From student to sissywhore

Having prepared breakfast for her doctor, Philippa stood silently in the corner of the kitchen with her hands by her side while Clive enjoyed the fruits of her labours. She had worn an apron round her waist while doing the cooking and the washing up, but now stood completely naked except for the shock collar and the chastity device on her boy-clit. Dr. Andrews had decided to forego the gag this morning when her released Philippa from her bondage bed to assess how well one of the subliminal messages she had received all night through her headphones was taking root. He had laced the rubber mouthguard the slave had in all night with a micro-dose of the hypnotic drug Cedric had initially used to incapacitate the sissy as a means of heightening the effect of the psychological training. Philippa had been up and about now for close to ninety minutes and had not uttered a word in spite of her first day without a ball or penis gag in quite some time. The voice she’d heard in her head all night had been very clear on this point…sissies do not speak in the presence of a man unless told to do so. It was not the only message she had received however…and Clive smiled in self-satisfaction as he could tell that Philippa’s eyes were fixed directly on his crotch as he sat side-saddle to the breakfast table finishing the last few mouthfuls of his eggs and bacon and slurping up the last of his coffee. Both Cedric and Clive wanted the slave to become addicted to cock – and so training the gurl to not be able to take her eyes off of a man’s crotch whenever she was in the room with one was simply one hypnotic instruction of many that would be deeply implanted into her psyche.

As Clive loosened the belt on his terrycloth robe and widened the position of his feet on the floor he stared lustfully at Philippa and her freshly plumped up lips and swollen irritated nipples – freshly coated again this morning with a generous amount of the heat cream to prep them for more attention later today during which the process of making them thicker and more prominent would begin. With his robe now hanging open Clive paused, and refrained from giving Philippa any direct instruction. Instead he allowed her to get a long uninterrupted view of his flaccid cock hanging between his thighs. It took not even a minute before he saw the slut needing to lick her lips…good…she was salivating…beginning to crave having her mouth filled with mancock and spend whatever amount of time she was told on her knees worshipping and sucking and slurping and swallowing. By the time her training was complete she would be a mindless bimbo unable to control her urges to be used as a slut for the sexual desires of any man she was instructed to pleasure.

“Come and get it gurl” Clive finally advised, and Philippa moved in between the old man’s legs and sunk down to her knees. “Remember what you learned yesterday and do exactly as my cock tells you to slut.”

Staring at the thick penis in front of her and the heavy cum-filled balls nested in the matt of grey pubic hair Philippa could see Dr. Clive’s cock twitch slightly and immediately she wrapped her lips around the cockhead and started to suck gently on it, as if coaxing the flow to start even before the 67 year-old began to release a huge load of hot morning piss into his slave’s mouth. Watching and hearing Philippa gulp down mouthful after mouthful stirred Clive’s sexual desire and nearly as soon as the last drops of piss were being suctioned out he could feel his penis begin to awaken and grow. Philippa could feel it too and increased her suction as she began to slowly work her mouth up and down on the elongating and enlarging organ. With only one treatment, Clive could already feel the difference the plumping treatment had made on the sissygurls lips translating into more noticeable pleasure for him when she was giving him a blowjob. The firmer more rubbery mouth-ring was working his shaft with greater pressure, and heightening his sexual arousal like he had never felt before. He decided then and there to inflate her again that night and to continue to do so until Philippa’s oral pussy was optimally adjusted to provide maximum pleasure. She would look like a freak of nature no doubt with massively enlarged lips that would be unable to close in the middle causing her to drool constantly…but considering the only real purpose for the slut’s mouth now was to be a cock-receptacle the results would speak for themselves.

For fifteen minutes the young sissy slurped and impaled herself orally on the rock hard eight-inch cock while Clive moaned and relaxed choosing to let her do all of the work this time instead of forcing her head up and down like a piston. Only when she brought her hand up towards the shaft to begin stroking the old man’s cock did a quick rebuke stop her in her tracks. Clive warned her that proper sluts only use their whorish little mouths and their hot wet pussies to get their Master’s off…if he had wanted a hand job he would have ordered her to give him one – so she had better get busy making those new cock-slurpers of hers do their job and milk the cum out of his big aching balls.

