Sissy Downfall Ch. 02

Story Info
My further descent into slavery.
10.7k words
4.19
113.4k
55

Part 2 of the 2 part series

Updated 11/01/2022
Created 07/04/2013
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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
davine
davine
232 Followers

Revised version. all characters are adults. Part two.

All Characters are over 18.

*

My new life at Mistresses mansion was quite pleasant most of the time. My duties were to be maid to the two mistresses. I helped them bathe and dress; hand washed their delicate garments, cleaned their bedroom and changed the bed clothes daily. Sometimes, if I was really lucky the young mistress would have me lick her to orgasm. She had the most fragrant tasty pussy that I had ever experienced. Sometimes she would alloy me to play with my clit as I served her and if really lucky I was allowed to cum. These were all wonderful tasks for a transformed sissy to perform. The feel of their soft lingerie kept me hard whenever I handled it. Often while doing the hand washing I would rub a pair of fragrant panties over my clit and cum all over the garment. I always made sure that all signs were washed away as I was sure that if I was caught I would be severely punished.

I was often punished for minor infractions such as not addressing my Mistresses correctly or being too slow to deliver their breakfast. I would be whipped severely for such infractions and be starved for the day. The cook often forced me to suck him or let him take me from behind. With my stretched pussy and new found deep throat skills even this was not too arduous except for his stench. What I really hated was to have to service the training dyke with her hairy smelly pussy smothering me.

The training dyke was a new addition to the household who had been employed while I was away in hospital. It was her duty was to maintain discipline amongst the maids and slaves. She was a massive woman at least six foot six tall with broad shoulders, massive thighs and large breasts. She usually dressed in a tight t shirt, wraparound skirt and running shoes. Often she would grab me, drag me to her room and force me to service her cunt. I would be thrown to the floor and she would squat over my face forcing her cunt onto my mouth while my nose was pressed against her filthy stinking bottom. She would hold my private parts and squeeze them if my performance was unsatisfactory. When satisfied she would throw me over her knee and spank me before sending me to clean my face, repair my make up and return to my duties. I could usually smell her juices in my hair until I could next shower. My Mistresses would usually punish me after these sessions as I was invariably late and they could smell her juices in my hair.

Sue: the downstairs maid and I had become firm friends and looked out for each other. Often at night one of us would sneak into the other's bed where we satisfied our lusts together. All in all I was enjoying my new life. Little did I know that every sneaky little indiscretion was being observed and recorded by hidden cameras in every room?

Sue and I enjoyed tormenting the ex bar tender. He had been transformed into a sissified castrated slave with huge breasts, puffed up lips, false teeth and piercings in every possible place. He was drugged with a hormone and sedative cocktail to keep him docile. Dresses in a restrictive corset, stockings and impossibly high ballet heels with his pendulous breasts and useless clit exposed his life was miserable. His duties were to clean the floors in the whole house. As his legs gave out quite quickly as he tried to walk in his impossible shoes, most of his life was spent crawling as he performed his work making his bottom an attractive target for a pair of mischievous maids with their feather dusters. Maybe it was the hormones, I couldn't be sure, but he often ejaculated when we tormented him. Well! Even nasty people should have a little fun.

At least once a week Mistress would organize a BDSM party similar to the one described in the first part of my tale. Sue and I would be required to serve the food and drinks to the guests and submit to any requests from the guests. Mistress Rebecca often attended these events and would single me out for some special attention in the dungeon. She delighted in using a different apparatus to torment me each time she visited. I had been stretched upon the rack, had my shoulders almost dislocated hanging from the strapado and scourged upon the cross.

The worst torture was to ride the wooden pony. This diabolical device was a wooden saw horse with a very sharp pointed top bar. The victim was forced to straddle this bar which cut into the tender parts between the legs as they were lifted into place and then left with their legs dangling so that all their weight was taken by both their pussy and bottom in the case of a female or by the clitty and bottom in the case of a male.

