Talk about awkward! When it comes to bro code, a friend’s mother should be off-limits, but not for everyone! In the heat of the moment, these guys just couldn’t say, ‘no.’ Here, they share how one thing led to another before they got intimate with their friend’s mother.
All stories have been edited for clarity.
The Mom Of My Enemy Is My “Friend”
“In high school, I knew this girl, Amanda. She was a brat who hated me and treated me like trash. Fast forward to two years after graduation. I get a job at a large electronics retailer selling TVs. Well, lo and behold Amanda’s mom started working in home appliances. Now, I need to mention that Amanda’s mom is gorgeous. She has a great olive complexion, a very athletic body, and great legs.
Well, she gets her looks from her mom. Her mom knows me from school and I’ve always been a hit with adults as a kid. I ended up working with Amanda’s mom, Paula, quite often. I never hit on her, I knew she was married. By this time I had a primary job as a bank teller on the weekdays and worked at the store on the weekends. One night, July 4th weekend, a bunch of employees were hanging out in the parking lot, just shooting the bull, when one guy mentions how long It’s been since he was on a date. That’s when Paula mentions, ‘I’ve been divorced for two years and have yet to be asked on a date.’ I was astonished, but, being the funny guy, I said, ‘Well I’m off Monday for the holiday, I could take you out.’ She smiled and said, ‘Sure, here’s my number.’ I was super excited, here I am, going on a date with that brat, Amanda’s mom. She’s gonna be so ticked off!
Cue evil laughter.
Well, Monday comes around, and I got all nice and dressed up. Paula and I meet up, and we go out to dinner. It went quite well. After dinner, I was thinking of a way to prolong this wonderfully devious, and surprisingly enjoyable, night. That’s when she suggested a movie. Of course! Well, we get seated in an almost empty theater to watch ‘Iron Man 2.’ Her choice. I sat down, and she grabs the armrest between us and pushes it up, and snuggled all nice and tight against me.
The movie ends, and nothing happened, so we get into my car and I begin to drive her back. Then I get a crazy idea. It was nearly midnight, and I had to work at 7 am, but I drove to the edge of town and parked my car off the side of a highway. We sit there for two hours talking. I took her back to her car, and, as we said our goodbyes, I got a feeling that she wanted to kiss me. But, in my head, I thought, ‘No way dude. Besides, she’s twice your age, she just wanted a good night out.’ So we went our separate ways.
The next day, I couldn’t text her because I’m busy, and she was at work all day. I got home at about 4:45. About 30 minutes later, she texted me and said she was outside and wanted to see me. I went outside and got into her car, thinking we are going to dinner, or she is going to call it off. Instead, she turned to me and said, ‘Hey, how was your da- no, no, this first.’ She grabs my head and pulled me in for a kiss. It was amazing. We sat there and talked for another few hours, then she had to get home.
That was when our amazing, but brief, relationship started. We would text and talk all day and night. I found out she was living with her Vietnam vet dad who needed her to take care of him (PTSD). He was verbally abusive and very loud. For the first month, I felt like it was a high school relationship. So much drama, but we got along great.
After about a month together she asked if she could spend the night that Friday. I was super excited. Now, not only was I going to get laid, but Amanda still didn’t have a clue. Friday came along, and Paula came over and started drinking. We do the horizontal tango and it was… is there a stronger word for amazing? She wasn’t my first but oh boy she was better. She wore me out.
At 8 am the next day her dad called, freaking out that she wasn’t there. So Paula bolted. We hooked up again about three weeks later and I didn’t know it could get better. Three weeks after that, she came over and we started cuddling, watching a movie, and her phone rang. It was Amanda.
Paula answered, ‘Hey baby, what’s up?’
I was four feet away and heard from the phone ‘ARE YOU SLEEPING WITH KEVIN FROM WORK?’
‘What?’ Paula asked.
I watched Paula deflate and droop her shoulders.
‘Yes, yes I am.’
Then I heard more screaming, going on about how it’s disgusting, he’s half her age. Paula interrupted her and said, ‘But he’s so good! It’s awesome!’ Amanda blew a gasket. Paula left while getting yelled at. It was a complete role reversal. Amanda was acting like the mom and Paula the daughter. I was both sad and blissful. Sad because I knew it was over, but blissful because Amanda found out. We stopped talking, she became a school teacher again.
