Maybe one of the weirdest hits of the 2000’s came from a quintessentially alt-rock band called Fountains of Wayne called “Stacy’s Mom”:
Stacy’s mom has got it goin’ on
She’s all I want and I’ve waited for so long
Stacy, can’t you see you’re just not the girl for me
I know it might be wrong but I’m in love with Stacy’s mom
While we were all singing this song in our jokey ways, real world “Stacy’s mom” scenarios were playing out.
So how does life imitate art? Reddit has stories.
1. Tough times.
Friend’s mom going through some tough times with her husband, “accidentally” added one of our friends on Facebook, she started flirting with him and eventually they f**ked.
After this kept going on for a couple of months, dude decided to tell his friend (son) about it, at his house.
The son cried, they threw hands at each other and everything was alright moments later.
Don’t really know what happened after that, lost contact with both of them.
– antoniocmf
2. Right next door.
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 f**kfest 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
3. Absolutely wasted.
I got super f**king drunk at the friends 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.
We did recently reconcile, I sent a long text a couple of months back apologising and letting my friend know how much I missed them, they then recently reached out because they found out I’m expecting my first baby, I’m very happy to be back in contact with this friend.
Tip for everyone, don’t sleep with your friends parents, it’s a d**k move. But should that ever happen and you want to keep this friend a friend. Own up, apologise and then give them space.
The truth is always better than a lie, and your honesty and apology will be appreciated
– Sharkary
4. The inevitable.
A friend of mines 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
5. Losing it.
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
6. How it started…
My first serious girlfriend’s mom used to text me everyday 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 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 f**ked up to think about now. Basically groomed and taken advantage of by someone i thought was my friend.
– xLykos
7. Bad teachers.
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 pickup, 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 s** 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 f**k your mom” Xbox live kids, so I would just chuckle to myself when I saw him.
– the_implication_
8. Technically legal.
Had sex with my ex-girlfriend’s mom in high school (I was 18, so it was technically legal). She recently became a single mom just a year or two prior, and you could tell she was really trying to “get out there” more. Very good looking, not even just for her age. Worked in real estate, but I don’t think she liked to mix things up with work/clients. Which I think was hard, because she was very successful in the area.
Anyways, her daughter and I dated over a year until we broke up. I went over to retrieve some of my stuff. My ex girlfriend wasn’t there, because she “couldn’t stand to see me” so it was just her mom and I. She was overly friendly, but not acting out of the norm until I was leaving and she said “If there’s anything you ever need at all, please call me.” I thought that was weird, but we exchanged numbers and I left.
A week or two later, she began texting me. Eventually she invited me over to watch movies. Again, I thought that was weird and was some sort of ruse to get me over there to reunite the relationship with her daughter. But then she said she said her daughter was staying at her sister’s and she was “so bored she might finish this wine bottle all by herself”. A few drinks actually sounded good and getting booze at that age was hard, so I agreed.
I’ll spare you the details, but it didn’t take long for it to happen once I got there. It was a great time, but I wasn’t exactly proud of it because I was going through a lot at the time, as was she. I kept it to myself and never told anyone. We met up another time but had to be quick to avoid her daughter who was set to get off work soon, and after that I realized I didn’t want to do it anymore. And a few weeks later, I shipped out for the military and left my entire old life behind anyways. We haven’t spoken or seen each other since, now 10 years later.
– Dusttyy
9. Even Margaret?
My mum had a friend, and I was friends with her son. I had turned 16 in November, and went to their house for a party over christmas. I got drunk and passed out on the couch in the living room.
I woke up to the house empty, apart from my friend’s mum sucking my d**k.
That turned into a “relationship” for about 18 months.
One afternoon my mum is telling me how s**t I am, and how none of my friends can be trusted, so I asked her if she could trust all her friends. When she says yeah, I asked “even margaret?” And then the truth came out. Most of truths anyway.
