Cyndi's Gown Ch. 02

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Charles' fantasy goes FAR beyond his original intent.
8.5k words
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Part 2 of the 3 part series

Updated 06/10/2023
Created 04/29/2021
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The next day, I attended my trade show, but I just could not keep my mind on business. Quite frankly, I had always fantasized about being a true submissive slave, but now that it had happened once, and I was going to be "auctioned off" to total strangers that coming night, I decided that I was not going to go through with such a scenario.

I returned to my hotel and, as I entered my room, the telephone rang. It was Jennifer. I told her of my decision and she promptly replied, "Oh, but you are going, my dear Cissy! You see, I have friends at several banking institutions, and they have thoughtfully provided me with your home address and telephone number, after I gave them the number from your credit card that Carolyn is holding!"

I knew I had been had - I had absolutely no choice, either expose myself to extremely embarrassing black mail, or comply. Jennifer continued, "Cissy, you are to bathe, and take extreme care that your entire body is smooth and hairless. Holly and I will be there in one hour. We have a busy evening ahead of us!" There was an abrupt click as she hung up the phone.

I drew a hot bath and made certain that I was smooth all over, as Jennifer had demanded. As I was drying off, there gas a knock on the door. I opened the door for Holly and Jennifer. They both marched in and sat me down in a chair. Holly turned to me and said, "We don't have a lot of time to waste, Cissy, we have to be at the club early, and we have to have your make up perfect."

"But why so early?" I asked, "The auction isn't until after the floor show!"

Holly replied, "Oh, I guess we forgot to tell you, Cissy - Mistress Victoria requested your services tonight. Several of the waitresses have called in sick, and she is extremely short handed."

I was aghast! "But I don't know how to waitress, and..."

Jennifer interrupted me "Cissy, you can carry drinks on a tray as well as anyone can! Don't argue, just be quiet while we do your makeup!" I shut up, knowing that arguing was futile - I was going to do what they wanted me to do, regardless of how embarrassing it might be!

The girls finished making me up, slid sheer black stockings over my legs then ordered me to stand. Holly grabbed a suitcase and opened it. In it was the same uniform that the waitresses had been wearing the previous night!

I was laced into the heavily boned red satin corset. The garters were attached to my stockings, then they slid frothy petticoats up over my legs. The matching red satin skirt and black lace apron that the other waitresses had been wearing came next. As Holly slid a pair of lacy crotchless panties on me, Jennifer forced my feet into a pair of black patent high heels.

They both stood back and appraised their handiwork. "Got to have you looking great, Cissy, one of the publishers of kinky films and magazines will be there tonight to photograph and videotape for their publications and films."

Both girls broke into hysterics at the look on my face. "Oh, Cissy, don't look like that", replied Holly, "You're just what all of their customers want to see!"

With that, they threw a coat over me and escorted me to the elevator. All three of us got quite a few lewd stares form the other passengers. The girls basked in the attention, but I was paranoid that someone would realize that I was not a real "she". As we exited the elevator, a female passenger whispered to Jennifer - just loud enough so I could hear- "I like the way you have your sissy boy trained - care to share him with my husband and I?"

Jennifer responded by opening her purse and handing her a business card from Les Club Bizarre. She told the lady that the card would admit her and her husband as Jennifer's guests, and that I would be waitressing tonight, and would be auctioned off as a slave at the end of the night. She also advised the lady to ask for Cissy as their waitress. As the lady thanked her, Jennifer opened my coat so the lady could see my uniform. Her eyes widened and then a smile came over her face. "We will be there, I hope she provides good service!" Jennifer assured her that I did and that she looked forward to seeing she and her husband there.

Holly flagged down a cab and we were off to the club. When we arrived at the club, Mistress Victoria couldn't thank Jennifer and Holly enough. "Let's see how Cissy looks in her uniform, girls". They took my coat off and Mistress Victoria walked around me with an appraising look. "She looks just wonderful, girls, thank you!" Mistress Victoria then went to her desk drawer, "I forgot to give you these girls", and she proceeded to put leather cuffs with snaphooks on my wrists, and ankles, followed by a matching leather collar. "There, all official", said Mistress Victoria, "Now she'll be able to provide the extra services our guests demand." In horror, I suddenly remembered the waitress who had be restrained to my chair, the previous night, and made to service me!

