Mistress de Sade's Sissy School

"You'll make me cum now, or I'll whip you black and blue," she screamed.

My nose was pressed to her belly, her cock was fully in my mouth and throat, I was gagging so much I thought I might puke. She must have loved the squeezing of her cock and the thought I could die whilst servicing her, hips thrust hard against me, my hands were holding her ass muscles, they felt gorgeous. If I were to die now, fucked to death by this beautiful shemale then so be it, a sissy dream come true. A with the thought of cumming true, a spasm racked her body, the resultant ejaculation flooded my throat, my mistress began to cum in me, filling my willing body with her goodness, spurt after spurt of creamy nectar. I gulped and slurped, borne by euphoria to my own idea of heaven. Finally she withdrew from me, I looked up, the stern mistress with strong legs, was more of a weak kitten, a kiss to the end of her half hard cock, caused her to cringe slightly and shy away.

The class were sitting open mouthed at the spectacle that had just occurred, lips were licked, dry throats swallowed, caught up in the climax of a Mistress. Her breasts were on show due to the titillation she performed on herself earlier, her cock now swung free beneath a hiked up skirt, she was still beautiful, even perhaps, a little vulnerable.

After that first day I chose Freya as my dining partner, eating sausages, fish sticks, chicken nuggets and chips on a regular basis from her ass. Carrots were O.K. but peas gave us a challenge, even with me sucking avidly at her ring, sometimes she fired several at once and I very nearly choked. I always thanked her with lots of kisses to her pouting anus and a loving lick as deep as I could get.

She had a dining partner who was in the third year, I felt jealous as she sucked her meals from that student but we must never forget to do as we're told. If I had made my jealousy obvious, I too would be forced to eat from another's ass, meal times would not be the same.

As a novice it was my job to scrub and fill the water tanks which connected to six cock shaped spigots set low on a wall. The flaccid rubber hung at mouth height to a kneeling student, on each sucking the water initially filled a bladder inside the rubber spout, swelling it in both length and girth. Only then did a valve open to allow fluid to be sucked cock like, from it. Continuous suction was required, enabling a student to drink but the slightest loss of pressure allowed two larger valves to open, causing the fluid to drain rapidly and the rubber to deflate in the blink of an eye. Some sissies drank just enough for a few squirts because they loved the connotation of sucking a cock but there was no other drink available, so all sissies had to use them every day.

My breasts were growing almost daily, I was in a 'B' cup now and loving it but my poor dick - sorry clitty, was not loved at all. Caged twenty four hours a day, barely able to pee properly, I was lucky we had to sit and pee because the weight of the cage pulled it downwards all the time. The open bars of the cage enabled it to get clean in the shower but it hasn't been played with for some weeks, ever since I started training in fact. We are trained to forget our clitty and concentrate on ass play, there are tutorials on the correct use of dildos and vibrators and when necessary, hold back from cumming.

I was having trouble in Mistress Kayne's class of Deportment, my ankles kept buckling when I attempted to walk in very high heeled shoes. I was offered the chance I to have the scene filmed as a money earner for next year's tuition fees, so that's what they meant by alternative arrangements. My attempts to walk were filmed by several fixed cameras, each failure was rewarded by a caning. I was bent over, my skirt lifted displaying my pert ass, the cane fell on my bare behind, in front of the class. I found the humiliation gratifying but I really couldn't find the strength in my ankles to walk any distance in those heels. After several canings I was given one final chance, Mistress Kayne said perhaps wearing frilly ankle socks might make me walk tall. I picked up and stroked each pink sock, rolling them up, easing my toes into the tight confines, drawing them tightly over my feet, sensuously. An itching started in my toes, a slight irritant which then travelled to my ankles. I stood and attempted to rub one leg against the other, to no avail, someone must have put itching powder into both socks.

Mistress Kayne looked sharply in my direction,

"Stand up straight and walk the line." she ordered, pointing to a white line marked on the floor.

By now I was itching badly, I had to wiggle my toes to try to alleviate the fiery ache but no, I was wobbling even before I started. My clitty cage was not only swaying from side to side but the jerking action was encouraging it to rise alarmingly, pain from the spikes both hurt and inflamed my poor clitty to even greater proportions. Mistress Kayne made great show of giving me a blue pill to swallow and ordered me to remove the cage before I crippled myself. I stood forlornly, the others just laughed, my clitty was jerking at half mast, no amount of control seemed possible.

