Prize Catch

by Jennifer White

 

When Lisa walked into the office for the first time, turning with a swish of skirts, Thomas was already in love. He watched her as she walked to her cubicle, right next to his, gracefully took a set, and crossed her legs in that way that only a pretty woman can.

At that moment, Thomas knew he had to have her! He would do anything to get her. She was the girl of his dream. He didn't want to come on too strong and scare her off. But he didn't want anyone else to move in on "his" girl. So he decided to approach her.

"Hi" he said, extending a hand. "I'm Thomas."

"Lisa" she said, smiling, but not overly friendly.

"I'm in the cubicle right next to you" he continued. "I heard we were getting a new person here in the department. Let me be the first to welcome you. If you need anything, or help getting oriented with things here, please come and see me. I'll be glad to help."

"That's so sweet" she said, smiling, then turning to unpack her briefcase.

Thomas knew enough to back off. He didn't want to seem too eager. Then he'd look desperate (which he was, for her at least!). So he went back to work at his desk. But it was hard to concentrate, knowing that someone like Lisa was sitting right there, over the cubicle wall. He could smell her perfume, making it even harder.

As the other men at the office caught sight of her, they of course swarmed in, introducing themselves, trying to hit on her. Thomas could hear every single one of them, as they took turns trying to impress her.

Some were too quick to make a move, asking her for a date, even before they had talked for five minutes. Others made themselves sound foolish and immature. But some did a credible job. In either case, Thomas felt very jealous. She was his girl (or would be one day soon!).

It took a lot of discipline for Thomas to wait until Lisa's third day in the office, before he finally asked her out. He found himself alone in the mailroom with her, so it was the perfect opportunity. But she turned him down.

"That's so sweet of you" she said. "But I really can't. I'm sorry."

He shrugged his shoulders. Being rejected like that wasn't going to stop him. He was going to have her one day. He had to. She was the woman of his dreams.

 

* * *

 

Thomas was determined. He was going to have Lisa, one way or the other. Every time he heard a guy at the office ask her out, he'd hold his breath, his heart racing, as he hoped she'd reject them too. And she always did.

He asked her out again, but he too was politely turned down. He asked her to lunch. Again, she said no. He wrote her a note, asking her out. No. He invited her to dinner. No. But that didn't stop him.

"Hey Lisa, I've got tickets for John Mayer tonight" he told her, "but my friend George had to cancel. Do you want to go with me?"

"Sorry Thomas, but thank you so much" she replied.

Of course, he just tossed the tickets. He had bought them, because he had read that chicks dug him. He wasn't about to waste his time at a dumb show like that, if it wasn't with her!

Again and again he tried, but again and again he was turned down. No matter what he thought of, Lisa would never say yes to him. But finally one day, when he asked yet again, she looked at him and sighed.

"You are persistent, aren't you?" she said.

"When I really want something, yes" he replied.

"Okay. Listen. Tomorrow, lets have lunch together so we can talk. I'll be at The Garden Cafe, at 12:00. See you there."

"You can count on that" he said, beaming.

Thomas was floating on air. He was going out with Lisa! They were having lunch together! It was just a first step, but once things got going, she'd see how wonderful he was, and soon they'd be together. Just like he had planned it.

 

* * *

 

Thomas was at The Garden Cafe, right on time. There was Lisa, sitting there looking so attractive, in her shirt white skirt and her tank top. Thomas felt like he was the luckiest man in the world, to have a babe like her dating him! This was their first date. Soon, there would be many more, as she fell in love with him.

They ordered lunch, and made small talk as they ate. Thomas thought he was being clever, asking her about her family, and getting her to talk about herself. He tried to be an attentive listened, but of course he felt the typical unconscious male need to cut her off, so he could brag about himself. So while he thought he was showing her how wonderful he was, he was actually turning her off with his behavior.

Lisa sighed. Here was yet another man who didn't get it. It was time to let him know the truth. She was taking a risk in telling him; but he was being so persistent that she knew he'd never lay off, and she'd have to fight him off every day at work. She was sick of it. And so she told him.

"Thomas, you're so sweet" she said. "You're handsome, you're smart, you're a nice dresser. I really like you, as a friend. But you need to understand something: we can never go out. It just won't work between us."

"But Lisa, you hardly know me! Give me a chance before you reject me outright like that. We're just getting to know each other."

"You don't know anything about me" she said.

"I want to learn everything about you" he replied.

Here we go, she thought.

"Thomas, I need you to be quiet, and listen for a while. Can you do that?"

"Yes" he said.

"Okay" she replied, taking a deep breath. "Let me tell you something about myself. When I was in highschool, I was a cheerleader. I dated the captain of the football team. A real stud. We started having sex almost right away, but he was never able to satisfy me."

Thomas's eyes were almost bugging out of his head. He couldn't believe she was telling him this!

"I also dated the captain of the swim team. It felt empty with him too, and I wondered what was wrong with me. But one day, I was studying math with my girlfriend Becky. Another cheerleader. I don't know how it happened, but we were sitting very close together, and we ended up touching hands. Next thing I knew, we were kissing. Any my heart raced."

She had Thomas's full attention, to be sure! Again, he couldn't believe he was hearing this from her! On a first date! He decided that this chick was going to be wild in the sack. But he wasn't ready for what was coming next.

"We made love that afternoon" she continued. "And for the first time in my life, I felt that something that was missing inside of me! In secret, we dated all through highschool. But when it was time for college, her parents made her go out of state, so we broke up."

Her eyes looked down sadly, as she missed her first girlfriend.