Never spoke to my friend again, but I did have to fight some drug dealer friends of his. Apparently margaret came round to my mum’s house the day after and got a mouthful of abuse. I don’t know what was said, but I’ll guarantee that it was more about the breach of trust between her and my mum, and less about the sexual assault.
My mum has never really forgiven me for it.
BTW, I’m UK and age of consent over here is 16.
– Bigjobs69
10. No pride.
Well, I was a horny guy, and my friend’s mom was… well, available, really.
I’m not proud of it, it just kind of happened sometimes, and every time I felt shame. I don’t know, like I was betraying my friend’s trust?
Worse thing was, she was actually a friend of my mom too, so I kinda saw her on a regular basis….
– anroroco
11. Pretty awkward.
Not really an ex but an ex coworker i worked with in college. We worked late shift together and had s** multiple times in my dorm. Didn’t know her mother worked dayshift and had a married last name that she kept.
So i later like 1.5 years later went on to work dayshift not knowing that was her mother and they were aged 18 and 34 so i never thought it could have been. She also made sure not to tell me it was her mom because she said thAt conversation would be awkward.
So yeah i end up sleeping with her mom as well as her. Neither of them to my knowledge know that i slept with the other and i wasn’t willing to tell them.
Havent seen either of them in years btw. I graduated and moved.
And for those wondering, the mom was better.
– Caedo14
12. Bullet dodged.
Not the same, but my friends dad was released from prison and then was sending me DMs. He was in his late 30s, and he’d try to get me to meet up with him. I was 15.
My friend never told me why his dad was in prison, but a few years ago I googled it and it turns out he was locked up for sexual contact with a minor.
I was lucky I didn’t meet up with him.
– NighthawkUnicorn
13. Coffee, tea, or?
I slept with my mates mum.
We were mates all through primary school and high school, played footy together etc.
During high school they moved fairly close to us after his parents got divorced. Over the next couple of years we caught the bus to and from school together and his mum would wait with us in the mornings and we would sit at a cafe nearby to have a coffee. Even on days when he was sick and wasn’t going to school, she would still meet me for coffee.
He would regularly have parties at his place on weekends, mainly because of the divorced parents and his mum kind of let him have free reign as a result. On those nights I would hang out with her, have a drink together, chat as she was more interesting to me than the girls my age.
After high school was over my mate and I stopped hanging out but every now and then I’d see his mum at the local shops etc cause we still lived near each other. One day when we bumped in to each other we decided to have a coffee like old times, after we agreed to do it again. Started meeting for a coffee every now and then. After a time the coffee was being had at her house rather than at the Cafe.
– BigMelbGuy
14. Nip it in the bud.
I went to a party with a friend who introduced me to a young lady a couple years older than me, we kinda hit it off with conversation. She explained to me how her and my friend knew each other and how frequently he’d hang out at her house. Explained how here and her Mom basically lived alone because her Dad was bed ridden on a machine in one of the upstairs bedrooms.
Long story short, she came home early one day to find that my friend was there having relations with her Mom.
That pretty much ended our newly budding romance and my friend is now heavy into the church.
– Scandal929
15. Long story short.
Well, I don’t get chance to tell this often so f**k it.
My bestfriend’s (at the time) mom.
It was new year’s eve, I was 19 she was 40.
I was the super close family friend that was always there. Let it be known she was a warm from the get go always flirting and making jokes and she was the milf out of the group of friends.
Long story short, we were drinking before we went out at their place with some of her friends (she was having a party, we were going out). Anyway the night goes on, I end up by myself and walking home, instead I went to (let’s call him pete) Pete’s house, his mom was still up with one of her mates.
I turned up with another bottle and proceeded to drink with them. Her friend left and i stayed, waiting for pete. I sat next to her and before you know it my hand is on her leg, she said to me “I’m petes mom” I said “I know” with the biggest smile on my face and she grabbed my hand and we both went upstairs and it was just like that, best night of my life, it was like a porno for me at that age and I won’t forget it.
