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'.