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Sissy Downfall


This story is about my conversion from a cross dressing sissy to submissive transformed slut owned by Mistress Rebecca George. All characters are over 18.



Having been to the beautician for a full body and face wax I check into the hotel to prepare. The suite consists of a large living room and a comfortable bedroom with a large bathroom. The bedroom has a nice dressing table with mirror and stool. A full length mirror is adjacent. The king size bed is of an older style with metal barred head and framed foot. The living room has a soft leather couch, occasional tables, a desk with cane based chair with arms, and all the usual hotel comforts.

I carry my case into the room placing it on the rack provided. Quickly I divest myself of the drab clothes that I must wear daily. I admire the smooth hairless reflection in the mirror. This is my first full wax and I am pleased with the result. I select the outfit for the day and lay it out on the bed.

I fasten a white leather suspender belt around my waste. It is very tight and has a metal buckle on its back for attaching various restraints. I sit on the bed and unroll white lace top seamed stockings up my legs. Standing, I hook the suspenders to them and check for seam straightness in the mirror. Once satisfied I step into a white G string and slide it slowly up my legs and into place. I like the way the thong shows off my pert little bottom. A white push up a cup bra is next. It just manages to give the hint of cleavage as it forces some flesh out the top. I pull a sheer white camisole with lace trimming over my head and settle it over my bra. It is not very tight but hugs my body lines nicely. Sitting at the dressing table I apply heavy covering make up as a base. I use blusher to highlight my cheekbones, paint my eyelids with silver eye shadow and Shape my brows with a pencil. Bright red lipstick completes the make up. I am satisfied with the result. I look a bit tarty but not over the top. Silver clip-on earrings, bracelet and choker feel so good. I slip a tight white stretch mini skirt over my feet and stand to pull it into place. It just covers the lace of my stocking tops. Four-inch high white stiletto sandals and a blond wig complete the look.

I check myself in the mirror and feel a stirring in my panties I know this will spoil the look if I don't do something about it. Quickly lowering my skirt and G string I hook a white leather restraint to my penis and pull it between my legs and balls and hook it to the suspender belt. Once the G string is replaced a nice feminine line is achieved with even a hint of lips between the legs. It is not very comfortable but this is worth it for the correct look. After pulling up the skirt I reinspect myself in the mirror and know I am ready to meet you for the first time.

As there is a little time to spare I set up my digital remote control camera on a tripod, and focus it on the couch. I pour some white wine into one of the two glasses on the coffee table and sit on the couch to wait. The mini, of course, rides up exposing some bare thigh. A nice way to greet you, I hope. I take some shots of myself in various poses, some sluttish some demure, as I wait.

This day is a big step for me. I have been corresponding with Mistress Rebecca for some time since first seeing her on a photo sharing site. She is a goddess in pantyhose with flaming red hair. She has many gorgeous outfits which she loves to show off. I wonder what she will be wearing today.

I hear the sound of a key in the door and I get that breathless pounding feeling that I used to get when I first started dressing all those years ago. A feeling that has subsided with time and experience as I have become used to the look and feel of soft feminine clothes caressing my body. But this is going to be a whole new experience as it will be the first time I show myself to another person in the flesh rather than in photo on the net.

What will the day hold? I hope that it will lead to a dramatic change in my life. A possible step towards a new me.

You open the door and walk in smiling when you see me waiting.

"Ah, good, a camera," you say.

I don't stand to greet you as I am in awe of your beauty and wish to remain below you. You are dressed in a tight black leather halter neck dress. On your legs you have thigh length leather stiletto boots the tops just covered by the dress. Your make up is strong and striking as is your long red hair. Your gold earrings and choker contrast beautifully with the rest of the outfit.

Having placed a suitcase next to the door you walk over, pick up the camera remote control, then gently squeezing my shoulders you force me to stand. I am a little shorter than you. Pulling my head forward our lips touch and you force mine apart with your tongue. After an eternity you pull back and inspect. My lipstick is smeared as is yours you send me to the bedroom to repair the damage telling me that I may not serve you in that state. When I return you have also made repairs. Pushing down on my shoulders you force me to my knees in front of you.

. "Now," you say "I will teach you to serve like a real woman must ".

With that said you unzip you dress and remove it. Underneath is revealed your true self dressed in crutch- less panty hose with a pair of silken panties barely covering your bulge as it strains to be released. A black tightly laced corset completes you attire.

Pulling my head forward you say "Lick its length you slut". I do so and taste the precum that has soaked through the panties. Occasionally I hear the click from the camera remote and know you are keeping a record of all of this.

After some minutes of this you push me back and say "Pull them down you slut". I gently ease your pantys down your legs and expose IT in all its erect glory.

"Kiss it slut," you say. I readily oblige looking forward to another taste of the salty cum that I know and love having many times tasted my own in order to train myself. I run my tongue around the head savouring the smoothness and taste of it

"Open wide," you say as you grab the back of my head and force yourself into my mouth. Although I have practiced before with a dildo, I have always been in control. How deep will you force me to take it? Will I gag on it? Questions quickly answered as you slowly force the full length into my throat. I feel I am going to suffocate and so I gag, you pull back only to push forward again as soon as my spasm stops. I gag again. You pull back again and repeat the movement with the same result.

"You stupid slut," you growl "you will learn to do this'. Pulling me to my feet you lead me behind the couch and bend me forward over its back. My skirt rides up and my G string clad bottom is exposed. You can also see the bulge of my restrained penis in the crack between my cheeks.

"Don't move slut" You whisper as you walk towards the suitcase near the door. This, you move to a side table out of sight. I hear it open and some sounds as you rummage through it. Returning you drop a riding crop on the floor in front of me and grabbing my wrists force them behind me where you cuff them together. A gag ball is placed in my mouth and secured with a leather strap. You force my legs apart and they are kept that way with a bar with a cuff at each end locked onto my ankles. All through this I have felt my own pre cum seeping into the thong of my G string.

Noticing this you say "You are obviously enjoying this too much, perhaps some pain will cure you and make you realise that only my pleasure is important, and that yours will only come through serving me". Having picked up the crop you disappear out of sight. After what seems an eternity I hear the whistle of the crop through the air followed by an intense sting to me bottom. The sound and the pain are repeated many times and all I can do to try to protect myself is to wiggle my butt which just spurs you on even more. At last you stop.

