Sissy Downfall

Another master moved in behind her with his erection protruding from his zip. Holding her down on the first man he pushed her forward so she was lying on his chest exposing her bottom to him. Scooping some cum juice up from her soaked crease he coated his shaft end her arse hole. Then positioning his knob against her hole he forced himself inside.

She screamed as she was split open and her blood flowed onto his shaft. He soon buried himself inside and humped her back and forth. Her body was also moving back and forth on the first shaft still buried inside her cunt. She cried and cried her tears falling on the leather clad chest below her. The double fucking continued for many minutes until her anal rapist was ready to cum. pulling out of her he backed off and walked to the side of the bench. Pulling her upright by her hair and turning her head he forced himself into her mouth and throat where he quickly dumped his load. After waiting to be sure it was all swallowed he pulled out and retreated to watch.

Meanwhile the first master was also ready and soon lifted her off him self and pushed her down to where he could force her mouth over him. With great difficulty he forced the huge shaft past her lips and into her throat. She gagged repeatedly as he fucked her throat until with a spasm he also emptied himself.

He then lifted her head off him and cast her aside where she fell to the floor bleeding from mouth, cunt and arse her body convulsing as she sobbed.

"Maids; Return the couch to the anti room and take this used girl and leave her on it to recover. Then clean up the mess she is making on the floor" said my mistress.

We quickly comply and as we are licking up the blood and cum from the floor while our mistress addresses her guests.

"It is now time for the real entertainment. We shall now retire with our slaves to the dungeon. Maids and barman please go ahead and wait at our service."

Sue and I follow the barman to the dungeon where he opens up the bar for service and we wait to take orders.

The mistresses arrive with their guests each with their slave on a lead. As we take orders the slaves are relieved of their cloak and led to various restraining positions where they are variously strung up or stretched out for torment. Each is gagged. I watch enthralled as various clamps are placed on nipples, labia and clits both male and female. My own little clit is dribbling a steady stream into my panties.

All around the room slaves are writhing in pain as they are subjected to whippings, stretching' penetration and clamping.

Mistress Rebecca beckons me to join her. "You will watch me play with my slave. You need to see what awaits you once I have purchased you from you're current mistress." I am led across the room to where the mistress has parked her slave.

Mistress leads her slave to the device near the far wall and places her over a large steel phallus mounted upon a hydraulic ram secured to the floor .Her ankles are secure to ring bolts set into the floor. A leather belt is fastened around her waist with chains that are then secured to the ring bolts on the floor. This forces her to bend his knees and support her weight with hers calves and thighs. Her arms are secured behind her back with cuffs.

Mistress touches a button and the phallus rises until it is forcing its way into the hapless slave's bottom and is stopped at that position. Soon the slaves' legs succumb to fatigue and she slowly slides down onto the steel phallus. As she reaches full penetration a painful electric shock is administered through the phallus forcing her to try to stand up. She holds up for a few minutes until the leg fatigue sets in again and she gradually sinks back onto the shocking device again. Mistress lets this continue for some time until she takes to the subs breasts and clitette with a cattle prod. This makes the sub jump and bounce on and off the electric zone of the phallus. The punishment is unrelenting until the sub passes out.

"This is what you can look forward to when you are under my control" Mistress Rebecca whispers to me. My heart flutters with fear. My clit dribbles with anticipation.

My young mistress approaches me and leads me to a device like a vaulting horse with a studded leather covering upon which she instructs me to lie face down after first removing my panties. My face just overhangs one end while my legs hang down over the other and my feet are just on the ground. A leather strap is fastened over my back at waist level and my wrists are secured with straps to the floor. I feel a cuff placed on one ankle and my legs are spread by a bar which is then attached to the other ankle.

Unfastening my restraint from my waist she pulls my clitty down and fastens to another strap from the floor. A head harness is fitted which has a strap under my nose and another across my forehead which is in turn pulled back and fastened so that my head is held back. I feel my skirt flipped up over my back.

