Guys Reveal What Sleeping With A Real-Life MILF Is Actually Like

“MILF” may be a relatively new term, but the appeal seems to be as old as time itself. Older women offer the allure of experience, confidence, and a complete awareness of what they want. It’s no wonder that younger men across the globe fantasize about getting a shot with a cougar.

For these 10 men, their MILF fantasies actually became a reality. Read on to hear their crazy confessions, some of which show how sometimes dreams can become nightmares!

10. Not-So-Little Miss Sunshine

“We didn’t actually have sex, but it got pretty wild,” revealed one MILF hunter. “She was my youngest friend’s mother; an adorable, non-sleazy divorcee in her mid-40s. A night of drunken partying got us alone together and somehow ended in her going down on me. I promised never to tell a soul.”

9. Too Late Now

“I slept with my mom’s friend when I was a teenager,” one guy confessed. “I could barely drive, but she had assumed I was in my 20s. This made for an extremely awkward confrontation when she realized my true age.”

Hiding your age is child’s play compared to what’s coming next. Read on to see what other guys have gotten away with when it comes to older ladies!

8. Oh Bloody Hell

“I slept with the mother of a high school kid I was mentoring when I was 21,” one guy said, with a twinge of shame. “He was 18, so we had grown up as close friends. During sex, I became distracted by a picture of him in his mother’s room out of guilt. I ended up hitting my head so hard I bled! Things only got worse when I stumbled into the hallway naked- only to run into my friend.”

7. Drunk Dynasty

This sounds brutal.

“I had a drunken one-night stand with a female friend’s (newly divorced) mom in my late 20s. I didn’t think much of it again until the mother confessed what had happened to her daughter at a party I was also attending. I took a few slugs to the face from that friend that night. It turns out I had hooked up with both of them. Yikes.”

6. Sweet, Sweet Revenge

We wouldn’t advise handling it like this …

“I slept with a buddy’s mom after running into her at a club one night. I felt pretty guilty about it and kept it a secret for a long time. Years later, he poisoned me, so I broke the news that I had gotten it in with his mom via a (laxative) cookie cake.”

Unfortunately, not everyone gets the last laugh, as you’ll see in the coming entries.

5. MILF Matrix

“My MILF story was somehow like a porn within a porn.” Sounds exciting, go on!

“I went over to fix a friend’s mom’s computer, made a joke about adult films on the Internet, and BAM! By the end of the night, we were having the best sex of my life.”

4. Teddy Bear

Aww, this is kind of sweet!

“I spent the night at a pal’s house and was told I could sleep in his mother’s bed. She arrived home in the middle of the night, crawling into bed with me without hesitation. Nothing sexual happened, but she cuddled me all night only to never mention it again.”

You may be nowhere near curling up with a MILF, but that’s just the tip of the iceberg. You won’t believe just how far some guys take it when trapped by their own cougars…

3. A Family Affair

Now this one definitely sounds like porn!

“I cheated on my then-girlfriend with her mom when I was 17 or 18. I had just mowed their lawn and was chitchatting with her mother when she offered to give me a blowjob out of the blue. Needless to say, I was far too stupefied to say no.”

2. Climbing The Corporate Ladder

“I slept with my mom’s former supervisor, who was actually also my boss at the time,” one guilty dude confessed. “She was a married woman, so it remained a secret. The experience led me to sleep with even more MILFs- now no one trusts me around their mom.”

That’s one way to get a raise

1. Long Days, Long Nights

Sounds like this guy needs to change up his side hustle.

“I have been sleeping with my mom’s old pal from work for a while now. We do it everywhere- her house, her car, my house, my car, even hotels. The sex is alright, though she certainly isn’t what she was the first time I met her. It is surprisingly unsurprising.”

As mystical as it can seem, in many ways getting with a MILF can be no different than people your own age. Some guys had a thrilling experience – others, not so much. Sure, not everyone is naturally suited to such risky business. Pile on the additional pressure of having to hide your saucy activities from close friends and you’ve got a recipe for tension.

On the other hand, if you’re someone who thrives off the adrenaline of heightened consequences (or even just someone who prefers more, ahem, thoroughly-practiced partners), who knows? That wild cougar fantasy might just be a dream waiting to come true.

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