Chicago

chicago

by Cindy V.

I had my first experience with a professional role play mistress this week. I was in Chicago on business, opened the weekly newspaper “The Reader” for the adult services section, and chose one of the advertisements. The price was $125 per hour or $225 for two hours, and the location was a fifteen minute cab ride from downtown, in a third floor private apartment above a retail business.

A gorgeous late twenties woman named Mistress Rae met me at the door, took me into one of the several rooms, and interviewed me for my preferences. I looked at Mistress. She had short brown hair, but styled very femininely. She had clear, piercing hazel eyes that she later described as her best quality. She wore a leather minidress that hinted at her cleavage and showed plenty of her shapely legs. She wore shiny shoes with what must be five inch heels. She was very nicely made up, with well groomed eyebrows, thin eyeliner both above and below the eye in a line that was perfectly drawn, and a subtle shade of lipstick halfway between pink and red. Her nails were done in a serious shade of reddish brown.

With much embarrassment I explained that I wanted to be cross- dressed, but with some emphasis on being dressed against my will rather than simply dressed per se. I was into being a woman’s slave and kissing her feet and wherever else it was appropriate to kiss. She asked if I wanted light or heavy domination, a little bondage, and a little spanking, and I answered yes to all of that. She gave me the safewords “Yellow” to slow down and “Red” to stop. She explained that I would be naked and she would not, and there would be no sex. And with that she told me to strip, and she left the room for awhile. So I stripped naked, and sat on a comfortable chair to wait for her.

A few minutes later she flew into the room and started screaming at me. “Who told you you could sit in my chair? You’re getting your disgusting odors and fluids on my special chair!” Of course I knew she was acting, but she certainly seemed serious and in truth I was quite nervous.

She sat down and made me stand right in front of her. She made me turn around slowly for her, so she could examine me. Then she took a ping pong paddle and used it to lift up my cock for her inspec- tion. At that point I was absolutely soft. “That’s a sorry excuse for a cock,” she sneered at me. Then one of the other mistresses came in the room, to get some equipment. My mistress said to her, “Take a look at this puny cock. Isn’t it pitiful?” And without missing a beat, the other mistress replied, “You’d need a magnifying glass to see it.” And my mistress came back with, “Since it looks more like a cunt, maybe we ought to dress him as one.”

The second mistress left the room, and very quickly they had suc- ceded doing a good job in humiliating me. Mistress Rae left me standing there and went into a closet. With her back to me, she tossed me a pair of pink panties and ordered me to put them on. The panties were inside- out, and I was nervous, and it took me a long time to put them on. “What’s the matter, can’t you do a simple thing like put on panties?” she barked at me. I was beginning to feel incompetent. She tossed me a pair of thigh high stockings and told me to put them on. As I did she searched the closet for more clothes. She tossed me a black garter belt. “You do know how to wear a garter belt, don’t you?,” she asked sarcastically.

But I could not get the garter belt tabs to work! I tried and I tried, but the tabs would not stay on. “Uh, Mistress,” I said very tenta- tively. “Would you show me how to do one of these?”

She gave me an exasperated look like I couldn’t do anything right. She came over to show me how to clasp the tab, but it would not work for her either. So it was not my fault! But of course, she would not give me the satisfaction of admitting it. She angrily ripped the garter belt off of me, and went back into the closet.

She got out a beige dress, threw it at me, and told me to put it on over my head. The dress came with a slip – “shouldn’t I put the slip on first?” But the slip was attached. I was confused. I put the whole thing on over my head, but it was tight, and I couldn’t get my arms back out to go through the straps. “Uh, Mistress,” I said very reluctantly, “I’m going to need some help again.”

Mistress came over with a disgusted look, as if I were truly helpless and worthless and why was she bothering with me. She helped me get my arms through, and the dress was on. But I hadn’t realized as I was struggling with the dress, that the stockings had fallen down. “Pull up those stock- ings,” she yelled at me. “You look like an old woman.”

She gave me a pair of white high heels, about three inches I guessed, and told me to put them on, but to put them on like a lady. By this I guessed she meant to squat down daintily to pick them up, rather than to bend at the waist as I might have otherwise done if she hadn’t said anything. Then she told me to practice walking in them, and she said she wanted me walking very sexily when she returned. And again she left the room.