"If any one wants to use this maid please feel free. As you can see, her arse and mouth are both easily accessible for penetration and her bottom and clit are ready for punishment." The young mistress announces to the guests.

Almost immediately I feel the burn of a cane cutting across my bottom followed rapidly by many more blows. My screams are soon silenced by a gag, which only allows a whimper as the blows rain down. My tears run down my cheeks and puddle on the floor.

After an eternity the blows stop only to be replaced by a new torture as a large penis head presses against my bottom. The force increases rapidly and suddenly I feel as If I have been split apart as the massive shaft is forced inside me. This is the largest object I have ever encountered entering my passage. I feel a trickle of liquid running down the inside of my legs. It must be blood. The whole length is inside now and must be a foot long. I try to move as it is slowly withdrawn and forced back inside over and over again but can only wriggle a little. I can hear laughter and lewd comments from the onlookers.

Hours pass it seems. Really it is probably five or ten minutes. Suddenly the movement stops with the massive rod fully embedded in my bowel and I feel a pulsation from the head of it as it spews forth a stream of cum far inside me. After some seconds I felt the huge beast slowly withdrawn from my punished hole. As I start to relax I feel another push at my sphincter and realize that I am to be invaded again. Slowly another only slightly smaller prick insinuates its way inside me and the rhythmic pumping starts again. The pain has now reduced from extreme to just a dull throbbing and so the need to scream is replaced by sobs and tears as my ordeal continues.

The gag is removed from my mouth and I know better than to say anything or beg for mercy. The chance to speak is soon removed as another penis appears in front of my face and is pushed against my lips. Having no other choice I open wide to accept this new assault. The corners of my mouth almost split with the size of it as its length disappears to the very back of my throat. In my immobilized state I am not giving head but rather, being fucked in the mouth as the rod is forced in and out in time with the other at the rear. Quite quickly the front man climaxes onto my tongue and overflowing my mouth as I am unable to swallow quickly enough. The rear man soon follows and they both withdraw to be replaced by another pair of similar size.

After what seems an eternity they are all sated and I spend a little time recovering. I can feel fluids running down my thighs and chin that must be blood and cum. This is soon confirmed as my mistress kindly replays some footage of my punished rear on the screen of a hand held video camera used to record my humiliation. The damage to my hole is frightening to look at and makes me wonder weather I will ever walk again.

Mistress Rebecca asks my mistress if she is allowed to cane me.

"Of course you can" Is the reply.

Seconds later I hear the swish and feel the bight as the cane slices into my flesh. My cheeks are soon on fire as blow after blow lands upon my behind. She methodically works her way down from the top of my crease to the tops of my legs. The crowd soon pleads for me to be gagged as my screams are loud and constant. She then works down each of my thighs careful not to hit my dangling boy bits. Once these areas are completely reddened she gives my balls a playful tap with the cane. Unfortunately the hit is harder than she plans and I pass out.

Later, I do not know how long, I start to come to as I feel my bonds being released. I am pulled roughly to my feet and fall in a heap on the floor when let go.

"Get up slut" my mistress barks.

I try but fall again from the pain to my torn and reddened rear. My mistress instructs Sue and the barman to help me to my room. The barman grumbles all the way saying that it is not his job to help sissy sluts to walk.

As we reach the door to my room I trip and fall bringing all three of us to the floor.

The barman's anger overcomes him and he starts to punch me in the face and scream obscenities at me. I feel my nose and jaw break from the assault just before I pass out again.

I awaken in a strange room. Looking around I work out that it is a hospital room. As I become more aware I realize that I have a drip in my arm. Trying to move I find that I am restrained at the ankles and across my tummy. There is a dull throbbing pain in my face chest and bum. As my hands are free I feel around my body and discover that my face and chest are heavily bandaged.

"Oh, your awake" turning I see a nurse entering the room. "How do you feel" she enquires.

"Quite sore," I answer.

"I'm not surprised you have had quite a lot of work done."

"Can you tell me what has happened please" I plead.

