Training a Sissygurl Annie

By ac.oohay@amrak_tnatiseh

Published on Apr 11, 2020

Authoritarian

Stucky Peters and Norton Conner had worked together at a hardware store 15 years ago and had kept in touch largely because they shared one particular interest that was worth keeping under wraps Ð they were both driven sexually by young, slim, smooth, sissy-boys that had been trained as gurls to service older dominant perverts. Unfortunately for Stucky, he had never really been able to live out his fantasies for real as his wife Brenda had been from a very straight-laced Baptist upbringing. Norton, on the other hand, had married Sonja, who was a stout and austere German immigrant who had kept his house, kept his bed, and been an efficient housekeeper for the length of their married life. She had however with Norton's persistence in trying to convince her, come around to see the benefits to her from the plan that he had now set into motion with his friend Stucky.

Neither couple had been able to have children of their own, and while Stucky and Brenda had fostered a number of kids over their lifetime together Norton and Sonja had remained alone. This was of course about to change. Three of Stucky's foster children had been girls, and he proved to be a capable foster father looking after all of them until it was time for them to move out of his house. It was because they had been such efficient foster parents in the past that the agency had asked them three years ago to take on a teenage orphan named Andy who had bounced around the foster system and needed a stable home. Brenda had been only too happy to agree but Stucky was reluctant feeling that they had already done all that they could as foster parents. Deferring to his wife in the end, they agreed to take Andy into their home until he aged out of the foster system. A today was Andy's eighteenth birthday, that time had now come.

The two friends ambled out onto Norton's gravel driveway as they chatted about old times, as well as for Norton a look forward to new and exciting times ahead.

"I can't thank you enough for this my friend" Norton said as he slapped Stucky on the back. "This is like a dream come true for me, and I'm just sorry that you were never able to make it a reality for yourself at home." Stucky shrugged his shoulders and told his friend that at least one of them was going to be able to live out that lifelong dream, and simply asked that Norton send him pictures and videos on a regular basis. As they reached the car Norton assured Stucky that he would do just that, and Stucky pulled open the passenger side door. Norton grinned from ear to ear.

Andy was fast asleep still under the influence of the drugs that Stucky had laced his water bottle with when they left the house. Stucky had assured the foster agency that he had lined up a very suitable job for Andy now that he was legally an adult, and that they no longer needed to worry for his future. Similarly, Stucky had told an excited Andy that he was delivering him to where he had lined up a permanent position that if he played his cards right could be permanent. It hadn't been a lie, but the full truth was not what Andy had assumed his foster father had really meant. As the two men stood looking at the sleeping eighteen-year-old, Norton happily handed over the envelope of money to his good friend now that he could see with his own eyes what he was purchasing for the ten thousand dollars in cold hard cash.

Andy was slim and small for his age standing 5'4" tall and weighing 130 pounds. He was slight and skinny with thin limbs and very pale, almost alabaster skin. His hair was dirty blonde and while not yet nearly as long as it would ultimately become, it was down to his shirt collar which along with his pouty pink lips gave him a distinctly androgynous almost feminine appearance. He was wimpy and physically weak, two attributes that would be cultivated and groomed to become even more pronounced until he was nothing but an obedient and simpering little sissy doing the bidding of his new Mommy and Daddy without question of hesitation.

With the unconscious Andy slung over his broad shoulders, at 68 Norton was a healthy and strong man who could easily handle his new slave's lightweight body, he waved goodbye to Stucky who drove off down the long gravel driveway back towards the freeway. Norton entered the house, locked the door, and descended the stairs into the basement to where everything was set up and waiting for Annie's new life to begin.

"Hallo?" Sonja called as she came through the door hugging two paper grocery sacks tight to her ample bosom. "Are you home Norton?" she inquired.

"In here, dear" Norton replied as he got up from his chair and made his way to meet his wife in the kitchen.

After exchanging a couple of pleasantries and some discussion about how the traffic had been on the way back from the store in the nearest town, Sonja asked the inevitable question of whether or not Stucky had come over as planned.

"You bet he did honey and believe me he did not lie! You're gonna be really pleased when you see her. I've got her set up downstairs just as we planned, and once we have her properly trained in the basement we can give her the run of the house and start living life the way we were meant to from now on."

