Often boys get crushes on other peoples' moms. Though innocent enough, it's something that doesn't usually go further than a teen fantasy or high school...unless they're one of the thirsty people in these stories. To quote the one-hit wonder from Fountain of Wayne, these guys are quite literally in love with Stacey's mom.
"I hooked up with my little brother's babysitter/my friend's mom when I was a teenager. She was 35 and had short dirty blonde hair and was in great shape. At some point, his mom started offering to massage my back while I played. I let her do it and thought nothing of it. One day, she started reaching around a bit and next thing you know I was getting turned on. 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 five minutes it was on. The oddest phrases came out of that lady. 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 logic test, so we kept going.
Well, for the next five days we did it at her house, mine, in the car, and really anywhere we could get the chance to. She even had it set up where she could sign me out of school (she was that tight with my mom), so she did one day, and we had more or less an all day romp.
She offered me a few hundred dollars and said it was so we could take a vacation to get away from everything. I took it. I also told my older brother since I couldn't contain myself any longer. He immediately told my mom that she had threatened to kidnap me (I guess that is what it technically would have been) and my mom told my dad and my dad called the cops.
She was arrested and forced to perform a few hundred hours of community service and ordered to pay for me to see a psychiatric counselor for a year. My friends all found out (she told them) and it caused a large faction of people at my school to be angry with me (no idea why). I never went to see a shrink and when I turned 18 my mom gave me that money to buy a car. I got a 1981 Mazda RX-7 (this was in 1991)."
"My girlfriend's mom is an OB/GYN, and she told us a story about a mother that set her teenage daughter up with another teenage boy she met someway or another. The mom makes some arrangements between the two, and the boy shows up one night to pick her up on the motorcycle. The mom, somewhat understandably, says that she wants to know the boy is a safe driver and asks the boy to give her a ride real quick. The mom hops on the back of the motorcycle, and the boy rides around the neighborhood. The mom objects, and says she wants to know how he drives on the highway.
Long story short, they drive off to the beach leaving the daughter behind at home, hook up, the mom gets pregnant, and roughly nine months later, my girlfriend's mom delivers a baby conceived under the most ridiculous circumstances she's heard of in a long, long time."
"My ex and I broke up a while ago, and we moved on. I started to identify as poly and met this really hot businesswoman at a food market, and we chatted it up and became friends. She was older than me, which I never minded since I loved older women. We became hook-up buddies, and she was warming up to me having other girlfriends, and we soon fell in love.
We started our relationship and things were amazing, everything just felt right. She was monogamous with me as that is just who she is, and I was poly with her. She also works crazy hours and has a very busy life, but she loves it and that's what counts.
So months pass, and she invites me to meet her family at a family gathering. I'm excited to meet her family, not so excited to learn her ex is gonna be there though, a little nervous about that. We walk through the door, and she introduces me to her daughter, who happens to be my ex! Her eyes get wide and my ex runs upstairs crying.
My girlfriend and my ex (her daughter) start yelling at each other upstairs, My girlfriend's ex-husband is giving me death glares for getting with his wife and daughter, and I stand there awkwardly for five minutes listening to my ex tell her mother it's not okay to bang her ex-boyfriends. The party ended up being pretty good, but my ex was still pretty ticked at me, and the ex-husband and I avoided each other the whole time.
She has an awesome family, and we are still happily together."
"I was having a chill night at home with my girlfriend, my friend, and my mom. We just finished having supper and we started drinking. At one point, my mother, my friend and I were getting fairly tipsy. We started arguing about politics, and since my mom and friend have similar views, they kind of ganged up on me. 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. Now this may seem like a bad idea, but my mother has always been very cool with my friends. So the fact that he would attempt something never occurred to me.
Fast forward a few hours later, in the middle of the night. My girlfriend wakes me up and tells me we have to leave. I'm still half sleep and I just agree. As I am starting to come to, I realize something is off. My friend comes downstairs and passes out on the couch, I go upstairs and my mother locked herself in the bathroom. I'm just really confused but I don't think much of it. My girlfriend and I decide to go get some McDonald's. When we finally get on the highway, my girlfriend 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. I start to get furious, but it still seems unimaginable that they would do that. So after I promise my girl that I will not attack the guy, we decide to go back home. At this point, I have no idea if it's true or not, for all I know my girlfriend was probably dreaming. I get home and tell the guy to call himself a cab. Mother is still locked in the bathroom. The cab comes and the guy goes home. I end up going to sleep at my girlfriend's house.