I tried to maneuver in the heels, which were thinner heels than I had imagined, and I tried to swing my hips in a feminine manner. I knew I wasn’t doing either very well. I walked back and forth the length of the room, until I had some measure of ability in the heels. I noticed a video camera high on a wall. Probably for security, I thought, but then I realized that my mistress or the other mistresses could look in on me whenever they wanted.


Mistress Rae returned, sat down in her chair, and had me parade before her. She told me I looked so elegant, which of course was ridiculous, and I felt ridiculous. Then she had me kneel on all fours, with her chair behind me, and she told me to lift my dress, giving her access to my pink pantied bottom.

Whack. She spanked me with her hand. It didn’t hurt, but the surprise of it startled me and I yelled “Ow”. “Ow?,” she repeated at me. “The reply is ‘Thank you Mistress Rae’. Can you remember that?” I told her that I could. So she spanked me some more. Her spanks seemed more for effect than for anything else, as I thanked her for each one. But then all of a sudden there was a whack, and it really stung. She had hit me with her shoe, and it made a big difference. She alternated ass cheeks, and quickened the pace so that my proper thank yous could not keep up with her. These spanks were beginning to hurt and I was about to use my “red” safeword, when she stopped spanking me, without warning.

Mistress Rae told me to get up, take a wooden chair, put it in the middle of the room, and sit on it. Of course I did all this without question or hesitation. “Put your hands behind your back,” she ordered, and I did. And then she produced a pair of handcuffs! She handcuffed one wrist, threaded the chain through the back of the chair, and handcuffed my other wrist. I was really handcuffed! “Now don’t go away,” she said sweetly, as she left the room, leaving me alone and helpless. I tested the cuffs, and they were real. I couldn’t get out now if I wanted.

Mistress let me think about this for a while, and then she returned with a box of cosmetics. She was going to apply my makeup while I was handcuffed. This is one of my great fantasies! She calmly browsed through her box, examining various shades and contemplating how they might look on me. She held my face in her hands, and she told me she was going to make me so pretty. I looked at her face, and I melted.

She applied foundation with a sponge, darkened my eyebrows, applied a couple of shades of eyeshadow, and some eyeliner. Because I flinched from the eyeliner, she told me she would not apply mascara. As she applied each cosmetic to me, she got very close, giving me the opportunity to gaze deeply into her beautiful eyes. I could feel her breath on me. It was very erotic.

A few strokes of blush, and it was time for the makeup finale. As I waited with great anticipation, Mistress started going through her collec- tion of lipsticks. She unscrewed each one as if she were viewing its color for the first time. Finally she chose a shade. As she came toward me to apply it, I made up my mind that I would ask her for a special favor.

“Mistress, would you do something for me? Would you sit on my lap as you put on my lipstick?”

And she smiled and did. She sat right down in my lap. I was hand- cuffed from the back, and pinned by her weight in the front. I was absolutely immobilized as she looked deeply into my eyes, as if she understood my fantasies and read my soul. She told me to open my mouth wide. And then to close it. And then to open it. And close it. She did this several times, just to tease me and to delay the inevitable. She smiled at me and said she wanted to see how long I would keep doing this. She was playing with me. And I loved it.

And then she got down to business. She painted my lips in slow, short, deliberate strokes. She was drawing out the experience of the lipstick for me. She understood how important it was in my fantasies. And she was letting me savor it. I recognized the aroma immediately – Revlon. I asked her the shade, and she told me it was called Exotica.

When she was done, I told her the absolute truth. I would remember that moment for the rest of my life.

Mistress Rae volunteered that lipstick is the most important cosmetic for brunettes, while for blondes it is mascara. She told me that Exotica went well with my coloring.

She decided on a very long black wig. And since I have a big nose anyway, she decided I looked like Cher, from her sixties days. Then she decided I needed a name. She named me Laura.

Then she left me alone again. She told me to admire myself in the mirror. She told me to walk around some more, and to think of some sexy poses. When she came back, she wanted to see how sexy I could make myself look.

