Quick Editor’s Note: Some of the below responses required quite a bit of text, so I kept the more long-winded answers towards the bottom. Now get to readin’!
2
“My brother’s best friend from high school dated my Mom in his 30’s. She had my brother really young, when she was barely 15, so when his friend was in his 30’s, she wasn’t yet 50. I will always remember the night he found out. They fought, and my brother’s friend left the house and got into his car. My brother followed him out and punched him in the head through the driver’s side window. He managed to go through the window and still connect with enough force to knock him out cold.”
-Knytemare44
3
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“In my late 20s, I had a friend in a small mountain town in the Western US. His Mom gets separated, moves in with him. She’s mildly flirtatious with me, no big deal. Not enough to raise any red flags. Job changes and I move to the city, 90 miles south.
He comes on weekends to party a few times, normal stuff. Then he comes to party and brings her. At her request, we have a late-night fuckfest while he’s passed out in the next room. Major violation of bro code by me, but she asked nicely. No surprise we weren’t friends after that.”
-mytmatt2112
4
“I got super fucking drunk at the friend’s mother’s house, we all did really, but mainly me and the mum…But I’d come as my friend was going through a bit of a tough time and it was supposed to be a nice surprise, my friend was going to her mum’s for a nice night of merriment and the mum told me I should come to cheer her up, which I agreed was a good idea… Everything started out fine, but as she and I got more drunk, we started kinda flirting (something that had actually happened before when we were both drunk).”
“Then when it was time for everyone to go to bed, I “snuck” into her mum’s room. My friend totally knew, a fact I wasn’t aware of until a little while after, but her mum then had to drive me to the train station to go home the next day. What happened after is I, like a complete coward, never apologised, even after I found out my friend knew, and I lost that friend. They deleted me from social media and didn’t speak to me for almost 2 years.”
-Sharkary
5
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6
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“I have slept with two of my Mom’s friends. The first one she just asked if I wanted it and it happened. The second one, I went to her house which was a couple of hours away to do some handy work. The next thing I know we’re drinking and we ended up having sex. It went on for about six months after that. I’m not allowed to meet her friends anymore, which is okay because I’m happily married now.”
-Slow-Shoe-5400
7
“I used to babysit a lot for my ex-boyfriend’s family. It’s how I met him. He had a toddler sister when we were dating. Parents were split and I used to babysit for his dad when he had custody. I would watch his Dad come back from dates totally rejected and broken. I felt horrible. He was a genuinely nice guy. Attractive. A little older but I have a thing for older men.
When night he got a little flirty with me and I got a little flirty back. I spent the night. It became a big issue the very next time I babysat. His Dad expected sex now. His Dad also started to get really touchy all the time. Like I was feeding his daughter in her high chair and he started groping me. Or I was changing a diaper and he had his hand up my skirt. I had to stop after he threatened to withhold my payment if I didn’t blow him. That’s how I fucked my ex-boyfriend’s Dad.”
-cuckedprincess
8
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“A friend of mine’s mom basically hit on a number of us in the group and, sadly, it just became kind of a matter of time before one of us caved and it eventually happened. He saw it coming I feel bad for him. Recently divorced mid 30s hot mom and a group of 18 yr olds. It wasn’t me who did it.”
-burnerforsurevato
9
“One of my first girlfriends in high school. Her mom used to seriously tell her that she should give me her virginity. Often. Then mom started flirting with me. One day while at their house mom grabbed me in the hallway and kissed me. After we split up mom used to still call me every now and then. One time asked if I wanted to come over and hang out. I did and mom got my virginity.”
-eekkbb172
10
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“I slept with my friend’s mother at a music Fest and was very high on acid. We were all hanging out, me, my two friends who were dating, we’ll call them David and Claire, and Claire’s mother. Claire doesn’t feel too hot, so David takes her back to the campsite and me and her mother are just left to the festival. We get some drinks in, do some dancing, one thing leads to another…and yeah. Afterward, we just sort of chilled in my tent for a few hours before hitting the party tent, having a wee cuddle.”
“Claire actually walked in on us after we had… finished and I was so high I didn’t even really know what was happening, I just knew that I had done something very wrong. So the festival ends and we all go home and of course, the sensible thing to do would’ve been to try to patch things up with Claire and never talk to her mother again. You will find, however, that I am not a sensible man, and proceeded to not only see her again but date her on and off for 4 years. I have, so many stories about those four years.”
