What’s your most shameful NSFW moment?

(Male here) Used to work in hospitality and a female colleague of mine became a ‘friends with benefits’ kind of friend. She lived literally a minutes walk from our work so we’d go back to hers all the time after shifts or during split shifts and do the deed. I was about 20 at the time and new to the whole ‘casual sex’ thing, I’d only slept with people I’d been dating. Whereas she was 27 and was wild as anything.

Anyway we’re going at it one night when she pulls out a small vibrator and suggested putting it in my ass while she was going down on me. I’m a few beers in and feeling adventurous so I thought why the hell not (bear in mind I’d never had anything put up there at this point in my life). She starts off gentle and I’m not going to lie it felt incredible so I encouraged her to put it in a bit more and be a bit more vigorous. This clearly turns her on and she’s really going for it. I’m really enjoying it until it goes just a bit too far in, makes me clench and unclench within a second of each other which in turn shoots this vibrator out of my ass long with a fairly decent sized solid piece of of shit.

In what seemed like an eternity of silence I quickly jumped up, grabbed some tissue from her bedside table, picked the shit up and ran to her bathroom to flush it down the toilet. When I got back I got dressed, looked her in the eye and said ‘I’m so sorry’ and went home (this is about 2am and we’re both working together the next day).

We never hooked up again after that and had to continue working with each other for about 3 months or so until she moved back home for another job. In fairness to her she never mentioned it and we still got on well during our shifts, but we 100% knew that whenever we spoke to each other it was always in the back of our minds.

Also reminds me of another time (same job, about a year or so after shit-gate). I went back to another colleagues place who I’d been trying for a long time to win over. Eventually got her out on a date but was nervous so was very drunk (as was she to be fair). Got back to hers and she starts getting undressed and being very suggestive….my hearts beating like crazy and I’m feeling on top of the world. She gets on her hands and knees and crawls towards the bed, I’m genuinely feeling like I’m in some sort of porn video. As she rises up and nearly begins to pull my boxers down, I turn to my left and just throw up everywhere. Her satin sheets are covered, photos of her family and friends on her wall are covered. She really was not pleased at all and unsurprisingly I was asked to leave. Again I still had to work with her for a few months after that but she wasn’t quite as understanding as the previous girl.

Turns out my bodily functions don’t like to co-operate with me when I’m drunk and horny.

/r/AskReddit Thread