Training a Sissygurl Annie

By ac.oohay@amrak_tnatiseh

Published on Apr 14, 2020

Authoritarian

PART TWO

Annie was standing quietly in the middle of the room just as Mommy had ordered, looking like the sweet and innocent little teenage gurl that her owners were transforming her into with every passing month. Her platinum blonde ringlet curls were divided down the centre of her scalp with a painfully tight part that Mommy had used a comb and then a harsh hairbrush to create, before tying two large pigtails on the sides of her head with hair elastics adorned with bright pink plastic baubles. Sonja had changed the slut's outfit for the afternoon, and she had shiny gloss on her lips which were now puckered outward by the red rubber ball that had been shoved in her mouth, and fastened to her earlobes were white and yellow plastic stud earrings that were formed in the shape of daisies. The sissy sported a very short yellow sundress with large white polka-dots all over it and a flared miniskirt bottom that was held away from her body by crinolines underneath the main fabric of the dress. A matching scarf was tied extremely tightly around Annie's neck and knotted off to the sideÉtight enough that it bit into her pale white skin and very slightly restricted her breathing. Between the difficulties with the scarf and the rubber ball shoved in her mouth, Annie had started to drool sinewy strings of saliva to the point that Mommy had needed to add a white cotton bib to Annie's attire to keep her dress from getting soiled and wet.

On the slave-gurl's hands, Sonja had stretched into place tight bondage mittens in bubblegum pink latex, which were locked on with straps and buckles as well as two small gold padlocks. They kept her hands clumsy and incapable of gripping things using individual fingers, which increased the challenge for her when she had to serve Mommy or her Aunties any food or hot drinks. Annie's outfit was completed with pink canvass high top runners, laced as tightly to her feet as Sonja could manage, with three-inch platform rubber soles. As with all of her shoes, Annie's feet had been roughly stuffed into runners that were two sizes too small Ð a discomfort that was accentuated by the extremely tight lacing secured with triple knots on each foot. Sonja liked the way Annie's size eight feet looked cramped into size six shoes which seemed more in keeping with her young sissygurl look. Peeking out of the top of each shoe were Annie's frilly ankle socks which like her earrings, were adorned with embroidered white and yellow daisies.

Annie's chastity cage was just barely visible under the frills and crinolines of her minidress. Sonja and her best friends Marge and Sal who Annie referred to as Aunty Marge and Aunty Sal, took great delight in controlling and feminizing the slave, and talking about Annie in the third personÉas if she was not even there. Having complete control of the submissive's clitty was a key element to their control and turning Annie into a willing an agreeable participant eager to do everything that they ordered her to do. More to the point they treated her as though she were an object to be used and trained for their pleasure and to become not only a dedicated and obedient domestic servant, but a skilled sex slave as well. When the three of them would get together in the afternoons for coffee it was an opportunity to evaluate Annie's progress in both roles. With every passing month it seemed like the enforced chastity in conjunction with the hormones were making Andy more and more into Annie. She was becoming more docile, and more and more accepting of her role as a permanent live-in sissy. She was even learning to willingly submit to the abusive and degrading sexual activities that Mommy and her two Aunties liked to engage in using Sonja's basement dungeon playroom.

"She really is starting to come along Sonja. How lucky she is to be receiving all of the training that you and Norton are giving her. Allowing her to serve and pleasure you Ð a very lucky sissy indeed. I hope she shows the both of you the proper appreciation." Sal was craning her neck around to get a good look at Annie from a few different angles as she offered her opinions to the other two women. Sonja did admit that it is a lot of work to train a sissygurl properly, but once it was done the effort would all be worth it as she and Norton would have a permanent slave trained to behave exactly as they required and to be used for anything and everything that they wanted or decided to do to her. Even so, Sonja did respond that Annie was required to get down on her knees every morning and express how lucky she was to be getting turned into a sissygurlÉhow grateful she was to have her sissyclitty completely under Mommy's controlÉand how eager she was to be used and trained for whatever Mommy and Daddy required as they were wise and smart and she was just a stupid little sissygurl.

"Just as it should be" Marge chimed in. "And what about physically? It's obvious that this gurl would have been a pathetic excuse for a male and I know we have her useless clitty permanently locked in its cage, but how are the other changes coming along and what all are you and Norton planning to alter as her training continues?"

