Escorting Stacy

When a gay male escort receives his first client request from a woman, things are only just starting to get bizarre.

Escorting Stacy

I am standing in the St. Regis hotel lobby and while it is not a particularly hot evening I am sweating profusely. I hate sweating before a job. I casually lift my arm and observe a puddle growing on my ill-fitting boxy dress shirt. I was told to look sharp and tidy, so I threw on some office clothes I’ve had since I sat behind a desk four years ago. They were ugly and outdated even then, but I put them on anyway and now I feel awkward.

Businessmen in expensive Armani suits pass by, chatting on their cell phones and saying things like, “Look, the bottom line is up when the ringers go down so you need to get on top of that.” I feel conspicuous and out of place. A bead of sweat rolls down my back, into my khaki dress pants and right into my ass crack.

Where the fuck IS SHE! She told me to be here at six p.m. sharp and that she would come and get me from the lounge. It is now six-fifteen and not a word from her.

I start to text her on my cheap, pay-as-you-go Nokia phone when it vibrates in my hand: “On our way out. My friend is with me.”

I am not normally so nervous and paranoid, but this job is a bit odd. This is the world of straight sex work and it seems a lot more secretive than dealing with gay men, who can’t be bothered to leave their houses to get laid. It all just seems suspicious and by this point I am half-convinced it is really a covert operation to bust me.

“Owen!” a female voice shouts from across the gilded marble lobby. Several men and women in power suits look my way. “Who’s Owen?” I think, turning with the crowd to see the face that would respond.

Oh wait…I am Owen today. She changed my name, I forgot. I plaster a smile on my face, turn back, and wave.

Everything is moving in slow motion, like a hair commercial with a fan blowing on her as she runway-walks toward me. All the men turn and watch as she passes them, showing off her fitted dress that is just business-y enough because it is black but also just slutty enough because it’s tight, low-cut and her boobs are pushed up and powdered.

“Hey, honey,” she says, leaning in to give me a kiss. She smells of perfume and hair product. Just beyond her head I see her accomplice in tow. He’s big—not fat, but solid big. I suspect at one point he did a lot of heavy lifting and has since taken a desk job, his muscles softened from hard chiseled rocks into round masses. His head is shaved, giving him a tough look, like Mr. Clean in a well-tailored suit. The masculine authority in his walk sends my mind into a tizzy and I begin to think that this is really it; I am getting arrested. I start going over the two phone numbers I tried to memorize before the gig in case I need to call someone from prison. I can’t remember anything beyond the first three digits. My mind is going blank.

I feel my shirt turn damp again as Stacy places her hand on the small of my back.

“This is the guy I told you about—Richard. He will be joining us.” She motions toward Mr. Clean. He slowly moves his meaty hand from out of his suit pocket and I nearly faint as I envision a pair of hard metal cuffs falling out of his paw and wrapping around my boney wrists.

No badge, no cuffs. My body relaxes.

I extend my hand to meet his. I feel his firm grip as his brawny hand envelops mine. He looks into my eyes and gives me a warm smile. I melt even more and am beginning to become one with all the liquid being released through my pores.

All this imagined danger, combined with his beefy hand and his tailored suit—while I may still be getting busted, I am totally turned on. I imagine he’s the crooked undercover cop that really needs to get laid. He gets too close for comfort, then forces me to the ground. We start making out and wrestling on the hard marble floor of the hotel lobby as he tries to cuff me while simultaneously taking off my pants. The male patrons all look on with boners…

Stacy interrupts the moment. I am brought back to reality, still holding his hand. He releases it after a squeeze and another smirk.

“Gentlemen, he is waiting upstairs for us and very excited. Let’s go.”

Richard and I follow Stacy to the elevator. I start to examine her from behind to see if there is anything that looks mildly suspicious: a wire, a holster, a stun gun—I really have no idea what I am looking for. While inspecting the silhouette of the dress, I realize I have seen it before; it’s the dress she bought the day we first met.

