by Ruby Ryan
The entire process was agonizingly slower, but one couldn't be too careful in this business. Every veil of privacy was a shield to keep me safe.
My recruiter--who I'd never even met, but who I trusted after two years--had forwarded 15 applicants for this weekend. Busier than normal, but my heart sang to see so many. Each one was a boost to my ego, rich and powerful men who wanted to pay exorbitant amounts of money for my time.
I gazed around the crowded lunch room, picked at my salad, and began examining the applicants.
They were as thorough as job applications, maybe even more so considering some of the questions asked. Employment. Income. Marital status, sexual history, sexual perversions, ethnicity, religion. All the things you couldn't ask on a real job interview. Then the requests for this appointment: length of time, public or private event, then the specific sexual acts expected. In this line of work, it was ideal to get everything laid out up front. Sometimes clients held back on their applications, but I could usually read between the lines. See what they really wanted.
Last week had been a blast. A beautiful silver-haired man who reminded me of Richard Gere, quiet and thoughtful and devastatingly handsome. Someone whose scattering of wrinkles only accentuated his good looks. He took me to dinner before the ballet, where we had tickets in a private box overlooking the stage. By the end of the night I was dying for his touch as much as he was for mine, and then we fucked until our throats were sore from moaning and our bodies too fatigued to move.
I sighed at the memory of my Richard Gere lookalike. Another night like that would be divine.
After two years of this (95 weekends to be exact, but who's counting?) I'd gotten good at spotting red flags. One guy, an executive at some downtown law firm, stressed multiple times in his application that the need for secrecy was paramount--yet listed himself as "single." Yeah fucking right. Declined. Fake names were to be expected, but one guy used a name so ridiculous that I couldn't help but hit the delete button. Sorry, Mr. Bigdick McHugecock. Maybe next weekend.
Two applicants were women. Although I enjoyed the company of women occasionally, that wasn't what I was looking for this weekend. Tonight, I wanted a man. And when you were as sought-after as I was, you could afford to be picky.
And then it was time to look at the perversions. I deleted three men who were looking for BDSM. I'd done bondage two weekends ago, and wanted something more vanilla tonight. Another applicant didn't actually list any sexual requests, and instead used the space to ask me half a dozen questions about my feet: the size and proportion of my toes, whether they were polished, if I would wear a pair of heels he already owned. That one I forwarded back to my recruiter with a "WTF?" note. Don't get me wrong: I'm not one to judge someone for their sexual quirks. Everyone has their thing, and for the most part they can't help what squeezes their lemon. But my recruiter knew I wasn't into feet, and she should have filtered this one out.
That left me with seven remaining applicants.
Now I could be a little more shallow with my selections. It was important to have an immediate connection with the applicants. I wasn't some Vegas hooker who faked it for an hour; I threw myself 100% into whoever I chose. No faking--there had to be a spark. That's what made me so good.
With that in mind, I opened each of the seven remaining head shots and arranged them on my screen. I ate my salad, stared at the men, and listened to my heart.
By the time my salad was gone I'd narrowed it down to three candidates. Three gorgeous men, each of whom I'd be excited to spend the weekend with.
Something vibrated in my pocket--on my work phone. I opened it and cursed: a five minute reminder for a conference call. I'd spent almost an hour in here reviewing applicants.
I quickly closed the TOR browser and disconnected from my burner phone's hotspot, then carried my laptop back to my office.
I listened to the call with only half an ear, which I could get away with since I was only on it as a courtesy. All I could think about were the three remaining candidates, one of whom I'd be spending the weekend with. Their faces and names (face or otherwise) replayed in my head while I stared at the ceiling.
Edgar Degas, an art dealer who probably thought he was clever with his fake name. He had a handsome triangular face and a hooked nose, and a smile that boasted of unspoken secrets. He only needed me for one night: there was an art gallery opening downtown, and he wanted me attached to his arm the entire night. In the notes he mentioned a specific dress he'd commissioned specially for me, a detail which had originally piqued my interest but was beginning to creep me out the more I thought about it. One night only was another drawback. I was in the mood for a weekend affair.
