Flying High Again

by Jennifer White

 

Walter was thinking happy thoughts as he rode out to the airport. He'd be on a trip for a whole week, and finally he'd have some privacy. When he was with his wife, he could never dress up. She wasn't into that, and he had to keep all his bras, panties, skirts and blouses hidden from her. In a secret place in the attic, he kept women's shoes, makeup, a purse, and everything he needed to transform himself.

When he went on his monthly week-long trips out of town on business, it was his only opportunity. He'd bring his suitcase full of suits, ties and dress shirts to wear during the day. But in his carry-on, he'd have his secret stash. When he got to the hotel, he'd have his fun, 'being' a woman.

 

Traffic was light, and he arrived in plenty of time for his flight. He stood in the line, and checked his bag through to Chicago, his ultimate destination. Then he strolled over to the long slow line for security. Walter always arrived extra-early, so there would not be any problem rushing at the last moment. Today was no exception: he had almost a full hour before his flight was scheduled to board.

As usual, the line moved slowly, but he was prepared for this as well, reading the newspaper as he moved forward bit by bit. Before too long, Walter was at the front of the line. He put his bags on the conveyor, took off his shoes and his watch, putting them into a tray along with his wallet and keys. He waited until they signaled him, then he walked through the metal detector.

Walter put his shoes back on, his watch, and put his wallet into his pocket. He was about to collect his bags, when a female security guard walked over to him.

"Excuse me sir, is this your bag?" she asked him.

"Why yes it is" he replied.

"Come with me sir" she said gruffly, in a clipped military manner.

In all his years of traveling, Walter had never had something like this happen! He decided it must have something to do with all of the extra security these days. He follow the attractive woman into a small private room off to the side. She was well built, and looked like she didn't have an ounce of fat on her anywhere. She wore her hair up in a tight bun, and she only had on minimal makeup.

The security uniform with the deep blue knee length skirt and the tight top which couldn't hide the generous bosom underneath it, served to make her look particularly attractive. He stared at her, as she stared at him. The tight corners of her lips started to turn up, with just a hint of a smile. At first, Walter thought this was encouraging, that she liked him. But very soon, he came to realize that the smile meant something else. It meant she was enjoying what she was about to do.

"Open up the bag sir" she said, pointing to his bag with his clothes. His *female* clothes. Walter swallowed hard. This was going to be very embarrassing. He unzipped the bag, and began to empty it out.

"Ah, these are my wife's" he said. "She's going to join me in Chicago."

"That's funny, I don't see a reservation for her anywhere in the system" said the woman. "And tell me, why would your wife need fake boobs? And panties with padding for the hips and butt? These aren't for a woman, are they sir. They are for *you*."

The words shot through Walter like a knife. For *you*. He was caught. After all his years of being discrete, he had been discovered. He blushed bright red.

"You're not a regular businessman, are you?" said the woman. "In fact, you're not really a man at all. You're a *sissy*. A sissy who likes to dress up as a woman. Isn't that true?"

Walter stood there mute, not knowing what to do or say.

"I asked you a question sissy!" barked the woman. "If you don't cooperate fully with me, I can have you locked up, for security reasons. You'll spend the next ten years in prison. Now answer me!"

"Yes" said Walter reluctantly.

"Yes what?" asked the woman.

"I'm not a man. I'm a sissy who likes to dress up as a woman."

"Very good sissy. Now tell me, when you have your pretty clothes on, what name do you go by?"

"Wendy" he said.

"Wendy? That is a very pretty name for a sissy. All right Wendy. Now that you've been discovered, your only hope is to obey me in all things. If you don't do exactly as I say, well, then...."

"What do you want me to do?" said Walter, shaken and upset at the turn of events.

"Dress up for me sissy. Show me what you look like, when you're Wendy."

"What?"

"You heard me. Makeup and everything. Now do it! Go!"

Walter was trembling. He had never been ordered by a woman like this, and he had to admit, it really turned him on. And this was the first time a woman had *wanted* for him to get dressed up as a girl. Plus, she had him over a barrel, and he had to obey her. So he took off his business suit, and then his T-shirt.

