The Journey Pt. 03

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Josie gets deeper in to sissyhood.
5.4k words
4.7
13.8k
8

Part 3 of the 5 part series

Updated 06/08/2023
Created 07/04/2017
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Training

It was an unusual feeling walking down the corridor, my sissyclit was hard with excitement and I had not yet adjusted to the feeling of the butt plug placed firmly in my boypussy.

I still tried to move in a ladylike fashion, but the strange sensation was overwhelming and I stumbled suddenly out of time with Mistress Anna's gait.

Mistress Anna opened the door to our usual class room, a table had been added to the furniture inside, and on top of it, I saw a selection of dildos and vibrators.

"Do you recognize them slut."

"Yes, Mistress Anna, it's my collection from home."

Mistress Anna did something she had never done before, she stood behind me and her hands slipped under the band of my boyshorts, she caressed my ass cheeks, as her hand explored my ass, she would occasionally let a little light tap fall on the end of the butt plug.

Every time she did, I let out a feminine squeal of delight.

I could see myself in the mirrored wall, eyes hooded, smile broad, I had never been happier.

"That's right my Josephine, it's the ones you selected.

"They are good enough for starter classes, you know you never practiced with them properly anyway dear.

"I will remedy that."

She withdrew her hand, and walked over to the table, she selected the smallest of my dildos, little more five inches long, and not much wider than a big man's thumb.

She slotted it into the front of her uniform, it looked like she had a real hard on, and she moved the dildo to ensure it had a cocks natural range of motion, the she started working on the rooms walls.

I stared at her, fascinated by the dildo swaying as she worked away.

Finally, the mirrored walls had been folded into an open triangle were someone in the center would have close to a three hundred and sixty-degree view of themselves.

She beckoned me forward and pointed to two white circles she had placed on the floor.

"Kneel," she said, "your knees go there," pointing to the circles.

I knelt in front of her, hungrily wanting to start my lessons, my mouth eager to feel a dildo in it again.

She slapped me across the face and my ears rang.

"Lazy bitch, kneel properly, do not rest on your heels unless a gentleman requests it, now raise your thighs up and adopt a proper posture."

Mistress Anna had never punishment me before, and I felt my tears respond not so much to the warmth her hand had laid on my cheek, but from my own sense of disappointment because I had forced her to discipline me.

I had lost self control in my eagerness and had gotten sloppy, I told myself it would not happen again.

The next hour was spent on kneeling practice, getting down gracefully, getting up gracefully, I forgot about the pleasure of the butt plug as my legs screamed in agony.

I received more than one stinging slap that day, and for the first time, I spent an entire lesson with tears touching my pretty face.

Mistress Anna taught me how to move the mirrored walls into place in the room for lessons and stow them properly at the end of the day.

"From now on this is your duty, as soon as you enter the class room, perform your curtsy and then build the wall into a viewer."

The intercom announced the end of the day's lessons.

"Would you like your butt plug removed dear."

I answered no.

"I knew you would say that," she laughed, "girls like you always do."

New Girls

We returned to the dorm one night to find two naked girls standing in front of us holding hands, obviously twins, the name on their side by side bunks read Charlotte and Lucy.

We gave high pitched squeals of delight as we rushed to welcome them, Jamie was now senior girl, and she took charge.

We got them showered, kissed goodnight, and tucked them in, just as the TV came on.

We watched as a new Master instructed Charlotte and Lucy, their hands reached out to the others sissyclit and excitedly moved up and down their hardness.

They came simultaneously, they were standing so close while they unreservedly whacked each other's sissyclits, their sissy spunk first hit their bellies, then dribbled to the floor.

Like the rest of us have during our initiations, they ended up on their knees cleaning the floor with their tongue, but first, they showed us their flexibility as they bent to lick the sissy spunk from their own bodies.

"We've watched each other before," Charlotte told me, "but we've never touched each other."

"The second room brings out the sissy in us all," I replied.

Twins were going to be an interesting experience, I had no one to share Wednesday nights with since Chrissie's graduation, should I pick one or both.

I would need to speak with Mistress Anna about that, to see if the school had any rules.

