Cyndi's Gown Ch. 01

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 Candy, 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 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 Candy, 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 Candy." She and her assistants burst into laughter when she said 'Sissy Candy'.

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 Polaroid pictures 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 Polaroid's 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 Candy?" 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 'modelling services'."

"Oh yes, one more thing, Sissy Candy", 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. "Candy, 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 to 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 Candy, 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 analyse 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 Candy, 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, modelling my new lingerie.

As I did this, Holly suddenly exclaimed, "The little sissy 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 Candy, 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, Candy, 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 'Candy'. 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 Candy. "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 Candy to look very sexy tonight when they took her to dinner.