Boys to the Yard, Men to My Bed

“My milkshake brings all the boys to the yard...” Kelis croon-brags on her iconic song, “Milkshake.” While she certainly isn’t using the lyrics to advocate for pedophilia, they certainly can be examined that way. This process lead me to declare that only men are allowed to experience my milkshake. Men rolled their eyes saying, "that was the implication," but females were a tad more concerned about the meaning of the song. It also started a conversation about age and relationships.

On one of the gay “dating” apps, a 19-year-old messaged me. Normally, I would have ignored that message, but physically he was everything that I wanted: blonde hair, blue eyes, football player's build, and a monster between his legs. While we talked and exchanged pictures, he kept insisting that he was just curious and not gay. Sign me up, honey; I’m yours for the taking.

When the hookup finally happened, it was everything I feared it would be. The actual sex was amazing; he was 19 and an energizer bunny in bed: willing to do anything that was asked of him, an eagerness to please that is not found in many older guys. There was nary a flinch when I asked him to toss my salad, something I’ve had to cajole and plead with other men to do. So what was the problem?

As good as the sex was, he wasn’t emotionally ready to deal with the realization that he liked guys. From the virile, beast of a man came a scared young adult that had no idea what it meant to be gay in his world. He turned to me for the answers, but I’m a writer; the closest I’ve ever come to a football is touching the players that handle it. Trust me; football is one of the most homoerotic sports out there. Most of the players have at least experimented with a guy before. Once I helped him find a group that dealt with coming out, a decision was made that an older man was needed.

Finding an older guy in New York is like shooting fish in a barrel. Maybe you’ll miss once, but you’re bound to get a hit eighty percent of the time. Older Guy was also handsome, albeit differently. His hair was dark but peppered with grey; his body was what could be described as "the quarterback who gave up his dreams" (slightly overweight but carried it well) and like Younger Guy was well endowed. He also insisted on going out on a real date.

That was fine with me. Who would turn down a free meal? The first surprise of the evening was that the conversation was the most erotic part of the evening, and there was no need to talk about dick to get the arousal going. After dinner, he took my hand, and we walked around the city. At the pier, I looked out at the water as he began kissing my neck. A quick cab ride later and we were undressing in his living room. Like the younger guy, he was eager to please but took his time. The kisses, the bites lingered. My body was in ecstasy. When he performed analingus, there was an orgasm (first and only guy that made me do that). After we both finished, he held me in his arms. For six blissful months, we dated. Ultimately, he wanted more than I was willing to give him.

Were age and maturity the big decider for me? I spent six lust-filled hours with the Younger Guy—a fantasy come to life. While the Older Guy and I shared a genuine emotional connection, he also wanted something from me that wasn’t available. Some in my circle have argued that I was the problem. That could be true, but the experiment started to see which was better: a Younger or Older Man. The answer is the title of this piece: "Boys to the Yard, Men to My Bed."