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People Share Their Guilty Pleasure Hookup Story (20 GIFS)

Posted in NSFW 26 Sep 2023 3768

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People Share Their Guilty Pleasure Hookup Story

"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."

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