"We caught up for a bit..."

"I helped my workmate get home after he got blind drunk and got into a scrap that he promptly lost. He was fine, but I'm not sure which the company didn't like more: the fact that it had happened at the Christmas party or the fact that he was under the legal drinking age.

I took him home and met his mum; I'd previously known her through her friendship with my youngest brother. I knew she dropped out of school early but didn't know why. Turns out she was pregnant quite young.

We caught up for a bit in her lounge and had enough drinks to be uncool to drive. I ended up being offered a spot in the Airbnb bungalow in the yard for the night, which I happily took her up on.

When she showed me the room, she turned to me and said "Look; I'm horny and we're both single... so what do you want to do about it?""

DreadBeardDM

Is that... is that soft jazz I hear playing in the background?

Steamy.

"It started out..."

"It started out with my buddy and myself getting drunk at a party, the night was settling down and he and I were just bs'ing before calling it a night. I jokingly told him his mom was hot and if given the chance I'd take it. Well, I guess he thought it was funny and there was no chance with his mom so he told her what I said. Fast forward a month or so we're at her house for Thanksgiving dinner. I notice she's having a lot of wine throughout the evening, after dinner she comes and sits on my lap in the living room and that's when I knew exactly how the night was gonna end. I was early 20s and she was early 40s, she taught me a few things that night. After that night I started to affectionately call my buddy son, he was pissed about it for a long time but eventually got over it."

TY4HK

You called your buddy "son"?

You brave soul.

"Back then..."

"I didn't have sex with her, but we made out and almost did it. But, we didn't.

One of my high school friends and I were in a bowling league on a team with his mom and a couple of her coworkers. On Fridays, the three of us would go bowling just for fun (league games were on Wednesdays). One Friday night, when my friend was out of town visiting his dad across the state, his mom suggested that she and I could still go. So we did. It was fun. We'd met at their house, and she drove to the alley. When we got back to her house to get my car, she invited me in. That's when the making-out started. Just out of nowhere. She started it. It was great, but we just mutually stopped suddenly. I felt guilty because, well, it was my good friend's mom. I guess she felt guilty because I was her son's good friend. She told me it just wouldn't be right. I agreed.

Anyway, I haven't seen either of them since a couple of years after high school. (Not because of that, though. We still bowled and hung out for a few more years and never spoke of it. As far as I know, he still doesn't know. Life just happens.)"

Saves_Another_Day

"It was totally random..."

"It was totally random and by surprise. I came to pick up a friend to go to a party. He had already left (this was before everyone had a cell phone). His mom had been fighting with her husband for a long time. She opened the door and let me in without saying a word, and moved out of sight fast. She was drunk. I came in, she started stripping. We never spoke about it again."

VulcanBrady

Something tells us that probably didn't do much to help with the stress or loneliness.

"I was walking to the pool..."

"Didn't have sex with her but only because I turned her down.

I was walking to the pool in my apartment complex when she yelled at me to come over and talk to her. I did and while I can't remember what she said it was more than obvious what she was wanting. What made it even weirder was I knew her because I'd fooled around with her daughter."

rhett342

Things That Are Normal Where You Live But Crazy Anywhere Else | George Takei’s Oh Myyy

"She stuck her tongue..."

"She stuck her tongue in my mouth which kind of gave the game away. We went upstairs to the bedroom and had about three hours of the best sex ever. I was 22, she was 41. Her daughter (my friend) was passed out drunk in her bedroom and slept through the whole thing."

Johnnymaddog116

Probably for the best that she didn't hear it. That would have made for a really awkward morning.

"I actually met her..."

"I actually met her during my friend/coworker's wedding at Niagara Falls. We sat near each other during the ceremony and we struck up a conversation when she offered me a fruit snack. Turns out she was divorced and lonely, so we started dating pretty soon after, which was super convenient because she was on my commute home from work. It didn't work out though because of the age difference. My friend ended up finding out and actually ended up punching me in the office parking lot."

MTGWookie

"We repeated that a few times..."

"Visited my childhood best friend after ~10 years away, I was in my early 30s. We grew up from 1st grade to graduation and then I moved away, never visited. Finally, I reconnected with my old best friend and I made plans to visit when I was near my hometown for work.

I get to his place a bit early and his mom is there babysitting his kids. We have about 30 mins to catch up, she'd known me since 1st grade and was basically a second mom to me back then. She was always a good-looking woman, but now in her late 40s maybe, early 50s, she looked amazing. Something was in the air, but I was too hesitant to call it sexual tension.

My friend gets there and we have a good catch-up and make plans for later in the week. She left about halfway through our visit and tells me to come over after but not to tell her son. I was blown away to have my suspicions confirmed. I was NOT gonna miss that chance.

I went over after and we started making out as soon as I walked in the door, the same old door I'd been walking in and out of since I was a kid. It took about 3 minutes to go from making out to sex on her couch. The couch she never let us sit on as kids, in the room with white carpet we weren't allowed to walk through. lol.

We repeated that a few times that week before I left town again. We chatted on the phone a few times and she admitted she'd wanted it for a long time. Now that it was out of her system she said we couldn't do it again. I've gotten close to my old friend since then and we've spent more time together. There's no awkwardness between her and me, if anything we're closer than ever in a real caring way. I hope he never finds out, I'd hate to hurt him that way."

bettyslow

"Ex-girlfriend's mom. Had dinner at her house every Sunday while dating the daughter. Six months after the breakup I see the mom at the store, we catch up. mom invites me to dinner since the ex never goes anymore. First dinner was normal, second involved too much wine and a long, deep kiss goodnight. Third week we didn't even bother with dinner, just straight to bed."

smackmewithapickle

"I went to a few barbecues..."

"My friend's mother-in-law, if that counts, I went to a few barbecues at her house one summer and she caught me admiring her legs, challenged me cheekily and we ended up spending a few fun evenings together, fun times."

Old1Kenobi

There is so much material here that would fit right in a goofy sex comedy... but take note that relationships like these can get messy (especially if you're still in contact with your friends).

Have some stories of your own? Feel free to tell us about them in the comments below!