My Cougar Dating Story

One year ago…
She’s sitting down the bar twirling a tiny straw around in high ball glass of what I presume is a gin and tonic. She’s got a tight body and is all prettied up with make-up, hair and a sexy outfit, a bit overkill if you ask me, well at least for being [...]


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One year ago…

She’s sitting down the bar twirling a tiny straw around in high ball glass of what I presume is a gin and tonic. She’s got a tight body and is all prettied up with make-up, hair and a sexy outfit, a bit overkill if you ask me, well at least for being in a small dive bar on a Tuesday night. She’s definitely older than me, probably in her early forties, about ten to twelve more years than myself. She keeps making eyes at me; those extra long stares, some people might call it the “fuck me eyes,” but whatever it is I know there is definitely some attraction.

I flash her a few smiles and acknowledge her flirtation. At this, she rises from her bar stool and walks directly over and sits next to me. Her legs crossed in a way that exposes her upper thigh and her cleavage stretching tight against a thin black blouse. She immediately opens up to conversation, introducing herself and exclaiming how she never approaches guys at bars like this…yeaaa right! It’s at this moment that it dawns on me. She is on the prowl. Oh my god, it’s a cougar!!

I had often heard many great cougar dating stories from some of my more sexually active college friends, stories that seemed beyond the realm of possibility to me, but tonight it looked like the cougar was finally attacking my scrawny nerdy boyishly handsome self… alright maybe I’m embellishing a bit but hey, I look young!

By the way, for those that don’t know, a “cougar” is a slang term for an older woman who pursues and dates much younger men, with the age disparity usually having a gap of at least ten years or more.

The cougar dating scene has really only become in vogue recently, within the past decade, as previously this type of behavior was taboo or socially unacceptable for older women at the time. However, now cougar dating is almost catching on as a fad. It seems to evolved to the point where it’s a sign of power and individuality for those older women. Some of them are divorcees simply looking to have fun, not ready to settle down again. Some are high powered executives who are more dominant and looking for a boy toy. I can’t really say where the term cougar came from but it seems to fit well as a metaphor for this type of womanly behavior.

Ok, lets get back to my story…

Finally, after she buys me multiple rounds of drinks and we have a lengthy yet flirtatious conversation, we end up back at my place…yadda yadda yadda… I now have my own cougar. Well actually she has me.

The next couple months go great. Basically she calls me on random nights when she’s feeling energetic, it’s always on her terms, but the best part is she always buys when we go out, or brings me beer or wine when she comes over. It’s almost like have a sugarmama I suppose.

Whatever type of relationship we have, it’s certainly not a serious one and it can’t last. And as with most cougar dating stories this one ends up with an unemotional and mutual ending. I can’t say that it was one of the most meaningful relationship I’ve had, it wasn’t at all, but holy shit, the sex was fantastic!

Present day…

So that little gem of a story occurred well over a year ago now. I’m not really looking for anything like that now. I really want more of a committed relationship a little closer to my age range, which is why I am still scouring the online dating scene. The experience was certainly nice though for a little fling and I learned a lot in the bedroom as well, which really helped me out. So in that respect, for you single younger guys out there looking for a little more experience I actually recommend finding yourself, or at least being prey, to lovely older woman.

There are even niche online dating sites popping up these days devoted particularly to cougar dating to help make the process more efficient. Hell you could probably even find plenty of them on free dating sites like Plenty of Fish if you look hard enough.

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1. 10 F*cked Up Online Dating Stories


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4. Vegetarian Dating Options?


5. Don’t Be a Plenty of Fish Nice Guy