Headmistress' Favorite Sport

Chapter 5

A new part of the first year slaves training was introduced as part of the plan to make them hopelessly addicted to sex. Every evening when they finished class they would be escorted to a room covered in rubber on the inside. The sissies were ordered inside unbound and unescorted, dressed only in their white stilettos, collars and corsets. The corset training was shoving results, the widest waist about seventeen inches. The first time it happened and the girls stood waiting obediently to be told what to do and voice told them that they had one hour to themselves. They could do whatever they wanted. There were only two things they really could do: they could talk or they could fuck. Some feeble attempts at conversations were made and the girls did gossip between gasps, but with the training and conditioning combined with the chemicals, these sissies could do only one thing: fuck. The hour in the rubber room was one large fuckfest and most sissies managed at least five orgasms in that time. When they were informed that playtime was over, the floor and walls of the room had to be licked clean.

The process of making the addicted to sex reached new absurd heights. The girls now had fifteen to twenty orgasm a day and the first thing they did in the morning now, was to do a sixty-nine together with the girl next to them, so that the pressure, which had built up during the night, could be relieved.

The chemical and surgical part of their treatment was coming to an end. A few had had a little surgery to correct some imperfection, but none of them now had any remotely masculine traits. All looked super feminine. Denise's tits had grown to size 36DD and she loved them. They were ever so sensitive and Denise never missed an opportunity to fondle them, bringing her nipples up to her tongue so that she could lick them.

At Christmas time there was no training. The mistresses celebrated Christmas away from the sissies and it was the policy of the school that the slave owners should have as little trouble with sissies not fully trained. At the same time everyone knew that a little sensory deprivation training would be good for the silly bitches. So three days before Christmas they all stood outside their lockers looking strange and more than a little desperate. They wore only their usual black Oxfords with the seven-inch heel and a pair of black mittens. They had tubes coming out of every orifice in their bodies: breathing tubes hung out of their noses, feeding tubes, coming all the way from their stomachs, hung out of their mouths, catheter tubes for urine came from their cocks and tubes for forced enemas and waste removal came out of their asses. It had definitely not been pleasant having them put there and most had tears in their eyes as they were sealed inside new restrictive sleeping bags made from rubber. As her helmet was strapped on Denise found that she had just as little room to maneuver as in the old sleeping bag. This one did have a very nice addition. Her cock was encased in a sheath and it felt very nice holding her erect cock. Denise's cock was always at full mast these days and she was horny all the time. As both she and the others got better and better at performing sex, her orgasms got better and better and her sexual appetite grew. Sex was rarely off her mind. The only thing that was an even greater presence in her mind was the need to obey. Not only was it hammered home in all the lessons she had and in the nightly messages to her subconscious mind, the memory of Erica's fate was etched on her mind.

As she was slid into her locker the messages began inside her helmet and suddenly the sheath around her cock came alive, giving her the first of a long row of magnificent orgasms. Denise and the others were sealed in their rubber cocoons for more than twelve days, until normal routines were resumed after Christmas. As they lay there the boundary between dream and reality blurred. Food, air and enemas were pumped into them, while urine, semen and shit was pumped out. They were unable to stop or help any of it. Time passed as series of images and words to condition them, punctuated by a series of pumping events: food, air, shit, urine and semen from fabulous orgasms.

When they were removed from their cocoon all were completely disorientated, with stiff muscles and joints. But lessons started as before and the rules were the same: obey immediately or face the painful consequences and they quickly and painfully caught up.

Their sex training was now quite advanced. They were able to bring both men and women to orgasms using most of their bodies – if not exactly their minds.

It was time for the hopeless little sexpots to get some real life experience. The academy ran a whorehouse on the side and once the slaves passed a certain point, they spent most evenings and nights in this establishment earning money for the academy. This meant that they slept a great deal less now they were up most of the night entertaining guests. But this they had to able to cope with as well. It was expected of a slave to be able to perform her duties perfectly without sleep. At first it was dreadfully hard doing with only a few hours of sleep, but helped by ruthless punishment they soon got used to it. So their daily routine changed a little: first release, breakfast and morning enemas and baths, then lessons followed by an hour of breathless sex with the other first year sissies, followed in the evening by duty at the whorehouse.