Stacy originally contacted me via my online listing, in a short and vague email.

Dear Josh,

I am a female. I have a client who will be staying at the St. Regis in a couple weeks. I am looking for someone to join us to interact with him and possibly another male. Compensation will be very good.

All safe, easy

Gladly answer any questions you may have



Of course I had questions! Was this a joke? Women don’t write to me! What did she mean by join? Was I to put on a show? And of course my biggest question was: Did I have to have sex with her, too? To be perfectly honest, that was the scariest prospect of all.

I had been in the escort business for about a year at this point and had received plenty of interesting requests, from dressing up as a super hero to foot fetish work, but never an invitation to join in a heterosexual fantasy. It seemed like a porn movie, and with all my confidence in the gay escort world, I found this particularly unnerving. I began to think a lot about why a woman would want me knowing that I’m gay; the crossover between worlds just seemed strange. Stacy’s short answers via email did nothing to contain my growing fear; I refused to talk money or specific details to prevent any damning evidence should this indeed be a police sting.

When she finally called me on the phone, I was surprised at the voice on the other end; Stacy was pleasant, sweet and sounded a like a California valley girl. We agreed to meet in person and she said she would compensate me for my time. This added to my paranoia. Pay me just to talk? I guess I couldn’t get into trouble for that.

I decided it was time to consult my escort friends, who informed me that, yes, sometimes a female sex worker will contact gay male escorts for a specific purpose, particularly Dominatrices, who occasionally make their male clientele do things with other men. Stacy had mentioned nothing about being a Dom—just that she had “a client.” After a sleepless night, I went over to my Hungarian porn star/escort friend’s place for one final chat, and to tell him where I put my bail money should he need it.

“Just shut your facehole and go meet her,” he told me. “No one is getting arrested! Now shave my back.”

So, I shut my facehole, shaved his back and went to the meeting.

Stacy and I met at a Prêt a Manger in Union Square. I was sick to my stomach, nervously picking at a wilted cob salad with browning avocado that was hard as a rock. Stacy had told me she was a somewhat petite, light-skinned black woman, but without my glasses on, every person fit that description. From the front of the balcony, I nervously eyed every female who entered the store. I am pretty sure I looked like a creep, as a lot of women gave me nasty glances.

When Stacy finally walked in, I felt my heart leap. I knew for sure it was her, despite the blurry vision. She floated in with a fancy silk scarf trailing behind her like a fashion afterthought, and carried a large pink shopping bag from Agent Provocatour, a luxury lingerie retailer. She had an air of confidence and sophistication about her that the other lunch-goers did not possess. I jumped up and waved like an idiot schoolboy. Thankfully, she was just as enthusiastic, waving back with aplomb. She started her strut up the stairs to meet me.

Stacy’s skin was flawless and glowing. She had done her makeup in a natural style, with a pink lip and a slight cat eye that set off her exotic features. Her dark flowing hair was about shoulder-length with long bangs she would whisk away as they crossed her forehead and covered her eyes. She wore a tight top that showed off her toned arms and her ample, perky breasts. She was very, very attractive. I was a bit surprised.

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Like most people, my idea of what a female escort looked like had been derived from mug shots on the evening news—pictures of women looking like they had been in a fight, hadn’t slept in days or were just plain scared. At the other extreme were the models that popped up during my regular online porn viewings, asking me if I wanted to have a good time. They looked overly made-up, with fake tits, penciled eyebrows, long nails, heavy lipstick and big hair. They seemed unnatural, like blow-up dolls that moved.

That’s the funny thing about being an escort: You’d think you would get over the stereotypes in your head because, after all, YOU are an escort. But, I remain in a constant state of naiveté when meeting new people who share my profession. I feel the same way most people do when they find out what I do, and they say, “YOU are an escort???!!” Yes, I am. I am a normal, well-educated, handsome (so I am told), healthy man with no drug problems, no lack of love in my life and I am fully aware of what I am doing. And yes, Stacy was an escort, just like me.

