5 min

When your trick doesn’t pay up (Part 1)

Never take a job without knowing exactly what you’re in for

“His skin looks remarkably tight for his age. There’s also something odd about the angle of his cheekbones that I can’t quite make sense of. I’m not at all an expert on such things, but it looks like they may have been pumped with silicone." Credit: Indiana Joel/Daily Xtra

Communication is obviously a critical part of sex work. Being clear in advance about what your trick wants, what you’re willing to do and how much money is changing hands, is the basis for a smooth transaction.

Some clients can be squeamish to share their desires up front. Other times, they may see whores as sexual psychics who are able to know their needs without ever discussing them. The first time you meet someone, there’s always some guess work involved, no matter how much info you have. And of course, there’s the chance things can go awry, no matter how clear you think the agreement is.

Whatever the situation, the better negotiated your terms are, the greater your chances of a successful session. Sexual surprises can be fun, but they can also turn into messy arguments, dissatisfied clients and a lost chance at repeat business.

I get Roman’s message through one of the regular sites where I advertise. He says he’s looking to meet tonight without any further details. I log in to respond but see he’s already signed off. He has, however, attached his phone number, so I shoot him an text message.

He responds quickly, saying he’s interested and asks what I’m offering. This is always slightly frustrating, since it’s obviously much easier when the client just comes out with what they want. But I assume he might be a little shy, so I respond by coyly suggesting we start with a massage and see where things go.

When I arrive, the door opens to reveal a 50-something guy with bulging arms and a barrel chest. He’s a bit shorter than me, smooth faced with bleached blonde hair in a precisely coiffed semi-pompadour. He’s got that ever so slightly tragic look of a middle-aged man desperate to shave a few years off his appearance, believing youth is the principal barometer of his attractiveness.

I step in and drop my bag by the door. The lights are dim but I can still see around his compact flat. It looks like it was decorated from a catalogue. Everything from the art on the walls to the fake orchids on the windowsill feels wholly impersonal. I wonder if it might be a temporary residence. But a glance at his bookshelf reveals a little too much personality for it to be a furnished rental.

There’s a cheese platter on the coffee table and two glasses of wine. I kick my shoes off, take a seat, and Roman starts asking me the usual set of questions.

“Are you American?” No, Canadian.

“What are you doing in Europe?” Long story. A bit of a work, a bit of school.

“Do you like it here?” It’s growing on me.

He seems genuinely interested, so I spill a bit more than usual, telling him about my art practice, my writing work and the complex series of events that led to my immigration.

Roman tells me he’s a writer as well, apparently a successful one. The apartment doesn’t look like it belongs to someone rich, but not everyone with money spends it on their living space. Still, it’s good to know he’s flush. We hadn’t discussed the time limit, but maybe I can stretch this to two hours.

He talks about his career, the various book tours he goes on. He writes in French, so the majority of his sales are in France and Quebec. He name-drops a few people, but I don’t know anything about the French literary scene, so I just nod and smile. He grabs me a copy of his recent bestseller to thumb through.

I  find him almost obnoxious. But at the same time, there’s something endearing about his self-posturing. It feels a bit like we’re on a first date and he just really wants me to like him.

At this point, I take a closer look at his face in the dim light. He’s definitely older, maybe closer to 60. But his skin looks remarkably tight for his age. There’s also something odd about the angle of his cheekbones that I can’t quite make sense of. I’m not at all an expert on such things, but it looks like they may have been pumped with silicone.

And then there are his lips. Both the top and bottom seem extremely large and swollen, almost as if he’s been punched, and coloured purplish white. It looks like he’s had them surgically altered, injected full of collagen or something.

It might be the result of a recent procedure with swelling that’s supposed to go down. Or perhaps that’s their intended state. Whatever he’s done, they seem way too big for his face at the moment. There’s also a large blister on his top lip. It could be herpes or maybe just chapping. Regardless, I make a mental note to keep his face away from my mucous membranes.

We’ve been chatting nearly 30 minutes and although I had ambitions to stretch the session out, I’m starting to realize how tired I am. At this point, we should probably keep it to an hour, so I suggest we head to the bedroom.

I arrange the towels and pillows on the bed to create a DIY massage table. He puts on a CD, strips to his underwear and lies facedown. I begin rubbing his shoulders to a cover of “Midnight Train to Georgia.”

I run my hands down his muscular body, gradually moving my strokes lower and lower until I’m bent over him cupping his ass. He grabs my legs and begins moving his hands up my thighs as I run my lips along his back. After a few minutes, I climb onto the bed, pull his underwear off, and bury my tongue in his ass. He moans and arches his back to bring his hole towards me. At the same time, I slide my hands under his legs and begin playing with his dick. He’s rock hard and surprisingly big.

Done with his ass, I ease myself off the bed and whisper in his ear to turn over. Normally at this point, I drop my underwear so my dick can hang in the client’s face as I’m massaging their chest, but given the blister, I keep them on for the moment so as not to interrupt the session with a discussion about what’s going on with his lips. He squirms as I tweak his nipples, and reaches up to grab my ass.

There’s no clock in the bedroom, but it’s feeling like we’re close to the finish line. I release myself from his grasp, drop my underwear, climb back onto the bed and intertwine our legs so we’re seated, facing each other with our dicks touching.

I jerk us off while he cups my ass, pulling me closer to him, his balls pressing into mine. Sweating and grinding, we manage a near simultaneous orgasm, shooting all over each other and then pulling each other close, feeling the strands of cum pressing between our chests.

After a few minutes of cuddling, I gently extract myself to go to the bathroom and hose down. It’s meticulously organized with six different bottles of cologne evenly spaced along one shelf and at least twice as many skin care products below. I use a wet facecloth to get the bulk of the nearly-dried semen out of my pubes, but realize that I’ll have to shower at home to clear the rest of it.

I emerge to the living room and find him fully dressed, with a small wrapped present in one hand. It’s a copy of his book, he says, autographed. I smile and tuck it in my bag, while glancing around to see if he’s left the money somewhere . . .