The whorehouse got many different kinds of customers. Most just wanted straight sex, usually blowjobs and cunt lappings. Denise had a very talented mouth and was quite popular among that category of customers. Most were intrigued by her penis, but usually only the women dared touch it. The men who paid for a shemale whore were usually more than a little insecure about their own sexuality and rarely had the courage to touch her cock. Another kind of customer was of course the sadists who took great pleasure in torturing and humiliating her. Again Denise was popular because of her extreme obedience and complete submissiveness. The torture at the whorehouse was invariably mild compared to what she was subjected to at the academy and bouncers always stood at the ready in case a customer went berserk.

Denise for her part liked working as a whore. She felt (as she had been conditioned to feel) that she was a filthy whore and this was a fitting place for her to work in. Also she liked sex in all the forms it was performed in at the whorehouse. She was rarely allowed to cum while working. The customers were not interested in giving her orgasms and Denise knew better than to cum without permission, so she always left the whorehouse feeling terribly horny. This was usually taken care of just before she was sealed inside her locker, where the sissies were allowed to masturbate before being tied up.

Denise had also become somewhat of a teacher's pet. Both Headmistress von Kaltenbrunner and Mistress Hoffmeyer frequently took her aside as entertainment for the night. Their ideas of entertainment were vastly different. Mistress Hoffmeyer was surprisingly vanilla in her private tastes. Sure she liked to see Denise grovel at her feet and she liked humiliating her, but mostly she just tied Denise up in some way and either fucked her ass or her face, even giving her reach-arounds when she fucked her ass. Denise soon developed warm feelings for Mistress Hoffmeyer and she in turn seemed to prefer Denise over most the other slaves, with the exception of Cindy. Cute little Cindy was everyone's favorite and the girl soon developed almost stress-like symptoms having to please so many people. But there was no mercy; she was slave and she had better perform.

Headmistress von Kaltenbrunner seemed to prefer Denise even at Cindy's "expense". Her sessions with Denise were of a very different kind than those with Mistress Hoffmeyer. Regina von Kaltenbrunner did not have a single vanilla bone in her body. She enjoyed the pain and humiliation of others above all else and Denise saw her fair share of it. But the sessions were not without rewards for Denise and in fact she was almost always allowed to cum during them. But her orgasms with Headmistress were very different. With Headmistress she only came while screaming in pain and after a few weeks Denise reached the stage where pain and pleasure became inextricably linked. Every whipping fuelled her lust and every orgasm reminded her of intense pain. And always present with Headmistress was the unfortunate Erica. Often Headmistress would warm up with a bit of torment for Erica, a whipping or some needles stuck in her sensitive parts. While Headmistress warmed up on Erica, Denise would kneel with her hands clasped behind her back, her tits out and her head bowed, obediently waiting her turn. A favorite of Headmistress was using a riding crop to whip Denise's erect member to orgasm. Usually her balls had been mercilessly tortured first, but Denise was such a horny bitch that it mattered little for her ability to get hard. But every time Headmistress even looked at her balls Denise feared castration. It seemed like Headmistress could barely contain herself when she had testicles in her hand and it scared the shit out of Denise. An hour with Headmistress was an hour in constant fear of castration. At the same time there was no doubt that Headmistress was by far the most accomplished of the mistresses. She had an air dominance matched by none.

The rest of the time went by in an endless stream of sex and submission. She was becoming such an accomplished little slave-slut that sometimes Denise wondered what the second and final year at the academy would be spent doing. She did, however, have no doubt that Headmistress had something planned. One thing that disturbed her the few times her bimbo mind actually worked and she had time to think, which was just as rare, was their incessant orgasms. Why were they being forced to cum all the time? Surely slaves rarely if ever came?

At the end of spring teaching at the academy briefly halted as their mistresses and masters came to the academy for a celebration. A celebration for their owners and the staff that is. The slaves were the entertainment. At the party Denise saw not only Mistress Rachel, Mistress Joanna, Mistress Jocelyn and Master Tony. She was also thoroughly fucked by Cindy's owner, Master Rick. Master Rick was the biggest man Denise had ever met, a huge, black and enormously stylish and handsome. Denise had no trouble seeing why Cindy had fallen for him or his fabulous cock. It made Denise gasp for air as it filled her completely as he pounded it far up her ass. As she licked it clean afterwards she found herself thinking about Master Tony and how she would love to be fucked by him again. Of all the people back home she had missed him the most. She longed to be held tightly by him, kissed and fucked; to be allowed to show what a good, little slave she had become.

