25 People Reveal Their Most Awkward Sexual Encounters

27 min read
25 People Reveal Their Most Awkward Sexual Encounters

Whether first or old timers, every sexual encounter has to make you feel good, but sometimes, some people are so good at being insane, it has gone mad!

We know how special sex is (unless you do it for fun), but when you’re about to have sex or in the middle of it, nothing (and I mean, nothing) should be distracting the moment. But, we have to admit it, there are times when just as when you are about to have the greatest moment of your life, someone or something, will help you lose it. Darn!

Well, you’re not alone because these Reddit users sure did have one helluva time…literally in hell. So, if you think yours was worse, wait ’til you read theirs — some weird, freaky, hilarious, but all downright awkward. Read on!

Some entries have been edited for clarity, spelling, and grammar.

1. “…mmm you taste like potato chips.”

“Back in college, this girl came over to my dorm to Netflix and chill. It was going well and we had plenty of snacks to eat. After a while, things start to get a little frisky and I slide down to eat her out. She’s having a good time, I’m having a good time, everything’s going great. But then out of my stupid f*cking mouth comes the words: “mmm you taste like potato chips.” We’re both just stunned for a second at how I could say something so stupid. She buries her face in her hands and goes “Oh my god that is such a turn off.” She’s about to get off me so the only thing I can think to do is to shove my tongue back in her. Surprisingly, it worked but for the rest of the night, I knew that’s all either of us were really thinking about. This is how I learned to keep my mouth shut during sex.”

giphy | Stay at Home

2. “…got my balls stuck in a Gatorade bottle.”

“One time, I got my balls stuck in a Gatorade bottle.”

3. “…he brought a Ziplock baggie to catch the cum so it didn’t get all over his pants.”

“I was dating a guy and he would always jizz in his pants while making out. That’s not that big a deal on its own, but one time, he brought a Ziplock baggie to catch the cum so it didn’t get all over his pants. He also seemed to think that the goal of French kissing was to lick the other person’s tonsils and mash faces as much as possible. Looking back, that whole relationship makes me cringe, partially because we were awful about PDA. Once, we made out while sitting on our friends’ laps and they were trapped under us. It was not a kind thing to do.

Edit: I realize now with all the questions that I should be a bit more clear. There was small amount of over the clothes action that would occur during more private make out sessions that did not occur the one time we were piled on a couch with our friends so it was unlikely he came while we made out on our friends.

We were in high school and hormonal in a fairly religious community and he had never had a girl touch his penis before, even over the pants, so there was a lot going on there for him. After the first couple of times, he brought along a plastic bag because it’s hard to buy condoms in a small religious town without someone who knows your mom noticing. Lunch bags are easily accessible and less suspicious.”

4. “Banged a guy from rehab on my just-deceased mom’s bed…”

“Banged a guy from rehab on my just-deceased mom’s bed when we were supposed to be cleaning and looking for important documents.”

giphy kjk | Stay at Home

5. “I once had sex with a bigger guy I was dating in his pool…and he had the smallest penis I had ever seen.”

“I once had sex with a bigger guy I was dating in his pool in the middle of the night and he had the smallest penis I had ever seen. It was our first time having sex and it was the worst. I was pretty tiny (both height and weight) and he was very large and he kind of had to like pin me to the side of the pool and he kept trying to put it in but it just was not working. So he was humping me and basically turning the pool into a wave pool, water was splashing onto my face and he was making horrible grunting noises while I kind of had to just stay there pinned with these damn waves crashing into me and his body smashing mine with no actual penetration. I thought this was all awkward enough until after he finally started to give up, I looked back into his house to see his friend, who I thought was asleep, masturbating on the couch watching this goddamn nightmare go down.

Hands down the worst “sex” of my life. We didn’t date very long…

Edit: Jesus Christ, here is my obligatory “of course this is now my highest rated comment”. Yes, I am aware pools can make dudes weenies seem smaller but it was a micro penis all the time. Yes, I could have told him he sucked but I was young and felt uncomfortable doing so because he wasn’t always the nicest dude.