Not being able to wait any longer Sonja suggested that they both go down to see their new gurl, asking Norton if he thought she would be awake by now. Sonja did not need her husband to answer as he freed the padlock and then unbolted the door to the room where Annie was being kept in the basement. As the door swung open the couple stood side by side just inside the room looking at their new prize. Annie was naked on the single mattress which occupied a wrought iron bed frame, a thick leather dog collar fastened tightly and locked in place around her neck. A heavy chain connected the collar to a strong steel ring on the wall behind her, and the captive's hands were bound behind her back with her ankles also being shackled together. There was a large bright pink silicone ball gag jammed into her mouth propping open her jaw so widely that she was in quite a bit of pain, and she was drooling all over her lily-white hairless chest. Visible between her slender thighs was a shiny stainless-steel chastity cage that encased her tiny sissy-clitty. This was an element Sonja had insisted upon. She alone wished to be in control of her new gurl's clitty and planned to make that total control a key element to the training that would make Annie more responsive, more obedient, and eager to do whatever Mommy ordered her to do without delay.

Andy was terrified. He had awoken about twenty minutes earlier, groggy and confused and for some reason unable to move with his hands fastened behind his back and his ankles locked together. Only then did he also become aware of the constriction of the collar around his neck, and the large object stuffed in his mouth and buckled behind his head. He was as yet unaware of the metal cage on his penis, and had slowly been shaking off the effects of the drugs he had been given by his foster father when he heard the sound of people outside of the doorway to the room he was in, and the locks on that door being undone and removed. The door swung open and in walked an older couple. A very tall broad-shouldered man accompanied by a shorter, stocky, austere looking woman with very large heavy breasts. He gazed wide-eyed at the couple who simply smiled back at him with a pair or grins that chilled Andy to his core. He tried to mumble for help and for release from his bondage through the ball gag stuffed in his mouth. Both please fell on deaf ears.

The mumbled plea for help had barely left the captive's mouth before Sonja was looming over the bedside and had delivered the most vicious slap across the sissy's face. The crack split the air, and after just a brief second Annie's right cheek began glowing bright pink.

"Don't you EVER utter a word in this house again without permission, you naughty little slut. Your Daddy and I will let you know if we ever want to hear anything out of your mouth and unless you've been given that permission you'd do well to remember your place and keep silent in the presence of your betters, gurl!"

Gurl? Gurl? What did this woman mean by what she had just said? And who was she? Andy was so stunned by the swiftness with which he had been struck that it didn't even occur to him to allow the pain from the slap to register. She had referred to him as a gurl, and to themselves as his Mommy and Daddy? What the hell was going on here? The last clear memory he had was that his foster father had driven him to start his new job and now he was chained up and collared with these two old people seemingly having kidnapped him and locked him in bondage.

It was at this point that the older man stepped forward, and calmly but ominously announced that maybe a little bit of an explanation was in order, to clarify the realities of his new life. The life he would now lead as their little sissy-gurlÉtheir propertyÉand their slave. Emotions then ran from disbelief to anger to panic and finally to despair as Norton carried on with his explanation.

"The man you have known as your foster father is in fact an old friend of mine, and he and I share a common interestÉhaving skinny little femmy-boys like you turned into sissy-gurls to be used for sex, and slavery, and whatever else we decide to do with them. He could never do what needed to be done in his household to turn you into the sissy-bitch you were always meant to be Annie, because of your foster mother. In this house however, you will always refer to me as Daddy, and to my wife here as Mommy. We've bought you from your foster father and he left you here drugged unconscious for us to do with as we like. We're going to train you and transform you Ð make you into a very obedient little slut. Your new Mommy and I have big plans for you Annie, and if you're a good gurl we'll make it as painless as possible. If you fight us you will suffer greatly, and still end up as a simpering little fem, so I would advise you work hard, do as you're told, and focus on pleasing us and doing everything we tell you to do with a smile on your face."

Andy couldn't believe what he was hearing. It felt like a nightmare, but he knew that he was awake and that this crazy old man was realÉas were the chains, the shackles, and the ball gag in his mouth!

"To start with, we've decided to name you Annie. Your Mommy and I don't much care about what you used to be called and if we ever hear you utter your old name out loud you will get such a whipping that you won't be able to sit down for a month. Your name from now on, is Annie. You are a young teenage sissy-gurl who needs a Mommy to train her to be obedient and submissive around the house, and a Daddy to use her as a cumslut-whore for his pleasure. Luckily for you we are just such a Mommy and Daddy. Now, I'm going to take that gag out of your mouth Annie, and all I want to hear you say is a great big thank you to your Mommy and I for taking you in as our gurl, and I want to hear you beg us to make you into the most perfect little sissyslut you could possibly be. Think long and hard about saying anything other than that because there will be hard lessons for you to learn in the future gurl, but this doesn't have to be one of them."

