1. There wasn’t ANY foreplay involved.
“I was a dumbass 16 year old, he was 24, so that’s regret right off the bat. No foreplay, he just yanked my legs apart and shoved it in dry. The worst part was not the porn groaning or the self congratulations (‘I bet you’ve never had a dick this big. I’m fucking huge. You like my huge dick, don’t you?’), it was that his dick was thin and seriously curved to the left. It felt like a blunt stick scratching the side of my already bone-dry vagina. I faked two orgasms to try to get him to hurry up and finish. After, he demanded a blow job because it wasn’t fair that I got off twice and he only got off once. Didn’t even have the courtesy to wipe it down first. I declined, stating that I had a broken, jagged tooth. He whined the entire drive back to my neighborhood, and I blocked him as soon as he drove off. He told the mutual friend that set us up that he wanted to marry me. I told the mutual friend to never set me up with anyone ever again.” — Haceldama
2. He never went down on me, but I had to go down on him.
“My ex whom I dated for seven years. He would never go down on me but wanted a blow job every single time and just HAD to ram his fingers in me while I gave him a blowjob. He would quickly fuck me until he came and then hop off and tell me to go wash up. We always needed lube for PIV and it wasn’t even remotely pleasurable for me. I thought I was the issue. Maybe I had a medical issue where sex just wasn’t pleasure and I didn’t get wet? Nope it was him. With my current boyfriend I sometimes get TOO wet and can cum multiple times in a session.” —
3. He didn’t wait for me to get wet.
“The one who was rather large and didn’t understand the concept of building up intensity. Just immediately entered and started jackhammering.
Ouch dude. So much ouch.” — proveitlikeatheorem
4. He had a big dick — but no idea what to do with it.
“He has a fairly large dick so before we got to business I was like hell yeah! And then he insisted on doing missionary and didn’t even thrust. He stuck his dick inside of me and pressed his pelvis against mine and moved his hips in small circles. The. Whole. Time. It was one of those instances where I wanted to show him porn bc he was THAT bad in bed.” — MackDaddyTayla
5. He kept complaining about the size of his penis.
“He had an average size dick but he kept complaining about how small he was, while fucking.
Boy: Oh but it’s so small I’m sure you can’t even feel it.
Me: Hey, no, I do.
Boy: You don’t need to lie about it, I know it’s small…
Me: It’s not! It’s fine!
Boy: No it isn’t fine….
10/10 would never fuck again.” — diskarte
6. He kept refusing to use a condom.
“The one that kept insisting on no condom (‘I will just get you plan B in the morning’), relented when I threatened to leave. Spat on my genitals. Started hitting a bowl when I was going down on him, didn’t offer me any. Then ‘oops the condom broke, but let’s go for 3 more rounds.’ (I think he ‘stealthed’ it, I was turned around when he put it on). I had never closed my legs so hard in my life. Wound up getting plan B in the morning anyway.” — throwitawaynow929
7. He only lasted for two minutes.
“He was too heavy for me to move at all and insisted on being on top, he lasted less than two minutes both times (lots of guys flop the first round so I was willing to try again) he was seriously lacking in girth but he could have salvaged that by engaging in foreplay and not giving me enormous hickeys, and not immediately getting up to check his online computer game. An rpg, he absolutely could have paused and just sat there for a minute.
He really wanted to meet up again too, like seriously? It was embarrassing. I’m embarrassed to remember it. I had never before had boring sex and I don’t plan on doing it again.” — kinkyquark
8. He made me bleed every time we had sex.
“My first boyfriend. I didn’t realize it at the time, but I was not physically attracted to him as much as I thought I was. I was never wet when we had sex, so every time he stuck his dick in me he would literally split my vagina open. I would bleed from the tear at the opening for the next two days. And during sex it was dry and painful, and I almost cried every time he suggested having sex… but I would do it to make him feel loved. Thought it was a medical condition for a while. Since I broke up with him I have had absolutely no problems like that – thank FUCK!” — BitchIsCharlie
9. The blowjob lasted for WAY too long.
“Met up with a guy off Tinder, we grabbed some food and a couple of beers and walked around the downtown area together. After, he offered to drive me back to my car.
