From student to sissywhore

Philip knocked on the door of the tidy well kept house on the outskirts of Coventry, double-checking the email on his phone to confirm that he had the correct address. The house was a large detached dwelling on a sizeable piece of property surrounded for privacy by a walled garden which afforded the occupants of the home complete isolation from prying eyes. The surroundings were quiet, and perfect for the first year university student to have the peace and privacy to study for all of his courses. He had found the advert for the room for rent on a university website, and had contacted the home owner to arrange a telephone interview which had gone very well with the room for rent being offered to Philip for the upcoming term.

Cedric Watson had warmly welcomed his new lodger, showing him to his large double bedroom on the upper level of the house, complete with his own ensuite bathroom. The only other rooms on that level of the house were a large storage room, and Cedric’s private study which shared a common wall with the student’s ensuite. Philip had unpacked his clothes and belongings quickly, and in short order had made himself feel quite comfortable in his new home away from home for the next few months away from his parents and friends while he attended classes.

Over the next few weeks, the landlord and tenant went about their business independently, exchanging pleasantries each day and learning more about one another via conversations conducted over the breakfast table each morning. For his part, Cedric had expertly disguised his true motives for renting the room to Philip, and had kept the teenager from sussing out the plan for the young lad’s future. Philip was the introverted youngest child of devoutly Catholic parents, growing up in a small village with five siblings...all brothers...and very limited life experience. He was definitely straight, a requirement for Cedric’s plan, and had only had one girlfriend. Being observant members of the church youth group, they had decided to save themselves for marriage and had never progressed past kissing and a little bit of heavy petting when they could steal some private moments together. Philip was eighteen years of age, but his small slender frame, smooth baby face, and pale complexion gave him the countenance of a pubescent youth radiating total innocence. Just what Cedric had been looking for and had been hoping to find.

For his part, Cedric Watson was a retired schoolteacher who relocated to the Coventry area a few years earlier to escape rumours of impropriety that had sprung up around him over the last few years of his career. Rumours that involved teenage students, and behaviour that many found not only improper, but perverted and possibly illegal. With no real proof and the reputations of all involved at stake the best decision was for Cedric to take his retirement early, and start fresh in a new community where innuendo and suspicion would not follow. Never married, Cedric was 62, 5’9” tall, with a very average build, thinning grey hair usually styled in a comb-over across his balding head, and round wire-rimmed eyeglasses. He had inherited large sums of money from both of his parents, as well as two spinster aunts who had left everything that they had owned to their only nephew. Tack on his pension, and he had more than enough money to afford the large house and all of the creature comforts necessary for the lifestyle he had planned for himself. The only thing missing was the type of companion that he required...a problem he was going to solve with the unwilling assistance of his young lodger.

Unaware that his landlord had been watching him since his arrival...strategically asking about friends he had made during his first few weeks at Uni, his classes and Professors, life at home, and how he viewed a multitude of topics and issues of general interest - Philip had unknowingly provided all of the information necessary for Cedric to determine that the young man would make the perfect slave...with fears and insecurities that could easily be manipulated to ensure obedience and total compliance. Cedric was an experienced predator and Philip was easy prey. The reconnaissance and surveillance however, had not all been psychological.

Cedric settled in to his leather desk chair and waited as he gazed at the large full length mirror on the wall of his study. The room was always kept locked to ensure his lodger could not access it...a most important point as it had never dawned on Philip that the big mirror in his ensuite bathroom was in fact a two-way mirror allowing Cedric to view everything that went on while the eighteen year old thought he had total privacy. Predictably, Philip entered the bathroom at exactly 7:30am, and shucked off his pyjamas in order to have a shower. Cedric smiled, and admired the thin petite frame of his soon-to-be slave. Philip was exactly what the old man had been seeking. He was 5’5”, weighed only 110 lbs with thin limbs and a small cock that from the times Cedric had watched the youth masturbate was only about 4 or inches long when erect. When soft, it was no more than a nub which Cedric eagerly anticipated turning into the slut’s tiny little clitoris. The teenager had a pale complexion with light freckling on his face and strawberry blonde hair that had started to grow a little bit longer towards his collar, finishing in a natural wavy curl. Blush pink lips and blue eyes completed Philip’s choirboy type of a look and Cedric’s cock grew hard in his trousers as he watched the naked youth brush his teeth, wash his face, and then step in to the hot steamy shower. By the time Philip was towelling off and getting dressed for class, the peeping landlord had jerked himself off to a satisfying climax, and now sat at his desk continuing to plan his next move with his soon-to-be slave.

Four more weeks passed with little progress except for the deeper levels of detail Cedric gleaned from probing conversation with Philip over the breakfast table. He was sure however, that Philip had caught him staring on more than one occasion in addition to the odd touch on the arm that lingered a little bit too long, and the 62 year old worried that if he did not take decisive action soon his quarry may slip through his fingers.

Lacking any kind of worldly experience, Philip could not articulate why he felt increasingly uncomfortable around his older landlord - but he had decided that at the end of term he would find another place to live. A plan that Cedric became wise to after finding a list of rooms for let during one of his thorough searches of the teen’s room while he was out attending class. The time to act was now.

Spending another Friday evening at home, Philip was taken aback by the knock on his bedroom door. Cedric apologized for disturbing the teen’s private time but wondered if he might be willing to help the older man with the shifting of some large items in the garden shed. Philip was now uncomfortable around Cedric, but had been raised not to be rude so he agreed and followed the 62 year-old out to the shed. An hour later, the shed was clean and organized, and the unlikely pair were sitting back relaxing in the comfortable club chairs of Cedric’s lounge. Parched from the work they had done, Philip eagerly gulped down the extra-tart lemonade Cedric had offered him...the intensity of the lemon completely masking the chemical taste of the tranquilizer that laced the ice-cold beverage.