She then turned to me and instructed me. "You will greet each guest tonight, tell them your name is Cissy and you will serve them in anyway they wish. Should you displease any guest, it will be brought to my attention and I warn you Cissy, should you prove to be uncooperative, you will spend an evening or two at one of my brothels. The clients there are not as sophisticated and considerate as the members of the club. On the other hand, if you serve well, you will find your pretty red corset stuffed with twenty-dollar bills. The choice is yours!"

Mistress Victoria led me away to a lounge, where five other waitresses were all sitting and relaxing before the members started arriving. She introduced me and left me with them. The girls immediately welcomed me with enthusiasm. One girl turned to me and said, "Are we glad to see you - usually we have ten girls waitressing, we're still short four and are going to have to bust our little fannies to keep everyone happy, but one more certainly helps!" The other girls all nodded in agreement.

They had me stand up to make sure my stockings were straight. As I stood, the petticoats made my skirt stand straight out revealing my crotchless panties and, of course, my maleness. They all burst into laughter. "That's why 'her' name is Cissy!" one girl exclaimed, "because that what HE is!"

I was mortified as the giggles continued. Another girl exclaimed, "Oh I can't wait to see Cissy restrained to a member's chair, performing a blow job! Wonder how many dozen cocks she'll have in her mouth tonight!"

The giggles subsided as Mistress Victoria entered the lounge. "All right ladies, the members are starting to arrive - I know we are a bit short handed this evening, but I do not expect the service to suffer in the least. If one of you has to perform more personal services than the others, I expect the other waitresses to make sure that the member still get prompt service on their drinks." Mistress Victoria glanced at me and said, "Cissy may be spending quite a bit of the evening on her knees, so please make sure her tables' drinks are kept fresh". The girls all laughed as I blushed and we headed to the entrance to greet the guests.

There I was, 'one of the girls', dressed in a red satin corset, extremely short flared skirt and lacy apron, very high heels and stockings. Worst of all, the layers of petticoats made the skirt stand out so EVERYONE could see I was really a sissy boy!

As the guest began to arrive, the first few asked the maitre Robert, for their favorite waitress. A very striking couple arrived and asked him for Wendi. "I am sorry sir, Wendi is ill this evening. Would you care to pick another waitress, or shall I assign one to you?" Just as the man was about to tell Robert to assign a waitress, his wife noticed me. She looked down at what was under my petticoats giggled and said, "we'll take 'her'!"

I followed them to their table, mincing my steps because of my high heels. "Good evening madam, sir, my name is Cissy. I am your waitress for the evening and will serve you any way that you wish. May I serve you a cocktail?" The lady looked at me with amusement, then turned to her husband, "Gawd, Bill, will you look at this sissy! This is going to be a great evening!" Bill looked at me "I'll say, Sammy, this is going to be one hell of an evening! Cissy, a Tanqueray Martini for Mistress Samantha, a Chivas on the rocks for me - and be quick about it!"

I curtsied, "yes madam, sir, right away!" as I minced off to their giggling.

I returned quickly with their martinis. After I had served them, Mistress Samantha ran her hands under my petticoats, playing with my penis, as she chatted with Bill. Suddenly she squeezed me hard, and ordered me to kneel before her, under the table. The table, as were all the tables in the club, was glass, so the patrons could see what was going on, beneath the table. The next thing I knew, my wrists were clipped to the legs of her chair, and my collar clipped to a ring in the seat, right at the level of her pussy.

She spread her legs and lifted her skirt. She had no panties on and began to ride my face with her pussy, forcing her clitoris against my lips. "Tongue me, Cissy, use your Tongue on me!" I licked and teased her clitoris with my tongue, trying hard to please her - suddenly she grabbed my head, almost crushing my face as she climaxed with a moan. "Ooohhh Cissy! Ohhhhh," she exclaimed. She reached down and gently lifted my chin, so I was looking up at her. "Cissy that was a wonderful beginning for the evening, I am sure I will need your services quite a few times tonight."

She reached into her pocketbook took out a lipstick. While tilting my face up, she freshened my lipstick. "There you look pretty again, Cissy. Bill just loves hot red lips wrapped around his cock!" Mistress Samantha then unclipped me from her chair and ordered me to crawl over to her husband, who quickly clipped my wrists the legs of his chair.

