The Journey Pt. 04

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Josie becomes a woman.
7.1k words
4.69
12.2k
6

Part 4 of the 5 part series

Updated 06/08/2023
Created 07/04/2017
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The Salon

We lost Sophie that Friday, her debut performance was a bondage session, knowing Sophie she would have been a very happy girl after her first experience of real sex.

I was now senior girl, I had seen three other girls become senior, and then graduate to the salon's stage in my time. I knew the rhythm of the school now and it was merely a matter of weeks, no more than a month before my turn finally came.

Lucy had caught up with Charlotte, they were both in pastel blue panties now. At Mistress Anna's command, I had left them alone on, "I'm a boy Wednesday," and as she and Charlotte played with each other under the sheets, lust crushed Lucie's final internal barriers and she fully accepted her sissyhood.

Tomorrow would be my first day working the salon, I was scheduled to be on duty for only for a couple of hours after my day's lessons, but I was sure the experience would have me better prepared for my debut, and each night a little more money, my earnings for the evening, would be deposited into my boob job fund.

I knew silicon boobs cost out at only a few thousand each, I hadn't really considered having the operation back when I was a boy, but I had looked into the price to add detail and richness to my fantasy life, but at the Salon it would take nearly three hundred thousand dollars to cover the cost of my boob job.

I asked Mistress Anna why it was so expensive. She explained that any sissy could request silicon, but almost all the girls at the school preferred to wait to build up their account balance with wages and tips from working the salon and private clients until they could meet the steep price.

The boobs I would have were real, they wouldn't be something artificial, not quite true to the touch like silicon. They would be naturally grown inside me, my DNA already had the recipe for every part of womanhood included in it, all it needed was the proper catalyst to encourage a little rearrangement here and there and I would be one step closer to being a real woman.

I didn't ask the obvious question, "What else about my body could be rearranged?" I wasn't sure I was ready, or that I would ever be ready, to go down that road.

It would take less time than I imagined I was informed, as demand for quality sissysluts was high and customers were generous.

The school day passed as something of a blur, my teachers were aware of the reasons for my distraction and excitement, and made allowances for me this one time, even Mistress Bette smiled at me, and hardly brought any color to my ass when she caught me day dreaming.

Finally, Mistress Anna took me from class and through double smoked glass doors, a warning that we were now leaving, "Miss Philips's Academy for Young Women," had been sign written on to them.

We progressed down an unfamiliar corridor, the floors were black marble and the familiar click of our heels as we walked in unison down it was reassuring. The walls were off white, crowded with art work, original paintings interspersed with photographic portraits of women during sex.

Mistress Anna stopped before one and pointed, "My graduation dance," she laughed, she was bent at waist leaning forward, her hair was pulled back to show her face deep in concentration and pleasure, I could see rivets of sweat running down it, while behind her a tall man grinned hugely.

She took my hand, "It won't be too much longer before your picture graces these walls, Josie." I could only smile in return.

After a short walk, we came to a door with the dark green sixty-nining sissies logo of the salon above the words, "Dressing Room" in pink. Mistress Anna opened it, and we entered.

Jamie was on slut shift tonight, she smiled when she saw me coming through the door and hurried over to greet me, "Josie it's so good to see you, come sit by my station."

We walked over to a mirrored wall, every few feet there was a comfortable seat and I took the one on her right-hand side. Makeup and hair styling products were lined up before us, blow dryers, rollers, crimpers, everything a girl needed to make her look her best before a shift.

We caught up on gossip as she helped me select and fit waitress's clothes for the evening from a long rack behind us. I was a little disappointed as I looked around the room, I couldn't see Chrissie, and if she was working the floor she would be too busy to talk to me.

I laughed at myself, was I really that nervous. I knew that if Chrissie had seen me come through the door her tongue would have been down my throat before my heels clicked three times on the floor.

I put on the fresh white toga we had selected, it was just short enough that a tantalizing peak of my ass showed as I walked, there was a soft belt around my waist, tied in a knot which could be easily undone when a customer wanted a closer look at what I had to offer. Black six inch heels, dark hold up stockings, and a silky thin purple brief and bra set completed the outfit.

