The Hacker

And that set his training in motion. He could've never imagined there was so much to know about being a maid. Well, honestly most of what they taught him concerned more being a woman than a housekeeper, so it would've been easier for a girl. Still, it was hard and frustrating. He learned how to move, sit, and speak like a proper feminine servant. He practiced all possible kinds of tasks related to the housework. From cooking and serving the table to cleaning, washing, and ironing, Irina slowly turned him into a perfect maid. Next to that, he also learned about hairstyling, applying make-up and taking care of his feminine body. As for Rosie, she mostly just watched him in the afternoon while he repeated and practiced the lessons learned from Irina. She was always nice to him, but she never opened. It was obvious she was as scared as he was.

He settled into his new routine much faster than he thought. The exercises kept him busy, and he didn't have time to think. However, after a few days he started to notice something strange. He wasn't having any erection, not even in the morning when he woke up. Strange as it was, it attributed it to the stress and the strange situation he was in. After all, he was being feminized against his will. It wasn't exactly something to get hard to. He got to know the occupants of the other rooms in the servant quarters. First, the other maid, Meng, a pretty Asian girl in her early twenties. Looking at her, he also learned how his final uniform would be. It was a very frilly maid uniform, and he hated the idea of having to work in it every day. As for the other rooms, they belonged to Benny, the cook, Khaled, the gardener, and Charlie, the driver.

After two weeks, Irina changed his outfit for the first time. The dresses remained the same, but she gave him a corset to help him get a nicer figure. It was uncomfortable, but not extreme, and he quickly got used to it. What bothered him more were his new shoes. Instead of the old comfortable low-heeled shoes, he now had to wear heels. They weren't neither very high nor spiked, but they were still heels, and he felt ridiculous walking in them. Towards the end of the first month, the effects of the strict diet and all the standing housework were starting to show. If he'd already been slender, now he was very thin. He was worried if that was starting to affect his health, because he felt weak and strange. His stomach ached from time to time, and he felt urges and feeling he didn't know. It was as if there was something going on in his body, but he couldn't tell what it was.

With the second month of training came another outfit change. He got a new corset, which was much tighter than the first one. This one was very uncomfortable and didn't let him bend. He even had some problems breathing if he moved too fast. As for the shoes, the low heels were replaced by high heels. They were large ones, not spiked, but they were high, and he noticed it. He needed several days to master walking on them, but he did. Irina's strict training didn't let him any other chance. He was also surprised to see his diet has changed. For no apparent reason, they started making him eat more. It was still a very controlled and balanced diet, but now the portions were reasonable. He was happy to find a new strength flowing into his body.

As he knew by now, at the beginning of the sixth week of training the outfit changed a third time. His corset become a real torture, enclosing his waist in an iron grip that barely let him breath. He needed days to be able to do anything in it. The new shoes were stilettos. He hated the spiked heels, but of course he didn't have a choice. At the end of the second month, and much to his horror, he finally realized what was going on in his body. The new diet had caused him to get back to a normal weight, but the new fat didn't go where it was supposed to be. Or, in other words, not where it was supposed to go in a boy. His breast was obviously growing, just as his hips and thighs. It was now plain obvious they'd been giving him estrogens and testosterone blockers. It had only been for two months, so the effects were still very small, but he could see them.

"I don't want to grow tits!" he complained with Rosie when they were alone. "Even if they really let me go after three years, what would I do with a full breast and female hips?"

"But you'll be free," answered the nurse with a sad face. He realized she was going to stay there for longer, possibly much longer.

At the end of the two months, his training came to an end, and he receives his final uniform. The black dress was shorter and prettier than his old one, and of course it included a lace white apron and a matching cap. His new and definite corset was incredibly even tighter than the last one, so that sometimes he even fainted if he moved too fast. Nylon stockings replaced his pantyhose, so he received a set of garter belts too. Finally, the shoes were now sky-high platform high heels. It was like walking on stilts and after a few hours the pain was unbearable. Still, he was glad the training was over. He'd finally be free from the same routine.