Fast forward one month. I haven't talked to the guy since. My mother denied everything, said that the friend tried to initiate something and there was kissing involved but nothing serious. At that point, I say oh well, nothing I can do. Then, out of nowhere, someone I know sends me a message asking me if I knew about my friend that was in the hospital a few weeks ago. I get pretty confused and that's when I realized that the guy tried to commit suicide that night. I am incredibly shocked to hear all this, I decided to contact the guy and finally get the record straight on the situation. He tells me that he did in fact sleep with my mother, that he regrets more than anything else, and that he is sorry. I tell the guy that I don't hate him for doing that, after all drinking was involved. I just told him that I was disappointed he did that to my family, I asked him to not contact me for a while because I don't want to talk to him and that's it.
I also confronted my mother about the ordeal, she still denies it to this day, who wouldn't right? She is still with my father, who doesn't know what happened. I told my mother I would not be the one to tell him, and that it was her responsibility to do it.
Since that day, I've had a few nights of drinking with my dad and knowing the truth is tearing me apart."
"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 starts working in home appliances. Now, I need to mention that Amanda is gorgeous. She has a great olive complexion, 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, I get all nice and dressed up. Paula and I meet up, and we go out to dinner. It goes quite well. After dinner, I'm thinking of a way to prolong this wonderfully devious, and surprisingly enjoyable, night. She suggests a movie. Of course! Well we get seated in an almost empty theater to watch 'Iron Man 2.' Her choice. I sit down, and she grabs the arm rest between us and pushes it up and snuggles all nice and tight against me.
Movie ends, nothing happened, so we get into my car and I begin to drive her back. Then I get a crazy idea. It's near midnight, and I have to work at 7 am, but I drive to the edge of town and park my car off the side of a highway. We sit there for two hours talking. I take her back to her car, and, as we are say goodbyes, I get the feeling she wants to kiss me. But, in my head I'm thinking, 'No way dude. Besides, she's twice your age, she just wanted a good night out.' So we go our separate ways.
The next day, I can't text her because I'm busy, and she's at work all day. I get home at about 4:45. About 30 minutes later, she texts me and says she's outside, she wants to see me. I go outside and get into her car, thinking we are going to dinner, or she is going to call it off. She turns to me says, 'Hey, how was your da- no, no, this first.' She grabs my head and pulls 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 gets here, Paula starts 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 she bolts. We hook up again about three weeks later and I didn't know it could get better. Three weeks after that, she comes over and we are cuddling, watching a movie, and her phone rings. It's Amanda. She answers, 'Hey baby, what's up?'
I'm four feet away and hear from the phone 'ARE YOU SLEEPING WITH KEVIN FROM WORK?'
Paula says, 'What?'
Paula deflates, drooping her shoulders,
'Yes, yes I am.'
Then I hear more screaming, going on about how it's disgusting, he's half her age. Paula interrupts her, 'but he's so good! It's awesome!' Amanda blew a gasket. Paula leaves while getting yelled at. It was a complete role reversal. Amanda acting like the mom and Paula the daughter. I was both sad and blissful. Sad because I knew it was over, 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 tells Amanda. Boom! Head shot!
Looking back on it now, I'm glad it ended when it did. Paula had severe depression about her divorce, bad living situation, heavy drinker, and she really wanted a kid. A year after that fateful phone call I found out she got pregnant from a guy from AA, and she just recently had that baby. Another girl, number four for her. She moved out of her dad's, 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."
"My buddy Jake's parents were divorced, and she was a young mother (about 17 when she had him). The mom, Jane, and I always got along really well and it was honestly like hanging out with a slightly older friend. We would make fun of my buddy about his girlfriends, draw on him when he was passed out etc... I would also talk to her about my issues in a way that I couldn't to my own parents, more about partying and girls. So I would say we were friends. Jake also had a little sister who is the biggest sweetheart I know, but that doesn't really matter.
Jake had a cabin in the mountains, and he and I would go up skiing a whole bunch, so we decided to go up a weekend. And Jane and his sister came up a day later. It was a good ole fashioned fun weekend of skiing and Jake had to get back for work on Monday but Jane and his sister were going to stay and I decided that since I didn't have to work I would stay up and head back with them a day later. Well his sister took off to a friend's house for a party, and I was watching a movie on the couch when Jane sat down with me. We were chatting and joking and just having a good time when I wondered out loud if Jake had left anything to drink. She said she had something better and brought back a nice bottle of something, and we went through that pretty quickly. Now I'm a lightweight, so I was pretty buzzed at this point and I think she was too, but she went and got another bottle anyway. We started to drink and started flirting.
We were talking about my most recent ex when I said, 'Yeah, she was bad at kissing and just about everything else.' That's when she answered 'Am I any better?' Then things got pretty real pretty quick. We were almost bare on the couch before we took it up to the bedroom and I'll leave it up to your imaginations on what happened next.