I learned Amanda discovered our relationship via our sisters having choir together. My tactless sister said, ‘My brother is dating Amanda’s mom!’ to Amanda’s sister, Kim, Kim told Amanda. Boom! Headshot!
Looking back on it now, I’m glad it ended when it did. Paula had severe depression about her divorce, was in a lousy living situation, was a heavy drinker, and really wanted a kid. A year after that fateful phone call I found out she got pregnant by a different guy, and she just recently had that baby. Another girl, number four for her. She moved out of her dad’s and filed a restraining order because he actually tried forcing himself on her. She now lives with her ex-in-laws… Man, I don’t miss the drama, but I do miss the nights we had together.”
A Different And Unexpected Form Of Payment
“I have a friend whose mom was always really nice and bubbly. We’ll call her Jane. I’ve known Jane since I was 13. I was friends with her son in junior high but that’s about it. We’ll call him Sam. Well as Sam and I grew apart, my mom remained very good friends with Jane. So I would see her quite often.
Jane had a few boyfriends through the span that I’ve known her, but never for more than a few months, and never any plans for engagement or anything. So as I grew older, Jane became nicer and more touchy-feely. I, however, always wrote this off as my imagination. On top of this, Jane would often comment about how I was growing to be such a tall, handsome young man and would compliment my muscles or let me know she liked my new haircut. Basically, I noticed Jane was paying a lot more attention to me than seemed normal. When I was 19, almost 20, I was working a job that didn’t have many hours to offer. Jane, being a single lady whose only son (Sam) left for college, insisted that I could do yard work and such around her house and she would pay me for it. I wasn’t opposed to this, seeing as I needed money.
Well, one day Jane needed her carpet pulled up because she was getting wood floors. So who better to do the job than yours truly? I remember the couch was pushed onto the tile right next to the kitchen and after about thirty minutes of straight work I was tired and decided to sit down and rest. Jane had come home from work about thirty minutes earlier and taken a shower and came out wearing just shorts and a sports bra. Now keep in mind, Jane is an attractive, dark-skinned, early middle-aged woman who is in good shape. I’ve always thought Jane to be attractive in a very traditional sense. So she comes out and says that she would help me get the job done. She went on to joke about how hot I looked as a blue-collar man and how she loved a man who was capable of hard work and wasn’t afraid to work up a sweat. She joked like this for just a minute, then playfully sat on my lap while I was on the couch. This wasn’t completely shocking to me, as I’ve known her for a while and she was always a flirtatious woman.
While she was on my lap I couldn’t help but quickly look at her cleavage that was pressed against me. She noticed this and giggled and playfully scolded me, but went on to say she didn’t mind. This is where things got real. She then straddled me and said ‘I’m used to the attention.’ This caught me off guard and I said no. Even though I really wanted to. She wouldn’t take no for an answer. So I did it. I lightly touched her chest with one hand. Then pulled back. She then said ‘Oh, come on really FEEL them!’ Jane took both my hands and pressed them against her chest. I was staring at her chest. But I could feel her staring at me. While she did that she began to stir her hips and I could hear her breathing pick up a little. I won’t go into any more detail, but this quickly turned into me having shacking with Jane.
I continued for a while to go to Jane’s house to do work. And we hooked up a few more times after that. We never discussed it but it was obvious we wouldn’t tell anyone of this, especially Sam or my mom. After a while, I got a better job and Jane became involved with another man. It was as if nothing ever happened. Which I honestly prefer. I still see her fairly often, but she’s a very cool person and nothing ever seems awkward or anything of that sort. Overall, it was an awesome experience.”
“I Enjoyed Our Time Together”
“We weren’t best friends, but a friend of mine helped me get a job in college at a fast food restaurant where his mom worked. She was a nice lady nearly twice my age, I was in my early twenties, and she was in her late thirties.
She and I got along well, but she was always playfully flirty. I didn’t really think anything of it, but a few months into the job she started borrowing money from me to get weed on the side (she was single, lived with a female roommate, kids had moved out, and she was heavily addicted to weed – like has to smoke several times a day or else she has panic attacks). I didn’t mind because she always paid me back.
She texted me one day saying she needed to borrow money for weed really bad and offered that if I bought it she would share it with me. I had only used it once before or so, but it was at the start of a weekend and I had nothing planned and was bored, so I figured why not, especially if it is with one person I know in a place I am familiar with.