The day before his real job began, they gave him a complete makeover. His now longer hair was dyed blonde and styled into a longer bob that came down to his neck. His eyebrows were dyed too and plucked even more, until they were nothing more than two thin arches. His face and skin were waxed, rubbed, cleaned, and creamed so that they were perfectly smooth and soft. And finally, he received long bright red acrylic nails. With the make-up and the complete maid uniform, he looked like a little doll without anything masculine left. He looked at his reflection and thought it felt like a very strange dream. Not a good one, of course, but a distant and scary one.

The following morning at 8 AM he was ready to meet his employers. Having been permitted to move only in the basement and in the servant quarters on the top floor, he hadn't met Mr. Paulson again. As for Ms. Kominski, he had never met her, although he'd been seen her a few times from the window of his room as she walked in the garden. He could see Irina was nervous as she accompanied him to meet them. She tried to conceal it, but after all it was obvious that her job was on the line, and those people were surely crazy enough to hurt her too.

As for Philip, who of course looked much more like a Peach than a Philip now, his heart was beating as fast as it could. He felt his legs failing him and his eyes watering for the anxiousness. The whole gear -- corset, heels, heavy make-up, and so on -- didn't help, of course. He tried to remember his training and pretend to be a mindless doll. It was much easier that way. He didn't have to think, he only had to listen and obey swiftly.

"Mr. Paulson, Ms. Kominski," said Irina formally. "May a present you Peach, your new maid."

Philip held his breath and stepped into the room. Luckily for him, the training took over and he didn't stumble. On the contrary, he moved quite gracefully on the high heels and performed a proper curtsey, greeting both of his masters.

"You outdid yourself, Irina!" exclaimed Rob with a huge smile.

"Impressive," was instead Samantha's comment, who however couldn't stop staring at the boy.

The couple was having breakfast in the living room, a wonderful and sunny space in the middle of the first floor. Rob, who started to work later -- Irina had told him everything about their needs and lifestyle --, was still in his dark blue pajamas. Samantha was already dressed in a white smart pantsuit with high heels and full make-up and jewelry. If he hadn't been terrified from her, he'd thought he was stunningly beautiful.

"We'll have a great time together, sweetheart," said Rob.

"Perhaps," added Samantha, making the poor boy shiver. "I'm sure you'll learn a lot, 'Peach'. First, not to steal stuff from strangers."

Philip's face whitened, but they didn't press it further and he was allowed to start serving them. His hands trembled at first, but after a while he was able to relax a little bit and carried out his work without any problem. Rob and Samantha didn't seem to care too much about him and mostly ignored him as they talked about their day. Still, he was very much relieved when breakfast finished, and he was able to retire from the room. As much as he hated ironing, it was better than serving coffee to the people that had kidnapped and tortured him.

The rest of the day was eventless, and the following breakfast also passed without any surprise. Just when he was beginning to think his situation wasn't that terrible anymore, he was summoned to Rob's office. It was midafternoon and Samantha was away, so he was the only master at home. Philip knocked and came in, performing the expected curtsey and greeting.

"Ah, there you are, Peach. Close the door and come here."

The boy shivered as he did as he was told. Suddenly, the shortness of his skirt, which barely covered the garter belt, made him feel uncomfortable. He could see the strange light in the man's eyes. Not having any other choice, he came closer to him. The office was large and beautiful, just as any other room on that floor, and had two large windows opening on the garden. Rob was sitting behind his desk and looked stronger than ever in his expensive suit. He was much taller than Philip, and at least twice as heavy.

"So, how do you like your new job?"

The question, asked in a casual way, caught him off guard.

"I'm very happy, sir," he answered quickly, hoping it was what Rob wanted to hear.

"I hope so. You know, Samantha wanted to have you killed when we found you. You must thank me if we found this compromise. Three years of servitude are better than ending on the bottom of the sea with a bullet in your pretty head."

This scared Philip so much he felt himself losing consciousness. His heels failed him, and he almost fell. Only Rob's intervention prevented him from collapsing on the ground.

