Hooking up with your friend’s parent has always been a taboo subject. In many ways, it’s the most frowned upon act you can commit. It usually involves underage acts, and it serves to destroy your relationship with friends, assuming they find out. There’s also the fact that parents are usually married, which adds a whole new element of disgrace to the act. But despite the fact that it’s so widely frowned upon, many people have gone down this route. In fact, it’s probably a lot more common than you might think. Scouring the web for confessions from these people, I found numerous threads on Reddit that detail these exact stories. And some of them will shock even those who think they’ve seen it all.
It’s worth pointing out, however, that everything said on the Internet must be taken with a grain of salt. After all, we have no actual way of confirming these stories. Because of their explicit nature, almost all of these confessions are written by anonymous users. They don’t want their real names associated with these sex acts. But while it’s not possible to confirm these stories, some of them are undoubtedly 100% true. Truth is stranger than fiction, and you never know what goes on behind closed doors. While we like to think this sort of thing only happens in raunchy adult films, it does actually happen in real life. Think about it. You could know a mom who’s had sex with her son’s closest friends. Or maybe it was your mom…
15. Trophy Wife Got Bored
One guy tells a story of his friend, who started hooking up with one of the neighborhood’s hottest trophy moms:
“Once we were in high school she had just divorced a guy that was a surgeon at a rather large hospital and also worked at a smaller one in the area. They lived in a huge house that had an indoor pool, she got it in the divorce, all she did was lay around the pool drinking all day. A friend of mine that was a grade ahead of us had hooked up with her one night at an after prom party, he was 18 at the time but they tried to keep it a secret but the day after he graduated he moved in with her.
She would buy him whatever he wanted and take him on vacations. She bagged a sex slave and he got a sugar momma it was a win for everybody. This was just a year or 2 before camera phones were a big thing but he always bragged about how god she looked naked and how she could suck a watermelon through a garden hose.”
This apparently continued for years, and the guy who was hooking up with her said that she didn’t want marriage or any commitments, only sex, which is pretty much exactly what every teen guy wants! This sounds like something straight out of an adult film. I just can’t believe it actually happened in real life…I guess truth is stranger than fiction… Or in this case, hotter than fiction!
14. This Incredible Story…
One guy tells the story of how he hooked up with his best friend’s mom:
“My little brother was 4 and was babysat by my best friend’s mom. Most days after school I would go to their house and skate with my friend and at 5 pm, I’d usually just chill in their house and play Nintendo while he was gone. At some point his mom started offering to massage my back while I played.
I let her do it and thought nothing of it. Well one day, she started reaching around a bit and next thing you know I was getting wood. So she asked me if we should move somewhere more comfortable where she could massage me a bit more. I said sure and we went to her room. Well, within 5 minutes it was on. I asked her if she thought Jesus would be mad at us and she said she thought Jesus would want her to be happy. That passed my 14 year old logic test so we kept going.”
This apparently continued for months, as they hooked up everywhere; in the backseat of cars, in their houses, and wherever else they could find solitude. She then started giving him money and promising to take him on vacations. It all ended when the boy told his brother, and then the word eventually reached the authorities, who charged the mom with statutory rape. She was sentenced to a few hundred hours of community service.
13. Her Boyfriend’s Dad Paid Her For It
It’s not just guys that hook up with their friend’s parents. This girl tells a story of how she hooked up with her friend’s dad:
“I hung around with a group of older burnout stoner dudes, and over the course of our ‘friendship’ I slept with/dated pretty much all of them. One of them had a dad who still thought himself young/hip and would come around to smoke pot or give us alcohol.
At some point I was off-again from [my boyfriend], and bored, and this dad found me on some social media platform or another. After awhile he invited me out for a drive–new car or convertible or something.
We drove around, bought beer, watched some TV…and when he started coming on to me I didn’t stop it. I kind of liked the attention, I went along with it, and we hooked up. Afterwards he gave me some money really awkwardly, told me he wasn’t ‘paying’ me he just wanted me to have nice things. Whatever.”
Damn…This story is too filthy for words! Not only did she sleep with one of her friends’ dads, but she let him pay her for it too! I’m not even judging the girl. She was just a young girl struggling with addiction. But for that dad to prey upon a young girl and encourage her by giving her money? That’s really, really, low. This guy obviously never suffered any consequences, which makes you wonder how prevalent this kind of thing actually is.
