“I am a cheap prostitute,” John writes. “You have hired me to satisfy you. I don’t like sex but I am very poor and desperate to make money. However, I am also old and no longer attractive. I need you to teach me how to make the most of my pathetic body and help me find more clients.”
Role reversal fantasies aren’t unusual. I’ve had many guys come in wanting a scene where I’m a sadistic client and they’re the sad hooker. But John’s scene is more detailed than most. We trade emails for nearly a month before finally settling on a date.
His fantasies are almost literary; full descriptions of how I’ll put him in a shop window in the red-light district, forcing him to service client after client, or walking him on a leash through the streets in nothing but lingerie before leaving him on the doorstep of a mental hospital left to become the sexual plaything of the residents. The thing that’s central to each of his fantasies is cross-dressing. He’ll be sporting stockings and panties throughout.
Aside from the usual practical preparations, I always need to consider my own relationship to the scenario. Of course, some scenes are a genuine turn-on, with minimal effort required on my part to be in the moment. Other times, my feelings are more ambivalent, but I find an access point, usually through an affection for the client.
And then there are scenes where I know I’m not going to be sexually aroused at all. Cross-dressing is one of those scenes, and so I know this will take more effort than usual, especially if I’m supposed to get hard enough to fuck him.
After more than a dozen messages, we decide our first date will be a sort of audition. I’m a pimp looking for new girls. He’s an aging hooker, past her prime but unable to leave the business.
My job is to evaluate his money-making potential and then give him some lessons in how to better use what he’s got. If he does a good job, I’ll start to book clients for him.
He arrives exactly on time and I buzz him in. We stand in my tiny sublet bachelor apartment, me staring at him and him staring at the floor. He’s probably in his mid-60s, wearing loose fitting brown corduroys and a forest green cardigan over a crisp white dress shirt. His dark blonde hair is coiffed back and he’s wearing a pair of thick-framed tortoiseshell glasses. He’s got the air of a philosophy professor or maybe a noted mystery writer.
“So,” I say sternly. “You’re here for your evaluation?”
“Yes, Sir,” he says meekly. “I hope you will find something you can work with.”
“Alright then,” I say. “No sense wasting any more time. Strip off and show us what we have to work with.”
He nods silently and begins unbuttoning his cardigan. He hangs it on the back of the chair next to him, then removes his shirt. He stands hesitantly in his undershirt and pants, as if he’s not sure he wants to continue.
I come up behind him, put my hands around his waist and press my lips to his ear.
“Be a good whore and show me everything you’ve got.”
He still seems frozen, so I gruffly tell him to raise his arms above his head then pull his undershirt off. I bend to the floor and unlace his brown brogues. I lift his left foot to take the shoe off and he falters a bit, grabbing my shoulder for support.
He’s not quite as steady on his feet as he seemed, so I’ll need to be careful. I don’t need him falling over and cracking his head open on the desk; that won’t be easy to explain to his wife.
With his shoes off, I return to standing and slowly unbuckle his belt. He lets out a little gasp as his pants drop to the floor. As instructed, he’s wearing his stockings (black stay-ups with a swirling floral trim at the top) and a pair of sheer black lace panties.
I instruct him to step out of his trousers and place them over the chair with the rest of his clothes. Then, still standing behind him, I take the sleep mask out of my pocket and slide it over his eyes, leaving him in total darkness.
I walk back in front of him, standing a few feet away. We remain there, mute, as I watch the seconds silently pass on the clock above the stove. I count three minutes, enough time that he begins to shift slightly.
“Whore!” I bark. He stiffens but says nothing. “Speak when you’re spoke to.”
“Yes, Sir,” he says softly.
“Are you ready for your whore evaluation?”
“And you’re prepared for whatever treatment I offer you?”
I let him stand again in silence for another minute before continuing.
“Alright,” I say. “Your training starts now. If it goes well, tomorrow I’ll take you to the red-light district and we’ll try you out in a window.”
He says nothing, but nods meekly.
“I want you to show me how you would display yourself in a window,” I say. “Show me what you would do to attract customers.”
He stands motionless and I realize he’s not clueing into what I’m trying to get him to do.
“You’re in a window,” I say. “Try to get the attention of the men walking past.”
He shifts his weight onto his right leg, slightly jutting out his hip.
“Good girl,” I say. “Now run your hands over your body.”
He begins to softly caress his torso with his fingertips, trailing them up and down.
“Very good,” I say. “Now play with your nipples.”
“You mean my tits, Sir?” he ventures.
“Yes, play with your tits.”
He continues his subtle blindfolded sex dance, running his hands up and down his body, occasionally shifting his weight from foot to foot. I grab a second chair, placing it behind him with the back facing him. I order him to turn around and place his hands on it.
“Now bend over and show me your ass,” I say sternly.
“You mean my cunt, Sir?”
“Yes, your cunt.”
He bends slightly, his ass now sticking out, and continues to shift his weight from leg to leg, causing his hips to sway.
“Do I look alright Sir?” he asks tentatively. “Do you think anyone will want to buy me?”
“I’m afraid not,” I say. “You’re far too old to be a good whore. So you’ll have to settle for being a cheap whore.”