– nam_sdrawkcab_ehT
16. Double trouble.
I have slept with two of my Moms 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. Next thing I know we’re drinking and we ended up having s**.
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
17. A knock out.
My brother’s best friend from highschool dated my Mom in his 30’s.
She had my brother really young, when she was barley 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 brothers friend left the house, and got into his car. My brother followed him out, and punched him in the head though the driver side window.
He managed to go through the window and still connect with enough force to knock him out cold.
– Knytemare44
18. A connection.
I was at a friend’s birthday party. My friend was in her mid 20s, I was 30, her mom was in her early 50s. She and her mom took really good care of me after my father passed. They made sure I was eating and that I actually left the apartment every day, as I was prone to just sit around being a depressed sad sack.
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. 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.
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.
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.
Sadly, my friend’s mom passed five years ago. I’d thought about telling her but it just seemed like a bad idea
RIP Julie. You were smoking hot and just an all around great woman.
– TheGoatEater
19. The betrayal.
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 step dad’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) step dad 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
20. The incident.
When I was 20, I got accepted to university in Canada (I’m a French guy) and my mum put together a BBQ to celebrate it with my best friends, among which was my actual best friend (girl my age), who lived far so she would stay the night.
My mum and dad were already getting divorced and sleeping in separate rooms back then, so there was no doubt they will ever get back to normalcy in terms of their relationship.
After most people left (and I was drunking my way around talking about Canada with another friend), my (now former) best friend and my dad made sure my mum went to bed and carried on drinking together.
All I remember after is me trying to figure out where the hell my friend was in the morning as the guest room was empty. It took so much fighting denial to realize she had been sleeping with my dad all night… Mum was destroyed, so was I, they both denied it and said they « just talked ».
I still cannot believe this happened but with retrospective my dad has been such a crap dad to his kids and wife and that friend has not been nice to me either.
– Dodopilot_17
21. Hindsight.
This reminds me of the mom of my cousins wife.
When her kids were younger they used to bring home kids from school that had it really rough in their life. She would talk with them and help them, but one thing that was interesting she mentioned was that she was glad to have parrots around who would initiate physical contact with them.
She said she knew these youngsters needed physical contact since some of them had been feeling lonely or mistreated for a while, but she said she couldn’t be the one giving it to them.
Now reading these comments, I understand what she meant by that.
– charlyhyacinth
22. Too high.
I slept with my friend’s mother at a music Fest 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. Afterwards 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 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
23. A dry spell.
I had s** 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 s** in years since she was a widow.
I told her that I didn’t have s** 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
24. Confessions.
A friend at school’s mum was pretty hot. She was relatively young compared to most of our mums and his Dad was quite a bit older and absolutely minted.
When we were young teenagers it was a bit of a running joke to give him s**t about his hot mum or how his Dad was her sugar daddy.
Fast forward to the end of sixth form (end of high school for US readers) when we were all 18 and he was having a party at his massive house to celebrate. Most people were outside getting drunk in the garden but I’d had a bad few months (family stuff) so wasn’t really feeling it.
I decided to go and chill inside for a bit and in the kitchen I found his mum just drinking wine and looking forlornly out the window. I asked if she was ok and she pretty much unloaded her issues! She was miserable, she hated his Dad, she’d settled down without having a life first, felt trapped because she couldn’t afford to leave, loved her kids etc.
I opened up about my issues too with my family and it actually felt good to talk to a relative stranger about it. I now realise I should have been seeing a therapist.
Anyway one thing led to another and she started making out with me. I didn’t stop her. She then led me upstairs and the rest is history.
On the one hand, it was pretty awesome, she was smoking hot, I was pretty inexperienced, and she really knew how to communicate in the bedroom. On the other hand though, I knew I was betraying my friend (and f**king up his parents’ marriage) plus I could hear all my friends laughing and partying outside!