Also for all those asking he was big like fat not body builder.”

6. “…she believed she was a vampire.”

“Wait a few dates before having a blow job. Why? I was getting my first blow job from my girlfriend at the time and she was a bit goth and moody and sh*t. I didn’t know she was into pain play too. Found out when she bit down really hard as I was pulling out and dragged her incisors on my d*ck and ripped it up. She was way too into it and started licking up the blood. I had the most confused orgasm I have ever had in my life. Then I had a lot of pain and cried for about 15 minutes as she tried to bandage it up and told me to “suck it up, it isn’t that bad.” She explained that she believed she was a vampire. I told her that I believed she was my ex as well, dropped her back off at school, and never talked to her again.

Always get to know them first. Always.”

7. “Got the tip of my junk caught in the brace bar behind her teeth.”

“Got the tip of my junk caught in the brace bar behind her teeth. She was struggling to pull away which hurt so I was trying to stop her… we ended up calling her dad for help. He brought me a cup of ice and a warning to never come back. I did not.

Have a small scar to this day lol.

Edit 1: By request more bad stories! The night I lost my virginity… took a lovely waitress back to my place after her shift was over. Complete dead fish. I was hugely disappointed. In the morning, I think to myself maybe she was tired, lets try again! Start messing around and she’s already wet so I go to get on top and that’s when I realize she’s not wet. She had started her period on extra heavy flow. It had been seeping into my mattress all night. Had to pay the dorm manager to replace it.

giphy 1 | Stay at Home

8. “I literally had to text my mum asking her where the condoms were…”

“When I was a teenager my mum knew I was having sex with my girlfriend. She was like, “you need to make sure you are wearing a condom.” Which was awkward enough by itself, but then she was like ‘I bought some for you, they are in the bathroom.’ F*ck me, cringe through the roof.

Then one day, my girlfriend and I were home alone. Went looking for mum’s condoms, and couldn’t find them anywhere. So I literally had to text my mum asking her where the condoms were, so I could then proceed to bone my girlfriend. She replied instantly that they were in the bathroom under the sink. Except that they weren’t. So I didn’t get boned AND it was super cringey having to ask my mum that question.

To make things extra spicy cringy, we later found out that my little brother had been using them to masturbate, which is why they weren’t in the bathroom.”


“I had a boy over after an excellent date. It was obvious sex was on the agenda, so he comes back to my place, under the guise that I have a “really nice TV”.

Commence TV watching. We watched The Office. We started making out. He started going down to clam town. In the middle of dining, he said enthusiastically, “Wow, it’s really sexy that we are doing this to The Office.” Meanwhile, Michael Scott is basically staring at this boy’s ass through the TV behind him. It was not sexy, but maybe he had meant it as a joke, despite the look that he’d had on his face. So I let it slide.

And it wasn’t long before he was in position to, as he had said, “f*ck my brains out”. He started thrusting, and as you may have predicted, the noodle was limp. That doesn’t stop him from thrusting his hips wildly, hoping that perhaps his d*ck would follow suit if he faked it enough. But alas, it was not to be. So he flipped me over, in the hopes that a glimpse of the full moon might trigger a response. Still nothing. I am flipped back over and after a few more minutes of what is essentially just pantomiming sex. And then, abruptly, he stops. He sits straight up, a look on his face that appears to convey that he knows now what he must do to harden his penis. He jumps to his feet and shouts, “I HAVE TO CALL MY MOM!” and sprints out of the room, leaving me naked and incredibly concerned.

Hearing his mother’s voice did not harden his penis. He left later that evening without actually ever getting himself into my vagina. He claimed the call to his mother was not in the hopes that her voice would arouse him. I am not sure I believe him.”

10. “I’m trying to have sex with each letter of the alphabet.”

