The Journey Pt. 02

The Third Room.

The Third room was a dormitory. On either side of the door was a line of four beds, the last two on each side were made up. These were soft feminine beds and bedding, not hard army bunks like school dorms have on TV. Between each bed was a chest of drawers, four drawers deep, each labeled from the top down; Bras and Panties, Nightwear, Toys, Heels. Above each bed was a large flat screen TV, and between the bed and TV a name plate, White plastic with Pink lettering, Chrissie, Jamie, Sophie and finally Josie.

I wandered over to what I knew would be my bed, I itched to open the drawers but my inner voice advised against it. There was a cork pin board above my chest of drawers, empty. I looked around, the other girl's boards had various pin-ups on them, mostly young hunks with big erect cocks, but the odd naked woman was mixed amongst them.

The door at the other end of the dormitory opened and three young ladies came in, each was dressed in a nighty of a different color, although flat chested they were showing the curves of womanhood to varying degrees, they wore high heels which did their job well, shaping the curves of their leg and lifting their enticing butts high.

With a not quite genuinely feminine squeal, they rushed to hug me. Chrissie dressed in pastel Blue performed the introductions, she pointed to Jamie in fetching Yellow, Sophie was garbed in a light Pink, "Welcome to school," she said, "Girls, let's get Josie sorted before bed."

They took me to the shower; I came out with no body hair, smelling of my favorite scent, Lavender. Each girl had shaved and washed a little of my body, explaining it was a bonding experience, as senior girl Chrissie shaved my around my cock and ass, she explained as she did that I could never against speak of having a cock again, I had a sissyclit and a boypussy.

When we returned to the room I found a canvas bag upon my bed, we all happily rushed to open it. The first item that came out was a bag from Victoria's Secret, bra and panty sets, each was white. Chrissie explained that color was a sign of achievement, white was for fresher's like me through to Black which a girl only wore on the night of her graduation.

We opened the first drawer and stored them away. The second bag had pajamas, teddies, night dresses, I laid a white teddy set on the bed and carefully stored the rest. The other girls dressed me in my nightwear, more bonding.

There was some lube and a very small butt plug in the box labeled toys, nothing else. It was explained that more toys would come as rewards for achievements earned in class. Finally two shoe boxes, each contained a pair of heels, one two inches high, the other three. I looked to Chrissie wearing six-inch monsters and needed no explanation.

A voice came over the intercom telling us it was time for bed. We kissed each other, I thought it would be on the cheeks like in the movies but Chrissie as the senior girl came to me first, her lips met mine, and her tongue pushed my teeth open as she frenched me, another first. Jamie and Sophie after finishing with each other then came over and frenched me too.

I had never really been kissed before, certainly not deeply, and in the space of a few minutes I had made out with three different girls, I didn't think it was possible after the day I had, but I felt my sissyclit harden under the White Satin.

We each got under our quilts, mine like everything else I now owned was plain white, I noticed that no girls hands were above the cover, mine was slowly rubbing my engorged sissyclit. The lights dimmed but did not go out and the TVs came on. The first show was me, standing naked beside Mistress Bette frantically rubbing my sissyclit for all I was worth. Jamie was next, leaning over an unknown Mistresses knee, her panties at her ankles as a belt landed upon her raised ass; she called out each stroke and thanked the mistress for it. Sophie was naked, in a gym receiving praise from an instructor as her leg spread eagled to the side and her boypussy touched the floor without an inch of space between them.

Then Chrissie came into view, she was dressed in a school girl uniform, the blouse was tied up to give her the semblance of tits, and the tartan skirt was so short it was easy to see her panties curve around her lovely ass. As she got on her knees the camera panned out to show a man unzipping his trousers to bring his cock out, gazing lovingly up at him the whole time, her mouth was working his cock for all she worth, the unknown man grabbed her hair, pulled her face back and shot a load over her pretty face. From the beds beside me, I heard groans as girls found release.

So each night would end with a retrospective of the day's lessons, I smiled as I hoped my performance would make my girlfriends cum the way Chrissie had just done.

