Sissys suprise
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Sissy's Humiliation, Part 1 free porn video
Note: I wrote this story over 20 years ago and still enjoy reading it. I
have edited to keep things current, ie Polaroid cameras not long exist. I
hope you enjoy reading as much as I did writing and fantasizing the
content
Sissy's Humiliation
by:
SissyFellatrixFL
Recently I had to attend a trade show in New York. Several weeks before I
attended, I started corresponding with a Lady who lived in Manhattan with
her roommate. Jennifer was a professional person, worked on Wall Street
and her roommate, Holly, worked in advertising. Both girls had recently
been through a messy divorce and were beginning to circulate again. They
both had an interest, possibly because of their chauvinist ex-husbands,
to meet and totally control a submissive male.
We corresponded daily for several weeks with the result being that I had
agreed to submit to their every wish and command.
Jennifer had a fondness for lace and satin and told me that she was going
to take me shopping for a gown. She also told me that before I would be
allowed to meet them, I was to visit a lingerie boutique on the eastside
and purchase a pink satin corset. Jennifer became even more specific! I
was to walk into the boutique with my high heels and stockings in a
shopping bag and announced, "My name is Sissy, and I would like to be
fitted for a pretty pink satin corset." This of course was very
humiliating, but I figured, "what the Hell, no one knows me here and
Jennifer and Holly are worth the embarrassment."
The trade show started on Tuesday, and at my hotel on Monday, around
noon. I checked into my hotel, and as instructed by Jennifer, unpacked my
high heels and a pair of sheer black stockings and put them in a small
shopping bag.
I then caught a taxi to the address that Jennifer and Holly had given me,
on the upper eastside. By this time I was a nervous wreck, but I walked
into the store with my little shopping bag. The store was quite elegant,
with many items of lingerie - bras, teddies, corsets etc. on display.
There were also some unconventional outfits such as leather, and patent
leather dresses and boots and a one wall with what appeared to be bondage
type equipment.
There were three ladies working in the store, two were in their mid
twenties, and gorgeous while the other lady, who was apparently the
owner, was in her mid 30's, and stunning.
She came up to me and said, "May I help you sir?" I stammered and
stuttered a bit, saying that I was just looking for a present for my
wife. She smile and said again, "Are you sure I can't help you sir?" with
a sardonic smile on her face.
At this point, I figured that she was expecting me, and I blurted out,
"My name is Sissy, and I would like to be fitted for a pretty pink satin
corset."
"Ah, so you are Jennifer's and Holly's little sissy boy," she exclaimed
with a giggle. The other girls in the shop looked up at me and also
giggled. With that, the owner of the shop introduced herself to me. "I am
Carolyn, and these are my two assistants, Robin and Cyndi."
"Please follow me, Sissy." She and her assistants burst into laughter
when she said 'Sissy'.
Carolyn then led me into a back room. She instructed me to remove my
clothes and put on my high heels and stockings. Carolyn was quite amused,
seeing me with my body shaved and smooth. She then handed me a pair of
panties that were pink satin, trimmed in white lace, and told me to put
them on. Carolyn then took out her measuring tape and measured my chest,
waist and hips.
When she had finished measuring, she called out to Robin to bring in two
pink bustiers by Darling and told Cyndi to bring in two bustiers of the
same color by Lady Marlene.
In a few minutes, the two girls came in with the bustiers and they also
burst into laughter seeing me there in high heels stockings and panties.
Carolyn then instructed Cyndi to put one of the Lady Marlene bustiers on
me. The first one was white satin, with pink lace trim and had a zipper
on the front. Cyndi wrapped the bustier around me, zipped up the front
and then attached the garters to the stockings. Cyndi stepped back and
Carolyn had me walk around and model the bustier... they were quite
amused at this!
The three ladies discussed my appearance in this bustier, and decided
that it did not pull my waist in enough.
Carolyn then told Robin to get a satin corset in pink. Robin returned
with a Victorian style corset in was pink satin, very heavily boned and
trimmed in black lace. Robin put this corset around me, fastened the
front then had me turn around and hang on to the back of a chair. Both
Robin and Cyndi worked hard on lacing up the back... pulling it tighter
and tighter so that I had difficulty in breathing. Carolyn then told me
to stand up straight, and as I did, I felt light-headed from the pressure
of the corset. Carolyn then measured my waist and exclaimed that the
corset had reduced my waist by 4 inches!
