BAD SEX: 40 People Confess Their Most Cringeworthy, Godawful Experiences

Illustration by Daniella Urdinlaiz.
Illustration by Daniella Urdinlaiz.
Found on AskReddit.

1. There was just…not enough ass.

“My first attempt at anal. I’m 6’4″. My partner was 4’10”. There was just…not enough ass.”

2. I got anally raped by fire ants.

“One time my girlfriend and I were at my ranch in central Texas and we wanted to be spontaneous. So we decided to look around for a spot we could get it on out in the wilderness. We settled on this huge boulder in the middle of a creek under this beautiful array of Texas vegetation. So she is riding the shit out of me (cowgirl position) and all of a sudden I feel stinging on my ass. Turns out there was an ant pile in the crack of this boulder and the ants did not like the thought of my brown eye destroying their place of residence. I scream and throw my girlfriend off of me. By this time the ants have swarmed my nutsack and asshole and are terrorizing my nether region. I jump off the boulder into the creek and teabag the water furiously to rid the ants from my twig and berries. Finally I got all the ants off me, but the damage was done. Probably the most painful experience I have ever, had but I definitely had some satisfaction from getting to itch my dick for the next couple of days.

TL;DR Had sex on a boulder in the middle of the wilderness in Texas, got anally raped by fire ants.”

3. A 2-year-old has a bigger dick.

“Met this guy online but he didn’t have a picture. He was into kink and I (f) was just beginning so explore. I ask for a pic but he insists I’ll like what I see. So being horny and curious, I invited him over.

He’s average looking, and about 50 overweight. But I figured why not.

He ties me spread-eagle to the bed and gets a vibrator to tease me with. When I’m about to cum he tells me not to. OK, he’s Dom and into orgasm control, no biggie. So I start begging to cum. I’m absolutely desperate but he still says no. Ruined the orgasm completely. So I’m basically done but he wants a blowjob.

So he drops his pants and out pokes the tiniest penis I’ve ever seen. A 2-year-old has a bigger dick. I didn’t even know what to do. My lips alone covered the entire thing. I could not figure out how to make it work, so he tried to fuck me doggie. I don’t even think the head of his dick touched my labia. Weirdest and most awkward night ever.”

4. Her vagina smelled like a three-week-old dead CHUD mutant.

“The worst sex I ever had was when a girl had a bacterial infection that made her vagina smell like a three-week-old dead CHUD mutant. To this day I thank the forces of goodness that I didn’t try to go down on her because I’d probably still be in a coma if I had. I literally couldn’t do upward missionary or doggy style because the scent wafted up and made my eyes water, and at the time I was young and didn’t want to stop because I didn’t know how to tell her that her vagina was, to that point, the worst thing I had ever smelled.

I finally made it work by laying her on her side and coming in behind her while I partially muffled my own face in a pillow. When we were done I washed my dick in the shower for what seemed like hours.”

5. Her ex-boyfriend started banging on the car window.

“We were in my car after work near the woods. Halfway through, someone bangs on the window yelling, ‘What the fuck are you doing?’…It was her ex-boyfriend. He tried opening the door, but I had that shit locked. He just kept saying, ‘How could you do this to me? What are you doing? Who is he?’ she started crying and just kept saying ‘Leave me alone.’ He eventually left and I drove her home.

She told me that when she broke up with him, he refused to believe it and who tell her that ‘No, we are not breaking up. You just need more time to think about it.’ I knew he still had feelings for her, but I didn’t think he’d take it as far as stalking her after work….”

h3>6. Vag like a cavern, and she laid there like a dead fucking fish.

“There was this chick I’d known for a couple years. Attractive as hell, flirty, and (I thought) mutual attraction. Vag like a cavern, and she laid there like a dead fucking fish. Not a sound, not a single movement, nothing. I should have known something was off when she bragged to me about going on dates with guys purely for free food.”

7. Broke my banjo string, blood everywhere.

“Broke my banjo string, blood everywhere, hurt to get a hard-on for at least 2 weeks, need I say more?”

8. When she finally starts riding my face I realized she didn’t wipe well and the wetness from her pussy was mixing with the poop residue on her asshole.