"In college, I dated guys. It was always the same. They acted one way at first, as they pursued me. But then once they had me, they changed. And in bed, it never felt as good as it did with Becky. So I started dating girls. When I was in bed with my first college girl, I knew that I had found my true self. It was then that I swore I'd never date another man, as long as I lived."

"So...." said Thomas, shocked.

"Yes Thomas" she replied frankly. "I'm a lesbian. I date girls. Men hold no interest at all for me. Only a woman can fulfill me emotional and physical needs. So as I said, you're very nice and all, and if I was the type to date guys, I'd give you a try. But you're not a girl. So we can never be together."

Lisa had just poured out her heart, admitting her dark secret to someone who was almost a stranger. She had let her guard down, and exposed a part of her inner self, which could make life difficult for her in the office. She didn't think he was the vindictive type, who would go around telling the guys not to bother, since she was a "dyke", as one man had done to her when she had told him.

She sipped her iced tea, and looked at Thomas, waiting to see how he would take the news. She didn't want to hurt his feelings, but it was apparent that he would never stop pursuing her, and she needed to make him understand that they would never be together.

Thomas should have reacted by being kind, and asking if they could still be friends. But much to Lisa's chagrin, he had a different reaction, one that was so typically male: he took her revelation as a challange. He thought that he was such a man, that if she were to give him a chance, he could "turn" her back. Instead of giving up, he kept on trying to get her to date him!

"....and so if you'd just give me one chance" he said.

"Look" said Lisa, her voice betraying a hint of anger now. "How would you feel if some cute guy at the office asked you out? Would you give him one date, so that he could make you see the light?"

"I don't date guys" said Thomas, matter-of-factly.

"And neither do I" replied Lisa.

He hadn't considered her feelings at all. It was so typically male. Selfish, never thinking of others. Thinking the world revolved around him. She had poured her heart out to him, and that didn't matter! He was still hitting on her, still trying to get her to go out with him!

Lisa decided that she had enough. She couldn't take any more of this. As long as she worked in that office, he was going to hit on her, along with many of the other guys. It wasn't her fault that she looked like a beauty queen! Sometimes, she wished she had been a "plain Jane", so she wouldn't have to deal with all this unwanted male attention.

She decided that she needed to teach him a lesson, and perhaps at the same time, set an example so that the other guys in the office would lay off. She waited until Thomas finished his latest plea for her to go out with him.

"Okay, you win. We'll go out on a date" she said.

She saw Thomas puff out his chest a little, as in triumph. He thought he had won. He didn't realize what he was getting himself into!

"But it will be on my terns" she continued. "Meet me here for lunch on Thursday, so I can go over my terms with you. Then on Friday, we'll go out."

"I'll be there" he said.

"Okay then" she replied.

 

* * *

 

The week seemed to drag by so slowly for Thomas. He couldn't wait for his date with the woman of his dreams! He wondered what her "terms" were going to be, but that didn't matter. They were going out!

For her part, Lisa was a bit perturbed that word was getting around the office that Thomas was dating her. They hadn't even gone out, and everyone seemed to know already. She hated how men felt such a need to brag about their conquests. That's why she had broken up with the football team captain; he had bragged that they were "doing it", and she dumped him right away.

At least though, since everyone knew they were going out, it did cut down on the other guys trying to flirt with her, or ask her out. But she hated how they'd stare at her boobs in the elevator, or check out her legs, instead of looking her in the face.

On Thursday, she went to lunch early, so she could make sure to get a secluded booth. She waited patiently for Thomas to arrive. True to his word, he was right on time. He sat down, and they ordered their meals. It was only after they ate that she would get to her terms and conditions.

"I've been hearing people at the office talking about us" she said, nonchalantly.

"I told Dave, and he might have told a few others" said Thomas, thinking up a lame excuse. Of course, he had been bragging to all they guys, so they'd know to keep their paws off of "his" Lisa.

"Now as I said, if we're going to date, it will be on my terms" said Lisa.

"Yes, I remember" said Thomas.

"You may not like them, but if you can't live with them, then you can forget the whole thing" she added.

Thomas nodded his head. Now he'd learn what she wanted from him.

"As you know, I'm attracted to women" said Lisa. "I love how soft and smooth their bodies are. Hairy legs or a hairy chest are a real turn-off for me. If we're going to date, you need to remove all of your body hair, and start using lotion to keep your skin soft and smooth. Do you agree?"

"Sure" he said. He could live with that.

"Good" she replied. "Secondly, if we are to date, I need for you to prove to me that you really do care about me, and that you're not just in this for sex."

"I'm not!" he protest. "I really feel like I'm falling in love with you, and I want to be with you forever. Its not just sex."

A line many guys had tried on her before! In they end, they did only want one thing from a woman, no matter what they said.

"Then prove it to me" she said. "I'm going to ask you to do things from time to time, and I need to see you do them for me. If you can't come through with what I ask, then I'll know you don't really care about me."

"Just ask me, and I'll do it" said Thomas.

He was foolish to say that without first hearing her request, she thought!

Lisa reached down to the set next to her, and picked up a white box, which she handed over to Thomas.

"What's this?" he said.

"Open it up" she replied.

 

He took off the top, peeled back the tissue paper, and stared at the sexy white lace bra and panty set inside the box.

"If you want to date me, you need to have those on" she said. "You need to wear them tomorrow to work too. I'll check on you during the day. If you shaved off your body hair, and you come into work wearing your bra and panty set, then we're on. If you don't, then no date. Got it?"

"Yes" he said, although she could detect a tremor in his voice.

