Tales of Threesomes Gone Wrong

For many, the idea of a threesome is the ultimate fantasy. Pleasing or getting pleased by two people at the same time? Sign. Us. Up. We’ve all seen porn, so we know that threesomes can be all-out pleasure fests. But, as with most things in porn, the fantasy doesn’t always translate in reality. At least was the case for these poor folks. Here are a few real-life tales of threesomes gone wrong.

A Respectful Twosome

“I was dating two waitresses simultaneously, both of whom were in other relationships. One night we all ended up in the same bed. One of them was an animal, and the other one was a bit more shy. So confronted with the situation, the shy one wasn’t keen on the threesome. So instead of being an asshole I very respectfully shagged the other one while the shy one went to sleep.” — Dane, 35

Failure to Report for Duty

“Two of my women friends got horny enough to suggest we all have a threesome. This was going to be my first one, so I basically geared up for the greatest night of my life. When I got to the apartment, everything was working just as it was supposed to until my soldier decided to not show up for duty, if you know what I mean. I think I got stage fright. Cut to me in the bathroom yelling at my dick to stand up, saying ‘This is our moment, buddy!’ When I came out of the bathroom the two of them had already started with each other and I still wasn’t responding so I just went home. I was depressed for two days.” — David, 34

‘Hooker’ is Not a Compliment

“My partner and I brought another guy back to our place for a fun night of play. When I was giving him a blowjob, he started saying, in broken English, ‘you blow like a hooker.’ My partner couldn’t stop laughing and eventually we had to ask our new friend to go home.” — George, 39

Freudian ‘Slip’

“My husband really wanted a threesome, so I decided before we got married I’d make it happen for him. We had one rule: he didn’t put it in her. Everything was going fine, we were all in heap with flailing limbs and people kissing parts and I was insanely turned on. I mouthed to him, ‘finger her.’ I guess in his euphoria he interpreted it as, ‘fuck her.’ He started to put his penis in her, so I freaked out and ran out of the room crying. That was the last we ever dabbled in threesomes.” — Lauren, 33

Master of None

“I’m not a newbie to threesomes. I’ve actually had quite a few in my day. I love them, but only when I’m the guest star. I couldn’t deal with the emotional fallout after a threesome if I was in a couple. Especially when the man in the relationship yells out the name of a woman who wasn’t even part of that particular threesome. Oh yeah, that happened. And his wife was not okay with it.” — Becky, 42

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Tales of Threesomes Gone Wrong
Tales of Threesomes Gone Wrong
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Meagan Drillinger

Meagan Drillinger

Meagan Drillinger is a contributing Editor for the Tickle Kitty Blog. She's also a freelance writer based in New York City, but you can usually find her buying plane tickets to literally everywhere else. Her writing has appeared in Travel + Leisure, Men's Health, Thrillist, and many others. You can follow her adventures on her blog or via her Instagram. She is also the founder of Vaera Journeys, a travel retreat company for entrepreneurial women.

One thought on “Tales of Threesomes Gone Wrong

  • Avatar
    February 25, 2019 at 5:37 pm
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    I’ve had many great threesomes but in the beginning i learnt very quickly. Never give the 3rd person more attention than yr partner. I also came when i shouldn’t have. The other girl wad so hot i just lost my load inside her, my partner wanted to go down on her but was met with dribbling leaking cum and it spoilt ir for her. So guys hold off and never get off before all present have had theirs.

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