"You were brought in by your mistress with a broken jaw and nose and with severe damage to your rectum. We repaired and modified your face as instructed. With a smaller nose and chin and fuller lips you will look much more feminine. We also repaired the damage to your rectum and made it wider to reduce risk of damage in the future."

"What about my chest?" I ask.

"Your mistress felt that a nice set of implants would complete the transformation. The bandages will be removed shortly and you will see what a great job we have done." She leaves the room and I feel for my little boy bits to see if they still there. They are.

The nurse returns with a doctor. "Still a bit sore I hear. That will soon pass. We will now uncover your new self. There will be some bruising but the swelling will have gone and you will be pleasantly surprised at how good you look." The doctor says.

Having released my bonds they sit me up and remove the face bandages. I see myself in a mirror held by the nurse and am shocked by the change. Staring back at me is a beautiful woman. Next they remove the chest bandages and I look down to see a magnificent set of c cup breasts. The mirror is again held up and I am astounded by the new me.

"For the next week you must wear a sport bra at all times and then you may wear what you like" I am told.

"We will remove the drip now and you can shower put your make up on and dress, as you will be picked up this afternoon. I suggest you don't have anal sex for a few days until your bottom has healed a little more".

The drip is removed and I am left to make myself presentable. Walking to the bathroom I just love the feel of my new breasts as they undulate ahead of me.

The shower finished, I admire the new me that I see reflected in the mirror as I dry myself. There is some deodorant and perfume available, which I apply to myself. The deodorant is quality but the perfume is strong and obviously cheap. I know from experience that I am expected to use it liberally and so slap it on my wrists under my breasts, around my crotch and my neck. I can't help fondling my breasts and delighting in the tingle I get as I caress my nipples. I just love the pert nose, small chin and full lips that stare back at me.

Moving back to the main room I see a cupboard, which once opened reveals a set of clothes my restraint and some make up. There is the sports bra, suspender belt, mini skirt and sheer blouse all in white. A tiny thong in red, white four inch heeled sandals and sheer seemed tan stockings complete the outfit.

Having fitted the bra I secure the suspenders to give me something to hitch the restraint to. I push my clitty into the restraint, pull it between my legs and hook it to the back of the suspender. Sitting down I slide the stockings up my legs and, being careful to center the seam, attach them to the belt. The red thong is soon in place, covering the restraint.

The skirt once fitted just covers the stocking tops when I stand and is of such light material that the suspenders and thong are clearly visible. My bra is also clearly visible through the blouse. I look forward to wearing it without bra or with a really pretty one once my breasts have healed. As I peruse myself in the mirror I feel the delicious sensation of precum oozing out of my clitty.

Grabbing the make up case I sit at the dressing table to apply my make up. In the case is everything needed to comply with the note inside, which says "apply plenty of everything to cover your bruises and make sure the look is super sluttish. There are also some earrings and a necklace amongst the makeup.

Suddenly I realize that my juices are probably staining the back of my skirt. Standing and twisting so I can see my rear in the mirror, my fears are confirmed. An obvious stain is visible on the skirt. Quickly removing the skirt I rush to the bathroom and rinse the stain and then hang the garment over a chair back in the sun streaming through the window to dry.

Returning to the makeup I am surprised at how long my hair has become. I wonder how long I have been here. After applying a heavy coat of foundation I heavily coat my lids in lurid green shadow, darken and shape my eyebrows and apply heavy mascara. Some blusher follows and then a very bright red to my new lips. Pulling out the earrings I discover that they are one inch long gold penises hanging from the hooks which I place through my ear lobe replacing the sleepers which had been there. The necklace is a gold chain with matching but larger penis hanging from it. I brush my hair thinking that I need the attention of a good hair dresser.

My mistress walks in at that moment as I am about to stand and retrieve my skirt.

"Ah" she says "nearly ready are you my little slut. But why is your skirt hanging in the sun?" she strides over to the garment and inspects it carefully.

"Oh I see. A stain you randy little bitch. Put it on now so we can leave. We need to get your hair done and buy some clothes appropriate for my new hooker.