"And I have one more term, which I'll tell you on our date, should you show up."

Perhaps this alone would scare him off, and she'd be rid of him.

 

* * *

 

But Thomas was too persistent to be scared off so easily. Lisa got a conference room booked for half an hour, then called him in. She shut the door and locked it.

"Show me" she said. "Unbutton your shirt."

With his back to the door, Thomas threw his tie over his shoulder, unbuttoned his shirt, and exposed both his smooth hairless chest to her, along with the bra he had on underneath. After he buttoned his shirt back up, he pulled up the leg of his trousers, to show that his leg was also shaved.

"How does it feel to be wearing a bra?" said Lisa.

"Really strange" he replied.

"Don't you love the feel of the sexy soft material, as it cups your little boobs?" she said. "Don't you love how your panties caress you with their softness, enveloping the special spot between your legs?"

Her talking like that turned him on, and it showed.

"I see you like it" she said. "I can see how hard you are. Now are you going to admit to me that you like wearing your bra and panties?"

"Yes" he said, "I like it."

In truth, he had been terrified all day of being found out. He felt so strange about it, and now she made him get hard, and tell her that he liked it! For the first time, he wondered what he was getting himself into.

 

* * *

 

Thomas showed up on the date, wearing a nice casual shirt, black slacks, good shoes. And of course, the bra and panty set underneath it. For her part, Lisa wore a pair of black jeans, and a cami top, along with heels. Far more casual than she wore at the office, but really attractive!

Lisa inspected Thomas, making sure he still had his bra on. He did. She smiled. She didn't think he'd go through with this. But he'd be scared off after she told him her next demand. She showed him a glimpse of her own bra, so he cold see that it was an exact match for his, just with a much larger cup size.

They ate dinner together, talked and laughed. It was like most first dates, other than the fact that they both had matching underwear sets on.

"If this is going to work between us" said Lisa, "You're going to need to change a few things for me. I've already been upset at some of your typical male behavior. Things you probably don't even notice, but which are upsetting for a woman. I know you don't understand, but you will, in time."

Thomas nodded, but as she said, he didn't even know what he did wrong.

"Your problem is that your male behaviors are a part of you that is so ingrained, you don't even think about them. It is just who you are, and how you act. But if we are going to date, this is unacceptable to me. I've dated women who were kind, considerate, and selfless."

"I'm kind and considerate" said Thomas defensively. "I can be selfless."

"If you want to date me, you'll have to be" she said. "If you want to be with me, I'm going to have to hunt down and destroy these male traits of yours. I'm going to erase the macho in you, and replace it with femininity. Those are my terms. You can date me, if you're willing to let me turn you into a woman on the inside. You have to agree to let me feminize your innermost self."

There. Now he'd back down for sure. But Thomas still didn't get it. He still thought that once he got "into her pants", she'd "turn", and all this talk would go away. She'd melt, and become his.

"I can do that for you" he said. "I care for you that much."

Lisa wasn't very happy to hear that. But she shrugged her shoulders. Maybe this could be fun for her. Maybe should could teach him, and all the guys at the office for that matter, a lesson. She'd make an example of him, and then they'd all leave him alone.

 

* * *

 

On Monday, Lisa dropped a hand written note off to Thomas. It was on pink scented paper. It read: "Dearest Thomas. Today at lunch, go to the lingerie store on 4th street, and buy for yourself a pair of sheer control top pantyhose. Come back to work in them, and show me. If you do, you'll be very glad. If you don't, then I'll know our deal is off. Love Lisa."

Love! She called him 'dearest', and said love! He rushed to the store, and with mild embarrassment bought a pair of pantyhose for himself. Then he ate lunch, and went into a stall in the men's room, so he could put them on.

When he returned, Lisa waved him over.

"Do you have them on?" she asked.

"Yes" he replied.

"Show me" she said.

 

He pulled up his pant leg far enough to show that he had nylon on under his slacks.

"How does it feel to have your legs wrapped in nylon?" she asked.

"Kind of funny, the way it feels when my pants rub against it, but not too bad."

"I hope you like it lover, because you'll be wearing them every day from now on, along with your bra and panties. You'll do that for me, won't you?"

"Yes" he replied.

Then, right there in plain sight, where everyone could see, she gave him a kiss. Just a little peck really, but word spread like wildfire in the office: Lisa and Thomas were kissing! He of course was elated. He felt like the king. Lisa was his now.

Thomas was too male to realize that she wasn't becoming his; he was becoming hers.

 

* * *

 

The next night, Lisa cooked dinner for Thomas. After they ate, she had him wash the dishes for her, while she went to go get something ready for him. When he returned to the livingroom, she had an outfit laid out on the couch.

"This is a woman's suit" she said, "but you'd never know it. The pants look pretty much like men's but you'll find the zipper in a different location than you're used to. And the blazer is about the same too, but cut so that you've got more room for you boobs. Try it on!"

Thomas wasn't too sure, but she encouraged him. He stripped down to his bra, panties and pantyhose, then put on the women's pants, zipping them up in back. Then he put on the blazer, and he could feel the extra room in the chest.

But when he looked in the mirror, he realized that she was right, you'd never know it was a woman's outfit. It was so close in style to a man's, that nobody would think anything of it.

"Only you and I will know that you're dressed completely as a woman" she said. "You don't know how much that turns me on!"

If it turned her on, then it was all right with him.

"How does it feel to be dressed completely as a woman, for the first time?" she asked.

"Strange. I never thought I'd do this" he replied.

"Oh, you'll do a lot more then that, when I'm done with you."

