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The Underwear Drawer: 50 Shades of Dating Men of A Certain Age

The Underwear Drawer: 50 Shades of Dating Men of A Certain Age

Written by: Langston John Blaze

The thing about dating successful older men is that they’ve experienced so much, they don’t have time for drama. I never had any intentions on dating a man twice my age. It kind of just happened. I met Michael White, a marketing executive, three summers ago at the Woodruff Art Center in Atlanta. His friend, Kelvin Brooks, was a popular and somewhat sassy (which was a nice way of saying diva) event coordinator in Atlanta. Brooks had organized a gathering at the museum. He could find any excuse to throw a hot party. Brooks was 40 something. Often, he flirted with me through social network sites. We’d met through a friend of mine who introduced us when I was interested in throwing a book signing party for my first novel.

However, I definitely could not afford the shindigs the coordinator threw. We kept in touch through Facebook. He would constantly “poke” me on the site, a stupid feature which allowed you to virtually flirt or greet in a friendly manner. I would poke him back, but I didn’t think anything of it. I knew Brooks was older. What future could I have  with a man twice my age? I thought. Nevertheless, the shit hit the fan when Brooks decided to be ballsy and profess his attraction to me. Nicely, I told him I was only interested in a business friendship with him, which didn’t blow over so well when he felt the need to call me out on my response at his gathering in front of his entourage of older male friends.

Not one for confrontation, I let the diva have his moment. I spent the rest of the evening talking to a 30 something year old man named Braxton, who was familiar with Michael White. He told me how prestigious his reputation was for his work in marketing. He also gave me the 411 that he was a gym junkie, working out five days a week, and he was also Panamanian. I called him Blair Underwood, seeing as though he had a similar look to the actor.

Later, Braxton introduced us. As he carried on his way, I got to know Michael for myself. He was sexy, charming, built, and some times goofy. A week after the party, I visited Michael at his place on the opposite side of town from me. I didn’t know what my intentions were. What are you about to get into, Langston? I asked myself, driving the half an hour ride to his home, a home I would discover was more like a mini-mansion.

His place was like something on an episode of Extreme Makeover. He even had a mini movie theater. I was astonished. Briefly, we watched a flick. This was after his retriever, Spike, spilled his glass of wine all over the white carpet. “Oh, don’t make him feel too bad,” I giggled, defending the K9. After getting the mess up, which did leave a stain, somehow I found myself in Michael’s hot tub, accompanied by Mr. White himself. I’d never felt so passionate with a man before. It was like being with someone for years and just taking the time to experience each other and reflect on the relationship. I didn’t want to get Michael too excited that night. Frankly, I did not know what I wanted. I had not been with a guy this intimately since my first time, which was so bad, I wanted to make it my last time.

Yet, I experienced magical intimacy I could never forget; well, there was a few times he showed his age, referring to his back issues, which I rubbed out for him. We gave each other passion. Yet, it got real when we had a brief discussion of our age difference in the shower. “How old are you?” Michael asked. “Twenty-two,” I replied. “Wow,” he said. I smiled. “What?” “I’m old enough to be your grandfather.” Yikes! I thought to myself. I knew he was older, but damn, I was walking down Sugar Daddy Avenue. “How old are you?” I asked Michael back. “Thirty-one years older than you,” he responded. I knew that was a lot but I hadn’t done the math in my head.

I was more caught up in the fact I was in a sexy 50 something year old’s mini-mansion, watching movies in his theater, relaxing in his hot tub, and doing a little more than resting in his bed. His bedroom looked like it was made for King Tut. There was a white fur blanket and steps you had to go up before getting on the mattress. Michael brought out every sensual trait I had inside me. I wasn’t the shy twenty-two year old submissive boy he expected me to be. I was dominate. I liked to take control. He responded to it pleasantly.

By the time I was ready for round two, Michael was tucked in and snoring like a beast in hibernation. I assumed you only got one round with men of a certain age. Nonetheless, I enjoyed myself. Wide awake through his snoring, I pulled out my phone to calculate our age difference, trying to make sure the math in my head was correct. Yep! Michael White was fifty-three. Oh my God, I’ve gotten busy with a fifty-three year old man I thought. But damn, he’s sexy though I presumed to think, listening to his monster snores.

That morning, I got dressed alongside Michael, who was getting ready for church. I reflected on last night and wondered, Could I date an older man? I was beginning to consider it. And just then, as Michael was giving me directions on how to leave his maze of a subdivision, I began to feel like his son. It was the way he said, “Pay attention.” That moment made me think about the pain on his face in the hot tub when he told me about his back problems, which also made me think about no round two, and that “old enough to be your grandfather,” comment in the shower. It was all a turn off.

Often, I found myself using small situations to let me know how a bigger situation would turn out. Michael was fun but to date him potentially meant experiencing things on my own that he would have been through years ago. How could I relate to him?

I didn’t see Michael again until a few months later when Brooks threw another party. We talked casually and danced a few times. Briefly, (and I do mean brief) we hooked up again the following summer. It wasn’t long afterward when he fell asleep on the couch and I had a vision of my grandmother falling asleep on her love seat and laughing when I’d catch her dosing off. Every time I see Michael now, I think of our special night together. I might not have been ready to settle down with a sugar daddy, but venturing the avenue was certainly a memorable time.



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