The Hacker

"I... I don't know." In truth, he didn't know what she wanted to hear and preferred to be quiet rather than saying something wrong.

"If you'd agreed to the blowjob, it would've been a matter of five minutes and you'd be over with it. Instead, you choose something that would last for the rest of your life."

"I don't know. I guess it felt wrong."

Samantha smiled. "You're a person of principles. I like that."

When they were home, he started to go back to his room to change into his maid outfit, but the woman stopped him. "Go to my office and wait for me."

He did as he was told. Not knowing if he was allowed to sit, he remained on his feet. Fortunately, Samantha arrived after a few minutes. She'd taken off the dress and the heels and was wearing a casual outfit with jeans and a sweater.

"Tell me, Peach, do you find me attractive?"

Philips froze for a few seconds, but then decided to just tell her the truth. "I think you're very beautiful, madam."

Samantha smiled. "I want to offer you the same choice my husband gave you. Do you prefer to pleasure me orally, or more feminization?"

He hadn't seen this coming, and he didn't know what to do. He realized the problem of his situation. If he agreed to pleasure Samantha and she told her husband, Rob might've got angry and punished him. On the other hand, choosing feminization again would probably mean giving up any change of going back to being a boy. Still, the memory of his week in the basement cell was vivid in his mind. He couldn't risk it again.

"I choose feminization."

Samantha laughed. "You know, I receive thousands of messages from people who would give anything just to kiss me. You have the chance to join me in bed, and instead you prefer to be my husband's dolly. The world's a strange place."

Philip thought that kidnapping people and torturing them was much stranger than that, but of course he didn't say anything. Samantha dismissed him, and then probably called Rob, because in the evening he was summoned by him.

"My wife told me what happened today," said the man with a broad smile. It was obvious how much he was enjoying this. "I mean, I understand why you wouldn't want to suck my dick, but Samantha? Seriously? Are you asexual?"

Philip didn't know what to say. The man actually had a point.

"Anyway, you made your choice. I called a friend who owns a private clinic and he agreed to help us speed up the paperwork. Tomorrow you'll sign the necessary forms, and in two weeks you can have your breast implants."

"My... breast?"

"Well, you're the one who preferred feminization over licking my wife's pussy. The estrogens are working on you, but you won't get a real breast unless you get an implant."

"But I thought... I didn't think..."

"It's too late for that. You'll get a new breast, end of the story."

Philip cried for most of the night, and he barely slept. Rosie tried to console him, but he felt like his life would be over forever. There was no way he could go back to anything similar to how it was before. Although he was in captivity, over the last weeks his masters had allowed him to contact some of his family and friends to prevent them from calling the police. He was reclusive enough even before, so they weren't that surprised that he hadn't called them for a month. He wondered how his parents would react if they saw him in his maid outfit.

As announced, the following day he signed the forms. In order to avoid scandal in front of the lawyer and the doctor that had arrived for that, he had been allowed to wear a little black dress instead of his housekeeping uniform. His hand trembled as he signed. Rob was glowing. His little feminization project was going even better than he'd ever hoped for. In less than four months, his victim would already look more like a woman than a man. Philip, who didn't know what to think anymore, thought that had to be some kind of a world record. He buried himself in his work to avoid obsessing about it and waited anxiously for the surgery date.

Two weeks later, he was allowed back into the little black dress, and he left the mansion for the second time after his kidnapping. Charlie was driving, and Rob was sitting next to him. He didn't want to lose even a second of that day, so he'd cleared of all his appointments. When they arrived at the clinic, which was in a wonderful mansion in the middle of a wood, a team of doctors and nurses took care of him. He was stripped and dressed in a hospital gown, and then led to the surgery room. When they put him to sleep, there were tears in his eyes.

The following couple of days was just a blur in his mind. It was a mix of the anesthetic, the painkillers, and the shock of this whole situation. When he was lucid enough, however, he saw the two large tits on his chest. Well, they weren't huge, but they would still be impossible to hide. From now on, dressing and posing as a woman would be his only choice. He didn't know what it was worse: the physical pain, the humiliation, or the terrifying realization that this operation was definitely not the last torture Rob had in mind for him.

