I remember it like it was yesterday. Somewhere in 1999, Blink 182 was roaring, Spongebob had just debuted, the Backstreet Boys and N’Sync boy band duel was in full swing, and American Pie had just come out. One fateful day while playing street hockey with my buddy Andrew, he asked me, “Hey man, you know that movie American Pie”? Of course 10-year-old me had heard of it. Everyone had. It was popular and there were tits in it. This was before the internet was huge and porn was easily accessible.
So we went inside, got some Ecto Cooler and popped in American Pie on DVD (DVDs were pretty new and they were rich) and watched the exploits of Jim, Oz, Finch, Kevin, and Stifler. He had cool parents and they had purchased it for him. I watched intently as these five fellows embarked on the noble quest to lose their virginity.
I knew there would be tits. While I commiserated with Jim the best way any 10-year-old could, what really interested me was Finch and his exploits with Stifler’s mom. After watching Stifler’s Mom grace the big screen (32-inch televisions were huge at this point), I was smitten. Thus began a lifelong quest of my own: to have sex with a hot older woman.
Be honest with yourself, guys: every man wants to bang a MILF. John Cho’s chant, “MILF, MILF, MILF” brought the “Mom I’d Like to Fuck” to the mainstream. MILF became a piece of culture. An icon. Many famous out of work porn stars rejoiced, knowing that even though there wasn’t much tread on the tires, a new genre had entered the playing field. You’d be lying if you said you didn’t know Lisa Ann, Nina Hartley, or Kendra Lust.
I had my own run-in with a MILF when I was lugging golf bags at a local (but upscale) country club. My summer job through college and grad school was to caddie in the morning and work bagroom after a 14 hour day, four to five days a week, for 11 years. Many of the members were wealthy men and trophy wives. These types were easy to spot: goofy looking bankers/lawyers/hedge fund managers with bombshell wives 10-20 years their junior. They probably never lifted a finger in their lives and were always clad in the finest clothing money could buy.
Hell, some of you may have also worked at a country club and some of you may even be the product of a trophy wife. One thing is for sure: these women loved to flirt. I was a great caddie and I had a college degree, putting me head and shoulders above many of the others that enjoyed the 80s too much. I was on the bag for the club champion in 2010, a feat for caddies. I dreaded Thursday (ladies day) as these catty women came out in droves to hit worm burners only to finish six hours later (if I was lucky).
My first encounter with a MILF was a woman named Jane. Looking back, I realize my colossal fuck up. She had just divorced her husband to the tune of $13 million American and decided she was ready to let her hair down. Jane was single and ready to mingle. She loved to chat and ask about my college experience, girlfriend at the time, my Greek experience and other semi-sexual things. I caddied (watching her dig holes with her clubs) for her often as she’d request me nearly every week.
After her divorce, she made sure to slip my meager forecaddie fee into the side of my pants and lingered longer than appropriate.
On one particular day, after several rounds of Transfusions, Jane decided she was going to play at another trophy wife’s home course. I dutifully retrieved her bag from the bag room and left it at the bag drop. Having to deal with annoying members all day was draining and I just wanted to go home.
When she pulled up in her Jaguar, my boss, Greg, had gone to greet her. Jane was walking over to her bag, knowing she couldn’t lift it up. He asked me, “Could you please put Jane’s bag in her car?” I trundled over, wondering why he couldn’t do it. Lazy fuck. Jane had one of those golf bags that felt like it was filled with cannonballs and made of lead. I had to lift with the legs and wondered how this 130-pound, well manicured, 45-year-old woman was going to get it out of her car when she got home.
Greg told her, “If you’d like, we can send Bernie home with you to unload it for you.” Thanks, asshole. To which she replied, “I haven’t taken a man like that home in years”. But, for whatever reason, I didn’t go.
While blushing, I had a realization: my great awakening. This whole fucking time I could have banged a very attractive, wealthy and horny old lady. I let a lot of people down that day, most of all myself. And to this day, I still kick myself for it. These opportunities are once in a lifetime. If only coach woulda put me in fourth quarter, we would’ve been state champions. No doubt. No doubt in my mind. .
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