“My girlfriend had been talking about how she wanted to ride my face so one night; we finally decide to do it. She wants to make a big thing of it so she puts on this sexy underwear and sets up a playlist and everything. When she finally starts riding my face I realized she didn’t wipe well and the wetness from her pussy was mixing with the poop residue on her asshole. The whole time it was like she was just rubbing a poop solution on my face. The smell and the taste was awful but I didn’t have the heart to say anything. I had her smell my face afterwards and she was mortified when she realized what happened. We’re married now and I tease her about it still.”

9. You should never let a man touch your vagina if there’s even the slightest chance he could have hot sauce on his hands.

“Let’s just say that you should never let a man touch your vagina if there’s even the slightest chance he could have hot sauce on his hands.”

10. Immediate, boner-crushing pain.

“Was doing the sex, her on top. She got a little too rough and it bent. Immediate, boner-crushing pain. She said ‘Oops!’ and tried to keep going. I had to get her off of me, then she got mad at me and said that if we couldn’t have sex, she’d just leave. Which is exactly what she did. She didn’t understand why I refused to speak to her again.”

11. I was conscious that we were having sex but still dreaming I was at a deli counter.

“An ex and I were taking a nap when we started having sex…I was conscious that we were having sex but still dreaming I was at a deli counter. When all was said and done we looked at each other slightly disgusted and agreed to never do that again.”

12. I don’t mind a bit of bush, but this thing was denser than the Amazon forest.

“OKCupid date. After a few drinks she went down on me, then it was my turn. Now I don’t mind a bit of bush, but this thing was denser than the Amazon forest. Also sex was like trying to hump a rock that was forever changing into awkward positions. Eventually I faked an orgasm by pulling out making some noise and spitting on her back. 1/10 we never spoke again.”

13. She reached toward the top of my ass crack and removed what was left of a red Skittle.

“My roommate in college was a total slob, but that didn’t keep me and this girl from getting it on in the general living area while he was away. We were on the easy chair and she was on top, so things got pretty sweaty.

We then moved to the couch for some doggy to air it out. Awesome. Until I look down to notice red dribbling down my leg. My thought was that she had just downloaded Spotify on me, which wouldn’t be the first time.

I pulled away and with a non-judgmental tone conveyed the situation to her. Her face was puzzled. We looked on the chair and saw a red streak and she investigated herself. Her words “It’s not coming from ME” took a while to rattle around my skull. ‘Well it sure as he’ll isn’t coming from ME!’ I retorted.

I turned toward back toward the chair and she started bursting with laughter. With a brave hand, she reached toward the top of my ass crack and removed what was left of a red Skittle. To say the least, it was very difficult to overcome the nickname of ‘Skittlebutt’.”

14. When I got to his dick it was incredibly small.

“It was my birthday, I was drunk and wanted to have some birthday sex, so I texted this guy I’ve been talking to. Went to his house, we fooled around for a bit and when I got to his dick it was incredibly small…I was very disappointed because he’s a huge dude but his little friend is really little. Tried to get it inside a couple times didn’t happen, gave him a BJ he came, I patted his belly and fell asleep…Happy birthday me!”

15. Every inch of him was covered in needle-like stubble.

“I got a disclaimer from him right off the bat: ‘It’s been a while.’ But that wasn’t even the problem. He shaved his entire body and was just starting to grow back. Being a hairy fella, every inch of him was covered in needle-like stubble. Thank God ‘it had been a while’ for him, because if it was any longer than the 20 seconds it was, I would have been bloody all over my body from his stubble rubbing against me.”

16. Right in the middle she’ll say something like, ‘By the way my parents wanted to know if we’re free this weekend’ or ‘Did you remember to fix the washer?’

“My wife is a notorious pecker wrecker. Right in the middle she’ll say something like, ‘By the way my parents wanted to know if we’re free this weekend’ or ‘Did you remember to fix the washer?’ I’ll usually stop and ask if we can discuss it at another time.”

17. He thought my asthma attack was an orgasm.

“I had an asthma attack midway through sex with some random dude (I’m a woman). He was on top in missionary and I started gasping and trying to push him off me so I could get my inhaler. He starts saying, ‘oh you like that?’ and went harder. He thought I was cumming. I was not.”

18. She refused to touch my dick.

“First girlfriend in high school that I had sex with. She was bisexual but I thought she might just be a lesbian. Most times she would literally just lay on her back and not move. She refused to touch my dick. 90% of the time I couldn’t even cum. The first time I did cum, in a condom, she panicked and told her parents that she thought she was pregnant. Relationship didn’t last much longer.”

