From student to sissywhore

by bootlicker

20 Jun 2021 8521 readers Score 9.0 (30 votes) PDF Mobi ePub Txt


Philippa had lost track of time while locked in the boot of Dr. Andrew’s car en route to his house for her first weekend of intense physical and psychological training at the hands of the perverted Psychiatrist.  The electric shock collar encircling her neck felt like a noose that was strangling her and filling her with constant fear as she now knew the pain that her abuser could inflict upon her with the press of a button.  If she displeased him in any way…if she were slow to follow an order…if he simply wished to see her writhing on the ground in front of him in agony for his amusement…all he had to do was press the damn button.  She was learning more and more about what it meant to be a thing – an object of pleasure – a slave with no rights and no say over anything that happened to her.  It was this degradation of her will and her realization of the inevitable that would in part allow Dr. Andrew’s techniques to have such a significant impact on her and make her into the submissive and subservient sissygurl that he and Cedric relished abusing and raping and humiliating to their hearts’ delight.

The crunching of the rubber tires on a pea-gravel driveway snapped Philippa’s attention back to the here and now, and her anxiety increased when the engine was cut and the sound of the driver’s side door opening, closing, and footfalls across the stones got louder and louder.  She knew that the Psychiatrist was standing right by the boot of the vehicle…what was he waiting for?...why was he not letting her out?  Wasn’t the whole purpose of her time here with him to spend every waking second being used and controlled as he saw fit?  As if in reply to her unspoken questions, the harshness of the answer crashed in on her consciousness.  With the shock collar once again activated, the sight Dr. Andrews beheld as he popped open the boot of the car was that of Philippa whimpering and clutching at the leather collar in vain trying to pry it from her neck.  Tsk tsk tsk Dr. Andrews clucked – hands off little sissy!  A simple twist of the dial on his hand held remote control jacked up the current coursing from the shock collar into the sissy-slave’s body and Phillipa’s hands flew from her neck and her grip on the collar to her sides as her limbs forcefully extended and her whole body began to spasm and convulse.  Less than five seconds at the maximum setting was all it took to render the teenage slut completely unable to move or resist once the current was cut.  It was a simple task for the large 67 year old to roll his cargo out of the boot, causing her to land on the pebbled drive with a thud.  The attachment of a sturdy leather leash to the back of the dog collar connected sissy and Master, and with an unceremonious “up gurl!” the evil doctor half dragged Philippa along the stones as she began to regain her physical control and did her best to crawl after her captor on her hands and knees.

Clive Andrews’ house in the country was large, quiet, and very secluded.  Long retired he had sought solitude from having neighbours close at hand, which also allowed him to indulge in his favourite extra-curricular activities.  Sometimes he would have a willing submissive whom he had met on line come to his house for a night of fucking and sucking and sadomasochistic play…and sometimes he would use his knowledge of pharmaceuticals and psychology to render a less willing participant compliant, terrified, and physically incapacitated enough that he could thoroughly abuse them without any worry of them fighting back with either their body or their mind.  Control was his aphrodisiac…and the more his partner was under his thrall, the more uninhibited his sexual desires became.  Philippa represented the pinnacle of this dynamic…a true slave that was not to be enjoyed only for the night, but one to be repeatedly raped and psychologically programmed to exist only as he and Cedric instructed her to…she was officially a blank slate that he would mold into the perfect slave.  Compliant, submissive, accommodating…and fully capable of feeling the shame and fear and degradation that so excited the men who would have control of her.

The young sissy could not believe the stamina Dr. Andrews possessed as his thick eight-inch cock was plumbed deep into her throat – dilating it and cutting off her oxygen supply as her rapist grunted and groaned to his third orgasm of the evening since dragging the sissy inside from the boot of the car.  Clive’s meaty fists were clenched tight, Philippa’s pigtails wrapped around them as though they were handles that he had been using to work her skull up and down along his shaft while he used her mouth.  It had been less of a blow job and more of a masturbation session with the older pervert essentially jerking himself off into the sissy’s throat by using the slave’s mouth much in the way that men use those sex toys designed for pleasuring themselves.  Each of the three climaxes had yielded a healthy load of cum for Philippa to swallow, with every drop being expected to slither down the teenager’s throat including the last watery drops that she was to suckle and nurse out of the deflating penis as her doctor came down from his climax.  In between erections, Clive had instructed Philippa to stay exactly where she was…on her knees…staring at his manly cock until it told her everything a stupid little whore like her needed to know.  When it thickened and began to grow, she was to wrap the lips of her oral cunt around it and make it happy until it fed her…when it twitched and quivered, she was to envelope the head and form a tight seal so that she could drink down every drop of hot piss without spilling a drop.  Giving Philippa a third Master – his cock – in addition to the human Masters that she already had, was simply one of the methods at Clive’s command to make it crystal clear to Philippa where she ranked in the overall scheme of things.  More degradation was heaped upon her when she learned that while staying at Master Clive’s house each weekend…all she would eat was cum…and all she would drink was piss.  Good for her the doctor said…Dr’s orders in fact.  The hunger would remind her that she could be starved to death if Cedric or Clive wanted that to happen, and it would also result in her craving the mouthfuls of hot cum that she would receive as rewards for succeeding in ever more humiliating acts of sexual servitude and submission.  Clive on the other hand had enjoyed munching from a platter of nuts and cheese and cured meats that he had pre-prepared before collecting his whore that day, basking in the relaxed pace of his and Philippa’s first night together as Master and slave…Doctor and patient…Abuser, and victim.

