Sissy Downfall

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Now my little lover. You may get to work on her other breast. Please make it match the appearance of the first one in readiness for its clamping." My mistress says to her young friend.

Pulling her hand from between her legs the girl snatches up the cane and takes to her task with pleasure. The wet patch on her panties is now mush bigger and her juices are running down the inside of her thighs and wetting the tops of her stockings.

Soon Sue's other breast is as red as the first and the clamp and weight are applied. Sue is just hanging and quietly sobbing.

"Release the maid, Lisa" the mistress commands her young assistant "I have work for her.

My bonds are released and I stand as commanded.

"Kneel before Sue and suck her clit until it is stiff. Do not make her cum. I just need her stiff for her next torment."

With difficulty I kneel. The plug in my rear becomes more obvious in this position but at least my clit is no longer being squashed.

Taking her into my mouth I suck and slide back and forth. I am amazed at how quickly Sue becomes hard. I know she is ready as the pressure on the roof of my mouth is very high as her clit strains to stand upright against her belly.

Suddenly I am pulled away by the mistress who then steps for ward and slides a rubber ring down Sue's clit so that it must stay stiff and against her tummy

I am ordered out of the way, and told to kneel near the seat I have vacated. I have a good view of Sue hanging there with her red striped breasts, stretched nipples and clit standing upright

Suddenly the mistress strikes with her cane slashing furiously across Sue's belly and of course hitting her clit as she does so. Sue screams with the new pain coming from a different site to all the others. Her clit, surprisingly stays stiff as it is reddened by the beating. Suddenly she is silent as she passes out from the pain.

Undoing the rope and allowing it to pass through the pulley the mistresses lower Sue to the floor.

"Help us to lift her" she orders me.

The three of us pick her up and lay her on the rack. Mistress removes the rubber ring and her clit subsides.

We roll her over and the mistresses secure her wrists and ankles to the ends of the rack. Her breasts, still weighted hang through holes in the platform upon which she lies. My mistress turns the wheel at the foot end which applies some stretching pressure to Sue's tortured body. A restraint is attached to her clit which is the connected to a smaller wheel. When this is turned her clit is stretched and pulled toward the foot of the rack. She is left in this position to regain consciousness.

Mistress approaches me carrying a strange rubber bag which she forces into my mouth.

Connecting a bike pump to it she inflates the bag which quickly invades my whole mouth and starts down my throat. When I start to choke she stops inflating, removes the pump and steps back to admire my stretched cheeks.

"This is an inflatable butt plug which I am going to use on Sue. I wanted you to understand how it works. At the moment it is only partly inflated. Sue groans as she wakens in the back ground. After deflating the bag and removing it Mistress takes it to sue and forces it through her rectum and into her passage. She quickly inflates it and I can see Sue's back rise as her stomach is forced out by the increased pressure inside. Sue groans at the discomfort inside her.

"You have seen quite enough maid. Go to the kitchen and have some lunch. Return in half an hour with dry panties for us and to collect the tray" mistress orders me.

I leave the room and negotiate the stairs with care as my ankles are still restrained. At the kitchen door I hesitate wondering what the cook has in store for me. Hunger finally gets the better of me as I have had very little real food since the previous day and I step sheepishly into the kitchen.

"Send you up to get fed did she?" he smiles fiendishly.

"Yes" I answer head bowed.

"Well. First you will have to worship my manhood again. If you satisfy me I will feed you something. On your knees bitch".

I drop down and soon have the head of his cock forcing its way into my throat. Fortunately he comes rather quickly, filling my throat and nearly choking me. He withdraws and I suck the last drops from its tip.

"There is bread over there and some butter. Make yourself some sandwiches and there is coffee in the percolator".

Thankfully I make myself a sandwich and coffee which is quickly devoured as I am soon due back to deliver fresh panties to my mistress and her consort.

Carefully negotiating the stairs I go to the mistresses room an after a short search find a drawer full of panties. I select two pairs of sheer black bikinis and head back to the torture room.

