MILFs Shared Stories Of The Saddest And Most LOL Advances From Younger Men


Long before Stiffler’s mom seduced Paul Finch in American Pie and the phrase ‘MILF’ entered the cultural lexicon forever, there was Dustin Hoffman and Mrs. Robinson. Just a year or two thousand before that there was Oedipus, the mythical Greek king of Thebes. Young dudes have been trying to sow their wild oats with MILFs since the dawn of time. I can’t say that I’ve ever taken my shot with a woman twice my age, it’s not my style, but my bros have and I’ve witnessed it work and seen them go down in a blaze of failure.

Below, a bunch of self-proclaimed MILFs shared stories of the most desperate, hilarious, and sad advances they’ve received from younger men. Bros, if you’re trying to score with a MILF you’d be wise to avoid these tactics:

_Colombiana_ :
I don’t consider myself to be a MILF, but I have had my sons’ friends try and make moves on me before. I am younger (had my first kid in my early twenties) and am “exotic” (Colombian immigrant in a small southern town). I think those play more of a role than my actual looks. Just something different than what the teen boys here are used to.
The weirdest one was when my boys had a couple of friends over to watch a movie a couple of years ago. I believe they were 14 and 12 at the time. I was watching the movie with them and one of the boys (14 years old) put his arm around me. I didn’t want to make a big deal about it and embarrass him or anything, so I tried to subtly get out of the situation. I yawned and I told the group that I was going up to bed and he stood up and started following me. I asked what he was doing and he said he thought I wanted him to come up to bed with me. I explained that I was sorry for the confusion, but that I absolutely did not want him to come up to bed with me. He apologized and returned back to the media room to watch the movie with the rest of the boys.
My oldest is a senior in high school now and has been asked by his friends if they can take me to prom if they can’t find another date.

I have two teenage daughters and have had several of their guy friends hit on me. We moved to a new town a few years ago and both my girls are quite pretty so they had a lot of new guy friends that would come over and hang out. I would talk with them in the group and kinda hang around and listen to what was going on. Some of the ones who looked older would say things just to see if they could get away with it. I can’t recall most of the things that were said but two stand out to me.
The first one happened when my daughter came in with a group of friends and asked me to give several a ride home. I told her I just needed to hurry and change out of my gym clothes and I’d be right down. Next thing I know there’s a knock at my bedroom door and I ask who it is (my daughter wouldn’t knock) From the other side of the door I hear a boy ask if I needed any help changing. I told him to get his ass out of my house.
The second one happened at a party we my other daughter threw at our house. One of the boys came up and put his arm around me and asked to see my tits. I was so shocked I couldn’t think of anything to say other than fuck off. Then I told him to leave. The next day he called my daughter and asked her to ask me if he would ever have a chance. Seriously?!?! It finally got to the point that she asked me not to come around when her guy friends were over and not to talk to them when I see them at the school because she was sick of hearing things about me from the guys. I had to start just being a bitch after that because obviously me being nice was taken as something other than what I’d intended and I didn’t want to embarrass my daughters any more.

I wouldn’t say I’m a MILF, but 2 of my daughter’s friends have hit on me and her boyfriend of 3 years tried to kiss me.
The most desperate was the boyfriend. We had gone on vacation for my daughter’s 21st birthday to a small town with hot springs. While my daughter, her boyfriend and her friends camped nearby, I chose to stay in a hotel to give the young people their privacy.
We all went together for a soak one evening but my daughter wasn’t feeling well and stayed at the Campground. After the soak, the boyfriend was quite drunk so I gave him a ride back to the campsite. When we arrived, he started professing his undying love for me, said my name 3 times in his most serious attempt at a sexy voice and leaned in for a kiss. He never saw my fist, but felt it land squarely in his sternum. It made for an awkward morning. He confessed to my daughter the next day and she laughed hysterically at his ridiculousness. They broke up not long after.

Every moderately attractive high school teacher has been hit on. Currently, a senior that graduated last year is patiently waiting to turn 21 so he and I can go have a beer. I’m sure in his mind this will lead to a weekend of wild sex where I show him the hidden secrets of the Kama Sutra. I’m just interested to see if anything will have changed by then. Also, one of my son’s friends once told me he’d “like to experience an older woman” and then stared at me.

When I was in my junior year of high school, I decided to spend Christmas Eve with my girlfriend and her family at their grandmothers farmhouse. Their grandmother was a short, frail, bohemian woman who dressed like Steve Jobs and always smelled like dust and Cabernet. Her silver hair was wispy and long and she kind of reminded me of a thin Gandalf. Right off the bat she was flirtatious with, squeezing my arms and talking about how “your last boyfriend was such a stick! Upgrade!” and although it was awkward, I of course didn’t feel physically intimidated.
Until it happened.
After dinner, I decided to help by doing the dishes in the kitchen while others were lounging in the front room. As I’m washing, I feel a pair of hands creep around my stomach from behind. Thinking they were my girlfriends, I laughed and said “hey you”. I was met with the single most guttural “hello” I’d ever heard! I mean it was as though the woman had drowned her vocal chords in zinfandel and camel reds. I looked down and saw the spotted, wrinkly hands and was frozen in shock. Having not said anything, she probably assumed she had the okay, and proceeded to move her hand down to my butt, to which I said “please never do that again” and left the kitchen. I went to the front room and excused my self for the night, and drove home.
I never felt physical intimidation from her, but the whole situation was so off-putting, being that I was 16 years old and she was somewhere around 73. She also gave me intense, lengthy lectures on the proper way to take my then-girlfriends virginity. Not graphic, just weird.

