My All-Too-Brief Career as a Male Escort

by Steve Heilig, May 1, 2014

Uh-oh; any time Gordon called me it tended to mean trouble brewing. He was a man-about town with “no identifiable means of support” who lived high on multiple hogs. People speculated he was a drug dealer, CIA, private dick, or some combo thereof. But he knew just about everybody in the city and always seemed to be having fun.

What you doin’ Saturday night?” he asked without prelude. “It’s the Black and White Ball, wanna go?”

“You asking me on a date?” I joked back. The Black and White Ball happened every couple of years and was a high-society fundraiser for the Symphony or Opera, I forget which, and featured tons of food, drink, and live music, sometimes by big names. The Grateful Dead had played one in the sixties, but now it tended to be tamer fare. It was expensive and also indeed “black tie” and I had no tux nor ticket.

“Don’t be a smartass. But yeah, I’m asking if you want to be somebody’s date.”

“I don’t do blind dates, man” I replied, which was true. Actually, I didn’t do any kind of dates. Never learned how, much too shy anyway. Any women who came my way tended to be longer term friends first or at least more forthright than I was; sad, pathetic even, but that was me.

“Not even for 500 bucks?” he shot back.

“Oh, well, er, if you put it that way…but I have a feeling there’s a catch. What’s up?”

“I thought you might change your mind. Listen, I doubt I’ve ever told you this and you can’t tell anybody else or you’ll be fertilizer, but I sometimes work for a high-end escort company, and they are short of guys this weekend due to the Black and White and other big bashes happening at once. I think you’d qualify. All you have to do is sign a little contract and they will provide everything, a car, driver, ticket, and the client.”

“Wait a sec – will the client be male or female?”

“Oh now you get picky. Woman. Likely some corporate chick who needs a date is all. They get all kinds. I can’t promise you a good time but if you don’t screw up too bad, you will get paid. But listen, you gotta tell me now so I can call them and get this thing going, time is tight.”

“Er…OK, why not, I’m in.”

“Stay by the phone,” Gordon said, and hung up. Within minutes my phone rang again. The officious voice asked me if I’d be home for an hour, and told me to put on some nice clothes for photos. Within half an hour more my doorbell rings and there was a guy with two cameras around his neck, a Polaroid and a regular one. He shot a few photos of me – looking uncomfortable, no doubt – handed me a manila envelope, and split. Inside was a contract. It had the name of the company, a financial district address, and three pages of legalistic verbiage. I had to specify my suit and shoe size, height, weight, inseam, and more. I was to be home at a the specified hour, wear the clothing they brought me, call the client by whatever name she gave me, attempt no physical contact of any kind and not ask for any personal info from her, and to act “like a gentleman of high breeding, manners, and deportment.” No drugs allowed. Penalty for noncompliance was nonpayment or some vaguely hinted at even worse consequences.

My “date” was to be Julie, who was a banker, and she could “fire” me and call the whole thing off at any point during the evening and I had to vanish. She’d write an evaluation after that would determine my pay and if I’d get called again. And that’s all it said.

I signed the form and called the number on it, and very soon another guy was back at my door, looked the completed form over, said thanks, and was gone.

The next morning the phone rang again, and the same voice said I had been “provisionally” accepted, and to be home Saturday evening at 5:30 PM, ready to change into my evening clothes. When that day came, I took a hot shower and waited. The doorbell rang, and a uniformed driver was there, holding a garment bag and some shoes. “Good evening sir, please change promptly into these clothes and come down to the car,” he said nicely. Back upstairs I unwrapped an Armani tuxedo, with a fancy shirt and shiny shoes to match. I put them all on, attempting to tie the silly bowtie. Out in front, a limo purred, and the driver was standing there, smoking. He looked me over, said “Allow me, sir” and fixed the tie, and let me into the roomy back seat.

We drove downtown to one of the fancier hotels, and he pulled in front, and said, “Just a minute, please” and went inside, leaving the limo idling in the taxi zone. Nobody seemed to care, and in any event, he was soon back. He came around to my door, opened it, and motioned me out. I got out and stood there, feeling silly. A thirty-ish woman was standing there, looking at me. She was what my dad would have called a real looker – tall, long dark hair, elegant black dress and long white coat. I just looked back, trying not to smile too goofily. She glanced at the driver, nodded, and he let her into the other door, came around, and let me back in, too. Apparently I’d passed hurdle #2, and we took off.

“I’m Julie” she said, extending her hand. “Very nice to meet you, I’m Steve,” I said, taking hers for a businesslike shake. But I wasn’t sure if I was allowed to say or ask anything else, so I didn’t. We rode the ten minutes or so down to City Hall in silence, me wondering why such a hot babe needed to use an escort service. We then pulled up into a long line of limos and other cars, crept up to the big red carpet installed on the big stairs, and the driver stopped, let us both out, said he’d be back at midnight, and to enjoy ourselves.

Inside the huge tent they’d set up it was loud and crowded already, with fancy people signing in, seeking drinks, and heading to their assigned tables. We found ours – twelve middle-aged or older white folks, already seated and eating the appetizers. Julie introduced me all around and I promptly forgot all the names, but they all seemed to look me over a bit more than would be considered polite. The conversation was stilted and boring, and I resisted my usual urge to fill the gaps with silly jokes and such.