A few months later they got divorced and I understand she got a bit shafted in the deal because she’d cheated on him. I don’t know if that was me or she did it with someone else too.
I am pretty ashamed about it but I also realise she was using me too. I was never under any illusion we had some special connection or anything but I can see she just wanted to f**k someone out of catharsis or frustration and maybe, subconsciously, to force the problems in the marriage into the daylight so she could finally get out.
– WindowSteak
25. Knowing better.
I had sex with a good friends mom.
Looking back, it’s really messed up. She had been working on me for months. I was only 18. I’m ashamed of it, fortunately the friend never found out.
But as an adult, I now look back at it and realize that I was in over my head and she should have known better.
– mustang-and-a-truck
26. The comeback.
My sister was talking 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 women 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 dudes 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
27. Curious samples.
Interesting that the top twenty or so comments are younger male with older female (and one older male).
Is that really that much more common, or is it more that young men like to brag about it while a woman feels shame for hooking up with a dad?
– thentil
28. The jackhammer.
I slept with a childhood friend’s dad while visiting my hometown. Long story short he’s bi and divorced and I was browsing on a gay hookup app (it’s a small countryside town so the only things to do are ketamine, sex or leave), he messages me and he clearly doesn’t recognise me because I don’t look the same as I did a decade ago. I recognise him and the entire time i’m thinking “this is really weird” but i’m bored and he’s relatively handsome and charming (as far as charming goes on Grindr lol) so I figure hey why not.
And hindsight is 20-20 because the sex was fun but the entire time i’m thinking “this is my friend’s dad he has literally driven me to school before”. Just left an overall odd feeling.
My friend doesn’t know and it’s going to stay that way because we don’t really talk whatsoever now and it’d be weird to just pop up like “your dad jackhammered my prostate and it was kinda weird”.
– lillimarleen
29. A fun party.
This kids mom at his graduation party I went to high school with.
His parents were rich and it was well known his mom was decent looking and dressed like she was in high school, but this kid always only had his close friends at his house, until his graduation party.
My close friend had a twin sister & we always partied together and she wound up with an older kid who had already graduated but he was cool and always hung out with us. So he comes to the grad party with us, long story short the older kid was found pants down with the drunk mom bent over the bathroom sink.
The kid who’s party it was, and the dad went NUTS and chaos ensued.
The older kid hit the grad party kid and took off.
I heard that the mom wound up sleeping with another kid we went to school with a couple years later and they got divorced.
I’ll never forget that chaos though. That was a fun party.
– Keithm1112
30. Support groups.
Met this guy at the beginning of college. Dated all through college. Anyways my boyfriend at the time (the son) became super controlling, manipulative and borderline abusive, which all came to a head when his parents years long divorce was finalized.
Dumped the boyfriend, he moved out of state and the dad still lived close by. Stayed in contact with the dad and many other people from his family. Eventually the dad asked how my dating life was an I took it as an opportunity to complain about how I was having a hard time finding people who I had sexual chemistry with. Turned into a conversation about kinks and eventually (over a few months) the tension just kept building.
To be blunt. We were both h**ny, lonely and knew the other person was into the same things so we started a fwb type relationship. Helped that the dad was young and aged wonderfully.
Eventually it ended, on good terms. We both met other people. We both pushed the other to date other people. Find something long term and more fulfilling than cheap s**.
From what I know no one knows, I never told and he didn’t either. We were just lonely, needed some s** and wasn’t about to have casual sex with randoms. Might as well be someone you know that will be happy for you once you find the right relationship. Ya it was slutty of me and maybe I’ll regret it in the future but at the time it was amazing s** with a good looking person I trusted.
And and FYI the dad never hit on me while I dated the son. To my knowledge anyways.
– throwaway5419475
Sounds like it can be a whole lot messier in real life. Who knew?
Have you had experiences like this?
Tell us in the comments.