“This was probably 4 months ago. I ended up getting back in touch with a female friend from high school. She kinda messaged me out of the blue randomly, but whatever, I haven’t talked to her since we graduated together about 3 years ago, so I figured it would be cool to catch up. Eventually, one day, she asked if I wanted to hang at her apartment after I get off work, I was like sure why not. So after work, I show up and she asks what movie I wanna watch, I go through her movies and we decide on one. We get into random convos about where we are in life and sh*t like that. I had just started going to the gym so I told her I was still sore from yesterday’s workout. She told me to take my shirt off so she could give me a massage. I’m like… oh? Okay. I don’t know if this is going somewhere but even if it’s not, my body is still sore and needs a massage so why not.

So I get half nude as she requests and she gave me the massage. One thing led to another and we eventually had sex.

Here’s the kicker:

Immediately afterwards, she pulls out her phone and opens the “notes” app. There’s a giant list of names on the list and she’s typing, I’m like “Oh? What’s that?” And she was straight up and said “Oh so I’m trying to have sex with each letter of the alphabet. I didn’t have a T in my list yet, so now I can finally add a T!”

About an hour after all of this, she was like “Yeah well I gotta be up early tomorrow so I’m gonna have to kick you out”

I wasn’t mad or disappointed. Still had sex. But I still feel that was awkward as f*ck. She never messaged me again after that either.”

giphy 2 | Stay at Home

11. “I have narcolepsy, so I tend to fall asleep at inappropriate times…”

“I was at a party with my then ex-gf in high school. Both of us are pretty drunk and she wants to have sex, so we go to the upstairs bathroom, lock the door, and turn off the lights. I lie on the floor, no condom, and she proceeds to ride me. I have narcolepsy, so I tend to fall asleep at inappropriate times… this being one of those times. I fell asleep for who knows how long. I wake up to the sudden urge to cum, I yell “GET OFF”, push her off me, she hits her head on the counter, and I cum all over myself… sad moment.”

12. “I stand up and flip the light on to find she had been barfing and just kept going.”

“So it all started at my buddy’s’ New Year’s Eve party in 2009. As younger teenagers, I’m not sure what we were doing having a huge drunken New Year’s Eve party but here we were. Drinks are going and everyone is having a weird awkward teenage time when a girl I’ve talked to a few times asks if I’d come with her. We go downstairs into a dark room with a bed and she pulls my pants down and starts to give oral. In the middle of it, my best friend comes in looking for me and as he turns on the lights I realize in my drunkenness, it wasn’t the girl I thought, but a girl he was practically in love with (as much as a teenager can be). So best friends storms out but is kind enough to flip the light back off. She proceeds and I remember thinking “Jesus she is being very sloppy and gaggy” after a few minutes, and a lot more “slop” I stand up, and flip the light on to find she had been barfing and just kept going. Pulled my pants up covered in barf, walked through the middle of the entire party to the bathroom, and got in the shower fully clothed contemplated my life.”

13. “In a pitch black room someone started to give me a BJ and it was fantastic… until I realized…this dude was sucking me off.”

“I was messing around with this chick who was in the Navy (I was in the Marine Corps). Anyways, she asked if this guy could join in. 21-year-old me said sure, because we weren’t dating just randomly hooking up. Anyways, I didn’t know it at the time, but the dude was gay and wanted me to f*ck him. Everyone forgot to mention that part to me. Anyways, so me and her already started, I was lying on my back and she was riding me. He came in and she got off of me (figured she was just going to prep him to get where we were at). In a pitch black room someone started to give me a BJ and it was fantastic… until I realized she gave a BJ like she was trying to get the last bit of ketchup out of the bottle. That’s when it all hit me… this dude was sucking me off. I’m usually one to give anything a go once, but I couldn’t get it out of my head, it was a guy doing this. I went soft and went back to my room to drink until I passed out. Never saw her again.

