Your most AWKWARD sexual experience?

Cringeworthy maybe? I dated this one guy that came in his pants when we were making out. I was sitting on his lap but it wasn’t even that steamy. He also told me to take a plan B because he thought I would get pregnant and he literally called his mom for advice. Needless to say, never talked to him again lol.
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Most Helpful Girls

  • LMFAO girl, omg! 😭😂 I’ve had SEVERAL awkward experiences. The last guy that I had sex with kept asking questions followed with “would you like that?” Like BRO SHUT UP I’m trying to focus. Another situation was when my friend of the time was shocked that I agreed to have sex when we were drunk and he was hyperventilating during the whole process of starting and then when I have him a blow job he was moaning like a girl and he sounded like those fake ghost imitations.

    • *gave him

    • Ahaha oh damn ! He was probably thinking it was a dream lmaooo

    • 😂🤣🤣💀💀💀

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  • When I was just starting to experience anal, he pulled out and I let out a little bit of poop. He laughed I cried , we cleaned up and went out for dinner and he got me to laugh.

    • Omg ! But it’s actually more common than you think I’m glad he wasn’t rude about it tho. I threw up on a guys dick once I remember i cried so hard lmao

    • Lmao.. 😁😁

    • 😂😂😂😂😂😂

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What Girls & Guys Said

10 29
  • I was 15, a virgin, making out with a guy that I severely wanted to impress. I had a crush on him for years, and it was summertime, and we were finally making out at a party. He was unzipping my jeans and his hand went down...
    But hey, I was 15 and my mom was still buying me my underwear. I happened to have on these beige, Playtex, polyester pull-ups that went up to about my waistline. I had *no clue* that these undies weren't sexy and that all the girls were wearing cute, French cut briefs or thongs.

    Suddenly he breathes in my ear: "Take your bathing suit off..."
    I was mortified. He thought the feel and look of my undies was actually a bathing suit, which I instantly identified as being way more cool than correcting him that they were my panties. So I said no, as if playfully wasn't interested in going further (even though I was), and moved his hand away - just to keep him thinking I was in a bathing suit under my clothes.

    I was so humiliated and swore I'd never get caught like that again, so I promptly told my mom I wanted all new underwear. French cuts, high-cuts, thongs, you name it -- which puzzled my mom, and actually had her perturbed over why I should suddenly go shopping to replace what I had (which I couldn't tell her about).

    Update: we never did make out again, and he never knew what my bathing suit really was.

  • My most cringe worthy was at a party drunk as hell and this guy I didn’t even know was all over me. Nobody was around he was 6’ 200lbs and in 4’9” 78lbs I was drunk and had linked and he kissing me and fingering me trying to get my pants off. I finally asked him if he was going to fucking rape me, I think that’s scared him. He got up and left it still disgusting I like had chunks still in my mouth from 🤮 I was so messed up I could remember who or what he looked exactly like.

    • nice story, tell it to readers digest

    • @Dave31989 readers digest? 🤔

    • look it up. it suits you

    • Show All
  • Never had an awkward experience... I think the sometimes deemed not acceptable experiences are what makes it all that more real! I was having an orgasm and completely relaxed and farted and he didn’t say anything during, or after... because I know he loves the fact I lost myself in the moment.
    If I fart accidentally when bending over to unload the dishwasher he does tell me I’m disgusting! Just shows that he didn’t care when it happened sexually!

    • Omg haha !

  • My boyfriend was eating me out when he suddenly tried to lift me up to reposition i guess and my neck just kinda snapped so hard we heard a sound 'tadak'. we still laugh over his overenthusiam and my sprain🤣

    • You should’ve played dead 🤡😂

    • I was in pain i thought he broke my neck lol

    • Lmao @Sheyhoney would have been hella funny if would have been the case!!

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  • When my girlfriend said to me: "Is it in yet?"
    It was...

    • Sometimes we get so wet it’s a little bit hard to feel it in there, don’t take it to heart :(((

    • Ohh, dang! Never knew that could be a thing..