She then had me walk around in this corset, and all three of them
exclaimed that it was 'perfect'. Carolyn then told Cyndi to go and get a
matching bra. Cyndi returned with a black satin bra, trimmed in lace, and
a pair of black lace bikini panties that matched the color of the black
lace on the corset. Cyndi helped me put on the bra, then they all stood
back and watched me change from the pink to the black lace panties. All
the time they were giggling and making comments about 'the sissy-boy that
Jennifer and Holly had to play with'!
Since I had neither makeup, nor wig on, it was quite obvious that I was,
indeed, a feminized male. Robin then went back in front and returned with
some pads for my bra, as well as another pair of black lace panties. She
placed the pads in my bra, so that I appeared to have B size breasts. She
then handed me a second pair of panties and had me change into them.
These panties were of the crotchless type! I was mortified, standing
there, corseted, with a bra, and my maleness exposed and surrounded by
black lace, while the three women made me walk and model my new outfit.
Carolyn then said, "How about the finishing touch, Cyndi?" Cyndi laughed,
went back out front and returned with a pink ribbon, the same color as
the corset.
She walked up to me and tied the ribbon around my manhood in a pretty
little bow. This really sent all three girls into hysterics, as they
again had me prance around for their amusement.
Carolyn then had me stand against the wall and pose with one foot in
front of the other, while Cyndi and Robin stood on either side of me,
each of them putting their arms around my back, while Carolyn took
several photos of her latest customer.
Carolyn then told me, that she would like me to return, fully dressed as
a female, on Thursday morning, before I returned home. She indicated that
she was beginning to do so mail-order business for cross-dressers and
would like me to model some of the other lingerie, clothing and 'toys'
for her catalog that she was preparing to mail out to these customers.
I protested, but Carolyn reminded me that she had some nice photos of me,
as a male, dressed in lingerie, which she would be delighted to return to
me, after I had helped her with her 'little request'. Carolyn then told
me to put on my slacks, shirt and street shoes over my lingerie. I put my
high heels and my male underwear in my shopping bag and stepped out to
the front of the store.
"I will see you on Thursday, is that correct, Sissy?" demanded Carolyn. I
thought to myself, I am not coming back, who cares about the photos, no
one will know me here in New York, and she had no idea of where I am
from. "Yes, no problem, I will be here Carolyn," I replied, lying through
my teeth.
"That is wonderful, sissy boy", she replied, 'the photographer will be
here and all set up, we will only need you for two or three hours! Don't
be concerned about paying for the lingerie you are wearing, you can
consider that as payment for your 'modeling services'."
"Oh yes, one more thing, Sissy," she leered, "here is your wallet you
dropped while Cyndi and Robin were lacing your corset, and I notice you
have quite a few credit cards. I think I will keep your Visa card, and
you can retrieve it on Thursday!"
"Damn!" I thought. "This woman plays hardball." I could only smile weakly
as I agreed to return on Thursday.
"Remember, sissy-boy, I want you dressed very sexily and made-up very
exotically," she giggled... as did Cyndi and Robin, "you may have to
model some of our more erotic items!"
Carolyn then gave me a little kiss on the cheek, as did Cyndi and Robin.
"Sissy, return to your hotel room now, I will call Jennifer and Holly and
tell them that you have been fitted to their specifications, and are
waiting for them."
As I rode back to my hotel, I kept thinking to myself, 'I enjoy a bit of
humiliation and being made to serve an assertive woman, but have I gone
too far this time?"
As the taxi took me back to my hotel, I was becoming more and more
apprehensive. However, because of Carolyn's sequestering of my credit
card, I had lost complete control of the situation and had no choice,
other than to do exactly what I was had been told to do! The corset was
extremely tight, making me feel very subjugated, allowing me to only sit
absolutely upright. It was, as though, I was in perpetual bondage!
As the taxi pulled up in front of my hotel, I paid the driver and went up
to my suite. As I entered, I removed my shirt, reached behind and
loosened the laces of my corset allowing me to breathe more normally. I
sat down, poured myself a glass of wine, and attempted to relax for a few
minutes, and wondering what was going to happen next. I knew, from my
previous correspondence with Jennifer and Holly that I was going to be
their 'Barbie Doll' for the day, and that thought was extremely erotic to
me. However, the anticipation of their taking me out in public for part
of the role-playing, continued to cause apprehension in my mind.
