One time while hooking up with a college partner, I figured I’d be real slick and try to pick her up for a standing 69. Dropped her right on her head and sprained her neck. I had never been so mortified before or since.
-Unknown
2
I was 17 and taking community college courses. In my improv acting class, we had a group ice breaker activity where we had to guess what kind of person other people in the small group would like to date.
In retrospect, my nerd ass whiffed entirely when the girl with black lipstick, dark eyeshadow, and piercings suggested I would probably date a submissive goth girl. Me to past me: SHE WAS FLIRTING WITH YOU, DOLT.
-IkomaTanomori
3
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Mine was when I was a freshman in college. I was pet sitting for one of my parents’ neighbors. I thought he was into me, so I tried the “naked woman” when he returned from his trip, laying in his bed waiting for him.
He…was NOT into me. He freaked out when he saw me and basically just yelled at me. I felt so stupid.
-lphamconfession
4
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I had a date one night and after about a 3-hour make-out and oral session, she wanted to have sex. She grabbed a condom I brought and proceeded to put it on me.
First, she says she had gotten used to putting condoms on guys with her mouth, and that way they didn’t complain. Granted, I wasn’t going to but I didn’t know this was what she was doing. If I had, I would have warned her ‘hey, that one has spermicide’. She found out. I never had seen a lady spit and gag like that before.
-cthulutx
5
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Me and a girl were vibing waiting in line for a movie. We end up sitting together. I ask her if she wants to make out. “I have a boyfriend.” Longest 90 minutes of my life.
-ElboMan
7
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At the start of our relationship, my now wife and I crashed at another couple’s house on a Sunday after work, have a few drinks, etc. One week, the female of the other couple suggested we ‘share a bed, you know, see what happens?’ We knew they’d swung before, and it seemed like a fun idea…At the time.
We were getting into it, I was with my girl, they were together. She reached over to start touching my girl up, bit of kissing, feeling her tits up, light nipple sucking, then she reached down to my girls vagina, literally the tip of her finger touched my dick…and she lost her shit.
[Cont…]
8
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Not in the good way. She went batshit crazy. Her bloke was confused as hell. We were confused as hell. She just sat in the bed shrieking. So we got the hell out and went downstairs. Turns out that she didn’t want me, or her guy there at all. She just wanted a turn on my girl.
-kieronj6241
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I’d had a threesome with my “at the time” partner & our mutual friend, they’d continued to fuck each other behind my back before I was dumped & our friend became my ex’s new girlfriend, I was depressed & in my lonely desperation I tried my best to get another threesome with them.
I was turned down which had to be my most humiliating sexual mistake, certainly made things even more awkward than they already were, the friend said she’d “respected me too much” to do it again.
-PrincessxXxDarkstarr
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The wife likes the occasional spanking/paddling session, but as a person with a disability that can affect my balance and coordination, sometimes I will make minimal contact or not connect at all.
…thus, my “swing and miss” is a literal swing and miss.
-scarred2112
11
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Was dancing with this girl at a club and things were going well, I told her that I wanted to kiss her and went in for the move. She stopped and told me that she was a lesbian and was just dancing for fun. Whoops.
-ENDofZERO
12
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At my sister’s baby shower I ran into my ex from high school. We were flirty the entire time and she asks me if I wanted to go for a drive with her. We left and after a few minutes of driving she pulls into an empty parking lot and we start making out and heavy petting. I reclined my seat and she starts sucking me off and I’m playing with her. All is going well and I’m thinking I’m finally gonna hit it.
Suddenly she flips over on top of me and thrusts her vag in my mouth while still sucking me off. I was not ready for that AT ALL and apparently, I was not into it because my guy went limp, like an old man who’s been unable to get it up for years limp. Bless her heart…She kept sucking on it while it was flopping around like a cooked hot dog. The next 30 minutes were the most awkward of my entire life. I guess it was a swing and a miss for both of us.
-flakof22b
13
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Tinder date with this girl, Fours hours of foreplay and cuddling, couldn’t get hard because of the liquor. Sex wasn’t had.
-Skeptical_dude12
14
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Not my “swing and miss” but theirs. I got invited to watch a football game at my neighbor’s house (two females). They invited me in, gave me drinks, and asked me to work on their computer in their room. We sat there and I fixed an update on their laptop and left. They later told our mutual friend that I couldn’t pick up what they were laying down. 10 years later, and I still regret being stupid.
-eat861019
15
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I met a girl on Tinder a couple of years ago. We chatted on the app, were into each other, and wanted to meet up for a drink. There was immediate chemistry. We were very much into each other. Lots of touching and flirting. At one point, we were facing each other, holding hands, and she asked me about some of the crazy/kinky stuff I’d done before.
I did some very quick, whiskey-fueled mental math about not wanting to seem like a truly perverted deviant, but also wanting to express my sexuality. And I came to the conclusion that I’d mention group sex and that I enjoy having fun with guys in that context.
[Cont…]
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As soon as the words came out of my mouth, she completely withdrew. Stiffened up, and was completely uninterested. She paid for her drink, wished me the best, and left. Clearly, this relationship was not meant to be long-term, but I still wonder if I’d have picked a different kink, would we have had an amazing evening together?
-jakebrooklyn
17
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So it started on the last day of my senior year of high school when my neighbor’s house burnt down. They lived with us (we were very close) for about 5 months while their house was being rebuilt. Their daughter (my age) was sharing a room with my sister, the parents took my room, I slept on the couch.
The daughter was being really nice and touchy-feely with me for the first few weeks and I thought she was hitting on me. One day while we were chilling by the pool, I tried to kiss her. She looks me in the eyes horrified and says “I’m dating your sister!” Turns out she and my sister had been sleeping together the whole time and she was just feeling bad for me because I had to sleep on the couch.
-dagonz7
18
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At one point in my life, I had two ‘Friends With Benefits’ relationships going. They both seemed open to having a threesome, so I arranged for us to have dinner so they could meet and we could discuss the rules and such.
They did NOT like each other. Soon as they were in the same room, there was negative tension. We got through dinner and we all went back to our separate homes never to speak of this again.
-Obvious_Alt_251
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