  • I was trying to get over a bad breakup with my ex who had just dumped me after taking my virginity. I figured that having sex with someone else would help me move on. My best friend introduced me to his next door neighbor. They had been good friends since they were little kids. His friend was cute and so I told him I wanted to sleep with him. We met up in the woods one day to do it because we both had strict parents. At first he asked me to put the condom on him because he didn’t know how. I asked if he was a virgin, but he said no but that the girl put the condom on him when he lost virginity so he didn’t know how. I told him maybe we shouldn’t do it because I didn’t know how to put the condom on him either and I didn’t want to get pregnant. After fumbling around for a bit he got it on. I lifted my skirt and we tried to having sex by leaning on a tree, but I guess our heights weren’t compatible for having sex standing up and he couldn’t lift me up. So he decided he was going to lay down on the ground and ask me to ride him. The ground was covered in those little spiky balls that fall off the trees and so I told him I didn’t think that was a good idea. He laid down anyway, but the little spiky balls were hurting him and so he got back up. He was wearing a white shirt, and when he stood up there was a very obvious dog shit stain on the back of his shirt. One of my friends ended up calling my phone, I answered it and pretended that it was my mom and lied and said that I had to leave. He walked home shirtless.

    • Omg teenage romance 💀 lol noooo i felt the awkwardness through the screen 😂

    • As he was walking home he ran into my best friend (cause they’re neighbors). When he asked why he was shirtless and his shirt had a dog poop stain on it, he lied and said he tripped and fell into a pile of poop.

    • This sounds funny for real😂

  • Well first of all I was 17 and this dude was in his 20s. We went to have sex and he came before he even got the tip in, no foreplay no nothing so that was real awkward. After they we never talked again. I saw him a few years later at a show and it was weird as hell.

    • Quick cummers are always so awkward 😭

    • Lmao!! I don't know why I just love hate awkward moments!! The second part would have been super funny!! 😂😂🤣

  • I'd say kissing. Kissing the first time with a girl was beautifully awkward. She wanted one kiss, I was going for another, we missed the first and the second time and finally met arkwardly and made it happen 😂

  • Good for you!

  • It was literally my first time. Up until that time, our sexual relationship was mutual masturbation and the occasional non-CIM blowjob. Finally, one night I got the "green light". She was a girl who had PMS/cramps and felt it would be safe and maybe helpful, as fingering her to orgasm did.

    I was well aroused by foreplay and went to mount up as quickly as I could. So I started poking around, bouncing off her (very hairy) pubic bone. Inexperienced, I wasn't aiming low enough and kept missing. Every touch to my penis brought me closer to cumming. My final try put me into her thigh crease and I unloaded then and there.

    Not cringeworthy but disappointing and awkward for me.

  • Lmao yours is funny.

    • Lmao it makes me cringe everytime i think about it 😭

  • Well it was her birthday. So we were dressed up. She found me super hot in my style of dressing. Just as I put my arms around her, she had an orgasm! Wow I didn't know that was even possible! And we found a private space, started to make out and started kissing her in all her favourite places. She continued to have orgasms during this time as well. She kept telling me everytime I had an orgasm so I secretly kept a count of em. Just be the time I got down on her, she went on having 5..7...10... and by this time I thought she was gonna be done before we actually had done anything. And by the time I'd reached her pussy, she already had 15! But on the brighter side it was the most pussy I've ever had. It was oozing so bad, I would have never taken it out of my mouth. But she went on to 18, and I thought she was done, but turned out she wasn't. She went on..19...23...26. at this point I was begging her to stop. I was afraid if this was normal. And when she was at 27 I just had to stop all together and leave cuz I was afraid she'd have a stroke after having that many orgasms. I had to leave before I could even just have a single button unbuttoned.

    I honestly never knew a human, let alone a girl could possible do that! And I've never met another person either who could do that

  • You hit the loser trifecta on that one! Well done! lol

  • He was a virgin had to be

  • Weird to me, hell yes but in a society where some get off on fucking
    hentai cartoons. I mean, it’s still a fucking cartoon. Lmao

  • "I dated this one guy that came in his pants when we were making out. I was sitting on his lap but it wasn’t even that steamy. He also told me to take a plan B because he thought I would get pregnant and he literally called his mom for advice."

    HAHAHAHAHAHAHAHA! That is the craziest thing I ever heard! HAHAHAHAHAHA!

    • I know ! 😭

  • What a dweeb. Lol

  • My ex bruising my pee tube had to see a doctor i had it hurt for a week

    • Omg ! How did that happen? I got my throat bruised once 💀

    • She was ploping down hard when riding on top an just kept doing way to hard

    • Ouch !

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  • A boy came from Paris to my city just for me.

    He was so into me and when we were about to have sex, he got so nervous (performance anxiety) all he did was sweat and his heart started beating super fast. Long story short, he went back to Paris without fucking me, lol

    • You really had him that nervous lmaoo he probably regrets it 😂

    • Ahaha yeah, duh

  • lmfao🤣🤣🤣🤣🤣

    • My most awkward was a girl I date we was having sex she was riding me she was kinda wild and I was trying to suck her breast and we bumped heads but not in the normal way she banged her chin in the top of my head and busted her chin open

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