 

* * *

 

On Friday, Lisa and Thomas went to lunch. They shopped for new shoes together. She bought herself a pair of exciting looking pumps, while she selected a pair of flats, then asked for them in a ridiculously large size. The saleswoman shrugged, and brought them from the stock room in the back.

"You're lucky that this store specializes in larger sizes" she said. "But these are way too big for you dear".

"Oh, they're not for me. They're for him" said Lisa, pointing to Thomas, who was so embarrassed, he blushed bright red.

The saleswoman fitted them onto his feet, then he stood up to model them. As with the suit he was wearing, they shoes didn't really stand out. They were so androgynous, that you couldn't tell that they were women's, except for two things: the size, and the higher price.

Lisa insisted that he wear them back to work. As they strolled down the street, hand in hand, she looked at him and smiled.

"It bothered me that you were dressed as a woman, but wearing men's shoes. Now your outfit is complete. From head to toe, you've got nothing male on you. You are now completely dressed as a woman."

"That seems so strange" he said.

"You'll get used to it, princess" she replied, giving him a kiss.

Princess? Him? He didn't like that very much, and he hoped it was just a one time thing. But much to his discomfort, whenever they were alone, Lisa started using that as his pet name. No more "dear", no more "love". Just "princess".

After work, they went to Lisa's house. Before they ate, she insisted on taking him into her bedroom, sitting him down, and putting makeup on his face.

"I have such a hard time flirting with someone who doesn't have mascara on. I think it makes your eyes look so pretty! And now a little lipstick, a shimmery pink to make your lips look more kissable, princess. There. Now you look much prettier."

Thomas saw himself in the mirror, wearing makeup for the first time. He didn't like how he looked at all! But she had called his lips "kissable", and he really wanted to make out with her that night. So he let it go.

Lisa was putting the cosmetics she had just used on him into a small pink purse. He noticed that the purse had glittery letters on the side, reading 'princess'. Even before she handed it over, he knew it was going to be for him. He shuddered as he took it from her.

"From now on princess, when you arrive here for a date, I expect that you'll have your makeup on. Okay?"

"Okay" he replied sheepishly. What was he getting himself into?

"This weekend, we'll practice, until you get good at it. At work, you'll only need to wear a little. Lets say some foundation, and maybe just a touch of blush. But enough talk about work! Lets eat, and then I'll show you some exciting new clothes I bought for you."

All through dinner, Thomas felt scared. What was she going to make him wear now? He felt like the situation was spinning more and more out of control. He was losing control of everything, to her. He had to act fast, and get her into bed, so he could make her his, before it was too late!

But that night, after doing nothing more than kissing, he walked out to his car, carrying a hanging bag with another woman's suit, new blouses, and a red bra and panty set for him to wear to work on Monday.

 

* * *

 

"Princess, why don't you wear your new white blouse for me tomorrow" said Lisa, as they talked on the phone at 11:00 on Tuesday night.

"But it is kind of ruffly" said Thomas. "Someone might notice."

"Not if you keep your jacket on, princess" she replied. "You'll do that for me, won't you?"

"Yes" he said.

"Mmmm, I like that" replied Lisa. "The thought of you all pretty makes me feel all wet. I'm putting my finger down into my panties right now, think of you looking all pretty in your makeup and your blouse."

"You're turning me on too" he said. Lisa had never initiated phone sex before! This wasn't as good as the real thing, but it was better than nothing. He started to stroke himself gently.

"You're getting me hard" he said.

"No" said Lisa forcefully. "I'm getting you wet. You need to tell me how your pussy feels. If we're going to have phone sex, you need to do it correctly. Now lets try again."

"Um, you're getting me all wet" he said.

"Me too, princess" she replied. "I'm taking my finger, and gently touching my clit, thinking of you. Now my juices are really flowing."

"I've got my hand in my panty" said Thomas. "My, um, clit is so tender, I feel so excited! I'm touching myself, thinking of you and how sexy you look."

"I'm sliding my finger into my wet pussy" said Lisa, breathlessly. "I'm thinking of you in your lingerie, and, oh! You're making me come!"

"My finger is in, uh... my pussy" said Thomas. "You're making me come too!"

Lisa was moaning now.

"Your pussy is so sweet, princess" she said. "Your sexy body is so feminine, so fragile, so soft. I'm imaging my tongue sucking on your sweet pussy now. How does it feel to have me lick your pussy?"

"Wonderful!" said Thomas. "I'm licking yours now too."

Moments later, he came in his panties. Now they would need to be washed. Lisa had manipulated him into talking about "his pussy", and had made him come. He thought that it was just phone sex. He didn't realize that she was starting to train him.

 

* * *

 

Of course, just as she asked, Thomas wore his frilly blouse under his blazer at work the next day. She rewarded him with another kiss in front of half the office, as well as with a gift. He opened the box, and looked at the skimpy red teddy.

"Next time we have phone sex" she said, "I want you dressed in that. In fact, I want you to sleep in it every night, from now on. For me."

"Okay" he said meekly.

As he went to bed wearing a nightie, Thomas felt very worried. So far, he was doing everything she had asked of him, yet he hadn't gotten any further than a kiss. And that was at work! But at least it was in front of enough people that everyone knew he was dating her. That made him feel important, and proud. Everyone admired him! Little did they know, that his prize catch was in fact turning him into a woman!

 

* * *

 

On Monday, Thomas stopped by Lisa's cubicle, carrying a cup of cappuccino for her. But she wasn't there. In fact; the cube was cleaned out. Thomas felt a sinking feeling come over him. She was gone? She hadn't told him she was leaving! He almost felt like crying. After all he had done, she was gone, just like that?