Next day I woke up, and she was out of bed, and when she came back into the room we talked and agreed it had to stay between us and no one could ever find out. We drove back the next day, and have never spoken about it again."
"I slept with my friend's dad when I was 15. It was probably the only time I don't regret sleeping with a guy. He was really sweet and gentle, and it was just a one time thing.
He was like a second father to me, both of our families were close, his daughter and I were close. We'd have sleepovers all the time growing up. He'd watch movies with us, and build forts. Ideal dad stuff, he was always there for us. Then her mom died, and he sort of fell apart. He was keeping it together for her sake, but he was really on the verge of falling apart.
We were having another sleepover, with some other friends, tried to joke around with him, but he was still sorta down. I'd gotten up in the middle of the night for water, came down to the kitchen & found him just sitting at the table staring off. We chatted for a bit, about stupid stuff like we used to, he started to break down, I hugged him and it just sorta escalated from there. But I was okay with it, and I told him since he was there for me all those years, I'd be there for him, but just for tonight sorta thing. He just repeated thank you, over and over and over... totally quiet voice.
Don't think it messed anything up permanently, none of us bring it up. My friend knew though. Coming out of her dad's room at 6 am to find her waiting is a pretty good giveaway. She was upset at first, but she hugged me (after slapping me). Stuff was shaky for a few weeks, and she'd slap me randomly over the next few months."
"My friend Jane is about four years younger than me. When I was about 19, we actually started to hang out a bit. I was also friends with her mom (who is 10 years older than me) by this time.
I got kicked out of my place for reasons, so her mom let me crash in the living room for a couple weeks. After a few days of her mom 'forgetting' that I was there and walking from the shower to her room wearing nothing, I 'happened' to walk back to ask her something. This was followed by a halfhearted 'Oh, I thought you were dressed by now' followed by a long look at her bare body.
I said I was going to have a smoke, and she came out to the garage with a sundress and no panties or bra. Then she sits on the dryer facing my chair to where I could obviously see the goods. She caught me looking, hopped off the dryer, undid my fly, and we did it on a rickety chair. And then a couple times a day while I lived there.
"My first time was with my friend's 42-year-old mother when I was 15.
After getting into a fight with my mother about something stupid, I decided to run away from home. I went straight to my friend Ronnie's apartment. Ronnie was 19, wore a mohawk haircut, had tattoos, and had just gotten out of jail a month prior for beating some guy. Needless to say, I looked up to him because I thought he was just about the coolest person alive.
He let me spend the night, and that's when I met his mother.
Connie was what you might call a tough broad. She smoked unfiltered cloves, wore a black leather jacket, liked to ride motorcycles, listened to heavy metal, and had a knockout figure. She was basically a goddess in my mind, but it never occurred to me in a million years that I would actually be, you know, sleeping with her in less than 24 hours.
It turned out to be a pretty epic day for a 15-year-old. We went to score some pot, picked up some drinks (Ronnie had a fake ID), and went back to the pool at his apartment where Connie was waiting for us. We smoked, drank, and swam until it got dark, whereupon we went inside. We spent the rest of the night talking about topics that were generally taboo for me: partying, getting laid, and punk rock.
When it came time to go to sleep, I tried sleeping on Ronnie's floor, but he couldn't sleep without the radio on, and it was impossible for me to sleep with all that racket. I'm not sure exactly why I went to Connie's room instead of to the couch, maybe it was simply because she was still awake and I wasn't quite ready for this awesome day to end. Regardless, it proved to be a fateful decision.
She invited me into her bed, and I obliged, which is when I noticed that she was completely undressed. I had never in my life been this close to an actual bare woman before, and I was nervous. I got in the bed fully clothed, which led to a minute of awkward (for me) silence, with her just staring at me with this impish grin on her face. Finally, she burst out laughing, and asked me if I was really going to sleep in my blue jeans. I got my clothes off, and not knowing what else to do, I asked her if she wanted a massage.
Once I got done with the massage, it was my turn, and she flipped me over and pulled off my boxers. We were finally both completely bare. She looked up at me and said, 'When you use this on a girl, she's going to enjoy it. A lot.' I was only just starting to realize what was happening when she got on top and mounted me.
I actually said out loud, 'Oh my God, are we doing it?' She laughed, and this was when I told her that I'd never done it before and this was my first time. Her eyes got wide for a second, and I suppose denial kicked in because from that point forward she refused to believe I've never slept with anyone before.
By the time we finished, the sun was coming up. She went to the kitchen and made me coffee, which only solidified my newfound sense of dawning manhood. As I was getting dressed, Connie told me, 'You make me want to throw rocks at my boyfriend. That was good.' I walked back to my house, met my grandparents at their car as if nothing unusual had happened, and rode with them to church.
