It is time to learn about something that is completely terrifying: your friend actually sleeping with one of your parents. And if it hasn’t happened to you, be thankful, but you bet your ass that it has unfortunately happened to the folks below. As usual, we have to give thanks to AskReddit for reeling in all these confessions from men and women who have revealed that they have actually hooked up with their friend’s parents. And while some liked it and kept it doing, others felt complete and utter guilt. But when it comes down to it, it still occurred. Check out some of these crazy confessions – You will not believe #21!

1. My friend’s mom had always told me how cute she thought I was

“My friend’s mom had always told me how cute she thought I was, and would joke about how she couldn’t wait until I turned 18. I would flirt back occasionally and one night we did some “hand stuff” while my friend was sitting 3 feet away, she never found that out….So the day before my senior year in high school I decided I didn’t want to be a virgin anymore. I text her and ask if she wants to hang out, she says sure and picks me up in the family minivan. We drive a little ways away, put the seats down in the back, smoked a bowl, listened to Kid Cudi, then we fucked….I got the best head I’ve ever had to this date, and there was no awkwardness afterwards. We even hooked up a couple more times.”

2. Sex With a Friend’s Father

“I had sex with a friend’s father…. I think he was in his early 40s? He looked pretty young. He was sending out the vibes that he was interested and I was flattered. He had a handsome distinguished kind of look and I’ve always been a sucker for that….We were out on a friend of theirs’ boat for an afternoon. We were drinking and having a great time. I was wearing a very small bathing suit. We were all in the water having a great time—probably 7 or 8 of us—and having a water fight. He kept trying to dunk me. He’d have his arms around me and I’d shimmy and shake and squirm and he was hard as rock. When we got back to their place that afternoon my pal decided to have a nap….Fortified with some liquor I changed into my fanciest bra and panties and I strolled into his room and asked me if he wanted me. He said yes. He was fantastic in bed and we continued to have sex on/off the next few weeks.”

3. I was 16 at my Friend’s House

“I was 16 at my friend’s house. Whilst they were outside drinking beer through a hose I was inside my friend’s mum’s bedroom just chatting. Don’t remember much, but I went to kiss her and she pulled back and looked at me, got up and locked the deadlock on her bedroom door. That’s when I knew it was on like Donkey Kong. Best thirty seconds ever!!”

4. Sex For A Year

“I fucked one of my best friend’s moms for about a year. Her husband was cool with it, and a bit jealous she was doing an 18-year-old and he wasn’t.…Because I was out of school, and an employee, her son never put two and two together. I would travel with her, and stay in hotels with her, so it was the perfect cover. I don’t really know how it started, but she and I hit it off. She asked me once if I wanted a blowjob or to be made love to. She’s the only woman that has ever successfully sucked me off to completion. It was fucking wonderful. Most awkward moment was definitely when she said “That’s where ‘Johnny’ came from!” as I stuck it in her box.”

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5. Sex With Girlfriend’s Dad

“Was just getting on hookup websites, and seeing the vast amount of men out there who also like men. Ended up fucking my girlfriend’s Dad. Never told her, years later (she’s the type that’d find it hysterical). Bonus story, she was a lesbian, I was gay, both of us used each other as covers without realizing.”

6. First Threesome

“When I was 18 but still in high school I had a threesome with a married couple I met online. My first threesome! We had good fun, so I came back over again soon for more of it. After the sexy times had ensued, I glanced up at their living-room wall and saw school pictures of a girl I knew (not exactly friends, but acquaintances) and had been in the school system with since middle school. Dawning realization of horror…”

7. It was phenomenal

“I was close with two females (sisters) when I was younger (17-22) and their mother was very attractive and looked like she was of their age. One night, during a small party at their place, the mother asks if I would drive her to the gas station to grab some mixers for our alcohol (she was the type who would hang and drink with her children and children’s friends). I oblige, and on the way back she flat-out asks me if I want a blowjob. I respond, “UM SURE.” She proceeds, and I make sure to drive extra slow to prolong the experience, which is surreal. That was that, and we acted none too oddly back at the party. Later that evening as people start falling asleep and whatnot, she grabs my hand and pulls me into her bedroom. Door locked behind us, we have sex. It was phenomenal.”