My skit that night was short, just the Head Mistress plugging me.

I hadn't realized there were so many cameras in the room, and one captured my expression as the roundness of my hole was penetrated for the first time, even though I knew it was coming, the expression was surprisingly, surprise.

Sophie by now was giving real blow jobs, and we watched as she attempted to stuff a stud's member down her willing gullet.

I don't think she successfully took more than half before her face was covered in his spunk.

He was obviously unhappy as his large hand came across her face and she landed on the floor. He walked away leaving a sobbing girl behind him.

We watched as six men in succession came to stand before Jamie's kneeling form, erect cocks waiting to be sucked.

Her head bobbed over them, her red lipstick left marks at the bottom of each shaft as she successfully negotiated their various needs, some made her swallow, one came on her hair.

At the end, she was an exhausted satisfied come drenched wench, and I knew she would be leaving us soon.

Continuation

My tutelage under Mistress Anna was my favorite part of the day, even more than satisfying my sissyclits needs under my flowery duvet while I watched the nightly TV show.

It was three days before she finally let my mouth cover any of the plastic cocks, she had her hands in my bold red hair, which now reached half way down my back, using the grip to allow me to take in only as much as she wanted me to.

It hurt, but I really didn't notice the pain in my eagerness.

I learned to caresses a man's cock with my right and left hand, how to run my tongue just under the helmet, or tickle the eye.

I learned to use my teeth.

I learned how to gradually accept its length, and how to accept it all in one smooth motion.

I learned the technique for using my tongue to give a client added satisfaction as their cock thrust in and out of my mouth.

I learned where my gag reflex was and how to ignore it.

I learned to see a cock with my peripheral vision while I constantly gazed up lovingly at its owner.

I learned to suck cock kneeling, lying down, bent over backward, tied from the ceiling with my head to the floor.

If there was a position in which you could imagine a man contorting my girly body to, so to could Mistress Anna.

I learned the protocol for accepting a line of waiting men, or a gaggle of them simultaneously.

I learned the tells that said a client wanted me to clean up, or stayed messed with spunk.

Not all of my training was physical, there were plenty of videos of other sissies enjoying themselves on real flesh.

As the weeks passed longer lengths and wider girths of dildo lay on the table, my own pathetic collection long since discarded and replaced by the school tools.

These were designed to simulate hot spunk shooting with force from a man's cock.

I learned the exact moment to blink to protect my eyes.

I spent at least two hours a day with one of those cocks in my mouth, frequently covered in simulated spunk, and I loved every minute of it.

Bound

Day followed day as Mistress Anna taught me the ways of cock sucking.

A Master named Jack was my position teacher. I spent hours practicing being fucked in the missionary position, raising my hips to the imaginary thrusts of a client.

Doggy, cowgirl, reverse cow girl, I had 20 positions to master perfectly before I would be allowed to graduate.

The Doctor was satisfied with my progress, my sissyclit had reached the proper proportions now, it could stay erect for 8 hours, and I could pour sissy spunk out of it like turning on a tap.

My figure was more feminine, perhaps a little exaggerated in places, but very obviously feminine, except for my flat chest.

My butt plug was continually expanded now it was the size of a real cock, a small cock maybe, just six inches, but closer to the reality I longed for.

I knew I was doing well, but I was worried, each night when we returned from the shower, no set of new panties was waiting for me.

I was still on the same pastel blue shade I had been wearing, when I had first taken Charlotte, then Lucy into my bed on "I'm a boy Wednesday."

I wasn't really worried about forming a bond with them the way I had with Chrissie, the two of them were obviously pair bonded for life, it was just a little fun.

Lucy was still a little hesitant, but Charlotte, oh Charlotte was different, and in our make out sessions, she gave me some of the best wanks I would ever experience.

Then came the day Mistress Bette lead me into a new room.

I was startled when I entered, this was a dungeon, hand cuffs, ropes, cages, whips, all were visible, at least three apparatus for which I had no idea of the function took up some of the space.

It seemed our nightly videos edited some things out after all, for I had not seen any of the other girls in bondage training before.

"Strip," Mistress Bette's voice was terse.

