All To Be

by Jennifer White

 

Tom had a secret. A deep dark secret, which he kept hidden, even from his wife Chrisy: he longed to be a woman sometimes. Not to really become female, but to dress up and pretend. It wasn't like he wanted to be with a guy or anything. He loved women, particularly his wife. But he had an inner need to be feminine sometimes.

He had been like that ever since he was a boy, and he didn't understand *why* he felt like that. As much as he tried to ignore it, the feelings never went away. He felt really bad about it, but it just wouldn't stop, try as he might.

In his mind, he felt it was wrong, and he was overcome with guilt every time he put on his wife's clothes. So he came upon an idea: what if he could find a way to do it, but make it so that it wasn't his fault? What if he was *made* to dress up? Then he could do it free of guilt.

That was when he started surfing the web, looking for a service run by a dominatrix. Tom had never really fooled around with control and domination, but it sounded perfect. He could find a domme to 'own' him, and in order to please her, she would turn him into a woman! It was a perfect plan. All of the pleasure, and none of the guilt.

 

* * *

 

Tom nervously read the issue of Playboy as he waited for his appointment with Karen. Her web site made it sound like she was just the perfect domme that he was looking for. After a brief chat on the phone, he decided to come down, and pay for her service. She had it set up that the name on the charge card would be something that sounded very innocent: J & H Postage Supplies. His wife Chrisy would never know what it was really for.

When it was his turn, he went in to the office, and sat on the couch. Karen walked in, and Tom was stunned by her good looks. She had long blonde hair, the face of an angel, and you would never believe that her job was to dominate men. She had on a choker with a flower shaped medallion around her neck, and a tight blue tank top with a scooped front that showed off her cleavage. There was no bra underneath, and you could clearly see the outlines of her nipples showing through.

Moving down with his eyes, Tom say her narrow waist, and gently flared out hips, giving her perfect curves. She wore tight blue jeans, slightly faded. Her arms looked so skinny, her wrists adorned with bracelets so slight, and her fingers long, delicate and fine. Her nails were painted a fiery red color.

She looked so girlish, so feminine. Her exterior hid all clues of her inner fierceness, and the power that she could wield over men. Tom had expected a chick in black leather or spandex, holding a whip, not a young woman who looked like a model or a TV star.

He looked up into her gray eyes, surrounded by gorgeous makeup. Her lips were pink with a frosty shimmer. Her cheeks so soft looking, with just a hint of pink blush. It was mesmerizing, staring into her face.

"Hello Tom" she said.

"Hello" he replied, holding out his hand to shake hers. He found himself trembling, and he didn't understand why.

"So, you are here because you want to be dominated" she said, boldly launching into the subject at hand.

"Yes" he replied quietly.

"And this is your first time, correct?"

Her voice was so soft and sweet. How could she be strong enough to tame him? Tom was suddenly filled with doubts.

"Yes. My first time."

"And when you become *mine*, you want for me to force you to dress up and act like a woman. Correct?"

She said it so matter-of-factly! How could she just treat his obsession as if it was something normal, like preferring Pepsi over coke, or something mundane? It shocked and excited him that she treated it with such indifference.

"Yes. I want you to turn me into a woman, by force" he said.

"And Tom, when you become a woman, what name do you prefer to use?"

"Um, I like to think of myself as Jenna."

He had never admitted that to anyone! But it came out so easily, as she asked the question, and wrote down his reply on her pad of paper. Now she set down the pad, and looked at him with her hypnotic eyes.

"We already discussed the pricing on the phone. You're still okay with it?" she said.

"Yes" he replied, his voice shaking with nervousness.

"And Tom, do you understand what you are getting yourself into? This isn't just a simple game, where you pretend that you're obeying me. I really am a dominatrix. If we enter into this agreement, I am going to *dominate* you, completely. I am going to *own* you, and make you do what *I* want. You will not be in control, at all. You are ceding all control of yourself to *me*. Do you understand that?"