When he finally got back to the mansion, he noticed than his clothes had been swapped. His new bras were larger to support his new breast, and his maid uniforms had become skimpier, mostly to show off his cleavage. It was only a small humiliation after all that he'd went through, but it was enough to make him cry off in frustration. He realized it'd only been two months since the real beginning of his three years of contract as a maid. How would he look in the end?

"I think they must be bigger than mine," was Samantha's only comment as they ate breakfast the following morning. Even if she'd stopped despising Philip as she'd done at the beginning, she kept ignoring him most of the time.

"It's your own doing," said Rob smiling. "I had planned to wait a few months before doing that. But I'm not complaining."

Philip couldn't help but looking at Samantha with rage. Those big uncomfortable things on his breast were her fault. Luckily for him, neither she nor Rob noticed that, or he would've ended up in the basement in the blink of an eye. Instead, he retired and went on with the housework. Another bad aspect of his new tits was Charlie's and Khaled's attention. They wouldn't stop leaving him alone, and the driver even groped him a few times.

"Just let them," said Meng in one of the rare moments when she felt like talking. "I complained about it once, and the masters punished me instead."

At least, Rob mostly left him in peace for the following month. As the housekeeping routine became fully instinctive to him, he noticed a few changes. First, the estrogens kept shaping his body, slowly but constantly. Second, he barely noticed the corset and the heels anymore. It was true that a human body can get used to almost everything. Moreover, his hair was growing longer, and he was getting very skilled at doing his make-up. Unfortunately, the day came when Rob finally asked him the question he knew would come in the end.

"It is time, Peach. Blowjob or feminization?"

Something strange happened in Philip's mind. He didn't have anything to lose anymore, since the breast implants had already put an end to any attempt to look like a boy. On the other hand, his refusal to have sex with his masters was the last thing he had left.

"Feminization, sir," he said.

Two weeks later, he left for the clinic again. This time, he would undergo a facial feminization surgery. It was more difficult than getting a breast implant and he had to spend the rest of the month in his hospital bad. When they finally removed the bandages, a pretty girl was looking back at him from the mirror. His chin was slimmer, his cheekbones higher, and his nose thinner. That was undoubtedly the face of a young woman. Besides, his hair now came down to his shoulders, and the estrogens had helped with the rest.

"It'll be Christmas soon, and you're expected to visit your parents," announced Rob a few weeks later, after summoning him to his office. "They'll grow suspicious if you don't. So, I think you should attend your family dinner."

Philips went pale. "But... how can I hide... all of this?" And he gestured at his new body, who was hardly similar to his old one.

"Don't be ridiculous, of course you can't go as a boy. You'll have to tell them you're transitioning. We'll come up with a story and Charlie will pose as your boyfriend."

He didn't even know what was worse. If exposing himself to his family or having to pretend Charlie was his boyfriend. "Please, sir, don't make me do this!"

"I don't care what you want. You'll do what I say. And if you try to say even a single word about us to anyone, I'll make sure your own family pays for it. Do you understand?"

Philip swallowed hard and nodded. He felt scared and beaten.

"Don't worry, we'll find a proper dress for you."

And indeed, they found it. On Christmas morning, Rosie and Meng combined their efforts to help him get ready. He suspected they were envious, since he was allowed to go out and meet his family, while they'd have to stay in the mansion. Anyway, he would've been happy to exchange place with them and spend the day cleaning and ironing.

His outfit consisted of a sleeveless red corset dress with a very tight bodice and a pleated miniskirt that came down to his mid-thighs. It had a deep cleavage and was meant to be worn without a bra, so his round breast was mostly on full sight. His underwear was reduced to a pair of red lace panties that barely covered his privates, small as they were after half a year of hormones, and a pair of sheer nylon stockings. They were a particularly expensive piece of hosiery and had broad lace tops that could hardly be covered by such a short dress. Finally, he wore a pair of shiny black stilettos with platform heels and red soles.

"I look like a hooker," he commented dryly.

Rosie cocked her head as she looked at him. She wanted to tell him not to worry, but she didn't want to lie. He did look like a prostitute in that outfit. Even a biological woman like herself would've refused to wear such a dress to a family dinner. That was also Charlie's reaction as he saw him, at least judging by the light in his eyes and the bulge in his pants. He looked good in his formal suit and tie, but Philip hated him now more than ever.