She leaned in for a kiss on the cheek and I caught a whiff of cotton linen and powder. I love that smell. I pulled her chair out and assisted her as she sat down.

“Well, I see someone has manners! Where are you from?”

“I’m a New Englander, born and raised. My mom taught me well.”

“Very refreshing to meet a fellow New Englander and a gentleman. Thank you for agreeing to meet me.”

“It’s no problem…” There was an awkward silence as she sized me up. I had deliberately worn a tight t-shirt to show off my arms and chest. I had on skinny jeans that accentuated the bulge in my pants. I watched her eyes land there as I stared at her chest.

I broke the silence. “I have to ask you this and I know you don’t have to answer but, ummm…are you going to arrest me? “

“Arrest you?! For what? OMG sweetie, no! Oh, you poor thing, relax. Let me tell you a little bit about myself and what this is all about.” She flipped her hair back and settled into her chair.

Stacy explained how she had come to New York fifteen years ago to work on the business side of the music industry and, as she put it, got a “taste of the good life.” She was taken to fancy parties and told to wear expensive clothes she could not afford. She was very outgoing, attractive, and good at talking to men, and at an industry party, was spotted by a madam who noticed her natural gifts. Like most people approached about going into this line of work, Stacy was initially hesitant about it, but the madam promised her excellent money, control over her clients and that she would never have to do anything she wasn’t comfortable with. The rest was history.

Over time, Stacy developed a knack for a specific kind of domination. It wasn’t the ball-busting, spike heel, lick-my-boot-and-let-me-whip-you kind. It was “intellectual,” as Stacy put it. There was very little sexual interaction in what she did—it was more mental abuse. Verbal humiliation over a candlelight dinner in a public restaurant; making high-powered business executives clean bathrooms; wearing a sexy outfit and standing in front of a masturbating man while teasing him about how small his cock was. You know, things like that.

She retired five years ago and went into finance but held onto a few high-rolling clients who required minimal upkeep but paid extremely well.

The client she wanted me to meet had a fantasy of being forcefully taken by another man. More specifically, in his fantasy, a woman forced him to be with another man. It seemed this client not only thought women were evil, but got off when they made him do things he didn’t want to do—like spend his money on extravagant trips, fancy hotels and jewelry, smoke crack, and, apparently, have sex with other men—not because he wanted to, mind you, but because Stacy told him to. It was a psychological game the client liked to play with Stacy and one she had grown very adept at, which was why he paid her so well. He would relay these fantasies to Stacy casually, when out to dinner with her. It was her job to pick up on them and make them a reality for him, all the while pretending it was her idea.

I would say this seemed strange to me but when you are a sex worker you quickly realize that people have all sorts of fantasies and fetishes. Your job is not to judge them but to help these people turn their dreams into a reality in a safe and controlled environment. What may seem odd to some is perfectly normal to others and if you are open-minded, you can even learn about your own desires in the process. For example, I learned over time that I am personally not into inflicting physical pain, be it hitting, choking, punching, suffocating or “ball torture.” I am not a violent person by nature but when I was given permission by clients, I thought, “Hell, why not see what it’s all about?” No matter how much pleasure the pain caused, how many times a client begged for me to kick him harder, I realized deep down that this wasn’t for me. Water sports, on the other hand—who knew how much fun they would turn out to be!

Stacy had arranged a similar fantasy for her client before, and it hadn’t ended well. It hadn’t even started, really; the non-professional she’d brought on board hadn’t been able to get aroused. It was a big disappointment for the client and for Stacy, who had prided herself on being able to make these things happen for him. This time was going to be different; she really wanted to deliver. The client had upped the stakes, too; it seemed he not only wanted to be ravished by a man; he wanted to service another man at the same time.

“So your client wants to be spit-roasted?” I interrupted, using a slang term often said in the industry. Stacy looked me dead in the eye and said, “Exactly. I came to you because I need a professional like myself. Can you do that, can you perform under those circumstances?”