"Now, now," he said, holding him up with his strong hands. "Let's not get too emotional, Peach. We always keep our word, so you're safe here."

The boy nodded, but he didn't look convinced.

"Well, let's get to the reason why I called you here," he said, getting back to the chair behind his desk. "I'd like to present you with a choice today."

Philip's eyes widened. He knew danger when it was so close.

"As you've been certainly noticing, you've been on hormones ever since you arrived here. Actually, I'm glad to see that we can already see the first results. Now, that is something who won't affect you too much at the end of your contract. You can just stop taking them and go back to your sad male life. However, if it were for me, I'd like to take things much, much farther."

Philip swallowed hard.

"Besides, there's also something else we'd like to do with you. You see, Samantha and I are in an open relationship and love to have new stimulating sexual encounters. If you agree to it, I'd like to get to know you better from that point of view, if you understand what I mean."

Philip was as pale as a living creature could be.

"But I'm not a monster, so that's why I'm giving you a choice. Do you prefer to take a step towards permanent feminization or give me a blowjob? The choice is really up to you, and both things will please me, so just tell me the truth. Which one will it be?"

The boy shook his head in horror. He opened his mouth, but the words didn't come. His throat felt dry, and he couldn't think clearly.

"I'm waiting, honey. If you don't choose, I'm making you do both."

Philip's head ached as he tried to make a decision. He didn't want to become a woman, but he was so feminine already. Another step in that direction couldn't hurt him that bad. The idea of performing oral sex on that horrible man, instead, made him want to throw off.

"I... I choose feminization."

Rob smiled. "Very well, I was hoping you'd say that."

The following day, Philip learned what his fate would be. He'd undergo a full-body laser therapy and electrolysis to permanently remove his body hair, face and chin included. The idea of never being able to grow a beard again make him feel sad, but it wasn't the end of the world. The treatment, however, was long and boring, even though not too painful. He did a session every day under Rosie's constant supervision.

During the training he'd been mostly separated from the rest of the team, while now he got to know them better. Meng was a shy and quiet girl. Although she was the other maid and he had to work next to her all the time, they didn't talk much. He managed to find out that she'd been hired by Samantha during a trip in Asia and then brought back with her, but she didn't want to say why and under which conditions she was working there. Benny, the cook, was a friendly man in his fifties who didn't want any troubles. He simply chose to ignore all the strange things that were going on in the house and just focused on all the money he was making. Still, he was always nice to him, so he came to like him. Khaled, the gardener, was an introvert and took even less than Meng, but Philip saw the way he looked at him, especially when they met in the evening and the poor boy was forced to show himself in his ridiculously sexy baby-doll nighties. The worst one was Charlie, the driver. He was a muscular and talkative young man full of toxic masculinity. He constantly harassed them and especially liked to torment Philip. It was obvious he couldn't wait to take advantage of him.

Towards the end of his first month of service, when his hair removal therapy was well on its way and he was getting used to his routine as a housemaid, Samantha summoned him. Rob did that every now and then, wanting to check on him, but that was the first time the woman called for him. If possible, he was even more nervous than the first time in Rob's office. At least, with him he could play the card of the helpless girl and hope for the best, but with her that strategy wouldn't work. Besides, she was the one who'd wanted to kill him!

So, it was shaking as a leaf that he knocked and entered Samantha's office. It was very similar to Rob's in shape and size, but the decoration reflected her character, being more feminine, but still very simple and elegant. The woman was wearing a cream blouse and a burgundy pencil skirt that came down to her knees. Her stiletto high heels were on the floor, replaced by a more comfortable pair of slippers. Philip, whose feet were constantly aching in his platform high heels, wished he could have that same privilege. He curtseyed and greeted as he was supposed to.

Samantha raised her eyes from her laptop and looked at him. She didn't seem angry, but rather curious and interested in understanding who was the person standing in front of her. She was so beautiful she almost hurt the eyes, but her light eyes were as serious as ever.