Mistress Rebecca chose this torture for me at one of the parties. She was dressed in black thigh high stiletto heeled boots; leather corset and thong which showed her perfect figure to the wonderment of all that gazed upon her. I was dressed in a very constrictive leather corset which left my breasts completely exposed, seamed black sheer stockings and six inch high heels. My clit was pulled between my legs and held in place with the ring in the head of my clit being attached to my buttock rings with a padlock. My silly little balls sat either side of my clit looking a little like labia. Leather cuffs were secured around my wrists, locked together behind my back and the secured by chain to a leather collar around my neck.

Mistress Rebecca led me with a dog lead to the pony and forced to straddle it. The vicious sharp bar was about a foot below my crotch. A leather belt with chains attached was buckled around my waist. The chains were pulled down, forcing me to bend my knees and hooked to eye bolts set into the floor. I was able to keep myself above the wicked bar for a few minutes until fatigue set in and my legs started to tremble and I was forced to sit upon the bar to take the pressure off my calves and thighs.

I screamed as the bar cut onto my clit and forced my tired legs to lift me away from the hell that stretched beneath me. I remember seeing girls taken off the pony with blood running down their legs after their ride. My legs gave away again forcing my tender parts back onto the bar. Tears were pouring from me as I moaned with the pain. I was able to keep lifting myself away from the pain for about ten minutes before my trembling legs gave out. My begging and crying annoyed Mistress Rebecca so much that she gagged me. I felt that my clit was being slit in two. I was sure that I could feel blood running down my thighs. Suddenly I felt pain in my breasts as Mistress slashed at me with a cane. This made me wriggle and jump causing even more pain and damage. I passed out.

Waking up some time later I found myself restrained on a hard wooden board with my wrists and ankles tied to the corners of the device so I was held with my legs spread.

Mistress Rebecca whispered to me "we have had to put a few stitches into your clit to close the damage up. It looks a little ugly but if I have my way with you that won't matter much."

What did that mean I thought? What was to become of me?

"I am negotiating with your mistress to purchase you. If it all works out I shall have your fate in my hands soon." Mistress Rebecca laughed as she said this.

Eventually I was released and managed to hobble to my room. After undressing I looked at the damage to my clit and it was indeed ugly. I fell asleep terrified of what was in store for me.

The following morning I took breakfast to my Mistresses. I was dressed in my maid's uniform consisting of heels, stockings, very short black dress with white apron and cap. My clit was restrained which was very uncomfortable after the torture inflicted at the party.

After I had served their meal, my Mistress ordered me to lift my skirt for inspection.

"I don't like the way your nuts poke out either side of your clit. You need to learn how to tuck them up into your body so you present a more feminine look. I have asked the trainer to teach you how to do it. If you fail I will find another solution." Both mistresses laughed as I hobbled away.

As I reached the foot of the stairs I was grabbed by the dyke and dragged to the dungeon. She threw me onto a hard table on my back and secured a wide belt over my stomach to hold me in place. My ankles were pulled back towards my bottom restrained so that my legs were bent up and out giving her access to my clit. Having released my restraint she forced me to hold my clit up against my tummy while she probed between my legs for the openings to store my nuts. Suddenly I was in extreme distress as one of my balls was forced into my body. I screamed and fainted. Some time later I awoke to find myself lying on the table with the belt and ankle straps undone and my clit pulled back into place between my legs. My whole lower body throbbed with pain. Reaching down I felt the smoothness between my legs.

"Now that you know it is possible to hide them it will be your duty to tuck them away each morning" said the dyke.

I wondered if I would be able to do this and was determined to keep them where they were from now on. For the rest of the day I struggled to walk around and perform my duties. I was so glad when the work day finished and I was able to hobble to my room and prepare for bed. Unfortunately as soon as I released my clit both of my balls popped out. I cried as I knew that I would somehow have to push them back in before I presented myself for work the following day.

At five am I awoke to the alarm, gave myself my morning enemas and showered. Lying on the bed I pushed and prodded my balls trying to push them inside. No matter what I tried they stubbornly stayed in their sack as the pain was too great for a stupid sissy like me to force them inside. I sobbed with frustration and fear of what my punishment would be. I was running out of time to be dressed and made up ready for work so I just had to get on with my daily preparations and go to the kitchen and wait to take breakfast to my mistresses.