“If I couldn’t, I wouldn’t be where I am today,” I told her—which, in actuality, was a chain cafe, salad stuck in my teeth, talking to a woman I still suspected was a police officer—but I digress.

“He cannot know you are gay or an escort,” Stacy continued.” I am telling him your name is Owen and you work with me in the office. You have to wear business causal clothing and look as sharp and tidy as possible. Can you do that?’

“Yes.” Clearly, I had lied.

“Good…now there is another twist to this.”

Of course there was.

“You will need to wear three condoms and a mask to hide your identity. In fact, all of you will be wearing masks. It should not take more then a half-hour of your time. Also, and this is important—I will be a very different person.”

“What do you mean ‘different person?’” I was picturing some Wonder Woman type thing where she spun around and suddenly had wild, high hair, a fancy leotard and white boots. However, that is not what she meant.

“I will be the boss.”

“The boss?”

“Yes, the boss. Not of you, don’t worry, but of them.”

“Okay sooo…what does that mean?”

“I will be yelling at them and telling them what I want because I am an evil controlling bitch.”

“No way! That is awesome! Wait…is this guy hot?”

I knew that was a dumb question as soon as it came out of my mouth

“Dear, what do you think?” The answer, clearly, was no. “My friend I am bringing along is handsome, though. He’s mainly bi-curious and identifies as straight but I told him he has to do whatever it takes” to get you ready for action.

I kind of got a semi. I love when men who can’t admit they like guys are actually into guys. But there was no way I was wearing more than one condom, I told her. Latex on Latex equals friction, equals broken condoms. Not a good idea. (The client, who was “crazy about safe sex,” Stacy said, seems to have had misguided notions.)

We talked about a few less savory details and Stacy finally said, “This is great! “I can already tell this is going to work out. Now in terms of compensation—is $800 okay?”

I was so used to gay men trying to broker deals with me to lower my rate that I never thought someone would pay MORE for the half hour. It just seemed weird and suspicious so I paused a moment.

“I don’t want to discuss money,” I said. “If you would like to offer me money after the fantasy is fulfilled you may, but it is not because of the act we engaged in, it is merely for my time.” That was my best lawyer-speak.

“Josh, I’m not a cop, you don’t need to worry.”

“You could be and just saying that, cops can lie.”

“I promise, sweetie. I am not. I have just as much to lose and I would not put you in this situation.” We stared at each other in silence. I picked up my Diet Coke, looked over nervously and said, “Okay… I will do it.”

“Good. Oh, and THIS is what I will be wearing… don’t you love it!?” She revealed the businesswoman’s slutty black dress.

Now here I am, a week later, sweating my ass off in fear at the St. Regis; Meat Hands to my right and Stacy in the slut dress to my left; all three of us in the tiniest elevator I have ever ridden in.

Meat Hands looks even hotter from behind in his suit and I like the idea that he will be getting bossed around. I look down at his round little ass. He glances over at me and reaches into his back pocket. Another bead of sweat slides down my back and I hold my breath, waiting for his badge to be shown.

“These pants are a bit tight for this wallet.” He winks at me.

When we get to the room I am struck by the shear gaudiness of the place. Tacky, gold-framed mirrors, princess canopy beds, lots of heavy fabrics and silks thrown around. It is like Louis the XIV had thrown up in there, then sprinkled in a flat-screen television and an iPod dock.

“He is in the bathroom,” says Stacy. “I have kept him there because he was being bad. Have a seat while I check on him.”

I sit down on the settee by the bed and Richard sits across from me.

“You do this a lot?” he asks.

“I’d rather not say.”

“I see…I’m not gay.”

“Right on, man.” I try my best to sound sincere but really want to say, “Yeah, right, man.”

“I am just helping out Stacy. She’s great and I like making her happy, bro.”

Richard reaches in his suit pocket and pulls out a leather case. My heart sinks for the millionth time as he slowly unfolds the cover to reveal a cell phone.


“Huh?” he replies, utterly confused.

