From student to sissywhore

“Honestly Clive…if I hadn’t seen it all happen with my very own eyes I don’t know if I would have believed it was possible. You are a fucking genius is what you are!” Cedric raised his beer glass in a mock toast to his friend sitting across the room. The two older men had now been femminising and training Philippa for a full year and spent every minute they could enjoying the fruits of their efforts.

“It’s like I told you Cedric…the most important part is finding the right candidate. My techniques are foolproof when they’re applied to a weak-minded wimp like the slut used to be.” Dr. Clive Andrews sat reclined in a large leather club chair with a satisfied grin spread right across his face. The grin was partially because of the praise he was receiving from his appreciative friend which fed the ego of the retired Psychiatrist – but mostly it was due to what was going on at the moment between his legs.

Sissy Philippa had been on her knees now for nearly an hour, working and pleasuring Dr. Andrews’ eight-inch cock with her mouth…responding to and implementing the training she had been subjected to by the two older perverts who were now her owners and completely controlling her life. In Clive’s left hand was a small remote control that he used to modify Philippa’s behaviour…playing her like an instrument and demonstrating that with practice and time-tested mind control techniques a straight teenage male could be turned into a cock and cum addicted simpering little sissy she-whore for the delight of superior men who enjoyed the company if not the control of pathetic little sluts like her for their amusement.

Stuffed in Philippa’s cunt was a very large vibrating butt plug…one that she wore constantly if her pussy was not otherwise being trained. Clive and Cedric both had remote control devices that were connected to the plug, and they had used these devices to train her to respond to their commands with instantaneous effect. They had trained her to the point that in most cases they did not even need to talk to her…making her into what was truly a powerless full-service sex slave. When either of their cocks were in her mouth, with a press of a button they could speed up and intensify the vibrations coursing through the slave’s sissycunt which was her cue to intensify her suction and the pressure of her swollen mouthpussy lips on their shafts and if not instructed otherwise, bring them to climax so that they could fill her mouth with their seed. If the vibrations slowed and faded, she was to match that change with her mouth and throat as her user was not yet ready or did not yet wish to cum. Early on the two men had decided it interfered with their pleasure to have to verbally command the sissy to suck harder or to slow down, so the solution had been to train her to respond to signals they could simply deliver to her through her pussy which brought about the desired effect without making them go through the effort of having to speak to the little whore.

Personalised blow jobs were not the only way in which the two men made use of their remote controls. Each of them had a pre-programmed setting for the plug so that no matter where she was in the house, doing whatever chore she had been assigned, she would know by whom she was being summoned so that she could go and present herself to that Master on the double. Cedric’s signal was two quick blasts of vibration followed by a brief pause, and Clive’s was one longer burst interrupted by the same brief pause. Upon finding whichever one of her owners had signalled her, she was to curtsy in front of them and as she had been trained, stare at their crotch until told what to do or how to make herself useful. The only time when the plug was removed from her cunt was if Cedric was using it or training it. The men were an effective duo in that Clive much preferred the use of the sissy’s mouth, while Cedric enjoyed nothing more than stretching and opening and stuffing her cunt to incredible proportions. Both men enjoyed the process of modifying Philippa’s body and heaping upon her as much humiliation and degradation as they could muster.

Clive clicked the appropriate button on his remote, and immediately felt Philippa’s lips clamp around his shaft and work it from tip to base like a hoover in long deep strokes that took the rock-hard cock from deep in the slut’s throat to only the bulbous head being cradled gently in the plumped-up pout of the teenager’s permanently thickened lips. With the palm of his hand, while the sissy was bottomed out on his meat Clive held the back of Philippa’s head firmly in place and groaned as he pumped a heavy load of cum directly down her throat into her belly. Keeping her in place, each spasm of her esophagus milked more and more semen out of his balls until she had taken every drop as she had been trained to over the course of literally hundreds of blowjobs. Once fully spent Clive turned off the vibrating plug which was Philippa’s cue to gently release his cock, tuck it away, and stand up…thanking him as she did so for allowing her to pleasure him and swallow his load.

“Up gurl!” the older man ordered… “display that slutty little body of yours and let us have a look at you”