8. Her Husband Never Found Out

“When I was 16 I had this girlfriend in high school. Her mom would always flirt with me, etc. When that girl broke up with me, I was heartbroken and her mother called me to ask if I was OK and if I wanted to get some coffee. A few hangouts later, she used me like her boy-toy for a few months and her husband never found out.”

9. Graduation Party

“I have a friend that’s a few years younger and went to her graduation party. While there I hung out with her and her family (whom I had known for ages) and commented to her mom (whom we will call Anne) was looking good. Anne had started working out and was looking fit after her last relationship ended….So that summer I dropped by a little more frequently, and sometimes I happened to come by when my friend was at work or otherwise away and just hung out with Anne. It worked out well for a summer.”

10. Constant Fear

“I’ll tell you something, it sucks!!! I have to live with the constant fear that her sons, all of whom I am friends with, will find out. On top of that, one of the only two people besides me that knows about this is sometimes blackmailing me, threatening to blow my cover. I live in a small town, and if this comes out I’m a dead man. However, despite all this; was it worth it? Hell, yes.”

11. Parents Had Just Broken Up

“His parents had just broken up, but for some reason she stayed temporarily while her new BF got an apartment. Saturday night, bonfire. Drank too much, stayed up late. 2am, smoking alone and she came out. Nothing weird BC she is a smoker and a night owl. Stood next to me before asking to sit on my lap. I made eye contact with her, and she just started making out with me. Ended up fucking her in my friend’s bed while he slept on the couch. I vowed to never speak of it again.”

12. Subtle Hints

“I was about 17 or 18 at the time and I always noticed my friend’s dad giving me subtle hints that he was interested in me….One day when I was hanging out with my friend, he actually went out to do a quick errand for his dad. So it was just me and his dad at home. He came by the room I was in and started talking to me while sitting one foot away from me. At the moment I felt very turned on, especially since he made me feel so comfortable. We ended up making out for a bit (I’m not sure how that happened), and we ended up doing it in his office quickly (doggy style). It lasted maybe like 5 minutes, and after that I was extremely weirded out. I never went over to my friend’s house after.”

13. Emotions of Pleasure

“When I was 17 years old I started sleeping with my (at the time) recent ex-girlfriend’s mom. It all started one day when we were hanging out at her house and she asked if I wanted to ride over to her mother’s (my ex-girlfriend’s grandmother) house to feed her dogs seeing she was out of town….While on the way everything seemed normal until she put her hand on my leg. I was caught a little off guard, but we were close so I didn’t really think too much of it. We continued down the road in a void of silence when she slides her hard up to my belt and starts unbuckling it and unbuttoning my pants. Next thing I know, she is out of her seat and on her knees in the floorboard delivering a pretty fantastic blowjob. We get to her mom’s and she grabs me and pulls me into her mom’s room and pushes me on the bed. At this point I’m pretty freaked out. I’m 17 and this is a lot to take in….After a few minutes she took off her pants and crawled up to where she was straddling. As I lay there I am being flooded with the emotions of excitement, horror, guilt, and pleasure.”

14. I was 24 his mom was 51

“I was 24 his mom was 51. She was a very nice lady that had been divorced about 6 months. She was lonely we slept together twice. To this day he doesn’t know. It’s been a few years now and his mom and I act like nothing ever happened. We golfed together a couple weekends ago. So nothing changed for us.”

15. The girlfriend wasn’t there, but her mom was

“My dad at age 15 went to his girlfriend of the time’s house. The girlfriend wasn’t there, but her mom was. While he was patiently awaiting for his girlfriend’s return, the mom pulled a Mrs. Robinson and made a move on him. This is how he lost his virginity. He then leaves and makes some excuse over the phone to his girl as to why he left. Well, he came over the NEXT day and the girlfriend decided it was time for them to take it to the next level. He then proceeds to “lose” his virginity with her.”