12. His Girlfriend Cheated On Him With His Dad
This guy tells a story of his girlfriend ditching him for his own father:
“I met a woman. We started up a relationship. After a few months she met my father and they (apparently) hit it off. She broke up with me citing religious reasons (going back to Mormonism). In reality she had been cheating on me with my father for a while (yes he knew).
Shortly after she broke up with me, my father called me cause he couldn’t access his email. When it loaded up, I saw a summary line on an email from her to him saying ‘I can’t believe the way you touched me last night.’ He could tell something was wrong and shouted at me to get out of his email.
I hung up and realized I wasn’t in a safe place, mentally, so I drove to my therapist’s office and sat in the lobby waiting for him to come out.”
No kidding. If I was this guy, I would need to see a therapist too! Can you think of anything more humiliating and crushing than finding out your girlfriend had been cheating on you with your dad the whole time you’d been dating? Wow, I’m surprised this guy didn’t kill himself after this. Obviously his relationship with his father was completely destroyed after this.
11. She Broke Up With Him – Her Mom Stepped In
This guy tells a story about how his ex-girlfriend’s mom helped him get over his relationship in a very “special” way:
“17-18 years old and I’d finally got the girl of my dreams who had friend zoned me for years. I was the rebound guy and as such didn’t last as BF. I swung by one evening and my ex was getting ready for a night out with her new beau who happened to be her ex beau prior to me.
Her mom could tell I was upset and offered me some wine. It was awkward. For me at least. Don’t get me wrong, it was hot, but I was used to younger girls and she wasn’t exactly young.
Very attractive and aggressive but I don’t think my youth could keep up with her needs. I gave it my all and that was that. I don’t think ex ever found out to my knowledge. I’d been back a couple times since and always wondered if that look in her moms eye was a ‘yeah we f**ked’ or if it was ‘I bet you’re much better now.'”
Well, that’s one way to get over a failed relationship. I know I would probably feel much better about the whole thing if I could look into the eyes of my ex-girlfriend while secretly knowing that I’d hooked up with her mom. That kind of knowledge gives you a sense of power. Hopefully it made him feel better about the whole thing, although it was probably really awkward as well.
10. This Can’t Be Real…
This is a story of a 15-year-old girl who started hooking up with her dad’s friend… And her parents were okay with it:
“In high school I developed a crush on my dad’s friend. I would flirt with him any chance we got, basically throwing myself at him. Eventually he got the hint and we started texting and secretly meeting up. He said if we did anything we needed my parents’ approval first. My parents are pretty chill, relaxed and open about sexuality but I wasn’t sure that was a good idea.
He came over and talked to my dad for a while, when I felt it was safe to come down, I explained how I felt to my dad. He said if it was serious he would think about it. Two days later he came to me and told me it was fine, under the conditions that we only met at our house and didn’t do anything sexual until I was of age. So at 15 I started dating my dad’s 43-year old friend with their approval and at 16 we started being sexually active.”
This is one of those stories on the Internet that I have a hard time believing. But it’s probably true. I just can’t believe that her parents were actually okay with this! If I was her dad, and I knew that one of my friends was hooking up with my daughter on a regular basis, I’d probably go insane. I know that she says her parents were “open about their sexuality” but isn’t this going a little bit too far?
9. Her Best Friend’s Dad Got Her Pregnant
This girl tells the story of how she was knocked up by her best friend’s dad:
“I was at a leaving party for my best friend’s brother who was heading off to Australia for a year. After the pub the party continued on to my best friends house, everyone had gone to bed and I found myself alone with her dad. We got talking and then he leaned in to kiss me, I didn’t resist. One thing led to another and before I knew it we were having sex on the sofa with the rest of the family asleep upstairs.
That was two months ago, I have seen him since and he completely pretended nothing had happened between us. He continued to act normally around his wife and daughter- he even went as far as kissing his wife good bye as he left the house. It gets worse, I found out last week that I’m pregnant.”
Wow. This girl is definitely in one sticky situation. It’s bad enough that she had sex with a married man. And it’s pretty terrible that the man just happened to be the father of her best friend. But the icing on the cake is that she managed to get herself knocked up by this man. She also says that abortion is not an option for her…which basically means that all kinds of drama is going to come out of this little debacle. I feel really sorry for her… It wasn’t her fault and now she’s probably going to end up being a single mom that the whole neighborhood hates.
