Some folks wake up Monday mornings and say "shit." In my days on the run and in and out of homeless shelters, I did too. That Monday morning I woke up reflecting back on my streak of good luck - connecting with Lisa who introduced me to Jolene who got me into the escort business in which I had completed my first date with high honors from Denise, the client. And here I was, again living in a real (sort of) apartment all my own. Based on the good marks from Denise, I knew there'd be more business coming. And if not, well, come Sunday, I had a date with a woman less than half my age. Yeah, life really was looking up for me.
Mid-morning. I was out riding a 3-speed bike that Marvin, the owner of the bike shop, had let me use. My cell phone rang. It was Maureen. "You need to stop by the office right after lunch, say 2PM. Okay?"
After the fun and money date with Denise, what could I say but "okay?"
I walked into the J & B office a little before two. Jolene's secretary, Maureen, told me I'd have to wait a few minutes and offered me a cup of coffee. After the first couple sips, Maureen said I should go on in to Jolene.
She got right to the point. "Art, your date for tonight is Audrey. She seems to be a Silicon Valley corporate executive of some importance and is in D.C. for meetings. She's staying here in Baltimore at the Four Seasons and you need to meet her in the lobby at 8 PM. Don't be late, she's apparently a real stickler for punctuality. And according to one of our young bucks who escorted her before, she's a stickler for performance as well."
"Performance? How old is she anyway?"
"Don't worry Art, after what we got from Denise, you're up to it. How old? Late 30's, early 40's. She didn't complain about the young buck we sent the last time, but she picked you off our website."
I looked surprised because they'd only made my photo on Saturday - and it was on the website already! Jolene noticed my look and continued with "Look Art, we don't fuck around here. Sorry for the pun, but you know what I mean. This is a business operation and I run a tight ship."
I looked at her expectantly and she continued: "Same drill as last time, you introduce yourself as Ralph and give her the J & B card. Oops, I forgot, you need a last name - let's make it 'Burton.' Okay?" Jolene didn't wait for my answer. I was already used to the way her question-okays were orders, not proposals. "So introduce yourself as Ralph Burton and give her the J & B card. She needs to respond by saying she's Audrey Rogers."
"How am I supposed to recognize Audrey? With Denise, well she was the only middle aged woman in the lobby."
"Audrey has golden blond hair, slender, around five-seven and has dark rimmed glasses. Oh yeah, she'll be wearing a pink dress."
"That ought to narrow it down quite a bit. So I wear my blue blazer outfit again?"
"No, you need a business suit and a briefcase. And Art, don't call her 'Audrey' until she suggests using first names."
I looked at her, probably with my mouth open, so she went on: "Part of her cover and her fantasy is that this is a business meeting that turns social - really social if you know what I mean. Now Maureen will take you shopping for a suit, I have a old spare briefcase you can use."
After the shopping trip with Maureen, my wardrobe had grown by a grey suit, white dress shirt, tie, black shoes and a light grey rain coat. My debt to Jolene had also grown by close to a thousand bucks. I started wondering what kind of clothes I'd be needing for the next sex starved broad. At the rate things were going, I wondered if I'd ever get out of debt.
That evening I took an MTA bus downtown and got off at a stop a couple blocks away from the Four Seasons. I must have looked really good because the doorman tipped his hat and even gave a slight bow. The guy would've shit a brick if he'd known I'd been sleeping in a homeless shelter a couple weeks before!
I was early so after glancing at my watch, I took a seat and kept an eye towards the elevators. On the dot, at eight, a slender blonde woman in a knee-length pink dress stepped out of one of the elevators and strutted into the lobby, jacket over one arm, carrying a briefcase with the other. She was striking but not beautiful - smallish dark eyes, full lips with red lipstick, a mouthful of teeth that would've put Julia Roberts to shame, moderate breasts and wearing heavy dark rimmed glasses.
The introduction went well. Then Audrey took the lead suggesting that we leave our briefcases with the concierge and go to a restaurant that she had picked out.
After we were seated and had ordered drinks, Audrey said that considering the interesting proposal from my company, dinner would be on her. I thanked her and then put my brain in high gear. Carrying on a business conversation was going to take lots of ad libbing on my part. Fortunately my years on the run had worked to train my brain to do just that, albeit not in high finance or business mergers.
"Well, Ms. Rogers, we're in business for profit, but we're fair and realistic too."
"I appreciate that Mr. Burton, but what really interests me is how your board members really feel about this. You know mergers always end up causing lost prestige at some level or other and lots of bitterness."
"Ms. Rogers, my feeling is that the gain in stock price will overcome any damage to the board members egos. All the same, there's a couple board members that I still have to work on. I hope you can give me lots of good arguments."
And so the dinner conversation went, I bullshitted and she probably did too. Just before we got back to the hotel, she said "You understand, Mr. Burton, I didn't want to go into details in the restaurant where someone might overhear. We need to pick up our briefcases from the concierge and go to my room for a private discussion." While picking up the briefcases, we even exchanged some business talk where the staff could hear - we didn't want them to remember us as a horny couple going up to her room to fuck.
Inside her room, or more accurately her suite, she took my suit jacket and got out a bottle of cognac and glasses and we sat down on the sofa. Opening her briefcase, she turned to me and said "Let's get one item of business out of the way. How much for the rest of the night and until morning?"
I told her and she reached in her briefcase. Her pretty hand came out with six hundred-dollar bills, which she stuck in my briefcase.
We sipped the cognac and continued the business discussion charade. Sitting on the couch, her dress had slipped up well above the knees and she looked down at her now exposed legs, then at me, then down again and so forth until I responded by putting a hand on her leg just above the knee. She let out a breath and quivered slightly. Taking that as an invitation, I ran my hand up further and to the inside of her thigh - about halfway from the knee to her crotch. She let out a quick loud breath, looked at me and parted her lips. We kissed passionately and when I broke off for air, she whispered in my ear that I should call her 'Audrey'.
I told her to call me 'Ralph' and resumed the kissing and moved my hand up further to touch her panties, through which I could feel her pubic hair and dampness. I felt her hand on my thigh and then heard her "Oh!" as she jerked upon finding my erection. Moving my hand up to the waist of her panties, I slid a couple fingers inside the elastic and stroked her abdomen. Then up higher to rub her tummy. Remembering that she did have tits, it was time to pay them some attention so I stroked her breasts through her dress.
"Unzip me Ralph!"
This I did and unsnapped her bra to boot and there for me to enjoy were her pert firm tits with dull red areolas the size of silver dollars. I kissed the nipples and let my hand back down to her crotch, this time direct inside her panties and ran my fingers over her pubic hair. She responded with a moan and a quiver. Then I was in her now-very-moist slit. Audrey already had a hand inside my boxer shorts and was touching the base of my dick.
Whispering huskily, "Ralph, as future business partners, we've got to be more open with each other." Audrey shifted her body, leaned forward and pulled her dress off over her head. Now clad only in her panties she took off my tie, shirt, undershirt and then shoes and stockings. My hard-on was raging so furiously that I started thinking I might cum in my pants.