Eight months passed with Annie kept in the basement bedroom, slowly being brainwashed and trained, remolded from a slender and small but definitely straight young adult male, into a sissified fem-gurl. Norton and Sonja had used many methods to break their sissy's will, and both of them were very happy with the results so far. Annie still needed reminding every so often of what she was, and why she existed, but basically she had been converted into a willing slave object for Norton and a select few of his friends to use for sexual pleasure, and for Sonja and two of her friends to humiliate, punish, abuse, and train as a genetic male who was weaker, smaller, and subservient to them as dominant females. Sonja especially liked to abuse and dominate Annie to keep her perpetually in some amount of fear - something Sonja felt a slave should always feel when they were truly an owned piece of property.

Norton and Sonja reclined in their comfortable chairs, watching their favourite show on television. It would have been an entirely normal domestic scene were it not for the slurping and suckling and gurgling sounds coming from between Norton's legs. There on the floor was Annie's tiny frame on its knees between her Daddy's legs, with a thick pink latex rubber hood on her head with only one opening for her hard-working mouth, and cotton balls stuffed into her ears so that she couldn't hear anything. It was one of Mommy and Daddy's strictest rules that Annie was not to see nor hear any news, watch any tv, know the date or anything about any current events. They had shrunk her conscious world into simply serving and servicing the two of them as her owners, and nothing else was to matter to Annie at all. She had been taught long ago to keep and worship her Daddy's thick cock deep in her throat, and for the last forty five minutes she had been kept with her mouth-cunt impaled on Norton's prick to the point that her cocksucker lips were planted firmly around the base of his member. Norton had his hands wrapped in the two platinum blonde pigtails that protruded from the sides of the pink latex rubber hood, one of Sissy-Annie's many hoods that completed so many of her gurly and slutty outfits. Norton had been leaking precum into his receptable for nearly an hour and had decided that after about another hour and a half he would feed Annie her second load of seed for the day. Every morning he was awoken with her warm wet mouth enveloping his manhood, sucking him to erection, and worshiping him until he fed her a hot thick breakfast.

Sonja on the other hand, very much enjoyed looking down and seeing a weak little sissy-slut between her husband's knees. A sissy that she had created and developed in part to service him sexually, and in part to be her plaything. Sonja had in fact drifted off to sleep with the mewling slurps coming from floor level in front of Norton's chair until she was awoken by a deep growl and roar as Norton reached his climax and flooded Annie's throat with his load. Five minutes later when the cocksucker had fully drained her Daddy's balls and he had ambled off to the kitchen to make a snack before bed, Sonja called to him that she was going to spend some time downstairs with Annie before coming to bed. Norton grinned, and knew what that meant was in store for the little slut as a means of satisfying her Mommy.

While Norton was most turned on by using his gurl's two slut-holes as vessels for his loads of cum, Sonja's desires ran more towards the opening and stretching of those holes and hearing her little slave-slut scream and cry for her pleasure. A session with Mommy was not complete until Annie was bawling with tear-stained cheeks, and a gaping hole that had been used to satisfy her Mommy's cock. Whenever Sonja used Annie, she would always wear an enormous strap-on cock and make Annie admit that Mommy's cock was bigger than Daddy's, and that she loved it when Mommy raped and abused her hole with her big cock. Sonja loved to stuff her strap-on down Annie's throat until she choked or passed out and loved to force and push until they tore into her cunt making it take the entire column of rubber deep down to the very base. Sonja had told Annie that she would train her little gurl-cunt to be a nice sloppy tunnel with giant big labia-lips on it to please Daddy's cock, and to provide Mommy with a target with which to inflict very erotic torture.

Annie was strapped down to Sonja's fuck bench, completely immobilized with broad rubber straps over her upper back, lower back, thighs, calves, and arms. The slave's cunt-hole was angled upward, and the sixty-five-year old sadist was slamming into her with a ten-inch black veiny dong with a bulbous head on it the size of a small apple. Each time Sonja bottomed out in Annie's pussy she screamed out through the open mouth dental gag that had been seated behind her teeth and ratcheted open to its widest point. In addition to her enormous cock, Sonja wore a bright red latex body suit that struggled to contain her heavy breasts, and pair of black lace-up leather boots. Underneath the sissy's bound body, Annie's caged clitty was drooling thick strings of sissy-honey down towards the floor. There was already a glistening disc of secretions on the concrete floor of Sonja's playroom that had been covered by rubber floor panels, and the harder Mommy raped her gurl, the thicker and faster the sissy-honey began to flow through the cage controlling Annie's clitty.

