MILF. We all know what it stands for (if you don’t…how embarrassing…Google it…I’ll wait). These AskReddit users are brave souls who came face to face with a cougar and lived to tell the tale.
1. Limo for the Win
“I didn’t sleep with her but did fool around with a buddies mom. We were in college and he was one of the last of us to turn 21. His mom was a very cute (not porn milfy but just a very attractive woman) in her mid 40s who had been divorced about three years at that point.
She and a few of her friends came out with us for his bday. We got a limo for the night provided by her and went bar hopping. He got obliterated of course and had to be sent home by cab with two of our buddies around midnight.
The rest of us got pretty drunk and at the end of the night we took the limo and went around dropping people off. I lived farthest from the bar area so was dropped off last, besides friends mom who rented the limo.
We had been a bit touchy feely even before we were alone but she turned it up a lot. We opened some champagne and did a toast and she sat next to me and kind of threw her leg over me.
We flirted for a bit then bam, we kissed. We made out for a bit and she straddled me. She got topless and I played with her boobs for a while. I tried to finger her but the angle was awkward so we kinda laid down.
I fingered her for a couple min but before she got off she got up and pushed me back. She gave me head, which was awesome although I was super hammered and everything is a bit blurry. Before we could go further we got to my house.
She freaked the fuck out the next day and called and made me promise to never tell her son and said it was fun but could never happen again.”
2. Maybe Ask BEFORE Sex…
“I slept with my mom’s military friend. I was only 16 and she thought I was in my 20s even though I looked 10… I know she wasn’t lying cause she cried when I told her my age.”
3. Welp, You Ruined That Kid’s Future
“I slept with the mother of a high school kid I coached. I was only 21 at the time, he was 18. We had gone to the same high school and I was mentoring him, as well as recruiting him to play at the same college as me once he graduated. I would consider him a friend because I saw a lot of myself in him, and he was mature for his age. He invited me over for a bbq,I stayed for awhile talking to his mother to discuss university plans. Eventually, the son decided to go to sleep early, he said he was tired from two a day practices. I stayed to talk to his mother, she was very thankful for all I had done and was filling my stomach with food and drinks.
We both got drunk, one thing led to another and she took me up to her bedroom. About 5 minutes into it, I caught a glimpse of a picture hanging above the bed, which was of her son. I started to feel guilty and couldn’t stop looking at the picture, weird, I know. As I lost focus from having sex, distracted, I ended up smashing my skull into the headboard of the bed. It hurt, a lot. I stopped for a moment to realize that I was bleeding all over the place, in a panic, I yelled and asked her where the washroom was. I ran outside to the hallway naked, I guess the son had heard all the commotion and came outside. We ran into each other right outside the bedroom, locked eyes, sighed and went back into his room. He stopped talking to me at practices and eventually decommited from my university. I still feel bad to this day.”
“A mom of a girl from a group of friends. We were in our late twenties. One night I wasn’t digging the club, just not feeling it. Went outside to try to get some air hoping I’d feel like going back inside. Struck up a convo with a lady there who was also not feeling it. Decided to hit up Denny’s. Then my house. Then I was in bed with a 40 plus lady and it was great. Next morning she thx me for a great night and makes it clear it was a one nighter and leaves.
Fast forward to a big summer party at the house of the girl I mentioned earlier. Halfway through the night her mom comes home with a few friends to party with us. Ya it’s her. She’s a tiny bit surprised to see me but says nothing, at first. A few drinks later and she’s a mess. Pulls aside her daughter to ‘confess’. Daughter hates her newly divorced moms habits and loses it. She comes at me fists flying, I take a couple weak shots to the face before another girl grabs her and they start a screaming match, about me, and her mom, fucking. Like I purposely fucked her mom to embarrass her. Then she remembers that her and I made out once a year or so prior and now it’s ‘ I turned you down so you went after my mom’. Messy night. I left with friends and they all thought it was too funny. I walked away with a great story.
The girl and her mom had a falling out triggered by that night and the daughter moved to Toronto shortly after that with her dad. The mom, now with nothing holding her back, became a cougar on the prowl for a few years and eventually settled down with a cool dude about 15 yrs younger than her. I still bump into her once in a while and she’s settled into old age rather well. The daughter and I now message each other once in a while. She’s sorry she hit me. I’m not sorry about any of it. Although my friends bring it up a little too often 🙂 I don’t mind because it’s funny.”
