I’ve got the envelope. I’m just not sure what to put inside. I don’t have any paper, other than some crumpled receipts and an old internet bill. Is it okay if it’s empty? No, it’s supposed to feel like there’s a lot of material in there, important documents he’s been waiting for. I have an old newspaper, but that won’t really work — too bulky.
Finally, I spot a half-read issue of The New Yorker on the coffee table. That should do.
I’ve sorted out my props, but I don’t need to bother with a costume. I’m just supposed to be a courier. My usual jeans and hoodie combo will suffice. Besides sorting out this one item, the scene is pretty basic. I arrive with a package for him, he chastises me for being late, and then somehow or other he coerces me into sex.
It takes a lot longer to get to his place than I’d thought, a combination of the subway running slowly and me walking three blocks in the wrong direction, before realizing where his building is.
“Yes?” his voice crackles when I finally buzz his apartment.
“I’m sorry I’m late, sir,” I say, feigning slight fear. “I’m here with your package.”
He opens the door without saying anything and I take the elevator up to his floor. He must be watching through the peephole because the door opens just as I’m about to knock.
He stands there looking stern in his white terry-cloth robe, his dark hair slicked so tightly it looks like it’s painted onto his head.
“I’m sorry I’m so late,” I blurt out again. “I’ve just had a lot of deliveries today and this is my last one.”
“Well, you’ve really kept me waiting,” he says angrily. “I’m going to have to call your boss and file a complaint.”
“Oh please sir, don’t do that,” I stammer. “If I get one more complaint this month about a late delivery, I’m going to get fired.”
I briefly contemplating adding something about my girlfriend being pregnant, but decide to save that for later if needed.
“All right,” he says, sternly. “Well you’ve made me very late to meet friends for dinner. But come in and we’ll see what we can do.”
I step inside his apartment and he closes the door behind me. We stand in the foyer, staring at each other. I tend to plan role-play by email so that there’s plenty of space to discuss dialogue, pacing, and character motivation. But he only wanted to talk by text, limiting the details.
At this point, we’ve basically run through the whole scene as we’d planned it. I have no idea what’s supposed to happen next.
Should I keep begging him not to call my boss? Do we just transition to sex?
“Well?” he says, expectantly.
“Did you . . . want something?”
He rolls his eyes.
“The package you were supposed to bring,” he says.
“Oh, right.”
I pull the manila envelope out of my bag and hand it to him. He glances briefly at it, and then drops it unceremoniously on the floor.
“So . . . is there anything else?” I say.
“I don’t know,” he says. “Is there?”
A flicker of motion from down the hall catches my eye. A naked guy walks out one doorway and into the adjacent one. He’s tall and thin with close-cropped dark hair, but I can’t see his face.
My body stiffens. Our plan wasn’t really concrete, but one thing that definitely wasn’t part of it was a third person.
“Well,” he says. “If this is your last delivery of the day, maybe you can come in for a bit.”
“Uh . . . ”
As a male sex worker, violence isn’t usually something you have to fear. Occasionally you get a weird vibe, but it’s rare for a trick to get aggressive — and almost unheard of for them to do it in their own home. Since you know where they live, it would be pretty stupid to fuck with you; you could return later to settle the score, potentially with a friend or two in tow. That said, when you turn up expecting one person and it turns out there are two, it’s naturally going to put you on edge.
“Why don’t you come in for a bit?” he says, his tone softening. I nod silently, and walk down the hall with him following behind.
When we arrive at the open door of his bedroom I see that there are in fact two additional people; the taller guy I’d already seen and a shorter guy with a stocky bear build and a shaved head.
They’re lying on a king-size bed which almost completely fills the room, sucking each other off, bathed in a soft pink glow from a lamp on the side table. A small cluster of framed photos hang above the headboard, presumably of family members.
So what exactly is happening here? Do these guys know I’m an escort? Or are they supposed to believe I’m a legit delivery guy, about to turn their ménage à trois into a ménage à quatre? If they’re surprised by my presence, they don’t show it or even acknowledge it. My host comes up behind me, places his hands on my shoulders, and whispers in my ear.
“Why don’t you join in?”
At this point, I can’t tell whether the role-play is still supposed to be going on or if we’ve abandoned the premise. If we’ve already given up on it, I’m not really sure what the point was. Surely, it would be more exciting for his guests if they thought I was actually an unsuspecting fourth party, lured into their erotic web.
The two guys start kissing. My host lies on the opposite side of the bed, his bathrobe falling open, and starts stroking his cock, which is already hard. His guests seem sufficiently occupied by each other, so I decide to focus my attention on him. I strip down to my underwear, walk around the bed, climb on top of him and take his cock in my mouth.
“That’s a good boy,” he says, sternly. “Show me how sorry you are for delivering that package late.”
So the role-play is continuing? I glance over at the guys next to us but they’re still seemingly oblivious to my presence.
A few different things could be going on. It could be that he invited them over for a threesome, but then mentioned something about a package being delivered, hoping I could be squeezed into their fantasy part way through. He could have also included them in the idea of the role-play from the beginning. Or, he might be playing out both scenes at the same time: surprising his guests with the presence of an escort and surprising his escort with some uninvited guests.
Whatever he’s organized here, it’s not really okay. Surprising a sex partner with additional parties is pushing at the limits of consent. Tricks often think of sex workers not as human beings with complex emotional workings, but as fuck machines up for anything and everything they can throw at us. While it’s true we’re probably more sexually adventurous than the average person on the street, that doesn’t mean we’ll automatically accept anything you propose.