Sonja had made Annie watch as she flushed one of the two keys to the chastity cage down the toilet with the other one hanging from a slender chain she wore around her neck. Annie was told that if she defied Mommy in any way that the other key might just find its way to being flushed which would mean the cage would never come off - ever. Sonja used this to extract gratitude for allowing Annie one milking per year. Sonja told Annie that cumming was something Dominants were entitled to do, and that orgasms were something sissies were designed to provide. Sis-gurls were entitled to have sissygasms. Sissygasms were releases of juices without ever having a climax. Sonja was quite specific that Annie would never have a pleasurable orgasm ever again. Once per year Sonja planned to milk her slut to orgasm with the chastity removed, allowing climax only at the exact same time that some source of excruciating pain was also applied. She wanted Annie to associate cumming with pain, and never ever experience the sensation of pleasurable sexual release ever again. In its place she wanted a sissy slut who's clitty would drool and leak and respond the more her cunt was used, stretched, stuffed, and raped. Annie had cried when she heard about the decision to never be allowed another orgasm, and the tears that rolled down the slave's face made Sonja aroused. She promptly sat on Annie's face with the sissy installed underneath her worshiping chair, and commanded Annie to thank her and tell her how happy she was to know she would never again have another orgasm while she ate out Mommy's superior cunt. Sonja climaxed five times that day, all over Annie's mouth and face.

Once the dildo-rape was over Sonja stood back out of breath while she gazed upon Annie's stretched and inflamed cunt-lips fresh from the pummeling they had taken from her Mommy- cock. Lube bubbled out of the sissygurl's pucker, and the clitty-cockette continued to leak strings of thick shiny goo. Annie's mouth drooled copiously, making gasping sounds as she tried to catch her breath from having her Mommy's bulk on top of her, and inside of her for such a long and brutal pounding. She was not entirely aware of everything Sonja had been saying to her about trying something new, until she heard the phrase "fisting slut". Sonja had decided that it was time Annie was trained to take as much of her hand and arm up her backside and she decided to try to insert. Sonja had grand designs of seeing how deep and wide she could make her slut-gurl's pussy and wanted to see gigantically swollen and enlarged labia surrounding her rear opening. Annie began to cry as she saw out of the corner of her eye, Sonja lift a pair of thick black rubber elbow length gloves from a table in the corner of the playroom. The gurl's Mommy disappeared behind the fuck bench with a large container of Crisco, and Annie soon felt a handful of the softened shortening being smeared all over her recently opened hole.

Norton relaxed at the breakfast table the following morning, enjoying the sight of his little sissy slut all dolled up for his pleasure. "Well then gurly, why don't you tell me about the fun that you and Mommy had last night after Daddy went to bed".

Annie had already had her breakfast of thick scalding hot cum fresh from Norton's balls with a chaser of his morning piss and was now mincing around the kitchen preparing breakfast for her parents while they planned what would be on tap for that day around the house. Norton commanded Annie to tell him all about the previous night of fun in Mommy's playroom, and not to leave out any juicy details.

Norton tucked into his bacon and eggs while Sonja shoveled her yogurt and cut strawberries into her mouth. Annie had been douched, prepared, and dressed this morning as she was every morning by Sonja, and presented to her Daddy for his approval of the day's outfit. Today Annie was wearing a schoolgurl's outfit. Her platinum blonde ringlet curls were tied up into pigtails with bright pink ribbons, gold hoop earrings adorned her ears, a two-inch thick pink rubber sissy dog collar was buckled around her neck and dangling from the front of it was a heart-shaped tag with SLUT engraved on it. She was wearing a tight white blouse with frilled caplet sleeves and cut-outs around her budding titties, a yellow and black micro-mini kilt skirt, knee high white socks, and a punishing pair of patent black leather maryjane shoes on her feet. Sonja ordered all of Annie's shoes two sizes too small so that her feet would have to be painfully stuffed into them, and with this particular pair had pulled the insoles out and from the underside pushed thumbtacks into them so that when Annie stood or walked in the shoes, not only did they crush her feet, but the points of the tacks would bite and poke into her tender soles. Sonja and Norton had spent a great deal of time and effort manipulating every aspect of Annie's body including her nipples Ð using clamps, suction, and other methods to make them big, thick, rubbery, and permanently engorged. The couple loved the way the giant oversized thick pointy nipples stood out from Annie's otherwise tiny body. Today Sonja had wound rubber elastic bands tightly around the base of the sissy's nips to make them elongated, painful, and inflamed.

