The divorce was hard on me. We'd been married seventeen years and she left for Florida to "find herself." I did get to keep the house. In the course of my work I met a woman named Sherry. She owned a small chain of nursing homes across a two state area. We started slow and didn't even make love until after many months. She was a real beauty. She had long black, raven hair and a white porcelain complexion that really turned me on. She was the smartest woman I had ever met. I have to be honest and say I took it slow with her because I did not think she would be interested in me. I'm not that bad for my age but I was slightly intimidated at such a high-powered executive.
During the course of our time together we talked about our sexual fantasies. Hers was to be completely dominated. We tried a few role-plays and I tied her up occasionally, blindfolded her and disciplined her but I knew she wanted more. I made arrangements for her to come to my house on the evening of her fiftieth birthday. I fixed a light dinner and opened an exquisite bottle of wine. Then I led her to the bathroom and drew her a bath full of bubble bath and brought her a flute of champagne. I waited for her in the bedroom. She later came in wearing my bathrobe.
I had several boxes on the bed for her. She began opening them like a little child while she sipped more champagne. I had purchased a velvet French maid's costume with a white skirt and white headpiece. I watched her dress. She put on the garter belt, white net stockings, black panties and the maid's dress. In the last box there was a pair of high heel boots. She left to go finish and I told her to come back looking like a whore. Shortly she returned.
Sherry is a beautiful woman with flawless white skin and a perfectly shaped mouth and piercing blue eyes. She had put on a heavy layer of silver blue eye make up, had lined everything in mascara and had a glossy, thick lipstick. I told her I had the final touch and lifted my hand. I had a Marilyn Monroe blonde wig for her. She grabbed it and went to put it on. When she returned, she did a pirouette so I could have a 360-degree view. I have to tell you that I had never seen a sexier woman in all of my life.
I stood, took her hand and led her down to the first floor, then walked toward the kitchen and took her down the back steps to the basement. When we got to the door I shoved her against the wall with her shoulders and was inches from her face. "Tonight, you are going to be dominated totally. Don't you do one thing without my instructions. You are going to be displayed, punished and discipline like the sub you are." Her eyes went wide with shock. I pulled her into the den.
I had the poker table set up and three of my friends who did not know her were sitting there at the table. When we walked in it was their turn to be astonished. I brought her over to them and introduced her as Desiree, our escort for the evening. I told them we each had to put $500 for her fee for two hours. I put my cash in her hand and they did likewise. Her eyes got wider. I took off my jacket and told her to go make us some drinks after she took our orders.
I sat in one of the easy chairs around the fireplace and the others joined me. All eyes were on Sherry. She has long legs and the stockings looked really good on her. The skirt was quite short and every time she moved it provided a glimpse of her ass. Everyone was mesmerized. She brought a pitcher of martinis and a tray with five glasses. She poured everyone a glass, including herself and she sat down on the arm of my chair. I offered the toast. "Whomever has the most cash at the end of the game gets to fuck this lovely sub." We all touched glasses. We downed the drinks and she poured a second round. Then we moved to the table.
We were going to play draw poker with each of us putting two hundred and fifty dollars in the bank. Whoever won the most of the thousand dollars would get to fuck her, but they had to do it in the room with us. We started the game. I sensed her beside me and she topped off my glass. She walked around the next guy. I saw his hand move up her leg to her ass and give it a squeeze. She pulled away. She walked around to the next guy and he grabbed her ass on the outside of her skirt. Again she pulled away. The last guy pulled back from the table and told her he dropped a chip under the table and to get it for him. She knelt down with her ass sticking up and he smacked her leaving a pink handprint on her ass.
He held the hundred-dollar chip beside his cock which he had taken out of his slacks. She took the chip and began licking him. Then her lips circled it and she moved up and down on it. She laughed. "I don't want you coming too early, big guy, you might win." Rather than coming out from under the table she moved forward and took another hundred-dollar chip and she worked her way around the table giving everyone a blowjob.