He was in shock as he sat down at his desk, and looked through his email. But his thoughts were interrupted, when his phone rang. It was his boss.

"Thomas, I'd like to see you in my office now" he said.

"Yes sir" replied Thomas.

He was terrified that someone had noticed that he was wearing women's clothes. Someone had turned him in, and now he was going to be fired! He had just lost his Lisa, and now he was sure he was going to lose his job. He felt ashamed and humiliated. It was with great trepidation that he opened his boss's door after knocking, and walked in.

"Thomas, have a seat" he said.

Thomas took a deep breath, and sat down. He braced himself for the worst.

"Thomas, you've always been a good worker for me. You've always done an admirable job, you take care in all your duties, and I've always felt like you were a natural leader in the department for me. But sometimes, things have to change. And unfortunately, I'm going to have to let you go."

Thomas almost cried. He was about to be fired! He was to shocked to know what to say.

"You see" continued his boss, "I got a call from upstairs, on the 5th floor. They requested that I transfer you up to them. Go report to department J. You're on the executive floor now my boy. Congratulations."

Thomas was floored. He wasn't being fired, he was being promoted! He said 'thanks', excused himself, and hurried to the rest room. He needed to wash his face! But of course, he had to be careful of the light makeup he was wearing. He'd never wear it again, and he'd go back to his own clothes tomorrow, now that Lisa was gone. What a change of life, in just one day!

He got off the elevator on the 5th floor, where he had only been once before in his career. This floor was reserved for executives in the company. And he was going to work here now! He asked the receptionist where department J was. She smiled, and pointed towards an office in the corner.

He knocked, then entered. When he laid eyes on his new boss, his face went white, as he almost entered a state of total shock. Sitting behind the big desk in the executive office was Lisa!

"Shut the door Thomas. Have a seat" she said.

"I thought you were gone when I saw your empty cubicle" he said, his voice cracking.

"I'm sorry I didn't tell you. I didn't tell anyone. You see, when they hired me to be the vice president of finance, I insisted that I work with the average folks for a month. I wanted the regular workers to get to know me, so it wouldn't be like I just swooped in, and took over a high ranking job. I wanted to gain their respect first."

"So you were hired to be a VP all along?"

"Yes" she said. "This is where I truly belong. And I'm bringing you up with me. Do you remember our conversation, about the conditions for you to date me?"

"Yes" he replied.

"And do you remember how I told you that I was going to burn out the macho in you, and replace it with soft femininity?"

Thomas nodded.

"The clothes I've got you wearing, the shoes, the makeup, all of that is just window dressing. Putting a bra on does not make you become a woman. Being my little princess, and wearing a nightie doesn't make you a girl either. The man in you still wants to control me. But now you'll be working for me. I will control every aspect of your life."

Thomas just stared, blankly, still in shock about the whole situation.

"First of all, since you work for me now, we can't be seen kissing in the office, holding hands, or showing any affection at all. You need to treat me as your boss when we are at work. Do you understand?"

"Yes Lisa" he replied.

"Hmm. I can't have my secretary calling me 'Lisa'. That is too informal. When we're in the office, you need to address me with a title of respect. From now on, you'll call me Ms. Wolford."

"Lisa..." he said in protest.

Lisa's tone turned harsher than Thomas had ever heard before. She became angry, with a glare in her eyes as she scolded him.

"That's Ms. Wolford to you. And don't ever do that again! If anyone sees my secretary questioning me, it will undermine my position. I'm not going to let you make me look bad at work. If you can't handle being my secretary, then you can just pack up your desk, and go home now. And needless to say, if I have to fire you, we're through."

"I'm sorry. Ms. Wolford" he said, sheepishly.

Things were getting worse, and worse, spiraling out of control! Now if he didn't do what she said, he'd be fired, and she'd break up with him. And he was going to be her secretary! That was a job for a woman. And they couldn't be seen dating at work! And now he had to call her Ms. Wolford. Worse and worse, indeed!

"As you can see now Thomas, I control every aspect of your life. You are completely mine now. With a word, I can have you sent home jobless, and I can make sure nobody will ever hire you again in this industry. I'm sure I can count on you for complete obedience now, can't I?"

"Yes Ms. Wolford" he said.

"So you can see princess, there is no chance of you being the man in this relationship. You are completely subordinate to me now. You'll never control me, you'll never be the one in charge. I will always control you."

It was totally emasculating to have her do this to him. He felt like he was less of a man already, as he realized how much she controlled him now.

"Now back to you and your femininity" she said, her voice becoming softer again. "One thing that women have that you don't, is boobs. I could never be attracted to someone with a flat chest. If you're going to be my girlfriend, you're going to need boobs of your own. But until we can find a time to get you permanent implants, I want you to start wearing these."

She pulled out a box from under her desk, which was labeled "breast forms". She opened it, and showed him the contents. Two large lumps of silicon gel, shaped like perfect female breasts. They had areolas, nipples, and everything.

"Put these into your bra. Now" she said. "They're just b-cups, so they won't show too much. I have a pair of D-cups waiting for you at home. You'll wear those when we're alone. But I'll let you wear the smaller ones at work. For now."

She pushed the box over to him. He didn't have any choice! He had to put them into the cups of his bra. His hands were trembling as he placed them in. At first, they felt cold against his skin, but soon they warmed up.

As he looked down, there were two soft, gentle mounds on his chest now, making his blouse push out in front of him! It made it look like he had little boobs! Someone would notice for sure!