His body stiffens slightly, with what I assume is pleasure.
“Keep showing us your cunt,” I say. “Sooner or later someone will be willing to buy it.”
Leaving one hand on the chair for support, he pulls his panties down slightly and spreads his ass open, showing me his hole. He’s specified that he wants to be fucked during the session but I doubt the mechanics will allow it.
“Are you ready for your cunt training, whore?” I say gruffly.
“Yes, Sir!” he says, his voice jumping an octave.
“Sadly, Master will not be able to fuck today.”
“No. Unfortunately you’re too old and pathetic, even for me. But we will train you to be better. Today, we will use something else for training.”
I rummage through my sex kit for the tiny emergency dildo I keep on hand for guys who are too tight to get fucked or the odd time I’m so repulsed by a situation I can’t get hard.
I slide a condom over it, grab the bottle of lube and walk up behind him, pressing my crotch into his ass.
I instruct him to open his mouth and place the tip of the dildo inside. He lets out a little groan and begins sucking it.
“Good whore. Get it nice and wet before it goes in your ass.”
“My cunt, Sir.”
“That’s right. Your cunt.”
After letting him nurse on the dildo for a couple of minutes I instruct him to open his mouth and take it out. I squirt a generous dollop of lube onto it, pull down the back of his panties and begin rubbing it against his hole.
I assume it will take a bit of effort to open him up, but it slides in surprisingly easily. With the dildo fully inside, I pull his panties back up to keep it in, letting the elastic snap against his waist.
“Okay whore, stand up and turn around,” I say gently. “Now, this is your last chance to show us what you’ve got. Show those men outside the window how pathetic you are.”
He shuffles awkwardly from foot to foot, the dildo obviously causing some discomfort despite going in so easily.
“Good girl,” I say. “Now keep playing with your tits with one hand and slide the other one into your panties.”
“May I play with my clit, Sir?”
“Yes whore. Play with your clit.”
He begins fumbling with his dick, but it doesn’t seem to be getting hard. Though we’ve gone over the scene in immense detail, we’ve never discussed if he wants to come. Subs tend to save their orgasms for later, so I’m assuming it’s okay to forgo.
He has, however, specified that he wants me to shoot on his chest, which is going to be a bit of a challenge. As much as I have a certain affection for this middle-aged married guy who’s into cross-dressing, there’s nothing about this scene that’s turning me on. It’s going to take some effort to bring myself to orgasm.
I don’t know if he’s so turned on or just frail, but he’s wobbling on his feet. I grasp his shoulder.
“Would you like to sit down, whore?”
“Yes, Sir,” he says softly. “I’m afraid I’m not a very good whore and I can’t stand for very long.”
I pull the back of his panties down and ease the dildo out. Leaving his panties pulled down, I grab a handful of tissue from beside the bed.
“Master used a lot of lube because he didn’t know how tight you were,” I say. “I’m just going to wipe it up so you don’t get it on your panties.”
I wipe his ass a few times, doing my best to get it clean and then place the dildo and the tissues in the kitchen sink. After giving him a second wipe to be sure, I pull his panties up and ease him down onto the chair.
“Alright whore,” I say. “Keep playing with yourself and get Master turned on.”
Being able to sit has made things easier for him and he runs his hands up and down his body more enthusiastically. I continue my talk about him being a good whore and pleasing the men in the window as I pull my dick out and begin to stroke myself.
The ability to detach is a hugely valuable skill for a sex worker. In some cases, it might be as simple as closing your eyes and thinking of something else while you try to get hard. But often, it means continuing to do something that doesn’t turn you on (like maintaining a rambling monologue or fucking someone as shit oozes out of their ass) while imagining you’re doing something else.
I jerk myself off as I flip through my sexual Rolodex. Once I’m hard, I open my eyes and move closer so I’m standing right in front of him.
“Alright whore,” I say. “Keep showing Master what you do and he’s going to come on you to . . . uh . . . seal your whore contract.”
“Oh yes, Master!” he says breathlessly as he continues to fumble with his still-flaccid cock.
I continue to jerk myself off, breathing hard until I’m ready to blow.
“Here it comes, whore!”
I shoot, managing to get a few drops on his chest, with most of it landing on the floor. Almost immediately, he relaxes as if he’s the one who just had an orgasm. I carefully lift his blindfold off and he opens his eyes. He sits, wordless, breathing hard.
Now that the scene is over, my detachment fades and I’m almost desperate to engage. There’s so much I’m curious about: how he discovered he has these desires, whether the scene gave him anything close to what he wanted, about his fantasies of feminization. But I don’t ask. Until now, my detachment has been serving me to get through the scene, but right now it seems like it’s working for him too.
There’s an odd tension in the air as if he’s expecting something else, but he remains silent, staring at the floor. Finally, I ask if he’s okay.
“Oh, yes,” he says.
“Did you need anything else?”
“No.”After another minute, he stands and begins to dress himself, leaving his stockings on under his corduroys. He pulls a roll of bills from his pocket and, after counting each one, he places them on the chair where his clothes had been.
He mumbles a gentle thank you and then silently opens the door of my apartment, steps into the hallway, and closes it behind him.