"Yes" he replied weakly. "That's what I want."

"Sign here on the contract, to indicate that you understand."

Tom signed.

"And as part of your domination, I may have to use techniques where I tie you up, apply pain, or other methods of inducement, which may not be pleasant for you. I will determine how best to make you become my total slave, and you will have to endure whatever it is *I* decide. Do you understand? Initial by the X."

Tom initialed the form.

"Once you become *mine*, I own you, and you will obey me in all things. Again, this isn't a game, it is for real. You will be made to do things which you would never want to, because you will be serving only *me*. A total loss of control from yourself, and a total devotion to me. Do you understand and agree?"

"Yes" said Tom, signing on the form.

"Now I will give you one last and final chance to get up, walk away from me, with no strings attached. If you walk out that door, you are free to continue your life as you know it. Or, by your choice, and your very *last* choice I might add, you can sign on the final line, and you will become mine. Once you sign there, you cannot back out. Because that could only happen if you wanted to back out. But once you are mine, what you want doesn't matter. You will be completely mine, and you will do as I say."

Tom nodded.

"Think about it. Be very careful. This is your last warning. Go now, or sign the contract, and become mine."

With his hand shaking, Tom took the pen, and signed the contract.

"Carol, will you please come in here?" said Karen.

A secretary entered the room, dressed in a tight skirt. Her long red hair was worn up, and she had cute glasses on. But it was only after looking for a few moments that Tom noticed something: Carol wasn't a woman! She was a man! A man in a skirt, acting as Karen's secretary. All at once he felt thrilled to see the results of her work, and revolted, to think that he felt an attraction to Carol at first. Then he also felt something new: fear.

Carol moved like a woman. She sounded like a woman. She looked like a woman. But you could tell she was a man. What had Karen done to her in order to get her to act like that? And would that be forthcoming for him as well?

 

After Carol left, Karen turned to Tom.

"Take off all of your clothes, and get on your knees, slave" she said.

Tom was excited at this. He stripped, and got down on his knees, as she asked. His manhood was at full staff, showing his inner excitement.

"Repeat after me" said Karen in a much harsher tone than she had been using before. "I am a slave. I belong to Karen."

"I am a slave. I belong to Karen" said Tom.

"I have no will of my own. I will always do as Karen says."

He repeated her words. She made him swear that he was hers, completely. She made him say that he belonged to her, in every way. That he was hers to do with as she pleased. That he had no rights as her slave, and that his state was permanent. He could never back out; only Karen could sever their relationship.

Karen fastened a collar around his neck, and attached a leash.

"Come" she said. "Heel."

He walked behind her, as she pulled him by the leash. If he walked a step too slow, she gave the leash a yank.

"Look down at my feet, slave. Don't stare at my buns."

He kept his eyes down low, as she asked. She led him into a room which could only be described as a dungeon. There, she began to train him in earnest.

Tom had a ball gag put into his mouth. He was blinded. He was tied up. And Karen began to work on him, to break him down.

 

When the two hour session was over, Tom was a changed man. He hurt all over, and he was now deathly *afraid* of Karen. Instead of looking at her as some weak pretty thing, he now realized just how powerful she was. Just a word from her, and he would flinch, afraid of being hit again. When she ordered him onto his knees at the end of the session, he went down so fast and hard that it hurt.

"Now you are becoming obedient" she said. "Now you are starting to understand that you are *mine*. You will go home now, but you have homework. In your mind, and out loud when you are alone, you will say: 'I belong to Karen now. I am her slave. I do not matter; only Karen matters'. You will dream of me tonight."

With that, she left him, a quivering wreck on the floor. Carol came in, and handed Tom his clothes.

"Don't worry" said Carol. "She has to break you down before she can build you back up again. Karen wants you to return here on Thursday, at 8:00pm sharp."

"But I have plans with my wife" whispered Tom.

"Not anymore" said Carol, walking away.