"Now come with me. We have an appointment" she said.

"What appointment?" he asked.

"I told you not to question me! Tell me your sorry, right now."

"I'm sorry" he said.

"I'm sorry what?"

"I'm sorry, Ms. Wolford" he said.

"That's better. Don't slip up like that ever again! And if you do it in front of anyone at work, you will be so sorry. Don't cross me Thomas, or you'll truly regret it."

He had never seen her like this, being so forceful, so angry. He felt so helpless! All he could do was to obey her.

"We can't be seen leaving together. Go out to my car, and wait for me. I'll be along shortly."

Thomas hurried through the office, hoping nobody noticed his new boobs. He crossed his arms over them as he rode in the elevator, so he could better hide them. Then he went to Lisa's car, and waited.

Five minutes later, she arrived. She opened the passenger door for him, and held it open until he got inside. Then she shut it, walked around, and got in on her side. Just like a guy does for his girlfriend. Thomas shuddered.

Lisa drove a few miles away, then pulled up at a strip center.

"Come with me" she said. "Remember, we're on working hours. To you, I'm still Ms. Wolford. And you will not question me in front of the people we're going to see. Do you understand?"

"Yes" he replied sheepishly.

"Oh, and one more thing princess. When we're here, the name Thomas doesn't exist. I'm going to introduce you to everyone by your new name."

"My new name?"

"Yes, Stephanie."

 

Stephanie? She was going to call him that? He blushed already. She was going to introduce him to someone with a woman's name? What was she going to do to him?

He was frightened as they walked out of the car, and into a beauty salon. Lisa waved him over to a chair, and had him sit down. She was chatting with a woman, who smiled, then came over.

"Stephanie, this is Kelli."

"Hi" he said quietly, his voice trembling. Kelli offered her hand, and gave him a good hard handshake. She was a knockout too.

"Kelli and I dated for awhile" said Lisa, "But it didn't work out."

"Both of us wanted to be the man" said Kelli, causing both her and Lisa to crack a smile and laugh.

"So you are among friends here" said Lisa, reassuringly. "Now lets see. First of all, we need to do something with your hair. You have too masculine of a style. Kelli here is a genius with the clippers. Lets see what she can come up with."

Thomas sat there, as she started to work on his hair. Lisa was saying that from now on, he'd let it grow out, so it could become long enough that they could really make it look pretty.

"I think we'll go with a perm, for some little curls" said Kelli. Its a shame that your hair isn't longer now, or I could really make you look like a darling."

Thomas had to sit there as she did all sorts of things to his hair. Smelly goop, curlers, sprays, and more. When she was done with him, he could only stare at himself in the mirror, seeing his new hair style, with the tight curls on his head. Very feminine.

Now Lisa took him to see a manicurist. He was given nail extensions, followed by both a pedicure, manicure, and bright pink nail polish on both his fingers and toes.

"Stephanie, I want you to take care of your nails. Try not to chip them. You'll have a standing appointment here every week to get them redone. From now on, you're going to have long painted nails, all the time."

As Thomas stared at his long nails, not believing that they were on his hand, Lisa had him sit at another station. The girl there put something up to his ear. There was a momentary burst of pain, then she slipped something into the hole she had just made in his earlobe.

"Now don't take these out for a month, or the holes could close up" she said, as she prepared to pierce his other ear. Earrings, on him! He couldn't believe it! Again, he just sat there, as Lisa put a pretty necklace on him, and the girl did his other ear.

Then she put bracelets on his wrists, and a couple of rings on his fingers.

When the second girl had done the polish on his toenails, she had put him into a pair of flip-flops. Now his toes were fully dry, so Lisa gave him shoes to put on. But they weren't the shoes he had worn when he came in; these had a thin two inch heel! She slipped them on his feet, telling him that they were far prettier than this old pair.

He stared at them, as he was sat down now at a station with three large lighted mirrors. He watched himself, as the girl there started to apply makeup to his face. She put something dark around his eyes, followed by an application of mascara. She put powders around his eye sockets, and something on his eyelids. Then she used a brush to apply something red to his cheeks, followed by an application of bright red lip gloss.

Now his face was fully made up, and he was starting to look even more like a woman. He could hardly believe that it was him in the mirror, looking like that, with the curly hair, the jewelry, the long nails, and now the full makeup. But Lisa wasn't quite done with him yet.

She had him follow her into the women's room, where she locked the door. She was carrying a bag with her, when she handed to him.

"Put this on, princess" she said.

Thomas opened the bag. There was a hanger inside, holding a neatly folded garment. A skirt! He took it off the hanger, and just stared at it.

"It is a perfect match for your suit" she said. "Now that you're my secretary, you won't be wearing pants into the office anymore. I want you to show up in a skirt every day from now on. Do you understand me, Stephanie?"

"Yes Ms. Wolford" he managed to say.

"Now Stephanie, don't cry. You'll ruin your makeup. It isn't that bad. Nobody on the 5th floor knows who you are. I informed them that I'd be bringing a girl from downstairs with me. They all think you're a girl already. So they will expect for you to be dressed like you are."

The executives at work thought he was a woman? This was getting worse and worse!

"You'll have to learn to walk more gracefully in your heels" she said. "Oh, and don't forget to always carry your purse with you. A woman never lets it out of her sight."

She handed Thomas a small black purse, with a long thin strap.

"At home, we'll work on proper feminine posture. How to sit, how to stand, how to cross your legs like a lady. At home, I want you in heels and a dress or a skirt at all times, until it becomes second nature for you. Do you understand?"