Edit: With the rape things yea… It may have been. I was 21 yrs old (in 2008) and was in shock more than anything as mentally I wasn’t prepared. Also when I turned on the lights to get my clothes and they started arguing about the situation, and I didn’t catch much but she was supposed to let me know and didn’t. Also the dark room was due to a birth mark she had that she was self conscious about.”

giphy 3 | Stay at Home

14. “…[he] whispered in my ear: “Can you feel my thingy?”,”

“I reluctantly agreed to meet a guy from OKCupid for a coffee date and see how things went. He was a year or two younger than I was comfortable with and I wasn’t really able to engage him in actual conversation – he commented once or twice on a mutual interest and the rest was “you’re so cute” ad infinitum. I told myself I would be open minded and give him a chance. The dude had an elaborate hairstyle that had apparently been shellacked in place for several days. I could tell it was overdue for a washing. Worse, his teeth had that fuzzy look that meant they hadn’t been brushed in I don’t know how long. An unhealthy blend of optimism and low self esteem kept me from noping out at this point. We had coffee and walked around downtown for half an hour when he said he needed to go somewhere closer to home and suggested a church parking lot we could go to. To talk. Like a fool, I drove us there. He told me he had been single for over a year and was out of practice, and really, really wanted to make out with me. Trapped in my car, I felt my only option was to kiss this dumb puppy, so I did. Many thoughts passed through my head as he coated the lower half of my face with a thick layer of pungent saliva. Primarily, “I don’t have time for this”.
We stepped out of the car for some fresh air and he hugged me tight from behind, oblivious to my discomfort, and whispered in my ear: “Can you feel my thingy?”,”

15. “…[he] fingered my bellybutton.”

“He fingered my bellybutton. I can only assume he thought it was my clit, but how??

Edit: Yeah, yeah, it’s an erogenous zone for some people, but I’m pretty damn sure he thought it was my clit because when he finally touched my actual clit he was surprised. Yes, I communicated. No, he wasn’t even close to finishing me off or close enough to be able to try to.”

16. “…her boobs were on the smaller side…ended up sucking on her armpit.”

“Was with a girl that liked doing it with the lights off. The room was pitch black and I was on top of her. She said she wanted me to suck on her tits. Now to preface, her boobs were on the smaller side and her nipples where very flat. She wanted me to pin her arms to the side, so I had no way of gauging where her boobs were. I went for it and ended up sucking on her armpit.”

giphy 5 | Stay at Home

17. “Because man is born in sin and deserves to be punished”.

“Right in the middle, she gets down on all four and demands to get spanked. Dumbfounded, I ask why and she, completely serious and a bit teary, says “Because man is born in sin and deserves to be punished”.”

18. “I sneezed on her and spittle sprayed her.”

“When I get turned on, I have the tendency to sneeze. Anyway, if she wasn’t moist from the foreplay, she was after I sneezed on her and spittle sprayed her.”

19. “[I] shoot nut on my own face.”

“I was getting a bj while laying on my back. When I said I was about to cum, she let go of my dong causing me to shoot nut on my own face.”

giphy 6 | Stay at Home

20. “We break a basement window in…and my ex and I start making out. Then we hear police sirens.”

“My second blowjob ever.

I was dating this girl and I went to her house to hang out. We were in the basement watching a movie with her brother (we were on a couch behind him), and I started feeling her up. Her brother went upstairs for a few and I got my first blowjob. Sh*t was awesome. She was great at it.

Brother comes back and we start messing around some more, mostly just feeling on each other. We tell him we are gonna go walk around for a little while. We secretly go into a walk-in closet adjacent to the basement and she starts sucking my d*ck again. This one takes forever because it was uncomfortable in there and I had just came like 15-20 minutes prior to this blowjob.

Maybe 45 mins to an hour go by (god bless her, she was a real f*cking trooper) and her mom starts looking for us. She sees the light on in the closet but we quickly turn it off. Her mom knocks and asks if we are in there, and my ex’s dumbass responds “Yeah?” Keep in mind I took my pants and underwear off, and I’ve gotta get them back on quickly in the f*cking dark.