I slip into the skirt, grab the makeup bag and follow her into the hall. She is wearing thigh high black boots with wickedly spiked heels over stockings whose tops are just covered by her tight black leather skirt. Up top she wears a beautiful low cut lace bra partly concealed by a short black leather jacket which is open to the waist. Her make up is subdued compared to mine but still manages to make her look sexy. My clit just dribbles at the sight of her.

She leads me to the car and orders me inside. As I sit I try to pull the back of my skirt up to protect it from staining.

Seeing this she hisses at me "Pull it down you tart I don't want your' cum on my seat.

Anyway I think you will look the part walking around the shopping center with a stain on you skirt. With the earrings, makeup and those red panties everybody will know that you must sell your self for a living and the stain will confirm it. The perfume will reinforce the idea in their minds. Ah well, best you get used to the idea now."

I wonder what the future holds for me now. Is she going to sell me to any one who lusts after a bit of shemale action?

I adjust the back of my skirt so that it will absorb the juices that are still trickling from me. The front of my skirt rides up so high that the creamy bare skin above my stockings is clearly exposed as are the suspender laces and even the gusset of my panties. My mistress lowers the roof and we drive off towards the mall.

"Love the look" she sneers at me. "I hope there are plenty of truckers around with CB radios to alert their friends of the view available to them all."

We are soon on a main road passing through suburban shopping strips and we cruise along in the gutter lane slowly as there is much traffic. Often we are stopped by the traffic and the lights. Attracted by the looks of the car the many people on the street look down on us as we wait to move on. I try covering my crotch with my hands to hide my panties.

"Put your hands at your sides bitch and spread your knees a little or I will punish you" she hisses.

I, of course, comply with her wish. The reaction from the shoppers on the street varies from disgust by most of the women to outright lust from many of the men.

"Apart from the obvious changes I have made to you there are some other things I had done while you were in the hospital. All your body and facial hair has been lazered off and you have a hormone implant, which will keep you dosed correctly for a year. So, what do you think of the new you?" she asks.

"I love it thank you mistress. What is to be my role in your household now?" I reply.

"You will become a sort of personal assistant to me. Your full duties will be explained later. Giving pleasure to my guests will still be part of your role but on the whole there will be some pleasure for you between the pain." She says smiling.

"Oh thank you mistress" I gush.

We soon arrived at a shopping mall and alighted from the car. My mistress inspected me and expressed pleasure at the obvious stain on the back of my skirt. I tried not to be conscious of it as we walked into the center. We must have been quite a sight with our long legs, short skirts and stilettos clicking on the tiled floor. We were certainly attracted the attention of every male in the place and I heard the word sluts uttered by some of the women.

Our first stop was a lingerie shop. Mistress seemed to know the manager, a slim attractive young woman, as we were quickly ushered out back.

"So this is the new one I heard about. She's very pretty. What can I help with today?" asks the manager.

"She has just had a boob job and needs plenty of support but I hate the look of the sports bra. With the new size she also needs a whole range of sizes and colours as none of her old ones are going to fit. So how about a couple of sexy support bras to get her through the next week. A black one and a red one will be fine and then we will look at the longer term needs".

"Take off your blouse and bra so I can check you out" says the manager.

Soon I am standing in front of the naked from the waist up with the girl fondling my breasts as she explores their weight and shape. My nipples are quickly erect and my clitty is seeping again.

"I have the perfect thing" she says and disappears out to the shop.

Upon returning she presents me with a beautiful red bra with lots of lace trim but quite sheer in the cups. She helps me into it and asks how it feels.

"Absolutely wonderful" I gush. "It holds me really well but still looks and feels nice".

Looking in the mirror I see my erect nipples quite clearly through the cups. My cleavage is very deep and outlined well by the lace over the cups. Half an hour later we leave having tried and selected about six other styles, which I will graduate to once I am healed. I am wearing the red bra under my sheer blouse and my nipples are clearly visible to all through the flimsy material. I don't care as I am just so happy to be the new me.