The Hacker

Another month went by, and Philip's routine as a servant maid started to feel normal to him. Due to the torments he'd gone through, all of his previous life as a twenty-year-old boy and as a college student became blurred and distant in his mind. While it would've been impossible to identify as Peach, he accepted to be called Kathleen. Although the name had been chosen by Charlie, he liked it and asked the others to call him like that. After a while, even Rob and Samantha started to use it, and in his thought even Philip wasn't sure to see himself as a boy anymore. He visited his parents again, this time escorted by Rosie and dressed like a normal girl, wearing a cream blouse, a brown plaid skirt, and a pair of nude heels, and they finally accepted him.

Of course, Rob hadn't given up his plan to feminize him. One day he was summoned to his office, and once again he was given the same choice. The result was a vocal cord surgery that changed his voice for good. He wouldn't be able to speak with a man's pitch again. Rob found this funny and made him speak as often as possible. Surprisingly, the chance in Philip's voice had bothered the boy even more than the breast implants, if not even more than the face feminization. He got used to the new pitch, but he never grew to like it.

"So, I hear you'll turn twenty-one next week," said Rob while Philip was serving breakfast.

"She's so young," said Samantha, looking at his slender feminine body.

"Ahem, yes sir," confirmed Philip.

"You've been a loyal and obedient maid for over half a year," continued Rob. "We've decided to throw a big party on your birthday and introduce you to our circle of kinky friends. Don't get me wrong, though. It won't be your birthday party. That would be silly for maid. No, you'll be the attraction of our party."

Philip lowered his eyes in defeat. Every time that he stopped hating his situation and got used to something, they found a new way to humiliate him. However, they didn't want to tell him more about what they were planning and preferred to keep him on the edge over the following days. He tried to get some more information from Rosie, but she either didn't know anything or had been told not to tell him what it was. Anyway, he knew it'd be unpleasant.

On his birthday morning, he was relieved from duty and spent the whole day getting prepared by Rosie and Irina, who'd been called back for the occasion. First, they died his hair of a lighter shade of blonde and brushed it until it was smooth and silky. Then they applied a heavy make-up on his face, so heavy that at the end he looked like a porcelain doll. His skin was almost white, and his lips were cherry red. His body was already smooth, but they oiled and massaged it to make it extra soft and painted his nails of a bright red matching his lips.

Much to his horror, they locked his penis and balls into a small chastity cage. Technically, it was useless, since the hormones prevented him from getting hard, but he knew it was meant as an aesthetic accessory and a part of his outfit. His waist was squeezed into a particularly tight white corset, even tighter than his usual ones. The corset only covered his waist, left his tits uncovered, and was locked behind his back with a small padlock. He soon understood that all he was going to wear was meant to show off his body rather than cover it. So, he didn't get any panties, but only a white garter belt and ultra-sheer white stockings that made his legs look diaphanous. His feet were placed into a pair of white ballet boots, which were locked at the ankles with two other small padlocks. A huge white hairbow, a tight white collar, also lockable, and a pair of princess-long white gloves completed his outfit for the party.

However, there were still some accessories left. They pushed a huge red ball gag into his mouth, forcing his lips wide open. They placed two nipple clamps on his tits, making him moan with pain and discomfort. A gigantic rubber dildo was forced into his ass, making him suffer even more. Finally, his arms were locked behind his back with a pair of metal handcuffs and his boots chained together with a short metal chain. When they were finished, Irina and Rosie turned his chair towards the mirror and let him take a good look at the result.

If his mouth hadn't been stuffed by the ball gag, he would have gasped. Even though he'd got used to his new female look, he still couldn't recognize himself this time. The bondage doll in front of him look unreal, almost cartoonish. He blinked and moaned, which were the only actions he was allowed to do in that gear. The two women helped him stand up, but there was no way he could walk on those ballet boots. Even without the handcuffs and the ankle chains it would've been hard, but that way it was impossible. So, Rosie and Irina had to stand next to him and support him as he moved. He did so very slowly, placing one trembling heel in front of the other. His legs and feet started hurting even before leaving the bathroom, and he hoped he wouldn't be forced to walk during the party.