I continued to berate myself for being so stupid as to allow Carolyn to
grab my credit card. I did not really feel as though she would use the
card in a dishonest way, as I could very easily call and cancel it.
However, she knew who I really was! I had lost my anonymity and she was
totally in control. Since she was friendly with Jennifer and Holly, they
too, knew my real identity, and consequently, exercised that control, as
well!
As I considered my options, and determining there were none, the phone
rang. I answered the phone, my voice breaking in nervousness. "Sissy,
this is Mistress Jennifer", are you ready to amuse me and Mistress
Holly?" the voice said.
"Yes, Mistress," I replied, "I am ready to please and amuse you!"
Jennifer responded with a throaty laugh, "Good, sissy boy, we are calling
from the lobby... We will both be up in about 2 minutes. Remove your ugly
male clothes, and be ready to answer the door in your new lingerie and,
of course, your high heels." Before I could answer her, she hung up the
phone. I removed my slacks, socks and shoes and slipped into my high
heels.
As I looked in the mirror, I saw a normal, reasonably attractive man, but
this man had on a pink wasp-waisted corset, satin and lace bra and
crotchless panties, 4" high heels and a pink bow around his penis! I
looked absolutely ridiculous... totally sissified! But, I had little time
to analyze my appearance, as I heard a knock on the door. I walked over
to the door, the high heels causing me to wiggle my hips in a very
feminine walk.
As I opened the door, I stood behind it, so no passers-by could see me,
but still allowing my 'guests' to enter. "No, no, sissy-boy", I heard
Jennifer's voice say, "This is no way to greet your guests. Come out from
behind the door and greet us!"
I was a nervous wreck, what if one of the other hotel guests saw me... "I
said NOW, Sissy, unless you would like us to take you for a ride on the
elevator, dressed as you are!" I sheepishly came out from behind the door
and there they stood in front of me, just outside the door, both of them
had amused smiles on their faces.
I was in shock. Both Jennifer and Holly were absolutely stunning!
Jennifer was about 5'8', with jet-black hair and vivid green eyes, her
figure was incredible. She was wearing, what was obviously, a very
expensive business suit with 4" heels. Holly was about 5'4, with auburn
hair and blue eyes, and she too had an incredible figure. Holly was also
dressed in very expensive clothes, a glove leather skirt, white lacy
blouse and matching leather blazer. They both eyed me from head to toe,
and simultaneously burst in laughter as they noticed the pink bow around
my penis, visible through my crotchless panties.
"Oh Carolyn has outdone herself this time!" exclaimed Holly. Jennifer,
unable to stop laughing, shook her head in agreement. I felt very
uncomfortable standing there with the door wide open, but the two ladies
then decided to enter, and I closed the door with a sigh of relief. They
both sat down, and continued their amused assessment of me.
"Oh you really are a sissy," exclaimed Jennifer, "I never thought you
would actually go through with this, but I knew if we could get you into
Carolyn's, the rest would be easy!" They then had me walk back and forth,
modeling my new lingerie.
As I did this, Holly suddenly exclaimed, "The little sissy faggot has
loosened his corset! Let's take care of that, right now, Jenny!"
Both girls stood up, and ordered me to get on my hands and knees. As I
obeyed, Holly walked behind me, put one knee in the small of my back and
started re-tightening the laces of my corset, while Jennifer stood in
front of me, leaning on my shoulders, so I could not move. Again, I felt
lightheaded as the corset constricted my breathing, and my waist was
nipped.
Satisfied, the girls had me stand again, and walk back and forth for
them. The constriction or the corset, coupled with my high heels, made me
sway my hips even more in a feminine 'swish'. Holly exclaimed, "Oh that
is so much better, you are just so cute!" I blushed in shame, as they
both giggled. "Time is running out, and we have an appointment", said
Jennifer, "Put your slacks, shirt and male shoes on, sissy, we're going
fit you for your first gown."
As I dressed, Jennifer and Holly walked into the bedroom closet and
inspected my feminine wardrobe, talking and giggling. They then took my
high heels and put them into a small shopping bag. "Let's go sissy,"
smirked Jennifer, "and be more careful with your wallet this time," she
giggled. Totally embarrassed, I followed them as we left my suite and
took the elevator down to the lobby and hailed a taxi. Holly gave the
driver instructions, and we all sat back, with me between them.
As we drove, Holly and Jennifer whispered little comments in my ear, "I
love your little pink bow, Sissy."