"Go ahead, take off your boxers. It won't be anything I haven't seen before" said the woman.

Walter took them off too, and she let off a laugh.

"You really *aren't* a man, are you? Not very much of one, at least. I haven't seen a grown man that small ever in my life. You're just microscopic, aren't you? No wonder you want to dress up as a woman. You're practically one already, sissy."

Walter had never thought he was *that* small. But this woman's words shot through him, making him feel like he was nothing. He felt so powerless with her! She controlled everything, and all he could do was to follow her orders. He had never felt so weak in all his life.

 

Walter put on his padded panties. Then his dark nylons, his bra, and of course his breastforms. Then he put on a black skirt, and a silky white blouse with frilly cuffs and lace trim. He pulled the hair extension out of the suitcase, and attached it so that it looked like he had a ponytail.

"Now your makeup, sissy" said the woman.

Walter reluctantly pulled out his makeup kit, and went to work. With the practiced touch that only years of experience could give, he brought out the beauty of his best features, and hid the rest. He did a very good job in fact, accentuating the eyes, and making his lips look luscious and kissable.

"Very pretty, sissy" said the woman. "You must not be a man at all. What kind of man looks so good as a woman? I bet that you want to go out like that, in public, so you can find a man for yourself. What kind of woman would you be if you weren't attracted to men? Yes, I'm sure of it, sissy. You like to dress up, so that you can find men to date. Isn't that true. Tell me."

"No!" protested Walter. "I dress up, but I would never want to be with a man."

"Now Wendy, my pretty little sissy" said the woman, "I have here in my desk a bag of drugs, which I confiscated from another traveler today. If you are not cooperative with me, I'll say I found them on *you*. And you'll end up in jail. Do you want to go to jail, sissy?"

"No!" said Walter.

"Then lets try this again. Tell me that you like to dress up as a woman, so that you can date men."

"I...I dress up like a woman" said Walter, "...so that I, can, um, you know, uh...date men."

"Again. Make it sound like you believe it" said the woman.

"I like to dress up as a woman, so that I can date men" said Walter, more firmly this time.

"See? I knew it. You sissies are all alike. You play your little games, pretending that you just like to dress up, but I *know* that you prefer men."

"Why are you doing this to me?" said Walter, who was feeling even more helpless now.

"I've done nothing" said the woman. "You've done this all to yourself, dear. You are the one who has turned yourself into a woman. Of course, when you don't even have a prick, that makes you a woman already, doesn't it? Now tell me again that you're a sissy, and that you *want* a man."

"I'm a sissy" said Walter, in utter humiliation and embarrassment. "And I want a man."

"Good sissy. Good girl" said the woman. "Today is your lucky day. I'm going to help you out."

"How are you going to do that?" said Walter, full of doubts as to her intentions.

"It is very simple. You have 20 minutes now until your flight takes off. I will help you pack your bag, and escort you to the gate."

"But I don't have time to undress and take off my makeup" protested Walter.

"Who said anything about undressing?" said the woman. "And you'd certainly look silly dressed like that, if you don't keep your makeup on."

"You mean I'm supposed to go out in public like this?" gasped Walter.

"How else are you going to find yourself a man?" said the woman. "No man will ever find you if you only dress up like that in your hotel room. No my dear sissy girl, you *are* going to fly to Chicago dressed like that. And you will check into your hotel like that. And you will attend your meetings wearing pretty clothes, just as you are now. You will go to dinner, and go to the bar. And you will find yourself the man that you so greatly desire in that feminine heart of yours."

"I can't go to my meetings like this!" said Walter. "Besides, once I get there, you wouldn't even know what I do."

"Yes I will" said the woman. "You will send me an hourly picture with your camera phone. And I will be able to check up on you. Otherwise, when you come to the airport to fly home, they'll be waiting for you there, to arrest you. I'm sure a sissy like you will do well in a federal penitentiary."