19. She broke my penis.

“The classic pull back, thrust forward, and bend. Could not get back in the mood after that pain.”

20. I came in like 30 seconds.

“More just embarrassing than anything, but my girlfriend had been teasing me all day by touching me, but never going further than that. By the end of the day she’s all excited thinking it will be great sex with all of the build-up, but I feel like I could burst just thinking about it. Came in like 30 seconds :(”

21. Guy with huge, awesome penis came before even thrusting once.

“Guy with huge, awesome, penis put it in me, never thrusted once, then pulled out immediately and came. Wouldn’t have been so terrible if he at least went down on me.”

22. She asks with the most condescending and bored tone, ‘Are you done yet?’

“So freshman year of college and I’m a virgin. My first girlfriend in college was actually the cutest girl I’ve dated. We start messing around and she wanted to move fast, which is fine by me, I’m wearing this v-card like a scarlet letter. We start having sex and she’s like, ‘OK, so you can’t make me cum, so just let me do my thing for a minute and get off, then I’ll do you, and we’ll both be happy.’ I’m thinking is sex supposed to be so formal? Whatever, let’s do it.

One minute in, she forces me to sit still as she gyrates on my dick, with this intent look on her face like she’s internally trying to fit the square peg to the square hole, and then she gets off. Then, once finished, she clenches her vagina on my dick super hard and brags how she used to get her boyfriends off so fast, so I’ll be done in like a minute.

I acted like I was. This is how sex goes every time. I literally thought sex was just so shitty. One time I got drunk and was like, ‘Fuck it I’m gonna take her to pound town’ and take control and we bang for like 30 minutes nonstop, and I feel like a freaking porn star. She doesn’t make a noise, and when I stop breathless, she asks with the most condescending and bored tone, ‘Are you done yet?’ I meekly mutter ‘Yes,’ and she gets on top, does her voodoo rain dance on my dick for 30 seconds, gets off, and goes to bed. This was the 1st and only time I’ve broken up with a woman because of sex. Which is shitty because she was an amazing girl except for that specific thing, which is huge sadly.”

23. I lost my virginity to a girl who was 9.5 months pregnant.

“I lost my virginity to a girl who was 9.5 months pregnant. She was induced the next week. She had been a stripper when I met her through mutual friends. Kept hanging out with those friends and she was always around. One day our mutual friends made up an excuse to leave us alone. We were watching Squidbillies and she jumped me. My dick was numb the entire time. She got off in about 3 minutes and then it was over.”

24. Her pussy tasted salty and sweaty, and I didn’t even cum.

“Time I lost my virginity. My roommate was in the room watching Netflix, I barely knew the girl, her pussy tasted salty and sweaty, when my roommate finished watching Netflix and tried to sleep he yelled at us and told us to go to sleep after groaning for 30 minutes. And I didn’t even cum. 2/10.”

25. I came into my own fucking face.

“It was a cloudy December afternoon a few years back, an old high school acquaintance and I decided to have lunch after randomly running into each other at a bar a week before and had a good time.

We decided on Mexican food (this story is not about shit). She had shrimp ceviche, I had some spicy cactus type shit. Twas good. We go back to her apartment and start watching Louie, get about 5 minutes into an episode and decide to just go for it. Here’s how it went.

She would not let me take the blanket off of the top of me, I had drank a little the night before so I was sweating BUCKETS on this girl. Like this shit was comical. Her shrimp ceviche breath was not the biggest turn-on…though I’m sure I smelled wonderful, too.

It was pretty vanilla sex and I just wasn’t into it. After about 30 minutes of thrusting and sweating, I decided to just have her jerk me off. Well that sucked too, so I just said, ‘Lemme do it.’

So I’m viciously beating off with this chick sitting next to me just watching. I finally get off and as if this experience couldn’t have been worse: I come…into my own. fucking. face. I was done after that and made up some shitty excuse to go home after we smoked a cigarette in her room. There’s no telling what she told (if she told) her friends about it. I still lose sleep over that shit.”

26. I tied her up, then she started crying.

“Bought some really expensive leather wrist and ankle restraints for my GF, we have tied up before and she was really into it. We strapped her down and started getting freaky. Then out of nowhere she starts crying and shit…like REALLY upset. Turns out she hates being tied up and was just playing along before cause she wanted to make me happy. Worst feeling ever.”

