First time with an escort: A male-to-male perspective

What do you do with a client who’s never been to an escort, or who might still be in the closet and looking for answers? The most important thing to remember is you are not a licensed clinician, so stay away from psychoanalyzing. But, if a client comes to you not knowing what to expect, consider what your first time was like, and be cognizant of what you’d want from a first time experience with an escort.

by Jake S.

One of my first jobs as an escort was working at a massage parlor in New York City. It wasn’t as bad as one would think, however I knew it wasn’t the kind of place I would be at for long. Still, it was a great way to make money while pursuing a mediocre performing career and was another notch in my belt of the things I can say I’ve done.

One of my first clients was a German porn star. I can’t make this up if I tried.

He simply wanted a nice massage with a happy ending from a hot guy and to be on his merry way. He didn’t speak much English, but there was honestly no need for talking when it came to the work. He was a professional and I sincerely appreciated that.

But my next client was vastly different. He was a young kid, on tour with a local theatre company, who heard about the place from a friend and thought he’d give it a try. He was hesitant while walking up the stairs, but I could tell he was really hoping for something spectacular.

The Mr. of the establishment lined up the boys and after a fairly awkward introduction session, the kid chose me. I was kind of excited because he was around my age and I really wanted to make money. I knew that this was going to be a positive experience for both of us.

I walked him down the hallway to the Venetian room; a very gay affair. However, the lights were always so dimly lit, one could never fully appreciate the fine, faux antiques or cheap, tawdry wallpaper. My music was set to play in a matter of moments and the lotions were prepared in an even line on the table accordingly.

He was a skinny kid, no more than 130 lbs. He had a bandana on and was pretty shy about taking off his clothes. So, I didn’t want to rush it. I started a conversation to gauge him. Off the bat, it’s so important to make your client feel absolutely at home with you.

“Have you been in town long?”

“No. I’m on tour with a show.”

“What do you do?”

“I play the lead in a touring company. I miss the Midwest though. I’m not really a big town kind of person and these long tours are killing me.”

“Well, this is the perfect place for you then to relax and unwind. Can I get you something to drink?”

“No, thanks. I’m still pretty nervous. I almost don’t know what I’m doing here. We don’t have these types of things where I’m from.”

“And what types of things are you referring to… I didn’t catch your name?”

“I’m Andy. And you are?”

“I’m Jake. It’s a pleasure to meet you.”

I could tell that this was Andy’s first experience, probably with a guy, so I had no intentions of rushing something that could likely take a while. After all, we are in the business of pleasure, and any job worth doing is worth doing right.

I proceeded to take off his jacket and to hang it up on the hook behind the door. It was clear that I was fully in control of the environment, which is a must with any client. I walked gently over to the table where I could see he had unbuttoned the top button of his flannel dress shirt.

“I would assume that most leads in a professional touring company have had at least one erotic experience?”

I waited for his response to my bold question to see what my next move should be.

“No. I’m Mormon… I was raised Mormon… I mean, umm… I’m a Mormon.”

I could sense some difficulty, so I backed down and went another route.

“Cool. I like Mormons! I know a lot of Mormons – even a few gay Mormons – and they’re pretty great people. Do you miss home?”

I wanted to get him to talk about home because it was on his mind. I know that if we started our session too soon he would be thinking of other things rather than what was happening in the moment. So, this was his chance to get things out beforehand.

He spoke a bit about how he was raised and what an influence the church had on him and his beliefs. He then started talking about how he used to feel attracted to men, but he masked his feelings by talking to girls in the hopes of one day marrying one of them. Magically, whatever he was feeling would likely subside.

“I wouldn’t dare share my feelings with anyone, they wouldn’t understand. Plus, the church would have done terrible things to me and my family so I just decided to hide it.”

“Well, have you ever had a girlfriend or a special friend?”

“No, but there was this one time…”

He went on to talk about how he and his best friend went up to the big BYU sign in Provo. He’d wanted so badly to tell his friend all the things he was thinking and feeling, but never had the opportunity. He described the scene in vivid detail.

“It was perfect, dark and crisp. We could see the lights of the city below us like an electric grid, all squares and silent. It was just him and me and I couldn’t stand it any longer. So, I…”

“…yeah?”

He hesitated and said, “I just couldn’t.”

I then had a brilliant idea!

“Well, what about now?”

“Huh?”

“I’ll be your best friend and you’ll be you and we’ll both be on the mountaintop in Provo together.”

“Are you serious?”

“Absolutely. Look! Can’t you see the stars up there and those little lights all flickering below us?”

From that point on, Andy and I were playing make-believe in the middle of an all-male massage parlor in New York City. We tried to be as quiet as we could and eventually it livened him up enough to start to take his clothes off. He laid down on the table, his heart was pounding, and I proceeded to work my magic.

He was smiling. I had met him exactly where he needed to be met and he was grateful for it. After that, it was smooth sailing.

The most important thing is never to assume anything about a client. We are in the business of trusting our instincts as the most important survival mechanism we have. And one thing that will help is recognizing the humanity in a person. It will both give you the confidence you need to protect yourself accordingly as well as stay in control of the situation at all times.

I realized that Andy was an artist and his imagination was both his best friend and worst enemy. If I didn’t coax his fires the right way, the session would not be as successful as it was. He needed to feel safe and protected and in turn provided as handsome a compensation as he could muster.

My recommendations for handling clients who have either never been with a man or a male escort before is this: never trust first impressions, ask the right questions, obtain the right answers, and never press too deep into a subject. If you feel uncomfortable steer the conversation to something you know will bring him pleasure, which is not always sexual. Listen to him beyond what he’s telling you. Clients say a lot without telling you much.

Don’t be afraid to try new things as long as it’s safe and meaningful. A lot of what we do as escorts is tinkering the imagination, not just the physical apparatus. Many customers will likely have wishes and desires that can only be expressed in role-play. That’s why it’s so important to keep your cool, try new things and to never loose sight of the power of your imagination; not just for the job, but for survival, and in life in general.