The entire time Philippa was working the shaft of Clive’s manhood with her mouth - slobbering and drooling all over it - the pervert liked nothing better than a wet and messy servicing…she was conflicted internally by having inexplicable cravings to bring the man to orgasm and get a hot mouthful of cum as well as feeling increasing shame and embarrassment at what she was doing. This was another by-product of Dr. Andrews’ brand of psychological re-programming. Having extensively profiled the teen before the preparation of customized recordings to play for Philippa through her headphones each night, Clive was well aware of all of the influences that had driven the sissy during her lifetime. A morally restrictive family…devotion to the Catholic Church – just two entities that had succeeded more than most at operationalising the use of shame and guilt to determine an individual’s behaviour. Clive was now using those influences to make sure that as Philippa became more and more of a wanton sissywhore, in equal measure her level of shame and humiliation would climb so that she never stopped feeling like a degraded abomination. The conflict in her head remained unresolved as she heard Dr. Andrews bellow in sexual pleasure and pump out five thick pulses of semen filling up her mouth. Philippa gulped it down and continued to nurse on the deflating cock until every last drop of cum had been extracted and swallowed down. Once again soft, and now satisfied, Clive clapped his hands together and said “right slut…now that we’ve both had our breakfast, it’s time to start working on that useless pussy. If we’re going to turn you into the perfect little sissywhore you’re going to need an awful lot of training to make sure that cunt of yours can properly pleasure a real man.

Ordering the young slave to follow him on her hands and knees, Clive led the captive sissy through the house and into his playroom while the obedient whore crawled along submissively behind him. The room was always kept secured when not being used, and even when Clive had one of his visiting subs controlled and restrained inside, he routinely locked the both of them inside and wore the key on a thin chain around his neck. Nestled in his thick mat of white chest hair it was a reminder to the sub that he was in control…that he decided when or if they were to be released…and that he alone could dictate their future and allow them freedom only once he had decided they had been thoroughly and properly used.

By the time Philippa was voluntarily as well as coercively installed within the playroom, she had been positioned on her back in a vintage gynecological exam chair that had been modified to meet Clive’s needs. Held fast against the thinly padded surface of the chair which had been recovered using industrial leather as opposed to the original vinyl, Philippa had a broad restraining belt buckled around her waist from the top of her hip bones to the bottom of her rib cage. Cinched in as tightly as the old man could manage the young sissy was forced to take shorter shallower breaths. She was also secured in place by similar forms of strapping at her neck, thighs, and of course at her calves bound strictly to the stirrups which had been elevated and separated to expose the sissy’s groin, clit, sissyballs, and boihole. The bondage arrangement was completed by wrapping leather restraint cuffs around each of Philippa’s wrists and pushing her hands down towards the floor only to be connected to either end of a wooden broom handle that had been cut to length, fitte with eyelets on either end, and placed under the body of the chair. The teen could rattle and flail and shaker her arms, but could not even raise her hands to the level of her immobilized torso as the hard wooden bar kept banging into the underside of the bondage chair. It was yet another tactic on Clive’s part to allow the slave some voluntary movement, but not enough to be effective whatsoever at disrupting his level of control or interfering at all with what was going to be done to her. Finally, an ironic semblance of familiarity was afforded the pinioned sissy as her mouth was once again stuffed with the rubber mouthguard gag buckled tightly around her head.