 

* * *

 

Tom arrived right on time on Thursday. He did not want to be punished! Not after what she had done to him in the first session. Again, he was treated worse than a dog, tied up, humiliated and worse. This time, she made him cry.

When the session was over, he dared to ask her a question. So far, it had all been bondage, pain, and control. Nothing about dressing up. He was feeling frustrated from it.

"When will you start to turn me into a woman?" he said.

"Because you are new, this one time only I will not punish you severely for questioning me."

She slapped him hard on his raw behind, causing him to flinch with pain. After five more hard slaps, Tom was again in tears.

"You belong to *me*, slave. You will become a woman when *I* want you to become a woman. Not a moment before."

Tom was crying now, all out.

"And by the way, when we spoke on the phone, you said that you wanted to become a woman so you could be forced to clean, cook, and things like that. You need to understand something: you don't become a woman so that you can be weak. Being a woman means strength and power. It is *men* who are weak and worthless. Always remember that!"

She walked away, leaving him again feeling completely powerless. Carol helped dress him up, and told him that he was expected to return on Saturday night, at 9:30pm for his next appointment. He didn't bother to argue, even though he had dinner plans with Chrisy. He knew better than to do that.

 

* * *

 

Now it was Saturday, and Tom had been Karen's slave for three and a half days. He had been through two terrible sessions, where she had tortured him, and done terrible things to him. But the physical pain was nothing compared to the mental pain she was going to give him that night.

 

When Karen arrived, she made Tom undress. Then he was put into the leather collar, and nothing more. She led him to a room which looked like a bedroom. He wondered if she was finally going to dress him up. Maybe the clothes were hidden in the closet?

But it was not to be.

"Kneel down slave, in the corner there, facing the bed" she said.

Tom knelt, while Karen pushed a button on the intercom.

"Carol, please send her in" she said sweetly.

Karen smiled at Tom, and he wondered who was coming to see him. A makeup artist? Someone to help her dress him? He was going through a million exciting scenarios in his head. But then the door opened, and Chrisy walked into the room.

His wife! No! She mustn't know about this! Tom's eyes filled with sheer terror and panic. This was the worst thing in the world!

"Thank you for coming, Chrisy" said Karen. "As you can see, he is now very obedient to me, and he will not do *anything* unless I order it."

Tom felt so small, and whatever was left of his ego was being crushed down to nothing. But if he thought he felt bad at that moment, it was about to get even worse.

"Now you will show Chrisy just how much you are mine" said Karen.

Tom swallowed hard.

"Tom, tell your wife who you belong to now."

"I belong to Karen" he said, looking right into Chrisy's eyes. He knew any wrong answer would result in him being tortured again.

"And tell her what you are to me" she said.

"I am a slave" he replied.

"Very good Tom. So now your wife knows you are mine, and you are a slave to me. Now we will show her just how weak you are. We all know how women are the most powerful, followed by men, right?"

"Right" said Tom.

"But you're not even a man anymore, are you, *slave*? Tell your wife that you're not a man."

Tom looked right at Chrisy.

"I'm not a man anymore" he said to her, which caused her to nod solemnly.

"That's right Tom. You're not a man anymore. Not even that. Now tell me Tom, what does a wife do with her man in bed?"

"They make love" said Tom.

"Correct. But you're not even a man, are you?"

"No" he said.

"So you can't make love to her, can you? Tell her that you can't make love to her anymore, since you're not a man."

Tom looked up at Chrisy.

"I'm not a man, so I can't make love to you anymore" he said.

"That's right" replied Chrisy in a harsh voice. "I can see that you're not a man anymore. And I'd never allow you to sleep with me again."

Tom was devastated at this. It was one thing to hear it from Karen, but coming from his own wife, it was absolutely crushing.

"But Tom, you want your wife to be happy, don't you?"

"Yes" said Tom weakly.

"And to be happy, a woman needs a man to please her in bed, doesn't she?"