Sonja proceeded to explain to Marge and Sal what she and her husband had decided needed to be done in order to make Annie into the perfect slave for their use and as the various aspects of alteration were listed out, all three women beamed at the sight of a tear forming and then running down Annie's left cheek. Even though Annie had accepted that Sonja and Norton had total control of her, there was still a part of her psyche that remained as Andy, even though the sadistic Mommy and Daddy were working diligently at reprogramming that psyche into "Annie", the ultra-submissive fully feminized gurl-slave.

"We're definitely not happy with her weight. She was just far too heavy when we first got her. I think she was 130 pounds and I told Norton that if nothing else our sissy needed to be very small and very weak. I need a gurl I can control and dominate without expending too much energy - one that knows not to defy me if she knows what's good for her! So, we have her on a strict diet and I know we will be able to get her weight down to where it needs to be in order for her to be the perfect sissymaid in our house. I want to see her at about 100 pounds, so she gets a hot breakfast of cum from Norton's balls for breakfast each morning followed by as much piss as he can feed her throughout the day. She's allowed one piece of fruit for lunch so sometimes I will give her a banana or an apple, and on other days it is just one blueberry or a grape. For dinner she gets a plain salad Ð no dressing unless Norton decides to spit on it for her. Once we have her at the weight we want, since she's got such a small frame it will make her sissy-tits, her hips, and her lips much more pronounced and obvious. The hormones we're giving her now with injections are working far better than the pills did and I have her on a strict regimen of wearing corsets and girdles to pinch her in at the waist and improve her figure. Norton wants to see nice big tits but he wants them to be natural so he's willing to wait for the injections to do their job. The doctor we're working with on making her changes told us that the recommended dose is one hormone injection every three weeks, but we decided to dose her weekly and run the risk of any side effects. The results have been very encouraging as the pills we used only developed her tits into tiny buds, but the injectable hormones already have her up to a full A-cup and she's now wearing a training braÉyou'll see it after we take her downstairs. Her muscle mass is shrinking steadily, and she's developing nice thin limbs that I feel I could snap like twigs if she misbehaves."

In truth it was not only the extremely limited calorie intake that Sonja and Norton had enforced on Annie that was responsible for her weight loss, but also the amount of physical work she was required to do in an average day. Every day Sonja would write out a list of chores for Annie that included doing all of the laundry, scrubbing the floors, dusting the entire house, vacuuming, wiping down tubs and showers, grooming her owners by bathing them and doing Mommy's hair, shining Daddy's shoes and boots, and of course, cooking. Annie had been taught by Sonja exactly how Mommy and Daddy like their food prepared as well as the types of meals they like to eat. Sonja still did all of the shopping as Annie was not allowed out of the house but making and serving three meals daily to her owners was something Annie was now accustomed to doing from the duration of her servitude. Mommy supervised every element of Annie's domestic transformation and inspected all of her sissygurl's work. Substandard work was met with a harsh over the knee spanking with Mommy's bare hand, a wooden spoon, or a hairbrush until Annie was blubbering like the little schoolgurl she was now in process of becoming. This was followed of course by the sissy having to repeat the poorly completed chore over again from scratch while Mommy loomed over her and watched every move. Sonja and Norton delighted in relaxing in their recliner chairs as their fem-slave minced around about the house doing their bidding.

"What about her face" Sal asked. "What are you and Norton going to do about that? She must have been such a girly-looking boy before you started changing her Ð another reason she should be thanking her lucky stars that she now belongs to you. I suppose you must be having to deal with facial hair though and you can't possibly have any of that on a true sissy-gurl can you?"

"Absolutely not!" Sonja replied. One of the first things we did was laser hair removal for her entire face. She can't grow any facial hair anymore, and the aesthetician I consulted said that the depilatory cream that I use on her body is quite a harsh and industrial strength one, and that after maybe another few months of application it will have essentially burned away all of her hair follicles so that she won't have any more body hair either."