"No! Please don't do that!" said Walter.

"Then its settled. You will dress up, and stay that way for the duration of your trip. Now lets get going! Your flight will leave very soon."

The woman led Walter out to the public area of the airport, and he immediately blushed. All of the hundreds and hundreds of people coming and going could all see him, wearing women's clothes. He was fully dressed, and he was in public.

The woman had him sit on the back of an electric cart, and she drove to the gate. Everyone turned to look at the cart, with its loud beeping noise. And they all saw Walter riding on the back, dressed up like a woman.

 

When they at last reached the gate, the security woman led Walter by the hand to the gate attendant, who was about to close the door.

"I'm sorry" said the security guard, "but we had a little bit of a hang-up with her luggage. But it is all set now. Can you please show her to her seat?"

"Certainly" said the gate attendant with a smile on her face. She looked at Walter, and suppressed a giggle.

"Don't forget what I told you" said the security woman, as Walter walked down the jetway, his skirt swishing against his legs. "And don't forget about the photos! I look forward to seeing them!"

 

Walter sat in his seat on the plane in first class, and he just couldn't get comfortable. How could he be there in public, dressed up as a woman, with everybody able to see him? The flight attendant came over to him with the beverage cart.

"Can I offer you a drink Ma'am?" she said.

Nobody had ever called him Ma'am before, and it sent a shiver up and down his spine.

"White wine" he said, trying to use as soft of a voice as possible. "Make it two. I really need a drink."

"Sure thing Ma'am. It's a long flight though, so you can have plenty once we take off."

Walter gulped down almost half of his wine at once, then set the glass down. The seat next to him was occupied. It was a man of about his age.

"Wow, you sure can put away the wine" he said. "I don't see many chicks who can do that!"

"Um, its an old trick I learned in college" said Walter.

"Ah, a sorority girl" said the man. "I'll need to hang out with you. Sorority chicks always know how to party."

Walter could smell the alcohol on the guy's breath. He was obviously blasted. His vision must have been blurry, if he was hitting on Walter! Walter couldn't stand it. Being hit on by a man. He wished he was sitting next to the beautiful blonde in the next row, or even the older lady across the aisle. He wanted to be anywhere but where he was. This was going to make for a long uncomfortable flight.

 

* * *

 

Three hours and five drinks later, Walter had loosened up considerably. By now, he was getting more and more used to the stares from everyone, seeing him as a man dressed up as a woman. And with all the alcohol in his system, he was starting to not care.

He loosened up so much that he was having a fun time chatting with the guy next to him. When the plane was finally coming in for landing, the guy expressed his interest in Walter.

"So Wendy" he said, "I'll be in town all week too. And we're both staying downtown. Why don't we hook up dinner tomorrow? Say, eight O'clock, at the chop house? I'm buying."

"Okay Bert, that sounds nice" said Walter, who loved the food there at the Chicago chop house.

It was only as he was walking down the jetway that he realized what had just happened: he had made a date with a man! Walter shuddered. None of this was supposed to happen! And now he was trapped like this, dressed as a woman. He was going to have to attend his meetings like that too. The first thing that crossed his mind, was that his outfit was *not* appropriate business dress.

So as soon as he reached his hotel, he headed out to Michigan Avenue. There were all sorts of stores up and down the street, with every kind of clothes you could imagine. Walter bought himself two women's suits. One gray with a knee length skirt, and one pantsuit. He also bought shoes that would be more comfortable to walk in, than the heels he had packed.

Also, he wouldn't have enough makeup to get through the week, so he needed to restock on that. And he didn't have a nice purse. Suddenly, he was having fun shopping as a woman. With every moment that passed, he felt more and more comfortable being out in public like that. And now that it was night, he didn't even get a lot of strange looks.

He went into a smoky bar to listen to blues music, and hide in the dim light in the corner. All night long, men offered to buy him drinks, and came over to flirt. He brushed them off, and told them that he was dating someone already. It was only a half-lie. He did have a date the next night, with Bert.