The main course came and we dug in; man these people were dull. I also resisted the urge to guzzle the fine wine the waiters kept topping off in the big glasses. “How did you two meet?” asked a lady to the right of me; I hesitated just long enough for Julie to say, “Through business,” which was not even a lie. I noticed that one guy kept glaring at me and developed a theory that I was there to make him jealous. But who knew?

As we dug into dessert, a loud announcement was made: “Ladies and gentlemen, for your pleasure, Mr. Tito Puente!” Holy crap, I almost blurted. The Latin jazz and mambo king himself. A living legend. Suddenly I was happy to be there beyond the payout. I twisted to look at the stage and there he was, with his full band, all in shiny uniforms. With no other fanfare he gave his big goofy smile, counted off ‘One two three” and they blasted into a groove. He was no spring chicken and grey of hair, but lit into his timbales like a demon. Long ago, Carlos Santana had taken his hit song “Oye Como Va” to the top of the pop charts, but millions of Latino music aficionados knew him for many other hits and decades as well.

Two more songs, and many of the tables around us had emptied onto the dance floor. My gang of bankers all just sat there. I noted Julie was tapping her high-heeled toes and couldn’t take it anymore, so leaned over and asked, “Care to dance?” “I thought you’d never,” she replied and I got up, pulled out her chair, offered my arm, and off we went to join the fray.

I didn’t know much about dancing, but could fake it well enough. After a couple of awkward moves we found a rhythm and were spinning a bit and having fun. That song ended and the band went into a slow groove. I hesitated and raised my eyebrows, but she grabbed my hand and started to move. We were in a romantic clutch, my hand on her bare back, hers around my neck, swaying and shuffling nicely. I smelled her subtle perfume. It had been a long time. She pressed fairly tightly into me and I felt intoxicated and in danger of arousal. In a weak moment, I said “You know, if circumstances were different I’d – ”

“Shut up and dance,” she cut me off, with a smile. I shut up and danced.

We danced a lot more. The music heated up again and I was drenched in sweat, but so was she. At one point I noticed one of our table-mates nearby, doing that frat-boy wedding-reception drunken boogaloo. I didn’t see Jealous Guy anywhere. At the set’s last song, another slow burner, we were face to face swaying, and I came within an inch of a kiss but caught myself just in time. I wanted that $500 too badly.

There were other bands, and we danced more at other stages, and finally, back at our table, had a glass of fine sherry and rested. Some of the coats and purses were gone from the seats, so some had left. Jealous Guy was nowhere to be found; I thought I saw Julie looking for him. Finally she said “Ready to go?” and I nodded, rose, helped her put her coat on, and we were off.

The driver was outside, as if by magic, so she wouldn’t turn into a pumpkin. He let us in, said, “Have a nice time?” and we both said yes. He drove us back to her hotel, pulled up in front, and stopped, got out and stood outside the car. Julie and I looked at each other, me determined to remain silent and not screw up. She smiled and extended her lovely hand. “Thank you for a lovely time,” she said. “And thank you,” I replied. She held my hand a moment longer, then withdrew it, started to turn to the door, but then suddenly turned back, leaned into me and, as they say in the romance novels, “put her lips to mine.” I felt warmth and and then a tongue and heated breath from her lovely nose. I didn’t know what to do, but then felt her hand on my thigh and kissed her back. I put my hand to her lovely neck and ear. She was a great kisser. Such states being what they are, who knows how long it lasted, but then she leaned back, laughed aloud, opened the door, and was gone.

After walking her to the hotel door, our driver returned. “Home, sir?” he asked. “I guess so,” I replied. He started driving as I sat, a bit stunned, alone in the back. After a minute I sighed and just said “Wow” to myself. The driver caught my eye in the rear view mirror and said, “Yes, sir.”

He let me off at home, I went up and inside and changed out of the clothes and shoes and brought them out to him in a sweaty, stinky wad. “Thank you and good evening,” he said, and when I reached for my wallet to tip him, he said “Not necessary, sir, it’s all been taken care of.” And he was gone.

Inside, I sat down with the cats and pondered. I realized I suddenly felt very lonely. But by the time the registered envelope came through my mail slot the next day, with five $100 bills inside and another one folded into a little sheet of hotel stationary with the handwritten words “Lip tip,” I felt pretty damn good about myself and my new budding career.

But they never called me again.

3 Responses to My All-Too-Brief Career as a Male Escort

  1. mark Reply

    May 6, 2014 at 10:14 pm

    I gather this dates back some years..I think most male escorts nowadays are gay. The 1% women want to have fun, but still belong, in every sense of the word, to the 1% men, and these latter tend to be jealous..viz. Donald Sterling!

    Of course the women do sleep occasionally with these ‘gay’ escorts, I’m told. There must be a fair amount of HIV even among the 1%, I’d conclude.

    Thanks for the tale. We hear often about the exploits of the male 1%, but rarely about what their women are up to!

  2. Robert Liner Reply

    May 3, 2014 at 10:10 am

    Your “all-too-brief career” was a virtual page-turner. I have this complaint:
    the gripping narrative (which, happily, does feature a bit of gripping) resulted in my coffee getting cold. Thank the goddess for the invention of the microwave!
    “Lip tip.” Cute! I can empathize with “Mr. Jealous.” Wonder where she banks.
    Thanks for a fun read.

  3. Jim Armstrong Reply

    May 1, 2014 at 10:21 am

    Thanks, Steve, I enjoyed that.

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>