Upon entering I find the two mistresses making love on a huge sheepskin rug on the floor. Both have removed their panties and my mistress is wearing a strap on dildo which also has a second shaft which enters her own pussy. She is vigorously humping her young lover who is on her back under her quietly moaning with pleasure. Their skins are glossy with perspiration while their pubic regions are dripping with their juices.

Hearing me enter my mistress looks over her shoulder and says "leave the panties on the table and release the slut from the rack. Take the tray to the kitchen and wait in your room for the beautician to arrive. She will prepare you and instruct you in your evening duties. Sue, you will go to your room and also prepare for the evening".

Approaching the rack I find Sue stretched to the limit. Her arms and legs are taught and her clit is stretched tight between her legs. Her breasts hang through holes in the base stretched by the weights on her nipples. She is covered with welts on every bare piece of skin. She moans quietly as I release the pressure and help her to stand unsteadily next to the rack. Having removed the clamps and weights from her swollen nipples I helper to walk to the door. She moves slowly and stiffly as I follow her to the kitchen where she waits while I leave the tray.

"Please come with me and help me undress as I don't think I can manage on my own" she implores.

Feeling sorry for her I follow her to her room which is near mine and help her out of her clothes. At her insistence I rub some soothing cream on her welts and leave her to go to my own room.

A large severe looking woman is waiting for me. "Where have you been you slut? I don't like to be kept waiting." she hisses at me.

Standing up, she slaps me hard on the face. I burst into tears and beg for mercy.

"There won't be much of that over the next couple of hours. I have much to do with you to prepare you for tonight" she as she roughly turns me around and unlaces my corset.

She unbuttons her dress and removes it exposing her underwear which consists of a flesh coloured body suit that tries to contain her fat and stay up stockings.

Grabbing my head she pulls me with her to the bed end upon which she sits and forces me to my knees in front of her. She pulls my head between her now spread thighs. I can see the wetness on the gusset of the suit which has small press studs securing it.

"Now I will have some pleasure before we start on your preparations. Undo the studs with your teeth you bitch".

I grasp the edge of the gusset in my teeth and pull until the studs are released. The stretchy cloth springs back to reveal a mass of long pubic hair. I almost faint at the stench of sweat, stale urine and poorly wiped bottom.

"Now eat me bitch".

Having no choice I start.

I don't know how long I worked at the foul task but finally she climaxed covering my face in her juices. She released my head and with relief I was able to stand and get away from that horrible place. If it had been one of my mistresses I would have loved it but not with this creature.

I could smell her on my face and longed to wash my face.

"Remove the rest of your clothes bitch" she said as she stood and fastened the crotch of her bodysuit.

As I undressed she opened a large leather case and removed a syringe and bottle of liquid.

"Lie on the bed. It is time for your hormone injection'.

I lay down and felt her roughly inject the fluid into my bottom.

Slapping my cheek hard and ordered me to go and wait in the bath room.

She soon entered and told me to wait on hands and knees while she prepared an enema.

I soon felt her force the nozzle into me and the warm soapy water flooded my passage. Soon I was begging her to stop as she was overfilling me. She just laughed and pinched me hard on the bottom. Finally she was satisfied I was full and with difficulty I stood and moved to the toilet where with a great rush I emptied.

"Now we will fill you again" she laughed.

It took four huge fills to cleanse me to her satisfaction.

"You may now shower and then I will prepare you for the evening entertainment'.

With great relief I was able then to clean off her stench from my face.

Soon clean and dry I returned to the bedroom where she indicated that I should sit at the dressing table. Sitting next to me she proceeded to make up my face.

"Watch carefully what I do as I will only teach you this once'.

She expertly made up my face. At the end of the process I was very impressed at her skill as I looked at my womanly reflection. It was perhaps a little overdone and sluttish but pleasing all the same.

"Stand and I will help you dress" she ordered.

Around my waist she placed a black bustier which laced up from the back. The bodice was padded so that when she laced me tightly, working from the bottom up, the small breasts that I had were pushed up so forming the illusion of some cleavage. She applied a lot of pressure to the lacing forcing me to breathe out. I felt weak at the end of the process but loved my new narrow waisted shape.

