than 2 minutes. He said it was because he hadn’t had sex in like 5 years, and I sympathized. But I started to notice that he could only ever hang out at weird hours during the day and always had to leave around 5 or 530. So I had my suspicions that something was up, but I couldn’t tell if I was just being paranoid.
No, I wasn’t. I saw his wife and her stuff in the background of one of his snapchats. And it wasn’t until he asked me if we were still ok a few days later that I confronted him. He instantly confessed that he was still married and wasn’t planning on getting divorced because his wife had recently been diagnosed with a serious mental illness and he didn’t feel right leaving her. Then he gave me some bullshit sob story about how much he hated his life and how he thought I knew about his wife because I said at the beginning that if they ended up getting back together that I didn’t want to be involved in any drama. He said that he took that to mean that I wasn’t interested in the details of his relationship status. I told him he intentionally misled me and that I never wanted to see or hear from him again. He tried to text me a few weeks later saying he missed me and our conversations. I blocked his number.
Fuck you Tom, you’re literal garbage.
36. Cat attacks us during sex
Met this guy, we started messing around. While we are in the middle of doing the deed, my cat jumps on my bed, scratches him across his forehead and he starts bleeding down on to me and my pillow. Sad thing is that the part I regret is me catching feelings for him as the deed doing continued on other occasions. :(
37. Sex turns into around-town adventure
So I really liked this guy. We were at a party, I was quite drunk and we start hooking up. We go out to his car, have some sex, and then I need to pee, so I run off. I ended up running around town for about two hours, before I’m able to find my way back. In the middle of winter, with no shoes on. His car got stolen that night too.
Anyway it was the start of uni break and I didn’t hear anything from him over the break. I got back and he pulls me aside one day to ask if I was pregnant, because The condom broke. My body shape naturally looks pregnant (though I’m slim), especially when I bloat, so I was feeling really fantastic about myself after that. The worst part was I didn’t remember anything much about the incident so didn’t know about the condom. And he waited two weeks! I wasn’t on any birth control but could’ve got plan b or something. Asking if I was pregnant instead of telling me what happened was the wrong way about it.
My fourth year project was then with him and we had to awkwardly hang out for weeks.
— kati_pai
38. Sent me home with cookies, but the rest was awful
Once I hooked up with a guy, fluids were exchanged, and then he revealed that he was an IV drug user who had been to rehab but fell off the wagon four weeks ago with a shared the needle. I freaked, he reminded me that he had been tested, and I said, “But if it was four weeks ago, it might not show up on a test yet.”
That was a really tough year of getting tested and re-tested. He wasn’t any good in bed, either–really a pillow princess. So not worth it! The best thing about it was that he sent me home with cookies, which didn’t exactly make up for the stress. Luckily, all tests were negative.
39. Buckets of sweat
He had hyperhidrosis…when someone says they “sweat buckets,” that was literally him.
I knew this beforehand, but it wasn’t until we were having sex that it was in full force. I was either sliding off of him or if he was on top, his sweat was dripping profusely all over my face, eyes, body. It just really made you lose the moment. Thank god I had a plastic cover on my mattress underneath my sheets otherwise I would have ruined the mattress. It was that bad.
The man had to drink two gallons of water a day or he’d dehydrate. He wore these special gloves when we went out. We actually hooked up a couple times, did a semi FWB thing. But between the immature clingyness and the buckets of sweat, I just couldn’t do it anymore.
40. Sex was like giving birth
Slept with a guy who was both wide and long down there. Felt like I was giving birth trying to get it in. I mean Like it wasn’t all too bad. And he made me finish vaginally once, but dude was a stage 4 clinger.
Most girls didn’t want to stay with him because of his size. I didn’t want to stay with him because we got in stupid arguments and he was convinced he could “fix” my personality issues. Also tried to defend his ex for cheating on him when they were together because she was drunk.
41. Orgy after my LTR went wrong
It’s a tie, for me.
The first was at an orgy I went to after I got out of my last LTR. The group thing was winding down and one guy approached me to take it up stairs. This was my first “sexually liberated” experience, so I was like “eh, why the fuck not?”
Here’s why tf not: he was completely shitfaced, he was a smoker and a bad kisser, his dick was not to my liking, and he was obsessed with pleasing me to the point that it was kind of pathetic. Yes, I absolutely want a partner who cares that I’m having a good time, but if I tell you it ain’t happening, that’s your cue to finish and gtfo.
The lesson I took away from it is “Even at an orgy, you’re still allowed to have some standards.”