I’m a gilf, and still get hit on by younger men.
But when I was a milf my daughter’s boyfriends would boob watch all day.

When my brother graduated from high school, he had a big party at our house. My mom would walk around periodically to make sure things weren’t getting too ridiculous. At one point, this kid very openly hit on my mom and told her she was hotter than any girl there. Obviously, my mom noped out of that mess and was thoroughly creeped out.

I’m not sure that this qualifies, but… here goes.
When I was 45, I guess I hit my peak. We went to the pool in Vegas. Men kept hitting on me. One time I went to the bathroom, which was about 200 ft away from the pool, behind a row of trimmed hedges. 7 men in their 20’s or so hit on me during the short trip to and from the bathroom.
One young man was pretty insistent. He said that his hotel room was right there on the property. We could be back in 7 minutes – before my husband even noticed that I was gone.
I started laughing so uproariously.
I wasn’t going to go no matter the offer but come on, if you are going to try to seduce me, you could do better than that!
I said no thank you. If I was going to fool around, he would have to do better than that. It would take us 3 minutes to get up to his room. I would certainly hope for more than a minute of pleasure.

My husband is 26 and I am 49. My husband’s friend is also 26 and he used to walk around in his underwear looking at me while he fluffed his package. (he lived with us) Then one night he licked the whole length of a chalupa while staring at me intently. I have never laughed so hard in my life.

I once lost track of time while staring at my friend’s girlfriend’s mom’s boobs….
Curse her rockin’ tits.

My mom was a milf I guess. She was also a super tease. She would and still does dance around in her undies slapping her double Ds. This was also when my brothers friends were over even though she pretended they weren’t. She would leave the bathroom door open a little when she was in the bath tub and shed make ridiculous comments like asking my brothers friend to trim her bush. My brothers friends would come over and sing stacys mom but it would be “my brothers name” mom has got it going on. There was one guy living next door and another guy living on the other side of us that were in the same grade. They used to steal my mom’s underwear and bras and she knew it and didn’t care. After the one guy graduated high school and my parents got divorced, he told her he would take care of her… Which he did by plowing the driveway and mowing the lawn… If he ever did get laid I will never know…

Mom is 4″11 and fairly young looking and petite (Eeugh) for a woman her age I guess, she’s got like a “Asian wife” syndrome going on, only if you were Navajo. Makes it awkward where my dad looks like he could be her dad when they’re out in public, not as much of a problem now than it was several years ago.
I remember my older brother relaying a story to us about how his ex-girlfriend got angry with him because he saw him “Hugging some bitch” after school, boy did she feel stupid once he told her his mom was picking him up from school.
Coming to HS basketball games, high school boys would hit on her and be surprised to find she had 5 kids and her husband was the basketball coach.
Weird and gross encounter I had with this was in 9th grade, girl I had a minor crush on because huge boobs, thin waist and chocolate skin appeal– commented to me after meeting my family “Your mom is really attractive, like I’d have sex with her if I were a lesbian.”… okay, why would you tell me that, and gross.
Can’t really remember any specific desperate instances though, just cringe-inducing moments. One of my younger brothers friend’s who was like, 12 at the time did the “V” finger sign and licking the middle thing when her back was turned but caught it out of the corner of her eye and boy did she have no problem tearing him a new asshole and she was the type of mom to call other peoples’ moms to tell them about their children’s bad behavior… fun times.

My mom is a milf.. Once my mom and I were walking and some guy said to me in front of my mom: Girl you are cute but your mom is smoking hot.
She is 20 years older than me and hotter… Great.

As a high-school teacher, you don’t need to be attractive. Teenagers are delusional. I’ve watched as teachers have basically been forced out of schools by teen-age rumours based on absolutely nothing. As a male teacher, you have to be very careful. It can be pretty rough for women as well.
Even worse was when I was a GTA at university. The people you are working with think they are adults, and the age range is closer. Technically your career isn’t in jeopardy (you’re often allowed to engage with students), but the reputational damage can be terrible. Also: being stalked sucks.
Again: this isn’t about being attractive. It is about strange power relationships and delusional young people.

Reverse situation for me when I was 17. Had my friends mom corner me in a bathroom asking me to stay the night. Said he wouldn’t know if I snuck in her room. I’m torn because I fucking wish I had. But at the time I knew if my friend caught me, we wouldn’t be friends anymore. I say I wish I would have because we still aren’t friends anymore, but I just couldn’t out of respect. She was in her early forties and fucking hot.

And then, lastly, we have this lady:


I never get any advances from my son’s friends, that’s why I have to post on porn sites that I’m in your area and ready to fuck NOW.

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