Jamaal Young, a forward for the Boston Celtics in town to play the Bulls. A bench player for the Celtics, a quick search told me. I liked the cockiness of using his real name. Confidence turned me on, especially when they were already attractive. He wanted me to sit court-side during tonight's game, then go clubbing with him after. The team wasn't flying out until Sunday, so it was a two-day engagement. Sexually, he wanted someone to sit on his face. I imagined straddling his muscular body, moving up his chest and then smothering his face with my sex, pinning him to the floor of the hotel room with my curvaceous hips, covering him like it was a full-court press. Mmm, that did sound nice.
Someone asked me a question on the conference call. "That sounds like a good plan to me," I said, then muted the line again. That seemed to placate them.
The last applicant was Miguel Rojas. An investment manager for a company I'd never heard of, which meant they were small. No particular sexual requests, which could have meant he was too embarrassed to list them or could have meant he was relatively vanilla. He wanted me through the entire weekend, all the way until Sunday night, which was the maximum time the form would allow someone to enter.
Oh, and he was gorgeous.
He was Latino, with delicious dark skin and eyes like drops of caramel. His hard jaw was lined with a thin beard, and I could see the muscle in his shoulders and neck. I imagined what the rest of him looked like, and I liked what I pictured.
The lack of other information intrigued me. He was single, and the same age as me: 32. His sexual history was suspiciously low, but as I imagined him gazing at me I believed it. He didn't want anything fancy, no movie premiere or art gallery opening to attend. Just some dirty horizontal dancing.
I was used to being taken out by notable men. I was an accessory to most of them: something that hung onto their arm and smiled in public, with the fucking as an added bonus. I liked that. It made me feel important.
As I'd said, I was good at reading people. It gave me an advantage in advertising, and made me the perfect escort. Reading between the lines, the things they didn't list on their applications. The desires they didn't even know they wanted.
But for the life of me, I couldn't figure out what Miguel wanted.
There were other escorts in Chicago with price tags far below what I charged. Like, literally an order of magnitude lower. If all he wanted was a night of passion, why come to me?
The question intrigued me, and once it had latched onto my brain it wouldn't let go. There was something there, I could tell, but what was it?
My conference call ended, and then I was alone with my thoughts. Friday afternoons were always the toughest with the excitement of the weekend bubbling in my head, but today more than most. I'd narrowed it down between Jamaal and Miguel, but struggled to go from there.
In the end, the mystery was what won.
I switched my laptop back over to the hotspot and connected to my VPN long enough to send the acceptance email out. My recruiter would take it from there: notifying the applicant, requesting payment, then coordinating our meeting place.
A tingle went up my spine the moment the email was away.
"Hey, Cassie," one of the middle managers said as I left for the day. "A bunch of us are getting drinks if you wanted to stop by."
I gave him a pol
ite smile. "I appreciate the invite, but I've got plans."
"No worries--have a great weekend."
I strode toward the elevator with a silly grin on my face.
Oh, I intend to.
2
CASSANDRA
America had weird issues with prostitution.
I mean, I guess I understood it in broad strokes. The stereotypical prostitute was a scrawny homeless woman in a tube top with track marks on her arms and half her teeth missing. Someone who had no other options in life but to have sex for money, and who was beholden to her pimp's demands. Someone who had to sell their body out of desperation, because the system had failed them, and because the alternative was to starve and die.
But I was an educated adult. I had a Master's Degree for crying out loud, and a thriving career. I had options in life. I didn't have to sleep with strangers for money. I chose to, with full informed consent. I got as much out of it as they did, my recruiter ensured all applicants were clean of STDs and had nothing suspicious on their background checks.
I was a high-end escort in the 3rd largest city in America, and I loved it.
