Sexy Older Women Reveal The Most God-Awful Ways Younger Men Have Hit On Them

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No matter what anyone says, every single guy out there has had the fantasy of sleeping with an older woman at one time or another. That doesn't mean we sit around and fantasize about a buddy's grandmother or anything, but, let's face it, if there's an attractive 50-something woman, we're going to have dirty thoughts run through our minds.

Movies like The Graduate, American Pie and Animal House all paint this very image, with a younger, overzealous and confident young man trying their best to swoon an older lady into the bedroom—with all accomplishing their mission.

However, this is more the exception than the rule, and, to further echo that, some MILFs took to Reddit for an "Ask Me Anything" to put all us sorry, hopeless dudes in our place, as the women revealed the most desperate attempts from younger guys to try and pick them up. Here are some of the best, er, worst.

  • "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." - rooneygirl420

  • "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." - Colombiana

  • "He put his arm around you, and you yawned and said "boy am I tired, I should go to the bedroom" to a 14 year old boy? He's probably still confused to this day hahahahha." - Tanefaced

  • "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." - inconditenarrative

  • "Called a girl I was dating who had a daughter a milf once in a playful fashion. She was not a fan, and it was never repeated." - throwaway08255

  • "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." - anothermochaplz

  • "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." - psychicjak

  • "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." - SuperHighSkiBunny

Ouch. It's almost as if we can see the Titanic sinking and, rather than call for help or do anything to try and save the passengers, we grab our camera to take a selfie to capture the epic moment of history.

Yeah, we wish we could help these gentleman from being rejected, but, hey, they're the brave—or poor—souls who put themselves so far out there that these older ladies put them in their place to teach them a lesson.

Our personal favorite is the kid who blatantly said he'd “like to experience an older woman” and then just stared at the woman—who was his friend's mom. Yeah, uh, that's not creepy at all...

To see the full thread, head on over to Reddit. Just remember to avoid doing these things at all cost if you're ever in a similar situation.


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