The other one I’m regretting more now that I’ve called it off. The sex wasn’t bad, but the guy was just boring as fuck and absurdly vanilla. I told him we were done and thought that would be the end of it. He tries to booty call me every couple of weeks even though I have made it clear each time that I’m not interested. It’s pretty annoying that he doesn’t seem to respect my boundaries.
42. He stole my beer
I hadn’t gotten laid in a year. I was really drunk at a St Patrick’s day celebration. I looked at a guy I knew and basically said “you”
Got to my place, had the worst sex ever, he left and took beers with him. Not worth it.
— 0hfuck
43. Confessed to masturbating to thoughts of me
I had just broken up with my ex boyfriend, who I had been with for 5 years. I hooked up with someone and this guy kept doing things around my house, cooking, cleaning, fixing shit. Turns out he had been into me for a while and confessed to masturbating to me one day when I had work a nice dress to class… I needed the emotional support but was too vulnerable not to keep putting out.
I even dated him for a few months until I came to my senses… yikes. My parents are so sweet and pretend it never happened, even though they met him a few times. I adore my current bf and that guy just feels like… a stain on my record basically, he is so embarrassing
44. Neurological damage lead to awful hookups
I had some awful hook ups to look back on after id been in a serious car accident. Whilst my face healed and my arm came out of the cast, i still had a bit of neurological damage. I shouldn’t have been going out anyway. Hooked up with an ex and then sent him home immediately which was pretty rude.
I also slept with this delinquent called Jonny who followed me around at parties and would just show up at my house randomly. He never had any money and had way more (long term) mental health problems than I did. He wrote terrible poetry. He had very bad breath and wouldn’t stop talking during sex it was really off putting. I was wasted both times we slept together.
All is well with me now thankfully but I ran into him on the street last yr and he’s still on the same path, ranting about the evils of capitalism and trying to stay with me cos he’s homeless. I gave him some money. He’s basically a good person but boy does it remind me of a bad phase in my own life.
45. Not ashamed of one night stands, but ashamed of this
Met a guy on OKCupid and things looked alright on paper. But when we met up for drinks he was really not for me. I don’t know why but I agreed to go to a second bar with him after the first, then took him home with me. Awkward sex ensued. He seemed to really like me. I did the, “yeah sure, we should do this again” thing when I was showing him to the door in the morning. Vivid recollection of how bright and sunny it was that morning too. Did not contact him after that.
I’m not ashamed of a one-night stand, but I am of my filter on that one. I think honestly that I wanted a one night stand so bad I took advantage of the opportunity. Now it’s stuck with me as a bit of a poor decision. Alas.
— Zyriel
46. Really bad temper
The pretty boy hothead that was terrible in bed and had a temper like a bull. XD oh what an asshole. I only slept with him twice (while super hammered) and one of the times i got bored and went to the bathroom to take pictures of myself for someone else XD
47. Got killed by doggy-style
Oh man, decided to hook up with this guy once while hanging with a bunch of friends. We went off into this walking closet and went at it. Very well endowed, I might add. It was really good and everything was going okay, we decided to switch positions. So fast forward to doggy style and I swear I’m pretty sure I died.
Everything was vaginal and it one quick second he slammed straight into my ass. I reallllly commend him on the accuracy…like he didn’t miss a beat with his thrusts and went straight in. I lost my breath and could barely talk but I managed to tell him to get it out. For some reason he was certain that I had done anal before (i had not). Regardless, his rather large dick was not something to just thrust into any vagina without warning. I hate him and we still laugh about it to this day.
48. WTF dude
The guy who gave me herpes. Womp womp
49. Got buttered up into sex
Not that bad, but a long time ago my friends hot older brother acted like he was really into me. He buttered me up like he was interested in a serious relationship (serious for HS).
After a very awkward hookup, he totally ghosted. I regret it because 1. I felt tricked and used 2. It occurred to me after the fact that I hurt my friend 3. Turns out, 10 years later, he’s a conservative Trump supporter who seems to hate women (according to his Facebook posts)
— Thomzzz
50. Ghosted him, but not too soon
This guy I had gone on 5 dates with. I wasn’t really feeling it by the 5th date but had too much to drink and decided going back to his was a great idea. I think he may have been a virgin.
Barely knew what he was doing and then came in 2 minutes. He called me a few times after and I ghosted him. In hindsight, I was a huge ass hole and wish I could apologize for my actions. But I felt 0 sexual chemistry and didn’t see the point in pursuing.