27. I spent the night with a passed-out pussy on my face.

“Ah yes…the good old days. I was but a young freshman in college, and upon finding out the girl I had lost my virginity to six months prior was cheating on me, I did some silly things. After about a week of drinking with the roommate and trying to get out of the funk, I met a girl two floors down; recently dumped, also drinking alone, and we just clicked. Looking back it was obviously the alcohol, but I thought she was great. We keep drinking together, and at some point my roommate goes to bed, so we head down to her room. Very drunk at this point, although she was much more than I. She starts to make out with me, I notice there is much more to tongue and saliva than I’m used to. I forge ahead, excited. She suggests we get in bed, I agree, happily. Then I notice she has a lofted bed. The kind where you put a couch or desk underneath, and then sleep on the top bunk. So we get up there, and there is not much room. Maybe a foot and a half to the ceiling. So we get naked and handsy. She is very drunk. Then she says she wants to 69. I agree, although I had reservations; I had never done it before. She, with not a little difficulty, flips around and mounts me. Not two minutes in, her head stops moving. I stop and listen, and she’s snoring in the strangest way. Almost like she had a dick in her mouth and had fallen asleep on it. So I tap her shoulder, say her name. Nothing. Then I lift her head off of my rapidly flaccidating penis, being careful of the ceiling. Then, I attempt to remove myself from beneath her sleeping loins. Now, here’s the thing. I wasn’t a small guy, I worked out and such. Not huge but not tiny. And she was average size, but a runner. She had very large legs. So when I went to lift her, she hit the ceiling. And I couldn’t get enough clearance to get out from under her. I ended up sleeping the until she woke up, which was 9 hours later.

Tldr: I spent the night with a passed-out pussy on my face.”

28. And then the smell happened.

“I dated this girl that I’d known for several years already. She was really cute and one of the funniest people I’d met. I always had a crush on her in college but was in a relationship, so once we were both single I was really excited to ask her out. Our first date was amazing until I walked her home and kissed her goodnight. I’m not sure how to put this except to say that she just didn’t know how to do it. It was like she’d never kissed a person before. She’d kind of hold her closed lips against my mouth, and then with a quick, almost predatory motion, open her mouth stick out her tongue and then snap her mouth closed again. It was like a lizard catching flies. ‘Well,’ I thought, ‘this is gonna be interesting to deal with.’

So we keep seeing one another for another week or two. I really, really like her. She really, really likes me. The physical attraction is there, but every time we make out it’s like there’s a guppy on my face. Eventually I found that if I kind of held her tight and slowly kissed her like a normal person, she’d follow my lead. Things go that way for a couple of nights, and then, at a party and after about a week and half or so of dating, she asks me to spend the night at her place.

We get to her apartment and things immediately get going. We’re up against the front door and she’s doing her lizard mouth thing, and I’m sort of correcting her until things are working. It was like in a movie where people undress one another as they walk to the bedroom. Her shirt was by the front door, mine on a chair, shoes kicked to four different corners of the hallway, pants thrown across an end table, skirt ends up in the kitchen somehow. She had the most amazing breasts I’ve ever seen, to this day. And then I go to take her panties off.

Now, it’s worth mentioning that this girl wasn’t extremely sexual. We’d made out a lot but nothing under the pants had happened yet, so I was totally unfamiliar with her vagina. So I take her panties off, and out sprouts the largest bush I have ever seen. And I’ve been with women who were shaved bald and women who liked to keep a lot of hair on and everything in between. This was a completely unkempt, un-manicured, never-once-in-twenty-seven-years-been-trimmed thicket of hair. ‘Well,’ I thought, ‘this is gonna be interesting to deal with.’

I dutifully start making my way down to start giving her oral, and she mercifully stops me at around her navel and says I don’t have to because she isn’t really into that. I say a Thank You prayer and we get into the main event. It went how I should’ve known it would. A lot of thrusting into me when I was pulling away from her and vice-versa so that there was no actual friction. Then, after a few minutes, she starts moving beneath me at a totally different rhythm. I figure she’s trying to get me to go faster so I try matching her pace but every time I do, she changes or keeps her hips pressed against mine.

And then the smell happened.

It wasn’t the typical kind of overpowering awful vaginal smell people talk about, but it was just strong enough to be impossible to ignore. At this point, I start to lose my erection and spend the next fifteen minutes trying to keep my windsocked penis from falling out of her. She’s silent the whole time, by the way. I keep checking in with her and she keeps saying ‘This is great, keep going.’ Finally, out of nowhere, she looks at me and says ‘I came three times already, you can finish.’ I tell her I won’t be able to.