The submissive sissy jumped up from her position on her knees and after offering an obedient curtsy, stood stock still in front of Cedric and Clive with her arms straight and her hands at her sides. She was the perfect picture of a feminised boi-sissy, and if one looked close enough, the remnants of Philip were still visible even though she was now…and forever would be…Philippa. On her feet were a pair of blush pink Keds runners, along with white cotton ankle socks sporting a pink bow made of satin ribbon affixed to each side just above her shoes. Her bare legs of alabaster white skin looked longer than they really were as she was wearing a cheerleader’s outfit made of latex rubber with a skirt so short that her boi-clitty in its chastity cage was visible just below the hem line. Clive and Cedric liked dressing Philippa in rubber, and she had several fetishized outfits made from the stuff in addition to the rest of her sissygurl wardrobe. The skirt was bright pink latex with ruffles that made it flare away from her thighs. The bodice was thicker latex in bright white with wide shoulder straps and just like old-school outfits of the same ilk, had writing across the chest. Instead of a school logo or letterman symbol as would have been usual, Philippa’s outfit had been custom made and in stylised script of pink rubber matching her skirt it read “SLUT” across her chest in big, tall letters. Her arms were bare, and her sissy-tits bulged against the rubber garment from the inside. Although the two men had forced Philippa to start taking female hormones as part of the modification process, to speed the process along she received regular infusions of saline into her chest to both stretch the skin paving the way for bigger tits, as well as to provide a quicker means of humiliation of the slut as well as something for Cedric and Clive to play with. Cedric always reminded Philippa that it was probably her tits and her oversized nipples that really put her family over the edge in terms of permanently disowning her when she had been forced to present herself to them in her sissified form. That had been one of Cedric’s favourite days…seeing his slut bawl in humiliation as she was declared a non-person by everyone in her old life. Using their iron grip of psychological control over the slut they had forced her to admit to everyone in her old life…her family…her old girlfriend from when she was Philip, and her Parish Priest, that she had always wanted to be a sissygurl and to have a much older boyfriend to look after, pleasure, and submit to as a horny little sex slave. She had been forced to bare her new tits, show off her distended and swollen pussy-hole, and even offer to blow her father and her brothers before she was told to never ever come back because if she did, they would kill her. Cedric and Clive had laughed and talked about the day all the way home as they drove from Philippa’s home town back to Cedric’s house with the slut bound and gagged in the back seat bawling her eyes out.

To complete Philippa’s current look, a thick dog collar made of black rubber with D-rings fixed on three sides of it encircled her neck, and her strawberry blonde hair full of ringlet curls was tied up into pigtails at the sides of her head using hair elastics adorned with bright pink plastic baubles. Her mouth was now a freak of nature, having been injected no fewer than five times by Clive to create what he called the “perfect oral cunt”. Philippa could no longer close her mouth in the middle, could no longer speak properly without a wet sissy-gurl lisp, and could not stop herself from drooling constantly as she had been conditioned to have her mouth water at the mere thought never mind the sight of cock, and with permanently open lips the drool had nowhere to go except to pool on her rubber-covered chest between her infused tits. Her tiny little sissy-clit which was now permanently locked in chastity with the key having been ceremoniously flushed down the toilet by Philippa herself while Cedric and Clive watched with delight, was getting even smaller the longer she was on hormones. The likelihood was that by now she was chemically castrated and incapable of getting an erection, but her owners liked the symbolic control it gave them to have their sissy’s genitals locked away for the rest of her life. Her consolation, they told her, was that she would be trained to have sissy-orgasms. Philippa was being trained to have her clit leak and dribble what the two old men called “sissy-juice” practically on command when she was ordered to produce for them…but also to drool out copious amounts of “clitty-honey” whenever she was worshiping cock, or having her cunt used. Again used for humiliation purposes, nothing pleased the two perverts more than putting Philippa on display with a huge wet spot between her legs in the presence of other dominant men.

As Philippa stood on display for Cedric and Clive, a thick string of clitty-snot extended in a shiny viscous string from the tip of her sex down towards the floor. Cedric was the first to pipe up and say “well well Philippa…looks like you really enjoyed your meal from Daddy Clive’s cock now didn’t you…what a lucky gurl. Why don’t you just stand there until your gurl-clitty makes a nice little puddle on the floor between your feet and then maybe we’ll let you lick it up before we go to do your cunt-training exercise tonight.” The mere mention of Clive’s cock increased the amount of stickiness leaking out of the slave’s chastised organ, and a blush of shame came over her face as she looked at Cedric, curtsied, and said “yeth Mathter Cedric…thank you Mathter” through her gigantic swollen cock-gobbling lips.

As they had done for months, the two men chatted and talked with one another completely ignoring the feminised slave standing beside them as she alternated from gazing at one of their crotches, and then the other…all the while adding to the puddle of pre-cum spreading on the shiny wooden floor. For over an hour this went on until Clive finally announced that he needed to be getting off home, and he would bid both Cedric, and Philippa, good night. After giving the slut a possessive, long-lasting deep French kiss as well as a bright red love-bite on her neck, Clive told Philippa how much he was looking forward to continuing the work on her deep throating skills that weekend when she came to stay with him. Cedric said he would see Clive out, and ordered Philippa to get down and lick up her mess before getting her ass up to his bedroom to wait for him.