The last thing Philip remembered was the room around him starting to go fuzzy and spin, and Cedric’s voice sounding muffled and distant like it was coming from a mile away. He felt sure that he could feel someone else’s hands all over his body, and being assisted to stumble back to his bedroom in a total stupor. Never having even consumed so much as alcohol before, Philip’s system was hit hard by the drug and although technically conscious, he was powerless to prevent Cedric from controlling his body.

Over the next several hours Cedric enacted the first phase of his plan. Forcing the teen to swallow another dose of the tranquilizer drug a few hours after the first, and after that a third dose which ensured the older man would have full control of the teenager’s body and mind for more than enough time to accomplish what he had set out to do. The after effects of the drug would leave Philip with vague and disjointed memories of his time under its influence, and while in the midst of its thrall he was powerless to prevent Cedric from doing whatever he wanted as the chemical compound reduced inhibitions to near zero while leaving the victim the appearance of being conscious and merely intoxicated.

Philip awoke the following day with warm sunlight streaming through the bedroom window and warming his bare skin. He lay sprawled across his bed wearing only pink satin panties, and feeling like he had been hit by a truck. His mouth was dry and his throat felt raw and sore whenever he swallowed. His muscles ached and when he hauled himself up in front of the mirror he could see small round bruises on his chest around his nipples which were puffy, chafed, and irritated. His cheeks were flushed red and his lips swollen - accented by bright red lipstick which was smeared around his mouth giving him the appearance of a perverted clown. As the fog in his head continued to clear, he also became very much aware of a burning pain coming from his anus...something he had never before felt and made him walk with a bit of a waddle to avoid aggravating the ever more noticeable sensation. A hot steamy shower did make him feel better, but confusion returned when he went to get dressed and found all of his drawers empty, and his entire closet devoid of a single garment of any kind.

Towel wrapped around his waist, Philip stormed in to the kitchen and marched straight up to Cedric who had just finished washing up his breakfast dishes. As the eighteen year old began to demand to know what had happened to his clothes and why he had awoken dressed in pink panties with no ability to recollect what had gone on the night before, he was met mid-sentence by a vicious slap across the face that caught the student lodger totally off guard. Feeling his stinging cheek with the palm of his hand, Philip recoiled from the older man and plopped down into one of the kitchen chairs. Cedric advanced quickly on the youth and delivered another slap to the other side of Philip’s face, and with a look of pure rage in his face and intense anger in his voice demanded that Philip remain silent and not utter another word.

Stunned mostly by the physical assault he had just endured but also by the tone and demeanour of his landlord, Philip sat silently as he looked up that the older man who now stood directly in front of him looking down at the teen with intensity and malice written all over his face. Confusion and disbelief quickly were replaced by fear as the slender young man gulped and sat back in his chair.

“Better”, Cedric pronounced, his face softening a bit and the tension in his body relaxing slightly which made Philip instantly feel more at ease. “I am sorry to have had to strike you Philip but I will not tolerate hysteria in my house, certainly not from my slave”.

The teenager’s mind was reeling...did he just say “slave”?...what the hell was going on?! Going a million miles an hour Philip was trying desperately to comprehend what was happening while at the same time struggling to reconstruct the blank spots in his memory from the night before. He remembered helping Cedric in the shed, sharing some lemonade together after that...and then nothing. Vague images of Cedric’s face, and feelings of his body being manhandled...but nothing definite...nothing certain...

The eighteen year old was yanked out of his distraction by the voice of his 62 year old landlord as the older man took a seat at the kitchen table across from the young man.

“I would suggest that you sit silently and listen while I explain a few things to you Philip. Believe me, it’s in your best interest to listen, and to do exactly as I say from this point forward. If you do not, I will see to it that you regret your disobedience for the rest of your life. I am going to show you a series of photographs and some video footage last night, and after you have finished looking at them and watching them I will explain to you how things will be from now on. Most importantly - you will remain absolutely silent until I tell you to speak...is that understood?”

Stunned, Philip simply nodded while Cedric produced a tablet, switched it on, and slid it across the table. Opening the specific file as directed by the older man, Philip was horrified by what he saw. Photo after photo of him in various states of undress in a series of extremely compromising sexual situations. There were pictures of him masturbating his cock, masturbating someone ELSE’s cock which must have been Cedric’s, licking and sucking and orally servicing that cock, and several that showed his mouth and face coated in semen while he attempted to lick it up and swallow it with his tongue. Worst of all there were pictures of his winking pink bum hole, and of him pulling his bum cheeks apart for the camera while sliding his finger into his anus. An entire series of a cock opening and stretching and fucking him taken from the perspective of the rapist was also part of the horrifying file. Only the teen’s face was clearly shown in every photo, and Philip looked like a fully willing participant with lust and desire painted onto his face - which caused the teen to descend further into stunned silence. Directed at that point to open the video file, Philip was treated to a 30 minute video of himself donning women’s underwear, applying lipstick to his lips, tweaking and pinching his nipples, and then slobbering all over an erect penis as he kissed and licked and sucked it until it filled his mouth with a hot load of cum which he swallowed and then proved to the camera he had enjoyed by displaying his empty mouth and giggling like a giddy schoolgirl.

With the video finally finished, Philip slumped back in his chair, looked at Cedric, and after a very long silence pleaded with his eyes to be given some explanation of what was going on and what he had just witnessed.

“I can see that you are ready to be reasonable young man, and if you promise to be good I will explain to you what you have just seen...and what it all means. Would you like that Philip? Are you ready to behave and listen quietly while I tell you a few things?” The youth nodded, swallowed hard, and listened in horror as the whole sordid situation was laid bare for him to try to comprehend.