In this case, since the guys seem not only unfazed by my presence by totally uninterested in it, I feel like I can let it slide. Whatever the scene is supposed to be, for the moment, it doesn’t actually seem like I’m going to be expected to do anything I don’t want to do.
I keep sucking him while I run my fingers up and down his body. He puts his hand on the back of my head, and pushes me down on his cock, so it hits the back of my throat, causing me to gag.
“That’s a good boy. Suck that cock and I won’t complain.”
I hear a little gasp from one of the guys next to us. I glance over and see that the tall guy has just shot his load, cum dripping through his fingers.
Abruptly, he stands and walks out of the room. The shorter guy turns to us, and my host gives me a slight push, indicating, I’m assuming, that I should divert my attention to the guest. I release my host’s cock from my mouth and manoeuvre myself on my hands and knees to the other guy. We kneel facing each other, and he grabs my cock through my underwear, which at this point is totally soft.
The strange nature of the scene has meant that, whatever sexual kick I might get out of it, has been overwhelmed by my over-processing of the experience. We kiss and I gently push his hand away as I start stroking myself, trying to get hard to make it seem like I’m actually into what’s going on.
Through the corner of my eye, I see my host, continuing to jerk himself off. I don’t know if the scene is what he was expecting. But unlike me, he’s rock hard so he must be getting something out of it.
As the guest and I continue to kiss, the tall guy walks back into the room and wordlessly starts to dress. I catch his eye and he flashes a slight smile before he exits again. Seconds later, I hear the front door open and close. We’re back to a ménage à trois.
At this point, I’m finally hard, so I grab his hand, and guide it back to my dick. He grabs it, a little too aggressively, and starts stroking me, while his other hand runs up and down my back.
He stops kissing me and turns to lie on the bed with his face below my crotch, taking my cock in his mouth. I glance over at my host, who’s still staring at us, stroking himself. Although it’s not what I expected, there’s nothing threatening about the situation. What’s tripping me up though is the fact that I don’t know what role, if any, I’m supposed to be performing.
In any role-play scenario — in any sex work scenario for that matter — you need to know your client’s expectations if you’re going to be able to fulfil them. It might be that you just hit the target by accident. But generally, you want to know what’s going on so you can do a good job and, hopefully, be invited back.
Though I’m totally confused by the scene, whatever it is that’s happening seems to be working for my host as he’s still hard. I lie down beside my current guy and take his dick in my mouth while he continues to suck me.
I start to play with his ass, rubbing a little spit into his hole, trying to open him up. That seems to be enough for him, and he pulls out of my mouth and starts jerking himself vigorously, before shooting in his hand with a deep moan.
He abruptly sits up, steps off the bed and exits the bedroom. I glance back at my host and he gives a little nod, indicating I should come back to him. I crawl back across the huge bed and return to sucking him off.
Just as the previous guest, the short guy re-enters, dresses silently, and then departs. Did he instruct them that this was what they were supposed to do? Is this actually a multi-party roleplay? Did one of them arrive pretending to be a plumber and the other one to install the internet?
I continue bobbing my head up and down on my host, fumbling with myself slightly, but knowing I’ve passed the point where I’m going to get hard.
“Yeah boy,” my host mutters. “Suck that dick so you don’t get fired.”
I don’t know what to do with what’s left of this role-play. I just keep sucking him while he mutters about whether or not I might get fired. After about five minutes, he shoots in my mouth. I sit back on the bed, thinking we might have a little post role-play check in, but he just lies there with his eyes closed.
Finally, I stand up and, following in the footsteps of the other participants, I walk to the washroom. There’s no need to shower, but I rinse my mouth out and splash my face with some water. Now what? Should I just leave like the previous two guys? Will he want to talk about the scene? Did I do what he wanted? And what was going on with the extra players?
When I return to the bedroom, he’s lying in the same place, his eyes still closed. I dress silently and then, remembering I still need to be paid, gently clear my throat. His eyes pop open and he turns his head to me.
“So,” I say. “Is there anything else?”
“No,” he says, dryly. “That’s fine.”
“Okay,” I say. “So we just need to take care of business and I can head out.”
“What?”
“I just need to get the money, and then I can go.”
“Oh,” he says. “Right.”
He stands, closing his bathrobe, and walks past me down the hall to the kitchen. I follow him and, after rifling through a drawer, he pulls out a stack of bills and hands it to me. As I turn to open the door, he grabs my arm gently.
“Hey,” he says, gesturing to the envelope containing my half-read issue of The New Yorker on the floor. “Don’t forget your package.”
We both smile and, for the first moment since I arrived, I feel a slight affection from him.
His detached demeanour up until now isn’t only a kind of performance. It’s because he doesn’t expect us to like each other. He doesn’t want a sexual experience where I pretend to be attracted to him. He wants to experience my discomfort and feel like he has the power to force me to do things that I don’t really want to do.
People use role-play to heighten sexual excitement. But they also use it just as often to detach from sex. Through role-play, putting things in a context of coercion allows us to separate out the normal emotions that come with sex.
Part of me wants to talk about what we’ve just experienced together, to help him process whatever it is that he’s going through. But that’s not what he wants. I’m not here to show him that the world could be different than he imagines it. I’m here to show him that it’s the way it is.
I just pat him on the shoulder, pick up the envelope and step out into the hall, closing the door behind me.
Why you can trust Xtra