Next she handed me black seamed lace top stockings which I slid up my legs and fastened to the suspenders on the bustier after she checked that the seams were straight.

My clit restraint was handed to me next and was soon fastened to a newly fitted hook on the bustier back pulling my male parts out of sight.

She passed me a pair of sheer black panties. They were G string style and high waisted.

Sitting I pushed my feet through them and pulled them to knee height. Standing I slid them gently up my thighs, loving the silky feel as they slid over my stockings, and into place. The front was sheer as was the gusset which was wide enough to cover my clit and other parts between my legs and then narrowed down where it pulled into the crease between my cheeks. The tip of my clit was just visible from behind.

The soft material caressing my clit tip as I moved soon had me dribbling a little pre cum into the thong.

Noticing this, the fat woman said "Oh good. Your mistress likes her girls to show a little wetness. It shows they appreciate their position and also excites her guests. Now we will lace you into your uniform and shoes".

I slide the black maid's uniform up my legs and put my arms through the sleeves. It consists of a central corset which is soon laced tightly around my waist a short flowing skirt that barely covers my bottom when I am standing upright and a blouse at with plunging neck and puffed sleaves with white lace trims. A white apron and cap complete the set. There are hooks on all sides of the skirt to hold the skirt raised to expose me to view and touch. There is a small pocket in the apron.

"Always keep a lipstick in the pocket as you are going to need to recover your lips regularly during the night".

She selects the shoes. They are black and impossibly high. The heels are seven inches of wicked spike with soles only half an inch thick so that my feet will be steeply sloped. There are ankle straps with little locks to prevent removal. Once the shoes are fitted I find it impossible to take any more than short steps. My calves are stretched tightly and they force my back to arch a little.

"Try kneeling" I am told.

I find that it is very difficult but not impossible to get to my knees and then stand up. After fitting a blond shoulder length wig and the cap I admire the look in the mirror. I am ready to serve.

"Practice walking, kneeling and curtsying until the mistress calls" she says as she leaves me.

The next hour is spent practicing my womanly walk. My steps are short and mincing and I find I can kneel elegantly with practice.

Finally the intercom sounds and my mistress summons me to her chamber. Upon entering I find Sue, dressed in the same uniform as me except that her reddened breasts are exposed through a space left in the blouse, standing near a table on the balcony where our mistresses sit. They are both naked and enjoying the sun on their smooth skins.

I approach and curtsy.

"Turn about so I can inspect you".

I do so and she expresses pleasure at my look.

"You two will now bathe us and help us prepare for the evening pleasures".

The next hour or so is devoted to bathing them; washing and brushing their hair and helping them dress.

They wear identical tight sheer black long dresses over stockings, suspenders and g strings.

They are braless and bare shouldered with nipples protruding. High heeled shoes complete the outfits. They look like models.

"Leave us while we are made up and look after our guests as they arrive".

We pass the make up woman on the stairs as we descend to wait in the entrance hall.

"Hook up the backs of your skirts. The mistress likes her guests to have easy access to a maid's bottom" she hisses as she passes.

We help each other to expose our already reddened backsides and wait for the arrivals.

"Do you have to work in the kitchen?" I ask.

"No. Tonight I will be helping you to serve drinks and food to the guests. There is extra staff brought in to help down there. Watch out for the barman, he is really cruel to us girls. He thinks we are freaks and enjoys hurting us. We will also be required to serve our guests in any way they command. I hope your lipstick is full" she answers.

The doorbell rings. Sue opens the door to reveal a beautiful leather clad woman leading a younger woman, in a long white cloak, by a leash connected to a collar round her neck. We curtsy as they enter and I notice that the younger woman is only wearing lingerie under the cloak which swings open as she walks. She wears white high sandals, white stockings and suspender belt, sheer panties and a low cut bra which exposes her nipples.

I take them to the reception room where the function is to be held. While I fetch a tray of drinks the young woman is taken to a corner of the room and told to sit on a hard wooden bench. Pulling her cloak aside to expose her body she sits. Her leash is locked onto a ring in the wall. She sits with knees clamped together, her back straight and her eyes downcast.