“Last night Philip, the lemonade I served you was laced with a particularly powerful hypnotic drug which I administered to you no less than three times during the course of the night. This is why you do not remember any of what went on, as the drug has a side effect of inducing near total amnesia once it has worn off. It does however, leave the user with the appearance of being completely conscious, and the reality of being willingly compliant to do whatever they are told. You will note that the only person recognizable in the photos and the video is you although I am sure you have worked out by now that the other man is in fact myself. It was necessary to ensure that only you could be identified, as the evidence you have just reviewed will be sent to your family, your parish priest, your friends and professors at Uni, and of course your girlfriend back home if you do not do whatever I say from this point forward. How do you think they will all react if they see proof positive that their son...their friend…their parishioner...the love of their life...is a cross-dressing cock slut eager to suck and swallow and get fucked by another man? The deeply religious people around you Philip...what do you think they would do? I’ll tell you - you would be ostracized...cast out...disowned and disinherited. Your girlfriend would dump you in an instant and very quickly everyone in your entire world would know that you are a perverted little faggot. Would you like that Philip?”

His mouth hanging open and tears welling up in his eyes, Philip slowly shook his head from side to side as a clear indication that he most certainly did NOT want any of that to happen. Why was Cedric doing this? Why would he threaten to ruin Philip’s entire life?...

Almost as if the old man were reading his mind, he continued his explanation by saying “you are no doubt wondering why I have done this to you Philip. Well, the most basic reason is because I can - but more to the point, I have always had a desire and a lust for young slender boys like yourself. No idea where it came from really, but it is intense, undeniable, and it very nearly cost me my career and possibly my freedom. So, I needed to find a way to satisfy my needs while at the same time making sure that there would be no way for me to end up in the crosshairs of the legal system while doing so. You, my dear lad, represent the perfect solution. You are young and gorgeous, but legally you are your own person and capable of making your own choices. What I have done is made it obvious that your choices include behaving like a promiscuous homosexual slut who couldn’t wait to get away from his suffocating family so that he could act out on his perverted impulses...taking the first chance he got by going away to school so that he could become a cock-worshiping boywhore - and as such I now control everything you do, and everything you say - because if you do not obey me in every single way, everything that you saw just now will become public knowledge. What I decided Philip was that I needed a submissive obedient little sex toy to service and pleasure me and to do whatever I say whenever I say it...and you dear Philip...are that slave. From now on you will behave exactly as you are told, for you are no longer your own person dear boy...from now on, you belong to me.”

Philip was openly weeping now as he realized that his life was ruined. He could not imagine his mother seeing the photos and the video of himself slobbering all over an erect penis...and his father and at least two of his brothers would most likely kill him if they were ever to find out. And his girlfriend...what would she say if she ever saw the disgusting evidence. She would never speak nor look at him again. He would be the laughing stock of his small group of Uni friends, and the intensity of the shame he was already feeling without any of these people having seen the digital images was enough to to nearly make him throw up. If they were to find out, he would lose his mind.

Seeing the resignation to the situation wash across the young man’s face, Cedric smiled a smug and sadistic smile, and gave his new found slave his very first of a lifetime of orders. “If you understand the situation as I have explained it Philip, and wish to avoid having everyone in your life learn once and for all what you truly are, I suggest that you demonstrate that understanding by getting down on your knees, crawling over here to me, and taking out my cock so that you can suck and pleasure and worship it. If you do a good job, I will reward you again with a nice big mouthful of my cum for you to swallow and appreciate. Do it now, slave.”

Almost in a trance the eighteen year old did exactly as the old man bade him, and soon found himself on his knees on the kitchen floor, with Cedric’s pants open and his hard six inch cock mere inches from his mouth. From above, Philip heard further instructions advising him to make sure he moaned and cooed with pleasure through the deep shame he was experiencing, and that he slurp and slobber all over the cock while he begged to be fed a hot load of semen. Having been successfully profiled by the retired teacher and experienced predator of young men, Philip slipped quickly into subservience and resignation to his current situation. The old man enjoyed wave after wave of pleasure as his new slave bobbed up and down on his hard cock and begged to be fed and to be allowed to swallow his hot load. Once the 62 year old had pumped the contents of his balls into Philip’s mouth, he told the cocksucker to look up at him and open up to display the thick creamy load on his slutty cum-hungry tongue. As he did as he was ordered, Philip realized that once again Cedric had recorded the entire blowjob on the tablet, adding to the existing evidence of Philip being a cock-obsessed wanton faggot. A tear formed at the side of the teenager’s left eye and ran down his cheek as he heard one word uttered by his new Master... “swallow”.

Over the next couple of weeks, life changed dramatically for Philip as he became more and more dominated by Cedric, every day transforming into less of an individual, and more of a slave. The retired teacher was an expert at brainwashing young men, and now had Philip squarely on the path towards total submission to his every whim. How the young man dressed, what he ate, when he came and went from the house to attend his classes. The experienced predator supervised while he had Philip create an entire journal, dated merely a week after he had arrived at Cedric’s house, detailing how he was looking forward to living out his fantasies of becoming a feminized sissy whore for an older dominant man now that he was away from his suffocating environment in his home town. The journal detailed how he begged and cajoled Cedric for weeks on end to take on the role of the dominant older Master, and how with great reluctance, the 62 year-old had finally agreed. Under threat of exposure and humiliation the old man had the submissive youth write the most horrible and ungrateful things about his family...how his girlfriend was a naive frigid bitch, and how the Catholic Church was nothing but a cult preying on those too stupid to see it for what it really was. The entries went on to detail kink-driven sexual fantasies Philip had for the retired teacher he was renting a room from...all containing the most explicit and degrading details which the youth professed to be turned on by to the point of craving the total domination by an older man in order for him to feel whole. Once the journal was completed, it was locked away with all of the other blackmail material...ensuring Philip’s ongoing obedience and willingness to submit.

- - - - - - - - - - - - - - - - - - - - - - - - - - -

Relaxed and content, the 62 year old took casual notice as his slut entered the room and knelt silently between his legs as he had been instructed to do. “Laundry done slave?” The Master inquired. Philip nodded his head. “And what about the cleaning in the kitchen and the bathrooms - floors and windows washed? Trash taken out? All of my shoes and boots polished?” Again Philip nodded. Cedric had kept Philip busy all weekend with a myriad of household chores as the slave was now responsible for any and all domestic duties around the house.