As I was on first shift I would have to be in place for the doors opening, Jamie told me it wouldn't be too busy at first, and I should have plenty of time to get my bearings and get used to the rhythm of the place before it got crowded, then a buzzer sounded and Jamie took my hand and led me out on the floor.

The Maître D'hôtel inspected each of us then released us to our assigned positions.

I would be working six tables, thirteen through eighteen, each girl placed her order with a single barman, and each barman served three girls.

My barman was named Carl, he was young and handsome and very good at his job, he gave me quiet instructions on how to place and pick up an order the way he liked it done, what to do if there was a customer complaint, or a customer got out of control. He made me repeat each of his instruction to be sure I understood them.

One of the perks of his job was free use of the girls, his final instruction to me was to kneel and before I had taken my first customer order his spunk had decorated my face.

That night passed quickly and very busily, word got around a new girl was on the floor and my tables were soon being requested by arriving patrons, although, given the way the night ended, some must have been a little disappointed when I didn't turn up.

My first order was from a group of IT executives at table fourteen. Four of them, VP and CIO types, I had actually worked for one of them back when Joseph was struggling to understand his sexuality, but I doubted he would connect the smiling sissy Josie standing before them with a morose and depressed programmer named Joseph.

They ordered champagne, with instructions that I should keep the bottle filled for the night, and two girls, who they would take care of filling. While I had been waiting for their order, one had casually pulled my panties down to look at my ass.

"Will there be anything else sir?"

The one gazing at my ass said, "No, that's all, for now, girl." Then he and a friend simultaneously landed a hard slap on either butt cheek, I gave them a girlie squeal, reset my panties and swished off to pick up their order.

I brought a chiller filled with ice and set it to the side of the table, I placed a silver tray with six glasses in the middle as requested and as I leaned over, not unexpectedly, my ass was groped again. I opened the champagne, filled the glasses and put the large bottle in the chiller.

A folded hundred dollar bill was slipped into the waist band of my panties just as two girls arrived, I didn't know either so I gave them a little smile and moved on to my next customer.

Table fifteen was a four seater with a single guy sitting there, he brusquely ordered a beer, and said nothing else. Tables sixteen and seventeen were still empty. A hostess was seating a group at table eighteen, I had been instructed to let customers settle before approaching unless signaled to approach.

As made my rounds, I overheard the Maître D say, "Might I suggest table thirteen, there is a new girl working it tonight, Josie, she's quite lovely."

My smile widened considerably.

Back at fourteen, the two girls were now naked except for their stocking and heels and bent over chairs facing each other. I watched as each took the head of a double ended dildo into their mouth, each cockhead had a blue line which they wrapped their lips around and there was a thin Red line drawn in the center of mass.

Behind each a gentleman stood with his erect cock in his hand, "Race," one of the other called and they started to enthusiastically fuck their girl, their goal was to push the line all the way into one of the girl's mouths.

I stopped for a second, fascinated by the groans and moans, the smell of champagne and sex, a loud cheer came from the table as with a huge thrust the contest was won. I checked the champagne, three-quarters empty and sashayed off to fetch another.

Table eighteen preferred their own regular waitress, it would be taken out of my rotation, but I would receive a small share of the tips anyway.

Table thirteen looked ready now, ten distinguished looking middle age Asian gentlemen, all dressed in gray business suits, white shirts, and black ties, sat, five at each side of the table, all were smoking while talking quietly.

I approached from the bottom left as was protocol. "Good evening Master, my name is Josie, I will be your waitress tonight, what will you have?"

The Man beckoned me closer, opened my toga and looked me up and down while stroking my sissyclit, "Single malt whiskey, water back," he handed me the token which allowed him to use me, "and oral satisfaction."

I received the same order from each of the other nine.

I rushed to grab Carl's attention, I gave him their drinks order and the tokens, as he filled the glasses he told me not to worry, girls would cover my other tables while I was busy. I hadn't been worrying about my other customers up until then, I'd been worrying about the mechanics of satisfying only that one table, thanks, Carl.

