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The contents of this article are adult in nature. Reader discretion is advised.
Disclaimer: Some names have been changed for privacy purposes.
“He was done in two minutes and asked if I came”
“I once had sex with a dude on the floor of a public toilet (it was really clean but still). And he was done in two minutes. Then he was like ‘Did you cum?’
“I don’t know if that is awkward, crazy, or just sad. hahaha.” — Fatin
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“She cracked a big fart and it was a stinky one”
“I met this girl on a dating app and it was two months before we made it to the bed. The position I love most is Doggy Style but it led to the most awkward sex with her. As [we were getting it on hard], she cracked a big fart and it was a stinky one. Luckily, no shit came out. That was the last time we met.” — Brandon
“I try not to kink-shame, but this was by FAR the most awkward hook up of my life”
“I once met this guy in Pre-U that I knew always had a thing for me. My rule was no hooking up with someone in school because it would be awkward moving forward. But Pre-U was ending and I thought why not lol. So one day we went back to his place (he lived on campus) and we made out for awhile. He asked if I wanted to have sex, to which I said yes too (obviously). He then told me that he only had sex with guys if they’re tied up. Naturally, I was alarmed, but he reassured me that it wasn’t going to be against my will and I could stop any time. I knew him well enough to know he was telling the truth, so I went along with it: I got naked, he tied me to the bed (hands and legs), and we began.
“The foreplay was nothing out of the ordinary, but then we started having sex. I was the top, so he started to ride me in a cowboy position. It was fine until he started dirty talking and said things like, ‘Yeah do you like that, slave?’, ‘Tie you up and keep you here to use when I please’, and ‘I own you bitch’.
“He slapped me a couple of times too but I didn’t think much of it ’cause it wasn’t rough nor did it hurt. But he seemed to get a kick out of demeaning me during sex LOL. I’ve seen ’12 Years a Slave’ too many times to be calm, so I quickly made him cum and got out of there as fast as I could. He tried to meet up again after that, but I said I was perpetually busy so it ended there. Luckily, it was towards the end of Pre-U life, so it wasn’t hard to avoid him. I try not to kink-shame, but this was by FAR the most awkward hook up of my life.” — Sandeep
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“He started moaning like a little girl”
“This random guy started moaning like a little girl during foreplay. Halfway through, I got so turned off, I told him I had to go and just ran out saying ‘Sorry it’s not you, it’s me’. Safe to say, we never talked since then. I got into the car and immediately drove off to the next guy and had one of the best sex.” — Elisa
“They were in-sync in a lot of ways, and it was hot how they’d rotate between giving me foreplay and having sex simultaneously”
“My former girlfriend was a twin, and we had a pretty stable relationship and sex life. Nothing particularly out of the ordinary but the sex was good. I always got a pretty weird vibe with her sister because I felt like she was flirting with me once in awhile. She even sat on my lap one time in front of my girlfriend, and that took me by surprise.
“Eventually, I told my girlfriend what my concern was and she confessed that her sister low-key had a thing for me, because my girlfriend would tell her about our ‘sex-capades’. About a week later when my girlfriend told her sister about our conversation, she asked if I would be open to a ONE TIME threesome with both of them. I wasn’t completely turned off by the idea, but after a bit of convincing, I warmed up to the idea and we had a threesome.
“It wasn’t my first time having sex with multiple partners at one go but it was definitely crazy. They were in-sync in a lot of ways, and it was hot how they’d rotate between giving me foreplay and having sex simultaneously. There’s something about having sex with a pair of twins that kind of changed the way I view my sex life currently, and let’s just say that not everything about these girls were identical LOL.” — Kieran
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“I was jiggling everywhere, it was super unsexy to me”
“I had changing room sex once. It was really awkward. There were just too many mirrors. Probably nice for the guy but I just kept laughing ’cause I was jiggling everywhere and it was super unsexy to me. hahaha. Plus, the mirror did that effect where you saw lots and lots of yourself in that infinite reflection. I found that extra funny.” — Emily
“He kept calling me ‘baby’ and I just wanted it to stop”
“I hooked up with this guy who left the ‘price’ of our dinner on his computer, complete with my name too. I felt like a statistic but I gave him the benefit of the doubt and thought, ‘Okay, he’s just someone who tracks his finances’. But as the night progressed, it just kept getting more awkward.