Philip was dressed only in a pair of silky girl’s panties, and sported suction cups on both of his nipples as well as a thick pink rubber collar buckled and padlocked around his neck. In his mouth, a bright pink rubber ball gag had kept him both silent and drooling like crazy for the duration of his duties, with the Master now being ready to make full use of the stretched and wet mouth of the youthful slave. After having received yet another relaxing blowjob while he reclined in his favourite chair - once again recorded for both posterity and of course blackmail - Cedric thought to himself how wonderful it was to have a cocksucker personalized and trained to suck him and take his loads in exactly the manner he most desired. A total sex slave who existed to take whatever he dished out and to be used however he saw fit. The training process would indeed be most enjoyable, and in the end he would have willing holes trained specifically to his sexual preferences, and a mouth perfectly versed in how to tease and pleasure his asshole...lick his feet...his armpits...or any other part of his body he desired.

“I’ve made some decisions Philip” Cedric announced after coming down off of his climax and then tightly replacing the slave’s ball gag - Philip was kept gagged in some way 24/7 while in the house unless his mouth was being used by Cedric, or if he were eating or sleeping. It was all part of the training process to help Philip understand his place. The gags were always very tightly buckled and either forced his mouth painfully wide, or constantly tickled his gag reflex if it were a penis gag stuffed to the back of his throat.

“Now that I have the slave that I so richly deserve as a superior Dominant Man compared to you as a snivelling little faggot, I see no reason why I should ever have to endure a single minute without the ability to make proper use of you. So, I’ve decided that you will drop out of university”.

A look of shock washed over Philip’s face. “I know I told you that I would allow you to continue with your classes, but I have so enjoyed having you about the place during the days and the way in which your mouth and pussycunt are learning to properly pleasure their Master’s cock, that I see no need for you to continue with your academic studies. Everything you need to learn now that you are nothing but a slave, I will teach you...which means that those university classes are just a waste of time and money. I will think of a manner for you to properly thank me for making this decision for you slut. I know that you appreciate your Master looking after you so thoughtfully. Right? A serious glare in Philip’s direction provoked the slave to nod repeatedly in agreement, even though he wanted to burst into tears at yet another ruination of his independence...his life. “You will send an email this afternoon withdrawing from your classes permanently is that understood?” His lips stretched around the large rubber ball and drool escaping from both corners of his mouth, the youth nodded obediently with resignation.

That however, was not the only decision that Cedric had made.

“Follow me slave, I have something to show you. It’s time we started in earnest to craft the new image befitting your position as a permanent slut. While I have enjoyed keeping you naked and in panties in the house I have now permanently disposed of all of your old clothes and replaced them with a wardrobe of my choosing. I am also giving you your old bedroom back...with a few changes of course.”

The pair entered the bedroom the teenager used to rent from the older man which now had a large deadbolt as well as a padlock installed from the outside, and Philip’s mouth would have hung open if it were not stuffed and buckled tight by a large rubber ball gag.

The formerly white walls were now a blush pink, and the wooden framed twin bed had been replaced with a white metal framed double complete with pink and white bedclothes capped by frilly pillowcases. The panes in the large window had been replaced with semi-opaque frosted glass preventing anyone from seeing inside, or those inside from seeing out. The garden wall rose above the level of any of the main floor windows but Cedric could not risk Philip trying to signal anyone for help from his bedroom window. The sill had also been nailed shut, and white wrought iron bars had been installed making the room resemble a frilly feminine prison cell. The floor was gleaming polished hard wood, and across from the foot of the bed sat a make-up table with a large mirror and a low stool to sit on. In the corner, stood a plain wooden contraption that looked like a bench of some kind, with leather buckles and straps hanging from it in various places.

Stunned, Philip wandered around the room hardly able to believe how it had been changed in the last few weeks. Since his enslavement he had been sleeping on the floor at the foot of Cedric’s bed, chained there by a tether connecting his collar to the heavy footing of the sadist’s king-sized bed.

Dotted around the walls of the bedroom were framed stills from the blackmail videos and copies of some of the pictures Cedric had taken of Philip worshiping cock, swallowing cum, of being assfucked like a little whore.

“Open the closet slut” Cedric commanded. Philip complied and was stupefied once again by what he saw.

Hanging neatly in the closet, were half a dozen different outfits. Two were complete schoolgirl sets in matching colours of pinks and blues and yellows and creams. Next to those was a cheerleader’s outfit clearly constructed out of latex complete with a built-in corset and snap-open patches over the wearer’s nipples and thick rubber shoulder straps. The skirt was ruffled making it flare outward and was bright cotton candy pink while the bodice was constructed of thicker white rubber. On the chest the word “SLUT” was emblazoned in stylized script.

The other outfits appeared to be a shorty pair of dungarees in powder light blue crinkly nylon with frilly elastic hems to the legs, a long red shiny skirt made of gleaming latex along with a matching red rubber crop-top, and a yellow sundress with large white polka dots sporting a sailor-suit neckline trimmed with white lace.

On the floor was an assortment of footwear - everything from shiny patent leather maryjanes to girly pink running shoes of various types and designs. Strappy sandals and buckling shoes all with little locking mechanisms were neatly arranged on two racks. Hanging on the inside of the closet door were more of the gags Philip had become accustomed to wearing as well as rubber and leather hoods in black and pink. Built in shelving in the closet displayed an array of butt plugs, dildos, and bondage straps arranged neatly as if the entire thing was a showcase for a perverted sex-shop.

So thoroughly mesmerized by the sight of the contents of the closet as well as the surroundings of the bedroom, Philip did not even hear the buzzing of Cedric’s mobile phone or the short conversation his Master had before disconnecting and stuffing the phone back into his pocket.

“Wait right here slave...I’ll be right back - a special guest has just arrived and I think it’s about time the two of you met.” With that the Master exited the room, and Philip heard the deadbolt and the padlock being secured to lock him in his horrifying new room.