"Are you ready to try again" you ask. I can only nod. You stand me upright and giggle as I hobble back to the front of the couch. I nearly fall as I kneel down. You check the camera focus, remove the gag and repair my lipstick for me. I wait at your pleasure.

"Open wide little slut and serve your mistress" You whisper. I comply, as I must. You slowly force your way into my mouth and over my waiting tongue. You pause to allow me to become used to the sensation and then slowly push towards my throat. You sense a contraction in my throat and pull back just enough. Then, when it has passed continue inwards. After a couple of these attempts, you achieve your first aim, to have all of it in my mouth and throat. Looking up I see you smile and hear the click of the remote. I am happy too, as I am now serving you well.

In and out, you now move it just as you would in my pussy if I had one. Again I feel the excitement welling up between my legs but I can only dribble as it is so tightly held in the restraint. Back and forth, you seem to harden and grow even more as time passes.

"Are you ready to taste my cum, you slut?" you growl. I nod as best I can. Smiling you pull back enough so that it will land on my tongue. I feel the head spasm and hear your intake of breath. Then glorious globs of salty goo flood into my mouth. I can't believe how much there is. It tastes so good. I swallow it to stop it overflowing my mouth and staining our clothes. Finally you finish and after one last push deep into me, which catches me by surprise, you pull back out. You stand awhile in front of me and I notice a drop appear from the end. I stick my tongue out to catch it and you push the head back in for me to suck the last of the treat out of you.

"You are really getting into this aren't you, my little cocksucker" you hiss.

"Yes mistress" I breathlessly reply. After unlocking my cuffs and the spreader bar, you send me to the bedroom to repair my makeup.

"You may also use the toilet if you need to but don't touch yourself or make yourself cum or you will be sorry," you say. I am tempted as I am starting to enjoy the punishment but do not as I need to comply with you will. On returning, I find you lounging on the couch with a glass of wine. A hard wooden chair with a cane seat is pulled up facing you about a yard away. You indicate that I should hitch my skirt up and sit on it. I do so and discover that the cane irritates my well-caned bottom and the hardness of the seat hurts my penis and balls where they are pulled between my legs. To relieve the pain I spread my knees a little.

"Stop wriggling and clamp those thighs tight you slut, I chose that chair to make you hurt some more".

Walking to your case, you pull some leather belts out and return. A long belt is placed around my thighs and pulled very tight. Another around my waist holds me to the chair back. My wrists are restrained by short belts to the arms of the chair. My bottom burns and balls are squashed. Tears trickle down my cheeks.

"That is what I wanted to see, my little sissy" You laugh.

"Is you mouth and throat dry after all that sucking" smiling.

"Yes mistress" I answer.

"Good "You laugh, sitting down and having another sip of the wine.

"Now you must sit and suffer silently while my cum is replenished ready for the next step in your fall to true sluthood. You may gaze upon my beauty, reflect upon what you have learnt and wonder what lies in store next. Be assured that it will not all be pleasurable".

"Oh, by the way did you give yourself an enema in preparation for this meeting?"

"No mistress I didn't have the equipment" I reply, head bowed.

Jumping to your feet you reach out and slap me across the face saying, "Did you think I would fuck your dirty hole? Fortunately I have a kit so that you passage will be squeaky clean for me to enter." You hiss at me.

For some reason the thought of you, giving me an enema worries me more than any other anticipated punishments. I hope you are gentle and don't try to over fill me or make me hold it for hours.

"Of course there are advantages in this enema for you slut. Do you know what they are?" You smile.

"No mistress I don't". I whisper head bowed.

"It is my custom to force my slave to clean me off with her tongue after I have filled her tight pussy. Sometimes I prefer to pull out and come again in her mouth. Either way I am sure, you will prefer not to be cleaning too much dirt off. Do you agree my dear little whore?"

"Yes mistress".

"There may be some pain involved in this operation, but it will be nothing compared with the punishment you will receive if you don't cooperate. I will probably use some lubricant when I enter you later if you have been a good girl, but I can guarantee that I won't if you resist my will". You whisper.

I can only nod my agreement so great is my fear.

Undoing my bonds you drag me to my feet and lead me to the bedroom telling me to remove the mini, G-string and the camisole. I comply quickly. You point to the bathroom and I walk in there. It is a large room with a full-length bath with shower, separate shower and separate toilet cubicle.

"Stand facing that wall and suck in your tummy. I want a before shot" Smirking.

I do this and you take a photo in profile from the door. Walking behind me you release the cock restraint from the back of the suspender belt. The belt swings between my legs as my cock returns to its usual position. When I start to remove it you slap me hard on the bottom saying "leave it on for now slut".

"Get in the bath and wait on hands and knees while I prepare the equipment. During the enema I will tolerate some low volume weeping and whingeing but if you scream I will gag you. Is that understood". You leave without waiting for my reply.

On your return you prepare the enema, filling the bag with warm water and hanging it from the shower rose. Having plugged it into my tight little hole you open the tap to let it run in. I am surprised at how large the tip feels in my hole.

"Tell me when this starts to hurt whore so I know when you are half full".

I feel my tummy getting heavier and the skin starting to stretch but no pain yet. In fact it is quite a pleasant sensation. Before long I start to feel uncomfortably full but no pain yet. At the first sign of pain I groan "Please mistress, no more I am full".

"Don't make me laugh bitch. The bag is only half empty. So you are only half way to true pain". You say, slapping my bottom.

As the weight of water increases so does my pain and I begin to sob." Please mistress, no more I can't take it".

You ignore me and increase the flow. It hurts so much that I can no longer speak. All I can do is weep.

Suddenly you pull out the nozzle end quickly replace it with a butt plug. You pull the cock restraint strap between my legs and, pulling it very tight and hook it onto the suspender belt. This makes sure that the plug will not come out. You help me to stand and climb out of the bath. I stand facing the wall as you take photos in profile to show my now distended tummy. The suspender has ridden up high in search of a narrower place to sit. This puts more than usual pressure on the restraint strap. I am in extreme pain as you force me to walk all around the three rooms slapping my bottom as we go. I notice my reflection in a mirror. I look pregnant. After several laps of all the rooms you lead me to the toilet, release the strap, remove the plug and sit me down. Ah, blessed relief as I drain out.