"Yes" he said.

"But we have a problem here. You're not a man anymore. So *you* can't make love to her anymore. But she needs to be with a man in bed to please her. So what is she going to have to do?" said Karen.

"Be with...with another man" whispered Tom.

"Exactly! You are very smart for a slave. Your wife needs a *real* man. Since you're not a man, she needs to be with someone else. Now slave, I want you to tell your wife that you want her to be happy, so you want her to be with another man in bed. Tell her you want her to start seeing other men."

"Chrisy" said Tom, as he trembled, and the tears started flowing again. "I want you to be happy. So I want you to be with another man in bed. I want you to start seeing other men."

"Yes Tom. I will start seeing other men. Men who can satisfy me, unlike you. Humph! You're not even a man."

Tom looked down, full of shame and tears. What had he gotten himself into?

"Now Tom, you are going to make your wife happy" said Karen.

She walked over to the intercom, and pressed the button.

"Carol, send him in" she said.

Tom's heart sunk as a tall handsome man walked into the room.

"Hello Karen" he said, kissing her on the cheek.

"Hello Tony" she said. "This is Chrisy, and on the floor, that is one of my slaves."

"Ah, another weak slave. He doesn't look like he's even a man. Just a weak little thing for Karen to play with."

"Now slave, you want your wife to be happy, right?" said Karen.

"Yes" whispered Tom.

"What? Louder please so we can all hear you."

"Yes" said Tom again, more strongly this time.

"And to make her happy, as we all know, she needs a man. A strong handsome man, like Tony."

Tony puffed up his chest, and struck a pose.

"Now slave, I want you to beg Tony to make your wife happy. I want you to beg him to make love to her."

Tom took a deep breath. He didn't know if he could do it, but when Karen raised her hand in a threatening manner, all of the pain training she had given him flooded his memories, and he would do anything to avoid her applying pain again.

"Tony, will you please make love to my wife?" he said.

"I don't know" said Tony. "What if I don't want to?"

"You need to convince him, or I'll be very upset at you" said Karen.

"Please, I'm begging you!" said Tom, in desperation. "Please make love to her!"

"All right, I will. She's pretty hot. I'd love to do her."

Chrisy took a step over to Tony, put her arms around him, and leaned towards him. Meanwhile, Tom almost collapsed as he deflated.

"Head up, slave" said Karen. "You need to watch, so you get to see how a real man pleases his woman. You will watch, and learn."

Tom had to stand there, and watch as Tony started kissing Chrisy, putting his hands all over her, and then watch as she responded by becoming aroused. She was breathing heavily as she reached down and unbuckled his belt, and unzipped his fly. He responded by pulling off her tank top, and then her bra.

Tony cupped her glorious breasts in his hands, and kissed her harder. Meanwhile, Tom was feeling lower than low. He was in a daze now, as they continued to get naked, and then get onto the bed. He watched in agony as Tony spread her legs apart, and penetrated her with his fully aroused manhood. Tom felt so bad, that he doubted whether he could ever have another erection himself. Karen was right. He *wasn't* a man anymore. He didn't feel like one. He felt like nothing.

 

After Tony had his way with Chrisy, she used her mouth to clean off his manhood, then licked her lips.

"Mmm, so big and strong. And so big inside me!" she said, snuggling up against him.

"Slave, you can see that your wife is very happy now" said Karen. "I command you that when you go home with her, you are to do two things. Number one, you are to serve her as you serve me. Since you now know that you aren't even a man, you are only fit to serve a woman. You will be her slave, as you are mine."

Tom looked helplessly at her.

"And number two, your wife needs to be kept happy. You will encourage her to see other men. You will invite them over yourself if she asks you. And you will watch as you did tonight. It is important to me that you watch as other men make love to your wife. Do you understand?"

"Yes" said Tom.

"Then tell me what you will be doing."

"I will serve Chrisy as I serve you. And I will encourage her to see other men. I will watch as they make love to her."