Minutes later, Cedric re-entered the room followed by another man who appeared to be a few years his senior. “Slave, please say hello to Dr. Clive Andrews.”

Embarrassed to be so overtly sexually displayed before a stranger and in the surroundings of the feminine bedroom adorned with porn pictures and sex toys, Philip instinctively used his hands and the twisting of his body to try to hide himself as much as possible from the direct and penetrating stare of the stranger in his midst.

“You’ll have to excuse Philip, Clive” Cedric said... “I’m afraid that we have not had any visitors to the house since our relationship was made clear to him.”

“Quite alright Cedric”, Dr. Andrews replied... “it will take her a while to adjust but I am sure that we will get there in the end and she’ll be the picture of obedience and submission.”

She? She?! What the hell was going on???

The guest in the room, Dr. Clive Andrews, was someone Cedric had met soon after moving to Coventry. The internet was indeed a wonderful tool for finding no end of kindred spirits no matter what one’s interests. A retired Psychiatrist, he and Cedric had quickly begun to share stories and fantasies and in time, the retired teacher brought the physician into his confidence about what he wanted to do with Philip. More than happy to help, Clive had been instrumental in that he provided the prescription for the hypnotic drug that Cedric had used to incapacitate Philip and film all of the blackmail material necessary to keep the eighteen year old under tight control. The ultimate plan however, would make far more use of Clive’s professional training beyond simply writing a prescription.

“Now Philip!” Cedric admonished... “stop all of this fidgeting and sit down. Clive has come over today because he has agreed to assist me with your training and has very generously offered to be your doctor. You should consider yourself to be very lucky indeed that an important and busy man like Dr. Andrews here would be willing to assist a silly little faggot like you.”

Once again Philip’s natural tendency capitulate and surrender took over, and he sat back onto the metal framed bed, the backs of his bare thighs causing the frilly feminine bed clothes to crinkle and rustle. The two men began to speak with one another as if the teenager were not even in the room. Their words for a time drifted away and Philip studied Dr. Andrews who gave off an air of confidence, dominance, and control. He was a couple of inches taller than Master Cedric, heavier set, with a thick white beard and moustache. He was five years Cedric’s senior at 67 years old, but radiated vitality and strength. He had very large hands and feet even for a man his height, with a thick midriff and large buttocks and thighs.

The teen was brought back to the here and now by the feel of Dr. Andrews hand gripping his chin and pulling him back up to a standing position. Feeling more like a piece of merchandise than a human being, Clive Andrews swivelled Philip’s head from side to side, tweaked and pinched his nipples provoking a high pitched squeal, and then yanking down the panties which were the only modesty the slave had left. With the undergarment now bunched up around his knees, Philip heard Dr. Andrews order him to step out of them altogether leaving the teen wearing nothing but a ball gag and a rubber collar.

“Just as I assumed Cedric”, Clive asserted as he nodded his head and casually fondled Philip’s now exposed cock and balls. “Tiny little thing down here between her legs...as you said much more of a clitoris than a cock...all the more reason that she needs to be trained as a proper little sissygurl. Mark my words, you’ll get years of enjoyment out of her once we’re done with the training.”

Clive Andrews retrieved his old-style medical bag, and sat himself down on the low stool by the dresser and make up table, beckoning Philip to approach him as he did so.

“Come over here gurl” the doctor called out as he rooted around in his bag. Cedric shot Philip a terrifying glare, silently advising him to comply if he knew what was good for him.

Holding the slave’s attention like the Pied Piper, Dr. Andrews began to speak as he manipulated and manhandled the teens shrivelled sex. “You see Philip, little sissy faggots like you exist to serve real men like your Master Cedric and myself. Problem is, that your kind are just too silly and stupid to realize it on your own and what you really need is guidance. Training. You need superior men like us to spend some of our precious time ensuring that you learn your proper place, and helping you to become the mincing little gurly-slaves that you were meant to be. Luckily for you, we are going to make sure you get all the attention you need. When we’re done with you, you won’t even recognize yourself. You’re going to be the most obedient, the most eager to please, the most horny little sissy bitch you can possibly imagine.”

A quiet click and an uncomfortable pressure between his legs finally disrupted Dr. Andrews grip on Philip’s attention, and when he looked down at his naked body, he saw a pink contraption encasing his cock.

“What you’re looking at there gurl is called a Holy Trainer. It’s a chastity device that you’re going to be wearing from now on. Part of your training to make sure you realize that you’re just a femmy little gurly fag is to make sure that the only cocks you’re focused on are mine, and your Master Cedric’s. Men’s cocks. Not a useless little clit like you have between your thighs. In fact, you make sure that you never refer to what you’ve got down there as a cock ever again you hear? You have a clit down there gurl, and I hope you enjoyed your last erection because it truly was your last. No more hard-ons for you my dear...from now on you will be servicing hard cocks, which means there is no need for you to have one. Ever. You’re done. As of right now, you start focusing on your holes just like any slut - because that’s all that you are - a couple of holes to be trained to take cocks and cum and piss and anything else your betters decide to stuff them with. Now be a good gurl and nod if you understand what I’m telling you slut.”

Struggling to process what he was hearing as well as adjusting to the physical sensation of having his cock secured in a chastity device, Philip not only failed to follow Dr. Andrew’s direction but began to completely ignore both of the older men altogether.

“Looks like a more practical lesson is required here Cedric” Clive said, before twisting Philip’s left arm painfully behind his body and forcing the slender young teen to double over at the waist. The 67 year old Psychiatrist was surprisingly strong, and quickly had Philip’s right arm under his control as well, pinning both hands behind the jack-knifed teen’s lower back and holding them there as the young slave began to mount a most futile struggle.