I got to our youth group class and there was a girl I was crushing on. She gave me this strange look, which prompted me to take account of myself. I was absolutely reeking of smoke and Connie. I could barely keep my eyes open, but there was a new edge in my voice that hadn't ever been there before. I also noticed something different about her, too: I was no longer attracted to her. What had happened to me was so completely outside the world she inhabited that it was impossible to reconcile the two. Not only could I never tell her what I had just experienced, she likely would have been positively disgusted by the whole episode.
I wound up falling dead asleep in Sunday School, I slept all the way through church, and I asked my grandparents to take me straight home after lunch. I never set foot inside that church ever again."
"My parents raised me with no social skills whatsoever. I knew nothing about dating or making friends. I stumbled through life making cringe worthy social embarrassments one after another. When I was 16, a friend of mine arranged a date for me. I chased the girl off on the third date because I told her 'I love you.' I had no idea how these things worked. I felt terrible because I didn't even understand what I did wrong.
Two weeks later on my 17th birthday, I was depressed since 'the girl I loved' left me. I refused to have a birthday party because I was so depressed. I decided I wasn't a kid anymore and I 'ran away' to my only friend's house. He wasn't home, but his mom answered the door. I apologized for bothering her. I was about to leave when the phone rang. She waved me in and pointed to the couch. It was my mom looking for me, she told her I was there, and then she told her 'He's playing with Sam on the trampoline.' She said a few other things and hung up.
I guess she could tell I was upset... wait why did an adult just lie to my mom?
She sat me down on the couch, and we started talking. No one had ever spoken to me like an adult before about my problems. I still held back because I was used to not talking about my life out of fear of my dad hitting me. For some reason I felt like I could trust her and I burst out in tears. I told her everything; how lonely I was, how I lived locked up, how embarrassing it was to be graduating next year yet still living like a little kid. I told her about my 'girlfriend' and I went hysterical. She calmed me quite a bit and told me the generic 'plenty of fish in the sea' bit. It was cheesy but I felt like the world was lifted off my shoulders to speak to someone about this. When I was breathing normally again, she went to get me another glass of water.
Then I panicked, she's going to tell my parents. I felt so dumb, I started feeling the cold sweats and that nervous feeling coming up. I thought for sure I was going to puke. Yep, here it comes. I got up from the couch, turned around and I couldn't believe what I was seeing. There was Sam's mom, wearing nothing but a white button up shirt.
I had never seen an unclothed woman in real life before. I had seen a few pictures in magazines here and there, but not much. Here she was, a somewhat chubby, unshaven, woman who gave birth to four kids, one of them my only friend, with no pants! I reacted how you might imagine. I felt my cheeks heat up, I turned around and sat down on the couch. Why did I do that? I shouldn't have gotten up. She probably was in the shower or something. Even worse I was aroused and couldn't control it. I put my hands in my lap to cover it but it was not working.
She came behind the couch and started rubbing my shoulders. I sputtered an apology, and she lifted my chin back, so I could see her. Her shirt was now unbuttoned and her chest sat basically on my forehead. She kissed me upside down, and I was pretty sure I was going to lose it right there. She came around put her head below my belt which was all of six seconds... and then moments later being hard still she rode me on the couch and did all the work. I couldn't believe it. I said nothing between her kisses. I don't know how long it lasted. After she finished herself off on me, she got up and cleaned me off with some baby wipes.
She told me that's one thing in life I wouldn't need to worry about anymore. I tried to make a joke about referring to the baby wipes, and she just kind of gave me a grin. She then said 'This is between us, you understand? For your birthday. It's not going to happen again.' I said 'Never?' 'We'll see.' she said.
I walked home, and I don't really know how to describe what was going through my head but it was something along the lines of an elated 'Wow, I love life!'
I wouldn't feel that way for a long, long time.
A few weeks later my parents were pretty upset at me because I was walking around with a smug grin and not a care in the world about what they had to say about me. My one friend knew something was up. I wanted to say something, but I was not about to break the secret between me and his mom. I finally fessed up that I slept with someone, but refused to say with whom. I don't know how it happened, but he figured it out.
He was livid and told everyone he could.
The police interviewed me because I was underage. I denied everything but I am a bad liar. I was scared. Even without any ounce of evidence his father filed for divorce. I got put into in-school suspension for weeks because my friend would try to beat me anytime he saw me. I felt like trash but at the same time I could literally close my eyes and feel Sam's mom riding me. It was a very confusing time to feel so good yet so guilty.
Anyway the charges were dropped although my parents pressed hard for something to stick. My parents sued her in some other way. Sam and his family moved away from town and I never saw them again. I felt so ashamed.
15 plus years later I've become much more socially adjusted, but I still hate myself for getting into that situation even though I have the great feelings about it."