Here it’s important to note that I had recently broken up with my long time boyfriend who had been my first, so I was only experienced with one dick.
We get to his car and start making out. I’m down, because we really hit it off on this date and I had fun talking to him. I’m feeling on his crotch area and I’m like, huh, maybe he’s just not turned on yet. I unzip his fly, start feeling around for a dick. What I find is a 2, maybe 3 inch (if I’m being generous) micropenis. He’s definitely already hard – I can feel it – but this dude is tiny and about the width of a single Twix bar. But I really don’t know how to tell this guy that I’m not digging it, because I’ve already pulled it out and I feel bad for turning him down this far in the game. So I figure, we won’t fuck but I’ll give him a blowjob. I used to pride myself on how good of blowjobs I used to give to my ex, seeing as how I had been the only girl to make him finish from a blowjob. I’m thinking to myself, this will be over quickly. NOPE. Idk if it was the beer, or if this guy just had the stamina of a porn star, but he lasted for like 40 minutes, which in dick-sucking time might as well be years. Sucking him off was like sucking one of those small lollipops you get at the doctor’s office – that’s how small he felt in my mouth. After he finally finishes he tells me, ‘Sorry, I don’t really like blowjobs but I didn’t really know how to tell you to stop.'” — LetThemEatBalut
10. He wouldn’t sleep with me unless I was completely shaved.
“I never made it around to sleep with him but when he found out I had a bush he gagged. Literally gagged. He was a 30 year old man.” — somecatgirl
11. He forced me to do all of the work.
“The first guy I’d ever been with. He was sweeter than sugar to me before sex, he even bought me chocolates. When it came time to have sex he seemed to turn very weird. He told me to get on top first because he ‘wasn’t going to do all the work.’ I got on top and he put it inside me but it hurt, so when he started thrusting I told him to stop. He did, but after a minute he said “are you just going to sit there?” I got off and told him to leave, which he did. He ended up telling all of our friends that we’d had sex and that for him it was like ‘fucking a mannequin.'” — UnluckyLight7
12. He didn’t make any noise at all.
“I was a sex worker at one point, so I’ve taken a LOT of dick. The most regrettable was my first paying client. Not cause I was ashamed or anything, but because he was so. Fucking. Weird. He paid me, got undressed, got on top of me, put his dick in, and…nothing. No movement. No noises. Just stared me dead in the eye until he came (I guess?) and left. I tried to move a couple times, but he looked down his nose at me like an old school marm, so I didn’t bother after that.” — Calamity_Thrives
13. The girth was way too big for me.
“A little preface I’ve only slept with 9 men and so this is a solid 1/3 of the dick I’ve gotten.
Dick #1 raped me.
Dick #2 like the girth of a soda can honestly don’t know how I fit him in me but it was not fun, didn’t help that his sweat dropped onto my face.
Dick #3 smelt SO gross like his whole dick reeked of like old cheese and his dick was like SOAKED like before even being inside me like he had buckets of pre-cum as soon as we were undressed.” — astralellie
14. He cried after sex was over.
“I don’t regret it, but I do feel bad about it: the tiny guy who blew his load before he fully entered me, and then cried in my arms. He’s an awesome dude though, and a great friend. I can’t help but cringe when I think about it; it wasn’t a proud moment for either of us.” — dedfishes