The first thing Clive did was apply hard plastic suction cup nipple pumps over each of the slut’s tits. A twisting mechanism on each of the devices forced more of the air out and amplified the level of suction such that more and more of the titmeat was drawn up into the cylinder. This caused the nipples to become engorged while they both remained very sensitive from the arthritis heat-cream they had been rubber with earlier that morning. The lips of Philippa’s sissypussy had been lubed and tweaked while her captor played with them and slowly inserted an inflatable butt plug. With each pump of the hand bulb the rubber invader grew in both length and girth until it had swollen up to a size that prevented it from being expelled no matter how hard the teen might bear down in response to the next phase of her preparation. From the permanently mounted IV pole attachment beside the bondage chair Clive hung a large two-gallon rubber enema bag that had been filled to capacity with cold water. The sadistic doctor wanted to maximize the cramping and discomfort that would result from such a massive retention enema so that he could enjoy himself over and over in the coming days as he replayed the entire scenario which was being recorded via closed circuit video. Connecting the length of tubing from the enema bag to the end of the inflated butt plug, Clive advised his sissy-slut that he needed her to be flushed out and spotlessly clean inside to make sure that the remainder of her cunt-training would be able to proceed without interruption. Opening the valve it was easy to determine when the flow of ice-water began to exit the plug and begin to fill Philippa’s guts as the bound and gagged teen stiffened and reacted to the sensation of the extreme cold. “Two things bitch…” the Psychiatrist announced… “you stay where you are until that little belly of yours is all filled up with every drop of water from this bag…and you’ve managed to heat that water up to normal body temperature.” Being able to see the slowly deflating enema bag in her peripheral vision added to the torture Philippa was feeling as she already felt bloated by the volume she had taken in while at the same time being able to tell that the amount of water that still remained to flow into her was at least double what had already been administered. When one full gallon had moved from the heavy rubber bag into the submissive sissy’s rectum the deep guttural cramps had begun, and by the time Clive was closing the flow valve and disconnecting the tubing from the butt plug Philippa looked nine months pregnant with a hugely distended belly and was writhing in pain to the extent that her restrictive leather bonds would allow. With the submissive teen boi-bitch positioned on the gyne chair and the tiny body’s belly forcibly distended by the volume of fluid that had been pumped into her, at a distance were it not for the leather restraints and the assorted bondage and S&M paraphernalia all around the room a casual observer would have thought a pregnant woman was about to give birth.

For thirty minutes the young slave struggled and suffered while the dominant older man busied himself organising and arranging an array of equipment on a stainless steel trolly on the far side of the room. When the moaning and groaning from the bloated sissy dulled to a soft mewling sound Clive positioned a large plastic tub between Philippa’s legs and with a twist of the metal dial deflated the rubber butt plug. Like a dam being burst, the shriveled latex bladder was forcefully expelled into the awaiting tub followed by torrents of water that burst forth in waves, each one bringing sweet relief to the immobilised sissy strapped to the gyne-chair. It took nearly ten minutes for the pulses and jets of liquid to dwindle to a slow trickle that now leaked out of Philippa’s inflamed hole as her anal ring spasmed and twitched. Allowing only a momentary reprieve for the slave who was now feeling exhausted from the effort of pumping out the entire volume of the punishing enema, Clive flashed an evil grin as he retrieved the rubber butt plug from the tub of water, reinserted and reinflated it, and announced that he hoped she would enjoy round two as much as she had enjoyed round one. Philippa blanched as Dr. Andrews hung a second identical bag of water and once again connected the tubing to the exterior portion of the pumped-up rubber plug. Twisting open the valve, the 67 year-old whistled to himself as he wheeled the plastic tub containing the water from the first enema across the room and removed the stopper in the bottom of it over the drainage hole in the floor of the playroom. By the time the tub had fully emptied and was rolled back into position between the sluts spread out thighs, Philippa was once again distended and sporting a hard bloated belly, this time covered in a slick sheen of sweat from the uncomfortably hot water that had been contained withing the two-gallon rubber bag and was now turning her into a real-life human water ballon. “I think we’ll leave this one in a little longer slut” Clive decided… “ a good solid hour should do the trick to make sure you’re spic and span in there before we continue…now don’t you go anywhere!” Dr. Andrews laughed out loud to himself as he unlocked the door, turned off the lights, and exited leaving the subdued sissybitch in the dark and moaning in agony as she heard the deadbolt slide into place. Philippa was going to suffer every minute that she spent with Dr. Clive Andrews, and he was going to manipulate her body and mind to turn her into a submissive, obedient, and humiliated sex toy to be abused and fucked and degraded in ways that she could only imagine.

In the hallway outside of the playroom, Clive made his way back to his home office with his rock-hard erect cock straining sticking straight out in front of him as he thought about how it would feel to have his huge fist stuffed up the slut’s soon to be stretched out cunt-hole after her enema was done. A string of pre-cum began to stretch down towards the hardwood floor…oh well…an hour wasn’t so long to have to wait, was it?