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What was your most awkward sexual encounter? 

Precious moments from the anonymous folks who filled out our Sex+Dating survey

click to enlarge Click here for all of our Sex + Dating coverage
  • Click here for all of our Sex + Dating coverage

Strange things can happen when you take your clothes off with another person, that's what we've learned from a) life and b) this year's Sex & Dating survey. This year we asked our readers to share their most awkward sexual encounter to date—and they didn't disappoint. Dicks of all shapes and sizes, surprise periods, hilarious interruptions, sweat, piss and animal voyeurs are among the best answers, but here's a round-up of the comedy gold, straight from the bedrooms and backseats of Halifax.


“I went home with someone eight years my senior who'd previously expressed his infatuation for my friend. Like many of my early sexual encounters, I was much too drunk to be engaging in any sexual activities at all, but still I rise. When we got to his house I fell backwards, naked off the back of his very high bed. I managed to put a hole in his wall and break his weight bench. I don't remember what happened after that but I woke up the next day alone in his bed in a pile of my own spaghetti barf. He still drove me home though!”


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“When I was 19 I was giving a guy head in the elevator of my building (at about 5am, after partying all night), suddenly the elevator started going up. We made ourselves decent right before someone else got on the elevator, and then had a very awkward elevator ride back down to the ground level where the person departed.”

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“My first one night stand I ever had we just went down on each other. When they came in my mouth some went up my nose but not really out. I was too nervous to ask for kleenex for some reason... I waited until I used the bathroom in the morning to dislodge it. Never been more uncomfortable or felt more ridiculous! Glad I'm not that shy anymore.”

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“One time in high school, I went out to meet this guy around midnight and we were driving around and decided to park outside of a provincial park. We started banging in the backseat, and next thing you know, a car pulls up and it’s the police! So the officer comes up and knocks on our window, which is very steamy, while were scrambling to get dressed and when we finally get the window down and asks us if everything is OK. To which we embarrassingly say yes. And he just says, 'Carry on!' It was the worst.”

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“Tinder date took me to her place, she had like five cats (red flags!). Decided to Netflix and chill. Didn't think anything was going to happen since it was a first date. Next thing I knew she slid her hand down my pants and next thing I know I've nutted all over my chest under my shirt. I get up and I'm already covered in cat hair from head to toe, and now jizz too.”

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“The town I grew up in had horrible sex education on how women react to pleasure and stimulation. We learned about male ejaculation because that's how you get pregnant. The first boyfriend I fooled around with I had no idea what was happening to me. I didn't know that my wetness was a thing that was supposed to happen so I kept excusing myself to go to the bathroom to 'clean myself up.' I think this story is more sad than anything else. Fuck the patriarchy.”

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“A guy who everyone said was the hottest guy ever, had mutual friends with me. We all went out drinking and afterwards we started hooking up. He started to go down on me but skipped right over the 'front door' and went to the 'back door.' He stayed there and never even paid attention to the rest. It went on so long I even tried to gently push him in the right direction. We had mediocre sex after and I still laugh about it.”

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“It was the first time I had hung out with this guy, one-on-one. He had just pulled a week of graveyard and had been incredibly tired, but there had been a ridiculous amount of sexual tension between us for quite a while. As it turns out, he finds blowjobs incredibly relaxing and ended up falling asleep while his cock was down my esophagus.”

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“I was passed out after puking at a party at my new GF's (ex now) house. She brings a girl and a guy into the room, wakes me up, then proceeds to try and have a foursome. My dick was too drunk unfortunately and I probably tasted like puke so it never went past kissing and touching.”

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æMy boyfriend and I were at his parents' house having sex in the shower. My house has always had glass sliding doors instead of a curtain so during shower sex, I always used them to help sturdy myself. His parents' house, on the other hand, had a shower curtain. We were in the middle of having stand up doggy-style sex when in the moment I instinctively moved my hand to the right to hold myself up, forgetting that there was no glass door there. Next thing we know, I'm falling. I wrap my hand around the curtain to try to stop myself but the force of my body falling ripped the curtain rod out of the side of the shower and it came swinging down, hitting me dead centre between my eyes. Had a nice, half-circle bruise and goose egg there for a few days.”

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“The first time I hooked up with a stranger, he decided anal was going to happen without prepping me first, which didn't work, and I was too nervous to get it up, so that didn’t work, so we made out and he kept telling me he loved me because he was high as fuck. The only thing I got from that night was herpes.”

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“Sad handjobs in a guy's basement apartment that smelled like feet and desperation. I came over to watch porn and he greeted me in bare feet and a stained shirt. The porn was people camming and the handjobs were belaboured and dry. Ugh.”

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“Guy only wanted to suck his nipples which were about the same size as his penis. This would not have been a problem if he didn't lie about having a huge penis.”

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In Print This Week

Vol 28, No 3
November 12, 2020

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