I returned to the table, I was very nervous as I served each of the gentlemen their drink and returned to the first position. I didn't have time to say anything before I was commanded, "Strip, naked, leave the heels."

The words of command galvanized my resolve, I quickly left my toga and underwear on the floor before replacing my shoes, then I knelt between his legs, unzipped him, and gently removed his cock.

For a few moments my hand worked some more hardness into him, and then my mouth went to work.

He paid me almost no attention, talking to his friends and sipping whiskey. I was using every trick I knew as I gazed lovingly up at the customer I was trying to satisfy, occasionally his hand would stroke my neck, but I saw no other sign he was enjoying my efforts, finally, he pulled my face back, "Eyes open," he said, and a rush of spunk shot out to cover my face.

He threw a hundred dollars on top of my toga as the customer beside him instructed, "Do not clean up."

His cock was already out and hard as I approached and he roughly pushed my head down onto it, he grabbed my hair frequently as he barked instructions at me, while another waitress brought them their next round of drinks.

"Now my balls.

"Just the head.

"Take it all in."

I made my way slowly around the table, the least amount of time I had spent on any of them so far was fifteen minutes, others had taken much longer. The only pause in my round was the customer who held my nose and poured some cool fresh water down my gullet before he followed it with another measure of hot spunk soon after.

I finished the last of the ten an hour after my shift had officially ended, each had casually thrown a hundred dollar bill to the floor as I finished their blow job, and after I had dressed each approached me bowed and stuffed another hundred into my panties.

I was exhausted as Mistress Anna led me back onto school grounds, "Did you enjoy yourself, dear?"

"Oh, yes Mistress," I replied, my voice weak and slightly harsh from my efforts, "it was better than I ever imagined."

I thought Mistress might like a good night suck, but she just led me to the shower room, "See you soon Josie," she patted my ass and walked away.

I could hardly stand in the shower, the other girls helped me get cleaned up and we returned to our dorm room, I almost fainted when I saw the black silk teddy laid out on my bed.

Graduation

I quickly changed as the twins nattered around me, this was too early, I had expected to be in school for at least another two weeks, probably a month. I thought I would sit with Mistress Anna again, in the TV lounge watching my personalized website show the bidding on my boypussies virginity, the way my mouths had been sold not so long ago.

For some reason my auction must have been held as I was working the salon this evening, but why?

I was tired and confused, I had waited for this moment, and now I was scared that I didn't want it, couldn't handle it, not right now.

The dorm room's door opened, Mistress Anna stood in the doorway in a classic little black dress, split to the hip, and full of promise. She held out her arm to me, "Josephine."

"Don't worry dear, I know you're exhausted," she said as we walked down the corridor, "a little visit to the doctor first, I think."

I am not sure what was in the shot the doctor gave me, but I came out of his examination room like a year old filly on her first appearance at Saratoga.

We made our way to the Head Mistresses office, she congratulated me on my graduation, mentioned how sexy I looked in my, "Gown," and after explaining that I could never go back to the dorm ever again, gave me a key to a room in the salon's residence.

I managed to stammer out, "I have a question ma'am, two questions actually, am I ready, and when was my auction?"

'Do you think I would allow you to graduate if you were not ready?" She looked at me rather sternly, "of course not dear, in fact, you passed your final exam on the floor of the salon tonight."

It must have had my head buried cotton wool, I recalled the other girls had only graduated after a blow job session with multiple partners, of course, it wasn't usually their first session, then again, first sessions were rarely with ten partners.

She paused, "you were not auctioned dear, a special request, along with a generous gratuity, was made by some very important customers, you met them earlier tonight, on this occasion, I decided that you were up to the task, and agreed.

"If you were not ready, I would not have agreed, and right now you would be lying in your bed watching the evening retrospective as usual."

She told me to trust her, not to worry so, and that I should enjoy myself tonight, it would be amazing.

Mistress Anna guided me around the Salon to the door which led to the back of the stage, the thick black curtain was drawn, muffling the sounds from the floor and the scent of alcohol and sex. She held me close, told me how proud of me she was, and asked for my room number and permission to visit me.