Cedric’s right hand began to unbuckle the ball gag and Clive used one large hand to maintain his control of Philip’s arms while both men used their free hand to undo their pants and free their hard cocks. Philip was very familiar with the feel of his Master’s cock opening up his mouth and working its way towards the back of his throat, but while Cedric was gripping handfuls of the teen’s strawberry blonde hair and settling into a regular rhythm of raping the boy’s mouth, the young slave felt Dr. Andrews smear a thick wad of spit around and then into his asshole. The old doctor’s fingers were then replaced by something much hotter, much bigger, and much more blunt than his fingertips.

The retired teacher’s 6 inch cock was buried to the hilt in the eighteen year old’s mouth, completely gagging him and forcing him to gurgle and choke all to the 62 year old’s delight. From behind, Dr. Clive Andrew’s eight inch truncheon of a penis was trying to batter its way into Philip’s pussyhole. The 67 year old doctor’s cock was uncut with a blunt bullet shaped head that was the same thickness as his shaft, giving the erect cock the look of a column of flesh capable of significantly stretching out its victim’s hole. Slow, steady, unrelenting pressure was finally rewarded with the head of the old man’s cock breaking through the teen’s anal ring, accompanied by a stifled scream of agony muted by Cedric’s hard cock. Tears began to flow freely down Philip’s face and he tried without success to extricate himself from the two cocks that now had him impaled like a stuck pig on a spit. His Master pumped and worked his mouth and throat while the visiting doctor humped and raped his asshole, pushing home more of his thick eight incher with each and every stroke. For fifteen minutes the two old men grunted and moaned with pleasure while the young slender slave sandwiched between them squealed and jerked in agony with each thrust of the cock.

As if in stereo, the 62 year old former teacher and the 67 year old former physician howled with the pleasure of climax as they simultaneously pumped their loads of cum into each of Philip’s abused holes. Three, four, five shots of hot ropey cum impregnated the tiny teen before each man pulled free and allowed their prey to slump down in a heap on the floor at their feet.

Regaining his breath as he came down from climax, Dr. Clive Andrews leered at the freshly raped teenager on the floor with cum running freely out of his pussy, and with a self satisfied smugness said to his friend “Cedric...I think now would be a good time to tell the slut that she’s getting a new name to go along with her new life don’t you?”

The abused young man’s Master nodded in agreement and grabbed one of the hangers out of the closet and threw it along with a pair of shoes onto the floor beside his slave... “get dressed, and get your ass downstairs to join us in no more than fifteen minutes...Philippa”.

With that pronouncement, the two men stuffed themselves back into their pants and exited the room, retiring to the living room to enjoy a drink while they waited for the slave to join them as ordered.

Her ass on fire from having been stretched and inseminated by the old doctor, and her face flushed with the exertion of having once again sucked off her Master Cedric as well as the deep shame she was feeling as a shy Catholic student now being trained as the homosexual sex-toy of two abusers in their sixties, the newly named Philippa descended the stairs and made her way into the lounge.

Both men grinned from ear to ear when they first laid eyes on her. Pink platform high top running shoes with a three inch rubber sole, frilly ankle socks, a black and red plaid micro-mini skirt and a tight white blouse all conspired to give the captive teen the look of a tranny schoolgurl. The two men stood and approached Philippa, nodding their heads in approval of her look and what it represented in terms of her development into a feminized sissywhore.

“Excellent Philippa” Cedric cooed... “just excellent.” For his part, Dr. Andrews reached under the slave’s miniskirt and enclosed the teen’s chastised balls within the grip of his left hand. Squeezing just hard enough to create distinct discomfort getting Philippa’s attention, Clive looked at Cedric and in a lust-filled growl said “get the bitch to sign the papers now...I’m going to need to pump another load into her with her looking like such a sexy fucking cunt.”

Cedric produced a thin file of papers and proceeded to tell Philippa that he had decided not only to enslave the teenager, but also to transform her from the thin, innocent male Philip into a feminized whore of a sissygurl slut who would be named Philippa. To that end, she was to sign the papers in the folder formally changing her name both legally and permanently. She was going to be manipulated physically and psychologically at the hands of her own personal psychiatrist to become the complete property of Master Cedric. A hyper-sexualized cross-dressed and feminized male slave to be degraded used and raped whenever...however...and by whomever, her Master decided.

With the papers signed and sealed, Clive dragged Philippa over to the couch and told Cedric to stuff a gag in her mouth while he took another ride in her sissy-cunt. The retired teacher pushed what looked like a deflated black rubber balloon attached to a hand pump into the slave’s mouth and began squeezing the bulb over and over. Seated deep inside Philippa’s oral cavity, the ever-expanding rubber bladder needed no strap and buckle arrangement to stay in place. Lodged behind her teeth as it grew in size it locked itself within her mouth, causing her cheeks to bulge outwards with each successive squeeze of the inflation bulb. When fully expanded Philippa’s jaw felt like it would dislocate and she was completely silenced - unable to utter a single solitary audible syllable.

While Cedric had been shutting the bitch up with the inflatable gag, the retired doctor had been bending her over the back of the couch, pushing up her miniskirt, and kicking her legs as far apart as they would go. Pinioned over the high back of the couch, the little slave’s pink high tops dangled in mid air as Clive once again freed his thick eight incher. Stroking himself to full erection with some silicone lube, the 67 year old peeled back his foreskin and exposed the large purple head. The lustful edge having been smoothed over a bit by his first orgasm of the day, his entry into Philippa’s hole this time around was much slower, smoother, and caused a great deal more stretching of the sissy’s hole compared to the first anal rape she had endured. While Clive could feel the tension in the slut’s body continuously increase as she struggled to open herself to the girth of of the doctor’s cock, absolutely no sound was heard as the rubber gag had rendered her nothing but a living, breathing, struggling cum receptacle.