16. She was 40ish, he was 18.

“Good friend’s aunt. Not me, but I was in the group of friends. She was 40ish, he was 18. He bragged about it a bit until we laughed at him. She was at that age where she wanted to be reassured that she was still pretty. We sometimes see her and her husband at family events. He probably found out about it, but seems to have accepted it. She is courteous, but not over-friendly with us anymore.”

17. I hooked up with a pretty close friend’s aunt one night

“I hooked up with a pretty close friend’s aunt one night. I’m also friends with the girl’s mom, the sister of the lady I hooked up with. She was on the couch in the living room. It was an awkward morning.”

18. Fucking terrible

“Fucking terrible. It was only my second ever time having sex. She started going down on me and I blew my load within about 30 seconds. She laughed at me (thanks for that Lois) and said “don’t worry sweetie, you’ll be reloaded in a few minutes”. So after munching down on her hairy, tangy pussy for a few minutes I was ready to go again. I came 30 seconds later. She laughed again and said that maybe she chose the wrong friend.”

19. Her husband was cool with it

“Obviously a throw away… I fucked one of my best friend’s mom for about a year. Her husband was cool with it, and a bit jelous she was doing an 18 year old, and he wasn’t. I’m going to be a bit guarded with details, but she ran a business that involved traveling around parts of the country and I was employed by her. Because I was out of school, and an employee, her son never put two and two together. I would travel with her, and stay in hotels with her, so it was thr perfect cover. I don’t really know how it started, but she and I hit it off. She asked me once if I wanted a blow job or to be made love to. She’s the only woman that has ever successfully sucked me off to completion. It was fucking wonderful. Most awkward moment was definitely when she said “That’s where ‘Johnny’ came from!” as I stuck it in her box. It’s been almost twenty years now. You know that saying about older women really knowing what they’re doing? Totally fucking true.”

20. Super Hot Mom

“I had a good friend in high school whose mom was super hot. I mean… SUPER HOT. Everyone knew this, it was known. Anyways, she was single and always seemed real flirtatious around me. Once I told her a joke in the kitchen, and she touched my arm and sort of leaned in and her titty grazed my elbow. It was amazing! I came for 45 minutes.”

21. I Had a Threesome

I had a threesome with my friends mom and her friend piss ass drunk while my friend and his younger brother were there. She bought me plenty of booze and her and her friend talked dirty to me all night. Woke up butt naked in her room the next morning, manage to play off that I just fucked the moms friend and got out of there scratch free… or so I thought.

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Turns out, a lot of people slept with his mom, one of my friends even got a rim job from her, and bragged to the wrong person. A while had passed, and the younger brother of the mom got in a fight with one of his friends, and how I imagine it, his friend instead of throwing punches, threw the most truthful your mom jokes anyones ever heard and said “at least my mom hasn’t fucked all my friends.” Everything came out, sons got enraged, damaged mine and another person’s car, totaling the other persons car, my car just got a dent. No cameras and no witnesses made both of us pay money for it.

22.

“I had sex with my friends mother, I was underage at the time and she was arrested after people found out. In court the charges were dropped and they moved away. But seeing my best friend having to get up in court and talk about how his mother isn’t a sexual offender with me in the room has gotta be the second most awkward moment of my life.”

23. I’ll go plug his mom again

“Not quite the same light, since we’re not “best friends” but I maintained a friendship with my exs son outside of our relationship. She’s now 36, he’s 19, and I’m 28. When he gets moody I tell him to quit his shit or I’ll go plug his mom again.”

24. The Worst

“My mom took my best friends virginity. That was the fucking worst when I found out.”

25. There was this famous mom

“There was this famous mom in my hometown back when I was in highschool, who had a big black hummer with a liscense plate that said “Humdinger” (don’t know if it was spelled that way). People called her hummer mom. She was always driving around a bunch of kids. Her daughter was dating this one kid for a few years. He would always complain about his girlfriend, claiming that the only reason he dated her was because he was banging her mom. No one believed him (he started making these claims in 8th grade, and they carried through his freshman year of highschool), everyone just said he was a typical kid just full of shit. Turns out, he wasn’t lying. His mom found a nude photo of this woman in his phone somehow and the whole story came out. The lady was then arrested for statutory rape and her family subsequently moved out of our town in embarrassment.”

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