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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.
Spent the night at a friend’s house. I was told I could sleep in his mom’s bed because she was going to be out most of the night and would crash on the couch. I went to bed at 2ish. She came home, showered and went bed at like 3ish. I woke up to random cuddles when she climbed in bed and a “It’s fine just go back to sleep”. Nothing really happened but she made pancakes in the morning and we never spoke of it.
I don’t think my friend was aware of it except to deliver the message that “Mom thinks your a good friend and can stay again whenever.”
Unfortunately we went to different schools next year so that never happened again.
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.
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.
Ya. 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 thanks 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.
I slept with my buddy’s mom after seeing her at the club downtown. I kept it a secret for years until he poisoned me. I ended up getting him back by having a cookie made to break the news that I had sex with her.
Also, the chocolate on the cake was a laxative.
I slept with my life long friend’s mom when I was younger and it was pretty amazing. Here’s how it went down:
She asked me to fix her computer as it was being slow. A common occurrence among my friends and family as I was pretty computer savvy back when I was younger. Opened up Internet Explorer and she had about 11 toolbars and instantly I knew what the problem was. I made a joke about visiting shady porn sites and she just let out a nervous chuckle and we went about the task.
Somewhere along the line I downloaded something to clean the malware and was trying to find her download folder so I opened up a few folders and there it was. Large thumbnails of her nude. At this point she’s in the kitchen with said friend making us snacks of some sort.
I get curiously aroused and open up a couple and bask in their glory. Suddenly I can feel something strange and glance behind me and there she was. Like a ninja. Didn’t hear her coming at all. I’m so beat red and to embarrassed to even say anything now. Felt like she was there just smiling nervously for hours but it was probably a few seconds. She took a peek into the kitchen from her bedroom door and came back over. Took the mouse and closed the open picture, bent down and whispered “There’s some better ones in this folder,” and walked out.
I’m just sitting there so nervous I’m shaking and sweating at this point so I just close everything. Run the program. Remove the malware and tool bars and walk out of the room. Without making eye contact with either of them I tell her the job is done and she excitedly thanks me about 30 times and my buddy and I head downstairs to covertly smoke some weed. The entire remainder of the night felt awkward as all hell and I think I said about 9 words to him the whole time. So it’s late and we crash out.
Next morning we sleep to about noon as stoners usually do on a lazy weekend. We smoke another joint and head upstairs to eat something. His mom was bugging us about the smell of the basement and making jokes about how we’re probably going to end up sitting around watching stupid cartoons all day now like usual. Then the phone rings. She talks for a bit in German and comes back over and says my buddy has to go help his elderly grandma do something at her old people home so she’ll drive him there and drop me off at home afterwards.
We get in the car. She drives him there and he gets out. Then she starts heading towards my place and looks back with a smile and turns on to a road going the other direction. Drives us back to my buddy’s place and tells me to follow her for a nice chat. I figured I was going to get the third degree about snooping into her pictures. We get inside and she almost immediately drops her shirt and asks me if it’s better in real life. I’m just completely stunned and trying to make words come out of my mouth but it was probably just gibberish. She then takes my hand brings me to her room and tells me, “not a goddamn word to ( friends name ) ok ? I just nodded and she began to strip down and kiss me and tell me how she thought about a younger guy and thought about it being me the previous night and it turned her on.
We had the most glorious sex. Well for me anyway. Pretty sure I came about 11 times. She was older and had an aged face but that body was amazing. Her vag was tighter than I’ve ever felt too. We finish up. She drives me home and we never mentioned a word about it for probably like 6 or 7 years. There were some awkward days after that, let me tell you. Never mentioned a word of it to my friend either. He’s still my best friend. Known him 27 of my 28 years on this planet.
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.
I got a BJ from my then-girlfriend’s mom when I was 17 or 18. I would mow their lawn sometimes, and was over there doing that one day while my GF was at work. When I was done, I went in for a drink.
I’m chitchatting with my GF’s divorced, 40-something mom, totally innocent, and out of nowhere, she says, “So, how’d you like it if I sucked your cock?” I was shocked, and just kind of mumbled out, “Uh, well, um… OK”, and she went to town.
She wasn’t exactly a MILF, but she gave great head. I was just kind of going back and forth in my mind between “Holy shit, this is amazing” and “What
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