For nearly thirty minutes the perverted psychiatrist worked and stretched and opened the sissygurl’s pussy. Sometimes pulling all the way out and watching the gaped open asshole twitch like the mouth of a fish out of water, and sometimes ramming all eight inches in and out repeatedly and long-dicking the captive teen, Clive revelled in the myriad of sensations the young slut’s tight anus was providing for his hard and hungry cock. Eventually the ecstasy drove him over the edge and he once again pumped a very impressive load of cum for a 67 year old man into Philippa’s accommodating cunt. Allowing himself to soften while still in her hole, Clive eventually allowed his cock to slither out of the freshly fucked cunt like a snake and made his way around to wipe himself clean in the exhausted teen’s wavy hair while Cedric worked a fat silicone rubber plug into the gaped fuckhole to keep it fully loaded with the doctor’s mancum.

Buckling up his pants and donning his overcoat, Philippa heard Dr. Andrews bid farewell to Master Clive with a statement that filled her with dread... “well enjoy the rest of your evening my friend...I’ll be round at five o’clock sharp tomorrow afternoon to collect Philippa for our evening together...I can’t wait for us to have more quality time together!”

After Dr. Andrews had left Philippa was placed on her knees in front of Master Cedric to receive her instructions regarding what she was to make for him for dinner, and what other chores she needed to attend to before addressing her owner’s desires. She was also informed that as part of the deal for all of the help Clive had provided in securing her obedience and for the help he would yet provide in perfecting her training as a wanton sissywhore faggot, she was to spend a full 48 hour period under his direct control each week until further notice. Dr. Andrews would be taking her back to his place the following evening, returning her home by five o’clock two days later. For the duration of that time, she belonged to him, and would cater to all of his perverted and sadistic whims. Unbeknownst to Philippa, the sessions spent with Dr. Andrews would also involve deep psychological training and manipulation to cement her subservience to the two men...intensify her feelings of shame and humiliation at being turned into a feminized tranny slut, and break down her very intelligence so that she would end up a hyper-sexual ultra-obedient sissygurl bimbo-whore to be subjected to any and all degradations imaginable.

Philip...was gone. The life of Philippa, was just beginning.

Having prepared and then served her Master’s evening meal, followed by doing all of the washing up and tending to the preparation of his final cup of tea for the day, Philippa now found herself on her knees between Cedric’s legs while he watched the evening news...nursing on the old man’s cockhead and slurping up all of the pre-cum that leaked and oozed out. She had been at it for an hour and a half with the old man relaxing and enjoying the hot wet mouth on his hard cock while the obedient slut periodically thanked him for allowing her to taste and swallow and enjoy the dick-honey that he was feeding her. Still dressed in her schoolgurl outfit, the sadistic old pervert finally decided it was time to get some sleep...with some help from his sissybitch to help him drift off.

“Get upstairs and strip yourself naked Philippa and hang your outfit neatly in the closet. After you’ve done that join me in my bedroom and be quick about it - if you keep me waiting there will be severe punishment coming your way I can promise you that!”

By the time the sissy had made her way into the Master’s bedroom, Cedric was fully prepared for what he had in store for his slut. He ordered her to lay on her back on the bed, and he placed a long broomstick behind her neck so that equal lengths of the wooden rod telescoped outward towards each side of the mattress. Climbing on top of the young slave, Cedric grabbed hold of one of Philippa’s legs and positioned her ankle behind the broomstick. Repeating the process with the other leg, the slave was now jack-knifed on her back, with the forward pressure from both of her restrained ankles being matched by the backward pressure of the wooden bar behind her neck. Although the arrangement was causing her immense unrelenting neck pain as well as such a stretch behind her thighs and calves that she thought her muscles would rip in two, Philippa was powerless to free herself. Once Cedric had also secured her wrists to the headboard with a coarse nylon rope that was biting into her flesh, She was at the Master’s mercy until he decided to let her go.

Alighting from the bed, Cedric casually went about retrieving a diabolical looking gag from his bureau. It was made of metal and had been based on an instrument commonly used in dentistry to assist a patient with keeping their mouth open for the duration of a long procedure. In Cedric’s version, the device once seated behind Philippa’s teeth both top and bottom, and ratcheted open, was very nearly dislocating the teenager’s jaw and forcing her oral cavity into a grotesquely huge silent scream.

Merely the preparations for the evening rape had caused the 62 year old’s 6” cock to stiffen in his pants, and once he had climbed on the bed after removing his clothes his erection was very nearly causing him pain from how hard and eager it was to gain access to the trussed up sissy-gurl’s cunt. Slobbering all over his fingers and using his spit to lube up his cock, Cedric leaned over Philippa and she felt his body weight on top of her as his hips humped and thrusted in an attempt for his iron bar to find the opening to her pussy. The old man grunted and sweated as eventually his weapon hit home and speared the young sissy like a harpoon. Philippa’s eyes squinted shut from the pain as she could not utter one word of protest while her Master pumped and fucked and raped her in the bondage driven missionary position for the next 20 minutes. Roaring with pleasure, Cedric climaxed and fired volley after volley of searing hot cum deep into his slutgurl’s open hole. Three, four, five full shots of the 62 year old’s semen impregnated his bitch while he enjoyed the twitches and spasms of the anal ring that were massaging his tumescent manhood.

Exhausted and breathing heavily, Cedric rolled off of his victim and lay on his back revelling in the afterglow of orgasm. Philippa meanwhile, lay beside him still agonizingly restrained as thick rivulets of cum drooled out of her asshole. She silently begged for Cedric to set her free but the retired old pervert was not done with her just yet.

Returning once again to the bureau where he had kept the dental gag now prying apart Philippa’s jaws, Cedric procured yet another item which the slave could not see from her vantage point on the bed as the old man’s back was to her. All she could make out was what looked like a belt being buckled around Cedric’s waist...until he turned around.

“I saw how much fun you had slut being fucked by Dr. Andrews today with his big juicy cock. I know that you were thinking to yourself that you were happy to have a big thick cock stuffing that cunt of yours compared to the tiny little cock your Master allows you to enjoy! Well...I won’t have any slut of mine enjoying some other man’s cock more than she enjoy’s being worked and stretched by her Master!”

It was then that Philippa saw what was hanging between Cedric’s legs.

