It would also give me a reason to refuse any further dates for the rest of the week. Eloise would be pissed. I smiled at the thought.
When I reached into her panties with my left hand, she started screaming. I circled her clit slowly, building the pressure, teasing the responses out even as I pushed my fingers inside. I couldn’t tell what she was saying—it didn’t sound like my name, but you never know.
Her legs shuddered, and her body arched off the bed, fingernails digging into my biceps.
While she came down from her orgasm (and damn, she was loud), I pulled off her panties and dropped my briefs, sheathing up quickly. I always preferred to do that myself—long nails or rings with stones could rip the latex.
She still had her pumps on and I was kind of looking forward to feeling them digging into my ass. Even boring sex was better than my left hand.
“Ready for me, baby?”
“Mmhmm!”
I got in position and moved fast, making her cry out. She wanted hard. Her request was granted.
I gave her a moment then circled my hips. She started moaning again so I let her have what she’d asked for, telling her she was hot, describing how she felt, telling her how high she was going to fly, how hard she was going to come. I could practically do it in my sleep. Which was just as well—the jet lag was catching up with me.
I used my fingers to get her there again. It took a while and it was getting almost painful holding off, but that’s what I was paid for. This wasn’t about me and my pleasure. It never was. I made a list mentally of all the chores I had to get done this week: coordinate schedule, go through emails, stock up on oil paint, dry clean suits.
By the time she finally fell off the cliff, I’d moved on to mentally cataloging my DVDs. I let go, too, falling with her.
I stayed inside until I was sure I was getting soft. Pulling out when I was still hard hurt some women, especially if they were post-menopausal. They liked to be sore as a reminder of what they’d done. But not too sore—that was bad for business.
I sat up and threw the used condom in the trash then took a sip of the brandy we’d abandoned.
Her eyes were closed, her mouth open, and her breathing rapid. I checked my watch. Plenty of time. Depending on what she wanted, I’d take the second fuck more slowly.
Her eyes fluttered open so I leaned down to kiss her shoulder, pulled the sheet up to cover her breasts then placed another kiss on her forehead. It was intimacy that she’d want now. I really should write that manual.
“You were amazing, baby,” I said, faking sincerity with ease. “You are so fucking hot.”
She smiled lazily and stretched out. “I could definitely say the same about you, Hallen. I mean, phew!” And she fanned herself.
We had sex once more and she had to admit she was done.
For a second, I lay staring up at the ceiling—another empty, white ceiling. How did I get here?
I kicked away my depressing thoughts and stood up, dressing slowly, looking regretful, leaving her with the illusion. We were both playing a game, but she seemed like a nice woman. It was cool.
I kissed her on the lips once more and left.
As I closed her hotel door behind me, I heard her giggling. Good. Job done.
In the minute that I waited for the elevator, my mind had already turned to other things.
When I arrived home, all I wanted to do was wash the smell of her from my body and crash, but instead I opened my laptop and made a new entry.
Soon after I’d started in the biz, I decided I should use a database. It helped keep track of dates and what they liked. I was paid to make these women feel special, so remembering their preferences as well as their names—which was hard enough—was pretty much essential. Hell, no one wants to hear someone else’s name being yelled out when you come. Sex 101, and page one of my manual.
That was Belinda’s first appointment. I didn’t really care if she scheduled a second.
Even so, I added her to my database while my memory was fresh—just in case.
I opened a bottle of cold beer then began a new entry. I typed in my notes for the evening using two fingers.
Likes Barry Manilow.
God help me.
Do you want to know everything? I promise it’s meaningless. Just a job.
When I’d started, I’d taken every client I could. These days I could afford to be more choosy—unless Eloise was cracking the whip, like tonight. So my database was smaller, more selective.
Stephanie had a thing for anal which I wasn’t keen on but it made her scream—in a good way. I guess her husband wasn’t that interested either. She didn’t say as much, but she didn’t have to. I was a good guesser.
Nel liked what she called ‘a lazy fuck’ where she just lay there while I pleasured her in every way possible, but moaned the most when I massaged her afterward.
She’d also never had an orgasm before we’d met and had promised me that she wasn’t capable of one. She even said that her doctor had confirmed that ‘female sexual dysfunction’ was common in a woman her age. What a clueless prick. I felt sorry for his wife.
I’d also taken it as a personal challenge. It took us until dawn, but we got there in the end. We were both exhausted but I still felt like cheering. I was proud that I’d been able to help her out. She was so grateful, she bought me a $5,000 Rolex. Perks of the job.
When we were fucking, she treated me like her lover, but when it was over, she treated me like another son. It was kind of a mend-bending at times.
Unfortunately, she later developed a taste for strawberry flavored gel which she’d smother all over my dick and then lick it off. I couldn’t get rid of the scent for two whole days after. Put me off strawberries for life.
Nel flew in from Duluth for a shopping trip a couple of times a year. She thought it was hilarious that I was younger than her son.
Yeah, she was really into her ‘mild bondage’ and kept a pair of furry handcuffs in her purse. Seriously.
