Part I
Cheryl
Chapter 1
"It's all about timing, Joe," she grinned at me, her slim hand brushing across my lean muscled torso, crossing my short nest of curly brown pubic hair before arriving at my penis, both hair and penis sticky from the drying effluence of both guy and girl juices. "Time it right, and no one will know."
"That selling off my shares of my brother's company isn't insider trading?" I asked.
"You sell it off before the stock peaks and before your brother sells off your dad's company. And your shares, though substantial, aren't exactly game changing."
"And what do you get out of this?" I asked.
"Besides this?" she giggled, tugging at my penis, beginning to harden again. "You let me handle your portfolio and both of us would be most rewarded."
"Including buying shares in your own company?" I asked.
"You let me worry about that," she said, moving down and engulfing my penis in her mouth.
I think I surprised her, not easily done with her being remarkably wise and clever and mischievous and almost all knowing in her brilliance when I urged her to straddle my face with my last deposit of semen still inside her cunt, even after that first blow job in which I kissed her with another deposit just swallowed by her. I think she found sex with me to be full of surprises, all happy ones. Including me teasing out via cunnilingus a couple most profound orgasms, which made her happy to oblige my urging for the sixty-nine.
And again I proved my skill at sucking cunt, sending her over once more, her mouth needing oxygen to pant and squeal her pleasure, leaving her hand fisting my erect cock.
Sliding from beneath her, her hand almost reluctant to give up her hold, I pulled her into position on her back, bringing her legs high framing her slim, subtly curvy torso, her resilient b cup breasts hardly sagging at all, whereupon I fucked down into her pile driver style, and with a power and quickness not unlike that descriptive term, bringing her more orgasms, arriving quicker and becoming stronger, until I finally pushed deep and remained deep, despite my undulations, while spurting my last ejaculations of the evening.
"Fuck," she muttered. "Finally."
We laughed, hers much quieter than mine having little energy left.
And thus, with my sexual prowess adding on to some long deep conversations, I became the only male member, so to speak, in her company, Mistresses Incorporated, or MSINC as they were officially known. Officially a very successful multi service financial consulting firm.
I first caught Cheryl's eye, or more she caught mine as it turned out, when she entered the grand room, nearly ballroom size, of my family's mansion in Westchester County, New York, the house in which I had grown up when I wasn't off at boarding school. The house had been built by my grandfather whose fortune arose out of prohibition, illicit importing of wine, when it became legal practically cornering the market in importation and distribution of the same substance and harder liquor like Scottish scotch and Russian vodka. My father becoming heir to the business and the house when my grandfather died of emphysema or COD as its now called, and further expanding the company to make it diverse, a conglomerate. When he died fairly young of cancer of the esophagus, also being a devout smoker, about four years before, my brother took over, and proceeded in those four years to ignore our father's dying advice, and watch over a gradual decline in the family business.
Cheryl was eye catching, tall and slim and sexy in her silky, form fitting wrap around dress, a deep reddish blue color that seemed to set off her deep blue eyes, her corn yellow blonde hair piled expertly and yet loosely atop her tall head, nearly six feet tall, the looseness of the style letting strands that seemed to give a halo effect to her model beautiful face. And she could have been a model perhaps at the latter part of her career since her face, particularly her eyes, showed an older presence. If I had to guess, she was basically my age, just past thirty.
When our eyes caught, it was lust at first sight seemingly for both of us. Neither of us shied away from our gazes. And since she'd arrived with my second cousin whom I knew to be gay, as well as quite a bit older, as old as an uncle, I knew they could only be friends.
And I arrived stag, or more correctly came down from my old upstairs bedroom stag having divorced my wife of two years a couple weeks before, my wife having gone off to live with a couple, both bisexual like her, the result of our open marriage, the couple having shared our bed, the husband fucking my wife while I fucked his wife or all four of us joining in with some double penetration of the women, though I had to remind the man more than once I wasn't the least bit gay. Perhaps my wife wished I had been and could watch two men fuck each other amongst the actions of a foursome. Whatever it was, she seemed to prefer their company to mine, and truth be told, though I'd obviously been in love with her once, hence the marriage, our communication aside from in bed had slackened and staggered and stagnated until we barely said hi to each other. In other words it was an amicable and even happy divorce. Even so, I had felt a bit lonely sleeping alone in my king sized bed in my Hollywood condo, and decided to come to the old homestead for a breath of air and to some extent for the party.
The party was a weird sort of gathering, at once a family reunion and business, with having the heads of the various divisions of the family business being invited along with other bigwigs as well and some corporate lawyers, my second cousin being one of the latter as well as being family. He often served as an advisor, even if his law practice was in LA. We'd get together fairly often in LA, usually with his old mother accompanying us. He often talked about his grandfather, my great grandfather, a character who had inspired one of Damon Runyon's colorful New York gangsters. He was the one who told me about my grandfather's original illicit business. He actually lived with his mother and took care of her in the large house near the shore in which he had lived as a teen.
"Joe, this is Cheryl," my second cousin told me, heading directly to me when they arrived. Both of us being tall, me being six feet six inches the tallest in the room, I was easily spotted. "I told her about you, and she's dying to meet you."
The blonde beauty and I exchanged hi's, our gaze continuing.
"Do you mind if I talk to Joe?" Cheryl asked.
"Not at all," my second cousin replied. "I should go so hi to your mom, Joe, and I need to talk with Michael."
Michael, my oldest brother.
Cheryl pressed against me, probably feeling the erection just her vision provoked, and whispered directly into my ear, "Is there somewhere we can be alone?"
"Yes," I replied similarly.
She nibbled my ear before moving away. "Show me your lovely home, Joe?"
"With pleasure," I grinned.
I doubt we fooled anyone about our eventual destination with the pretend tour, but it did let us chat before we arrived in my room. In the backyard with the view of the Hudson Valley we talked about me growing up here and her growing up poor in Minneapolis with just her mother and sister, her father running off.
"You managed to get away from that," I pointed out.
"Modelling," she said. "I was successful enough to go to college. Macalester in Minnesota and then Sarah Lawrence."
"Studying?"
"Business. Finance basically. Started trading while still at Sarah Lawrence and continued after. The trading company that hired me treated me like a hot chick and nothing more. So I found similar victims of low expectations and sexual harassment and we started our own company."
In the library, my favorite room, we continued.
"What are you doing for a living?" she asked while we perused the large selection of books.
"I'm a film editor," I told her. "I've always loved film, and went to USC to study it and to be as far away from here as possible. My dad thought I needed something more practical, basically to join the family business. Originally I was wanting to be a writer, which was worse. Harry, my second cousin and apparently our mutual friend actually helped me land my first job as an editor, an assistant actually with a woman who was favored by some of the more creative of the directors, and eventually I proved myself capable."
"And the writing?" she asked.
I chuckled. "It's good I've manage to make a living at my second choice as you can imagine. I've had a couple scripts bought but not made, but third's the charm. It just got greenlit."
"Congratulations."
"Thanks."
"It's good you kept up your passion despite the struggles."
"I've actually had writing credits," I told her. "Helping out some old USC alums with their scripts. And some script doctoring after that."