"Bend over again," ordered the angry Mistress and raised the cane threateningly, I quickly complied but was jerking about so much, she could hardly cane my poor behind with any accuracy and laid stripes across the tops of my legs. That really hurt, I was so sorry that one of my favourite Mistresses had cause to punish me and tearful that someone in the class thought so little of me. By now I was crying out loud, sobs were shaking my body in a constant rhythm, she timed her strokes to hit my ass each time now, my lower body felt on fire but still my clitty was rising. The cameras were filming the punishment as the whole class laughed at me,

"Quiet, or you will all be punished," roared Mistress Kayne but as she hit me I was jerking forward, my hard clitty jabbing the air in a parody of fucking. The class found my antics far too amusing and the laughter continued.

A voice from the class, "Please Mistress, she seems to be enjoying it."

Mistress Kayne ordered me to stand up and sure enough my clitty stood out firmly, jerking up and down as I cringed and sobbed.

"The blue pill you just swallowed will keep you hard for hours, this disgusting display will continue for a long time, this will entitle anyone who wishes, to to punish you for showing poor control over your clitty."

With that she tied a yellow ribbon around the groove of my glans, ending with a large floppy bow, the only floppy thing about my rigid clitty for the next few hours. Mistress Kayne then had every one bend over for their disobedience in her class, all received several stripes on bare bums. I could only stare at each lovely bum as the cane slapped, wobbling the soft pliant flesh, leaving it's red mark of shame. No doubt the cameras were still filming, the Mistress was quite flustered by the time she had finished.

Hours later, several students approached me in the showers, perhaps they would commiserate, after all it could happen to anyone but no, someone behind me reached under and grabbed my balls, others my hair and one pushed the handle of a brush between my teeth, levering my mouth open. Water cascaded down, splashing on my face forcing me to swallow some of it, I fought as best I could but kicks and punches warned of getting too aggressive. A kick behind my knee and I fell to the floor, hands were scratching and poking, my face, body and even up my ass, clawing their way around inside me. Finally they all kicked the ribbon between my legs, taking my poor hard clitty to ever more painful heights. Some squatted, hot piss cascaded over me, directed into my mouth, unable to close because of the brush handle gag. They dragged me to my cage and a kick to the head was the last I remember. Later as I tried to piss, I realised just why they forced me to drink. My painful bladder refused to work because I was so agonisingly erect, further pain in my bladder competed with all the rest.

I hadn't believed it when told, that by the third year most sissies were asking for an Orchidectomy (ball removal). Apparently only the testicles are removed, the seminal vesicles and prostate are retained, and with it, the majority of their ejaculate. The skin of the scrotum was then stretched tight and sewn, a relatively simple procedure. Two 4th year sissies were considered to be ready for contracting out to owners, so we gathered to see their last test. They walked into the class naked but for naval jewellery and pink frilly satin bands on their wrists and ankles. They were neither bashful, nor proud, their nudity was just one more facet of their subservience. Jaydine was a tall brunette, with large breasts and smooth belly leading to a small, shrivelled, clitty. However neither she nor Amelia had any balls, their skin was smooth from perineum to the base of their clit. Amelia's clit was a stubby, shrivelled remainder of it's former self, probably unused for years now she derived all pleasure from her ass.

A large cardboard box stood at the front of the room, I could hear noises coming from it, the occasional squeal even. Mistress de Sade stood in the doorway, her full length black gown barely covering her gorgeous body. She swept in Majestically, oozing sex appeal and expensive perfume.

She pointed to one corner of the box and indicated Jaydine should kneel, I caught a lovely glimpse of her ass as she bent to comply, placing her knees on each side of the corner. Amelia was ordered to do the same on the opposite side of the box, at Amelia's corner I could see a small hole in the box, some four inches high. Presumably Jaydine rested next to another, because they were both ordered to stick their clitty through the hole.

There was a sudden commotion as four little piglets saw what they thought were mum's teats and scrambled to suck voraciously, two were successful and tugged, sucking away as if possessed. Obviously having no luck, they pushed hard with their snouts to bring forth the milk, still sucking, they tugged and pulled to no avail. Other piglets were pushing against them, which spurred them to greater efforts, toothless jaws clamped hard and jerked this way and that, until resignedly they let go. Others quickly took their place, again the hard sucking and tugging on what appeared to be soft clitties continued unabated. Once all the piglets had given up, the girls were ordered to stand, each had a soft, limp clitty and everyone clapped.