We’d had some fun with those. She’d got more into it lately. She had me spank her a couple of times but decided she preferred to do it. It was okay. I wasn’t that into it for myself, but, whatever. I got paid. I drew the line at letting her using my belt on me. She wasn’t happy about it. I didn’t much care.
Yvonne just liked a good hard fuck—as many as she could get without killing me. Of all my clients, she was the one who came closest to being insatiable. It was hard to believe she was 52—maybe it was all the yoga she did. Fuck knows, but it took a few days for me to recover after a week with her.
In the small amount of time when we weren’t fucking, she told me that her husband had been impotent since he’d had a prostate operation, and financed her biannual fucks. She had no hang ups about her friends knowing what she did. I’d met several of them. Two had made offers, but that seemed unethical to me.
The only people who weren’t in on the secret were her children. She felt that people in their twenties were more judgmental.
Perhaps that was true. I just wasn’t one of them.
Peggy was one of my favorite clients. She was also one of the few who didn’t want sex, but just a nice dinner where she could enjoy the image of being wined and dined by a beau—her word. She was also the only one who truly enjoyed going to art galleries and one of the few who knew that private side of me.
She liked what she called ‘cultured conversation’, and I learned a lot from her. She treated me like a person, not a piece of meat. Over time, we became friends and I enjoyed our dates, often spending a lot longer than she’d paid for. Maybe I was her pet project, I don’t know. But she was good company.
I liked her.
Another non-sex client. Judy wanted me to accompany her to business events once or twice a year to give the illusion that she was straight, for the benefit of her colleagues, and with a view to being made partner. The events were mind-numbingly tedious but she knew it, and tipped well to keep me interested.
A
t first, she’d been spiky about me touching her—holding her hand, kissing her check—enduring it just for the illusion. When she realized I wasn’t going to try and ‘cure’ her to prove some macho bullshit point, she relaxed and we got along okay.
One evening, after another gut-churningly dull event, we’d bonded over Cookie Dough ice cream and a horrendously embarrassing scene in Baskin Robbins on Northwestern Avenue. She’d been dissing the Oreo Nutty Salted Caramel, and I’d been staunchly defending it, when her girlfriend spotted us and started screaming at her, calling her a cheating switchbitch and other charming names. With a bunch of appalled families watching us, I dragged both women out onto the street, getting badly scratched in the process, and came close to losing an eyeball.
It took me for freakin’ ever to persuade Nancy that my cock hadn’t been anywhere near Judy’s pussy; I think the mutual look of antipathy persuaded her of that more than the words themselves. She apologized somewhat grudgingly and they left together, but I was never able to go back in that Baskin Robbins.
Hazards of the job.
Cindy was a client almost from the get go. She was a tiny, white-haired woman, almost frail to look at, but mentally as tough as old nails. Her grandson, Greg, had drowned in a sailing accident. She said I reminded her of him. We went to afternoon concerts, to see black-and-white Spencer Tracy marathons, and European art house movies. Afterwards, we ate apple pie at Urth Café.
Her son had moved away after Greg’s death and she’d never been close to her ex-daughter-in-law. Along with Peggy, Cindy was the only other client who had become a real friend, and the one who encouraged me in my painting. After two years, I’d refused to take her money and Eloise agreed with that decision.
We met up once or twice a month and occasionally I accompanied her to a formal event at her country club. She introduced me as her nephew.
Bob and Sandra were clients during my first year. If they’d contacted Eloise later on, I’d have turned them down. A lot of guys think it’ll be hot to see their woman getting fucked by a stranger—as a kind of interactive porn—but when it comes down to it, they can’t handle it.
Because it worked out with Bob and Sandra, I’d maybe gotten blasé about working with couples. I soon changed my mind on that when I was sent up to a weekend appointment in Monterey.
Some big fish movie guy scheduled me for his wife’s birthday. But then he tried to kick the crap out of me when he saw me pounding into her. Well, no shit! That’s what he’d paid for. It ended up being a serious fight, and some of their furniture had gotten broken. He kidney punched me while I was still inside her, dragged me off the bed and threw me on the floor. As he was wearing shoes and I wasn’t, I took quite a beating before I was able to fight back, using my fists on that fucker.
After that, I’d told Eloise no couples, but Bob and Sandra were harmless, so I kept going with them.
I’d been their first foray into fantasy, and because they felt comfortable with me, they became regular clients. Sandra once admitted that they’d tried a couple of other guys, but it had never felt ‘right’. So I had a standing appointment once a month to screw Sandra while Bob beat off.
The first time had felt really weird, having him sitting in the corner watching, and it was the closest I ever came to not being able to get it up. I started to give myself a helping hand, but Sandra came to my rescue with an awesome blowjob, and after that it was never a problem again. I felt quite proud the first time we all orgasmed in sync.
They were a nice couple and I always got a sandwich after.