8. Lost His V-Card To His Hot Friend’s Hot Mom
“One of the girls in [my] group was considered to be one of the hottest girls in school. Right before our sophomore year her mom asked me for some help with purchasing a new computer.
It was also not very clear to me that the mom had a crush on me. I got there an hour early on purpose so I could hang out with the younger sister. Payed off, me and the younger sister ended up fooling around for about 30 mins before her mom got home. Once the mom was home I looked at the computer, realized what was wrong and had to leave to get a replacement part.
I got back later that evening around 7 PM. No one was home except the mom. So I decided to give her a hug and comfort her and it instantly went from hug to kissing and clothes started to come off. She f**ked my brains out on the living room floor/couch.”
Apparently this continued for a couple years until he finally ended it in his senior year of high school. During this time, he said that he learned a lot about sex and how to please a woman. This is probably one of the craziest stories, because this dude managed to hook up with the mom and her daughter during the same night! That seems like something straight out of an adult movie, and he basically lived the fantasy of a lot of guys out there.
7. Friend’s Parents Take Him In, He Sleeps With The Mom
This guy didn’t just sleep with his friend’s mom, he did it after her and her husband were kind enough to take him in:
“I had gotten to know a female friends parents from some sporting events I had gone to and they offered basically to take me in.
I was like the son they always wanted but never had. They did everything for me. I spent a TON of time with the mother and we did really have a great time together. One night after some drinks we were in the kitchen the father had gone to bed and she just grabs my face and starts kissing me. I don’t know what to do other than kiss her back. A few days later while cleaning her daughters room it happened.
We got naked and had sex on her daughter’s bed, it was clear she had been waiting for this moment. Pretty soon I realized what I had done. This guy had taken me in, let me stay in his house, gave me a job and health care. And how do I repay him? I sleep with his wife. Still to this day it haunts me. I have no relationship with the family as a result and it eats away at my heart.”
Apparently the mom was thirty years older than him. Which is kind of gross, any way you slice it. And this is obviously one of the sadder stories, in which betrayal is a key theme. But can this guy really be blamed in this situation? He was just a young guy, and the mom knew exactly what she was doing. I just feel sorry for the father…
6. She Hooked Up With Her Friend’s Dad
This girl hooked up with her bff’s dad during a birthday party:
“Obviously I’d known [my bff’s] father Michael for years and I always thought he was sexy, and not in the ‘oh he would of been hot in his youth’ kinda way, he was a f**king fox, but obviously this is just one of those things you think about and dismiss as a ridiculous immature fantasy, or so I thought.
Anyway, it was Cassie’s 21st birthday dinner that her dad had organized for her family and close friends at this massive restaurant he hired out at a hotel. During the dinner, I was sat next to Michael and I started experiencing all those stupid thoughts you have when you’re almost touching someone and it feels like you can physically feel the energy between your bodies.
I was out in the corridor and I contemplated knocking on his door and just as I’m about to go back to my room and remember that I’m drunk and stupid for evening thinking this could happen, when he opens the door. We barely said anything the entire time and it was really sensual and peaceful, like getting to know each other for the first time in a completely different way.”
This is another story that doesn’t seem too scandalous. I mean, obviously the girl was in her twenties, and it wasn’t like she was still in high school or anything. And for both people it seemed like a consensual thing that was genuinely special for both people. I guess we shouldn’t pass judgements on people’s relationships just because of their age…
5. His Friend’s Mom Was Better Than High School Girls
This guy started doing chores for his friend’s hot mom…and one thing led to another:
“When I was a teenager I was friends with a guy that had a pretty hot mom. She was thin, blonde, freckled, B-cup…….the mom that every guy my age would talk about. She needed help around the house getting the grass cut, skimming the pool etc. so she would pay me to do a bunch of the yard work.
One day she invited me into the sauna in the basement after she had a few glasses of wine. She had her legs open enough for me to just barely see her crotch. The she asked if I wanted to see what was under the towel. I nervously said OK and she dropped it to reveal a 10/10 smoking body.
She started to play with me and then went down on me. It was way better than the BJs I got from inexperienced 16 yr old girls. So for the next two years of high school I banged her twice a week, despite having a girlfriend on and off the whole time.”
