People Share Their Guilty Pleasure Hookup Story (20 GIFS)

"We met online, chatted for a couple hours, got into some sexual stuff, and then I suggested we meet at a local bar. She was around 40, and i was 25. Anyways, we had 1 drink, and she wanted to leave. Go out to my car, make out for a bit, and she says she’s gonna take off and she’ll call me later. I figured that was it and that I turned her off even though I did everything right. Get a text from her 5 minutes later with her address and telling me to come over and just let myself in.

I head over, walk in, and she was on the couch with her ass up on the air, wearing nothing but knee-high socks and a blindfold.

Earlier, when we were chatting, I told her I had a thing for knee-high socks, and she had a fantasy about getting fucked by a stranger that she was never able to do when she was married. (She had recently divorced)

We basically did every sexual thing you could do that evening. Never said a word for the next 2-3 hours."

"Kept sucking while/after he came during a bj and he lost consciousness (he woke up quickly and was fine). It happened twice and I’ve never felt more powerful in my life."

"Hooked up with a clown while she was till in her makeup and clown suit while her roommate was in her princess outfit about 3’ away watching tv."

"I, uh, I lost my virginity at a funeral. With a living person, I should clarify."

"Matched with an ex high school teacher on tinder. She said it would be too awkward to go out with me but sent me a naked pic. Jerked off to it so many times."

"I slept with my 8th grade science teacher just after I graduated HS. She had moved to my neighborhood sometime during my senior year. Every year right after school was out for the summer, we’d have a huge block party at the pool and the roads around it were shut down. (we usually had about 500-600 people each year and growing).

What started with chicken fights in the pool with her on my shoulders and going undefeated. She clung to my arm the rest of the evening (not one adult batted an eye at this) and ended back at her place. To this day I don’t know if she recalled I was her student. I am pretty certain she knew, but I wasn’t about to ruin our summer affair it by mentioning it."

"I came on a girl’s face as her mom walked in the room. It was one of those thick, holding it in for days loads as well."

"I paid for an escort at 19. Her name was Lulu Devine and she had like ridiculously large implants. We ended up going to Big Lots where I end up seeing my parents in the parking lot with her…my mom was mortified!!"

"She took off her panties, stuffed them inside herself, before slowly pulling them out and shoving them in my face and into my mouth, and held them there while she rode me into the sunset.

It’s not as wild as some, but it changed my world."

"Got my first blow job from a high school girlfriend under the blanket while her mom was working on the computer with her back to us on the other side of the room. I’ve been chasing that same mix of fear and excitement for the past twenty years."

"In a previous relationship, my ex and I would do drug fueled, amputee bdsm. He was not an amputee; He just enjoyed being tied up like he had no arms or legs.

My days are much calmer now."

"Fucking my high school bully’s big brother in her basement was a highlight. Better, she and I had the same first name so I guaranteed I had made it awkward in that house for a bit."

"Hooking up with my ex’s aunt 2 years after we broke up and I ran into her at a jack in the box. My cousin and I were just randomly looking for hangover food and just happened to decide on that jack in the box that day. I told him to head on home and I went with her to her motel. No regrets. I always thought she was sexy as hell and we never saw each other again after that."

"I was 23(m) my boss was an attractive 40f. She invited me and a few other coworkers over to watch a foot ball game. I was the last to leave, until her husband put on “pour some sugar on me” her top came off, my dick came out…we both fucked her senseless all night. We had threesomes a few times a week for months. It was amazing…I hope they are both still happy."

"Two strippers one night ripped my shirt up, wrote “slut” on my chest with lipstick, scratched me up, and one even bit me. I kind of liked it."

"Had a sixsome at a Sandals resort when we just wanted to go to the hot tub for a late night dip."

"Hiring prostitutes disguised as professional masseuse.

They offer traditional massages and also nuru sex massage. It’s a guilty pleasure of mine to get touch inappropriately and then get sex right after.

To be fair, they do a great job of actually massaging your body."

"I once made a guy orgasm just by playing with his nipples and kissing his ear. And lemme tell you, that kind of power changes a person."

"I received a handjob from a very pretty 61 year old woman, in a psych ward."

"One time in my younger years i met this girl w a filth fetish. She liked being absolutely defiled. One time we jumped into this dumpster and were really going to town when someone hit us w a bag of trash. Its not like they did it on accident either because they definitely heard us. It just got her even more excited. Homegirl was fucking nuts. It was a fun experience but it got really weird so I bounced."