My mistresses were waiting at their table dressed in translucent robes that barely hid their beautiful bodies.

"You are late slut" mistress snarled at me. "serve the food and then stand facing the wall while we eat."

I waited with trepidation trying to listen in on the whispered conversation between my two mistresses.

"Come here slut and present yourself for inspection" Mistress commanded.

I hobbled across the room and lifted the hem of my skirt. "Lower your panties" I was told.

My Mistress smiled at what she saw between my legs. "You have failed in the task I set you and will be punished more severely than you can imagine. Remove your panties, unhook your clit and spread your legs."

I complied. She reached between my legs and fondled my balls before squeezing them so hard that I fainted.

I awoke in darkness and pain lying on my back. My wrists were tied above my head and my ankles were tied and stretched tightly away from me. I realized that I was held on the rack. I could feel some kind of long plug on my bottom and there was a large penis gag in my mouth secured with a leather harness.

Suddenly the lights were switched on and my mistresses and the dyke were standing around me. Nothing was said as I felt the plug in my bottom expanding and heard a low hum form a compressor. I struggled to no avail as I felt my rectum expanding beyond belief. I tried to scream but of course only muffled sounds escaped around the gag. I heard the sound of the rack starting to stretch my body and soon felt that I must soon be torn asunder. When I felt that my joints were about to dislocate the stretching mercifully stopped. The dyke attached a chain to the ring in my clit and pulled it straight up and hooked the chain to a bar above the rack stretching it to its limit. I then felt a leather band being tightened around my scrotum to the point where I passed out from the pain.

Awake again I heard my Mistress whispering in my ear. "You have failed to learn how to tuck and were warned that I would find another solution. I could just leave that restriction on you until they fell off but I think that may kill you which would be a waste of all the money I have invested in you. Mistress Rebecca would love to buy you but I fear that her solution to your little boy problem would be to remove all of your genitalia. It has been my experience that such surgery often leads to incontinence and I would find you repulsive in a nappy. Another downside is that without the leftover skin it would be impossible to fashion a fake vagina if I decided that you deserved it .As I have a few other modifications planned for you I may as well have you surgically castrated at the same time. Hopefully this will put an end to some of your other little perversions that have been recorded by the cameras."

I felt a slight jab in my arm and slipped off into dreamland.

My next recollection was of waking in the same room where I found myself after my previous modifications. This time my throat and mouth were sore, there was a throbbing pain in my groin and my ankles were swollen and sore.

"The doctor will be in to check you shortly. You must rest for at least two weeks in bed for everything to heal." The nurse said. I tried to speak but nothing came out.

I was restrained in the bed for the two weeks with various tubes to feed me and for my voiding.

Eventually the big day arrived and the various dressings were removed.

"I guess you want to know what has been done to you". The doctor asked when he visited that day. "Well as you might have guessed your testicles are gone and we have done some other feminizing to you. Your Adams apple has been shaved so it no longer shows. I have modified your vocal chords to give you a higher voice. Your teeth have been removed and a set of fine dentures made. A few small changes I made to your tongue will make sure that you lisp as a sissy should. Of course the best thing I have done for you was to shorten your Achilles tendons. You will be unable to walk without at least six inch heels and even then there will always be some pain. A small price to pay for such enforced elegance I think. You may still get erections if the stimulation is strong enough and you will still emit some weak and watery juice if you come. You will probably just dribble the juice out if you get excited.""Now you may suck me off in thanks for all my hard work... I always like to be first to try my latest creation".

With that he dragged my head to the side of the bed and proceeded to fuck my mouth until he came. After I swallowed he put the dentures in my mouth and suggested that I should thank him for the feed.

"Oh thank you thir. "I lisped and was surprised that my voice sounded quite different even from inside.