Then the scenes changed, scene after scene showed girls with real pussies and boypussies being fucked in every position, the final scene was a girl on a stage, dressed in a black, a naked man with an erect cock approached her, he undid her silk kimono, gazing down at her as he forced her to her knees to accept his cock.

She sucked on him enthusiastically for a few minutes, before he dragged her up by the hair, pushed her over a seat so her face was to the audience, he ripped her panties at the right and left side, and held the tattered garment aloft, he threw them to the audience below, then stepping behind the girl he pushed his cock deep into her boypussy, her head reared in pain as she lost her virginity, then slowly pleasure transformed her face as behind her, thrust after thrust opened her into joys of womanhood.

From the side, a low whisper told me, "That's Melanie. She graduated today."

My first day.

The intercom announced it was time to wake, the TVs came on, new scenes of Melanie being fucked came through, the girl may have lost her virginity just the evening before, but it looked like the only thing she has rested on during the night, had been a hard cock or strap on. Man followed woman, taking her in various positions, the final scene showed her with a cock thrusting up her boypussy, while to the front her face was being well fucked too.

The covers were shaking again as each girl rubbed herself to completion, the TV went off and we got out of bed. Performing the kissing ritual again and although I had just come in the teddy bottoms, I could feel my sissyclit harden as each girl forced her tongue into me once more.

We headed to the showers, stripping off the soiled underwear and left it in a basket at the end of the room. Chrissie washed me, then I washed her, and Jamie and Sophie did the same. We returned to the room to find clothes laid out on the bed for each us.

I had a school girl uniform, red tartan skirt, white shirt, white panties; my two-inch heels were also laid out. We dressed quickly and silently, and then waited at the foot of our beds. After a few minutes, the door opened and four Mistresses and Masters entered the room. Mistress Anna smiled at me, "Josephine. Welcome to school, please come with me."

Mistress Anna was dressed in the same style of black leather outfit that Mistress Bette had been wearing the day before, as I followed behind her, wobbling unsurely on my heels, my eyes were drawn to her ass, it was high, tight, and perfect, she opened a door and I stepped into a new room.

One side of the room was taken up by a yoga mat laid out in front of a TV; the other side had a Treadmill.

"For your first week, you will do only exercises designed to increase your femininity, to shape your body, to teach you how to act like a lady." Mistress Anna quickly recited a speech she obviously knew by heart, "In the morning you will do one hour of Brazil Beach Butt Lift, one hour on the treadmill in heels, one hour of stretching and one hour of deportment."

She continued, "In the afternoon Mistress Bette will take you to Medical, after that you will rest on top of your bed until your sisters return. Do you understand?"

I had never tried to talk like a girl before, in my fantasies, of course, my voice was sexually feminine, "Yes Mistress Anna." I heard my unconvincing warble.

I hear her gentle laugh, "Very good Josephine, please change into the leotard and I will start your instructional videos."

My first morning flew by, it was exciting and painful, Mistress Anna encouraged me through every step, coaching me continually, somehow without noticing the passage of time, it was afternoon and I was lying naked on top of an examining table in a doctors surgery.

The Door opened and a man in a white coat entered, "Stand and face me," he said I did, and he took a photo of me. "Turn round." "Bend over." "Spread your legs." "Kneel." as I hesitatingly followed each command, another photo was taken.

"Don't worry, I like to record my work before and after, did you see Melanie's performance last night?"

"Yes, Sir." I Croaked.

"Doctor, call me Doctor, well Melanie was one of mine, as shall you be dear." The Doctor never gave me his name, not then, not ever, but he explained his regime to me.

I would receive injections into my sissyclit, the idea was not only to lengthen and widen it but to keep it hard for long periods of time, the final goal was to have it last for 8 hours. My metabolism would be enhanced, I would be able to cum not once or twice a day, but at will almost indefinitely. My body would be shaped, hips widened, ribs altered, if necessary a butt lift, facial reconstruction, if earned it, a boob job. It had been decided I was not a candidate for a full pussy replacement but short of that, I would end up being as close to a real woman as was possible.

The Doctor looked at Mistress Anna, "Have you decided on hair color?"

"Redhead." she said.