What was so bad about that?
I swung by the dry cleaners to pick up my favorite cocktail dress: it was cream-colored and covered with black lace in floral designs, and hung off my arms in a way that accentuated my shoulders. Not only that, but it fit me the way most dresses didn't.
I was curvaceous. Not large, but I had a lot of shape to me. Wide hips and an ass I was proud of, which I kept looking the way it did every week at the gym. An ass that NBA players wanted to be smothered under.
Which meant when I found a dress I loved, I took care of it like it was my pet.
Once I had that I Uber'd home to the high-rise apartment in the Museum district of Chicago. With my dual salaries I could afford something more luxurious, but I loved my little one bedroom in the middle of the city. I hung my dress on the door frame, turned Spotify to a classical piano station, and began my routine.
I loved my little ceremony. A coronation all for me. A long bath with lavender oil, taking the time to condition and then shampoo my hair. Shaving my legs and trimming my pubic hair. Rubbing coconut oil lotion over my arms and legs while my black hair dried naturally, then blow-drying the last bits of wetness away. I was lucky to have gotten my silky hair from my mom, because once it was dried I didn't need to put much in the way of hair products into it to get it just the way I wanted.
Picking underwear took 15 minutes. Most men were visually stimulated; the wrapping paper was just as important as the present itself. Imagining Miguel's tastes, I settled on a lacy red thong and matching bra.
And then I was sliding into my dress, using a nifty hook tool I'd bought on Amazon to reach behind me and pull up the zipper. I had plenty of time, so I tried on four different pairs of heels before settling on the glossy black pumps.
I looked good. I felt good.
I grabbed my heavy clutch and took a deep breath, ready for another adventure of a weekend.
The meeting place selected for us was the lobby bar of the Omni Hotel, one of five locations my recruiter rotated through. The moment I stepped through the door the manager was there, a clean-cut black man with an easy smile but sharp eyes.
"Welcome back, Ms. Kim," he said with a knowing look. "Please let me know if there's anything I can do for you."
I thanked him and continued toward the lobby bar, giving the bartender a nod of acknowledgment. It was always nice to know I had backup in case the meeting went poorly; one signal and either of these men would be there in seconds. It was rare, but did happen occasionally. Again, you could never be too careful. The weight in my clutch was a reminder of that.
I stopped in the middle of the lobby.
He was already waiting, even though I was half an hour early. Miguel Rojas sat in one of the plush chairs facing diagonally away from me. He was dressed in a perfect-fitting suit with the top two buttons of his shirt undone, and one leg was crossed over the other with his hands interlocked over the knee. I felt my breath halt in my lungs; he was even more handsome in person, with skin like smoked wood and a subtle thickness beneath his suit that spoke of unseen muscle. His jawline was hard as his gaze moved across the lobby, searching.
This was the first time someone had ever beaten me here. I wasn't sure what to think about that.
And then he saw me; his eyes locked on like magnets snapping into place, surprise and then realization. They widened almost imperceptibly as he took me in, all of me, toes to my crown.
I always felt a burst of excitement and danger at the beginning, in this very moment where we identified each other. You never knew how it was going to go, like a normal date but with the intensity dialed up to 11. Every night may have been prearranged, but always a unique little adventure.
That's why I did it. Not the huge sums of cash, or being wined and dined and taken to fancy events. I did it for the thrill. The same reason a kleptomaniac stole a stick of gum from the convenience store.
Okay, so it was a little different than that. But still.
I resumed breathing and strode the rest of the way into the lobby bar. My date rose and smoothed out his suit with large hands, and gave a nervous smile.
"Nice to meet you, Miguel," I said, embracing him and giving a polite kiss on the cheek. His cologne was spicy with cloves.
"I... nice to meet you too." He hesitated a moment when I said his name, which meant it was a fake one. Not unusual at all. Especially for someone who looked nervous; the ring of moisture on the table next to him meant he'd come early to get some liquid courage. "How are you, Cassandra?"