I laughed, "Oh yes Mistress, anytime."

I was so happy, my anxiety had fled as she held me close, I winked at her and made my way to the king size bed tilted toward the Salon at the front of the stage. I took a deep breath and nodded to Mistress Anna, and she stepped out of the stage area.

I lay reclined at ease on the bed, the MCs voice boomed across the room, "Ladies and gentlemen, tonight we have a very special performance, from a very special girl. In her debut appearance on the stage of the salon, please show your appreciation for Josie."

The curtains opened to a round of raucous applause, as I looked out at the salon, I could see the Asian gentlemen, had moved to occupy stage front tables, but all of the tables near the stage looked busy. I continued my breathing exercise, not wanting to give myself over to stage fright, closed my eyes and waited.

I didn't have to wait long, I heard the stage door open behind me, the audience below cheered, some laughed, some stood and clapped. My nerves rose but I didn't turn around, I knew my virginity would soon be a thing of the past, that was the reason I was lying here after all, but I remembered Chrissie's show and I was nervous about how it would be taken.

I heard the sound of high heels on the floor behind me, a slow click, click, click, so it was to be a woman.

A master performer approached me, each slow click on the stage heightened my nerves till they rang like a chorus of church bells on Christmas morning, my senses heightened in proportion to my nerves and I could smell her subtle scent, lavender.

One slow step after another, I stopped counting at eight, my sissyclit was raging, my boypussy was soaked, my nipples hard, I was vibrating like a guitar string. I could sense her standing immediately behind me, a soft manicured hand rested itself on my shoulder, any touch of uncertainty vanished, I was ready, I wanted this, then Chrissie's voice gently said, "Ready my love?"

I screamed with pleasure, my back arched as my head rounded back to see her, I orgasmed shooting my hot sissyspunk all over the inside of my teddy top, somehow through the torrent of desire engulfing me I heard the hoots of encouragement from the audience below.

She walked around the bed to stand at its right-hand side, she was wearing a matching black teddy, well almost matching, hers had not been recently soiled, she was not, however, wearing a matching expression of absolute shock.

She smiled at me as she stripped, throwing her teddy down into the audience to land on the table where the Asian gentlemen sat, she had never looked more lovely and I had never been more in love.

Her sissyclit was enormous, I had held it in my hands on many Wednesdays, but I didn't recall it being quite so large, the skin straining like a taught drum around its flesh, her body was delicious, and she turned to give the audience a complete view of her, her ass was high and haughty, her blonde hair reached down her back to almost caress it and he pretty face shone under the spotlights, how had I ever found such a wonderful creature?

She joined me on the bed, and started to seduce me, she kissed my neck, my mouth, she moved up and down my teddied body, her hands, her lips, her eyes caressed me and I began to drown in a whirlpool of happiness.

She lay beside me, and then pushed my head down her body, I reached her massive sissyclit, stopping only to give thanks for what I was about to receive then hungrily devoured it.

My head bobbed up and down, my mouth gaped and my throat happily accepted what was thrust into it. As I reached the bottom and had taken her all in, Chrissie's hand slapped my ass, like the drummer on a slave galley she beat time, the beat increased until it was frantic, at last grabbing my hair, she stood pulling me to my knees then to cheers from the floor she shot her sissy spunk all over my face.

"That was great honey," she said as we lay back down and her arms wrapped around me, "but it was only the appetizer, are you ready?"

I answered her with a gentle bite on her shoulder, she laughed and efficiently stripped me. My Teddy landed close to hers, another prize for our sponsors. She put me in the doggy position, turning me around so the audience could have a good view of the butt plug being removed, it too was thrown away as a trophy.

She whispered to me, "You'll have so much cock wanting you, you won't ever need a plug again" she moved behind me and started to tongue my boypussy, the sensory overload was too much, I couldn't control myself and I shot again, all over the bed sheets this time, the audience cheered.

She turned me on my back smiling at me, her hands played with my sissyclit as she kissed me, she started to finger my boypussy, quickly she had three fingers inside me warming me up for the main event, I arched my back as she left a bite mark on my tit, "It's time," I managed to growl.

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