Anyway, we went out once more, didn’t go home together, and then she stopped returning my calls. Found out through a mutual friend that she told some people that she really liked me, but there was no sexual chemistry.

tl;dr A really beautiful woman didn’t know how to kiss, groom, or bang. Dumped me for not knowing how to kiss or bang.”

29. She started rapping to my dick.

“Oh god OK. So there was this girl I met on OKCupid. Hipster/punk chick. Liberal, friendly, SJW type that worked on an organic farm during the week. My type. Plus she wasn’t looking for a relationship, only to fuck. Sweet.

Anyway she comes over, we smoke a bit, she’s exactly as she represented on the Internet. So we finally go to my bed (showed up without a bra or panties on in a skirt) and she asks me to go down on her. I’m always the type to oblige this so I do.

With this type of girl you might guess that she was the kind that doesn’t use a razor anywhere for the purposes of making a statement. You’d be right. But whatever, I’m not prejudiced. My only issue was that her pussy smelled strong. Not like bad, just the way vaginas are supposed to smell but a lot more of it. So I sucked tangy carpet ’til she came the first time. Whoopee.

Then we had sex. You’d think a girl this sex-positive and otherwise a member of this social archetype would be good at sex. Nope. Fuckin’ starfish. Wouldn’t even angle her body properly so I could get better penetration. She was enjoying herself but I wasn’t. Asked her to flip over so I could fuck her from behind. She responded that she didn’t feel like it. sigh

She did however get on top, and did that crappy grinding that does fuck all for the dude. She came again, my dick felt numb in the condom. I asked her if she could finish me off with her mouth, and she said yeah. I’m wondering if she could possibly fuck up a blowjob.

Well, she did.

She literally just put the head of my dick in her mouth and sucked on it. No head bobbing motion or anything, just sucked it as you would a lollipop with less tongue. I convinced her to use her hand in conjunction with her mouth. That helped bring me marginally closer to orgasm. Then I told her to talk dirty to me…

She pulled her mouth off my dick and responded that she doesn’t know how to talk dirty very well but that she can rap. Before I can say “uhhhh” in response, she launches into a rap (more of a nursery rhyme tbh) about giving head and sitting on dick) by the time she was done I was flaccid. I told her I’d finished despite the evidence to the contrary. We shared a few more cigarettes and she left with my first two volumes of Y: The Last Man, because I figured she’d be into its feminist themes.”

30. I never imagined having a half-chub trying to stab this poor girl while a rock dug into her back.

“Worst sex I’ve ever had hands0down was with my current girlfriend the second time we went out. Went on a hike, it was raining. Got into it on top of a mountain. I’d imagined it would be thrilling and badass. I never imagined having a half-chub trying to stab this poor girl while a rock dug into her back. We were both shivering and tired after that yet she’s stuck around for 3 years and much better sex.”

31. Seriously, there could’ve been one good stroke possibly?

“He entered me and immediately came. Seriously, there could’ve been one good stroke possibly? Wasn’t worth it.


The guy who jackhammered me all night. Gave me no sort of pleasure outside of putting his dick in me. He was just looking at himself in the mirror American Psycho style. I was bored as fuck. I guess that’s what I get for taking home a go-go dancer. I wanna end this by saying that there is a happy pleasurable medium but these guys did not have it.”

32. She was pulling on my dick like she was trying to start a lawnmower.

“I had a girl give me a blowjob one time and she was using her hand to fill in the gaps of time that her mouth wasn’t on my junk. The problem was that she was pulling on my dick like she was trying to start a lawnmower and it was incredibly painful.”

33. He starts to fuck my feet with his cold, wet, flaccid penis.

“I have a story. Prepare yourself. My marriage ended for a lot of reasons, but the ‘sex’ was beyond bad. The details aren’t important. I tell people we were incompatible although I would wager the kind of woman he needs sexually doesn’t exist outside of a paid studio acting job.

So one night he comes home. He knows I am thinking about leaving him. He initiates intercourse with me for maybe the first time in 7 years. We are upstairs, he can’t get it up, I flip over, he wants to try and do me doggy. So I’m on all fours and he grabs my feet and pushes them together and starts to fuck them with his cold, wet, flaccid penis. And he still can’t get it up. Then he left and went to the bathroom to jack himself off.