The doctor left and the nurse helped me to sit up and swing my legs over the edge of the bed. She fitted some six inch pumps to my feet and helped me to stand. My ankles hurt a little but the pressure that I usually felt in my calves when wearing such high heels was absent. With the nurses help I was able to walk around for a few minutes and then rested to get my strength back. I was passed a pair of waterproof heels and told that I would have to wear these when showering.

"You should rest for a couple of hours. I will return to help you shower and dress. Your Mistress will be here to take you home once you are prepared. Soup and some water will be brought along shortly. Eat slowly as your stomach needs to become accustomed to food again."

I ate and rested. A gentle tap on my shoulder awakened me from a deep dream filled sleep where I imagined myself living in luxury dressed in the finest silks with servants and a handsome master whose only demand was that I serve him sexually.

The nurse fitted my shower heels and helped me to the bathroom where, on hands and knees I was administered a gentle enema. After I had emptied that one I was given several more until I ran clean. I showered and washed my hair. Once dry I sat at the dressing table, brushed my hair and applied my make up in the slutty, too much of everything, style that I knew my mistress liked her possessions to wear.

Lacing me tightly into a white corset with a quarter cup bra which left most of my breasts exposed the nurse then pulled my clit between my legs and laced the ring in its end to my two buttock rings and left me alone to finish dressing. One of the advantages of my new restraining system was that it left my bottom exposed and available which meant that I could be taken from behind without removal of the leather strap. I carefully rolled a white seamed stocking up my left leg and attached it to the suspenders on the corset making sure that the seam was straight. I then fitted the right hand stocking enjoying the feel as I slipped it over my leg. Six inch high white pumps were next and then I practiced walking while I waited for Mistress to arrive. My silly little clit twitched in anticipation.

There were no other clothes left for me and I wondered what outrageous outfit I would be expected to wear.

My question was answered soon enough as just then my Mistress arrived with the doctor. Dressed in clingy black dress that showed her beautiful figure to perfection she almost floated into the room. A sissy like me could never hope to achieve such beauty and grace. I curtsied to her and kept my head lowered as she inspected the surgeon's handiwork.

"Excellent work; I'm well satisfied with your modifications as always. I'm sure there will be plenty more for you to do in the future." Mistress laughingly said.

Grabbing me by one of my nipple rings, mistress asked me what I thought of my new self. "Oh thank you Mithtress I think all the changes are thrilling." I gushed.

"That lisp is perfect." She said and dismissed the doctor. "Here is the rest of your outfit." She said passing me a large paper shopping bag. "Put it on and we will go to the hairdresser."

In the bag I found a skimpy white sheath dress and some jewelry. The dress fitted me like a glove with the hem about half way between my knees and crotch it did at least cover my stocking tops except that there was a split that came up the left side to a stitch at the top of my leg and then three inch slits all the way to my waist. From that side it my stocking top was clearly visible and my lack of panties was obvious. The material of the dress was quite light and opaque around the waist and below but above that it was much more translucent so that my breasts were clearly displayed through it. There was a little girls pink Barbie shoulder bag for me to carry my make up. Earrings featuring silver penises dangling from them and a matching neck lace completed my outfit.

"What do you think of that slut?" Mistress asked.

"Perfect thithy attire Mithtress, thank you tho muthch," I replied.

"Not quite perfect. Pull the top of the dress down I need to make your nipples more prominent."

I slipped the shoulder straps down my arms and lowered the dress to expose my breasts. Mistress carefully painted some red liquid onto my nipples which darkened them considerably. She then blew on them to dry the paint. As it dried I felt a tingling burning sensation and my nipples became erect and hard. Pulling the dress back up I could see my nipples straining against the thin fabric which now seemed to irritate them with every move I made. Mistress smiled wickedly, spun me around and slapped me viciously on my bottom.

"Get a move on we have work to do to get you ready for a party we are attending tonight. If you are really good I might not paint some that nipple rouge on your clit and ass pussy." Mistress hissed at me.

I followed her through the door marveling at the way her womanly bottom undulated from side to side, down a flight of stairs and out to her mustang. I wished my bottom was more feminine.

davine
davine
232 Followers