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What It’s Like Servicing an Older Gay Man When You’re 21

I learned something about myself and wisdom.

Age Differences in gay Relationships

By: Eddy in Chicago

When I was 21-years old on summer break from college, I hooked up with a significantly older man. It happened with a guy from my neighborhood. I was 21 and he was 50.

You read that right – he was nearly 30 years older.

But the age difference didn’t matter. At least not to me. That’s because I was extremely attracted to him. His name was Mike* and he was a tattoo artist from a local parlor on Chicago’s north side.

We got to know one another when I came to him for some ink. A superman tat to be exact. Corny, right? What can I say. They were “in” at the time and I was naïve.

But I digress.

Our encounter wasn’t all that unusual. I was walking down the street on my way back from the post office. He saw me from his car and offered a ride.

“Need a lift?” he asked in a laid-back voice.

Once I jumped inside, we started making small talk. But that didn’t last long. At some point, his hand drifted towards my lap. In turn, mine crept to his crotch.

As I write this now, I can still remember the excitement of it all. If you’ve ever hooked up in a car, you know the thrill comes from the fear of getting busted.

As things heated up, he turned to me and said, “I know a place.” Moments later, he steered the car to the lakefront and parked along a quiet area called the Belmont Rocks.

In gayspeak, Mike would fall into the muscle daddy category; well built, older and in his case, totally bald.


I suppose that’s why I really got into servicing him as he sat behind the driver’s seat of his 68’ El Camino (baby blue if I recall). Just before he released, he jokingly said: Son, don’t let one drop get on the seats.  

He didn’t have to worry.

Bear in mind, Mike was my first “older man”. In the past, I had messed around with other guys but all of them were my age (ish). Looking back, I now realize how profound that encounter was.

That’s because in doing Mike, I learned a thing or two about wisdom. That may sound silly but if you hear me out, I’ll explain.

To begin with, I didn’t have a lot of experience with oral. Well, at least giving good oral. It took an older man to teach me the “how” of it all without getting toothy.

Patiently, Mike talked me through it and literally said, “Follow my lead.” Without missing a beat, he showed me the importance of hand, mouth coordination, using my willy as a guide.

Second, he took his time. Unlike many of the guys my age, he didn’t make it a rush to the finish line. Instead, he was patient – in the way only an older man can be.

Sure, there was the adrenalin rush of it all. And yes, there was the danger factor. Chicago PD regularly patrolled this area. But regardless of the threat, he remained steady and focused.

Occasionally, he’d even kiss me. And not one of those sloppy, hurried kisses either.

Instead, he cupped me from behind my neck and pulled me close. Even now, I can still smell his cheap, dime store aftershave when I think about it.

But here’s the thing – he knew what he was doing. And I can honestly say it was the first time I’d ever been with a man whose confidence turned me on.

Mike used my name, smiled and ran his whiskers along my you know what for extra stimulation. To this day, nobody has done that.

Our hookup in his car wouldn’t be the only time we fooled around. There were other encounters. Sometimes they happened at the shop (after it closed). Other times, we’d mess around in at his place.

Each time we met, I learned something new being with a man. Namely, patience, skill and technique.

When I returned to college that fall, I knew I would probably never see Mike again. That’s because he had previously hinted at moving to California.

While I never asked “why”, I got the feeling he was just looking for a major life change. Given the frigid winter temps in the windy city, I can’t say I blamed him.

All of this is to simply say that when you are young, it’s easy to gravitate towards men in your age bracket. I know I did. But if you can step away from your norm and try something different, you allow for the possibility of new insight.

In my case, I learned that guys who are comfortable in their own skin are incredibly sexy. That “comfortableness” doesn’t happen by magic. It occurs through experience, which ultimately leads to wisdom.

To this day, I still think of Mike whenever I get a whiff of Brute aftershave.

Thanks for reading. 🙂

*Name changed per author’s request.

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