The Vacation

By Jennifer White

 

Tyler drained his glass, and smiled at Gianna, the bartender. She was sure easy on the eyes! She wore a tight white leather miniskirt, and a top that let her impressive boobs hang right out. In fact, it looked like a shelf there in front of her. Tyler joked to himself that she wouldn't even need a serving tray with a rack like that!

Gianna winked at him, which visibly annoyed Chloe, his wife. Now Tyler loved her, but they had been married for ten years now. And Gianna was certainly easier for him to look at right now! Not only didn't she nag him and pick fights, she just smiled, served drinks, and played with her long, jet black hair. Who cared that the mai tais tasted funny; as long as she was serving them, he'd drink there all night. If Chloe would let him.

They were in Miami, staying at the resort just off South Beach, in one of the impressive little hotels decorated in the "art deco" style of the area. It was all inclusive, so they could drink all day, hang out at the beach, eat whenever they felt like it, or whatever else they wanted. Even though there were plenty of girls sunning themselves on the beach, some of them even going topless, Tyler found that Gianna was by far the best thing to look at! And so here he was, working on his third drink.

Chloe elbowed him as he leered at Gianna's perfect behind, wrapped up in the tight little skirt. He was almost drooling over her, and Chloe was getting quite annoyed. She was really feeling the alcohol now though, so she have the energy to keep her husband in line. She just started to stare off into space, while he ogled the hot babe, and had another drink for himself.

For his part, Tyler was surprised how strong the drinks were. He was really feeling it too. It was getting hard to focus his eyes. They just stared in one direction, and he was thankful when Gianna came into view. It was too hard to even move his head anymore though, and he just stared off into space. His mind was getting foggy, and within a few minutes, he couldn't see anything. It was all a big blur.

Tyler felt so light headed! Why was everything growing dark? Why couldn't he feel anything anymore? He tried to fight it, but it was impossible; darkness overtook him, and he passed out in his chair.

 

* * *

 

When Tyler awoke, he knew right away that something was wrong. He didn't feel right at all. First of all, he hurt in several places. And he could feel the pain being dulled by some sort of drug. Everything felt strange. He opened his eyes, and wondered why he had long strands of auburn hair going over the sides of his face. That was so wrong, he decided he must be hallucinating.

He saw a halo of light, with the edges blurry still. But moment by moment, it was starting to grow clearer. He tried to move, but he was unable to. He realized that he was tied to the chair he was sitting in. He looked down to see what his situation was, when he saw something that made him scream.

There, on his chest, was a pair of huge breasts, just like Gianna's. They jutted out in front of him prominently, and he could feel their weight on his chest. There was deep cleavage between them, which he could see looking down the black tank top he had on. Now he could notice the feel of a demi-bra holding up his breasts, supporting them, shaping them.

No!!! He couldn't have breasts! That was impossible! He must be dreaming. But why did his chest hurt? And why could he feel the bra, the weight of the boobs, and the pull of the straps over his shoulders? There was no denying that he could feel it. This wasn't a dream, it had to be real. You can't feel pain in a dream. And there were many places that he hurt.

Tyler looked down further, daring to peek past his new boobs for the first time. He was wearing a white skirt, the kind in multiple layers of soft fabric, going down just below his knees. The bottom of his legs were visible. They were shaved smooth. His foot was strapped into a pair of opened toed shoes, with six inch heels. The open toes revealed that his toenails were painted hot pink.

He turned to try and get a glance at his hands, which were tied up at his side. There he saw that he somehow had long nails now, which were also painted the same hot pink color. He was also wearing several rings, and silver bracelets on his wrists.

Tyler looked back up. What else was wrong? His earlobes hurt a little. As he moved his head, he felt the long hairs that were on his head tickle him a bit. But he also felt something swinging from his ears. They felt a little cold as the brushed against his skin. They had to be long, dangling earrings. Someone had pierced his ears too.

