Author: clintcr

The Young Army Officer in the Big City: Bagging my Cougar [MF]

It’s funny, now that I’m 39, I tend to fantasize about younger women. But when I was young, I had a huge cougar/MILF fantasy. This is the story of the hottest time I indulged it.

I was 24 and temporarily in the Washington, D.C. area for a few months. I was in the military, then (and still now) a 6’4″ corn-fed ex-jock who grew up on a farm in the midwest, with broad shoulders and a reasonably built body, even if I don’t exactly have the muscle definition of Michelangelo’s David.

I overheard an acquaintance at a party describe the Capital Grille in downtown D.C. as a “cougar bar,” and that was all I needed to know. I headed there the next Thursday solo, trying to play up my simple-minded young jock vibe with a tight-fitting white polo shirt. I sidled up to the bar, ordered the cheapest draft they had (maybe Yuengling?) and started looking around. The after-work crowd filtered in and out for an hour or so, and then I saw her. A 45-year old blonde dressed in a sleek black dress that was somewhere in between “work” and “cocktail.” Tits pushed to a level where they were clearly intended to draw attention. Read more »

The Hotel Bar Leads to the Hotel Room, and the Hotel Room Leads to… [FM]

*Warning up front: this story is my only time truly cheating. If that’s a problem, move on. I was still married at the time, I’m not anymore, but our breakup had nothing to do with this. I felt bad about it but, as you’ll see, it still ended up pretty hot.*

I’ve had plenty of times in my life where I’ve pursued women. A good deal successfully, plenty unsuccessfully. But some of my favorite memories are when I didn’t even realize at first that a woman was pursuing *me*, or at least was interested in a way I didn’t initially recognize*.*

When I was in my early 30s I traveled a lot for work. Various hotels in big cities for meetings, presentations, conferences. I was young and newly married, but it was fun to be in a different place for a few days every other week. Like anyone in that position, I got used to the “hotel circuit.” Hotel fitness centers, hotel restaurants, hotel bars. They all have a vibe all their own. Read more »

“Not My Type” Ended Up Amazingly Hot: Banging the “Alternative” Girl From My Gym [MF]

So, people say I’m a clean-cut guy. Deep voice, blue eyed, former military, and I literally grew up corn-fed on a farm in the Midwest. I have a body that, on occasion in foreign countries, people have said is a stereotype of an American man. 6’4″, about 200 pounds with broad shoulders, blond hair that I keep close cropped. I don’t think that appearances necessarily mean anything about your personality–hey, ask me about my taste in music or my occasional bedroom adventures with other men–but the women I’ve hooked up with have tended to be, well, what you’d expect. Not that they’re all the same, but lusting after various real-world variations on bubbly cheerleaders, Gwyneth Paltrow, and Sloan from Entourage is admittedly only one axis of women.

That brings me to Olivia. I was 36 and had been divorced for a year or two, she was maybe 10 years younger, and we met at the gym. I’m no Adonis, more of a “guy who definitely likes lifting but also likes hamburgers,” but a daily trip to the gym has been a constant ritual my entire adult life. Now, like anyone with a pulse, I check out the eye candy at the gym here and there, but never gave Olivia much thought in that respect. Read more »