I admired myself in the mirror. I barely recognized myself. Not exactly an attractive looking woman, but not the usual me either. I walked around some more in my heels, swinging my hips and swinging my long hair out of my face. I was feeling kind of slutty. The room had a bed in it, and I laid down, hiked up my dress as high as it would go without showing my panties, put one arm over my head and tried to strike a sultry pose. I felt ridiculous, and I’m sure I looked worse. But Mistress, who no doubt was watching me from the other room with the video camera, knew when to come back in. When she did she complemented me on how sexy I looked. I knew the complement was bogus, but I thanked her anyway.

Mistress sat down in her comfortable chair and made me walk around the room some more for her. Then she told me to get some paper towels. Then she surprised me with the most remarkable command. “Wipe off your lipstick, Laura.”

I could not hide the hurt in my eyes. “Already?,” I whined.

“Yes,” Mistress replied simply. And what could I do but obey.

But Mistress had other ideas for me. “Get on all fours, and kneel in front of me,” she commanded. I did this. “Now kiss my shoe.”

Mistress presented her shiny black high heeled shoe for me to kiss. I tentatively put my lips to it. Mistress was not pleased. “Is that the way you kiss your Mistress’s shoe?”, she asked me angrily. “That’s more like the way you would kiss your aunt. Now kiss my shoe with some passion and show me you mean it.” Mistress had inspired me to improve my perfor- mance, and I kissed her shoe, and the other one, with more feeling.

She had me remove her shoes, and I did this ever so gently and lovingly. Mistress was not wearing stockings, and she was wearing brilliant polish on her toenails to match her fingernails. I noticed that some of the polish had chipped off, and wondered if Mistress would give me the privilege of touching up her toenail polish, but that was not to be.

“Laura, you may massage my feet now,” Mistress commanded. I was pleased to do this for her, but not surprisingly, I did not do it to her satisfaction. She made me stop, stand up, and she instructed me verbally on how to massage her feet. When she was satisifed, she told me I may kiss her thighs. I was very excited to do this, and as I kissed higher and higher I could see Mistress’s panties. I wondered how high I would be permitted to kiss. I was of course prepared to kiss her as high and as thoroughly as she demanded, but thighs were her limit.

Mistress got up, went over to the bed, and laid down on her stomach. She told me to come over. She told me to massage the backs of her thighs. I did so, marvelling at their firmness but their softness. She then arranged her miniskirt in such a way that I had access to her ass. What a fine, well-toned ass it was. She was wearing panties that were more like a thong, showing her beautiful ass cheeks in all their glory. She told me to massage her ass cheeks, but to keep my hands on the outside of her only. I lovingly massaged her ass. I had a great desire to kiss it, and decided I had better ask permission first. She granted permission, and I tenderly kissed both of her ass cheeks. It occurred to me that if Mistress had allowed me to keep my lipstick on, there would be two little red lipstick prints on her cheeks now.

Then Mistress got up off the bed, and invited me to lay down on it, on my back. She sat by my feet, and told me she wanted to see me play with myself. I began to stroke myself. Mistress gently stroked my thighs, although not my cock. She gazed at me with a dreamy look in her eyes, and licked her lovely lips. I decided it was now or never.

“Mistress, may I ask you for one last favor?,” I asked. “Would you please put more lipstick on me?”

Mistress obviously understands me more than I will ever know. She smiled as she got up to get the lipstick. She leaned over my prone form, and as I gazed longingly into her beautiful eyes, she ever so slowly repainted my lips with the Exotica lipstick. This was enough to bring me over the top, and I came.

Mistress gave me a paper towel to clean my cock, helped me out of my dress, told me to remove the rest of my clothes, and showed me where the bathroom was to remove my makeup. She gave me Baby Wipes as a makeup remover. When the makeup was gone and I was dressed in my male clothes again, Mistress asked me if I enjoyed the session.

“It was wonderful,” I told her. “There are parts I will never forget.”

Mistress smiled and kissed my cheek. I asked permission to kiss her hand. And with that, she showed me to the door.

The End

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princess alexandria

This House and Madame Stewarts guidance has provided the framework for her self awareness and her acceptance and delight in being herself in the world!

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