 

* * *

 

The next day was terrible for Walter. There were over five thousand people from his company, who were attending the meetings. They all crowded into a large room in the convention center. Everyone wanted to introduce themselves, and asked who he was.

"I'm Wendy" he would say. "I'm new, in the west coast organization."

If they asked for details, he'd say he just started, and he didn't know the names of anyone yet who he worked with. He tried to keep a low profile, but there certainly seemed to be a lot of men who took an interest in him, and wanted to talk to him. He took to hiding out in a stall in the lady's room during coffee breaks, so he'd be less in the open for people to question.

 

Somehow he got through the day. He trudged back to his hotel, his feet sore from wearing a pair of new shoes in a size a little too small for him. He got to his room, took his picture wish his phone, and sent it to the security woman. Immediately, she called him back.

"So Wendy, how was your first full day as a woman?"

"I don't like this" said Walter. "I've been hit on by men. I have a date tonight, with the guy from the airplane. I don't think I can go through with this."

"A date? That's wonderful! What a good sissy you are. Only a few hours as a girl, and already you've used your feminine charm to snag a guy! I'm am so proud of you! Way to go, girl!"

"Um, thanks" said Walter glumly.

"Your goal for tonight" she continued, "is to get him to kiss you. And to get a second date.

 

Walter couldn't believe that he was out on a date with a guy. It was impossible. And he was going out, dressed up as a woman. Even more impossible. But it was true. This wasn't imagined. This wasn't a fantasy. This was reality.

The thing was, this was not at all what he wanted. Although he loved to dress up as a woman, there was no way he wanted to *be* a woman. There was no way he wanted to be with a man. And so, although he went out on the date, when the end of the night came, he wasn't able to go through with the final instruction, to have a good night kiss. He just could not conceive of actually doing it.

But that led to a slight problem. When *she* called the next day, the woman from security, she seemed to already know that he had chickened out.

"Look in your luggage, on the inside zipper pocket" she said.

Walter didn't pack anything there. Why should there be something there now. He unzipped it, and looked inside. There was a plastic baggie, with dozens of little white pills.

"What's this?" he said.

"Those are female hormones" she said. "Estrogen and other related hormones. You will take two of the pills now, so that your body can have its first taste of real femininity. Your cells are thirsty for estrogen, so their feminine potential can be unlocked. You'll grow real boobs. Your skin will get soft. You'll get curves. In short, your *real* transformation into a woman will begin. Now."

"No! Don't ask me do this!" said Walter.

"I didn't *ask* you to do it sissy. I *ordered* you to do it. Do you really want to find out the consequences if you don't obey me? Now quit your whining, you sound like a little girl. Just do it, now! Take your pills, and start to feminize yourself for *real*."

Walter took out two of the pills, and with a trembling hand, he put them in his mouth and washed them down with a glass of water.

"There" said the woman. "That wasn't so bad, was it?"

"I don't feel anything" he said.

"It takes some time to act on you. Did I mention that if you stay on it long enough, even your inner desires will change? Before long enough, you'll be *wanting* men, and I won't even have to encourage you. You'll do it on your own."

Walter was almost shaking now. This was getting worse and worse, out of control.

"Why are you doing this to me? Why won't you stop?" he whispered.

"Isn't it obvious? I'm doing this to you, so that I can turn you into a woman. And I won't stop, because you aren't one yet. It's all very simple."

"I can't go through with this anymore!" yelled Walter. "It has to stop!"

"It can Wendy. All you have to do is walk down to the clinic, and sign up for your gender reassignment surgery. Once you're female, I'll be done with you."

She hung up, leaving Walter feeling sick to his stomach.

 

He made it through another day of meetings dressed as a woman, but now he was getting really tired of this game. It had to end. He just didn't know how to make that happen. He was back in his room, trying to think of what in the world he could do, when he suddenly heard a knock on his door. He ran, and looked through the peephole. There, he saw *him*. Bert. His date. Somehow, he had tracked him down!