As I knelt there helplessly restrained, he unzipped his fly and pulled out his penis. Although it was not the biggest I had ever seen, it was a good six inches long and thick. Bill then reached down and squeezed my cheeks, forcing my mouth open. He thrust his hard cock into my mouth, grabbed the back of my head with one hand and clipped my collar to the chair with the other. I was helpless with a cock plugging my mouth and unable to move! Bill just sat there without moving. "I'm going to finish my drink, Cissy. You are to keep your tongue going up and down the shaft while I leave my cock in your mouth." All I could do was tongue the underside of his shaft, as he and Mistress Samantha drank their drinks and chatted. Occasionally Samantha would look down and make some comment. "Ohhh what a cute little sissy cocksucker, Bill - she looks so pretty on her knees!"

I continued working on Bill's cock, when I heard the voice of the waitress who had earlier said she couldn't wait to see me restrained, giving a blowjob. "Madam, Sir, I see your waitress is busy, would you like me to freshen you drinks."

Samantha and Bill said yes and thanked her. Meanwhile, Samantha, who was obviously watching me through the glass tabletop, continued to chat with Bill about my cocksucking abilities. Bill started to move back and forth, pumping my mouth, thrusting deeply into my throat. I almost gagged, but remembered Mistress Victoria's threat about working in her brothel. Suddenly hot sperm started filling my mouth, I swallowed frantically, but couldn't get it all down.

Just at the moment his cum started oozing past my lips and onto my face the other waitress arrived with their drinks. "Here you are Madam, Sir", she said as she placed the drinks on the table, "Is your waitress satisfactory?"

Bill looked up at her and said, "Very, satisfactory, an Excellent cocksucker." He then reached down and released my collar and cuffs. "That will be all for NOW, Cissy - thank you."

I stood, curtsied to them, with cum all over my lips and face, and minced back towards the entrance. The other waitress followed behind me. "Oh you are a hot little cocksucker!" she giggled, "and that cum looks very fetching on your face! You had better go back to the lounge and quickly freshen up your make up Cissy," she taunted. As I entered the employee lounge, two of the other girls giggled at my sperm coated face. I quickly cleaned myself, freshened my makeup and reported back to Robert.

As I reported back to the maitre'd, Robert, I was told to report to a party of eight, whom had just been seated. As I approached the table, my stomach dropped! Seated at the table, was my boss, his secretary, the President of my company and his secretary, along with two other couples! I turned around to go back to tell Robert of my problem. When Mistress Victoria intercepted me. "Where are you going, Cissy! You have a table to serve, get over there!" she demanded. I quickly blurted out my problem, but Mistress Victoria was not sympathetic at all. "I don't care if your mother is at the table, Cissy, get you little ass over there or you'll be working in my brothel within the hour! Besides, I am sure that they will not recognize you!"

With my heart in my throat, I sashayed over to the table and curtsied. As instructed, I blurted out, "Good evening ladies and gentlemen, my name is Cissy. I am your waitress for the evening and will serve you any way that you wish. May I serve you a cocktail?" My boss's secretary, Linda, looked at me in a funny way, as if she had discovered who I was, but they all looked at me in amusement as I stood there before them. I was a nervous wreck as I took their drink order and returned to serve them.

As they all toasted each other, Linda looked at me with a gleam in her eye and beckoned me to her side. She reached behind her and undid the black ribbon that was holding her long blonde hair in a ponytail, as she shook her hair loose she lifted up my skirt and petticoats, and tied the ribbon around my penis in a big bow. The entire table went hysterical at my humiliation. The next thing I knew, Linda had me kneeling in front of my boss, and had restrained my wrists to his chair legs. She reached over and undid his fly and started slowly stroking and pumping his cock, just inches from my face.

I looked up and they were all watching the action through the glass table top. Linda continued to slowly stroke his cock and ordered me to lick and suck on his balls. As she continued to slowly pump him, she ordered me to take each ball slowly in my mouth and gently suck on it. I could tell that he was getting extremely excited as he began to slowly grind against my face as Linda continued to masturbate him. Out of the corner of my eye, I became aware the each of the other ladies was doing the exact same thing to the males next to them- they were all being jerked off while I knelt under the table.