"Yes Ms. Wolford" he replied.

"Good girl Stephanie. I think you make a lovely woman."

When she paraded Thomas back to her office, in front of everybody, he felt completely humiliated. She was showing him off as a woman to everyone! Now everyone would know that not only did she control him, but had had allowed her to turn him into a woman! But as bad as that was, there was still more to come for him!

Back in her office, she pulled out a stack of papers from her desk.

"Sign this" she said.

"May I ask you what I'm signing?" he said, as he put his signature onto the paper.

"That one is for power of attorney. It will allow me to act on your behalf. You'll be moving in with me now, Stephanie. I can't have you going to your own house, and reverting. You need to stick close to me, so I can make sure you're immersed in the feminine at all times."

Thomas could only stare blankly, as he realized what his life was becoming.

"After I sell your house, and donate all your clothes and things to charity, you'll start to build your new feminine wardrobe. You will dress as a woman all day, every day, from now on. In fact, now you're going to sign these papers, so we can make a legal name change for you."

He signed them, with a blank expression on his face.

"Now your legal name is Stephanie Marie. We'll have to go get your driver's license updated as soon as the paperwork comes back."

Thomas had to work as her secretary all day, sitting at a desk outside her door, keeping track of her calendar, taking her calls, running errands for her, making copies, and any other menial task required. The most "empowering" thing he got to do all day was to input some financial data into a spreadsheet for her.

He drove to her house after work. She informed him that she was going to sell off his car, since it was too masculine.

"You'll be driving a minivan from now on. Like a "soccer mom" would."

She made him cook diner for her, then serve it. After they ate, they sat on the couch together, watching a movie, as she had him scratch her lower back with his long nails. When they finally went into the bedroom later that night, she had him put the D-cup breast forms into his bra, before putting on his skimpy nightie.

But Lisa herself was putting something else on: a strap-on! It was a black leather harness, with a bright pink dildo. He could only stare at it in amazement. There she was, her perfect breasts exposed to him for the first time, but she was wearing something to make it look like she had a big pink d*ck.

"Do you have to wear that?" he asked.

"I do all my girlfriends with it" she said. "Does the fact that its pink bother you? I have another one that looks more realistic, if you prefer."

"Um, no..." he said.

"Good. Now rub some lubricant on it for me, so it goes in nice and easy. I don't want to hurt you, especially since this will be your first time."

It was terrible rubbing the K-Y jelly onto her dildo. But it was even worse when she had him bend over the bed, so she could slide herself up inside of him. As she gently pushed herself all the way in, she reached around him, and started to rub his penis, until he got hard.

She would thrust once, then give him a quick jerk. Then she did it again, and again, until he was on the edge of coming.

"Please stop it, I want to come inside you" he moaned, as she thrust into him yet again.

"I'm not going to allow you to put your c*ck into me" she said. "Not until you have real boobs of your own. The night that you come to bed with implants that are D-cup or bigger, is the night that you'll get to come inside me. Until then, I will be the one doing the penetrating."

Thomas tried to hold back, and let the pleasure last as long as possible. But Lisa was too good, and against his will, she made him come hard. But she wasn't quite done with him yet. Now she laid on the bed, and spread her legs wide open.

There was enough of an opening between the straps that her pussy was exposed. She pointed to it, and told him to get on his knees and lick.

"Can't you take that thing off first?" he said.

"No" she replied. "You need to learn that I am the man in our relationship. It will stay on, whenever we are in the bedroom together. Now get on your knees, and lick my pussy!"

He fell to his knees, and started to lick. That thing was sticking right in his face, as he tasted her sweet juices for the first time. She was very wet. Obviously, controlling him like that was a huge turn-on for her! As he licked, she talked to him.

"I'll wear my d*ck all night. When I'm pressed up close against you, you'll always feel it poking you, like it wants to get inside you all the time. Sometimes, I'll have you jerk me off, as if it was real. I'm going to make you want it. I'm going to make you feel so much like a woman, that you're going to crave c*ck."

Thomas had a tear in his eye, as he continued to lick her pussy.

"Soon, you'll have boobs of your own. You're going to want to become more and more feminine for me. In fact, soon you'll beg me to let you go on female hormones, so more of your body can change. You're going to become a chick, Stephanie. A chick with a d*ck. And you'll be my woman."

Now Thomas was crying.

"You're in love with me now, but soon, you'll start to understand that you're more my slave than my lover. Oh, we'll get married all right. But you will be the one in the white gown. In front of all your family and friends, you will be the bride. They'll all know that you've become my slave, my plaything, my woman. I own you now, and there is no escape."

Thomas's face was buried between her legs. How much trouble had her pussy gotten him into now? Why had he let it go this far?

"As you lick me now" she said, "Put your right hand onto my d*ck. Pretend that you're jerking me off. I'm about to come, and I want you to feel like you did it by stimulating my penis. I'm your man now. And you are my woman."

It was with utter humiliation that Thomas did as she asked, finally making her come. When she was done and too sensitive, she pushed him away, and told him to get on his knees. She stood up, towering over him, the dildo of her strap-on pointing right at him as he looked up at her.

"I'm just getting started with you, Stephanie" she said. "Today was just one little tiny step. I'm going to make you completely mine. You're still thinking things that I don't want you to think. But soon, even your deepest inner thoughts will be the ones that I desire. You'll think and feel exactly what I command you to think. I know you can't understand it yet, but you really are going to become my complete and total slave."

He just stared at her, not knowing what to say.