"The party will start in a few hours, but Mr. Paulson told us to get you in position as soon as we were finished," said Irina. "I'll go, but don't worry. Rosie will keep an eye on you and check you don't faint or choke."

Philip moaned and shook in horror. He'd have to wait for hours in that horrible outfit! The sole idea made him sick. However, there was no way he could resist, given his conditions. They carried him to the main floor, which took forever in the ballet boots, and they made him stand in the very center of the living room. A long chain had been secured to the roof through a hook and was dangling in front of him. Irina took it and connected it to his handcuffs with yet another padlock. Philip gave her an imploring look, but she ignored his desperate moans. So, there would be no chair for him. Not only they intended to make him wait for hours until the beginning of the party, but they expected him to stand on ballet heels and in a ball gag. Moreover, he was as exposed as he could ever be. His tiny penis was on full show in the little chastity cage, his round breast was bouncing free with the clamps still on his nipples, and the dildo was still in his ass.

Irina left, and Rosie sat behind him, feeling too guilty to look him in his face. It wasn't her fault, of course, but she couldn't handle his pleading eyes. The rest of the afternoon was poor agony. He couldn't decide what was worse. Maybe it was his mouth, that was sore and ached all the time, not to talk about the rivulets of saliva dribbling from his lips. Maybe it was his feet and legs, which were hurting as hell in the ballet boots. He kept moving his weight from one heel to the other, but it didn't really help. At least, he got used to the dildo and the nipple clamps. Once he almost lost his balance, and he would've fallen if Rosie hadn't helped him.

"Courage, Kathleen," she whispered in his ear. "It's almost seven, soon the first guest will arrive. Be strong, I'll be here for you."

And so it was. A few minutes later, the doorbell rang, and the first people entered. He was expecting a big party, but instead his employers had invited a small selection of people. They didn't care to introduce themselves to him, and he couldn't catch the names, so he identified through their look and clothes. The first to arrive was a couple in his thirties, more or less in the same age as his masters. He was a very elegant man with a strong body and looked powerful in an off-black suit. She looked more like a girly girl, all dressed up in a light pink cocktail dress and matching heels. After them, a single man in his fifties arrived. He was a little overweight, but looked very self-confident and had fast, intelligent eyes. Then it was the turn of another couple, much younger than the other one. They had to be in their late twenties and looked like supermodels. He showed off his muscles in a tightfitting black sweater and skinny jeans. She looked stunning in a crazy-short silver sequin dress and a pair of platform heels. After them, a single woman arrived. She was the older in the group, probably in her sixties, but still looked attractive in a dominatrix outfit. She wore a black leather dress, matching gloves, fishnet tights, and a pair of black leather knee boots with spiked heels. Last, three people arrived together. It was clear it was a couple with their slave. The couple consisted of a tall man in his forties, dressed in a smart casual dress and shirt, and a woman in her thirties in a white sheath dress and nude heels. The slave was a girl of Philip's age with long auburn hair and hazelnut eyes. Apart from a pair of black sequin boots with crazy-high heels, she was completely naked. She was used to it, though, because she looked quite at ease.

Altogether, there were only nine guests. They all took place in the living room, sitting or standing around Philip. They looked at him closely, but they did so as if he'd been a piece of art and not a living person. They didn't bother to speak to him and ignored his suffering when he moaned and fidgeted in his bondage gear. Obviously, they were used to that kind of stuff.

"It's really impressive," said the overweight man, standing right in front of him. He placed a hand on one of Philip's tits, sending a shiver through his spine.

The mature woman in the dominatrix outfit nodded, squeezing one of his butt chicks and then fondling his chastity cage. "Indeed. Rob had told me about this last project of his, but I really had no idea it'd be so successful."

The young woman in the silver sequin minidress cocked her head, studying him. She was sitting on one of the couches and had crossed his beautiful legs. "If it weren't for that chastity device, I'd swear she's a biological woman."