"Excellent. You are a good slave" said Karen. "Now you will go get dressed up, and return home."

"What about Chrisy?"

"Tony is going to take her out to dinner, along with me. You can sit at home alone, and imagine the fun we are having. He is a *man*, so he'll treat us. Who knows, he might get aroused again, and she might need to go into the men's room with him, in order to please him. You can sit home alone, and think about that. Unless Chrisy has any orders for you?"

"Well, in fact, it would be lovely if he did some cleaning" said Chrisy.

"Very well. He's your slave now too. Order him to do it."

"Slave, when you arrive home, you will vacuum all the rugs, and dust all of the rooms" said Chrisy.

"But remember, you are not privileged enough to be a woman, so you need to do it wearing your man-clothes. No maid fantasies for you, slave."

 

As Tom dusted off the collectibles on the shelf in the livingroom, the tears started flowing again. Chrisy was out with another man, having fun. He was stuck being her slave, doing housework. And he had been ordered to stay dressed as a man! This was the worst possible thing he could think of.

 

* * *

 

Karen waited for three months before calling Tom in for his next session. During that time, he had to watch a dozen different men come into his house, and make love to his wife. Three months of it! He was beyond crushed. And Chrisy had taken over full control of him, as her slave. It was only her *order* to him that kept him from wanting to end his own life. He was in solid misery all day, every day.

He was full of dread as they arrived back at Karen's offices. What new torture would she have for him today? He was so frightened of her! She could hurt him with pain, but what she had done to him psychologically was a million times worse.

Again, he was thrown a curveball with what he was forced to endure that day, and he had no idea at all why he was made to do it. He was sat down in a chair, and tied up by Chrisy and Karen. Then he was gagged, and positioned by the side of the bed, very close.

"Now slave, you will watch closely, and learn" said Karen.

She turned to Chrisy. Much to Tom's surprise, they hugged each other, and kissed! The started to touch each other tenderly! And before he realized what was going on, they started to remove each other's clothes! When Chrisy removed Karen's bra, she started to suck on her nipple, and Tom's mind was blown.

Once they were naked, then got on the bed, and started licking each other between the legs. They used their fingers inserted into each other's pussies. And they used a sex toy shaped like a man's anatomy, except that it had two heads on it. With one head inside each of them, they brought each other to climax at the same time.

Tom was in agony. He had been cut off from having sex for a *long* time now. He wanted his wife so bad, and he wanted Karen. Now they were in bed with each other, and all he could do was to watch! More than anything, he wanted to be in that bed with them, and have them make him come. But that wasn't going to happen.

After the girls were done, they snuggled and kissed. Then Karen got up, and removed the gag from Tom. Chrisy walked over to him, with the sex toy still stuck half up inside her. She kept getting closer and closer to Tom, with it pointing at him.

"Suck" ordered Karen.

Tom opened wide, as she rammed it into his mouth. It stuck out of her, and now into his mouth. She rocked back and forth, forcing it in and out. He could taste the juice from Karen's pussy on it, but the shape was absolutely horrifying to him. He started bug-eyed, as Chrisy worked him with it.

As she continued with him, Karen loosened the bonds on his feet. She forced them together, then started to pull something up his legs. Then she undid the bonds on his arms.

"Get on your knees. Keep sucking" she said.

He did it, and she pulled up the rest of the way the thing she had been working up his legs.

"Now you're in panties" she said.

Tom felt them, so soft, against his skin. He had worn them before, but never like this! They had never been *forced* on him before, and now when he was in a position like he was at that moment. Somehow, they made him feel *weak*. They encased him, and made him feel even less of a man, if possible.

Tom kept sucking, as she started to put something onto his chest. He could feel it. A bra. As Chrisy continued with him, she fastened it on him, and stuffed the cups full with breast forms.

"Now you've got boobs. You will *always* wear panties and a bra from now on, at all times. I command it."