Sweat was beaded at his temples, and he gave an awkward smile. The juxtaposition of his boyish nervousness on a body so solid and masculine was adorable.
"You can call me Cassie," I said, taking the seat across from him and giving a warm smile. "And I'm doing wonderful."
I raised a finger to the bartender, who nodded and began making my drink. He knew what I liked.
"You're... gorgeous," Miguel said.
"Thank you," I said, "but I doubt you would be here if I were homely." I gave him a wink to know I was joking.
"No, I mean..." he struggled. "I didn't get to see, ahh..."
I stiffened with realization. "Someone recommended you to me?"
"Yeah. Well. I mean, he told me what you looked like, but words are only..."
This happened sometimes. Someone would apply for their friend, whether for a bachelor party or birthday or any other special occasion. Sometimes a rich father would splurge for his spoiled son on his 18th birthday. As if that was attractive to a woman. Ugh. My recruiter knew to filter those kinds of clients out before they ever got to me.
It usually pissed me off. I wanted my applicants to want me, to have chosen me, overwhelmed by a primal lust as old as mankind itself. I didn't like being set up for what was essentially an expensive blind date.
But I didn't feel that way tonight.
There was a kindness in Miguel's eyes to go with the way he looked at me now; desperate to feast on how I looked in my dress, but too polite to overtly stare. He wanted me; I could feel his desire rolling off him like waves. And I'd chosen him for a reason. I didn't want to back out now, and it had nothing to do with the money.
The bartender appeared with my drink: a caipirinha in a short tumbler with four lime wedges at the bottom. I accepted it with a smile and then he turned to Miguel.
"Uhh," Miguel blinked in surprise. "Yeah, make it two."
I leaned forward with a polite smile. "You don't need to order the same thing as me. Not everyone likes a caipirinha." Sweet and tart like a whiskey sour, I'd never seen anyone outside of America order one.
A funny grin spread across Miguel's face, revealing a row of pristine white teeth. "When I said make it two, I meant for me. I already had one before you got here." He held up a palm. "I swear. You can ask the bartender if you don't believe me."
I arched an eyebrow, but sai
d nothing as the bartender returned with his drink. That was one hell of a coincidence.
"My grandfather used to make them," Miguel said after taking a sip. "Always reminds me of being a boy."
The reason was so close to my own that the air almost left my lungs. I got a hold of myself and leaned forward to touch my glass to his. "To an exciting weekend."
His nervous smile returned as he took another drink.
"Tell me about yourself," I said. "You're an investment manager?"
"Technically yes," he said, gesturing with his glass. "But mostly I'm a cryptocurrency trader now."
"Cryptocurrency? Like, Bitcoin?"
"You mean you don't know?" Miguel cocked his head.
"Why do you say it like that?"
"Well, on account of... you know. The payment..."
I realized what he meant. "Oh, I see the confusion. I don't manage any of the... transactions of the arrangement. That's all handled elsewhere."
"Oh." He seemed disappointed that we didn't have the common topic to discuss, but then his face lit up anyways. "But yeah, I'm a crypto trader. Buying and selling, like a day-trader with stocks. It's not just Bitcoin: there are thousands of other digital currencies out there, and it's an art to pick which ones to hold and which to sell."
"That's fascinating," I said. Small talk always helped clients relax at the beginning. "How long have you been doing that?"
"Oh, five years now. I was an investment manager for a big firm before that, then got into the crypto game hard. When my company wouldn't let me add cryptocurrency to our clients' portfolios I quit my job and started my own small firm. It's done pretty well thanks to the crypto bubble." He bobbed his head. "Pretty well."
He stared off, and I could see the nervousness falling back across his face.
"So what do you want to do this weekend?" I asked, gazing at him across the top of my glass.
"Yeah..." he began. "I don't know."