"And her lips?" Marge inquiredÉ

"Same doctor that's in charge of her hormone treatments" Sonja replied. "He's a friend of Norton's and has always wanted to experiment a bit on a male like Annie used to be, so he's been very keen to offer suggestions as we go along. She's getting her first set of lip injections next week and we're planning on having nice fat rubbery cock-sucking and cunt-eating lips on herÉso big that she won't even be able to fully close her mouth, which will keep her permanently wet and drooling and looking like a hungry little slut. She'll be nothing but a brainless little bimbo schoolgirl with no purpose other than doing anything we order her to do. From what it sounds like the process of doing the needles and enlarging these thin little wisps in to nice fat pleasure-giving flaps is exceptionally painful so I'm planning on having a ring side seat so I can finger and pleasure myself while she's crying and whimpering from getting skewered." Sonja tweaked Annie's wet upper lip as she responded to her two friends about the ongoing transformations.

"And of course" Sal chimed in. "We're both interested to know aboutÉdown below!"

"Annie!" Sonja ordered harshly. "Lift up your dress and show your Aunty Sal and your Aunty Marge your little clitty!"

Annie grabbed hold of the hem of her dress and lifted it up to expose her completely smooth body underneath with her bright shiny stainless-steel chastity cage gleaming against her milky white flesh. She looked at Sonja for permission to speak and after Sonja pulled the wet rubber ball out of her mouth, told her Aunties she is such a lucky sissy-gurl now that Mommy controls the disgusting little sissy-clitty between her legs. She went on to say that It belongs to Mommy and Daddy and should be kept locked up so that it leaks lots of sissy-juice for their pleasure. Sonja then stuffed the rubber sphere back into Annie's waiting mouth with a pop and wiped her wet fingers on the sissy's bib with a look of disgust on her face.

"I told Norton that I and I alone would be in charge of that useless appendage between Annie's legs. She never should have had one in the first place, so between the hormones and the permanent chastity I intend to make it as small and as useless as possible. Once we have it shrunk down to the smallest size possible I'll have a custom chastity device made for her and give her the honour of flushing the keys to it down the toilet so that by her own hand she'll get to see any chance of freedom disappear literally down the drain. It was a hard lesson for Annie to learn, but she understands now that orgasms are for her betters, and sissies don't deserve to receive any sexual pleasure as they are entirely meant only to be giving it to the Dominants they belong to. She knows that in time she'll learn that having her cunt stretched, or fucked, of having a nice thick cock or dildo shoved down her throat is giving pleasure to her owners and therefore should be pleasurable to her."

It had indeed been a difficult lesson and many hours had been spent in Mommy's playroom downstairs with Annie receiving an extremely harsh spanking or an anal rape with one of Sonja's oversized strap-on toys pummeling her hole in order to realize that her entire body now existed to be used exactly as her new owners decided. Sonja particularly liked to help Norton progress Annie's cock-sucking skills by working long flexible dildos in and out of her throat while the sissy choked and gagged and struggled for air. The more slicked the toy would get with thick throat-slime as it was shoved in and out, the deeper Sonja would make her take it and the longer she would leave it in place before letting Annie have some much-needed air to breathe. The smaller and weaker Annie became, the more turned on Sonja was by seeing her pale white sissygurl body bound and restrained in some way while she opened and stretched the sub's wet pink pussyhole to unimaginable proportions. There was something about a tiny white sissy who was genetically male, being fucked by a thick black strap-on cock wielded by an older Domme woman like herself, that drove Sonja sexually in a way she had never thought was possible. Fucking Annie provided Sonja with the most intense orgasms of her life.

"While you're at it gurl, turn around and bend over and pull your bum cheeks apart so your Aunties may see how your sissy pussy is developing." Annie hastened to turn her toes inward toward each other like she had been taught when her Daddy wanted her bent over during the day to receive a quick fuck and fill with his load, and doubled over while reaching back to spread her butt cheeks nice and wide. "Reach further gurl Ð pull harder!" Mommy demanded. "Open those thick labia and really display your pussyhole for your Aunties!" Annie's pink pucker was twitching and quivering, the black silicone ring protruding out if it the only evidence that she was currently stuffed with three anal balls each the size of a small apple. Very early on in her captivity Mommy had taught Annie to expect that her cunt would always be filled with something that one of her two owners would put there. Daddy's cock. Mommy's fist. One of Mommy's cocksÉor a plug, toy, object, or vegetable. Anything that they decided might be fun to try to stuff inside of their slut.