Mistress de Sade handed out two vibrators and soon the two girls were bending over and taking a large vibrator up their ass, wielded by eager students. After a while it was my turn to excite Amelia, I knelt to spit on her open ass hole, then pushed the large vibrator easily inside her, I loved the feeling of control as she pushed back onto it. I pulled and pushed the throbbing vibrator ever deeper into her ass, cream dripped from it as I plumbed her depths, revelling in turning this girl on. Her ass was bucking to and fro, and, as it neared my face I kissed it. Soon the vibrator was almost lost inside her, I gripped the end with my teeth, the vibration felt like an electric toothbrush as I pulled back, then my nose hit the crack of her ass as I drove it in. I held around her ass, my face wedged into her, the vibrator lost as I kissed her ring, my tongue slipping in behind it to lick the soft pink walls of her ass pussy.

She expelled the vibrator back at me, straight into my mouth, I managed to block it with my tongue and pushed it right back to where it belonged. She wriggled, delightfully, expelling it once more, it pushed my head back a little, such was the force. Back it went, whirring away like a demented food mixer, sheathing itself into the warm depths of this young sissy. Her ass shuddered, I put my hand to her limp clit and was rewarded with a trickle of juice, I continued to lick her open hole, grateful that I could bring her to climax. Raising my hand, I licked the residue and thanked her as a good sissy should, she sat back, the vibrator fell from her and rolled to one side, another student licked it clean, as a matter of course.

My second chance to star in a film was a torture scene, after the canings I had suffered previously it didn't seem too big a jump to say, yes. This would be my first real encounter with Mistress de Sade, she was gorgeous, with a body to die for, I was hoping it wouldn't go quite that far. For this scene I was wearing office clothes, a dark blue pencil skirt and jacket with a frilly blouse beneath. Black stockings and garter belt complemented the look, my high heeled shoes were still a problem for me, so I moved as little as possible. I sat demurely on a chair, awaiting her arrival.

"Your work to date is deplorable," said Mistress de Sade, walking toward me in a red, tight fitting dress. Her breasts were heaving, barely held by the plunging neckline of her dress. Her body appeared to have been poured into the tight fabric, any trace of underwear would have shown telltale marks of their presence. Strong powerful legs encased in smoky nylons rose tall and curvaceous to the high hemline which threatened to show lacy stocking tops at any moment. She bent to grab my arm, no doubt showing her stocking tops to the cameras, together with the rounded curve of her bootylicious ass.

"I'm sorry, Mistress but I have not been trained for the work you have set me," I ad libbed.

"So you lied in your job application."

"Only a little, I thought I could pick up any new work as I went."

She held my arm, I struggled, the jacket came open, my low cut blouse spilled one breast into view.

"You can't even dress properly for the office," said snarled, ripping the other side of my blouse and baring my other breast.

"Where is your bra?"

"I'm sorry, Mistress, I will try to do everything better in future."

"What will you do to ensure you have a future with me?"

"Anything, Mistress, I need this job."

She fondled the exposed breasts with one hand, holding the neck of my jacket and blouse with the other, pulling both from my shoulders. I stood naked from the waist up, she held the skirt zip in her hand and as I struggled it pulled down. The skirt fell from my hips, revealing my slim body adorned in garter belt and sheer, black stockings. Her teasing of my nipples had caused my clitty to harden,

"You disgusting creature, how dare you allow your clitty to become aroused."

"Perhaps you would show me the error of my ways, Mistress."

She threw me toward a brick wall, various rusty rings and chains adorned it. My wrists were locked into shackles above my head, I felt very vulnerable standing there in just lingerie. Going to the desk and chair where I was first seated, she held up a take away carton.

"So you think it's reasonable to eat food in the office?" She smelt it. "Spicy food, Chilli and Tabasco, what if this got on your skirt, or perhaps, your skin?"

"I'll have to take off my dress so that doesn't get spoiled."

