It's a fantasy that is seemingly so common amongst virile younger men that it might not even be taboo at this point. While a generation before had Mrs. Robinson in The Graduate, mine had Stifler's Mom in American Pie and it seemed as though the MILF craze had exploded. Now, I'm not one to get wrapped up in the latest trends, but the MILF, or "Cougar" trend seemed like something I could really get into. As it would turn out for me, I wouldn't be following a trend after all. Rather, my sexual attraction towards more mature women stayed with me far beyond any passing trends. Now, as I find myself frequently thinking back on these experiences, I've been compelled to tell this story first, as my very first submission to lit. Every last word is true.
Kim wasn't my first older woman, but she's one that makes for an entertaining and highly erotic tale. Before I had even met her, I'd heard of her from a friend of mine when he would boast about the older woman he was regularly fucking. So, in a way, I was surprised that he agreed when I asked him to let me have her phone number. If he told me at the time why he was done with her I can't remember the reason now, but I was more than happy to pick up where he left off.
I decided to reach out with a text, having no idea what to expect or if I should expect anything at all. Ordinarily, my first text to anyone would be cordial, polite and appropriate for all audiences. But, emboldened by the fact that I knew this text was an unsolicited advance at an older woman who I knew had a taste for a younger suitor, and appetites of which I had heard first-hand, I decided to forgo any thought of playing things safely. I introduced myself and told her where I had gotten her number, letting her know that, with his blessing, I'd be more than happy to pick up where he had left off and make sure that she needn't go without a virile lover in his absence. I was shocked that it worked when I got her response.
It didn't take long for her to agree to meet me at a bar in the suburbs. I took a cab, finding out later that she had come in her minivan. There was instant attraction when she finally joined me at the bar where I had been waiting and suffering through a karaoke night for what seemed like an eternity. She was petite, maybe 5'2" and had a small frame with smaller tits, blonde hair, her age only showing itself in her face, which was attractive with defined bone structure, full lips and enhanced by the make-up she had applied. I'd say she was in her mid forties. We embraced with a hug and I inhaled her perfume. Between the make-up, perfume and the way she had dressed herself in sexy boots and a revealing top over tight jeans, it was very clear that she had prepared herself for more than just a few drinks and a chat.
I don't remember what we talked about and it's just not even important. We both knew we weren't there to size up the other as a potential real partner, so it was unlike any more traditional date. We were both there for the drinks to break the ice and lower inhibitions. She must have had five or six mixed drinks and I had downed at least as many beers before we left. Thin and petite, the booze was hitting her hard and she asked me to drive us to my place in her minivan. Drunk and horny, her hands were all over my crotch, legs and chest as I drove her family vehicle to my bachelor pad. Everything that made the situation at hand feel completely wrong only made my lust grow.