He shaved my head and then covered it with a salve, "This will give you hair that looks and acts more like a girls, it will grow a few inches a day." he took a template and gave me a nice little runway above my sissyclit too. So I was to be a Redhead, I liked it.

Finally, I lay on the table, the Doctor held my sissyclit, the first man's hand on it other than mine ever, but the needle he quickly shoved into it, killed any excitement that thought may have brought, the pain was intense and I passed out. I woke on my bed as the other girls returned to our dorm sharing the day's gossip.

Chrissie quickly came to my bed, "You poor thing," she said, the first day is always the worst with the Doctor." She lay down beside me and drew me to her, "It gets much better, and you will like what he can do for you." She took her panties off and put them on my dresser, she lifted her skimpy skirt and I gazed at her erect sissyclit, it must have been at least 12 inches in length, and if anything it was disproportionally wide, "See." she smiled at me.

I lay in her arms, comforted, the other girls drifted our way as well and I gradually returned to full consciousness our day ended as yesterdays had, shower, bed, video. Coming back from the shower we saw a canvas bag on Chrissie's bed and rushed to it, she took out the panties, a deeper Blue than she had worn yesterday. We watched the days review, anticipating, When Chrissie came on screen she was on her knees, 4 men around her, her mouth took each of their cocks, in turn, some took a blow job and let her finish them, some had less control and face fucked her for their climax, at the end her face was painted with Spunk. I think all 4 of us came simultaneously; our hands furiously rubbing our sissyclits below the covers as we watched her, and climaxing as she softly laughed, "War Paint."

Day Five

It was the Wednesday of my first week at the school, in the showers as Chrissie gently washed me down, she warned me not to masturbate during the evening videos. It was the first time any of the girls had admitted what we did each night under the moving covers as we watched each other on the screens above our beds learn more and more about sexual womanhood. I nodded yes, then turned to soap her delicious butt down, I so wanted to touch it sexually, so wanted to kiss it, I'm sure she knew but she never gave me permission.

It was so difficult to watch that nights videos, my sissyclit was rock hard, but I kept my hands on top of the duvet, I noticed each of the other girls doing the same, the TV went out, the lights dimmed, and I watched as Chrissie left her bed and crossed the aisle to mine. At her nod, I moved over and her hand reached to take an edge and lift the covers, she stripped and left her gown on the floor, her sissyclit was hard too and pointing forward at me, she smiled again, and my night gown was thrown over her head to land on top of hers.

She joined me under the cover and I lay back as her tongue sought my mouth, I could feel my legs involuntary spread, her eyes laughed, her hand reached down to mine and moved it over her sissyclit, the same hand then grasped my sissyclit, and I exhaled.

'Gently Josephine," her breath was light and warm, "Let me explain."

"Men will pay for firsts, to be the first to have your mouth, the first to have your boypussy, the first to whip you until you beg for forgiveness, but they won't pay for the first wank. The owners have tried, but it's just not a seller. So one night a week, unofficially after the light go down, we are allowed to please each other, but there is a price."

Our hands were moving gently along each other's sissyclit, "The reason they allow this, is so you are not cock shy why it comes time for your first blow job, many gentlemen want their blow jobs to last, and so they demand a wank to get rid of their first load of cum beforehand, they almost always want you to point your cock at their eyes as they shoot their load, and the sight of a cum covered face seems to excite them more, do you understand?"

"Hmmmm." I moaned.

Her hand stopped mine, "The price is full honesty, for tonight only, you must admit that you have a man's cock in your hand, and a man's hand on your cock before we go on, you must tell me what you are holding."

"I'm holding your cock Chrissie, please let me get you off, I want you to spread my legs, get between them, and as my hand touches you, cum on my belly like the gay slut I am." It had been hard to admit to myself all my life, but not hard to say to Chrissie, as I reflected on this moment much later in life, I realized how important it was in fully accepting my sissy-hood.

Her mouth covered mine, our hands moved in unison, from the side I could hear Jamie and Sophie's passion too, we drove each other to simultaneous orgasm and collapsed. In the morning I woke with Chrissie sissyclit pressed into the gap of my butt, her arms spooned me, and there was no doubt who was the top in this relationship.