"Mr. Paulson told me I could choose your new name for today", he said while they were driving to his parents' house. "You can't use your old male name, of course, but we can't call you Peach either. So, I decided I'll call you Kathleen. There was a girl named Kathleen in my high school and I liked her very much."

Philip didn't say anything. As much as he hated all of that, at least Kathleen was a normal name. He wandered if he could convince his masters to call him like that instead of 'Peach'. The trip to his family's place was quite long, so they had to stop for a pause after a couple of hours. Luckily for him, he was wearing a black coat that covered his dress and guaranteed some modesty, but his ridiculously high heels didn't go unnoticed. He received a lot of hungry stares and even a couple whistles as he hurried to the women's bathroom.

When they finally stopped in front of his parents' house, he couldn't find the strength to get out of the car. Charlie had to drag him out and push him, terrified as he was, to the door. Desperate as he'd never been even in the last weeks, Philip fixed the hem of his coat, trying to look as modest as he could, and he almost stumbled on the high heels. When his mother opened the door, she just looked at them with a polite smile. She hadn't recognized him.

"How can I help you?" she asked. She was a good-looking woman in her fifties with grey hair and a round face. She was wearing a dark green dress with patterned tights.

Philip opened his mouth to speak, but the words didn't came. He looked at Charlie with desperation on his face, and the driver took over the situation.

"Hello, Mrs. Landon, nice to meet you. My name's Charlie and this is my girlfriend Kathleen. She needs to tell you something."

Philip cleared his throat. There wasn't really a way to avoid the shock. However, as he started to speak, his mother's face changed expression. She came closer to him and studied his face.

"Is... is that you?" she asked, full of disbelief.

The boy nodded. "Yes, mom, it's me."

"Oh my God! What did you do, Philip?"

"I... I'll tell you everything, but please call me Kathleen. Please, let us come inside."

The woman looked at him for a few seconds, still trying to realize if all of this what real, then she looked at Charlie, who was just smiling as if nothing were going on. Finally, she moved aside and let them come inside. Luckily, it was still early enough and only his father was inside. Just as his mother, he didn't recognize him at first, and almost had a heart attack when he she told him who it was. Five minutes later, they all sat in the living room with glasses of water in their hands. Of course, Philip's skimpy dress didn't help. Without the protection of the coat, he felt exposed and kept pulling his skirt and shifting his crossed legs to cover his body a little more.

"I'm really sorry you had to find out it this way," he said, and he meant it. The rest of the speech, however, would be the lie Rob had prepared for him. "Over the last year I've come to understand that I feel like a woman, and that I had to make a big change in my life. As you can see, I've started transitioning, and I've also had a few surgeries."

His parents just stared blankly at him, so he carried on.

"This is Charlie, we've been together for a while now. He's been very supportive with my transition, and I really wanted you to meet him."

Just another information they weren't prepared to receive. Their son was now a girl, and he was also gay and dating a man. He couldn't blame them for being shocked.

"Kathleen told you were a very liberal couple, and you'd understand," said Charlie, who was sadist enough to enjoy all of that.

"If this makes you happy..." said his mother, but she didn't look convinced.

"I had no clue," said his father instead.

"It's been a sudden realization, but I assure you this is indeed what makes me happy."

"Well, nice dress," said his mother with a forced smile.

"What are we going to say to the rest of the family?" asked his father.

The woman shrugged. She had no idea.

"I knew it wouldn't be easy for any of you," said Philip. "But I still believe that it's right to show my new identity to the whole family. We can do it."

In truth, the rest of the day was a nightmare. Over the following hour, the rest of his relatives arrived. There were his aunts and uncles, his many cousins, all of their girlfriends and boyfriends, and even a few family friends. Altogether, more than twenty people who saw him wearing lipstick, a slutty dress, and a pair of hooker heels. The only positive aspect was that the shock was big enough that nobody found the time to make any real comments about the situation. The lunch was mainly a series of forced smiles, pleasantries, and set phrases. It was 4 PM when they finally managed to get away. His parents had begun to digest the news by then and they made him promise to visit them again soon. They weren't happy, but he was still their child.

