"Thanks again - I'll look forward to next time!" Laila gave me a last passionate kiss and headed back to her room. I watched her bounce - it's the only word that fits - out of the hotel coffee shop as she made her way to the elevator bank and I chuckled to myself. I was now richer by $4000 in cash and poorer by four ejaculations - three deep inside her wonderfully tight pussy and one down her throat. It had been a great night - I'd been her "date" to a corporate cocktail party/dinner, and then basically her sex toy for the night. She was a married corporate exec who had a "nice but boring" husband, traveled a lot to the Denver area for work, and had no good outlet for her powerful sexuality.
It was the third time she'd been here - Denver was a monthly stop for her - and she was becoming a regular client. It was a pretty typical gig for me these days. I'd get a text from someone asking if they could set up a massage appointment. We'd figure out the day, time, and where they'd be staying, and I'd show up, usually meeting them at the bar of the hotel they were staying in. They were all high-level businesswomen, often "-C" level, or doctors, or lawyers, government people, etc. Almost all of them were traveling, and most of them, if not almost all, were married. And without exception, they were all very good looking, with some I'd call drop dead beautiful
As great a night it had been, it was, dare I say, somewhat typical at this point. I'd started a couple of years ago, and one thing had led to another, to the point I was making more going out with women than I was as a teacher. Life, as they say, can be funny. Who knew this would happen? Certainly not me - I'd been the guest or 'date' of women ranging from corporate executives to doctors and lawyers to politicians. I averaged three clients a week, most of them now overnights, for which they'd hand me an envelope with 30 $100 bills in it; occasionally more. There were a few women who were able to retain me as a "consultant," which meant I'd see a direct deposit show up in my bank account along with a 1099 form at the end of the year.
So how'd I get started? (I have to laugh as I write that - who'd believe it? And yet, here I am.)
Well, every so often I'd put an ad on the web offering sensual/erotic massage. I think I'm a reasonably attractive guy - I'm 47, about 6'1", 185 lbs., in pretty good shape, divorced, etc. Full head of gray/silver (take your pick!) hair, with glasses, educated, and active. I'd had a range of careers; and was currently teaching high school, having been in the military (three different times), in high tech, been a lawyer, etc. So I was never shy about posting a picture with my ad, which helped. Never one that was too obviously me, but I'd send one on request to someone I thought was real.
I'd met a few women off of the ad, and we'd communicate, usually meet for a drink, and then move back to usually my house for a 'massage.' For anyone who doesn't know, offering a 'sensual massage' is code for sex.
I'd posted the ad again toward the end of the school year, and got the usual range of responses - lots of obvious spam, a few from real people. Typically at least a couple of the real people would actually meet; if we got that far there were very few who declined come over. After the usual filtering of the spam responses, I saw that a woman named Diane had emailed me, asking if I was open on a Wednesday to massage her at her hotel - she was traveling on business. Of course I replied that I was indeed - would she like to meet at the bar? She thought that a very good idea, so we agreed to meet at 9 at the hotel bar.
I went through my usual pre-date/massage routine - big dinner, shower, shave, teeth, etc. And checked my massage bag - a small backpack from my Army days, where I kept massage oils, a couple of towels, condoms, a couple of feathers, toothbrush and toothpaste, and some small electric candles. Cheesy? Maybe. But women seemed to like that I thought of it. And I was off to Diane's hotel.
Her hotel was one of the big ones in the nearby tech center, well known and usually full of corporate folks during the week. Always very clean, and reasonably tastefully decorated for the 'high-end executive" hotel it promoted itself as. I'd been to the bar before - this wasn't my first rodeo at this hotel - so I parked and found my way to the bar, picking a bar table that was a bit darker than the others.
I looked at my phone, and had a new email: "Hi! I'm on the way down now."
"Great! I'm at one of the cocktail tables by the end of the bar. See you in a minute," I typed back.
A moment later, I saw her walk in - and I think a lot of the other men in the bar did too. Diane is on the taller side - probably 5'8", maybe 5'9". Shoulder length dark hair, and a beautifully proportioned figure - no one part dominated. Athletic looking, without that starving-runner physique. And a face that I thought was just stunning. She was wearing what looked like a black miniskirt with a floral print blouse, both snug enough to let everyone see her figure.
I stood up and waved - she saw me and flashed a bright smile as she headed over. I walked around the table to greet her with a hug.
"Hi Diane! Nice to meet you," I said as we hugged briefly - the 'corporate approved' version.
"And nice to meet you," she replied, smiling. "I've been looking forward to it."
"Me as well. What would you like to drink?" Conveniently, a cocktail waitress arrived and Diane asked for a cosmopolitan.
We sat down, and her drink appeared promptly - almost instantly.
"And how the heck are you? Long day?"
She smiled. "Pretty good, but it's been a long couple of days." She took a good sip of her drink and considered it thoughtfully. "That's pretty good." She waved down the waitress and asked for another.
We went through some typical small talk, and she finished her second drink as I finished mine. I learned that she was 49, married with two kids, one in college and one about to go, had been with her current IT company for 7 years, a variety of progressive jobs in other companies before, etc. I got the impression she was something of a "fixer" for whatever company she was at.
She laughed when I said that. "Something like that - I always get sent whenever there's a problem and the CEO needs someone they know to go find and fix it. I'll give you my card later."
I nodded. "I did the same kind of thing when I was a lawyer."
That got her attention. "You used to be a lawyer, and now teach? How did that happen?"
"Choice. I was practicing when I got activated by the Army and sent to Iraq. And realized how pointless lawyering was, aside from the money. So now I teach high school. Much more rewarding."
