Hook-Up Horrors: When Plans Go Awry (19 GIFS)
3 Oct 2023
"Using Icy/Hot to masturbate when I was 12. Thank god I was home alone because that shit hurt lol. Told that story to a coworker once and he started calling me Icy-Cock."
"When I was younger I tried a position I’d seen in a porno, basically putting her legs over my shoulders and lifting myself up into a squat, so only her shoulders were on the bed. I proceeded to try my absolute best to go as hard as possible.
It didn’t end well for either of us as I shat on her bed."
"We were fucking like rabbits, she tried to switch positions, and instead popped my hip out of socket. It was a painful climax. After that we decided to stay in one position."
"I was eating a girl’s ass when she farted right in my mouth. My hair blew back and everything. My husband and I were in shock so we didn’t know what to say. She was extremely embarrassed so the threesome ended really fast after that.
We told her it was ok and shit happens but she was too embarrassed to have another threesome with us again."
"Bought some lube off amazon used it and it gave my dick a rash."
"I tried pegging with my ex (It was his idea, he had the gear before we met).
It was gross and smelled like poop the whole time (I’ve had anal plenty of times and never pooped on anyone or made the whole room stink so this was a him issue)."
"Using Vaporub to lubricate."
"Keeping my eyes open as he finished on my face. The pain in my right eye lasted for 3 hours. Cum stings like a bitch, never again."
"Was taking my lady from behind pretty aggressively and my balls were hitting her ass harder than I realized in pre-orgasm ignorance.
Shortly after I shot my load my balls started explaining that they hadn’t liked it and for around the next 72 hours it felt like I’d taken a huge kick to the balls."
"Sleeping with my roommate’s ex. In my defense though, I didn’t know it was my roommate’s ex until after the fact. He dated her like a year prior to that and never brought her around or anything so I had no clue.
That ex definitely knew that we were roommates though. Clever girl.
Yeah as you can imagine, it was hard staying friends after that."
"Girlfriend heard that a listerine strip made a blowjob better. I ended up with a piece of lava stuck on my dick and her laughing so much she kept clamping down and I couldn’t get my dick out safely.
*pro tip 20 years later: enthusiasm is all a blowjob needs."
"I fucked a pineapple. Not my proudest moment."
"I regret doing anal after we went for a curry."
"Met a girl in a club on Long Island, making out on the dance floor, she grabs my hand we go outside, I did not have a car, thought she did, She takes me behind a dumpster. I was like what the fuck is this, we go at it, we are finished.
She smiles and said, I love fooling around out here. OMG I felt like I needed a shower. Went to a different BAR,, lol she just went back inside…. cannot make this stuff up…"
"Gf came home drunk after a party and gave me a BJ. Afterwards she told me she sucked another guy’s dick at the party “but just for a second, I regretted it almost instantly”. The other guy was a buddy of mine, who knew it was my gf…"
"My first time having sex the condom broke and I was in fear of having a baby with a really nice but weird girl. All of a sudden it felt too damn good and I couldn’t stop!"
"Receiving a blow job in high school science class, I thought she was being playful and teasing me saying she’d like to do it. I wasn’t paying much attention and she was under the lab bench with my shorts down before I could say anything . We weren’t dating or shared any romantic exchanges not even flirting before this.
To be fair I wasn’t very good at noticing flirting so maybe this was her way of saying I like you. I had a full blown panic attack, froze and just stared bug eyed at the white board . If something like that happened now, I’d be all for it, back then it was terrifying."
"I did not washing my hands thoroughly after cutting jalapeños."
"GF and I aren’t exactly spring chickens – we ended our day by rubbing each other down with some IcyHot – then in the process of coating every nook & cranny got out selves rather horny – IcyHot soaking into the thin skin of a guys dick, and IN a womans vag – is quite painful – and if you can maintain an erection throughout (Godbless cialis) can lead to some awesome angry spiteful sex.
But I wouldn’t do it again."
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