Meng, dressed in a formal maid uniform, much more expensive and lavish than her usual one, came in with refreshments. As for Rosie, she retired in the next room, where she could keep an eye on them all and be ready to intervene. Looking at the guests and trying to concentrate on them to ignore his current suffering, Philip learned a lot about their dynamic. The first couple, the one made up by the man in the suit and the woman in the pink dress, was in a Dom/sub relationship. He kept bossing her around and she didn't dare to lift a finger without his permission. As for the young couple, the supermodel one, it looked like it was the opposite, even if not at the same level of intensity. Anyway, she was much more commanding than her boyfriend.

Finally, after at least half an hour, the hosts showed up. Their look was so incredible that even Philip let out a gasp through his gag. Rob was wearing tight latex pants that did nothing to hide his huge dick, and a pair of combat boots that made him look even more imposing than usual. His perfect abs were on full sight, as he wore no shirt. Samantha was all dressed up in a black leather miniskirt, a leather crossed-back bra, and a pair of thigh-high boots. Her blonde hair was tied up in a high ponytail that showed off her beautiful neck. They looked like an erotic dream.

"Welcome, dear guests," said Rob with a smile. "We're so happy you could all come."

Much to everybody's amusement, Philip excluded, the naked slave girl got down on the floor and kissed both one of Rob's and one of Samantha's feet. As for the others, they just kissed or shook hands. Then they talked, laughed, and exchanged pleasantries as if that was a normal event. It was only after a while that the discussion moved to Philip.

"Very well, let's talk about this little one," said the overweight man.

"It's a funny story," answered Rob. "We caught him stealing some of our private pictures and we brought him here. As you know, feminization a pretty boy has been a dream of mine for some time, and Kathleen here was just the perfect subject."

"I bet you're having some fun with her," commented the overweight man with a lustful glance.

"Yes, but not in the way you think. I never touched her sexually, not even for a handjob. I just gave her a choice between that and feminization, and she's always picked the latter."

"Interesting," commented the mature dominatrix, who seemed intrigued by the dynamic.

"But tell me," said the overweight man. "You promised us a surprise concerning her."

Philip fidgeted again, desperate to know what it was.

"There will be time for that later," said Samantha instead. "Now let's have dinner together. Come with me to the dining room."

Philip moaned, knowing what it meant. Of course, they left him here, standing on those awful heels for another couple of course. He was growing angry, as that was too much even for their standards. When they finally came back, he gave them a furious look and moaned as hard as he could, fighting against his many restraints.

"The little slave is being impolite," was the mature dominatrix' dry comment. She came near and squeezed his testicles as hard as she could. The pain was devastating. Philip cried through his gag and started crying for the pain. Rob had to help him, or he would've lost his balance.

"Well done," said the dominant man in the suit. His wife, the lady in the pink dress, lowered her eyes. Philip suspected she was used to that kind of treatments.

"Let's get to the surprise, then," announced Rob. "As you can see, my little project has been more successful than I could ever hope. Over the last year, Kathleen has become a perfect lady, servant, and housemaid. However, we decided it was time for her to get some experience outside of this mansion. That is why we'd like to give her away to one of you for three months to give her a new perspective and some further training."

Philip moaned. The idea of falling into the hands of one of those guests was simply terrifying.

"So, we'll play poker, and the winner will get her," concluded Rob.

The announcement roused the general interest. It looked like everybody was eager to go back home with that wonderful little flower. As for Philip, he couldn't help crying again.

"Look at her," said the mature woman. "She really needs some training."

They sat at the card table in the living room, not far away from Philip, who could see everything from his uncomfortable standing place. All couple only got one chair at the table, so there were only five players: the mature dominatrix, the overweight man, the dominant man in the business suit, the supermodel in the sequin dress, and the husband of the couple who owned the slave girl. Rob and Samantha sat in front of them, leading the game. As for the rest of them, they took place on the couches all around. The woman in the white sheath dress told her slave girl to polish her shoes, and much to Philip's disgust she started licking it, soles and heels included. As for the submissive woman in the pink dress, she sat properly with her hands on the knees and waited patiently.