“Look, if you are a cop, I haven’t done anything wrong and I am just here. This is entrapment.”

“Haha, what are you talking about, bro? I’m no cop!”

Stacy comes out of the bathroom.

“Why aren’t you guys naked. Richard, get fucking naked!” She sashays up with a smile on her face, stops in front of him, her chest at his eye level, and smacks him across the face. “Naked. You. NOW!”

She turns to me and winks.

I want to be her.

“I have to go and get the rest of the provisions. When I get back you better be naked and Richard, you do whatever he tells you to do and I don’t want to hear from Owen that you have not been behaving.”

She slams the door behind her.

“Dude, don’t worry,” Richard says. “We are not the police. Stacy told me you were worried, don’t be. This is just some fun.”

My body relaxes and Josh Ryley kicks in. I am in control. Well, okay, Stacy is clearly in control but I am second in command.

My heart beats faster as he undresses. He has a very nice build: big, broad shoulders, large chest, and just a slight beer gut that is still firm and not yet sagging.

I watch the tent in his boxers grow as I peel down my underwear and reveal myself. I stare deep into his eyes, making sure not to lose his glance. I am mind-fucking him, telling him telepathically that I am in control and it is working. He is actually into it, by the look of his rising boxers. As we continue to stare at each other, Stacy returns with a bag she throws on the bed. She then lays into Richard, sternly telling him that she is disappointed that he is not further along in helping me get aroused. She begins to turn up the heat by pushing her breasts up to his chest and telling him in a seductive voice that he needs to do what she says, and she follows that up with several surprising slaps to his face. She then forces Richard to the floor, where he lands facing my crotch. At this point, I can not contain my excitement—a real, live self-identifying straight man is getting forced into servicing me—it’s my own fantasy coming true. I look down at Richard’s shiny bald head inches from me and think, “Thank you, Universe!”

Then, I receive the worst oral pleasure a person can imagine. It is not only poorly executed but painful. Stacy sees my face in agony and kneels down, her face inches from his head and my crotch. She insults Richard’s skills and I half expect her to say, “Let me show you how it’s done” as she opens her mouth wide. I take a deep breath. I have never been with a woman; I am a gold-star gay. When I was Romeo in “Romeo and Juliet” as a child, I had to give Juliet a note to tell her that I did not like her sticking her tongue in my mouth. I have never felt a boob; I wasn’t even breast-fed. I’m terrified of what I believe is about to happen.

But Stacy continues past me, much to my relief, and moves on to Richard.

Just as fast as she went down she stands up again and moves toward the bed. Richard seems to be in a haze of pleasure on his knees, almost drooling as he watches her walk away. She removes two cellophane packages from a plastic bag, throwing them in our direction.

“Okay, so here are your masks.”

Two pairs of Duane Reade brand ladies extra-large support hose, in black. I’d been expecting more of an “Eyes Wide Shut” Stanley Kubric-style mask or some “Point Break” Richard Nixon thing, not panty hose.

“What are we supposed to do with these?”

“Put them over your head, tie up the legs and I will cut the holes for your eyes,” Stacy says matter–of-factly.

She moves in even closer to me. I am nervous and begin to shake a bit as I feel her bust against my naked body. Stacy turns her face to Richard, who is standing there at full mast with his stocking mask in place, looking like a demented bank robber.

“Richard, cover your ears, you idiot!” she spits out, then softens her tone as she turns back to me.

“Okay, so you are doing great. It will be real quick, you do your deed and I will make a big scene about it and then I will take you back into the bathroom and make up an excuse for you being really nervous as you have never done this and are freaking out. I will then put the client back in the bathroom and you can change and are free to go. Sound good?”


“Good, you are doing awesome.” The boss returns. “Richard, that’s enough!” She hits his hands away from his ears.

“I am going to get him now.”

While Stacy is gone, Richard and I stand there looking each other up and down and finally begin to touch one another. I’m so turned on I can barely breathe. We move closer and closer, touching and exploring with our hands. I am so close to him now I can feel his hot breath against my skin.

