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Jill's Weekend In Vegas - Part 1 free porn video
Jill's Weekend In Vegas - Part 1
By Jill Weisser
During the press conference there were all the same old
cliches. I was going to quit work, I was going to go on a
great vacation, buy a nice house, all the same, tired old
crap. But deep down I knew exactly what I wanted. I was
going to use some of the 14 million I had won in the
lottery was to fulfill a fantasy. I had plenty of money and
I'd have plenty left over when I was done.
That was about a year and a half ago. Sure, I bought the
nice house and a boat and have been on a few trips all over
the world. I have also been getting some plastic surgery
done. I had a nose job and some other work to make my face
more androgynous. You see, before I won all that money I
was a crossdresser. Heck, I still am. I love to wear
women's clothes. I love the lingerie, skirts, dresses,
make-up, all of it. I had a pretty fair collection and had
even gone out once or twice dressed but I had never really
gone all out. I was always afraid my friends would notice
if I shaved my legs or I didn't know enough about make-up
to do a good job. Finally, I was coming to the point where
I could do it right.
I've been doing more than just the plastic surgery over the
last year and a half. I've let my hair grow out, been on a
pretty strict diet and exercise program, been taking make-
up lessons, and getting my wardrobe together. It was a
little difficult at first, embarrassing.
That's where Cindy comes in to the story. For lack of a
better term, she's my project manager. Cindy has been
finding everyone and everything I need to pull this off.
She set up my private make up lessons, brought in designers
and dressmakers to help with my wardrobe and even had me
taking lessons in poise and manners.
Cindy is a lady of the evening. Not the kind you pick up on
the streets after dark, she was all class. Her clothes,
makeup, and hair are always perfect. At about 5 foot 8 with
a dark mane of thick brown hair, she was mature a little
over 30 years old and absolutely gorgeous. She was very
intelligent and discussed things in a highly professional
manner. She worked out of her apartment, a high rent part
of Downtown, which was very well appointed. When I first
described what I wanted her for, she looked at me like I
was insane. But when I explained where my money was coming
from and that price was of little object, she asked me what
precisely I was looking for and what I expected of her. We
talked for several hours and I knew she was the one.
There is one particular part of my training has been the
most enjoyable, at least on Fridays. She has me wear a
locking, curved metal cylinder over my cock so I couldn't
get off unless she lets me. She had explained it was all
part of the process and I had reluctantly agreed. Every
Friday night she would let my penis out, dress me up in the
sexiest outfits and drive me wild with lust. I was curious
why she would only dress me up during these Friday night
sex games. I later figured out it was to help develop a
Pavlovian response to being dressed as a girl, so I would
associate sex and orgasms with being dressed.
After about 4 months she started training me to suck on a
dildo. Then at 8 months I was getting fucked in my ass. She
also told me I needed to be more vocal or I wouldn't be
allowed to cum. So I learned to moan and beg her to fuck me
harder and let me cum. She was a great teacher and I was
becoming a perfect little slut.
Last week Cindy said I was ready to graduate and she had a
special weekend planned for me. Two days ago had been very
difficult at the spa, getting prepped for this weekend.
Waxing your legs can be a very painful process. I had my
legs, arms, chest, back, ass, everywhere done. The
moisturizing body massage afterwards helped somewhat and
then two days later the rash had completely gone away
leaving me hairless and soft. I was now ready for my
special weekend and my dream come true.
Friday Morning:
When I woke up Friday morning I hardly had the time to
drink my morning Pepsi when Cindy showed up.
"All right Jill, are you ready for your fantasy?" she
asked.
Of course I was ready, I had been planning for this for
about a year and a half. The first thing Cindy had me do
was take a long hot bath, it was lavender scented. Her long
fingernails felt amazing while she washed my hair and
massaged my scalp. After my bath she dried me off and gave
me the once over. She was pleased with the waxing job I had
received two days earlier. She handed me a white satin bra
and panty set as well as a short kimono robe. After I had
put them on, she took me downstairs to the kitchen.