Why had someone done all of this too him? They had made him look like a woman! Nothing else could possibly be more intimidating and sickening for a man to feel! He didn't want to be a woman! He wanted to be a man! How could they have done this to him? A rage was building up inside him, but he was in a powerless position. There was nothing he could do.

Tyler looked down again. Did his hips seem wider and his stomach seem narrower? That would explain why he hurt down there too. He also hurt in his side, but he couldn't tell what would make him hurt there. Most of all though, as the dimness subsided and he returned to full consciousness, he decided that it hurt, as if he had been kicked hard, right between the legs.

"Hello!!" he yelled, waiting to see who would respond to his call.

A few moments later, the door opened. The first person he saw was Gianna, the bartender. She was wearing a little black dress, that sparkled in the light. Even in his state, he was impressed at how attractive and sexy she was. She smiled at him, but didn't speak.

Tyler heard footsteps, and looked away from Gianna to see a man enter the room. He was dressed in a white suit, and he walked with a cane. His complexion was dark, even darker than Gianna's.

"You will call me Senor Gonzales" he said in the thick accent of a native Spanish speaker.

"What have you done to me! Why am I here!" demanded Tyler, angrily.

Senor Gonzales put a finger up to his mouth, making the "shhh" sound.

"I will answer your questions in time" he said. "But first, you must understand your position. You are mine now, and as you have no doubt discovered by now, I am turning you into a woman."

Tyler was too shocked to even speak.

"You will forget your past life, and forget that you were ever a man. Your name is Gabriella now. You have been undergoing intense mind therapy, for gender reorientation. In time, you will think as a woman."

"No..." said Tyler, his voice barely a whisper.

"Oh yes, I'm afraid so" said Senor Gonzales. "Besides your obvious implants, you need to know that you also have several devices inside you now. One of them releases female hormones into your system, at a regulated rate, along with a testosterone blocker. They will unlock the feminine potential of your cells. They will rearrange your brain, and alter your mind until you will fully believe you are female."

"Why are you doing this? You must stop!" said Tyler.

"Hush, my little Gabriella" said Senor Gonzales. "You will not speak unless spoken to. Another device has been attached to you, between your legs. Surly, you can feel its squeeze. Every time you disobey me, I press a button, and it will tighten, permanently. In time, you will be castrated. But I recommend that you obey, so that you don't have to suffer in pain. Oh yes, and when the device tightens, the same signal also triggers a massive release of estrogen into your bloodstream. The more you disobey me, the sooner you become a real woman. So I recommend that you act as a good girl."

Tyler was completely shell-shocked. He couldn't even think, he was so stunned. How could this be true? And why? Gonzales had never told him why. He looked at Gianna, the bartender. She was standing by his side, rubbing his neck.

"You like my Gianna, don't you?" he said. "In time, you'll be pretty, like her. As you look at her, you're seeing yourself, in the future."

He nodded at Gianna, who went over and untied Tyler from the chair.

"Please don't disobey him" she whispered. "I would hate to see you really suffer."

Gianna returned to Senor Gonzales, and he put his arm around her.

"Today, you will learn total obedience to me. I will test you now. You are to stand where you are, do not move, until I say you can. Do you understand me, Gabriella?"

"Yes" whispered Tyler.

"You are to say 'Yes, Senor Gonzales' when your master addresses you!" said Gianna.

"Yes, Senor Gonzales" said Tyler, his voice shaking in fear. He would do anything, as long as the man wouldn't press the button to castrate him, and release even more female hormones into his system!

"You may get her now" he said to Gianna.

She left the room, and in a moment returned holding a woman's hand. Chloe. His wife was going to see him all dressed up like a woman! Tyler blushed, as she entered the room. But instead of look of shock on her face, there was just a distant look, as if she couldn't focus on anything close by.

Chloe was led to the sofa, and sat down. Wordlessly, she sat, still staring off into space, as if she noticed nothing. Not even her husband, dressed up as a chick. She just had a vacant stare.

"What have you done to her?" whispered Tyler.

"She will show you" replied Senor Gonzales. "Gianna, go bring Miguel."