Closing the door you say "Come out when you are finished and we will give you your next flushing".

After wiping myself I am reluctant to leave the safety of the cubicle.

"Get out here you little sissy or I will make the next one even bigger".

I step out gingerly and climb back into the bath and prepare for more pain and humiliation.

"How many more will I need mistress" I ask.

"Until you run crystal clean. My guess is at least four more." You smile while preparing the bag.

I groan as you plug the nozzle in again and I start to fill again. The ritual filling, parading round and voiding is repeated over and over until you are satisfied that I am ready to receive you.

"Well done slut. You have held more each time. I am pleased with you progress. Wipe those tears away, repair your make up and come to me when you are ready to be ravished". You retire to the living area to partake of some more wine while I try to make good the damage to my make up. I reattach the restraint and slip my panties and skirt back on.

I join you. You allow me a small glass of wine which I drink politely while seated on the cane seat. My bottom burns, my hole is sore and my spirit is crushed.

"Stay there while I prepare the bed for your ravishing" you say as you walk to the bedroom.

I obey and contemplate my fate as I sip my wine and listen for any hints of what is in store for me in the next room. It is not long before you appear at the door and beckon me to come in. I finish the wine and walk gingerly to the bedroom where I find you standing next to the bed. The bed is bare, save for the base sheet and one pillow. Leather straps are attached to both the head and foot. You Indicate that I should lie down I comply and you cuff my wrists to the uprights at the head. Sitting down next to me you pull my skirt down around my legs and remove it. You lower my panties far enough to remove my restraint. You pull my panties back up to cover my now forward facing penis.

Having removed your dress and panties you straddle my chest saying "Now suck on my clit and make it big, hard and ready to fill you".

You force the semi erect member into my mouth. It is not long before you are stiff and filling my throat as well as my mouth. After some time you seem satisfied with my performance and pull out of my mouth. Climbing off the bed you grasp my left ankle and pulling it towards the bed head you force me to bend my knee so that the ankle may be attached to the strap fixed to the top of the bed head. You repeat the procedure with the other leg. I am now completely vulnerable to your advances. My wrists are tied to the lower portion of the bed head and my legs are pulled so far back by the other straps that my bottom is completely off the bed. My ankles are pulled well apart so that my hole is completely exposed when you pull aside my thong.

Disappearing out of sight I hear you rummaging around in your suit case. When you return you are wearing latex gloves and carrying a tube of lubricant. I sigh with relief that you are not going to take me dry.

You sit next to me and pull my thong aside. I suddenly feel a cold sensation round my hole as you liberally apply the lubricant. Next I feel a finger gently exploring my insides. This is followed by another finger and then another. I am starting to feel quite stretched. I hope you are not going for the whole fist. At the forth finger I start to whimper as It is becoming painful.

"Whimper and cry all you wish but only quietly or I will gag you. You may wriggle your arse too as that turns me on." You whisper.

Four fingers seem to satisfy you and you continue to work them in and out preparing me for the real onslaught which I know will shortly follow.

Your fingers are still inside me as you climb round my leg and kneel facing me in preparation for my penetration. Slowly I feel the withdrawal of the fingers. Your thighs are pressed against my buttocks. Once the fingers are out I feel the head pressing against my poor little punished hole and you are leaning right over me. The pressure increases and I feel my self stretching to accommodate you. Just when I think I can stretch no more I feel a sharp tearing pain and the tip is inside me. My tears flow readily and I beg you to go no further. Laughing you redouble your effort and push even harder. The pain increases as I am unable to relax sufficiently to allow your easy passage inside. Undaunted by the resistance you force your way further and further into me. I have never felt any thing this large and hard in me before. Finally, you are fully buried inside me and you start the journey back out. I am starting to relax now although the pain is still strong. Sensing this you begin the rhythmic back and forth movement which I associate with all good 'lovemaking'.





Although the pain is still there I start to feel the first small sensations of pleasure. My own little clitty is slowly dribbling its juices into the front of my panties. A most pleasant feeling seeps through me. I am starting to feel like I think a real woman must at the time of her deflowering. Pain and pleasure combine to give a feeling of peace. I am starting to feel like the real thing. I try to push back towards your thrusts in an effort to take you deeper and deeper.

Sensing that I am now converted to the slut you want you smile and concentrate on your own feelings and sensations.

I am no longer crying but breathing hard from the pleasure and exertion of pushing. Your breath is also laboured and is starting to get a little irregular.

"Please don't cum too soon "I cry out.

"I'll come when I please, bitch".

I can sense from your breath that you are near the end. I hope that I will come myself soon or that you will allow me that release when you are finished.

With an intake of breath you plunge deeply into me and I feel you explode inside me as your breathing becomes ragged. The head of my own stiff little clit throbs as I come into my panties.

Seeing this you scowl at me and slap me hard across the face saying "You have come without my permission. I will punish you for that later".

Pulling out of me you climb around and grabbing my head you force yourself into me saying "Now, clean me off you bitch".

I do as I am told, licking and sucking until all the salty cum taste is finished. I am glad for all those enemas as I can't smell or taste anything unpleasant.

You leave me like this for a few minutes and return with a wine and my camera. As you are photographing me I can feel you're cum slowly dribbling out and onto the sheet.

"The maid will be impressed with that mess. But I guess the blood with it proves you were a virgin". You laugh as you slap me repeatedly on each bottom cheek in turn.

After releasing my ankles you pull my legs and lower body towards the side of the bed so that I am lying next to the mess that has dribbled out of me and then re fasten both my ankles to one corner of the foot of the bed having first removed my soiled undies. I can see that there is indeed some blood mixed in with the creamy cum that has oozed out of me.

Carefully you use my panties to wipe up the rest of my cum from my belly and then stuff the whole lot into my mouth. Fortunately, as they are very brief, they don't choke me. A leather belt pulled tight around my head and across my mouth holds them in and creates a very effective cum gag. I am well restrained and can only wriggle around a little. I wonder what you have in store for me now standing smiling down at me.

