Boy Toy

Ever since puberty struck I’ve had a thing for older men. It started with Mike Catrambone; he was the first guy I swapped spit with. It didn’t matter that I was four inches taller than him or that his braces gave him a slight lisp, he was fourteen and I was twelve and that was all I needed to know to make out with him under the docks at sleep away camp.

After little Michael, the streak continued. I like mature men, men with experience, men with some wisdom that can inspire me. In all my dating years I have never been out with a guy my age and certainly had never considered going out with anyone younger. This was until a very sexy, talented friend of mine gushed to me about how much she was enjoying her boy toy. “I get to be the boss,” she bragged. “Everywhere except in the bedroom.”

This arrangement appealed to me. I’m fairly controlling, I wouldn’t mind having a young lad at my beck and call. My feet are not going to massage themselves. I’m 25; I think it’s safe to say I have a few years left until dating a younger man would qualify me as a cougar.

When Chad messaged me on OKCupid I saw he was a handsome young chap, his brown eyes struck me as murky pools filled with profound mystery and maturity. He was wearing nicely tailored suits in three out of four of his pictures. Menswear gets me hot.

His profile wasn’t showy or heavy on details but it still intrigued me. He wrote that he was “an Englishman living in New York”. Well dressed with an accent? Somebody slap me.

When I noticed that he was 22 I was bummed and ready to click onwards to the next but then I thought back to my friend and reconsidered. Why not? That’s the beauty of online dating; you have nothing to lose by trying out men who typically wouldn’t fit your mold.

I agreed to meet Chad for a drink. The bar was crowded when I arrived so I messaged him, “I’m the girl in the blue striped shirt.” When I looked up I saw a young boy with a Justin Beiber inspired hair-do scanning the bar. I looked to my left and right and noticed there were four other girls wearing blue striped shirts. The nautical look is taking over.

I let him sweat it for a moment, his cheeks turning a rosy shade of red. I finally raised my hand and he awkwardly rushed over in a flustered Michael Cera-style, his cheeks reddening with every step. He didn’t look like the confident suit-wearing fella from his pictures; he looked like the missing member to a boy band.

When we started chatting I immediately noticed there was no hint of an accent coming from the man-child. When I brought it up he broke out into a fit of nervous laughter and explained that he moved to the states with his family when he was six. I thought it was unfair of him to refer to himself as an “Englishman” in his profile but I let it slide because he was clearly on edge.

“What are you doing in the city?” I asked.

This brought on another series of giggles, “I just graduated college,” he said, looking away as if he didn’t want to embarrass me, the older woman.

Every question I asked him evoked bashful and embarrassed responses. I was doing the regular: “Where you from? Where do you hang out? What neighborhood do you live in?…” But by the reactions he was giving an onlooker would have thought I was asking him how many times a day he masturbates.

My presence was obviously making him uncomfortable. I think I must have come off too dominating. Will, my HowAboutWe date, told me I had that habit. “You’re very self-assured, I think it’s probably intimidating to the guys you’re meeting from the sites,” he warned me.

When we finished our drinks I asked him if he had any big weekend plans. “Probably gonna get some forties and drink them in Fort Greene Park with my bros,” he said.

The kid can wear a suit and take an excellent self-portrait. I’m sure he’ll have a bunch of fun in the city but I think the window for me drinking forties in the park ended years ago. I definitely didn’t want to be this guy’s boss.



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