Gianna left the room, and returned not even a minute later, accompanied by a man. He was about six feet tall, well built, and very athletic looking. Gianna pointed him over to the couch. He went there, and started to take off his pants. Tyler gasped, as the man undressed.

Being her normal self, Chloe would have slapped the man and stormed off. But instead, she just sat there. When he touched her, she did something shocking to Tyler: she pulled up her skirt, revealing that she wasn't wearing any panties. Then she spread her legs wide apart for Miguel.

Tyler could only watch, as the man eagerly went to Chloe, and penetrated her. Tyler could only watch, as another man made love to his wife! He wanted to stop it, he wanted to shout out to her, but he was completely powerless. He was dressed up like a woman, with a device castrating him as he watched! And if he tried anything, the evil man in the white suit would tighten the band around his balls even more.

Tyler was filled with rage though. He had to stop it. He couldn't let it go on.

"No!" he shouted, taking a step towards the couch.

He heard the beep, as Senor Gonzales pressed a button on a device in his hand. Instantly, Tyler was filled with the most intense pain he could ever imagine, and he crumpled into a pile on the floor.

"You just brought yourself a big step closer to womanhood" said Gianna. "Once you've been castrated, you will get your surgery to become a real woman. Don't disobey him again, or you'll truly suffer."

She took out a small syringe from her purse, and plunged it into Tyler's arm. He was suddenly filled with warmth, and all the pain was gone.

"You're a woman now" said Senor Gonzales. "You are a woman. And you belong to me now. You are Gabriella. You are my obedient woman. Chloe is not your wife now; she is mine too. She is a woman, like you. You belong only to me now, Gabriella. You are mine, and it feels good for you to obey me."

The bliss of the drug was short lived, but the words that Senor Gonzales said seemed to sink directly into Tyler's mind. Obeying felt good; disobedience brought pain. His existence settled back to a dull ache, as he watched the man continue to pump his wife, then finally step back when he had climaxed.

"You may go now Miguel" said Senor Gonzales. "Tell Tito to come in next."

"Yes, Senor Gonzales" said Miguel.

Soon after he left, another man came in, has face leathery from years of work in the hot tropical sun. This man also started to strip in front of Chloe. Again, she spread her legs for him, and he was soon up inside her, pumping away blissfully.

This time, Tyler no longer felt the same rage. He just felt a sickness in the pit of his stomach. But he was too powerless to even say a word. He had to obey. He couldn't feel that pain again! Even seeing a man make love to his Chloe wasn't enough to rile him again.

When Tito was done, Gianna sent him off. Chloe continued to sit there, with her legs spread wide.

"It is your turn now" said Senor Gonzales. "She has been filled by two men, and now she needs to be cleaned between her legs. You will use your tongue, to lick her clean. I want you to suck up every single drop that my men put into her. On your knees, woman! Now!"

Tyler was so frightened of the pain, that he did as he was told. He fell to his knees, and put his mouth over his wife's pussy. He started to lick her, and to suck up the ejaculate from the two men. He hated the taste, but he did as he was told.

"Chloe, please tell Gabriella what you think of her" said Senor Gonzales.

"You're not a man anymore" said Chloe. "In fact, you never were much of a man, even before you had boobs. You were so small that you never could satisfy me. I always had to fake my orgasms with you. That's why I've been having affairs, even back when we were dating. You were never enough of a man, even back then. And now, you're just a woman."

Tyler was crushed! How could this be true? How could Chloe be telling him these awful things?

"I like you much better as a woman" she said. "I'm so glad that you're becoming female now. I can go out and find someone else for myself now. A real man. Something you never were. I like the name Gabriella. It suits you perfectly dear. You'll make a wonderful woman."

By the time that Tyler was done sucking her clean, he wanted to cry. He was so crushed! How could Chloe be like that? She hurt him worse than the pain inflicted by Senor Gonzales. He didn't even have the energy to get up from his knees now.

"Gianna, go get Paco" said Senor Gonzales.

In a few minutes, she returned with yet another man, this one young and strong.

