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*cked.
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*ckfest 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*cking 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*ck 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*cked 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 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 f*ck 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*ck.
That turned into a “relationship” for about 18 months.
One afternoon my mum is telling me how sh*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 sex 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*ck 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
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.