"Well then Annie? Don't leave out any details Ð Daddy wants to hear how kind it was of Mommy to spend some of her precious time last night helping you to become a better little whore and slut-cunt for us. I know that you love receiving any attention that Mommy gives you if it helps you become a better little whore."

"Yes Daddy" Annie enthusiastically replied. "Mommy tied me down nice and tight on her fuck- bench in the playroom and let me have one of her nice big black Mommy-cocks in my pussy hole over and over again until she was satisfied. Mommy allowed me to use my sissy-cunt to provide her with pleasure and give her two whole orgasms, so I am a very lucky little sissygurl Daddy! Mommy even let me become her fisting slut last night and she says if I am a good gurl she will use her fist and her arm regularly to make my little sissy-hole a nice big stretched-out slut tunnel for you and her to enjoy Daddy! Mommy used lots of thick white lube and wore big black rubber gloves when she put her hands up my sissy-bum. Mommy said that you both like to see sissy-holes like mine all stretched and opened, and that good little sissygurls just have to learn to take whatever amount of stretching they're given so that the lips around my cunt can get nice and thick and swollen up for your pleasure Daddy. "

Norton grinned at his wife who had finished her yogurt and fruit and was enjoying listening to their slave recount the events of the previous night. They had discussed using Annie for fisting, and among other changes and manipulations wanted to see how deep and wide her pussyhole could be enlarged. Both of them were heavily into seeing young sissies with huge flabby stretched out holes, and although she did not know it yet, the introduction to fisting that Annie had received the previous night was only the beginning of what would be a long journey towards almost incomprehensible levels of dilation that would be inflicted upon her once virgin asshole.

Annie continued with her account of her service to Sonja the night before. "Mommy says that now that I am her fisting slut, whenever she wants she is going to put her fists in my pussy hole to stretch it nice and wide and nice and deep so that I get big thick labia-lips that will make my hole more enjoyable for you Daddy when you let me be your cumdump sissygurl. Mommy spent at least an hour working her fists in and out of me Daddy and even though it really hurt and I was crying and begging Mommy to stop like a good little slutgurl, Mommy knew that what I really meant was that I wanted her to stretch me and hurt me more so that she could have more enjoyment from opening me up. Mommy says that if I am good gurl Daddy, and beg her to keep fisting and stretching me, that she will make sure that my cunthole gets bigger and deeper and wider than I ever thought it ever could Daddy!"

Norton's cock twitched in his pants. "Well Annie Ð it sounds like you are indeed one lucky little slut. Come kneel down here in front of Daddy so that I can give you another big drink of juice before Mommy gives you your poke."

The submissive little sissy dutifully dropped to her knees in front of Norton while he hoisted his heavy cock up into her mouth so she could close her lips around his helmet. After a brief pause, Sonja could hear Annie gulping down Norton's second bladder full piss for the dayÉone of the only drinks that she was allowed to have as a submissive little gurly slut. Norton released a long relaxed sigh as he drained himself into his slave's gullet, thinking that this is how life was meant to be. Why should he EVER have to get up and use a toilet when he had a sissygurl with a wet and eager mouth to deposit his piss, his cum, and his spit into whenever he wanted. Indeed this was the life. While her husband was relieving himself Sonja was measuring out and loading up a syringe full of female hormones that they had been dosing Annie with since the first day of her captivity. It had started with pills, but in order to hasten the results the sissygurl now received a daily injection into either one bum cheek or the other. Immediately after Annie had slurped up the last few dribbles of her Daddy's urine, she popped up and doubled over the kitchen table, pulling up the back of her miniskirt and begging Mommy to make her more of a gurl and give her the special juice to make her titties grow so that she will be a better little slut for Mommy and Daddy's pleasure.

Sonja jabbed the hypodermic into Annie's right buttock, depressed the plunger and flooded her rump with a large dose of estrogen. Pulling the needle free, she slapped the slavegurl on the bum and ordered her to get started with her list of chores for the day so that she would be all done and ready for the visit of her Aunties in the afternoon. She reminded Annie that she would be checking on the quality of her cleaning and housework after she was done, so to make sure that she did a good and proper job if she did not want to be punished for being a bad and naughty little gurl again.

Annie scurried off with each step in her impossibly tight shiny maryjanes cutting into the soles of her feet, with the large base of the butt plug Sonja had stuffed into her that morning just barely visible below the hem of her kilt. What a wonderful time they were havingÉtransforming this little submissive into the perfect little sissy slave.

Next: Chapter 2


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