She came over and we shared a joint and talked, and about halfway through she started to get flirty and joked that if she kept borrowing money from me she might have to think of other ways to pay me back. I knew what was happening and didn’t really object, she was a decently attractive woman, in decent shape, and we were both single. So I replied that I wouldn’t mind that at all, and she played coy saying things like how long it has been for her and that she doesn’t even know what it feels like anymore, and I just said that if we went upstairs she would rediscover what it felt like; then we went upstairs.
She was very vanilla in bed, most of the excitement came from her being an older woman and my friend’s mom… For the next few months, we were friends with benefits, she’d come over after work every other night. She eventually lost her job though because she demanded a raise and didn’t get it, so she went off on our boss and the boss reacted by firing her. Things weren’t serious between us and I didn’t really want a relationship, so she ended up contacting an ex-boyfriend who lived in another state, and he paid to move her in with him.
Her son never found out; I see him every month or so. I was kind of glad to be rid of the arrangement in the end, but I enjoyed our time together.”
A Pool Party He’ll Never Forget
“When I was 18, I hung around this cute girl that was new at school for our last year. I would give her rides to and from school because she knew me from a mutual friend before she transferred to my school. I always had a crush on her, but she was pretty far out of my league. It was a friend zone kind of thing, but I didn’t really care.
Anyway, we were pretty inseparable for a period of time. I would hang out on her front porch and her mom would always come out and talk with us. She was really, really attractive. Long blonde hair, slender, and had that attractive raspy voice. I would always joke with her mom in the room about her mom being hot, and since she was recently divorced, I think she liked the self-esteem boost.
Probably a year after we had stopped hanging out so frequently, I asked the girl if she wanted to go to my friend’s party that he was having in the middle of a cornfield. She agreed to go with me, and we got a chance to catch up on the way over. I must have been abnormally funny or charming that night because she was laughing at every dumb joke and really flirting with me the whole way over. While we were on a dark country road she leaned over and kissed me while simultaneously rubbing her hand on my crotch. It caught me off guard as I didn’t know she was even into me like that. I pulled over off the side of the road, shut my car off and we hooked up for a bit. She told me that she wanted to hold off on going further, but we still made out and groped each other throughout the rest of the night. Nothing ever really came of it after that, but we still remained good friends.
Fast forward another year and my buddy and I end up at her mom’s house because he now had a fling with this girl. She had a couple of friends over (guys and girls), but then later on in the night her mom was dropped off at the bar. This was the first time I had seen her mom since I used to come over back in school and she immediately remembered me and was more than happy to see me. We all swam in their pool, drank, and drank some more. Her mom jokingly kissed me on a dare in front of her and the girl freaked out and pulled her off of me. So after that, her mom kept her distance from me for the rest of the night because I think she may have known that she was crossing a line with her daughter. Later on, everyone passed out and my friend went to bed with this girl. I went out on the deck to smoke before passing out, and about two minutes later her mom followed me out. Without saying a word to me, she straddled my thigh. She was wearing a sundress and I could feel that she wasn’t wearing any underwear as she straddled my leg. Let’s say she was ready to go. She pushed my head into her chest and began grinding my thigh. Basically after that, I did her mom from behind over the balcony and again in her bed. Her daughter doesn’t know about it at all to my knowledge unless my friend told her. Didn’t happen again after that, but I never really found myself in that position again either.”
Well That Was Unexpected
“When I was 18 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. I agreed, so I got in the driver seat of the suburban and started heading to her mother’s. 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 hand up to my belt and starts unbuckling it and unbuttoning my pants. The next thing I know, she was out of her seat and on her knees on the floorboard.
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 was pretty freaked out. I was only 18 and this was a lot to take in. Anyways, she went back for some more, this time taking my pants off as she goes. After a few minutes, she took off her pants and crawled up to where she was straddling me. As I laid there I was flooded with the emotions of excitement, horror, guilt, and pleasure. I protested briefly but by the time I had a chance to put a sentence together, she had already started. We finished up (admittedly not too long after it began), fed the dogs, and went back to her house where I smoked a bowl with her daughter. We didn’t talk about it for about a week, but it turned into a semi-regular thing for about a year and a half. Eventually, I cut it off because I found a girl that I cared for, and she lost her mind on me.
We haven’t really talked since.”