The party also proved that Master Rick and Master Tony were not the only ones who had the killer combination of charm, good looks and a huge cock. Yvonne's owner was more than a match for either Master Rick or Master Tony. Master Richard was Yvonne's uncle. Yvonne's name had originally been Malcolm and when he had been eighteen his parents had died. He had no other relatives than his sister's brother Richard who had invited him to stay until the matter had been sorted out. Maloclm had always been a very small and lonesome kid without any friends. He had just finished high school and needed to find out what to do next. Uncle Richard had offered to let him stay while he did this. During this stay Uncle Richard had used the opportunity and enslaved Malcolm. Richard was a huge guy with slightly curly brown hair and blue eyes. He had a moustache and Malcolm was no match for him. With Malcolm crying and begging Richard threw out all Malcolm's boy's clothes and forced him to wear girl's clothes. He forced him to wear heels and make-up to and insisted he only speak in falsetto. Malcolm tried rebelling and running away, but Master Richard, as he now had to call him, never gave him a chance. Instead he punished Malcolm mercilessly and soon Malcolm was too scared to try. Master Richard now fed Malcolm large doses of hormones and gave Malcolm a new name: Yvonne. Malcolm hated it, but soon got used to referring to himself as Yvonne.

In the beginning there had been no sexual advances from Master Richard, but as Yvonne developed feminine features these started as well. First it was only kissing. Master Richard spent hours kissing Yvonne, running his hands over her body. At first Yvonne didn't like it, but as the hormones began to work she gradually gave in and kissed back with increasing fervor. The turning point came one evening when Master Richard took Yvonne's cock in his hand. Yvonne was standing next to Master Richard's chair in the living room, dressed in a small white bra and a pair of tiny silk panties. On her feet were white mules with five-inch heels. Yvonne had her hands behind her head as Master Richard had ordered. He expressly forbade that Yvonne touch her genitals without his permission. Lately this was becoming a problem as Yvonne became more and more horny. She would wake up in the morning with a hard-on that just wouldn't go away and most days it wouldn't go away at all. All day Yvonne ran around with a huge hard-on in her pretty panties. Master Richard kept her chained by the neck to her bed at night, a baby's bed with bars and like babies Yvonne wore little mittens so she couldn't use her hands. Now she stood beside Master Richard's chair with her mittened hands behind her head as he took out her rock hard member. As he held it pre-cum spilled from its tip and Yvonne let out a little moan. He looked at Yvonne and asked: "Do you like that? Do you like your Master touching you like that, you filthy little slut?" In a breathless falsetto Yvonne answered. "Master, oh yes, Master, ohh, ohh." Yvonne could barely control herself as Master Richard masterfully kept her on the edge for long time before allowing her to cum. Yvonne came with girlish shriek, and she jerked and spasmed before her legs buckled under her and she almost fell.

After that it had been easy. That same night she had moved in to his bed where he had taught her how to give him blowjobs. Motivated by the prospect of Master Richard touching her, Yvonne submitted to him. Soon he fucked her ass and when he told her that she was going to the academy, she didn't resist. As she left for the academy there had still been a remnant of Malcolm. The remnant of Malcolm had still wanted to escape but of course it had been too late. The remnant was eradicated and instead Yvonne found out that she was a very submissive girl. When she had seen Master Richard she had actually shrieked with pleasure. Like Denise she longed to show him what a good little slut she had become.

Master Richard took an instant liking to Denise. As there seemed to be an unspoken agreement that the mistresses and master would not use their own slaves on this evening, he left Yvonne in the capable hands of Joanna and Jocelyn, and grabbed Denise by her throbbing cock and guided her to a chair in the corner of the room. Here he had Mistress Gibbons fist Denise while Denise deep throated him. Denise enjoyed it immensely as Master Richard's huge cock filled her throat while Mistress Gibbons' arm filled her ass. Headmistress made the experience perfect by joining the fun. She had Denise lift her leg so that she could whip Denise's throbbing member, thus providing her with yet another fantastic orgasm, where pain and pleasure blended until Denise had trouble separating the two.

As the orgy wound to a close all the sissies were lined up along one wall of the room, their mistresses and masters watching them as Headmistress once more took center-stage. The sissies were all feeling very nice. Most had been allowed to cum and all had performed the duties for which they had been trained.

As Headmistress spoke the mood changed, at least among the sissies: "Dear friends and colleagues", Headmistress began. "I hope you have all enjoyed the evening and that you are all satisfied with the progress your sluts have made?" A general murmur of agreement rose from the gathered mistresses and masters. "Today marks the final major transition for the useless, little bimbo's: the day when they get their chastity devices fitted." Denise, like all the others, was suddenly deprived of her good mood. As Headmistress finished the last sentence she pointed to a gynecologist's chair situated in the corner. By the side of the chair stood Mistress Hoffmeyer with a tray filled with what was unmistakably a collection of chastity tubes. As if to remind them of their situation Erica stood by the chair too, her now tiny and useless sex brutally constricted by a piece of steel wire with a four-pound weight hanging from it.