"You know, I didn't like this arrangement at first. It was Rob's idea, and I only agreed to it because feminizing a boy has always been his dream. At first, my only intention was to ignore you as much as I could and let him have his fun. But you know, he talks so much about you, and he seems so happy with your training, that I had to find out what it is."

She paused and studied him. It was like a biologist looking at a strange animal. Philp held as still as he could, his gaze fixed on the floor.

"Tell me, what were you thinking when you took that job?"

Philip felt tears in his eyes. "I'm sorry, madam. I'm so, so sorry."

Samantha sighed. "We're beyond that, boy. It doesn't matter if you're sorry or not. I want to know what was passing through your mind when you accepted to steal those pictures from me."

"It was just a job. It wasn't the first time. I... I guess I didn't know what it really meant."

"You see? Most of the evil in the world comes from people who don't realize what they're doing. Following orders, doing jobs, stealing little things..."

Philip wanted to cry but tried to fight back the tears. All the estrogens he was taking didn't help to control his emotions.

"I want to give you a chance. You'll spend a day with me tomorrow, acting as my personal assistant. I only have to attend a charity event, so I gave my usual team some time off and I'm in need of some help. Let's find out who you are."

"Yes, madam. Thank you, madam."

He burst into tears as soon as he was alone. While she was passing by, Meng noticed it and didn't say anything, but she hugged him. For the first time, he understood her life was at least as difficult as his own. That gesture said more than a thousand words.

"Thank you," he said, as she took his hand and helped him fix his make-up.

The following morning, for the first time in three months he was allowed to wear something different from his usual uniform. All the unpleasant parts of his clothing remained, the corset, the heels, the garter belt, but instead of his maid dress he received a white silk blouse and a black pencil skirt. The blouse was very frilly, having puffy sleeves and a lot of lacy hems, and the skirt was very short, coming to only mid-thigh, but at least it was a presentable outfit. He looked like the sexy secretary from a porn movie, but it was still better than a maid uniform.

Due to his different tasks that day, he was relieved from his breakfast duty and met Samantha directly in the hall. The woman was stunning in a light pink sheath dress and matching heels. She looked at Philip and nodded, approving the outfit.

"Let me be clear before we go out, boy. If you as much as raise a finger without my permission, or even worse if you talk to anyone outside of this house, I'll make sure you pay for it. And by that I didn't mean a few whip strikes."

Philip swallowed hard and nodded. For the first time ever since he was brought to the mansion, he was able to leave the property. Over the last weeks, he had been given the chance to walk in the garden with Rosie, but now he could finally get out of that dreadful place for a while. Charlie had already prepared the car and was ready to go. Philip stepped into the car next to Samantha and listened as she explained him all he needed to know about the charity event. His job would be very simple, mostly he'd have to smile and take notes. That was surely the only reason why Samantha trusted him to do the job.

The car stopped in front of a big convention center. Seeing all the people walking by and into the building, Philip hesitated. Even though he hadn't been alone all the time, after three months always seeing the same half a dozen people he was nervous. Moreover, it was his first time wearing feminine clothes in a really public place. After all he had to go through, he didn't care about it as much as he would've done in normal circumstances, but it was nevertheless a big step. Walking a few steps behind Samantha, he followed her inside and waited patiently as she greeted and took pictures with a lot of guests. Being next to such a famous person meant he was virtually invisible, and he enjoyed it, given his situation. He just took the notes he had to and just pretended to be part of the furniture. After months as a maid, he was used to it.

The morning passed without too many problems. A few men were attracted by his risky outfit and gave him wolfish stares, but apart from that it was quite easy. Following the rule of not talking to anyone, he carefully avoided looking at anyway in the eyes. After a few hours of that, the meeting was over, and he followed Samantha back to the car.

"You did well," she said, smiling at him for the first time.

"Thank you, madam."

"Tell me, Peach." He noticed she'd used her female name instead of the 'boy' she'd used before. "I know about the choice my husband gave you. Why did you pick feminization?"