Holly whispered... Jennifer continued, "Oh I can't wait to see you in
your little French maid uniform." Both girls giggled as the taxi driver
looked in his mirror with an amused expression on his face. Finally the
taxi drew to a halt in front of a group of stores. Jennifer paid the
driver and we all got out.
"Our appointment is for another 30 minutes," said Holly, "shall we do a
little window shopping, Jenny?"
Jennifer replied, "Great idea Holly!" We walked into the closest store,
which was a large department store. As we browsed around, we came to the
formal department. "Oh I can't wait to get sissy into a gown," exclaimed
Jennifer. Holly then took one of the gowns off the rack and held it up
examining it. She then walked over to me and held it against me, then
ordered me to hold up while they both stood back and appraised the gown,
as I held it against me.
Several other customers watched in shocked amazement, as the girls
giggled over my discomfort. Holly and Jennifer selected a few more gowns
and made me hold them up, while they appraised them. Finally a sales lady
came up and asked if she could be of assistance. Jennifer and Holly both
said, thank you, but not right now... these gowns are a bit too
sophisticated for our sissy friend... we need something a bit more
frilly. The sales lady was a bit shocked, and with that we all turned and
exited the store...my face a vivid red in embarrassment.
We walked about a block and finally entered a bridal store. A very
attractive lady, in her 40's greeted the ladies and looked at me with an
appraising eye, sizing me up as she chatted with Jennifer and Holly.
Jennifer then turned to me and said, "Sissy, this is Mrs. Walston. She
and her staff are going to fit you for a lovely evening gown." Mrs.
Walston held out her hand with an amused expression on her face. "I am so
delighted to meet you, Sissy, please follow me."
She then led me to a back dressing room that was mirrored on all four
walls. Jennifer and Holly followed, and sat down as Mrs. Walston prepared
to do her work. Mrs. Walston told me to remove my clothes, and her eyes
raised, and she smiled, when she saw the crotchless panties and the bow.
"My, ladies, you certainly have trained him well!" she exclaimed.
"Oh no, Mrs. Walston, by the time we are done, it will be HER, not HIM,"
giggled Jennifer.
Mrs. Walston then called one of her assistants. A younger girl, in her
early 20's walked into the dressing room. Her eyes registered shock, when
she saw me standing there in my lingerie and heels. "Bonnie," said Mrs.
Walston, "I would like you to meet 'Sissy'. We are going to fit 'her' for
a pretty prom gown. Would you please, go out and select four gowns, size
16, and I would like each gown you select to have a very full skirt.
Bonnie also, please bring in a long very full petticoat." Bonnie grinned,
as she looked at me, and went to select the gowns.
She returned a few minutes later, her arms laden with several gowns and
the petticoat. Mrs. Walston then instructed Bonnie to help me in putting
on the long, very full, taffeta petticoat. As Jennifer and Holly watched,
Mrs. Walston and Bonnie dressed me in several gowns. I had to model each
one for Jennifer and Holly.
They continued shaking their heads, no to each one I tried on. Finally,
Bonnie returned with a gown that was red taffeta with a very full long
skirt, reaching to the floor. It was trimmed in white lace around the top
of the bodice, a flounce of white lace around the hips and waist, and the
bottom six inches of the skirt. As Bonnie zipped the back of the gown,
both Jennifer and Holly exclaimed, "That's the one!"
They had me walk back and forth in the gown, which was very full with the
petticoat underneath, and again they both agreed that this was the
perfect gown for Sissy. "We can make her look just like Scarlet O'Hara,"
giggled Holly. Mrs. Walston and Bonnie both grinned. Mrs. Walston then
proceeded to mark the hem and make a few marks for some minor
alterations.
"When will 'she'be needing this, ladies?" asked Mrs. Walston.
Jennifer replied, "Is it possible that we could pick this up this
evening, just before you close?"
Mrs. Walston then took another look at the alterations required, and
replied, "Certainly, just a little shortening, and a bit taken in at the
waist, that should only take us an hour or so."
Bonnie then unzipped the gown, helped me out of the gown and removing the
petticoat. "We will be back at 7:30, just before you close, Mrs.
Walston," replied Jennifer. With that, I was allowed to put my slacks,
men's shoes and shirt back on. We walked to the front of the store, where
I was required to pay for the gown and petticoat.