Having seen off his friend and co-conspirator in the blackmail and feminisation of the submissive teenage boy, Cedric felt his cock begin to harden as he made his way to his bedroom. As ordered, Philippa was standing obediently waiting for him, and curtsied as he approached her. Without a word, Cedric grabbed the thick white rubber shoulder straps of Philippa’s cheerleader outfit, separated them apart, and yanked the rubber bodice down to her waist, exposing her infused tits and engorged nipples. “Much better slut” Cedric cooed as he caressed the sissy’s boobs and began to lightly tweak and finger her distended nips. The caressing and fingering quickly devolved into groping and mauling as well as pinching and twisting as the old man delighted in making the skinny little sissygurl squeal in pain and discomfort as he tortured and manhandled her. Pulling two elastic bands from his pocket he rhetorically asked the young slut if she was going to be a good gurl for Daddy as he wound and wound them around each of her nipples. By the time he was done, they were protruding an inch from her chest, with tips sticking out beyond the elastics that were turning deep purple in colour. “There there Philippa…that will help those little sissy-nipples become the big cow-udders I just know you’re dying to show off through all of the clothes that you wear so that they’re impossible to hide. Now why don’t you get that horny little cunt of yours over to the bed and up on display for Daddy so that he can open it up and stretch it for you just the way that he like hmmmm?” With tears in her eyes and finger-like welts beginning to show on her manipulated breasts, Philippa obediently climbed up on the foot of Cedric’s bed and bent over onto her hands and knees, her rubber skirt lifting up to show of her exposed pussy, and the saline-filled tits dangling downward with her rubber outfit bunched up around her waist.

Having retrieved a leather arm-binder from a drawer, Cedric simply uttered the command word of “arms!” and Philiippa reached back with both hands causing her fce and her breasts to squash against the mattress, her rubber-band wrapped nipples scraping against the fabric of the bedspread. Once in place and cinched in, there was no way for the sissy to lever herself upright from her current predicament. Adding to her immobility, Cedric affixed ropes from each of the two bedposts to the slut’s ankles, pulling them apart as he did so into an awkward and painful version of the splits with the sissy hobbled, doubled over, and splayed open like ripe fruit for the picking.

Chatting casually as he prepared on the other side of the room, Philippa knew what was about to happen…it had happened to her most nights for almost as long as she could remember now. Master Cedric liked to rape her…liked to stretch her with ever-larger thick rubber cocks that he strapped around his waist and used to plow her pussy open like a battering ram. He enjoyed hearing he moan, hearing her whimper, hearing her scream as he impaled her and challenged his own records for both girth and depth as he experimented on her and sought to find the limits of what the human anus could withstand as it was trained to expand and dilate. “I bought you a new lover that you’re going to mate with tonight slut” Cedric announced… “it’s called the Triple Threat on the website I purchased it from and in chatting with the proprietor of the site he says that he’s not aware of anyone ever having succeeded in getting the whole thing fully inserted before…but I just told him that he’s never come across a slut as eager for huge rubber cock as you are my little whore. After I get this whole thing stuffed up that hot wet cunt of yours I’m going to take a picture to send to him…and he assured me that if you can manage it, he’ll give you a store credit to buy two or three more big rubber lovers from him - from what he calls his cunt-wrecking collection….won’t that be fun sissy?” Philippa could only quake with anticipation in response to Cedric’s most effective attempt at striking fear into her submissive little brain. Turning her head to the side, she could now see Cedric standing next to the bed with his newest purchase dangling obscenely between his naked thighs, swinging back and forth as he moved looking like an elephant’s trunk.

The Triple Threat consisted of three identical sections of red silicone rubber, each one shaped like an enormous tear drop. The tip of the giant dildo was the pointed end of the first section, rounded to a blunt tip that would nuzzle its way into the intended target hole with only more diabolical and dilating aspects of the toy to come. Each section was five inches long making for an insertable length of fully fifteen inches. The narrowed end of the second rubber teardrop was a little wider than the first, and the base of the final segment should Cedric actually manage to ram it all the way home, was as wide around as a man’s wrist, which would keep the impaled victim of the enormous sex toy painfully dilated until the wearer decided to remove it. After a brief warm up with a hand-held black rubber cock, Cedric positioned himself behind the restrained sissy and hoisted the tip of his red rubber appendage into place. The spasming pussylips of Philippa’s well-trained cunt looked as though they wanted to swallow the dildo as it was put to them, but as Cedric eased his weight forward and the thickness of the first bulb began to open the gurly-whore up, she began to squirm and shift as much as her restraints would allow. Unable to get away from the relentless assault of Cedric’s oversized phallus, all at once the tortured hole of the slave slipped around the widest portion of the first bulb and pulled it deep into Philippa’s abused rectum. Cedric paused at that point, and began to finger and tweak the sissy’s stretched out and swollen labia…considering them to be his ultimate masterpiece of boi-sissy transformation. By the time he was done with Philippa, he wanted her to have enormously swollen, permanently thickened cunt-lips that eagerly swallowed anything he chose to stuff through them and up into her pussy. She was well on her way, but first things first…she still had two more big silicone bulbs to swallow!