Although restrained by both ankles and wrists I can still move my head around sufficiently to see most of the room.

You pick up my male clothes which I had folded neatly next to my case and my shoes and carry them into the lounge room saying "you won't need these again for a while". My car keys and wallet are in the pockets of my jeans. My heart pounds and I feel a cold sweat overtaking me as you laugh in the other room.

Returning you slide back into your panties and zip yourself into your dress. I sense that you are about to leave as you check your appearance in the mirror. "I am leaving you now. The maid will be along soon to clean up. I hope she is not too angry with you for the mess. I am leaving the crop, gag and restraints in case she feels like punishing you. The contents of the camera I am taking as evidence that you were a willing participant in all of this in case you try to claim otherwise'.

With that said, you leave the room and I hear the outer door open and then close behind you. I am alone, restrained and gagged. I am clad only in sandals, stockings, suspender belt, bra and camisole with my little clitty uncovered for all to see. When will the maid come? Will she be cruel or kind? Will she use and abuse me? Or release me and help me get home? Questions running through my head as I lie and ponder my fate for what seems an eternity.

Click. A key turns in the lock. My heart is beating furiously. A footstep louder as someone approaches.

A tall striking woman in her mid twenties appears at the door and pauses with a look of disdain in her eyes. She is dressed in low heels, stockings, tight black short skirt and white blouse. Long blond hair is tied back and her make up is subdued.

"Well. What sort of little pervert do we have here? And look at the mess it has left for me to clean up. I guess you hope I will release you and help you get home. Well that may happen. But it will only happen with your complete cooperation. Nod if you understand".

I nod vigorously.

"Good. I will now release you. Don't try to escape as I don't think you will get far looking like that. Imagine getting arrested and thrown in a cell full of crims and drunks dressed in only those things".

After releasing my bonds she helps me from the bed and takes forces me bend over the back of one of the chairs. "This is punishment for soiling the bed".

She whips me mercilessly with the crop until my bottom is once again completely covered in red stripes. Standing me upright she removes the gag, throwing the undies into a bin. "Now get on your knees and lick up the mess you have made on the bed".

I immediately comply and soon there is only a wet patch of saliva to be seen. "Now strip the bed and remake it with the fresh sheets from my trollFemdomousey. I spend the next half hour doing her bidding preparing the room for its next occupants.

When she is satisfied she inspects the contents of my case. A red G string is selected to replace the now discarded white one.

"Put on your restraint and these panties fix you make up and wait for my return. The room account has been paid and I will take you out of the building by the staff entrance. We will then go to my place so that I may toy with you some more. Although your type doesn't interest me sexually I will enjoy punishing you and having you wait upon me. I do have some friends, of course, who would love to come and play with you in a much more intimate fashion. I am taking your skirt with me as I don't think you will get far without it".

That said she leaves the room and I refit my restraint, slip into the clean panties and sit down to repair my make up. Having packed every thing back into my case I sit and wait for the return of my new tormentor once again pondering my fate.

After a half hour, wait the door opens and the maid returns, no longer dressed as a maid but in some very sexy street wear. She is braless and her nipples are visible through the light material of her little T shirt which is quite short and leaves her midriff bare above a very tight and short mini skirt. Both skirt and T are a pale pink. Her legs are clad in skin tone tights as stockings would not be covered by such a short dress. Pink stiletto sandals with 5 inch heels accentuate the length of her legs. Hair that had been tied back for work is now free to flow around her shoulders. Silver earrings and necklace complete the look. I am short of breath and my clit is stirring at the sight of such beauty.

She throws me my skirt which I slip on and adjust so that my stocking tops are covered. She indicates that I should turn about for her to inspect me which I do.

"Oh good those red panties show through the skirt as I hoped they would. Makes you look extra sluttish. Hope we get some interest in you on the walk to the car. You will do your best to wriggle that arse as you walk won't you".

"Yes. I mumble".

She slaps me on the bottom saying "Yes mistress is the answer I must hear or there will be much pain inflicted".

"Yes mistress". Eyes now downcast I say.

Picking up my case I follow her through the door and down the hall to the service stairs. I do my best to walk with that womanly swing to my hips. My companion has no such trouble as her shapely bottom easily rolls from side to side in a most provocative way.

Upon reaching the ground floor we proceed out of the stair well and down an uncarpeted hallway to the staff exit. A security guard looks up at the sound of our heels tapping rhythmically as we walk towards him.

"Hi Leslie who is the new girl?" he asks.

"None of your business, she's mine so leave her alone" my mistress hisses.

He opens the door for us and slaps my bottom really hard as I pass.

"If your tongue ever wears out licking her slit, and you want a real man inside you come back and see me". He leers at me.

I smile at him and follow my mistress down the dimly lit street towards the staff car park. A few youths whistle and make obscene propositions to us as we tap down the street. Finally we reach the car, a convertible Mustang. Climbing into the driver's seat she unlocks my door and I climb in throwing my case onto the back seat. The seats are low and our legs stretch out in front of us. Our skirts ride up our legs exposing, in my case, the tops of my stockings and a glimpse of thigh. I try to pull the skirt down in an attempt to retain some dignity.

"Don't do that, you slut, I want you on display for all to see. In fact I am lowering the top and taking you for a cruise in the gutter lane so as many people as possible can perve on you. I may even force you to blow a few men in the back seat to see if you have any money making potential".

"Oh please mistress, don't make me do that. I might catch some horrible disease" I plead.

"Well, if you are very good, I might just let you work from home where I can check the clients rather than pick up these street bums. Is that ok with you".

"I guess so mistress" I whisper in fear.

So, we go cruising along the nightclub strip slowly in the gutter lane. The striking look of the car and its driver attract glances from any male who sees us. Although my looks are not to the standard of leslies the sight of my lace top stockings, exposed thighs and hint of red G string visible through the thin and now stretched material of my skirt are enough to get me some favourable, if lewd comments from the men on the pavement.

Eventually Leslie drives out of the city and we head towards the suburbs and her house.