And that, ladies and gentlemen, is why I am a very happy divorcee.”

34. I put my pants on and tell her, ‘Go do your fucking chores,’ and I leave.

“So I had my first kiss and lost my virginity all within about an hour when I was 13 years old.

I was in middle school; there was this girl who was I guess was considered by all to be very promiscuous or whatever. Anyways, one day at school I get her phone number and we start texting. A few days later she texts me, tells me her mom isn’t home, and says I should come over. I’m super-nervous because I can tell where this is leading, but I head over.

Anyways, I get there and the first thing she says to me when she lets me in is, ‘Wow, you’re the first guy who has come over who hasn’t started making out with me immediately.’ I’m super-flustered by this and just awkwardly laugh it off. Then we head up to her room and I sit by her computer. She tells me that her computer isn’t working, and I know nothing about computers, but I say, ‘Oh, I can fix it.’ So for about what seemed like an hour I attempt to ‘fix’ her computer, which probably just looked something like me opening and closing Microsoft Paint the entire time until I give up and admit defeat to her. Also, during that time, her mom had called and reminded her to get her chores for the day—this becomes relevant later.

So then she kinda scoots over on the bed, invites me to sit next to her, which I do and she starts going down on me. For literally like 5 seconds. Then she says, ‘If you want more, you have to be nice to me.’ And I’m like, ‘Uh… be nice to you?’ … ‘You have to make out with me,’ she says. Again, I’m super-flustered, especially because I have never kissed nor made out with a girl and I’m terrified of being found out as an inexperienced and likely terrible kisser. So I tell her, ‘I don’t make out with girls, I just have sex.’

That doesn’t work and so I go downstairs and start watching Laguna Beach or The Hills or something. I start dozing off, but I remember seeing her walk down the stairs in her underwear. Then all of a sudden I feel this fat tongue in my mouth which really startles me, and I kinda wanna back away, but then I’m like, all right here’s my chance to have sex. So I go to pull her underwear down, at which point she stops me, pulls her underwear to the side slightly, and says, ‘This is what prostitutes do to make it legal.’

Obviously, I’m a little taken aback by this comment but I roll with it. I take my pants off, but not my underwear. And I pull my phone out. I had this shitty flip phone at the time that you could leave open at a 90-degree angle, so I set it on the table and recorded us having sex. And while we have sex, I never stopped making out with her, and it was terrible, my face was just covered in saliva, I don’t even know how it happened in retrospect. Essentially it looked like two people conjoined at the head having awful, confused sex.

Now it’s worth mentioning that I had also never masturbated at this point. I didn’t even really know what ejaculation was. So I continue to have sex with her for maybe a minute or two, until I decide alright, that’s sex, I did it, and pull out. Then I think, I gotta come up with a cool one-liner or something. I put my pants on and tell her, ‘Go do your fucking chores,’ and I leave.

And that’s how I lost my virginity.”

35. That chick was perfect except for the surprise sodomy.

“Ahh the story few people in my real life know about. I had a GF who was really into anal and I’m not so much into it. Especially when it comes to me getting something up my ass. We’ve been dating for about a month when she tried the old finger up the tailpipe while blowing me. I jumped straight up on reflex and accidentally deep-throated the poor girl and she vomited on me. So I had mixed emotions between feeling violated, pissed off, disgusted, embarrassed, and sorry for everything that just happened in less than five seconds.

We had a talk and I told her that my back door was a no-go zone and I’m also not into spelunking no matter who was receiving. So I thought that was the end of it.

That was until about another month goes by and we’re going at it again and she tried to shove a dildo up my ass. at least this time she wasn’t blowing me at the time and I flew off the bed and into the wall while screaming No, No, No in a very feminine high-pitched squeal. For some reason that chick was very into anal and I didn’t trust her enough not to try to shove something up my ass, so we broke up. It’s too bad. That chick was perfect except for the surprise sodomy.”

36. Her thumb was fully inside me and I released my clenched sphincter to allow the deep rumbling liquid hell forth.

“Buckle up, guys, because you’re in for a story.

Several years ago, seeing a local girl and she’s at my place, lovely evening moves on to some light kissing, some touching, and pretty soon we’re naked, Im lying back on my bed, she’s down using her mouth on me.