I know what you’re going to ask. I haven’t mentioned the L word: love. It didn’t figure into the equation. It never had. There was no Cinderella moment, no ‘Pretty Woman’ experience, and I never fell in love with a client. Never. I can’t speak for them—my clients. Maybe. I don’t know—I don’t think so. But it wasn’t love—just a combination of loneliness and lust. After all, they never knew me because I never let them see the real me.
Only you.
I scored myself another ice cold beer and opened up the calendar on my computer. My eyes were drawn to the name of my next appointment in three days time: Jennifer.
I’d had her as a client for nine months. She paid for my company when she was new in town and wanted someone to show her around. She’d been adamant that it wasn’t about sex, but she’d changed her mind pretty early on during our first date.
She somehow thought that as an attorney, she’d be … what … immune to natural human desires? She was embarrassed to admit that she was having second thoughts, and was considering taking the party upstairs. That happened a lot.
We were having dinner at the time…
“So, um, Hallen, you know I’m an attorney.”
“Yes. That sounds like interesting work, Jennifer, meeting different clients—the intellectual challenge.”
“Well, yes. It can get pretty stressful at times.”
“I can imagine, especially as you’ve just started this new job, in a new city.”
“Yes, and … well, as a lawyer, I have to maintain high standards of professional conduct at all times.”
I nodded, waiting for the punch line.
“So,” she continued, “if the nature of our arrangement tonight got out, well, it would ruin me. I’m sorry if that sounds judgmental, but it’s true.”
“All that’s happened is that you’ve had dinner with a new friend.”
She looked at me skeptically.
“Jennifer, not only have I signed your non-disclosure agreement, I have a confidentiality clause in my own employer’s contract.”
Which was only slightly disingenuous as Eloise had always insisted that I was self-employed.
She shrugged. “We both know that if I tried to sue you for breach of said contract, I’d still be ruined.”
“For having dinner with me?”
“No, for…”
She left the rest of the sentence unsaid.
“Nobody will hear anything from me.” I didn’t know what else to say to her or how to reassure her.
Well, there was one thing that might help.
“I can promise you that I have no interest in any sort of disclosure—my agent would kill me if she found out,” I said, smiling at her. “Besides, if I went around running my mouth off, I’d have no clients left.”
She took a large gulp of her wine and twisted her fingers around the glass’s stem.
“Do you have many clients?”
“That’s not something I discuss,” I said, calmly. I smiled to show that I wasn’t offended. “But I don’t do this 24/7—in case you were wondering.”
She gave an uncomfortable chuckle. “You’re not a workaholic then?”
“Depends on whether it feels like work. This doesn’t.”
I was lying, of course. It always felt like work, and I knew the boundaries that kept my private life separate. Like my painting—a little part of me that I didn’t care to share.
She took another long drink and I saw the sommelier step toward us to refill her glass. I waved him away and poured the burgundy myself.
“Thank you,” she said, quietly. “I’m not usually … undecided or prone to changing my mind once I’ve made a decision. Ha! Well, I don’t usually drink either. And this is the first time I’ve ever…” she gestured toward me. “The first time I’ve ever done this.”
“You’ve got nothing to be … undecided … about,” I replied. “You’re an attractive, successful woman who can afford what she wants. And if she wants to have company to spend a pleasant evening in a good restaurant, why would anyone care?”
“What if she wants more than good food and a pleasant conversation?”
I leaned forward and looked into her eyes. “The evening doesn’t have to end—if you don’t want it to.”
She took a deep breath and wet her lips.
“So, how does this work?”
Her hand waved, awkwardly swatting the air between us.
“P
erhaps you have a favorite hotel, or I can recommend one. You get us a room, and I spend as much time as you want appreciating the woman in front of me.”
“And … and payment?”
“I’ll text my agent. She has your details.”
Eloise was going to be pissed. She didn’t like working late but she knew there was a better than average possibility of having to be available when I had a new client—occasionally at other times, too. I didn’t like dealing with the money side if I could avoid it. Besides, it’s a fine line between escort work and … well, you know.
Some women got off on making me give them a figure. It made me feel like telling them that if they had to ask, they couldn’t afford me … even though that was bullshit. Between five and seven thousand dollars covered it. Eloise got her percentage.
I could tell that Jennifer was having a problem taking the next step. I tried to remember how that felt. I tried to remember when I stopped selling sex and started selling myself. It was a dangerous door to open, so I slammed it shut, finished my glass of wine in one go, and glanced at my watch.
I guess her internal debate was concluded because she pushed away from the table, telling me to make the call and that she’d be back momentarily. I stood up politely then settled back to send Eloise a message. I got her reply immediately.
** Payment received for one additional hour **
When Jennifer returned, her cheeks were pink and she was smiling nervously.
“So, should I call a cab?”
She’d been a client ever since.
Is this too much? You asked me what a typical week was like.
It turned out she wasn’t quite as adventurous as she’d thought—her biggest leap of faith was in contacting an escort agency in the first place. There was no doubt she was confident in her professional life, but admitting she wanted to pay a stranger for sex, that couldn’t have been easy for her. But it was probably safer than cruising a bar and hoping that any guy she picked up would treat her well. That was a leap of faith, as far as I could see.