It is much further to her house than I suspected. We travel through remote suburbs and into an area with large houses set in spacious grounds.

"It must be a long drive to work each day at the hotel mistress" I comment.

"I don't work there you stupid slut. I am part owner with your cruel friend in the leather outfit. Remind me to punish you for presuming I was some sort of menial servant".

"Yes mistress".

We arrive at a property surrounded by a high wall and pull into a drive way with a gate.

It is opened by remote control and having passed through we approach the large house travelling a long drive way. Round the back we enter an underground parking area large enough for eight cars. My car is parked in the corner.

"Don't get encouraged at the sight of your car. You won't be driving it for a very long time if ever." She smiles.

We alight from the car and I follow her to a stairwell carrying my case. Up the stairs she stops and directs me into a small bedroom. There is a bed, robe, dressing table and an open door through which I can see a small bathroom. I open the robe and find a selection of outfits hanging. Maids, school girls and nurses uniforms are joined by a selection of more conventional dresses ranging from classy to tarty. There are drawers full of a range of under clothes, all of it sexy and skimpy. Bras, suspenders, panties, slips, camisoles, stockings pantyhose and corsets fill the drawers. Many pairs of different styles and colours of shoes are lined up below the hanging outfits. They all have very high spike heels.

"There is some compensation to your position to make up for the pain and suffering you will endure here" she laughs.

"Yes mistress" I whisper breathlessly. My heart is pounding with excitement at the prospect of dressing in these lovely clothes.

The mistress beckons and I follow her past a kitchen, a dining room and into a sumptuous living room. A beautiful young girl dressed in a pale blue baby doll night dress matching panties and high heeled sandals rises and rushes to meet the mistress. I assume at first that this is a daughter but the passionate greeting kiss soon dismisses that idea as does the sight of my mistresses' hand caressing the girls' bottom through the thin material of the panties. The kiss over the two of them turn toward me, arm in arm.

The girl is about 5 foot 4 in tall with long blonde hair. She has quite small breasts and nipples clearly visible through the night dress as is her hairless vulva. My clit strains against its restraint in response to her beauty. I dare not speculate upon her age.

"What is this that you have dragged home?" the girl asks.

"This is our new maid darling. She will wash our clothes and make our beds and do whatever else we wish" says my mistress.

"Can I punish it if it's naughty? "She says in a little girl voice.

"Of course you can, now go and fix your make up while I instruct the maid".

After she leaves the Mistress tells me to kneel in front of her to receive my orders.

"That was Sandra. She is mine. You will call her 'young mistress' and will do just as she says. If she wants her clit licked you will do it. If she wants to piss on you, let her.

If she asks for your clit inside her politely decline as if I find out that you have done that I will cut it off and feed it to you. Apart from that one thing that is forbidden you are her slave. Understood?"

"Yes mistress" I whimper.

Sandra returns carrying a riding crop and grinning wickedly.

Grabbing my hands the mistress pulls me to my feet and leads me behind a wooden chair.



Quickly the two of them bind me to the chair so that I am bent forward over its back with wrists and ankles secured to the arms and legs. My skirt has ridden up exposing my already striped and reddened bottom. I feel a cold sensation on one cheek as something is rubbed on my skin followed by the prick of a syringe puncturing my skin. I feel a cold liquid entering the muscle. It hurts.

"Just your first hormone injection slut. We will soon shape you like a real woman with these" says my mistress.

"Sandra will now whip you as punishment for suggesting that I was a maid at the Hotel. I will not gag you as we will enjoy your screams and there is no one to come to your aid out here.

The crop whistles through the air and I scream as it hits my bottom. The girl strikes again and again working her way down from the top of each cheek in turn to the exposed and previously untouched bare skin of my thighs. Finally, she lands one across both buttocks, which catches the tip of my clit as it nestles between my cheeks in its restraint. I nearly pass out. Fortunately the older woman realises what has happened and calls a halt to the whipping.

"Careful: my dear we don't want to damage that as some of our friends prefer their toys to be intact".

They release me and force me to sit on the hard seat revelling in my obvious discomfort.

"It is late and time for us all to retire" my mistress says." Tomorrow you will start work at 7am. Be dressed in your chambermaids' uniform when the cook releases you from your room. You will be perfectly groomed with wig make up and jewellery. You will wear your clit restraint at all times except when showering or on the toilet. The cook will give you your duties for the morning until we are ready to take over with your training. Don't stay awake to long trying on your clothes, as you will have a very busy and long day tomorrow. Above all do not play with your clit and make yourself cum. I will know and will punish you severely if you do."

I am led to my room and locked in. Apart from cum, I haven't eaten for some hours and am quite hungry. I hope they feed me at breakfast.

I take off all my clothes and leaving them in a pile in the corner shower myself. Once dry ,I try on the chambermaids uniform discovering that I will need help to lace the corset in the morning and then try to sleep with my bottom burning, my clit throbbing and my tummy rumbling.

Arising early and feeling very hungry I check myself for body or facial hair. Finding none I shower and prepare my make up. The pain in my bottom and clit has fortunately subsided so that I can sit at my dressing table and prepare for the day. Once satisfied that my face is suitably feminised I select the lingerie to match the maid's uniform .The uniform consists of a burgundy corset with a white translucent short skirt attached to the bottom of it and a high neck blouse in the same material above it. There are strong laces to close the corset at the back and buttons up the back of the blouse. I will need help with both of these.

I chose a pair of seamed white stockings which I slide over my legs. I fasten my white leather suspender belt from the previous day around my waist. It is the only one with a fastener for the restraint. I attach the stockings and restraint and then slide into a pair of white lace panties. The bra I choose is skin coloured and like all the others in the drawer is perfectly padded so that it pushes what little breasts I have upwards so creating the illusion of a cleavage. I find a beautiful pair of white pumps with five-inch heels which I slip into and parade around in to get used to them. Silver earrings, necklace and my blond wig complete the preparation. As it is nearly time to be released I step into the uniform and admire my image in the long mirror while I wait.

The skirt is full and flows around my hips as I sway in front of the mirror. My panties, suspender and stocking tops are just visible through the thin material. The blouse attached to the top of the corset is high necked with long sleeves. My bra is visible through it but as it is skin coloured looks a little like bare breasts. I am quite happy with the result and look forward to the arrival of some one to lace me up.