After the inspection was done, all three women were very much ready for another type of fun, and each of them had been getting wetter and wetter in anticipation of using Annie for their pleasure in Sonja's playroom. The sissy was ordered to clear up and clean up the dishes, and then report to the playroom in the basement in exactly 20 minutes.

As Annie entered the playroom, still decked out in her yellow sundress, her Mommy and her two Aunties has been busy getting the space ready for the afternoon's activities. Each of the three wore some amount of latex rubber on their large 60+ year old bodies. They all had very large pendulous breasts and generous midsections that bulged against their rubber outfits. Mommy wore her red bodysuit that kept her tits locked and loaded while both Aunties had opted for garb that exposed their gigantic sagging boobs. Marge's black rubber number had one cutout for each breast to be pushed through that acted somewhat in the same manner that a cockring does for a man's penis, while Sal had donned an outfit also made from black latex that ended just above her tummy with criss-crossed straps forming an "X" that disappeared deep between her massive tits only to re-emerge above her breasts and go over her shoulders. Each woman's outfit was open between their legs so that Annie's mouth could be used to worship their pussies as well as their assholes, and each of them sported a massive strap-on cock which would be used to rape and open Annie's sissycunt to a seemingly impossible degree. Although each of them adored the feel of a warm tongue and mouth probing and caressing their openings, what each of the women had in common was an addiction to the power they felt when they had a genetically male submissive under them, being penetrated, stretched, and raped by what was hanging between their thighs.

Annie was ordered to remove her dress and hang it in the corner, and then kneel on the floor in front of her three women. Naked except for the high tops still oppressively laced onto her feet and the pink bondage mittens, Annie knelt while Sonja wrapped and then buckled a tight black rubber posture collar around her neck. Once fastened, the sissy's head was angled slightly upward and back, and could not be turned from side to side. The collar was rigid and very uncomfortable, neither of which mattered to Sonja, Marge, or Sal, who were entirely focused on their own pleasure which was in fact heightened by the knowledge that Annie was being placed in greater and greater amounts of discomfort and pain.

The sissy was ordered to start worshiping each of the cocks in front of her with her mouthÉlubing them up and begging for her Aunties and her Mommy to rape her and stretch her and open her so that she could be a better and more useful sissy for their enjoyment. After thirty straight minutes of rubber cock-worship Annie was yanked up by Aunty Marge grabbing hold of one of her pigtails, and viciously punched in the stomach. This was followed by Sonja getting a handful of the doubled-over slave's hair, yanking her back up and then slapping her across the face not once, not twice, but six times with one hand then then the other. While this had been going on, Sal had selected a stiff leather paddle from the wall where it had been hanging and gave it a few practice swings in mid-air. While Sal was warming up her arm, Marge bent Annie over while she was struggling to get her breath with her face stinging and burning from Sonja's brutal slaps. Her head and neck were pinned between Marge's thighs making it hard for the sissy to breathe and impossible for her to stand upright. Sonja grabbed both of Annie's hands which were still locked into the pink bondage mittens, and tightly cuffed the gurl's wrists behind her back with a pair of metal handcuffs. Now doubled over with her ass exposed, Sal moved in on Annie and took a full arm swing at her backside with the leather paddle. It whistled through the air and landed on its target with an ear-splitting crack. A fraction of a second passed between the sound of the stiff leather contacting the smooth white backside of the little sissy-bitch, and the scream of agony than emanated from between Marge's fat legs. The vibrations in her flesh caused by the little sub's scream of pain immediately caused Marge's cunt to moisten even further, and what ensued was another dozen identical blows with the paddle while Annie's screams turned to sobs and bawling and begging for relief.

Sonja had not been idle while her two friends continued to work over and soften up her slave, but instead had retrieved both a spreader bar and a long plastic wand with a leather covered handle at one end and a tennis ball mounted on the other. Sal halted her assault on Annie's ass in part to give her arm a slight rest but equally to give Sonja time to fix each of the gurl's sneaker-clad feet to the two ends of the spreader bar which now kept Annie's legs inextricably stretched apart. From then on Sal and Sonja took turns striking the slut, with Sal continuing to abuse Annie's buttocks which were now crimson in colour, and Sonja using the flexibility and whipping action of the long plastic wand to land deeply impactful blows on her sissyslut's sensitive little ovariesÉwhich used to be Andy's balls before he became a gurl.