After our shower I saw a bag at the foot of my bed, I had earned my yellow panties.

Week Three

It was my third week of school, as I took to my lessons I had discarded white panties and pale yellow, now I was wearing a deep yellow boarding on Orange. Chrissie was now in deep purple lingerie and would soon be ready for graduation, I would miss her badly, she had helped me so much, and I had fallen in love with her.

We waited at the foot of our beds dressed for the day, the door opened as usual, and I heard Mistress Bette's voice call, "Josephine." I had not seen Mistress Bette since that first day, and my sissyclit tightened at the memory.

I followed her to a new room, inside was a wide bed, a single black silk sheet covered it. Mistress Bette walked over to the corner, lifted an open bottle of champagne and poured two glasses. "Come, dear," she said, "drink with me."

I sipped the champagne as the videos had taught me, she smiled and came close. She took the wine glass from my hand and placed it on the table, when her hand returned, it was on my left butt cheek, she squeezed and pulled me close to her, I looked up to meet hungry eyes and leaned forward for her tongue to explore my mouth.

She pulled me over but didn't drop me on the bed, she moved to relax on the pillows and invited me to join her, I willingly lay beside her and her hands and tongue took their pleasure of my body. My sissyclit was hard again, we had never discussed Lesbian Sex in school, although I had seen other girls in the nightly review being used by a woman, and I should have known this was coming.

Mistress Bette instructed me on how to open the straps I'd have never noticed on the gusset of the leather pants, I slowly undid them and saw my first real life pussy, it's pink lips spectacular against the ochre hew of her Asian skin, and I was Green with jealousy, for I would never have anything like it.

I was taught to use my tongue on her clit, in her pussy, in her asshole, she came freely as my tongue learned its lessons, my sissyclit stayed firmly erect, but anytime I thought I was close to coming, she would reach down, grasp my sissyclit at its base, squeeze, and her hand would magically stop the process. Three hours passed and finally, Mistress dragged me into her arms, "Enough darling, enough."

She gazed down at my erect sissyclit; a shared memory must have exchanged between us for she leered at me and once again I ended up kneeling in front of her cleaning my sissy spunk from the floor with my tongue.

Week Four

It was Friday night at the end of Week Four, and I was now wearing solid Red panties, we returned from the shower to see that Chrissie's name plate had been taken down, on the bed a Jet Black Bra and Panty set was laid out, it was the lacy type that Chrissie preferred, we gasped at the sight of her graduation gown, then we rushed to hug her, crying and laughing.

Chrissie had been my mentor, she was the only man who had ever touched my cock, although as a girl she had never touched my sissyclit, I cried with sadness because I would miss her so, and I cried with gladness at her blossoming womanhood.

She pulled her close to me and bent her head as her tongue searched for mine, as always I let her take charge and I felt my sissyclit, now somewhat larger than when I had first arrived in the dorm room, engorge. She whispered to me, "When you watch me taken tonight, cum hard for me my love." I nodded, "I'll see you on the Saloon floor soon enough, you're a quick study Josie, and you'll start Blow Job training at least a week before I did."

The tradition was that the person who had first introduced you to the school, was your escort to your graduation ball, I knew Mistress Anna would be my date, our door opened and Master James came in wearing an expensive Tuxedo, he held out his arm to Chrissie, and I watched that sexy ass sashay out of our dorm room for the last time.

And then we were three, I cried a little and the other girls did their best to comfort me, I don't remember much as I lay watching the TV with anticipation, longing to see Chrissie again, waiting for her to appear on the stage that we all knew was our eventual destination, and which I had last seen when Melanie graced it those long weeks ago.

The audience applauded as the curtain was drawn back, and Chrissie naked except for her lacy panties was displayed at the front of the stage in a contraption I had never seen before. She was three feet off the floor, arms and legs tied into some type of fuck swing, ready to be positioned into which ever position the man who had won the auction for her virginity desired.

She was the person I had grown closest to in my entire life, I knew her well, I could see the fear, the longing, the want in her eye, then from the back, hidden to her view a fat man, as wide as he was tall, walked out. His cock was a monster, but his belly was so huge I doubted he'd seen it in years.