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From alt.sex.stories.tg Fri May 3 11:04:51 1996
Path: fu-berlin.de!nntp.coast.net!news.sprintlink.net!castle.nando.net!news
From: Eve <eve@aol.com>
Newsgroups: alt.sex.stories.tg
Subject: Chicago
Date: Tue, 30 Apr 1996 20:12:33 -0700
Organization: The Transgender Post
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~Subject: chicago.txt - femdom, TV, humiliation
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.