When I was naked she affixed a restraint onto my sissyclit. "In here, you come only if I decided you have earned it."

"You should get used to the feel of it Josephine, unless you are with a client, you will wear one every time you leave the building."

This was the first time my sissyclit had not been allowed to harden with excitement since I had started school, I was confused, and I had never considered that I might see the outside world again. In that one glance from the Head Mistresses office, it had looked so remote and no longer part of me.

Mistress dragged me by the hair into the center of the room, efficiently cuffed my hands and locked them into a hoist, using a remote control she raised me toward the ceiling until I was standing on tip toe, every muscle strained as I waited.

She stepped in front of me to lash a cane through the air.

"Call them out as they land girl."

Swish, agony spread across my butt as the cane landed perfectly across both cheeks.

I blinked a tear from my eyes and a weak feminine bleat whispered, "One, Mistress."

"Are you playing with me, Josephine?

"Do you call that pathetic effort calling them out?"

I couldn't speak, I shook my head trying to clear the tears from my eyes forcing out a still weak, "I'm sorry, Mistress."

Swish, Red agony rushed through my body again, my tears flowed free as I screamed, "Two, Mistress."

"That was almost satisfactory Josephine, but you got the number of lashes wrong."

The cane landed on my butt again, and again, and again.

I was told I would receive six strokes as a warm up, by the time the soles of my feet rested once more on the floor, thirteen distinct red stripes decorated my ass.

I was tied to the floor and my legs and arms stretched to lengthen my body.

Mistress approached me with a stiff riding crop, it lightly landed on my nipples, my fingers, my toes, my bound sissyclit was hit over and over again, as was the base of my butt plug, all the while Mistress derided me for my performance, telling me I was the most worthless sissy she had ever trained.

She stood over my face and I looked up at her lovely pussy, at her command my eyes and mouth were wide opened as I received my first Golden shower.

I was bent over a trestle, my hands tied around my ankles and my ass was abused again.

I was crammed into a dog cage and left to feel the agony as my body stiffened in its unnatural pose.

My face was repeatedly shoved into a full basin of cold water, I was held under until my heels began to kick.

A ten-inch dildo was shoved down my throat, then a full face mask covered me, Mistress laughingly pinched my nose, calling me a pathetic little girl as I strained against her hand.

Eventually, my world went dark and I passed out.

I woke on the hoist again, screaming in agony as a device which shot electric sparks landed on my sissyclit, my boypussy, my nipples, the soles of my feet, everywhere received treatment and I screamed in agony begging my Mistress to please forgive me and make it stop.

Time lost all meaning, all I knew was pain and the need to please my Mistress.

Minutes passed, nothing happened, no new abuse was heaped upon me, I called out for my Mistress but she did not respond.

I heard her heels walk up behind me, she released me from my bindings and turned me around.

I could see Mistress Bette was excited, she was as naked as I as she undid the restraint from my sissyclit, she smiled as taking me by the hand she led me over to the bed in the corner, and for the next 30 minutes, my pussy eating teacher received the rewards of her instruction.

When I returned from the shower that evening, a deeper blue set of clothes was laid out on my bed.

Auction

We lost Jamie to her graduation that Friday, we all masturbated furiously as we watched her virginity being taken by an older woman with a large strap on, that possibility had never occurred to us.

Sophie was now senior girl.

On Saturday I didn't go to class, rather I was taken to a room with racks of clothing and told to pick something that made me look my prettiest.

There was a nice floral summer dress, rather sheer, you could see my panties through it in the right light and when I turned it flew in the air to give just a glimpse of my very girly ass.

Mistress Anna came and explained this was a photo shoot, it was time for some glossy photos, my attentiveness and application in class had been noticed and as a reward, my oral virginity was being auctioned off today.

At last, a man with a real cock would take pleasure from me.

I knew in my heart I would satisfy whoever bid on me, and I smiled, pouted, stuck my tongue out, and willingly did everything else the photographer demanded.

Mistress Anna took me over to a computer to show me the auction as it went live, there was a full biography, men could view my recently taken glamor shots, and a few stills from other classes had been added, along with some short teasers videos of me sucking on dildos in training class.