"I'm going to dominate you in every way. Soon, you won't take a breath without asking my permission first. I will demand total and complete obedience from you, and you will give it to me. Now repeat after me. Tell me that there is no more Thomas, there is only Stephanie now."

"There is no more Thomas, there is only Stephanie now" he said.

"Use a sweeter, more feminine voice Stephanie. You're a girl now. Tell me that I am your man now, and that you're my woman."

"You are my man now, and I am your woman" he said in a higher pitch, trying to please her.

"Good" she replied. "Tell me that you wished you had a pussy like I do."

"I wish I had a pussy like you do" he said.

"Tell me that you loved having my d*ck inside you, and that you want me to f*ck you every day from now on."

"I loved having your d*ck inside me, and I want you to f*ck me every day from now on" he repeated.

"Excellent. Now tell me that you're not a man, and that you never were a real man."

"I'm not a man" he said. "I never was a real man."

"Yes" she said. "I never looked at you as a man. From the moment I met you, I only saw your feminine potential. Oh, and another thing, do you know Frank, across the aisle from you at work?"

"Yes..." said Thomas. Frank was a frail little man, a real wuss. Everyone in the office laughed at him, because he was such a push-over.

"I've been sleeping with him. He's been screwing me every day" she said.

"No!!!!" said Thomas.

"Oh yes. He's so much more of a man than you ever were. I want to get pregnant, but I wasn't about to let your sperm into me. You're not even a man. Not even as much of a man as Frank."

Now Thomas was completely crushed, not to mention what was left of his male ego. He couldn't penetrate her, but she let Frank into her pussy? He wasn't even as much of a man as Frank? What did that make him?

"But so far, we haven't had any luck. So this weekend, you and I are going out to a few dance bars. I want you to find a good stud for me, and flirt with him. Get him to come home with us, so I can make love to him, and get pregnant. You can find a stud for yourself too, if you want to see what a real man is like in bed."

"No!" said Thomas. "I only want to be with you!"

"That's right princess. I'm your man. So you can watch as the stud you pick out makes love to me. Won't that be exciting, to watch a real man get hard, and put himself into me? While you watch and jerk yourself off?"

Thomas was in misery now. His dream had turned all around. His life was completely out of his control.

"That's right" said Lisa. "You were never enough of a man to satisfy me. The only way you can get me to love you, is if you completely and totally devote yourself to me, and completely utterly devote yourself to becoming a woman. If you become a woman on the inside, I will love only you, and I'll not want to be with anyone else. If you can become a girl on this inside, you'll have me. The moment you think of yourself as a woman, I'll be head over high heels in love with you."

She leaned over and give him a deep kiss.

"Just let go of that stubborn bit inside you that insists you're a man. Give yourself up to me, let me control you completely. I'll make you become a woman, and then I'll make you so happy. We'll always be together, two women in love. All you need to do is to let go. Give yourself to me. Let your manhood go! Accept womanhood, and become mine."

 

Of course, Lisa hadn't actually slept with Frank. She wasn't planning on having sex with other men either. She was a lesbian after all, and the thought of making love with a man disgusted her. If she did want to get pregnant, she'd use artificial insemination.

But the effects of her words had the desired effect on poor Thomas. They totally crushed him, breaking him down, leaving him completely vulnerable. Now, he was in utter misery. But if he would just let go of maleness, and fully accept that he was a woman on the inside, he'd have Lisa all to himself. Or "herself" to be more precise.

If he held on to manhood, it would only bring pain and suffering. But womanhood would be a shining light of happiness and love. Inside, he decided that he could give up holding on to what he had always thought and felt. He could be happy, if he and Lisa were together as one, forever.

"I want to be a woman" he said. "I want to be yours."

Lisa smiled. Acceptance was the first step. Soon, she would have him believing he had always been a woman on the inside. Then she'd finally have it all. A friend and a lover who could completely satisfy her. A female appearance and personality to turn her on and make her life tolerable, but a man's private parts.

The aspect of control over a male really turned her on, as did the idea that he would be so devoted to her, that he'd do anything. In return, she'd give him her heart, once he accepted himself as a woman. Together, they would both find the happiness that they deserved.

 

* * *

 

Epilog:

It was less than a month later when Stephanie had her first surgery. She had breast implants, D-cup size, as Lisa wanted, along with a nose job. The couple had several more planned, to help Stephanie gain the feminine appearance she so craved.

While Stephanie was still legally a male, the two were married in a private ceremony. Stephanie wore the white dress, while Lisa wore a rented tuxedo. On their honeymoon, she allowed Stephanie to penetrate her for the first time. She gritted her teeth, and pretended that her lover was wearing a strap-on.

She knew that since Stephanie was on hormones now, soon 'she' would loose the use of 'her' penis. This was the once chance she'd give Stephanie to get her pregnant. As luck would have it, nine months later, Lisa gave birth to a healthy baby girl, who they named Leslie.

Stephanie quit her job as secretary, so she could stay at home and raise their baby. They didn't need the small salary that she earned, since Lisa was rising so rapidly up the corporate ladder. When word spread, even among the executives, that she had taken a lover, and turned him into a woman, she was feared.

Nobody dared cross her. Her demands at work were quickly met, and they were always to the benefit of the company. By the time Leslie was out of diapers, Lisa was already the number two executive at her company. And by the time that Leslie started school, she reached the post of CEO.

All three girls are happy together, living a wonderful rich life full of warmth, love, caring and all of the other things that makes a woman's life worth while.

 

The End

  

  

  

*********************************************
© 2005 by Jennifer White. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.