All of a sudden, Linda reached down and unfastened my wrists. "Okay Cissy, let's see you crawl around and worship the other three guys balls. I like the way you look when you do that!" Still on my knees, under the table, I crawled past Linda to the next cock that was being pumped, and started sucking on his balls. As I was working on him, I felt something invading me from the other end! It didn't take long for me to realize that the woman sitting across from the man I was now working on, had penetrated me with her high heel! Watching the action through the glass, everyone cheered at her creativity.

Using her heel like a handle, she suddenly pushed me to the next man, and withdrew her heel. As I started working on him, I felt another heel invade me. "Oh Cissy," Linda said in a very sultry voice, "I find this fascinating to watch a sissy boy get it in both ends. Hope you like the feel of my shoe!" With that she used her heel to force me over the fourth man in the group. Again another set of balls in my mouth and another heel up my ass!

All of sudden, one of the other girls said, "I think we need another drink. Besides, we don't want the guys to cum yet, we have to save them for whichever slave we buy tonight!" I crawled out from under the table and stood up. "Get us another round of drinks, Cissy. Perhaps we will make use of you later."

I went off to refresh their drinks, came back and served them. Linda still kept staring at me with an inquiring look in her eyes. I quickly averted her eyes, served them their drinks. I spent the next 45 minutes waiting on my two tables. As I passed Robert, I noticed that the lady whom Jennifer had given the guest card to, had arrived with her husband. She requested me for her waitress and before long; I had served them drinks and again spent time on my knees, under the table, orally servicing both her and her husband. As I arose Jennifer and Holly signalled me to serve them drinks.

As I was serving them, Jennifer turned to me and said, "Make sure you take care of your tables during the floor show and I want you to check your makeup regularly! You are to report back to me right after the last act and we will help Mistress Victoria get you ready for the slave auction. We wish to get a good price for your talents and all the trouble we have gone to!" I curtsied to Jennifer and went off to continue serving my three tables.

The floorshow began and the night progressed. During the show I received two more tables to wait on, in addition to the three I already had. One table consisted of three very dominant women, dressed in leather, who had me lean over their table while they changed the colour of my ass to a bright pink and penetrated me with a large dildo. The other table consisted of 6 European businessmen who made me suck each of them off, while they watched the floor show. Evidently my services were satisfactory to everyone, as twenty dollar bills were being stuffed in the top of my corset and loads of cum were being deposited in my mouth.

Before the last act had finished, I had received at least 8 loads of hot cum in my mouth and on my face, I felt totally abused and humiliated. Of course, the other waitresses really enjoyed seeing me subjugated and continued taunting me. "Oh Cissy, we can't wait to see what happens when you are auctioned off!"

I went to the employee lounge to freshen up my makeup, and there we three very attractive young ladies, dressed in various costumes. One girl was dressed in the diaphanous costume of a harem princess, another in a mini-bridal gown, while the third was dressed as a cheerleader. I was informed that they were there for the slave auction, also. They were chatting excitedly, discussing how much money they felt they would make tonight, and how much fun they were going to have, doing it.

As they were talking, Mistress Victoria introduced me to them and told them I was going to be on the auction block as well. They all thought that this was hilarious, and started telling me in detail some of things that they had undergone in previous slave auctions. I cringed, hearing the details and was become more and more apprehensive. The girls then started discussing how I should be costumed and within minutes I had been stripped naked!

A white satin corset was laced around my torso, then pink lacy stockings, pink crotchless panties and a pink lacy bra. Next came layers of pink and white petticoats. The girls had me sit down and they put little black "Mary Jane" shoes on my feet. I was made to stand while a pink taffeta party dress was lowered over my head. As the girls smoothed the VERY short flared skirt over the petticoats, Mistress Victoria placed a wide satin sash around my waist and tied in back in a large bow. Next came pink ribbons for my hair, and finally a pink ribbon around my neck.

As I looked in the mirror I saw a prostitute's travesty of a "little girl." By now, the other waitresses had all come in to see how I was being dressed for the auction. Their taunting became even more intense, and my embarrassment excruciating. As I stood there, tears brimming, Jennifer and Holly walked in. "Oh Cissy!" exclaimed Holly, "You are just too fetching for words. I am sure you will command a great price tonight!"