She walks out and there I am behind her, holding my pants up that were undone and ON FUCKING BACKWARDS.

Probably my best story. Dating her was pretty wild.

Edit 2: Okay, I’ll tell more.

On Halloween night, 2008 (the pants predicament happened in the August or September 2008) I went over to hang out with her. Her mom was gone, we hung out in her house, got a blowjob in her kitchen. Nice. We hung out in her back yard and one of her friends came over. Her mom came back home and we “went trick or treating”.

In reality, we walked to an empty duplex that her mom owned, and decided to use that to try to have sex. She forgot the key. So what did fully erect 15-year-old Evan and two 13-year-old girls think to do? Hey let’s break in!

We break a basement window in and her friend climbs through to unlock the door. We go in, her friend goes off around the house doing who knows what, and my ex and I start making out. Then we hear police sirens.

We decide to get the f*ck out and we run through the front door. Police run up guns drawn and stop us. We all get searched. The guy that searched me found a condom, turns me around and asks, “Is this what you were here for?” and I nod in shame, although now that I think about it now, he probably thought I was gonna bang both of them.

Our parents get called and we all sit and wait for them to come. They take our info and our parents show up.

My dad takes me home and decides not to punish me because he figured I was shaken up enough by the cops.”

21. “…tried to seductively pull down my boyfriend’s (now husband) underwear the elastic waist band slipped out of my fingers and sling shot him in the balls.”

“The first time I initiated sexy time and tried to seductively pull down my boyfriend’s (now husband) underwear, the elastic waist band slipped out of my fingers and sling shot him in the balls. Sexy time did not happen that night, which was the opposite effect I was going for.”

22. “As we’re making out, I slip my hand into his jeans but obviously, having not thought things through, my hand gets kind of stuck in the band.”

“Was messing around with a guy in college. Had never touched guy bits before and was curious. As we’re making out, I slip my hand into his jeans but obviously, having not thought things through, my hand gets kind of stuck in the band. So my hand’s already halfway in, wiggling around, I’m thinking I probably should have unbuttoned his pants first, but now it’s too late. Then he goes, “uh, what are you doing?”

I felt like such an awkward loser/borderline sexual assaulter at that point, seeing as he definitely wasn’t feeling it. So I blurt out, “oh, I was just checking if you’re circumcised…” I have NO IDEA why I said that. And he was like, “yep, I am.” And kind of laughed. I had no idea if I should try again or let it go, continue kissing, stop kissing or what.”

giphy 7 | Stay at Home

23. “When I finally felt the clit I said “that’s your clit!”… Loudly.”

“The first time I fingered a girl it was in a dark movie theater. It was of course lower than expected and I just kept reaching lower and lower. When I finally felt the clit, I said “that’s your clit!” in an excited 14-year-old voice. Loudly. During the movie. She just whispered “yep” quietly.

Edit: I woke up to my most upvoted comment! Also the girl now goes to college with me. We avoid each other.”

24. “I’m tied down with my ass in the air, back to her, and she dumps an entire molten yankee candle on my acne-scarred back.”

“My high school girlfriend was anorexic, maybe 90 pounds. She was also very enthusiastic about being into BDSM when we were both 16. I know have learned it’s not for me, but of course, I wasn’t aware of that at the time. I also wasn’t aware of the old adage of “safe, sane and consensual,” arguably only the last thing was followed.

I never really enjoyed being tied up and beaten. I usually zoned out and bode my time until we could go back to spooning or something. We also both sucked at tying knots, which was compounded by her interest in shibari, or Japanese rope tying in geometric patterns.