Suspended there by the leather belt he had buckled tightly around his waist and dangling ominously between the retiree’s thighs was a huge black rubber cock that measured no less than 10 inches in length, and appeared to be the girth of an aluminum can. Holding it menacingly in one hand as he approached the bed, Cedric made a pronouncement that caused Philippa to struggle and strain against her bindings, fruitlessly trying to get away from Cedric as he joined her on the bed.

“Let’s see how you feel once you have all 10 inches of your Master Cedric’s big rubber tool prying open that tight little snatch of yours bitch...that will teach you for coveting another man’s penis over that of your one true owner.”

Philippa would remember very little of the rape that ensued, except for the feeling of the large heavy dildo beginning to push at her freshly fucked pussy lips, and then a blinding white light as her Master rammed all 10 inches into her in one brutal stroke. The 62 year old continue to pummel and pound the eighteen year old’s anus with the enormous rubber strap on for nearly an hour, leaving her face streaked with tears and her obscenely stretched open mouth drooling like crazy from either side. By the time the old man was done with her, he had become erect under the strap on and climaxed one more time, pumping his pulsing hot stream of semen onto the crack of Philippa’s ass behind the distended orifice that had been her tight anal ring.

Yanking the heavy rubber dong from the teenager’s hole and with it still dangling in front of him like an obscene mucus slicked weapon, Cedric released Philippa’s chafed wrists from their bonds, slid the broomstick out from behind her neck, and removed the dental gag from her mouth. Nearly dragging the exhausted teen from the bed and the scene of her most brutal rape to date, Cedric kept his slave doubled over with a firm handful of her hair in his grip as he marched her out of his room, through the house to her bedroom door, and threw her inside. Philippa heard the locks being slid into place, and after thirty minutes on the floor barely able to move managed to drag her self to her bed and allow exhaustion-laced sleep take her.

• - - - - - - - - - - - - - - - - - - - - - - - - -

Philippa shifted her weight uneasily from side to side as the clock in the front hall read just two minutes to five in the afternoon. Part of the reason she was so uncomfortable was physical…Master Cedric had made sure that all of her shoes were two to three sizes too small. He said it made her feet look more petite like a sissy’s should, but also had the added pleasure for him of ensuring that she was in some degree of pain with every step she took in service to him and his friends. The other part of her anguish was mental…Dr. Andrews had said that he would be by to collect her at five sharp, and master Cedric had ensured that she was standing in the hall, ready for her Psychiatrist appointment, for the last thirty minutes.

On the slave’s feet were a shiny pair of patent leather maryjanes, buckled and locked into place over top of knee high white socks. She had a light pink t-shirt on underneath her powder blue shorty overalls, and the crinkling waxy garment hid more elements of torment that her Master had applied at Dr. Andrew’s request.

Philippa was now completely hairless below the neck, something that Master Cedric said would become permanent after a few more applications of the depilatory cream that had robber her of all of her body hair that morning in the shower. Stuffed into her cunt was a large silicone rubber egg plug, and her sissy balls had been rubber with a generous amount of arthritis heat rub to make them bun and itch horribly. The same cream had been smeared around her thickening cunt lips to make them inflamed and swollen…something sure to make Dr. Andrew’s horny and excited for the little sissy’s pussy according to Master Cedric.

Cedric had made Philippa watch in the mirror as he did her hair for her date, advising her that she would very soon be responsible for doing it herself as well as her make-up so she had best pay attention if she knew what was good for her. A severe part down the middle had been drawn as if by a razor, and the strawberry blonde locks had been pulled into two pigtails so insanely tight that it felt as though the strands would tear out from her scalp at the roots. They were tied with pink and blue ribbons, and shiny lip gloss had been caked onto her lips making them appear pouty, wet, and eager to be kissed. A ring gag was buckled tightly into place, and no collar had been added as Cedric said that Dr. Andrews would be taking care of that personally when he arrived.

When the doorbell rang, Philippa nearly peed herself. The psychological impact and control of the sadistic doctor was already strong and was bound to grow as he further implemented his portion of Philippa’s training as a tranny sissy-whore. When Cedric swung the door open, there stood the portly older psychiatrist, grinning lasciviously as he spied the teenage slave trembling in the far corner.

Thick strings of drool extended from the sissy’s wide open mouth as she had been wearing the ring gag now for several hours. They had pooled into two wet spots on either side of the chest of Philippa’s pink t-shirt and she was sure she could see front of the heavyset Doctor’s pants tent outwards as he stood before her, looking down on her as she had been prepared for his arrival by Master Cedric.

“Well well Philippa…I can see by how wet that whore’s cock-sucking mouth of yours is that you are happy to see me again. Dr. Clive is going to have to make sure that wide open face-cunt of yours gets a proper workout over the next two days isn’t he slut?”

The question was rhetorical as Philippa had no means of answering anyway, and the portly old sadist licked his thick chafed lips at the thought of all he had planned for his first sleepover with Philippa as he wrapped her heavy leather dog collar around her neck and buckled it tightly in place.

After some small talk with Cedric in the front hall as the terrified teen stood there all but invisible to the two old men, Clive Andrews announced that it was time that they got going. Turning towards Philippa he drew a small remote from his pocket and gave the sissy a naughty wink as he pressed the button and delivered an electrical shock to the unsuspecting slave that caused her to drop to her knees and in spite of the big ring gag in her mouth let loose with a garbled scream of agony. Ten full seconds of electrical shock were accompanied by peels of laughter from both Clive and Cedric, as they grabbed her from either side and dragged her out the front door and into the boot of Clive’s waiting car. With the lid slammed shut, Philippa was surrounded by darkness, and felt the car pull out of the driveway beginning her journey to the home of Dr. Clive Andrews MD…a place where she would be degraded and deconstructed like no other, transforming her into a feminized, sex-addicted tranny sissygurl whore for the delights of sadistic and perverted old men.

Next…following Dr.’s orders.