As we watched the first bid of five hundred dollars was made.

Mistress took me to a waiting room, their was a TV running a live feed, it showed the stage where we gave up our anal virginity. The stage was empty just now, instead, the feed showed the entire room, not just the small section I had seen so far.

A bar ran across the screen showing the status of my auction, I was already up to nine hundred and ninety-nine dollars.

"That is the salon dear," Mistress Anna told me pointing to the TV, "it's where you girls repay us for the cost of your training."

The salon was a big room, at the back opposite the stage, a bar ran along the length of one wall. Spread around the room were tables of various sizes, some only had two seats, some could easily seat twenty or more.

The place wasn't full yet, and serving wenches hurried drinks orders to the customers, familiar pats landed on butts, tips were placed in panties, and everything seemed like a normal bar/strip club.

"The bidding on you is going very well my dear, I'm sure your auction will close soon, are you nervous?"

I turned to Mistress Anna, "A little Ma'am, I don't want to fail you."

It took me a few minutes to realize there was a lot of sex taking place in that room, one girl was being spit roasted over a table for two.

Another was on her back on top of one of the larger tables being savagely fucked while another four men, each with a waitress sucking their cock to maintain their erection, waited for their turn.

Everywhere I looked a slut was being fucked or a wench fondled.

One patron had his seat pushed far back from his table, I could see his smiling face, a wench had her legs spread across his lap and from her movements he was obviously deep inside her.

His hand played with her sissyclit, then panorama swung around and for the first time in weeks, I saw my beloved Chrissie's face beaming with pleasure as she rode the hard cock inside her.

I continued to watch the Saloon, perhaps an hour had passed, and Chrissie had serviced another two customers. The room was almost full now, few tables were empty, and the noise level was increasing.

With all the booze and the smoke and the fucking, I wondered what that room smelled like.

"Well Josephine, your 'Buy it now' bid was set at ten thousand, and that had just been offered, are you ready?"

"Yes, Mistress Anna," I replied.

First Customer

We moved to a new room, I don't really remember much about it, except it was expensively furnished.

I could hear the sounds of porn on the TV, and on the couch in the center sat a well-dressed man, he wore a charcoal gray two piece business suit, highly polished black leather shoes, a deep blue shirt, and pale yellow tie.

He was relaxed and smiling.

"This is Josephine," Mistress Anna announced, "she has never known the sexual embrace of a man, she presents herself for your pleasure."

I curtsied in front of him, "Welcome, Master."

His smile widened and he stood removing his suit jacket.

A light tap on my ass from Mistress Anna reminded me of my duties, and I hurried over to help him undress, my hands trembled just a little as I undid his belt and I held my breath as I removed his jockey shorts to see the erect cock of my first client.

It was a fine specimen eight inches in length, I could make out each of the throbbing purple veins against his pale skin, the head quivered in anticipation, oh yes, that would do very nicely.

He sat on the couch and opened his legs.

I reached to the strap of my dress ready to remove it, "No," he growled, I could sense the want and eagerness in his voice, and I quickly lowered myself to my knees.

He grabbed the back of my neck and pulled my mouth forward to kiss me, his tongue explored me, and I accepted him willingly, my mouth was his to use as he saw fit, he had paid for the privilege.

My hand reached to stroke his cock and underneath the light sundress, my hard sissyclit was obvious.

"Now," he said.

Keeping my eyes on him, I brought my head forward to his lap, my tongue reached out, I let it run around the eye.

Mistress Anna had warned me to start slowly my first time so as not to lose control.

I was glad she had, for I wanted to do nothing more than thrust my head over his shaft and feel his come.

I ran my tongue around the helmet, watching my salvia make it glisten, touched it gently around the lower edge, then up and down the shaft.

I took each of his balls into my mouth as one hand was playing with the shaft, then I returned my tongue back up the eight-inch length.

It was time.

I was in a state of delight I had never experienced before, this is what I had been born to do, opening my mouth I took the tip in.

I felt a little pre-come leak from the eye, the taste added sensation to my already overloaded senses, it was delicious, better than chocolate, slowly I began to bob my head, accepting a little more length each time.

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