A key turns in the lock and the door opens revealing a tall woman in a white cotton uniform style dress, white stockings, flat lace up shoes and a blue checked apron. In a deep voice she announces that she is the cooks' assistant and is here to lace me up.

Leading me by the wrists she takes me to a bare wall in the bedroom and forces me into the traditional frisk position with hands against the wall above my head height and legs spread. Taking the end of the lace she threads it through the holes of the corset.

"Breathe in deep you bitch and I will give some shape to your body".

With that I feel the lace pulling the corset back together. I breath in and find my tummy being pulled in as the lace is pulled tighter and tighter. There is some discomfort but no pain as I feel my insides squeezed upwards against my diaphragm reducing the space available in my chest. Once the lacing is finished I find that I am restricted to short breaths. I hope I can get used to this feeling. Once the buttons on the back of the blouse are done up I am allowed to walk to the mirror to inspect my new look. I am surprised at how shapely I look. The assistant is standing close next to me and I feel a hand on my bottom fondling me cheeks and running a finger over the head of my clit which immediately responds with a dribble of pre cum.

"You like that don't you slut? The cook doesn't want you just yet and told me to enjoy you while we wait".

I try to move away but find my arm in a vice like grip.

"I am much stronger than you and will hurt you unless you submit to my will" she hisses.

Forcing me to follow she leads me across the room until she is backed up to the stool at the dressing table. By pressing on my shoulders she forces me to my knees in front of her. After removing her apron she unfastens the buttons on the front of her dress and sits down. As I had suspected there is the telltale bulge of an excited clit straining at the front of the French- knickers she is wearing. The panties are loose fitting so she has no trouble in pulling them aside allowing her clit to be exposed through the leg hole. I am relieved to see that it is not huge. It looks to be a comfortable mouthful.






"Well girl, don't hesitate. You know what is expected. Get on with it".

I lean forward until my lips touch its head and run my tongue all over it savouring the pre cum coating it. Slowly I move forward wrapping my lips around it and sliding down its length until the tip enters my throat and I have its full length inside me. I slide back along its length very proud of my new found ability to take the length into my throat. Back and forth I move my head and sucking as hard as I can all the while. Soon I hear an intake of breath and feel a spasm through the length of the clit. I position my mouth so that the cum will land squarely on my tongue. Large globs of yummy cum overflow my tongue and flood my mouth forcing me to swallow in order not to spill any. I continue to suck until the last drop is extracted and the pull back to release the deliverer of my feast to the open air.

"About time you finished little girl. Now it is my turn to feed you some breakfast" a deep voice growls from the doorway. Spinning my head around I see a huge bear of a man standing in the doorway smiling wickedly. He is dressed in white pants with a chef's tunic above them.

The assistant hurries out of the way and is replaced by the chef standing before me as he unzips his fly and slides his pants and under shorts down his legs

.

"Oh my god" is all I could say as before my eyes was the biggest cock I had ever even imagined. In its semi flaccid state it was two inches thick and ten inches long. How was I ever going to suck this monster? He sat down and gripping it in his let hand, lifted it up and presented it to me while pulling my head forward with his right.

I opened my mouth wide and just managed to get the still soft head between my lips. Feeling me hesitate he forced my head slowly forward so my lips slid down the shaft. It reached the top of my throat and could go no further. Over half its length was still outside my mouth. The pressure was released from my head and I was able to slide back off it until only the head was still in me. My head was once again forced forward until I could take no more. The monster was starting to harden as I once again pulled back. I could feel my lips stretching tighter and tighter. In the background I could hear the assistant giggling.

I was pushed down onto it again and it grew again as I pulled back. I felt that the corners of my mouth were splitting. My mouth was completely filled with it and I could not suck as my cheek muscles were stretched to maximum. I hoped that he would soon cum as I didn't think I could take much more. After a couple more strokes it seemed to have stopped growing but not before I tasted the salty taste of blood in my mouth when one corner of my mouth split open. Back and forth I was forced to go for what seemed an eternity until finally he held still with just the tip in my mouth and I felt it spasm on my tongue and then flood my mouth with his seed. I couldn't swallow fast enough to contain the huge quantity and some slipped past my lips and oozed down his shaft. Once drained he pulled out and said "Lick the last of it off me you clumsy girl".

I ran my tongue along its full length until it was clean and then sucked the last drops from the tip.

He stood, pulling up his pants as he did so, saying "Fix up your make up and join us in the kitchen in five minutes".

I was left alone to dab the blood from my mouth and re apply my lipstick. This done, I left the room and headed to the kitchen I found that due to the height of my heels, I could only take short steps. I felt quite weak both from a lack of food and from the tightness of the corset.

"I guess you would like some breakfast?" the cook asked as I entered.

I nodded.

"You are not allowed to eat until you have delivered the mistresses their breakfast" he said. "Sit over there while we prepare their trays".

I sat and waited thinking that all I had eaten in the last twelve hours was cum.

Eventually the trays were ready. The assistant took one and I the other. I followed her along the hall to a flight of stairs which I climbed very carefully as I was fearful of falling. After knocking on a door we were summoned into a sumptuous bedroom.

The two mistresses were seated at a table on a covered balcony overlooking the garden. They wore matching translucent white wraps and white high heeled slippers and nothing else. Their naked bodies were displayed clearly through the thin material.

"About time you arrived" said the mistress.

"Sorry Mistress" said the assistant "but the maid insisted upon sucking all the kitchen staff dry thus delaying the breakfast.

Both mistresses laughed at this. "Don't worry dear. She will be punished for her greediness".

We unloaded our trays onto the table and the assistant was dismissed.

"Kneel down here beside us while we eat, maid" the mistress ordered.

I did so and soon found the tiles to be quite hard on my knees. My stomach rumbled at the smell of the croissants that they were eating.

"Are you hungry maid? I thought all that cum would have filled you." They both laughed.

"Yes mistress" I replied looking at the floor.

"We don't want to over feed you because from experience I know that large doses of hormone tend to increase weight. Therefore, we will restrict your intake to compensate. They tell me that cum is high in protein". They both laugh again.