-PainIsPleasure
11
“My first serious girlfriend’s mom used to text me every day after me and her daughter broke up. Just friendly stuff at first. Talking about music and other mutual interests and I used her to keep tabs on what my ex was doing (because I was a dumb 16-year-old kid). Eventually, it lead to her telling me how much I reminded her of her high school boyfriend that killed himself and she went on to tell me she lost her virginity to him and how much she loved him, then things took a turn. She started sending very sexual texts which turned into nudes and phone sex and plans to hook up. Eventually, I ended up walking away from it all before anything really happened.”
“I didn’t think much of it back then but looking back at it now, I was a 16-year-old heartbroken boy and she was a 40-year-old married woman. So that’s pretty fucked up to think about now. Basically groomed and taken advantage of by someone I thought was my friend.”
-xLykos
12
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“I hooked up with my student’s mom. I was teaching an after-school program so I saw her almost every week at pickup (sometimes her husband would pick up, yes she was married) and we would talk a lot to the point that we became friendly. Well, I was going through a divorce and happened to bring that up one time and she very quickly gave me her phone number, put her hands on me, she was not being shy about it. Something like out of a movie.”
“Next time I saw her she asked me out to lunch and I said sure. We met up, had lunch (she paid), and she went on to tell me about how her and her husband were not sexually involved with each other and they were free to see other people. We went back to my place and the sex was wild. That was the only time we hooked up though, as I started dating someone shortly thereafter. Her kid was one of those “I’ll fuck your mom” Xbox live kids, so I would just chuckle to myself when I saw him.”
-the_implication_
13
“I had sex with one of my best friends mom. It was Thanksgiving and I was driving her back home and she confessed that she didn’t have sex in years since she was a widow. I told her that I didn’t have sex in months since I was moving. We talked a bit more and we sorta flirted and once we got to her house, she asked me to come inside and we did the deed.”
-Marvel089
14
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“My sister was talking about this one kid I didn’t really care for, and ended up working with him at the job I was managing at. There was a woman working in a different area at that same job I ended up having a one-night stand with her after we had been flirting a bit here and there. Come to find out later that was the dude’s mom. My sister would then use this as a comeback and say “Well your mom sucked off my bro.” Was a weird time several years ago, all kind of moved away after a bit. Nothing much outside of that happened.”
-Rickapacolypse
15
“A good friend of mine had this happen to her back in high school. She caught her (also high school-aged) boyfriend sexting her 40-something-year-old mother and it led to her mom and her stepdad’s divorce. All while she was 17 years old. She still has a strained relationship with her mom to this day, we are 25 now so this happened almost 10 years ago.
I don’t think you can ever get over that kind of betrayal by your own mother… I believe she still has a good relationship with her (now ex) stepdad though. Her mom is now dating a man her age, but she will always be a predator in my eyes that seduces her daughter’s boyfriend. So gross.”
-analphagocytosis
16
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1/4
“Friend’s mom and I used to get stoned together. So when we were at her daughter’s birthday party at her mom’s house, she called me to her room so we could smoke a joint. She didn’t want to do it in front of everyone, and it definitely wasn’t the first time we’d gotten a little high together. So it was somewhat familiar territory. Maybe it was the weed, or the wine, or both, but as were smoking and chatting, I just leaned in and kissed her.”
2/4
“To my surprise, she kissed me back, and we proceeded to make out like a couple of horny teenagers on the love seat in her bedroom. She stopped for a moment, looked at me and said “Well, had I known you were interested we could have done this a long time ago”. We made out a little more, and I told her that we should stop because we’re going to get caught. So we kissed and groped one another a little more, and returned to the party.”
17
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3/4
“The next day she stopped by my apartment to see how I was doing, which wasn’t uncommon. That day was slightly different. She was always a very good-looking woman, but that day she had more carefully applied makeup, some nice-looking earrings and a blouse that showed off more cleavage than usual. I invited her in and we were off to the races. We both had a great time, but I thought of my friend and said that we probably shouldn’t do this again. She didn’t really respond to it and we continued to cuddle for a while.”
4/4
“The next day she called me and said that she thought she may have lost her earring on my bed or my couch, which I thought was BS, but it turns out that the earring was indeed in between the cushions of my couch. She came over to retrieve it and we went at it again… and again, and again. This went on for months until I finally was moving out of state. It never happened again, we never spoke of it, and my friend never found out.”
-TheGoatEater
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