It has always felt possible to slip into the world’s oldest profession with Grindr.
I, like many other queers on the apps, have been offered money in exchange for sex or adjacent activities. You can’t help but question Could I be an escort? Would I be good at it? Would I enjoy it?
On yet another of my entirely innocent scrolls through Grindr, I came across Caesar*, a rather gentle-looking giant offering ‘services’.
I was awed, Caesar came across as unassuming and geekish with tousled hair and an awkward stance.
How successful could someone that looked like him – that looked like us – be in the escorting industry?
And so, Caesar tentatively agreed to tell me all about his escorting on the condition I came to his place as soon as possible.
With no preparation and half an idea of what I wanted to talk to him about, I madly cycled my way to Caesar.
I was intending to explore the world of escorting and operating a business on Grindr, but then I was presented with a whole other story.
—
After a mad dash and plenty of Dutch stairs on a race to get my interview, I was panting in Caesar’s apartment.
He observed me furtively, calculating my demeanour as he led me to his couch. I sensed his nerves and it made me apprehensive to probe him with personal questions about the typically taboo.
But I wasn’t about to waste my chance and jumped onto the information that initially piqued my interest.
“You told me you are moonlighting as an escort. Why escort on the side?”
Despite appearing shy, Caesar was so open, ready to pleasure my need to have questions answered.
“It started a bit over three years ago. It started out of necessity, because I was a student, I was a bit short on money and I thought What are the options?
And then, after a hookup with this guy, he was telling me how he was a sex worker. I got a bit interested, and I started a little bit of research.
I realised it was something I could maybe do as well. Then after starting escorting for a while I just enjoyed having the extra income and I just kept it up.”
And so, it does happen in the real world, it isn’t solely the plots of many an erotic novel or porno. People see a way to make money and think, Why not?
So, for these ‘why not’ escorts, do they get any sexual gratification from providing services?
“I do enjoy it. Sometimes I really do enjoy it, other times I just do it for the money. It depends on the client – if we have a good connection or if I am attracted to them.
But overall, I feel I do enjoy it. I like to experiment. I like to pleasure.
I started out of necessity but if I hated it, then I wouldn’t have kept it up.”
My impression had always been escorts were reluctantly kinky – that desirable people didn’t need to be or enjoy being kinky. But, since developing my understanding of the sex positive movement, I wanted to delve into the nuance of doing what you love or doing what others love.
Caesar has mainly submissive clientele and shared his enjoyment of being dominant and in control.
But, massages turned out to be one of Caesar’s unenthusiastic services he did for the money, despite it being one of his most popular services.
Caesar also gives in to provide other kinky requests, like puppy training, toilet training and even, slave training. But he offers that at a higher price.
“If they agree, then it’s good. If they don’t, then maybe I won’t do it, it’s a bit out of my comfort zone. Especially to do it with a stranger.”
In a tangent about slave training, Caesar raised a struggle of my own, encounters with chemsex and those who partake.
“This guy asked me to be really physically violent with him. Like, I’m talking about punching and kicking. It was pretty intense, but he was under the influence, so he was a bit numb.”
“Do you come across that quite a lot? People being under the influence?”
“Oh, yeah. But they ask me if I’m okay with it. They also usually ask me if I want to join. But most of the times, I’m not super comfortable. It depends what substance.
I try not to mix the two things, because, you know, you’re more exposed, you’re more vulnerable when you’re doing drugs. And I don’t really love that.
I want to be fully aware of what’s going on. So most of the time, I don’t agree.
I do see a lot on on Hunqz – the escorting website I’m on – that most escorts are chem-friendly. They clearly state it in their profile.”
—
“Are there any memories from your time starting out that really stick with you?”
Caesar had a mix bag of memories, he started with a sweeter one. A client who eased his anxieties of escorting and asked him out after their appointment.
But with the good comes the ugly.
“There was this other guy… another memory that has stuck with me… it was a bit weird with him.
This guy basically asked me for an erotic massage. And, maybe because I was physically attracted to him, I started doing a little bit more and made him uncomfortable.
I apologised, and then he said, Well, if you wanted to have more, you should have just hooked, hooked up with someone from Grindr.
And, he was right. You know, he asked me for something. I did something more. And it was not really what he expected.”
It was definitely prying but I couldn’t help it, the question was practically thrumming in the air between us.
“Can I ask what you did?”
“I just started to be more physical, kissing him and masturbating. I was touching his dick. A bit more than just a simple massage on the body.
I think I started doing that, because I kind of sensed from his side that he was enjoying that, and he was aroused, like physically.
So I thought maybe that’s also what he expected.
A lot of people just ask me for an erotic massage. But then what is an erotic massage? Sometimes the boundaries are confusing when they are not predefined.
So after that, I started offering more differentiations in my services.”