Now being the gentleman that I am, I am focused on holding in a fart. I could leave and head to the bathroom, but she’s seriously good so, I’m just putting all my energy on keeping that fart inside me. Nothing too difficult, I can handle this if i keep my attention away from how great her mouth feels and focus on keeping my arse shut.

After a while of fantastic tongue action, she looks up at me from between my legs and says: ‘Dont worry.’

Now up until now I hadn’t been worried at all. I was enjoying this evening, I was fully aware of the situation, and I had absolutely no cause to worry about anything. BUT, now she’d told me not to worry, i started worrying, I started worrying a lot. what was she into…

Now, what I would LIKE to say happened next is this: she gently eased a VERY WELL lubricated thumb slowly inside my back passage, while keeping me in her mouth, and treated me with care and dignity.

That did not happen.

This happened…

She said, ‘Don’t worry,’ I started worrying, and then within a second, she rammed her thumb up my arse. Deep and dry, it felt like sandpaper being parted by a cheese grater. The shock of having a thumb forced inside me with the force of a thousand suns caused several things to happen: one I screamed, two I half sat up, and third and possibly worst, i released the fart i was holding…

Which was not, as she suddenly discovered, a dry one.

Her thumb was fully inside me and I released my clenched sphincter to allow the deep rumbling liquid hell forth.

Picture what happens to the water when you put your thumb over the end of a hose pipe and spray it into the air, then replace water with shart, hosepipe with my arse, and the air with her face.

She, understandably, jerked hard backward from the brown spray; however, in doing this, she pulled her thumb straight back out of me, i clenched harder than a camel’s eye in a sandstorm, and then for SOME REASON…came.
She screamed, ran to the bathroom, and turned the shower on. I fell back onto my pillow smelling of sweat, sh*t and cum.

We don’t talk anymore.”

37. As soon as I got my face down there…I puked all over her!

“Back in high school I dated a girl (later turned out I’m gay, she was a lesbian). During many sexual episodes she would go down on me and give me a blow-job. She kept asking me to go down on her, but, ya know, the gay-part-of-me wanted nothing to do with it. But, at one point I finally gave in and went down on her. As soon as I got my face down there…I puked all over her! This was like projectile vomiting all over her crotch, legs, belly, etc. So much for str8-high-school-sex!”

38. I look over my shoulder and there is a guy in a van with a huge grin on his face watching us.

“I was with my girlfriend when we were 16 and we needed a place to go have sex, so we used my car. We drove into a very secluded and windy road with trees all over and pulled over. We are going at it and everything is fine until I look over my shoulder and there is a guy in a van with a huge grin on his face watching us. He then yells, ‘If she ain’t sucking your dick it ain’t worth it!’ before taking off. It was terrifying at first but immediately became funny afterwards.”

39. Not even 10 seconds into the handjob, he cums.

“My first attempt at sex, after leaving my boyfriend of 5 years, was with a close friend. I had found out my boyfriend had been cheating on me, for almost a year, and while I tried to work it out with him, I couldn’t. That being said, I hadn’t had good sex in months. So I go to my friend’s house, and start flirting, hard. There had always been a good deal of sexual tension between us, and I couldn’t wait to sleep wth him. We start making out, heavy petting, and then clothes start coming off. I’m hornier than I had ever been. I take my bra off and start to initiate foreplay, but it doesn’t go as planned. Not even 10 seconds into the handjob, he cums, it gets all over my bra and shirt that are laying on the bed. I laughed a little, in an attempt to lighten the mood, but he got too embarrassed and wouldn’t give it another shot. I left, frustrated and sticky.”

40. I slept with a man who had a micropenis, but his size wasn’t why it was terrible.

“I slept with a man who had a micropenis, but his size wasn’t why it was terrible.

He said ‘Oh my God, you’re so hot’ when I took my shirt off, and ‘I’m sorry my penis is so small’ when he took off his boxers. I reassured him how I could, but when we started having sex, he repeated those two phrases ad infinitum. It made me feel really uncomfortable. Afterwards, he cried. Turns out he had a pregnant wife. (I’d known this guy for 2-3 years at that point and had no idea he was married.)

If it were merely his size, it may have been a forgettable experience. Apologizing for it only called attention to it. Telling me I’m hot was flattering the first time but weird following. The pregnant wife thing was just fucking terrible. It was clear he’d avoided talking about her around me. I didn’t want to be trouble, and he obviously regretted it.” Thought Catalog Logo Mark

About the author

Lorenzo Jensen III

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