The sissies began to cry, but none were undisciplined enough to beg or plead. All lined up in front of the chair and one by one they were fitted with the devices that most would wear more or less constantly for the rest of their lives. Denise cried inconsolably as Mistress Hoffmeyer placed an ice pack on her cock to make it shrink, after which she squeezed the small tube down over it, two small, sharp metal bands holding the head, which stuck out the end of the tube. Her balls were squeezed together by a steel wire mesh connected to the chastity tube itself by a steel wire. A small lock at the back of the tube secured the two parts to each other and insured the device could not be removed without the key. Once the device was on, yet another steel wire was secured to the tip of the tube. This was then pulled back between their legs and secured to the back of their corsets, leaving them with smooth crotches.

Denise was miserable and desperately wanted to beg to have it removed, but one look at the twins convinced her that this would be a very bad idea. They had the look of someone just waiting for an excuse to punish her. Mistress Rachel and Master Tony looked at her expectantly too and Denise knew what was expected of her. She took her cue from the weeping Cindy who was on her knees kissing Master Rick's shoes as she thanked him for her new chastity device. Denise fell to her knees and began thanking everyone involved. First she crawled to her owners and thanked them all for teaching her how to be a better slave. Then she crawled over to Mistress Hoffmeyer to do the same. Finally she crawled over to Headmistress and thanked her as well. Denise was the first sissy to think of this and Headmistress noticed that Yvonne was hot on her heels. As Headmistress accepted their thanks, she considered the benefits of the castration session with Erica. It had certainly been a major factor in insuring the complete and total obedience of these two little sluts.

It hadn't been the first castration Headmistress had performed, but the second. The first castration had been performed on that useless piece of shit she had married, several years ago. The marriage had produced two daughters, both of whom took after their mother. Both now worked as professional dominants and one of them, if not both, would take over running the academy after her. But her husband had been another story. He had actually been working as a dominant when Regina had met him, and at first he had seemed perfect for her, a man as domineering as herself, and they made a good couple. But after a while she had discovered that he was softer than her; less demanding of slaves and more likely to let them get off easy. The discovery made her despise him and when her daughters had been born and she had decided on not having any more children, she had finally had enough and had broken him. Catching him unawares, she had subjected him to a torture session lasting one whole day and night, where she let him know what she thought of him and his softness. The session had ended with her castrating him. She hadn't bothered feminizing him, but instead sold him to a bull queer as a slave. She knew from reliable sources that the man she had sold him to was cruel and sadistic enough to insure that the creep got what he deserved. A few years later she had heard that he had accidentally choked to death while being forced to deep throat his master. Regina thought it a fitting end to the useless asshole. As for her daughters, she had told them a lie when they were small, but when they reached adulthood she had told them the truth. Both had by then figured that the lies they had been fed as young had been just that, and neither was surprised at their mother's admission. Neither had been shocked or disturbed. They were both so dominant that they accepted their mother's way of handling the creep as the best solution.