Between the treatment that was being applied to her ass-cheeks as well as her genitals, Annie had become a blubbering mess which by now had made all three of the dominant women so wet and excited that they were all ready to climax. Marge had in fact already cum once just from the feel of the sissy trapped between her legs and the psychological effect of knowing that the little bitch was in agony. Marge was by far the most sadistic of the three and enjoyed few things more than inflicting true torture on a submissive. The fact that the submissive in question was one that had been forcibly transformed from a male into a feminized and sissified little slave-sissy made it all the more delightful and erotic as far as she was concerned. She had played S&M games with many female subs over her lifetime, but using and punishing a male who had been force-feminized into a simpering little sissy had been a renaissance to her sexual interests. Ever since Sonja had advised her that she and Norton had become the proud new owners of a soon-to-be submissive sissy-gurl, her masturbatory fantasies had all given way to thinking about the many ways that she would be able to torture and abuse and inflict unrelenting agony and suffering on the slave who would have no choice but to endure anything she decided to dish out and what was even more delicious, be grateful for having been used in that manner. A tantalizing thought as the sticky juices from her first orgasm of the afternoon moistened the back of Annie's head that was still held fast between her fleshy legs.

By the time Annie had been reduced to a limp, blubbering, incoherent mess, she was easy for the three large women who even singlehandedly could overpower and manhandle the weak little sissyfag, to spin round and slam down onto her back on one of the fuck-benches in the playroom. Her wrists were uncuffed and then re-fastened together underneath the bench, and her ankles were hoisted up and back in order to be shoved towards her head and neck. Cotton ropes were then used to secure each ankle to the D-rings on the sides of her posture collar, and Annie by then resembled a fetishized version of a trussed-up chicken, folded in half and secured in place with her pussy elevated and exposed ready to be used. While Marge and Sonja began to slather their enormous cocks with thick viscous lube, Sal positioned herself at the head end of the fuck-bench, straddling Annie's head such that her pussylips were brushing against the sissy's well-presented mouth which the posture collar still perfectly controlled. Sonja went first, sporting a large 10-inch black cock with a bulbous head and thick veins running down its side. All in all, a very realistic looking member if its owner had been a big African mandingo. As it was, hanging between the legs of a sixty-five-year-old white woman, it looked every part the weapon of mass destruction it was about to become. Sonja placed the head of her cock right against the puffy pink lips of her slave's sissycunt and paused. She waited several seconds over which Annie had no choice but to anticipate was about to ensue, which caused her little pussy to twitch and quiver in fear. Then all at once, Sonja used her weight and her strength to shove all ten inches of thick, lubed, black silicone rubber deep into Annie's hole in one straight shot. The sissy went from worn out exhaustion to full on screaming in a split second which delivered wave after wave of pleasure through Sal's exposed cunt.

Ordered from above to lick and probe and pleasure, Annie began to work her tongue and her lips on Auntie Sal's labia and her clit. Moaning in ecstasy, the sadistic old woman squatted down further and mashed her mound onto Annie's face making it hard for her to breathe as she was probing and slurping on the wet cunt that she had been commanded to service. Sonja had settled into a rhythm of long-dicking the sissy's cunthole, grinding and working it with every stroke so that the slut felt all 10 inches of thick rubber plowing and splitting her open. Annie's pussylips were beginning to swell and engorge, inflamed from the stretching and forceful entry of Mommy's dick with stroke after stroke. As Sonja would pull her appendage free form her slut's tiny trussed up frame a distinct slurping and sucking sound could he heard which Mommy would keep telling her compatriots was Annie's way of asking for more working of her hole since her mouth was currently busy attending to Aunty Sal's complete and utter pleasure. Sal had already coated Annie's mouth and face with the results of two intense climaxes and screamed in pleasure with a third just as Sonja did the same with a final brutal thrust deep into the sissygurl's tiny body. Both of the hefty women shuddered and swayed in orgasmic pleasure with the slut skewered between them Ð impaled on her Mommy's big black dick, and held fast to the fuckbench with the weight of her big fat Aunty mashing her face flat using her slicked up hairy cunt.