Suddenly, the bathroom door opens and a terrible smell of burnt hair and chemicals wafts into the room—crystal meth. Gross. I can handle a lot of things, clearly, but the smell of meth makes me a little queasy. When a client is on drugs he becomes unpredictable. I place my trust in Stacy that she knows how to command a man who is high as a kite, because I am naked and have a pair of stockings over my head.

Stacy pauses for a moment and strikes a pose in the door, then takes a few sultry steps out with a leash in tow. The leash is stretched to its max and its charge soon follows. He is tall and lanky, wearing a hotel bathrobe untied, revealing his drooping body, with ladies’ stockings on his head, like us, only with no holes for eyes. He hesitates for a moment. I look at him and wonder what he looks like underneath the mask. How does he normally dress? What is his daily routine? How can he afford all this? I usually get to talk to a client so I can understand him a bit more, which often is what I enjoy the most. I like learning about people, hearing them talk about their lives and their desires. I like that I can make them feel comfortable enough to let go a bit; I like being there to catch them when they do.

However, this is not my client and I am there to do a job and I take my job very seriously, no matter how silly or bizarre it may seem to others. I am not there to be moral. And why should I be? Ultimately, I make people, like this client, happy—so happy they have an orgasm at the end. How many people can say that about what they do every day for work?

“Get your ass bent over that chair, you fucker!” Stacy brings me back to the present.

The client quickly moves toward the chair. I am focusing as hard as I can on staying erect without laughing at the situation—three grown men with stockings on their heads, two with hard-ons, one on a leash and a fully-dressed woman bossing everyone around.

Showtime. Richard and I do what has been requested, one of us on each end, and Stacy suddenly turns on the charm. She begins an orgasmic monologue of cheers and exclamations in between moans of fake ecstasy and pleasure.

“Oh my god, He’s doing it. Richard, he is doing it!, Oh my god, it’s just what I wanted. Oh yeaaaaaaaaah, it’s just what I wanted. You dirty man…”

Then, she jumps up and down while clapping, letting out more exclamations and moans. She has turned into a pornographic, foul-mouthed cheerleader. The cheering and clapping eventually prove to be too much and I crack a smile.

Stacy, the consummate professional, knows when enough is enough. She saunters over and whispers in my ear, “You are amazing, and did your job, let’s go to the bathroom.”

We get into the bathroom and I start to giggle. When Stacy closes the door we both let out a sigh.

“Are you serious! Stacy, that is unbelievable, you are great at this!”

“Oh, honey, you are great! I am really happy, he is super happy, I can tell.” ”

We pause, smiling at each other in what feels like a moment of mutual admiration—a moment that only two people in this line of work can share.

Stacy leaves me to clean up in the bathroom while she takes care of the men in the room. When she returns, she informs me that I went above and beyond what she and the client had expected. They want to compensate me $1,000 for my time. I go deaf for a minute—this is a far cry from my usual $250, above even the $800 that she originally promised. Stacy hands me a stack of bills and says, “Count it and make sure.”

“I trust you.”

“Never trust someone handing you money. Count it, honey.”

There it is: $1,000 for a half-hour of my time. I smile and look at Stacy one last time before we both head to the elevator.

I leave the St. Regis on a high; body shaking, hair messed up, stinking like sex. I did it. I was awesome. Richard was awesome. Stacy was awesome. Even the client was AWESOME. As I round the corner from the hotel feeling like a new man, my phone vibrates with a text from Stacy:

“You are great thank you!”

was great, damn it! I saw another facet of this industry I never would have seen without Stacy’s help; I even got to fulfill some of my own fantasies in the process. The titillation of “will they, won’t they arrest me” brought out a different side of myself I had not known was there. It turns out that a little danger—and watching grown men get bossed around like little boys—gets me going.

As I continue walking, I feel the wad of bills in my pocket and I secretly hope that Stacy will hire me again. I take a deep breath of city air, and then I set off to buy some new clothes.