15. He kept copying what he’d seen in porn.
“An unexpected one-night stand. We went to a club with a group of friend, and we drank too much. I didn’t really know this guy, I just met him quickly a couple of times. We get back to our accommodation, I get off the lift, say goodnight to the group, get home, open my door, and I find this guy behind me, and he just grabs me and pushes me in the room. I was like what the fuck at beginning, but then horny drunk me was like ‘might as well enjoy it’. Oh boy, his dick was huge, but he watched too much porn apparently, cause he had no idea what fucking foreplay meant (and ya know, no foreplay, no lube, fucking hell), he was saying stuff like ‘you like this huh’ and trying position that just made no sense. I literally spent half the time in pain and the other half trying my best not to laugh in his face. At the end I just didn’t care enough, pushed him off, walked him to the door and said good night. The day after he knocked on my door and tried to hook up again, too bad for him I was sober.” — nosoulto_sell
16. His semen smelled absolutely disgusting.
“I don’t know what was wrong with him, but holy crap his semen stank. Legitimately smelled like rot and sent me gagging and retching. The encounter prior to that was also pretty bad, but it was like the disgusting icing on his already-awful-at-sex cake.
I still have no idea what was going on with that. The only thing I could think of was something related to the fact that he’d had a vasectomy.” — Liontamerr
17. His dick was weirdly shaped.
“More like regretting the person attached to the dick, but he did have a weird dick. Imagine a melted wax candle. Didn’t have any impact sex wise but it look really warped.” — faunlette
18. He did NOT know how to talk dirty to me.
“We start having sex and he starts trying to talk dirty to me in Spanish. I try to play along, but after a while (I don’t speak any Spanish at all, he knew this) I ask him if he can please talk in English so we can do it together. He says, ‘sure, sure,’ then looks me dead in the eye and goes, ‘…so you ever done anal?’
Got the fuck outta there muy rapido.” — suedeslayed
19. He was only interested in ONE sex position.
“He also exclusively only liked cowgirl… for 2.5 years… never again shivers.” — BitchIsCharlie
20. His dick was curved and painful.
“The actual guy was fine, forgettable really, but the dick itself was really long and curved up, so sex with him HURT. It weirdly felt like a sharp pain, like his dick was made of knives. I started referring to him as Knife-Dick and never slept with him again.” — Non_Dairy_Screamer
21. He claimed vaginas were disgusting.
“He called me disgusting and said that he wouldn’t ever go down on a girl/various things because vaginas are disgusting. I told him I wasn’t too comfortable with him saying that kinda thing as I’d been raped and he made me feel gross and uncomfortable calling me things like that. He laughed at me. Laughed. I told him to gtfo (this was after sex btw) and he started hysterically crying and got a severe nosebleed. He said he’d hang around near my house for a few hours in case I came to my senses. Once he was outside and my door was locked I told him to go away and never speak to me again.” — TheLittleCas
22. He gave me an STD.
“The one that gave me an STD.” — notwhoireallyam88
23. He was way too sweaty the entire time.
“I fucked a guy who was really sweaty all the time so whenever he was on top there would be this dangerous drop of sweat hanging off the tip of his nose. I never knew when it would fall and I was terrified of it going in my mouth.” — MrsOpiSafag
24. He started sucking on my toes.
“I met this guy on the bus. I invited him over to watch a movie and play board games. He brought a backpack, complete with sleeping bag. We’re watching movies and start making out, doing the thing. Start banging. I’ve got my legs up on his shoulders and he goes ‘wait.’ Pulls back and just licks my foot from heel to toe and then just pops my big toe in his mouth. And he’s thrusting and my toe’s in his mouth. And there’s this super intense eye contact. As he came he blurted out, “I love you!’ and ten minutes later he cried. Good guy besides the sex though, still sends me Facebook game requests.” — coffeeandcolor
25. He pressured me into having sex before I was ready.
“My first boyfriend. I was 15 and he pressured me into sex with him when I was not ready to lose my virginity. He also was very emotionally abusive and I wish I hadn’t let him pressure me into it after only a month of dating.” — lowkeydeadinside
26. His personality was horrible, which ruined everything.
“My first ever boyfriend turned out to be fucking MARRIED, which was both regret worthy and confusing, considering how long and how well I thought I knew him before I found out.” — Grizlatron