By the time Philippa had distended and stretched to take in the second portion of the Triple Threat, she looked like she was trying to crawl along the bed to escape from the giant mass of rubber impaling that was impaling her…but because of the ropes tied firmly around her ankles, her efforts were completely futile. She was sweating, moaning, and begging Master Cedric to stop as he clucked at her… “tut tut Philippa…you know better than that by now. Your wanton little sissycunt belongs to me and it is my decision and mine alone to decide what amount of stretching it needs to make it into the perfect gaped open trench of a slut-hole that it was meant to be. And my decision is that you are going to make love to the entire length and girth of your new lover tonight no matter how long it takes and no matter how much it hurts…so you may as well stop your whining and concentrate on opening up that ring!”

It took Cedric another twenty minutes of sawing the second rubber bulb in and out of Philippa’s loosening hole to open her to the point that she was now teetering in taking in the widest portion of the third and final segment. Lust filled Cedric’s eyes as he stared at the grossly dilated cunt-lips of his sissy slave, swollen and purple from the extreme tension they were under…marveling at the capacity of skin and human tissue to stretch and distend when properly trained. Philippa now had twelve inches of thick rubber cock stuffed up her ass and she knew that her rapist was not going to stop until she was completely impaled. With one final push the retired teacher drove home the remaining three inches of length and girth, propping open the slut’s hole around the firm silicone of the Triple Threat’s heavy rubber base. Philippa screamed in agony as all fifteen inches were rammed deep inside of her and her whole body jerked and flailed like a fish out of water while Cedric grabbed hold of her waist and held her tight, firmly burying the entire length of his gigantic strap-op inside of her. The vibrations from her attempts to free herself were transmitted back through the body of the dildo and up into his cock, which combined with the sound of his slut moaning in pain and the thought of how gaped open she would remain once her released her made him blast out his load all over the foot of the bed between Philippa’s spread out and quivering milky white thighs. Continuing to hold her tight, Cedric subjected her to a full ten-minute stretch before grabbing hold of his phone and taking still pics of the cock’s base holding open her cunt as well as video footage of him slowly extricating not one, not two, but three huge teardrop shaped silicone bulbs from his personal sissy-whore’s ass. Once fully removed and again dangling between the old man’s thighs, the huge rubber invader was slicked with Philippa’s cunt-juice and the lube Cedric had used to grease up her hole in preparation for the rape. The slut was so spent and so out of it that she barely felt Cedric fingering and playing with her inflamed and distended ass-lips…and could not see the look of pure satisfaction on his face as he marveled at how the hole was gulping for air and involuntarily spasming open and closed in response to the intensity of the punishment it had received.

Reintroducing the vibrating plug into Philippa’s anal hole the toy simply fell out after Cedric had inserted it. “Just as I thought slut” Philippa heard Cedric announce… “it’s time to go up a size in your daily plug as this old one is just too small now to stay put inside of that loosening fuck-hole of yours. What fun it is turning out to be to see how wide and how deep we can make that boi-cunt of yours hmmm Philippa? Now you just stay there while Daddy goes and finds something to seal you up for the night and keep you stretched open…after all, you have another session with your new lover planned for the morning, except I think I can tell you’d like it stuffed insode of you for longer next time to rally ruin that gurly-cunt of yours. Well…I don’t want to disappoint you so we’ll get at it nice and early and see to it your raped and stretched good and proper before you get started on your chores for the day.

With that Cedric left the exhausted sissy immobilised on the bed…tits squashed…nipples strangled…and cunt-hole gaped wide open while he went to his toy chest to find an enormous plug to keep the slut dilated for the night. Briefly he thought about un-tying the submissive slave, but then decided he would only have to restrain her again in the morning so she may as well stay where she was for the night until he was ready to use her again.

Unstrapping the Triple Threat and letting it fall to the floor with a thud, Cedric thought to himself how deserving he was of having a slut like Philippa…and how right it was that she should be made to suffer perpetually for his enjoyment. This was the life alright…and what fun he was going to have exploring and exploiting the teenage whore for the rest of her miserable life…or until he tired of her. He had already been chatting with a group of like-minded Dom’s on the dark web and many seemed interested in purchasing Philippa for use in types of play even he had never even imagined. The lead horse in that particular race was a wealthy Master in China whose fantasies made what Cedric was doing to the teen seem like child’s play. He had discussed it with Clive and together they had loosely planned what their next move would be…perhaps the next slave they trained would benefit from what they learned transforming Philippa. Cedric had even drafted the next advert he was planning to place for a new lodger. Ah well…not quit yet anyway…Philippa still had more pleasure to provide them both with before they would sell her off and begin working on sissy-slut 2.0.

The End….