"If you beg like a dog we will give you some scraps".

I put my hands up and pant pretending to be a dog.

Both Mistresses turn in their chairs and face me with their knees spread exposing their slits to me.

Breaking off a piece of croissant the mistress says, "These taste a bit plain for a begging sissy like you. I think a little woman juice is needed to add some spice".

With that said she wiped the morsel deep through her slit and through it in the air for me to catch. I caught it well and eat it quickly enjoying the spicy taste.

The young mistress repeated the procedure but made the catch much harder so I missed it and it fell behind me.

"Eat it off the floor, bitch". The young one said.

I turned to do so and was kicked hard in the behind so I nearly landed on my face. I picked up the food with my mouth swallowed it and turned to see my mistress pull a piece of croissant out of her cunt. It glistened with here juice. As she threw it on the floor for me to retrieve my younger tormentor pushed a slice of toast inside her.

After I had eaten the one off the floor the young mistress leaned back and indicated that I should eat the toast straight out of her hole.

The toast was sodden with juice but tasted fine. Seeing this trick my mistress followed suit end I spent the next half hour eating from their pussies.

Eventually they tired of the game and I was told to stand and receive my instructions.

"Firstly you are to pick up all our soiled clothes from yesterday and take them to the laundry. Latter when you have time you will wash all the delicate clothing by hand and the rest by machine. After drying you will iron those that need it. You will wash your own at the same time. Mid afternoon I have arranged for you to receive some training in some womanly arts such as make up and deportment. You will receive your hormone injection at this time. This evening I have friends coming over for dinner and you will be a French maid and serve them for the evening. After your training session you will have some time to prepare for the evening. You will give yourself several enemas in case some of my friends decide to use you in that way. Then you will dress yourself and get the kitchen slut to do the final lace up. Be ready to greet the guests at seven o'clock and bring them to the lounge room. Now go and get a tray and clear the table".

I picked up the dirty clothes and took them to the laundry. Picking up a tray from the kitchen I returned to the bedroom to take the dishes away. The mistresses were on the bed in sixty nine position busily licking each others slits. They ignored me as I cleared the table and left.

I left the tray in the kitchen and was about to leave when the cook said "Don't go just yet I want to adjust something on your skirt".

He showed me four small hooks around the hem of the skirt and corresponding loops at the base of the corset. This allowed the front, back or sides of the skirt to be held in raised position giving easy access to whatever part of me was desired. He hooked up the back of my skirt exposing my panty clad bottom which he slapped hard as he sent me on my way to start the washing.

I put the clothes on to wash then hand washed the bras, panties, suspenders and stockings by hand. The cook managed to slap me on each trip through the kitchen.

Each trip through the kitchen is a nightmare as I am carrying a clothesbasket, my scantily clad bottom is exposed and I have no way to protect myself.

The weather being warm, most of the clothing dries quickly so I carry a load to the laundry for ironing. Having placed the basket on the floor I am startled to find the kitchen hand, Sue, has followed me. Putting her arms around me she pulls me close and kisses me deeply. Her tongue probes all through my mouth as she draws the kiss out for an eternity. I feel her hand slide over my bottom until it finds the tip of my clit. She caresses the end of it through my panties running her fingers over the slippery head. Next, I feel her hand inside my pants insistently kneading and massaging the clit tip until I know I must cum soon.

"Stop mistress has forbidden me to cum without permission and will punish me if she finds out'. I whisper.

"That's your problem, not mine" Sue snarls cruelly as she turns me away from her and bends me forward over the washing machine.

Pulling my panties down she kneels behind me, takes the head of my clit into her mouth, and sucks hard. My restraint stops her getting any more in her mouth. My clit is emitting a continuous dribble of juice and my breath is coming in short gasps induced by the constant leakage. Restricted, as it is in the restraint, the clit cannot swell as it wishes but tries to stiffen anyway. Suddenly I can hold it no longer and what little cum left after the continuous dribbling squirts into Sues' mouth, which continues sucking until the last drop, is swallowed. Standing up she gives me a vicious slap on the behind and leaves silently.

I kick my wet panties from around my ankles and throw them in the dirty washing basket. Then, trying to run, I head to my room to repair my lipstick and replace my undies. My high heels and tight lacing makes running impossible so I make an easy target for the cook as he chases me repeatedly hitting me with a long handled spoon.

He stops chasing me at the door and I escape to my room.

Once in the relative safety of my room I look through my panties drawer and select a pale pink pair of bikini briefs. After removing my shoes with the impossibly tall heels I slip the fresh panties on and put my own sandals on, with the more manageable heels. I unhook the skirt hem from the corset hoping that the change to lower heels will make me fast enough to evade the cook.

I repair my lipstick walk quietly to the kitchen and gingerly peek round the door. Sue is nowhere to be seen and the cook has his back turned. I make a dash for it and reach the laundry uns**thed.

I have just started ironing when I hear a sound at the door. Turning I see the cook advancing carrying a leather strop and a plastic shopping bag. Grabbing me firmly he forces me to the washing machine and bends me forward over it. I fear the worst.

"So you think you can evade me, slut. Well I will soon slow you down. Don't move or I will cut your clit off."

Kneeling behind me he attaches a leather cuff to each ankle. There is a short chain between them. I know that my steps will be very short now. Next he pulls my panties down and I feel something hard forced into my bottom. The object is cone shaped as I feel it gets larger the further in it goes. I am stretched to the limit until suddenly it is inserted fully and I close behind it only now feeling a small diameter tube through my hole. I do feel rather full inside. I realise that he has fitted me with a butt plug. He steps back and I hear the swish of the stop as it races toward my naked bottom. Then the pain starts as over and over he whips my already punished bottom. I scream and try to run but am so slow with the chain between my ankles and the feeling of fullness in my hole that I make a very easy target. Once I am crying uncontrollably he stops.

I sink to the floor sobbing. He stands over me laughing loudly.

"Better get on and finish the ironing as the mistress will call for you soon".

I iron for about a half-hour and am nearly finished. I have at last stopped crying but I know I must repair my make up before I go to my mistress.