"Tell me please Chloe" said Senor Gonzales. "How should we please Paco?"

"I think that Gabriella should do it" she replied.

Tyler wanted to cry out 'No', but the device in the man's hand made him bite his tongue.

"Very good, my dear. As you wish. Paco, come here and let Gabriella have a turn."

Paco unzipped his fly, and let out his manhood.

"All right Gabriella. You know what to do. You've already tasted what it is like. Now it is your turn to please a man" said Senor Gonzales.

Tyler did cry now, as he opened his mouth, and let the young man put himself inside. What he was doing now was so low and degrading! He felt the young man get harder and harder in his mouth, until he reached the back of Tyler's throat. It didn't take much to feel the sudden hot spurt from him, and feel the throbbing in his mouth.

Paco zipped himself up, and left the room, as Tyler was still on his knees.

"Now you are a woman" said Gianna.

"Don't worry dear" said Chloe. "Its all right. Girls do that to their guys all the time. Now that you're a girl, you'll be doing that all the time when you go out on dates."

"That's right" said Gianna. "You'll be dating men now. And you'll be so easy; you'll always please them."

"You are Gabriella now."

"You are a woman."

"You have boobs. You'll soon have a pussy."

"You're a woman."

"You are Gabriella."

"You've had sex with a man. You are a woman."

"You were never a man."

"You are Gabriella now."

"You're one of us now."

"You're a woman. You're a girl."

"You're a chick. You're a babe."

"You are female. You are Gabriella."

"You are a woman."

"You have always been a woman."

"You have always been a woman."

"You have always been a woman."

 

Tyler was completely crushed. Chloe and Gianna kept repeating things to him, hitting the trigger phrases from his mind therapy sessions he had undergone while he was still unconscious. With each repetition, Tyler become more and more confused, as he had a harder time distinguishing his previous reality from his new existence.

As the reprogramming of his mind started to kick in fully, he suddenly lit up with smile. The girls were right; he had always been a woman. Wait, not he, but she. She had always been a woman! She was Gabriella. She was a woman, and she always had been, for all her life! It was so clear now.

She wasn't a miserable man; she was a happy woman! Of course! She felt so proud of her big boobs! She loved her hips and her curves. She stood up, and straightened her skirt. She licked her lips, tasting the bit that Paco had left on her.

"Can I borrow your lipstick?" she asked Gianna. "I seem to have forgotten my purse."

"Sure, honey" said Gianna, handing over the tube.

Gabriella put it on her lips, then smiled as she handed it back.

"Hello Gabriella" said Senor Gonzales.

"Hello Senor Gonzales!" she replied, curtseying to him.

"Gabriella, I have decided that you will work here in my hotel now, as a maid. You will wear a pretty black uniform with lots of white lace, and you will show off those gorgeous legs of yours, and your pretty chest, for all the guests."

Gabriella nodded. She was so happy that her master was letting her work!

"At night, you will pleasure our male guests, and you will work as a cocktail waitress, helping Gianna."

"Yes Master" she replied.

"After your last operation, when you have a vagina of your own, you'll be able to lay the men however they prefer. Doesn't that excite you?"

"Yes Master!!!" said Gabriella. "I can hardly wait. I wish you'd get me the operation today!"

Senor Gonzales handed his remote control device to Chloe.

"Press this button twice, when I tell you" he said. "It will tighten up, until Gabriella is completely castrated. Then we can give her what she wants, and let her have the operation."

Chloe smiled, and took the device from him.

"Gabriella, you will also work as a call-girl" he continued. "You will date gentlemen who pay me money. They will take you out to fancy nightclubs, and you will please them too."

"Sounds like fun!" said Gabriella.

"All right my dear Chloe" he said as he smiled. "Press the button twice, and take away the last vestige of Gabriella's manhood."

"Gladly" she said, as she pressed it twice. "This will only hurt a bit."

As Gabriella passed out from the pain, she smiled. It was worth it. She was becoming a real woman now.

  

  

  

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