 

"Listen" said Bert, as a surprised and stunned Walter let him into the room, "we have to talk. I know who you are. I know *what* you are. You don't have to be so shy around me."

"What do you mean?" said Walter, unsure of himself.

"I mean that I know that you're a pre-op transsexual. I know that you're really a man, that you're on estrogen, and that you're going to become a woman."

"But...." started Walter.

"Shh, my love" said Bert. "I want you to know that there is *nothing* that turns me on more, than to know that you are someone who loves me so much, that you're going to become a woman for me. I'll be the first one to explore your new pussy. I'll be the first to suck on your new large boobs. You are my fantasy, darling. And will stop at nothing, until you are mine."

"You don't understand!" said Walter.

"But my dear, I do" replied Bert. "I am going to make you *my* woman. I am going to make you my wife. You will spend the rest of your life with me. You won't have to work. You can be a housewife, just as you've always imagined yourself. You'll spend your days doing girlish things, shopping, cooking, cleaning, hanging around with the other women in the area. You can buy yourself all the pretty clothes and things you want. That will be your life my dear. You are mine now, and you will be with me, forever."

Walter didn't know what to say. On the one hand, it was his ultimate fantasy. Live his life as a woman, with all of the clothes and things he could ever want. But he didn't want to be some man's wife! He didn't want to have the operation, and become a woman for real!

Walter's hand was trembling. Bert stood up, and walked over to him, taking his hand. Bert seemed so self-assured, so strong. Not like him. He was weak. He *was* a sissy. His emotions were all over the place, and he was unable to speak.

But now came an even bigger shock. Bert was still holding his hand. With the other hand, Bert pulled out a ring. A ring with a huge diamond. How it sparkled in the light!

"Wear this ring, and become my fiancee" said Bert. "You'll be my wife one day Wendy. With this ring, you pledge yourself to me, and to no other man."

Walter was too shocked to even react, as Bert slipped the ring on his finger.

"Now you are mine" he said. "I am your man, and you are my woman. Now, and forever."

He leaned forward to kiss, and Walter felt too powerless to stop him. He sort of melted into his arms, and let himself be kissed. He was becoming a woman now, Bert's woman. He'd be operated on, and turned into a *real* woman. He was going to become married. He was going to become Bert's wife.

"Those weren't estrogens you took this morning" said Bert, sending a total shock through Walter's mind.

"How do you know..."

"She told me. She controls everything, doesn't she? I used to prefer real women, until she got ahold of me, and retrained me. Now I want *you*, my dear."

"No..." whispered Walter.

"Oh yes. Now back to what you took. It is a very special drug, which makes you become very complaint, and very easy to manipulate and reprogram. Your defenses are down Wendy. You can't control yourself. You *will* do as I tell you, and you cannot disobey. Now tell me that you're my woman!"

"I'm your woman" said Walter, much to his surprise. Walter seemed so strong, how could he say no?

"You *are* my woman now, and forever. You are Wendy now. There is no more Walter. You are a woman now. There is no man. And you are *mine*."

"I am your woman" said Walter.

"Your only desire, is to please me. That is your life. You will do whatever it takes to make me happy."

"Yes" said Walter, licking his lips.

"More than anything now, you want to become a *real* woman, so that you can please me."

"I want to become a real woman" said Walter. And he meant it. He didn't understand how Bert could seem so powerful that he just *had* to obey, but it was now. He would listen, and he would obey.

"Tomorrow, you will accompany me to the hospital. We will get you scheduled for your sex change. You will become a real woman. And you *will* go through with it."

"Yes" said Walter.

"Now kiss me, woman. Show me how much you belong to me."

Walter locked into a kiss with Bert. God, he felt so much like he was really a woman already. He wanted *so* much to please his man. He let Bert kiss him, and touch him. The more he did so, the more that Walter felt like a woman. He was Wendy now. Now and forever. He'd always be Bert's woman.

He looked up to his strong man, with puppy dog eyes. Wendy was in love now. Inside, she was a woman. It was just a matter of time before her body caught up.

  

  

  

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