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So You Want to be an Escort

"A man teases his friend about a career as an escort..."

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Today, I was chatting online with a very special friend of mine. We are very close but recently, we have stayed away from fantasizing about each other. Sometimes in life, the friendship takes the greater importance and it is not a bad thing.

We were talking about her career goal. She is in her 40's and back in college after raising her children. As a business major, she was considering the Hospitality Sector: hotels, resorts, etc. I teased her about becoming an escort. "Great job," she replied. Her answer brought us back a few months ago, when we would share our dreams as well as our real life experiences, past and present. I must tell you my friend Janet is exploring the bdsm lifestyle in many ways. I know where she went and I have a very good feeling about where she is going.

I felt I was long overdue about playing with her mind. That is the best online sex possible, playing with the mind; much better than camsex in my opinion. This is how I described her work as an escort, using Skype on my iPhone to tease her from my office.

"Janet, being an escort would be great. Imagine you would be paid to date out of town business men, or maybe women, on occasion. I would have fun buying you dresses and shoes; but the only condition would be that I would chose the styles and the sizes," I started telling her.

She did not reply, but I could well imagine the images in her head. I have a wicked sense of fashion and when I feel like dressing a friend in a sexy way, I can go trashy. Janet has been a very willing model for my nasty urges. I always felt the shoes were so great; it gave her the courage to wear my selection of dresses in public. Receiving pictures of Janet in bars, restaurants or other public places as proof of her obedience was my reward.

"So Janet, can you picture yourself, letting me choose the outfit and the shoes; sending you to get your hair and make-up done?" I asked. Of course, I knew the answer. She had very crisp images of herself in her mind. Janet is a mature woman, a short brunette, plump like I prefer them to be. Her sex-appeal is built into her personality. Her attitude yells: "I want to please you! Do to me what feels good!" Never would she say this openly. But I felt it on our first online encounter; and now it was only more obvious.

"I would select the clients for you dear. Only the finest! I would check their background, ensuring your health and safety. You would have no concern, but would also follow directions without question," I went on. I bet she swallowed hard at that last comment. I knew her current experiences were matching my words. She was now at the stage of following orders; without any hesitation. As an escort, she would do the same.

"Walking in the lobby of a hotel or the entrance of a restaurant, you would attract attention. After dinner is over, you would maybe go dancing or attend a show. After the evening, you would accept the invitation to go up to the hotel room; even if plain sex would not do much for you," I knowingly told her.

"But my research for customers would also serve to identify the best and unique clients; for those, no play in the hotel room.

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True to your nature, you would allow those clients, the ones with a twisted mind, to take you into a darker place. They would be allowed to do things to you that are not usually permitted, even by the highest paid ladies," I whispered to her.

"You would be taken down alleys, into decrepit buildings, places I would have proposed to those customers when arrangements were made. I would remain in the shadows, to guard over you. Once there, your breasts would be grabbed hard, your nipples twisted, your clothes torn off. You would get tied up, mauled, molested. Your body would be probed, spanked, whipped," I told her in a low voice. "You would get your pussy fucked, your ass as well and probably your throat. Once done, a very big tip would be left for you; but that was not your motivation," I finished the description, out of breath.

"Being so close, I would pick you up in no time, your faithful Marc. I can see myself parking in front of an empty warehouse, making a note to myself to have this property torn down, before someone gets hurt," I continued. She knows I own and manage such properties in the city, making this very realistic. "I can see myself riding up the freight elevator and seeing you, Janet, visibly worn out, wrists cuffed and tied with a chain to the wood rafters of the roof. I see bruises showing and I know they will soon turn blue. I am amazed at the red maze of whip marks, criss-crossing the white skin of your body. Cum-matted locks of hair hide part of the lovely face I enjoy watching. Streaks of mascara run down your cheeks." I paused to savor the moment.

"Before untying you, I run my hands on your body, checking for reactions, as if I was mapping out the most hurtful areas. I cannot resist touching the puffy nipples; brushing my hand across your chest and then grabbing your tits forcefully, examining the scratches, letting each mass of flesh drop to your sexy belly," I added, almost dreaming.

"My hand goes between your legs, exploring the distended cunt lips. You are open and wet. I wonder what was used to make you gape this way. I will watch the video from the security cameras later, while you sleep in my bed," I added. "I run a few fingers up the crevice of your ass, up and down, until two of them rest on your rosebud and slowly make their way into your ass. You are wet and loose. The soft moans indicate you are raw and sensitive. I smell the thick coating on my fingers... ginger... Hmm. Only then, after a few blows of my bare hand on your ass, do I untie you, taking you to my car, using my overcoat to shield your quivering body from the light rain," I ended my description.

I looked around, and it felt I was coming out of a wet dream, sitting in my office. She could be heard breathing hard and I realized she had not spoken one word. It was our first dirty chat in months and it felt like a monologue. But a very powerful one.

This was the way I described her career as an escort. I doubt it will be her career, but maybe a side-line.

Story written by Michel Bera.

Published 
Written by flirtingbear
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