Wow. Out of all the stories on this list, this is the one that seems like it was taken straight of a kinky romance novel. When I read this, I’m reminded of the music video for the song, “Stacy’s Mom.” Anyone else get that vibe? One thing’s for sure, if this story is real, then this guy had one of the most legendary youths any teen could hope for.
4. It All Started With A Back Massage…
This person talks about the time he hooked up with his friend’s mom:
“It all started when she asked me to crack her back. A few weeks of flirting here and there thru texts and we get to the night where she messaged me and said she wore some revealing shirt. I was currently living with them at the time so I replied with ‘show me’ which she responded with ‘well you aren’t here.’
I got there and knocked on her door and she came out wearing a robe like she just got out of the shower. She ended up laughing and undoing her robe and showed me her nightie. She ended uncovering herself again and this time I asked if she can show me her rack. I reached over and started rubbing on them. I could tell she was enjoying it so I unzipped my pants and let her have some fun of her own. Then she said we shouldn’t be doing this out here, so we went inside the room and that’s where the rest happened.”
Wow! That’s another story that definitely makes you wonder if he’s telling the truth. But if it’s true, then this guy had quite a story to tell his friends at the end of the day. This kid joined the exclusive ranks of the teens who have managed to have sex with their friend’s moms. It’s a small, exclusive group, but membership guarantees you legendary status with your friends.
3. He Wants To Tell His Friend…
This guy had sex with his friend’s mom, and has been struggling to keep his mouth shut about it:
“I was 25 she was 45. I have three friends who live in a house together on a well known lake. I attended a 4th of July party two years ago. My friend’s mom was there, we were the last two up at the end of the night and that’s when the magic happened. We slept in a spare bedroom and in the morning she rolls over and asks ‘are you ready for round two?’ My friend has never found out. She said ‘make sure that condom is on, I don’t trust those things, that is how [my friend] happened.’
One time I have almost let it slip out. He tackled me on a boat dock and cut up my back up pretty good. I wanted to say ‘It’s cool dude, I f**ked your mom.’ It will happen one day, I just need to be sober and clear headed to duck the right hook that is sure to follow.”
This brings attention to the whole humiliation aspect of having sex with your friend’s mom. Is there any greater insult than the knowledge that one of your friends has banged your mom? It’s one thing that is totally unforgivable, and can turn friends into the biggest of enemies. So far, this guy has managed to keep his mouth shut about it, but for how long?
2. Slept With A Dad Who Had An Open Relationship
This girl tells a story of how she had a relationship with a friend’s dad who was in an open relationship with his wife:
“So.. my story is kind of applicable… I rode the bus with and was friendly with two younger kids (boy was 10 girl was 6 or so) that rode my bus when I was in high school. After I graduated high school I started sleeping with their dad on and off for a while. His wife knew (they had an open relationship) but I highly doubt the kids knew or anything.
After about three months of it, we were at my parents house one day (was supposed to have the house to myself for the afternoon) and my mom came home early and caught us in the middle of the act. This was 7 years ago and I still get the occasional lecture from my mother about being a homewrecker as she is convinced that it was an affair and the cause of their divorce that happened about four months later.”
While this story is still pretty kinky, it’s not as bad as the others. Why? Because the wife knew what was happening and was okay with it. Although it might be weird for some to wrap their head around, this sex act is probably more acceptable than the others on this list for that very reason. And the girl also remembers it as a positive experience, where she was able to learn a lot about sex. And no one’s feelings got hurt!
1. The Other Side Of The Story
We’ve heard stories from the friend’s perspective, but what about the perspective of the son whose mom did the hooking up. This son tells a story of how his friend banged his mom:
“I was having a chill night at home with my girlfriend, my friend, and my mom. We were all getting a bit frustrated about that and my girlfriend could tell so she told me to just go to bed and forget about it. Which left my mother and friend alone upstairs.
Fast forward a few hours later, in the middle of the night. As I am starting to come to, I realize some sh*t is weird, my friend comes downstairs and passes out on the couch, I go upstairs and my mother locked herself in the bathroom. My gf looks at me and starts to cry and tells me that for at least 10 minutes before I woke up she heard banging noises upstairs, similar to noises two people f**king would make.”
Apparently his friend felt so bad about it that he later attempted suicide. This raises an important point. It may seem like it’s a laughing matter when moms or dads decide to have sex with their kids’ friends, but it can often lead to disaster. Love works in mysterious ways. And at the end of the day, we just have to accept that we are totally enslaved by our urges.
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