Mrs. Walston thanked me and said, "We shall see you THREE girls around
7:30." Everyone, except me, giggled at Mrs. Walston's comment. It was
about 4:30 when we left Mrs. Walston's shop and headed back to the hotel.
Both Jennifer and Holly chatted about their new 'Barbie Doll' during the
taxi ride, as though I wasn't even there! We arrived at the hotel, went
back upstairs to my suite and the two girls sat down and kicked off their
shoes.
They both had me remove my male clothes again and helped me remove my
corset. Jennifer told me to go draw a bath for myself and make sure that
my legs were smooth and soft, as they wanted Sissy to look very sexy
tonight when they took her to dinner.
I started the bath running and went out to the living room of my suite.
Jennifer and Holly had kicked their shoes off, had their feet up and were
relaxing.
They had me remove all of my clothing, including my lingerie. Jennifer
then stood up, grabbed her purse and told me to follow her. She walked
into the bathroom, tested the bath water, and then turned off the
spigots.
She then reached into her purse and pulled out a can of Nair, which she
proceeded to rub all over my legs. She ordered me to shave my face extra
close, as she watched. Jennifer then ordered me into the bathtub.
Jennifer left me alone for about 15 minutes, as the hot bath relaxed me.
Finally she shouted in for me to rinse off, get out of the tub, dry
myself and come out to the living room.
As I walked into the living room, I noticed that all of the clothing I
carried with me was laid out on the sofa. Holly was examining my makeup
kit, while Jennifer ordered me to sit down.
Holly then got up and started to make me up. First she put a foundation
of Derma-Blend, to hide any tinges of my beard. Then she put a normal
foundation over the Derma-Blend, then started shading my face, first with
a darker color so that my male features were diminished, then using
lighter colors to accentuate my cheekbones. She then applied heavy
eyeliner to both the bottom and top of my eyes, and then blended in
several shades of blue eye shadow. After an application of mascara to my
lashes, and a blush on my cheeks, she applied a very bright red lipstick
to my lips. Finally she took my wig and placed it on my head and teased
it until she got the effect she wanted. As Holly stepped back to examine
me, a big smile broke out on her face. Evidently, she was pleased with
her work, but I had no mirror in front of me to appraise her handiwork.
Holly told me to stand, and Jennifer placed the corset back around my
waist and fastened it in place. I was then ordered back on all fours
again, as both girls proceeded to lace me tightly again! I experienced
the same lightheadedness that I had experienced earlier that day, as I
stood up.
This time the girls allowed me to wear the normal black lace bikinis,
without the humiliation of having to go crotchless with the pink ribbon.
They then smoothed a pair of sheer black stockings onto my legs, and
fastened the garters from the corset.
Jennifer sorted through my wardrobe and selected a black taffeta flared
mini skirt, and a black satin blouse. As I put the skirt and blouse on,
Holly handed me a bright red patent belt. Long dangly earrings and beads,
the same color as the belt, competed the ensemble. I sat down while Holly
painted my fingernails the same bright red, then Jennifer handed me 5"
black patent high heels. I stood up, feeling very feminine, but still
very embarrassed as the two girls again smile big smiles.
"Go take a look in the mirror, Sissy", said Jennifer. I walked into the
bedroom, took a look at myself in the full-length mirror and saw a very
'hot' looking woman, staring back at me! I had dressed many times before,
and I was fairly accomplished at make-up, but I had never looked this
good! Holly really knew her stuff! However, I did look a bit slutty...
especially with the 5" 'fuck me' pumps!
Holly and Jennifer then slipped their shoes back on grabbed their
pocketbooks and handed me mine.
"Well, Sissy, I think we three girls should go out and have some dinner,"
said Jennifer. "Let's go."
We exited the hotel, and Jennifer flagged down a taxi and gave him the
address of Mrs.. Walton bridal salon. We entered the salon and Mrs..
Walton approached us. "Oh doesn't Sissy look gorgeous!" she exclaimed.
"Shall we have her try her new gown on?"
Jennifer replied, "I'm sorry Mrs.. Walton, but we have a dinner
engagement. We'll bring her back soon for another gown, and this time she
will be dressed as "Sissy" when she arrives. As a matter of fact, from
now on she will be known merely as "SISSY"!
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Mrs. Walton giggled, then placed the gown in a large valet bag, gave us
all a kiss on the cheek and wished us good luck.
Brandy
- 19.06.2021
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