5. Some People Like to Watch
“I slept with my friends mom while her boyfriend watched. It actually took around 5 years for it to happen but there were a good number of blowjobs in between. I admitted to her one day that I found her very attractive and she said the same to me. Fast forward a year and I’m over at her place helping her take down Christmas decorations. We get pretty close, I start rubbing her leg while she’s bent over the couch, she starts moaning and we take it to the bedroom. She said it’s been a while and I made her cum just by going down on her, she then gave me a solid blowjob and once it was all done we were both actually in shock and agreed to never say anything.
I should note she lived fairly close, her son moved out of state and her ex-husband was gone too so I’d stop by once in a while just to catch up. Eventually these stops led to her giving me blowjobs which she said she enjoyed doing and it definitely wasn’t a problem for me. She stared dating this guy who actually got off on the idea of her hooking up with me so we’d fool around and send him pics of what we were doing. He lived a few hours away so he wasn’t around much but he loved the idea of me and her. One day I go over and she tells me he’s coming into town so we all go have dinner together. We went back to her house and she started giving me as blowjob while he was there chilling on the couch in front of us. Had mind blowing sex with her that night which was almost a year ago. I’ve been back to her place numerous times but just to catch up and we’re both comfortable just keeping it friendly for now.”
“I slept with my friend’s Dad, but I didn’t actually know he was her Dad. I did my undergrad degree at a very small, prestigious and close knit, University; it only had 300 new incoming students per year.
It was strange compared to other Universities I’ve attended since my undergrad, the professors and tutors were very active in student life and would often come to the student society events and they would even come to the union and get hammered with the rest of us.
I ended up getting to know a professor through a life drawing class that I would run weekly. He would come and write poetry about the person, instead of drawing, which really impressed 20 year old me.
One drunken night at the Union we ended up going home together and hooking up, after the first time it happened a few more times, usually when we’d been drinking but a few times after life drawing.
I didn’t really want to tell anyone what was going on, because I thought he was about 15 years older than me and to be honest it’s pretty embarrassing to be screwing a professor. Eventually I did confide in one of my very close friends about what was going on; and when I did, a look of absolute horror spread across her face.
Turns out he was actually more like 30 years older than me, and his Youngest (!!) daughter was actually a friend of mine. She didn’t want people to know her father was a professor at our Uni, so she kept it secret!
Yeah, I stopped sleeping with him after that; though we did remain friendly it was still way to weird.”
7. Regretting It
“I’ve been sleeping with my mom’s old work friend.
I’m 25 male. She is 40 We have been fucking here and there for over a year. We just text each other when we wanna meet up. Do our business. And leave.
It all started when she came into my work and said she moved back to town that week after her divorce was finalised.
We went out later that week and had sex at her mom’s place. (It was where she was staying and her parents were staying at their summer home in arizona)
Since then we have done it in a hotel. My car. My house. Her house. Her car. It’s been nuts.
I always regret it soon after. Maybe because she isn’t as hot as she was when I was 15 and met her. Talking with her is just boring too. I definitely don’t want to date her or anything.
Also she is OK in bed. Not amazing. And not shitty.”
8. Happy Ending
“My parents were in a car crash when I was 19 they were in the hospital for months with several injuries. My mom’s best friend had me (only child) stay with her. I could’ve stayed at home but it just felt empty. She was in her late 30s early 40s and very cute how she was single (at the time today she is married) one evening we started talking about sex at the time I’d only had one sexual encounter, never given or received oral and made her aware of that. She walked over to me told me never to tell my mom what she was about to do pulled out my cock and blew me on the spot. The rest of the time I stayed I slept in her room and we regularly had sex. When Dad got out of the hospital (about a month earlier than mom) I went home but damn even 13 years later I’ve never had sex that came close to our sessions she was so knowledgeable and every girl since has had it better because of her teaching.”
9. “She Was 50 After All”
“I slept with my best friends mom. I was 21, she was 50. We were all staying the night at a friends house. He was in our friends room trying to score with her and me and his mom were out on the futon. Kinda went like the porn goes. I was on my back and she was on her side. Then her hand landed on my chest and eventually it was down my shorts. It all progressed they way it normally does (except I was already terrified so reciprocating oral to a 50 year old woman was beyond my narrow comfort zone) and eventually I was rocking on top of her with my hand over her mouth trying to keep her quiet. Her sons room was about 20 feet away and the door was cracked so I was on prett high alert. I blew it in her, she was 50 after all. Then we went to sleep. We talked about it here and there. We immediately decided we wouldn’t tell her son although I’m pretty confident he wouldn’t have cared. We are all still in contact today.”