Almost two minutes passed while Sonja and Sal enjoyed the post-orgasmic haze that comes with a mind-blowing orgasm, and simply enjoyed the feeling of Annie held fast between them. In order to keep breathing the sissy had continues to slurp and swallow all of the juices her Aunty was feeding her, licking and cleaning the old woman's snatch as she did so. For her part, Marge hung back and waited to her two friends to disengage from the slut so that she could have her turn at abusing and stretching its hole.

Sonja and Sal settled down on the small loveseat by the wall of the playroom, temporarily exhausted.

Marge unbuckled the shackles that held Annie's wrists and untied the ropes that had been holding her feet beside her neck. Having been bound so tightly in such a strict position for so long, when the bonds were released Annie's limbs hung limply towards the floor. Rest, however, was non-existent as Aunty Marge grabbed hold of the front of Annie's collar and pulled hard to sit her upright before delivering a clubbing blow to the side of the sissy's head knocking her sideways off of the fuckbench. Now sprawled face down on the floor, the naked sissy tried slowly to scramble up on to her hands and knees. Once she did, Marge lashed out with a kick between the legs that impacted directly on Annie's ovaries causing her to howl. Being much larger and stronger than the little slave it was easy for Marge to haul her up while she continued to suffer waves of nauseating pain from her groin, and force her face down over a rubber-covered table in the corner of the playroom. Marge captured both of Annie's hands and forced them up behind her back to keep her pinned to the table. While she was still suffering from the kick between the legs, the pain now coming from both arms that felt like they would snap if her Aunty pushed any harder had Annie's full attention.

"You know slut" Marge whispered in Annie's ear as she bent forward over the sissy's tiny body using all of her weight and bulk to help hold Annie fast in place. "I was going to lube up my cock before I rape you with it, but I think you're still slick enough from when your Mommy used you that we don't need to add any wetness to that ruined little sissycunt of yours!". As Marge finished what she was saying she thrust her hips forward driving her strap-on home into Annie's guts. Marge had selected a phallus that was longer and thicker than what Sonja had used to get the party started. It was bright red in colour and had a simple shape Ð that of a long thick cylinder with no distinct head. It was a foot long, the same girth from one end to the other and was called the "missile". The initial thrust had delivered 8 inches of heavy rubber into the quivering cunthole, but Marge would not be satisfied until all twelve inches of her massive penis were seated deeply inside of Annie's bum.

Marge grunted and shifted and pushed. Annie's feet were clear from the floor and dangled in mid-air as her Aunty had her pinned and impaled on the table. Slowly but surely more and more of the giant cock burrowed its way into the sissygurl's tiny body. After a few minutes Annie was filled with rubber cock to the point that she thought her anal ring would split and she would be irreparably damaged. High in a sexual haze, Marge withdrew a few inches of the missile and then grunted and humped until it had all been fucked back in. Slowly the sissy's hole began to stretch and make it easier and quicker for Marge to empty and then refill, but the pain remained the same as the sadistic Aunt matched the loosening of Annie's pussylips with increasing forcefulness of the fucking. For a full fifteen minutes Annie was brutally sodomized while her Mommy and Aunty Sal looked on. Marge had stopped paying any attention to her target and looked up and around the room with a glazed expression on her face while she twirled and pinched her nipples to the sounds of Annie's whimpering and gasps as air was forced out of her lungs with each and every inward stroke of the missile. As she approached climax her hands drifted away from her boobs and found both of Annie's pigtails. Wrapping her hands in each to get a good grip as she orgasmed, she yanked back with such force that Annie was impaled even more deeply on her Aunty Marge's tool, lifting her upper body clear from the table. Marge shuddered and shook, bouncing the little slut around on her cock as she did so before ripping it free in one fell swoop and backing away from the table. Annie's limp and nearly unconscious body slowly slid off of the table's surface an on to the floor. Sweat dripped from Marge's rubber covered body and pooled around the slave's crumpled form on the floor below her. Annie was barely aware of the voice of Aunty Marge saying to Aunty Sal that it was now her turn and to really rip her open!


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