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Latest HUSTLER Magazine cover issue
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April 2024

Featuring Kendra Sunderland
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The DILF Dilemma
Featured Article

The DILF Dilemma

Silver foxes, take heart! There are plenty of younger hotties out there who go for older dudes. But beware—chasing after a woman young enough to be your daughter can be a perilous path.

Nearly every young man around his coming of age has developed what might be considered an unhealthy attraction to one of his friend’s moms. And it’s easy to see why—especially in this day and age. After all, in modern times, your buddy’s mamacita ain’t no mumu-wearing housewife. She’s fit—we’re talking, you could bounce quarters off parts of her body that should have started to sag by now. To top it off, she has an amazing personality, laughs at all your jokes and oozes more sex appeal than any of those fraternity girls from school could ever hope to. Our reaction to these stacked specimens of sheer sexuality is beyond our control. One minute we’re outside shooting hoops with a pal, the next we’re in the bathroom, digging around in the clothes hamper trying to find a pair of his mama’s dirty panties to sniff. Hey, young lust often comes from out of nowhere, and MILFs will always turn young men into defenseless puddles of pecker juice. 

But decades after our first MILF fixation, the script has flipped. We have families of our own, maybe even a daughter or two in college. These days, they’re the ones bringing friends around. Although we try not to act like dirty old men around their porkable peers, we can’t help but think at times that maybe their nubile gal-pals are looking at us fathers the same way we did our compadre’s mountable matriarch back in the day. We might even catch a word, line or what we think is a glance here and there suggesting that they find us attractive and might even do us if the circumstances were different. 

Of course, that’s a big if on a number of fronts.

“My daughter has this one friend that always seems to flirt with me when she’s over,” 47-year-old Gregory tells HUSTLERMagazine.com. “I’ve resisted the urge to flirt back. She’s probably just being nice.”

“One of my dorm-mates back in college invited me to their dad’s house over Memorial Day weekend. He was so nice and welcoming and very hot too. That was the first time I ever saw an older man that way.”

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