Now stripped naked with the exception of her training collar and her chastity device dominating and controlling her tiny clitoris, Philippa lay flat on her back on a double bed, secured there in four-point restraints that Clive had cinched up so tightly that her arms and legs felt as though they were being pulled out of their sockets.  In her mouth was a black rubber athletic mouth guard enveloping both upper and lower sets of teeth, placed there to keep the slut from injuring herself by biting into her tongue.  A broad rubber strap was stretched underneath her jaw and up around her cheeks and over the top of her head like an enormous elastic band…once snapped into place trying so unrelentingly to shrink in on itself that it held the sissy’s mouth firmly shut, pressing her lips together and making them pucker outward as if begging for attention and abuse.  A metal D-ring on the top of the thick restrictive strap was connected by a short bungee cord to an eyelet screwed into the headboard, rendering the slut’s head immobile so that all she could do was stare incessantly at the plain white ceiling. 

With the young slave fully restrained Clive reached between her spread thighs and found the flared base of the silicone rubber plug that Cedric had inserted hours ago before Clive had collected her for the weekend.  Twisting and tugging on it the perverted doctor could feel the sissy’s cunt clinging to it and clutching it…refusing to let it be removed.  Pumping it in and out Clive Andrews stiffened in his jeans as he heard muffled moans coming from Philippa’s punishingly compressed jaws as he sawed the silicone mass back and for the in the slave’s pussy.  Holding it briefly at the widest point to give Philippa a nice painful stretch, one last tug on the toy fully removed it from the sissy’s body all shiny and slicked with both the lubricant her Master had applied as well as her cunt-juices that had been stimulated by its prolonged insertion.

Clive held the toy over Philippa’s face and commented on how hot and soft the silicone had become after spending so many hours embedded in the teen’s hot anus, before lobbing it into a basket beside the bed.  “Don’t worry gurl” the doctor clucked… “we’re going to make sure that hot cunt of yours doesn’t stay empty for very long and have the chance to close right up.  Sluts like you need to have nice stretched out snatches that a real man can enjoy in any way that he wants…wrapped around a nice thick rubber strap on cock…twitching and spasming around his wrist while he enjoys shoving his fist in and out of you…or tightening up on his cock as you work it and massage it with your cunt muscles the way a wanton whore should for her lover.  Each weekend you spend with me gurl we’re going to increase the size of your pussy-plug…bigger and bigger until your owner and I have decided that those lips of yours down there are able to open up and swallow the size of objects that we think you should be able to take inside of you for a real man’s proper pleasure.”  With that pronouncement Clive produced a plug identical to the one he had removed from Philippa’s rear, but clearly on size bigger which was made even more obvious to the restrained sissy as the 67 year-old twisted and shoved it into place, painfully opening her anal sphincter until the point of no return had been reached and the mass of silicone rubber was sucked into the depth of the bound and gagged slave’s rectum.  “You’ll get more training with your new toy tomorrow slut…for now just enjoy that nice full feeling its giving you by opening up those cunt walls and keeping you properly stuffed.”

Dr. Andres however, was not done yet…

Watching the evil physician don tight rubber surgical gloves filled Philippa with terror and if she’ been able to scream and thrash about that is exactly what she would be doing.  As it was, fully immobilized, all she could do was strain to shift her eyes to the left sides of her sockets to try to catch a glimpse out of her peripheral vision in order to provide some clue as to what Dr. Andrews was doing.  Perhaps it was a blessing that the sissy could not see the ten small hypodermic needles that Clive had filled and placed neatly on a square stainless-steel tray on the bedside table.  Each one contained a finely milled plumping agent that would be used to increase the size of Philippa’s lips, making her look more like a fetishized and femmed boy-gurl as well as making her oral cunt more rubbery and thick to form a more pleasurable and firm seal on the hard thick cocks that would be using her mouth for its primary purpose.

Five needles in the upper lip, and five in the lower lip…resulting in watering eyes and pain-induced tremors throughout the teen’s face as the doctor delivered the contents of each hypodermic into the target tissue – expanding it, plumping it up, and filling it to resemble a permanently pouting mouth that would drool and welcome each and every hard penis with which it was presented with an eagerness and hunger that Philippa would learn to display by servicing her Master’s literally hundreds of times.

With the sissygurl’s cosmetic procedure completed, prior to removing his gloves Clive slathered Philippa’s balls with another generous coating of arthritis heat cream with the addition of a layer applied to both of her nipples as well to heighten the slut’s pain and discomfort for the night.  A black-out sleep mask was secured over her eyes, and noise cancelling headphones placed on her head.  For the next eight hours her lips would thicken and swell…her balls and nipples would burn and sweat…and her head would be filled with the sound of Dr. Andrews persuasive voice as she experienced her first of many sessions of near hypnotic subliminal mind control that would form a cornerstone of her training as a compliant subservient she-boy whore to be controlled and manipulated by Clive and Cedric.

Next…a weekend spent training with Dr. Clive….  

by bootlicker

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