The cook appears at the door and says "Go and fix your make up. I will have a tray ready for you to take when you return. Taking short steps, I head to my room only receiving a playful slap as I pass.

The make up repair takes some time as the tears have made a real mess. I return to the kitchen to find a tray loaded with sandwiches, cakes coffee and soft drink.

"Take this down stairs to the play room. It is through the black door in the garage." The cook says.

I take the tray and when I reach, the stairs find that I have to take one step at a time, as the chain between my ankles is only just long enough to allow this.

Upon reaching the door I place the tray on a low table next to it and knock. I hear muffled screams from inside, which get much louder as the door is opened by the young mistress. I pick up the tray and enter a well-equipped dungeon like room. The screams have been replaced by sobs. I place the tray on a table just inside the door, which is shut behind me. Surveying the room I see a selection of hooks chains rings and other devices set into or hanging from the far wall. A rack is set up over near the right hand wall and a large selection of whips; crops and other torture tools hang from the left wall.

In the middle of the room is the source of the sobbing. Now dressed in super high heeled white pumps, white stockings hooked by suspender straps to a tight corset which leaves both her clit, bottom and breasts exposed hangs Sue. She has obviously been having hormones for some time as she has quite well grown breasts. Her arms are pulled up toward the ceiling by a rope through a pulley so that her feet just touch the floor. Her left bottom cheek has red stripes from being whipped.

The mistresses are dressed identically in black leather. Thigh length boots over stockings suspended from leather corsets with metal studs accentuate their beautiful figures. Their breasts are bare and they wear brief black G strings to cover their slits. Their menacing beauty takes my breath away.

"Sit over there and watch what happens to girls who defy me" my mistress orders. Pointing to a high backed wooden chair with arms and studded leather insets for back and seat, positioned near the rack. Various leather straps are attached to parts of the chair. The seat is saddle like with a raised ridge in the middle.

I hesitate when I see how sharp the studs on the seat look. A quick slap on my behind gets me turned and seated very quickly. The studs are not sharp enough to cut but dig into the skin quite painfully. They irritate my already punished bottom and stick into my clit and balls through the thin material of my briefs. The raised centre increases the pressure between my cheeks forcing me to spread my knees to relieve the discomfort. The relief is short lived as I am quickly secured tightly with leather straps which allow no movement and increase the pressure of the studs against my delicate parts.



"Do you know why Sue is to be punished?" I am asked.

"No mistress".

"Watch the video screen and tell me which episode has caused her downfall".

On the screen a series of clips are played. The first is of me sucking firstly Sue's clit and then the cooks cock. Next we see Sue fondling me through my panties and then sucking me to climax.

When the screen goes blank I say "is it the last scene mistress"?

"Of course it is, you slut. Didn't I say you would be punished if you climaxed without permission?" she asked, and then slapped me hard on the face.

My mistress steps back and folds her arms under her breasts. I am in awe at her beauty.

"I know Sue forced her attention upon you and that you protested to stop her, but I could see you enjoyed it and didn't struggle very hard to stop her. You will soon realise that, in your position, any pleasure will be matched with an equal dose of pain. I am sure that the punishment will soon be looked forward to as you come further under my spell and become more female than male." She smiles and turns toward the sobbing Sue, who, seeing her coming starts to struggle against her restraints.

Her words to me are strangely calming and the discomfort I feel between my thighs seems to reduce as I watch the beautiful forms of my mistresses as they glide about the room with their bottoms undulating and breasts jiggling. I wonder if I will ever look a little like they do.

"I think we will move our attention a little higher on her body" my mistress says to her young consort as she pinches Sue's nipple between her long ruby nails.

"Oh please, no" pleads Sue.

"Oh yes. Can I do it?" asks the young mistress rubbing a bamboo cane gently over her own pubic mound.

"You have been a good girl lately so you may start on her. Only on her left breast though. Save the other for me." My Mistress smiles.

Without hesitation the young tormenter swings and lands a perfect slice across the top of the breast. Sue screams and the sound of the next blow is unheard. The mark left, however, is easily seen directly below and parallel to the first.

"Beautiful shot. See if you can keep them all so neat and tidy. You are learning well my little lover."

Thwack. Another lands in line with the last as she works her way down the breast toward the nipple. Her accuracy is amazing considering the struggle Sue is mounting against her bonds.

"Don't hit the nipple as I have a special treat in store for them" shouts the mistress above Sue's frantic screams.

The next blow bypasses the nipple and she continues to colour the lower portion of the breast.

Finally her work is done and she steps back to survey her handy work. She giggles and gently rubs a finger between her legs over her clit. The gusset of her panties is wet with her juices and a shine is obvious on the inside of her thighs above her stocking tops.

Sues breast is completely red save for a narrow stripe across her nipple. She sobs uncontrollably as she hangs against her restraint.

"What are you planning for the nipple?" asks the youngster with a wicked grin.

My mistress holds out her hand. In it is a small metal device with four metal prongs clamped together. When she squeezes the back of the device the prongs pull apart allowing them to clamp onto a small item. Having spread the prongs she positions it over Sue's nipple and let's go. Sue sucks in her breath as the prongs bite into her soft pink flesh. There is a small ring attached to the end of the device.

"It doesn't hurt too much yet as the prongs are not too sharp but wait and see what happens when I hang this weight from it" mistress comments to her companion.

Mistress hangs a weight from the clamp. The prongs bite into the tender flesh. The nipple stretches to twice its length. Sue's eyes bulge and she screams.

After some minutes she calms a little.

"If she keeps still the pain subsides. But watch what happens if she struggles".

She pinches sue hard on her other nipple causing her to struggle. The weight starts to swing causing Sue to scream again from the pain.












"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 whi

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SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

2 years ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

2 years ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
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Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
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Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

3 years ago
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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

2 years ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

4 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA....

4 years ago
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Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

3 years ago
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Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

3 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

2 years ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

4 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

2 years ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

4 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

4 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - By: Beverly Taff List of Characters. Me, Michelle: A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Doctor Shirley Williams: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine, AKA. Uncle Penny: My transvestite uncle. (Aunty...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

4 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie Jamie, ...

2 years ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
2 years ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

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