She also was really enthusiastic about hot wax play. Neither of us knew that hot wax was usually just “warm” wax, made from candles designed to melt at low temperatures and not to leave burns. So I come over her house one weekend, we have a nice lunch, spoon a bit, then she takes me into her parents’ bedroom (her own bed doesn’t have bedposts to tie me to) and ties me down, says she has a surprise for me. I’m tied down with my ass in the air, back to her, and she dumps an entire molten yankee candle on my acne-scarred back. I am not a strong man, but the second I had what felt like burning pitch on my back I tore through her sh*tty knots, launched her across the room into a wall where she dislocated a hip and the burning candle set her parents’ bed on fire. The burns weren’t too bad though I do have permanent scarring, I refused to go to a hospital because I was too embarrassed to tell any adults just how I got the burns on my back. I left her house and left her to explain why her parents’ bed was burned and the bedroom wrecked.

We broke up a week later.”

25. “I feel ashamed that my first intercourse was maybe 12 seconds long.”

“I’m 18, virgin, super inexperienced (late bloomer?) and this semi attractive girl from work invites me over to her apartment for a kick back she’s having with some friends. I accept, head over, slam a few sh*tty beers, and make small talk with a few of the people there. She’s smoking (I don’t smoke, and find it rather gross), but whatever.

After about an hour, the party’s starting to thin out a bit, and said female co-worker tells me to come upstairs. I’m pretty naive, but have a decent idea of where this might be headed. The second I walk in the room, she kinda grabs my face and we start making out. She’s not a great kisser, and her mouth tastes like an ashtray, but at the insanely horny age of 18 y/o virgin, I’m gonna take what I can get.

Heavy kissing becomes heavy petting becomes her taking my shirt off followed by her own, followed by my pants, and bingo-bango-jango, I’m getting my first ever BJ. Score.

She goes down on me for maybe 10-15 mins… and I’m edging on orgasm (first BJ ever, etc…). Right before I come, she stops, and whips a condom out of who knows where, and promptly informs me that were now going to f*ck. I’m on my back, and she’s very much in control of the entire situation, and given that she’s literally providing the protection, I figure f*ck it, time to lose that V card.

She manages to get the condom onto my pulsating Johnson, and hops right on top of me, like an experienced jockey on a primed racehorse. I come. Immediately. Maybe 2 thrusts in and I’m coming hard. Like first orgasm inside a woman hard. Buckets of semen hard.

I’m embarrassed, despite her surely knowing I was close, I feel ashamed that my first intercourse was maybe 12 seconds long, so I try to play off this insane orgasm like it’s not happening, and keep pumping like a champ. Big mistake.

After about a minute of awkwardly sensitive post climax pumping, I’m going limp. Nothing to do at this point but call it, so I tell the jockey it’s time to dismount, but when I pull out and look down, there’s NO CONDOM. F*CK MY LIFE, it’s gone. My minds racing… it was there when we started… right? Did she take it off? Did it fall off? Did it fall out? Where is it? Did it break? Did it dissolve? I’m petrified. I figure the only thing to do is to talk to her about it. She has no clue, figured I pulled out with it on. Now I’m even more scared, I prolly have HIV, I prolly have the clap and crabs and this chick is DEFINITELY preggers with a gallon of my seed in her. F*CK.

I go into flight or fight, I’m super scared, and I bail. Gotta get the f*ck out before I have to start paying CHILD SUPPORT FOR THIS MISTAKE. The rest is pretty boring, I calmed down later that night, called her, we agreed a baby was a terrible decision, I bought her Plan B that I gave her at work the next day, I got tested immediately, somehow came back clean, we never fooled around ever again.

One fun tidbit, about 5 days later, she said that she discovered the ghost condom, and that it had been jammed so far up her clam, and must have fallen off when I went limp, and gotten semented up there by a virgin load of an 18 y/o. It apparently eventually worked its way out (or she had to get up there and get it, idk).

So yeah, worst, scariest, cringiest sex of my life, but at least I got it over with first?”

giphy 9 | Stay at Home

Which of these sexual encounters do you think is the most awkward?

pinnable 2 | Stay at Home

About Author

Sahm Community

Stories that have been written by mums, with a raw, honest, heartfelt sometimes tearful emotions put into words. Just so that we as a community know t...Read Morehat as mums you are not alone! Read Less

Ask a Question

Close sidebar