“He kept calling me ‘baby’ in bed, despite me telling him that it was a total turn off. He also opened at least 10 to 12 condoms throughout that night. I understand some people like a guy who can go several rounds non-stop. But honestly, I was just so out of it and exhausted. By morning, I was SO ready to leave.” — Tricia
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“We did it on his youngest brother’s bed”
“I broke up with a guy but we remained close upon agreement of being purely friends with benefits. One night I drove to his place horny, and we ended up doing it on his youngest brother’s bed. I feel horrible about it to this day, though it was one of the best sex I’ve ever had.” — Lim
“They just watched everything… They rated the live sex show 8/10.”
“I was in a friend’s room with my then ex-boyfriend and two other friends. My boyfriend got frisky and started touching me and I too wanted to get it on. One thing led to another and next thing you know, we both started having sex in front of our two friends.
“They just watched everything. Halfway through, we wanted the bed so we just jumped on it and they quickly jumped off. Proceeded to the shower and they just followed. They rated the live sex show 8/10.” — Marianne
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“When he put it in, I couldn’t feel anything. Not a single thing.”
“I never really understood why people would comment on sizes… until this one guy I met. Things got heated and we moved to his bedroom. But when he put it in, I couldn’t feel anything. Not a single thing. D: Now, I’m not someone to diss sizes, but if you know you have a small ‘ahem’ then I would expect you to pay extra attention to your skills/foreplay, right?
“Even when he said he was about to cum, I felt nothing. It was dark so I never really saw his actual size in the end. But, damn… guys, please pay attention to your partner to see if they are enjoying themselves too ’cause my deadpan expression should have been a giveaway.” — Amelia
“It was so horrible and painful, I pushed/punched his head”
“I grew pretty close with one of my housemates and one night, we ended up sitting on his bed then started making out. After some time, he wanted to give me head, so I decided to let him try. But it was so horrible and painful, I pushed/punched his head, snapped my thong back in place, grabbed my shorts and ran out… into another (male) housemate’s room to bitch about how horrible it was. Barely spoke to the culprit ever since.” — Mel
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“We were both butt naked, having super passionate sex on a balcony with transparent glass barriers”
“It had been quite a while since I last had sex (about three weeks) with the woman I was dating, since we were both super busy with our own schedules and other important commitments. We decided to set a specific date for that awesome sexy time because at least it would give the both of us something to look forward to, kinda like a vacation.
“We met at her place, had dinner, watched a movie, and then of course, we started ‘cuddling’ and getting really handsy. It felt so good – like, FINALLY – you know?
“Obviously, we were both incredibly horny at the time ’cause three weeks is definitely a long time to go without any sex. But as a dude who didn’t have sex for that long, you can probably guess where this story goes.
“As I went down on her (because ladies always cum first), her intense bodily vibrations, her heavy breathing, and her thighs tensing up just got me so horny to the point that I didn’t even need to worry about keeping my ‘friend’ up.
“‘Great,’ I thought to myself. Little did I know that I would actually cum as soon as she put my penis in her mouth. At first, I was incredibly embarrassed. But she kept on going?? And for the first time in my life, I realised I could keep on going as well.
“Perhaps it was because I had never been that horny in my life up until then. We then proceeded to have sex on her balcony (it’s a really high floor, low risk) because the bed was apparently too far away? And for some reason on that night, the sky was completely clear. No clouds, just a few stars (or probably airplanes hahaha) twinkling. She was on top, and my view was unbelievably magical.
“It looked and felt as if I was in some vivid sexual fantasy, with her hair slowly flowing with the light breeze, and the sound of nothingness. It was a public holiday. The thrill of possibly being caught just made me even more horny, if that makes any sense. After all, we were both butt naked, having super passionate sex on a balcony with transparent glass barriers.
“At one point, someone definitely saw us smashing. At least, that’s what we suspect. After some intense missionary (yes, missionary can be super fun), I finally came a second time.
“I thought it would be over by then. But she wanted to go again, and I thought to myself, ‘Am I actually capable?? Has the tank already drained itself??’ Surprisingly, it didn’t take long for me to cum a third time. She did most of the work, I guess she missed it that much? Mainly with her on top, and not being gentle at all hahahah. She made me finish in her mouth. It was amazing. It made me realise I was actually capable of coming this many times in one go.
“Since then, two rounds is (almost) always a minimum, depending on the situation. That one night kinda unlocked this ‘ability’ so to speak. Might not be crazy to some people, but it sure is to me.” — Amir
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