With that, she unzipped the red sheath dropping it to the floor, a veritable Goddess stood before me. Her breasts nestled on a maroon balcony bra, matching panties adorned her hips, the hold up stockings gripped her legs with their garter like tops. Her high heels gave her legs definition, her perky ass it's rounded curves. She smiled, bewitching in it's beauty but the flat gaze belied it's innocence. Holding a condom, she poured some spicy food into it, I could see a bulge in her panties growing with the thoughts of what was to follow.

She approached me, I struggled futilely, there was only one place that was going to be put, it slipped easily over my clitty,

"Take it off, Ow, please Mistress take it off."

"You dare tell me what I should do in my own office?"

I shook my head, I couldn't win but then, I was never meant to. She squeezed the outside of the condom, mashing the contents harder over my throbbing clitty, the pain was excruciating. She stood back, as I bucked to and fro, then side to side but nothing would relieve the pain. Tears streamed down my face as I twisted in agony, through the liquid veil I saw her cock swelling as she gained stimulus as she watched. No doubt the cameras had a good view of her transition, her panties bowing out as her cock grew fatter, then the tip appeared to peek from the waistband. She picked up a piece of broom handle, putting the rounded end to the tip of my engorged clitty, rolling the condom onto it, there was no respite for my coated clitty, the fiery agony continued unabated.

Putting the broom handle into a metal holder on the wall, she undid the shackle on my right wrist, perhaps it was over, maybe a soothing cream waiting to end this misery. She nudged my foot over the other with her leg, I swung around facing the wall, another shackle hung there and was clamped around my free wrist. No, not that, my brain was working overtime, No, not my ass pussy.

"Please, Mistress, surely I have been punished enough."

"Do you get to set your own level of discipline? she enquired, haughtily.

I watched over my shoulder, as she unclipped each side of her straining panties, throwing them towards the desk. Her cock was hard, sticking out at a jaunty angle, all because of my helpless plight, even in my agony I could worship at the feet of this cruel shemale. Of course it was no surprise Mistress de Sade would get off on the pain of others, I had signed to the academy for humiliation and pain but I hadn't thought it would be this much.

Picking up the condom covered broom handle, she approached me, I was trembling, my knees felt weak, it hurt enough on the tender nerves of my clitty. How bad would it be in my ass? Her fingers were delving into that very orifice, skilfully she eased into me, widening my sphincter with a deft, practised hand. I could feel the slippery coated condom pushing in to the crease of my ass, there, it slipped into me.

"Aargh," the scream was ripped from my throat, the fiery explosion burned my tight ring. It may just have been an inch or so scorching my insides but I was trying to climb the wall to escape it. I could feel the back of her hand against my thigh as she held the wooden pole to my ass like a branding iron. Her hair brushed my shoulder as she leant forward,

" I bet you could scream louder than that," she cooed in my ear.

With a sudden push, more of the condom slid into me, this time I jumped but soon fell back, to slip even further onto the torture device. My world collapsed. All that existed was pain, clawing it's way through my gut, pushing her arousal ever higher, it nudged the back of my thigh as she drove the pole in deeper, I screamed,

"Mercy, Mistress, I beg of you, I'll do anything, if only you would stop the pain."

"You'll do it anyway," she said, "I've made up my mind," pushing the pole deeper still within me.

My scream reached a higher pitch, tears were dribbling into my mouth, I was a blubbering, writhing wreck. My cruel Mistress started working the pole up and down, her nipples hard, cock jerking due to the effort used to inflict such pain. I sagged in my chains, a plaything for evil intentions, the extent of my cries were all that was needed to bring her pleasure, a hard thrust and she elicited more.

I screamed, "Please Mistress, let me suck you, allow this poor wretch to worship you."

"Shall I whip you 'till I cum?"

"Oh, yes Mistress, it would be an honour to accept your discipline just to suck your nectar, like the most humble bee at a beautiful flower."

The condom covered pole was removed but not the pain. Shackles were released, I fell to my knees, not in supplication but simply from strain and fiery burning deep within me. The Mistress saw it as an opportunity to stand Majestically above me, God she was gorgeous. I looked up past the grip top, sheer stockings past the smooth flawless skin of her thighs, up to the huge cock thrust urgently skywards. I leaned in to kiss this monument to shemale perfection, a sharp crack and the lash cut me across my back. I arched my back in automatic reaction, my head rose up, face slapping against her cock,