"Spread those legs slave. I want you pussy exposed for all to see".

Once spread it becomes obvious that those panties are crutch less so that the smooth hairless labia which are painted in lipstick are exposed for all to see. My clit weeps with the sight of it.

I have to go behind the bar to get a tray of drinks and the barman pinches me hard saying "I hope that hurts you sissy" as I leave.

As I serve a drink to the first guest others arrive.

In each case it is a master or mistress leading their slave. All the slaves wear the same cloak with the same lingerie underneath. Once they are seated and restrained on the bench some differences become obvious. Through their panties become visible little boy/girl clits, some are restrained and others hanging forward, while some are like the first girl with her real pussy.

The last to arrive is Mistress Rebecca with her slave. Once seated it becomes clear that this slave is different to the others. She is a transformed boy with large implanted breasts. Although her penis is still intact she is castrated. She is quite beautiful.

Eventually there are eight young slaves sitting silently on the bench. Their masters and mistresses mingle and chat. Whenever I pass one of them I receive a slap or pinch on the bottom as does Sue.

One man detains me as I pass and tells me to put the tray on the bar and return to him.

I do so and he forces me to my knees in front of him. He has tight leather pants with an exposed zip.

"Unzip me and worship my dick" he snarls at me.

I unzip him and release his huge penis from the pants. It is already swelling as I take the head into my mouth. Within seconds my whole mouth and throat are invaded by its length and girth. Grasping my head in both hands he forces his way in and out. I am being fucked in the mouth and throat rather than me giving him head.

Finally I feel it spasm and he floods my throat with cum. He is as deep in me as possible and all I can do is swallow to save from choking. Pulling back he releases me and a few drops fall to the floor at my knees. I lick the last drop from the tip and he steps back to zip himself up.

"Lick up that mess bitch" I hear my mistress say.

As I do so she addresses the guests.

"She does that so well with so little training. I am sure you will all want to use her in some way as this is her first night on the job. Please restrain yourselves and save yourselves for the long night of entertainment ahead".

Flicking my bottom with her crop to get me standing she sends me to the bar where there is a mirror to repair my lipstick. As I do so I feel the barman's hand between my legs. He squeezes me hard so that I almost faint and laughs as I mince away with my tray of drinks.

Time passes as the guests enjoy the food and drinks. The slaves on the bench are left alone apart from occasional inspections by their masters and mistresses who feed them small portions of food and sips of drink.

"It is now play time" mistress says "bring in the couch, maids" pointing to Sue and me.

I follow Sue to an anti room where we pick up the couch and carry it to the main room and place it in the middle of the floor where all can gather around. It is a narrow wooden bench about six feed long and 18 inches wide covered in padded leather.

"Who will be first?" my mistress asks.

"Take mine, she needs the punishment quickly" says one of the women.

"What has she done?" my mistress asks.

"I caught her with a boy. Fortunately I stopped them before she was penetrated. Now she must learn that only I can provide the satisfaction that she craves. Can one of your maids get her prepared for what we discussed earlier?"

I was soon kneeling in front of the girl with my tongue lapping her clit to make her wet. So was entranced by her taste and perfume that my own clit was dribbling profusely.

In the background my mistress was issuing instructions. "Get him hard in readiness to receive her".

My task was soon complete as she was now dripping with cum and my saliva. I was ordered away and went to repair my lipstick. Sue was sucking hard on the tip of a huge penis protruding from a leather clad man lying on the couch. She too was soon called away as her job was done.

Two men picked up the girl holding her at the back of each knee and shoulder. They positioned her astride the prostrate man with the enormous knob pressing against her vagina.

"Please no mistress" she called as they lowered and then forced her down onto the massive member "it will split my open".

"That is exactly what I want. You will soon realise that men only bring pain to girls like you' her mistress replied.

She screamed suddenly as the whole length disappeared inside her. Sitting astride him then she sobbed but didn't move.

"Hump him you slut" she was told.

There was no movement from her until, with a thwack; she was hit by a riding crop. She was soon riding him rhythmically to the beat of the crop on her cheeks. A steady stream of pink stained cum was visible on the shaft each time she lifted.