—
Caesar was easing, letting go of his upright posture and sinking further into the couch with me. Despite, uncomfortable memories and questions, he had a quirk in his lip and I sensed relief.
I imagine if it were me and I started escorting out escorting, I would have pushed aside my concern to consequences.
“Are you happy with how it’s all gone?”
“Yeah? Yeah, I have to say though… My partner is not fully aware of what I do. I met my partner around the same time – I actually started shortly before I met him.
He knows that I’m meeting people. He doesn’t fully know the extent of what I offer.”
There it was. A chink. The illusion Caesar had created warped, it wasn’t all sex and money.
We had spoken about his relationship prior to the interview and he had shared that his partner and him were open. So his being in a relationship not the cause for shock, the lies were.
“I told him I was an escort after three-four months of seeing each other. We were not super official yet. It wasn’t a shock to him.
My plan is to slowly decrease the frequencies of my sessions.
I think at the beginning of seeing each other, we were keeping things pretty open. We were doing our own things as well. So, when I told him, he was fine with it but he did mention that in the future, he didn’t know if it was gonna be like an issue for him.
When we started dating, we were monogamous for about a year and a half. We had agreed that I could keep up the business up on the condition that I wouldn’t do much else other than massages. He told me he was okay with erotic massages but wasn’t super comfortable with me doing the full thing. So, that’s the part that I kept secret for like the first year.
He was never totally against the idea, because he knew that I was meeting people. But I think I sold it to him as a bit less sexual than what it actually is.”
“So, you kept having full on penetrative sex that first year a secret? Do you feel guilty about it?”
“A bit? Yes.”
I kept glancing to the phone resting on the back of the couch between us. The phone recording everybody between us.
But Caesar held my gaze, ready to proceed. His admission took me aback but he must have felt bold in his anonymity.
“Are you gonna tell him what you did?”
“I don’t think I’m gonna tell him. I think my plan is just to decrease the frequency and then wrap up this phase of life with escorting.
I wish I was more open to him. I was scared of the consequences, that my escorting would compromise our relationship.”
“Why did you keep having penetrative sex then? Was it a necessity to maintain business?”
“It was maybe not entirely for money.”
Caesar’s screening process was seeming more and more particular. He wasn’t saying it in as many words but I believe he had cultivated a process where he was essentially engaging in his usual hook ups and just getting paid for it.
“It’s easier for me to meet someone that I’m at least a little bit attracted to. There are people that have asked me, and then I just declined if I wasn’t interested. You also have the power to choose if you want it.
So if I have to answer, Why did I keep going? I think it’s a bit a mix of both. Definitely, it’s always nice to have extra money. But also, I think I really enjoyed also meeting other people sexually.”
“What’s the journey from a monogamous relationship to open? Did your escorting play any part in that?”
“It kind of started when we were just like going clubbing together and started enjoying doing things with other people.
Opening the relationship made me a bit more comfortable, knowing he was more okay doing things with other people as well.
Even though most of the time, we play together. At least I know now that he wasn’t totally against the idea.”
“So then, is he fully aware of services now that you’ve opened the relationship?”
“No.”
I wanted to like Caesar. I wanted to believe he was a good person. But, there it was. He was still lying three years into his relationship.
He hid behind his guilt as if it absolved him. Sure, feeling guilty showed signs of a conscience but he is still mistreating his partner.
“If I didn’t feel guilty, I wouldn’t think of decreasing the frequency and eventually stop. I feel like, right now I’ve got to a point where my job is good enough, and it gives me enough financial security.
It’s also time that you invest to be an escort – meeting people, chatting with them, try to understand what they want, trying to understand the whole dynamic, and then finding time to meet them. It’s time consuming.
If I have to look at the money, I feel like with my other job, I’m pretty secure. If I have to look at enjoying having sex with other people, I feel like I can still have that with my partner. We’re having a little bit more sex with others than when I started three years ago.”
—
This interview has left me disillusioned. It didn’t make escorting look glamorous, but rather human.
If I learnt anything from my time with Caesar, it is nice people make hurtful decisions too.
My conclusion is that, although Caesar made it seem that I may be able to take up the business, I don’t know if I would be able to allow escorting to wreak its tender havoc on my life.
I came in curious about power, desirability, and the fantasy of being paid to be wanted. I left thinking about loneliness.
Caesar had clients. A partner. A profession that demanded empathy. A body people paid to touch. And still, no one to talk to.
When the mic was off and the air went flat, he told me this was the first real conversation he’d ever had about any of it.
“That was the first time I have had a proper conversation about my escorting. I have no one else to talk to about it.”
I was exposed to the quiet ultimatum – either be frank about escorting and allow it to impact relationships, or run the risk and have secrecy and guilt peck at you from the inside.
—
*A pseudonym used for this interview