There were three women and a salon chair waiting for me in
the middle of the room. I recognized Stacey, she had given
me a few makeup lesson in the past. I assumed that her two
helpers were from the salon she owned. She introduced Trina
and Diane and had me sit in the chair. For the next three
hours the three of them gave me a complete salon makeover:
A pedicure, which included a foot massage and painting my
toenails, a manicure, with a paraffin wax treatment, a
complete set of acrylic nails, and a polish which matched
my toes, a haircut and style, and lastly my makeup
application.
I had let my hair grow out over the last year and a half
but hadn't done anything more than pull it back in a
ponytail. Stacey had to cut quite a bit to get the style
she was looking for but was happy with the length I had
achieved by letting it grow. It gave her plenty of length
to work with. After she had cut my hair she spent the next
hour coloring it. She explained she was going to lighten
it, which would give me more of an auburn color versus the
brown color that was my own.
Trina and Diane had finished up my hands and feet. Trina
had an opportunity to pluck my eyebrows while Stacey
finished my hair. I was starting to get a little curious
about how I was staring to look. All I could see were my
fingers and toes, which had been painted a bright red. I
asked Diane if she could find me a mirror but Stacey said
not until they were done. Finally done with putting my hair
in curlers, Stacey went to work on my makeup. It took her
about 45 minutes to get the foundation, blush, eye liner
and shadow, and lipstick on. Making sure the curls were
set, she went back to styling my hair until it was just
right.
I wanted to run to a mirror when I was done, but Cindy told
me to close my eyes and led my back upstairs to my bedroom.
I could see she had a mirror set up facing the end of the
bed but it was covered. Cindy told me I would be able to
look in a few minutes but I had a few things to put on
first. She walked over to me and slipped the kimono off my
shoulders. She slid a pair of breast forms into the cups of
my bra and encircled my waist with a white lace garter
belt. Slipping my panties off, she sat me on the foot of
the bed. With a slow hand, Cindy rolled a pair of very
sheer white stockings up my calves, over my knees and
thighs. She deftly attached the garter tabs to the tops of
my stockings and pulled out a pair of white leather strappy
sandals with four inch heels.
After sliding on the sandals and setting the ankle straps
she asked, "All right sweetie, are you ready for the
unveiling?"
I thought she was going to take the cover off of the mirror
but instead she pulled open her wrap around dress to reveal
herself in a black leather corset and thigh high boots. As
she walked over to the mirror, I could follow the thin
strap of her thong get lost in the recess of her gorgeous
ass. She grabbed a long cord attached to the fabric
covering the mirror and walked over to me at the edge of
the bed. She handed me the cord and told me I could pull of
the cover off when she had reached the count of five.
One. Cindy knelt in front of me as I sat on the edge of the
bed and she spread my legs open at the knees.
Two. She ran her fingernails lightly over my stocking clad
calves tracing her way up to my thighs.
Three. Leaning in close to my now very hard cock, she
slowly ran her tongue in circles around the head.
Four. Reaching her hands under my legs, she had my legs
resting in the crooks of her arms as she took my entire
shaft into her warm, moist mouth.
After she had bobbed her head down my shaft two times, she
pulled up and my penis popped out her mouth just long
enough for her to say, five.
I pulled on the cord as Cindy once again dropped her mouth
onto my waiting cock. When the mirror finally revealed
itself I could hardly believe my eyes. I was watching a
sexy woman in thigh high boots from behind as she was going
down on a very pretty redhead wearing white stockings and a
bra. It actually took me a few seconds to realize that I
was the pretty redhead.
On a closer look, I could see the similarities between me
and the girl looking back at me. It looked like what my
sister would look like, if I had one. It was a surreal
experience seeing the girl in the mirror run her fingers
and bright red nails through the hair of her sexy
girlfriend and feeling Cindy's hair as I ran my fingers
through it. The sensations of sight, sound and touch were
so overwhelming I quickly felt the familiar sensation in my
balls as I was about to cum.
I screamed out as I came and the girl in the mirror writhed
in ecstasy as she climaxed under her partners
ministrations.
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