Regina von Kaltenbrunner considered this as she looked down on the succession of sissy bitches crawling past as they thanked her profusely. She had enjoyed the session with Erica and the effects on the slaves were magnificent. Maybe she should turn it into a tradition? She considered it some more she stood watching the owners saying goodbye to their property as they left the academy. When the last owner had left the sissies stood lined up along one wall, heads bowed, breasts out, waiting for orders. Before sending them off to sleep an hour or two before classes resumed the next day, she inspected them. Yes, they were definitely a useless bunch of little sluts, but at least they were turning into obedient little sluts. Headmistress stopped in front of Denise and calmly said for all to hear: "When your period of commercial usefulness is over, and if someone hasn't beaten me to it, I'm going to find you, buy you and castrate you." Denise's mind went blank with fear and she lost control over her bladder and bowels. And since she wasn't fitted with a butt-plug, she shit and pissed on the floor out of pure terror. She wanted to scream, but was unable to make a sound. Headmistress looked serenely pleased that she had scared Denise out of her mind and spoke to Mistress Hoffmeyer: "Make sure that she cleans it up before she is punished. Punish her until its time to start the lessons." Then she left the sissies in a state of shock. None were undisciplined enough to look at Denise, but all wanted to. Denise was certainly the teacher's pet – in the wrong way. Denise was so scared that she barely remembered eating her own shit of the floor or the severe punishment she received after that. She could see herself ending up as Erica and the prospect terrified her utterly. She knew she was just as worthless slave and that she wasn't worthy of the attention of such fine people as Headmistress. And Denise loved being a slave, loved having no control over her own life, submitting to everyone. She loved being an object, something others used for their own purposes and she knew now that her life as a slave would afford her very few, if any, orgasms and she accepted that. The feeling, the urge, the raw sexual need would still be there and would not only have to do, it was part of the thrill of being a slave. But being castrated and robbed of even the possibility of getting pleasure out of sex, would take away all pleasure in being a slave. Erica's situation was too extreme, too absolute. And Denise knew that Headmistress meant what she said. She would find her and castrate her if it was within her powers and there was nothing Denise could do about it. Her hope was the worst hope of all. If she was to avoid being castrated by Headmistress there were only so many options. There was the possibility that she would wind up with a mistress or master who would want to keep her for the rest of her life. Denise dreamed of this. She dreamed of being kept as a slave by Master Tony for the rest of her life. When her bimbo mind worked, she admitted to herself that this was unlikely. There was every indication that Mistress Rachel and Master Tony had had several slaves before her and would have more after her. Besides Mistress Rachel would probably see a slave who loved Master Tony as competition, insuring that the slave would move on quickly. Then there was the possibility that another mistress or master than Headmistress would castrate her. This was somehow a prospect that was even worse, because she couldn't imagine someone more suited to perform such a task. Finally there was the possibility that she would be killed, either on purpose or by accident, before Headmistress could get to her. All the options were terrible and brought home the harsh reality of being a slave. Denise thought of these things as Mistress Hoffmeyer released her from her bindings and led her to class after a long night of punishment. Denise was terribly depressed. It seemed like her whole life had just been robbed of all pleasure, that all she had to look forward to was pain and suffering. Thinking about this her conditioning kicked in. She was a slave. This was no more than she deserved. And besides, wasn't castration the ultimate in domination? Wasn't Erica's submission the most complete Denise had ever seen? Suddenly the prospect not only scared her, it turned her on as well. Denise was confused as Mistress Hoffmeyer pushed her into the classroom, but her submissive side was clearly taking over. She was literally scared shitless by the prospect of castration at the hands of Headmistress, but she was also beginning to accept it as her inevitable fate.

The punishment only continued, as neither she nor any of the others were able to perform properly wearing their new chastity devices. Of course Denise had other things on her mind as well, but she too was unable to do her duties as well as ordered wearing her new chastity device. Her cock, used to more than fifteen orgasms a day, constantly tried to get hard and she was slick with pre-cum. Not only was it completely maddening, but it was also very painful.

Their training took an entirely new dimension. Now they were not rewarded for good performance or behavior. The reward was the absence of punishment. Or rather the absence of further punishment, because now their chastity devices provided a constant punishment to them all. They were so used to having orgasms all the time that their cocks tried to escape their imprisonment all the time, a very painful process. Humiliating too, as their cocks let out a steady stream of pre-cum so that their thighs became wet with it. When the lessons did not require them to be impaled by a cock, dildo or other such things, they now wore panties holding sanitary napkins. These napkins had to be changed at least five times a day, soaking wet from pre-cum.

The training continued along the same lines in some ways, with a lot of demanding sex and obedience training and they still served in the whorehouse at night. But new things were added to the training as well. The training began to include lesson, which imparted them with real skills other than sexual ones. They learned how to clean and cook and keep a proper house. They learned secretarial skills, like typing and taking dictation. All things, which could be useful to their mistresses or masters. The lessons of course all had that sexual slave twist. The cleaning and cooking had to be performed while wearing constrictive rubber suits and dictation was more "dick-tation" since they scribbled while kneeling between the legs of a mistress or master, giving blowjobs or eating pussy. And new items had been added to their daily uniforms: Firstly they now wore giant butt plugs. Secondly their ankles were now always connected by a ten-inch chain and finally their collars had now been fitted with their nametags. Their nights were still spent in the little meat locker being conditioned.

Their first year at the Kaltenbrunner Academy wound to a close and as their mistresses and masters came to collect them for the summer holidays, there was yet another orgy. Denise and the others again were fucked and tormented for a full night, but unlike last time none were allowed to cum. As the party ended Denise was gagged and hooded, her arms tied in a backprayer and her legs strapped together and she was thrown in the trunk of Master Tony's limousine. She slept as they drove home, dreaming of being allowed to suck Master Tony's beautiful cock.