As soon as he got to the car, he collapsed on the seat and cried out his eyes for the whole trip back to the mansion. He felt devastated and would've happily picked a whipping over another experience like that one. His hatred for his kidnappers was growing even deeper than before. Actually, he was so lost in those thoughts that he hadn't noticed they weren't on the highway anymore. Charlie had took a side road and was stopping the car in an empty field. The place was secluded and surrounded by empty warehouses. It didn't look very reassuring.

"Why are we stopping here?" Asked Philip with a worried look on his face.

Charlie turned to him and looked at him with a devious smile. "Did you really think I'd agree to do all of this for you without anything in return? I've been staring at those nylon legs of yours for the whole day and I can't take it anymore. I think it's time you do something for your 'boyfriend', my sweet little Kathleen."

Philip's heart started beating faster and he tried to get out of the car, but the door was locked, and he had no change to overpower Charlie. The driver was tall and heavy, while he was weak as a real girl after half a year of strict diet and testosterone blockers. Charlie grabbed him tight and pulled him to his side, opening his door and dragging the poor boy out. He pushed him down on the tarmac, facing down. As he held him sill with an arm, he used the other hand to lift his dress and strip tear up his panties. Then he lowered his pants and penetrated him with a single push.

Philip's scream was unhuman, almost beastly. The pain was terrible, but the surprise of the attack was at least as much terrifying and that. Charlie grunted and kept pushing in and out. The boy's asshole was virgin and was very tight. There was hardly enough space for the driver's huge erection. Philip screamed again, and then begged, and then cried, and finally laid still like a corpse, just waiting for the torture to end. Charlie came after a full ten minutes, erupting inside the boy. Then his cleaned himself with a tissue and pulled his pants back on as if nothing had happened.

"Climb inside, Kathleen. We don't want to be late."

Philip looked at him in disbelief. He couldn't control his instincts and tried to run away. He was wearing five-inch platform heels, though, and he barely crossed a third of the field before Charlie was again on him. The driver slapped him into submission, then opened the trunk, took a piece of rope and tied both of his wrists and ankles. Finally, he lifted Philip up and placed him into the trunk, leaving him locked in that small, dark space. Too scared to do anything, the boy laid still, barely noticing the movement of the car. He wanted to die.

When Rosie and Meng saw him, they went pale. Charlie dropped him on the floor of the servants' quarter without even untying him. Luckily for him, both girls hurried up to help him and cut him loose. They asked him what had happened, but he didn't have the strength to answer. So, they helped him get out of his clothes and to the bathroom. His face was red because of the slaps, his legs and body were full of bruises, and he was losing blood from his hole. They cleaned him up with delicate hands and then helped him into a fresh pair of panties and one of his silky baby-doll nighties. He laid down on his bed, his eyes still wide with horror.

"Please, don't leave me alone," he begged.

"I'll stay with her," said Rosie to Meng. "You can go."

The maid gave a worried look at Philip, but then nodded and left the room. The nurse took the boy's hand and sat down next to him. They didn't talk, and she waited until he finally fell asleep.

"What the hell happened to you?" asked Rob when he saw him at breakfast.

Samantha gave Philip a worried look. Meng and Rosie had done everything possible to hide his condition, but nothing could really do that. His face had healed over the night and his bruises were mostly hidden under his dress and nylons, but his shocked expression, terrified eyes, and constantly trembling hands and legs were still obvious. She got up and came closer to him. At that distance, all the injuries were visible.

"Call Rosie," he said to his husband.

Two hours later, Charlie was locked in the basement. Rob had even asked Philip if he wanted to watch, but he had no intention of seeing him ever again. He got a free day and closed himself in his room, trying to sleep a little more. Rob's reaction had surprised him, but after a while he understood what it was. It wasn't the rape and the violence that bothered him, but rather the fact that Charlie had done so without his permission. He also suspected that Rob had really wanted to be the first one to have sex with him. Anyway, Charlie disappeared that day. He didn't know what they'd done to him, and he never cared to ask. Even the slightest male touch made him now jump on his feet, but he had to endure it. If only, after the rape Rob's sexual interested in the boy had only grown.