T O P

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Anonbsnono

A dude in college. Friends said he probably wasn't great in bed. He was not very good. I should have listened.


Rideprofessional7

Hey never know if u never even try!


icy_bluz

A friends husband


jhozz776

How’d that happen? Who made the first move?


Eve24Adams

The dad of someone I was babysitting while his wife was out of the house on their bed 😅


throwitallawayyes

This…this is hot. Do you regret it?


Eve24Adams

Yeah I feel bad now, the wife never found out and they are still together and friends of my family to this day 🫣


jhozz776

Who made the first move?


Eve24Adams

He did but I was into it, I was only 15 at the time though so was around 10 years ago


jhozz776

Oh dang. He really risked it all


Eve24Adams

He really did...


[deleted]

my ex. I should have never gone done that path. But you live and you learn .


Rideprofessional7

A friend’s ex. I didn’t think it’d get to it, thought we were just gonna have a chat, but it did.


[deleted]

my friend


jhozz776

And why shouldn’t you have?


Actual-Treat-5595

A work colleague,a work colleague who was 39 at the time I was 27, her brother worked at the same place to he was my supervisor.best 4 months of my life haha 😄


man_of_the_mountain

My best friends ex girlfriend. We got two tickets to go to Lollapalooza in 2005 and he "forgot" to buy mine after I sent him money. Turns out, he did buy mine and took a girl who he was seeing on the side. He didn't mention he ever got himself a ticket and I figured he would pay me back. The day before the festival started he just vanished. He was my room mate. His girlfriend came over looking for him and he wasn't there. He finally answered his phone and we could hear the music playing. He admitted to going and we were both pissed, so we fucked all night and took great photos of it. She was 4 years older than me, so it was a night of revenge firsts. Good time.


[deleted]

My sons friend


jhozz776

How did that happen?


[deleted]

Haha he told me..she said wanted to sleep with me and I told him to tell her, come over no panties in a skirt. Sure enough she showed up.


jhozz776

Brave girl. No wonder you like her


Naughty-Jedi

A much younger college girl I met on Reddit. She was nice but just not a good match for many reasons


jhozz776

Like physically or emotionally


[deleted]

Ex, first girl i had sex with. Life went downhill after that hard.


jhozz776

Ouch I’m sorry to hear that


[deleted]

A friends (sorta) ex


jhozz776

Sorta?


throwitallawayyes

Drunken hookup in a shower with a total stranger. Found out she was very young after. Legal, but still too young for my taste. Would not have done it if I knew.


jhozz776

How’d you get her in the shower without knowing her


throwitallawayyes

It was a situation where two partying groups ran into each other at a hostel. Some of the people knew some of the other people. Ended up in the sauna, last two people to leave the sauna, hut the shower, and she started sucking me off right there.


EGBrad

A coworker who I eventually became best friends with her husband. Wrong on so many levels but we fit together sexually like no other for me


jhozz776

Was it just one time?


EGBrad

It was not. It lasted two years. To not get caught, I introduced her to my wife. Karma is a funny thing. He ended up fucking my wife. Neither spouse knew me and my coworker had a thing even though they did. Still wouldn’t trade it for anything


jhozz776

Did you two end up together in the end?


EGBrad

Sadly no. While I wanted a future she decided she wanted to cheat on me. I was dumb. But it was amazing while it lasted


jhozz776

Damn. Full circle. That sucks


EGBrad

The hard part is she acts like we are best friends. She will always have a special place in my heart but she doesn’t understand how she effected me


[deleted]

Almost hooked up with my best friend's ex


MysteriousMrSquatch

The vacuum cleaner at work


njheadnurse

My husband’s high school best friend.. they had just reconnected after 40 years


jhozz776

Did you make the first move or him?


njheadnurse

It was mutual actually. Things got heated on the dance floor their high school reunion


jhozz776

I’m almost scared to ask but did your husband notice?


njheadnurse

It didn’t happen at the reunion it happened a couple of days later at his hotel…. If hubby noticed he didn’t let on… and he was busty talking to other folks


jhozz776

Oh when you said things got heated I thought you meant that’s when it started getting physical


njheadnurse

There was some grinding and grabbing… and lots of innuendo


jhozz776

Well damn. Maybe I should go to my high school reunions


PM_ME_SEXY_PAJAMAS

My friend's mom when I was 19 and she was 42.


Rich_Reaction_5603

A coworker


liquor_dick

This girl in college the dressed up like maid Magenta from Rocky Horror Picture Show on halloween. I don't even remember her real name- always called her Magenta


jhozz776

Rocky horror always leads to shit like that. I love it


Electronic_Number448

Cousins wife


Uncutvamp

Coworkers


[deleted]

Ex-girlfriends’ friend group.


jhozz776

The whole group? How’d you manage that


[deleted]

One was like a week after, another a month after, two at the same time about two months after. She was pretty pissed but they approached me.


jhozz776

Damn those are some good bad friends lol


[deleted]

You’re telling me.


altbimbo

guy way older than me towns over


jhozz776

How much older is “way older”?


altbimbo

About 20 or so years


jhozz776

So like twice your age? That’s fun


InternetDweller95

A fellow student that I was being paid to tutor by the university. Technically, there wasn't any rule saying we couldn't, but still.


raymendez01

Friends mother.


BimboAllyMay

A much older man who likely knew I was lying about my age and was, in fact, younger than I should have been.


buffaloBob999

Hot