The game wasn't fast. They played until well over midnight, and when they finally stopped Philip was so sore and tight he could barely understand what was going on. He must even have fainted for a while, because when Rob approached him in the end Rosie was supporting him. The rest of the guests were standing around the boy with different expressions on their face.

"You were lucky, Kathleen," said Rob. "Anita won the game."

And with that, she pointed to the mature woman, who smiled to him. Philip's heart stopped. The idea of being that crazy woman's slave for three long months made him sick. The other guests looked displeased, but they greeted politely and left. Finally, after seven hours in that position, Rosie and Meng were allowed to unchain him. As soon as they did so, he collapsed on the ground. They needed Rob's help to lift him and put him on the couch.

"Don't bother with the rest of the restraints and just give me the keys," said Anita. "My driver will put her in the trunk."

Philip shook his head, moaning and fidgeting, but they ignored him. A huge man with dark skin and short black hair came in and lifted him easily. His strong hands felt rough against Philip's soft feminine skin. He took him outside, where it was cold enough to make him get goosebumps. He was almost naked, after all. He was placed in the trunk of a beautiful black car, where he laid alone in complete darkness. After a while, the car started. He tried to guess how long the trip was, but he was too tired and his whole body ached. It could've been twenty minutes as well as two hours. In the end, however, they arrived, and the same black man carried him inside a wonderful villa. It was even bigger than Rob and Samantha's, although the garden wasn't as beautiful.

"We'll talk tomorrow," said Anita to him as he was being carried inside. "Tonight, you can rest."

He was brought to a small servant room that look much like his old one, even if it was bigger and had a real wardrobe instead of a clothes rack. Two young pretty maids in short uniforms, a blonde and a brunette, unlocked all of his restraints. When the ball gag was finally extracted from his aching mouth, it hurt so much he couldn't even close his lips. His ballet heels, stockings, corset, and gloves were removed, as well as his chastity cage and the nipple clamps. Before he could go to sleep, though, they carried him to the bathroom and washed him up, removing the make up too. Finally, they dressed him in a pair of panties and a pink nightie and left him on the bed. He felt asleep almost immediately, even if he had a lot of bad dreams.

The following morning, the same two pretty maids, whose names were Nina and Lana, came back to get him ready. For some reasons, maybe just out of habit, he was expecting to wear the same uniform they had, but instead they went for something totally different. The outfit looked like a pink Lolita costume. Everything was pink, accessories and shoes included. The underwear consisted of a corset, panties, garter belt, and sheer stockings. The dress, who came down to just above his knees, was just ridiculously frilly. It had a huge wide skirt, short puffy sleeves, and was decorated with a cascade of big bows and ribbons. The stockings had a heart pattern that made them look even more feminine, and the shoes had ankle straps and sky-high heels. Finally, he wore pink sheer gloves and a very big dolly-like hairbow.

Suddenly, he realized a French maid uniform wasn't that frilly after all. As he paraded through the house in that pink dress, he felt sillier than he'd ever had. Anita didn't receive her in an office, like Rob and Samantha did, but instead in a very posh dining room. She was sitting at a modern-looking glass table and was reading the news on her tablet. Instead of her dominatrix outfit, she was dressed in a burgundy red pantsuit and stiletto heels. If possible, however, this style made her look even more imposing that the other one.

"Your masters did a nice job training you as a maid, Kathleen," she said while he curtseyed properly. "But I'm afraid they forgot a few very important parts in your slave education. From your behavior last night, I noticed you're not as comfortable with public exposure as you should be. That's why we'll spend these months getting you fully used to outdoor humiliation."

Philip turned pale. That wasn't going to be pleasant.

"Moreover," continued Anita, "I don't agree with Rob's silly idea of letting you stay chaste. From now on, sex will be a central part of your life as a slave. You'll learn to pleasure both men and women with your mouth and ass, and to be very confident while doing it."

Once again, Philip's face lost some color, turning as white as the wall behind him.

"And be warned, I'm not as patient as Rob and Samantha. Let me down, and you'll suffer like you've never done before. Am I clear?"

"Yes, madam!" said Philip with a deep curtsey.