"And I command it" said Chrisy, as she thrust forward yet again. "Now use your hands, take that out of me, and keep sucking."

Tom did as ordered.

"Now you will start becoming a woman" said Karen.

Tom had dreamed of this moment for so long! It would be fun. It would be glorious. A triumph. He would be turned on, he would come so hard. But instead, he felt so empty now. He was being *forced* into something he didn't want. He just wanted to end it all, and to get away. But he was stuck as a slave now, and they were doing something to him he didn't want to do. He was weak. He was nothing.

To make matters worse, Karen called Carol on the intercom, and in a few moments, another person entered the room: a tall muscular man. Chrisy spread her legs wide open, as he pulled his pants off. Moments later, he was on top of her, and she was moaning with pleasure.

Tom wanted to cry. Here he was, stuck in a stuffed bra, wearing panties, on his knees, sucking a sex toy, while his wife was again making love with another man. Karen walked up to him, and blew into his ear. She touched him lightly on the chest, then worked her hand down to his crotch. He could feel her breasts pressing against him. His body ached for lovemaking so bad, he got hard right away. Karen kept rubbing him, as she whispered into his ear.

"Keep sucking. Yes, that's good. Now watch your wife on the bed. She how a woman makes love. Now sit down, and spread your legs wide apart, like hers are."

Tom was thankful to get off his knees. He sat down, and spread his legs. He couldn't see Chrisy as well now, but the bed was low enough for him to get a good view of the man.

"See how she enjoys it" whispered Karen into his ear, as she gave him a gentle kiss. "Imagine that you are her. Imagine how she feels as her man pumps her. Imagine that he's doing that to you, and you are the one on the bottom. Feel what she feels. Imagine your pussy, and how it feels to make love with it. You are her now. You're feeling what she's feeling. Her desires are your desires. That is you on the bed, on the bottom. Feel it *Jenna*."

It was the first time that she had used the female name that he had told her about. As much as he was in agony, as much as he hated what he was seeing and feeling, his body couldn't help it. The stimulation was too much. Although he tried to hold back, he exploded, and came into his panties.

"Ooh Jenna, you just had an orgasm!" said Karen proudly. "I guess he really turned you on! You imagined that he was pumping you, and you came! Your first feminine reaction. You *are* becoming a woman."

 

Tom was stunned. This wasn't what he was supposed to feel! This was terrible! Somehow, he now felt even *more* under Karen's control than ever before. He was hyperaware of the bra he was wearing, and the wetness in his panties.

"Remember Jenna, you are going to *always* wear panties now, and you are *always* going to wear a bra, with your breast forms. Even at home. Even at work. Even if you go visit your parents. You are becoming a woman now, and you cannot go around unless you are properly dressed."

 

Tom watched as the man got off of Chrisy. She kissed him, as he pulled away, got dressed, and left. Before he walked out the door, he looked Tom in the eye, and smirked.

"Now that its just us girls here" said Karen, "we can discuss a few more things."

"Oh, what's that?" asked Chrisy, as she used a Kleenex to wipe herself off between the legs.

"Feminine hygiene. I'm afraid that poor Jenna here didn't learn very much from her mother, so you are going to need to help her Chrisy. When she reports here tomorrow, I expect for her to be rid of all that nasty body hair, and for her to shave her legs like a good girl."

"Yes, I agree. It looks disgusting" said Chrisy.

"And dear, if you could help her pluck her eyebrows. They are so bushy, and such a mess. And those nails! She needs to start growing them long, but you could help her file them, and perhaps paint them a nice pink color to start out with."

"Very good" said Chrisy.

As Karen listed the things that she needed to do to him, he felt dread instead of the joy he expected. He couldn't go around with painted nails!

"And then take her to the mall, get her ears pierced, and pick out something pretty for her to wear. Then while you're there, you can buy her the supply of panties she'll need, and some bras. I've made her a C cup for now, but I might go up a size, because her shoulders are a little to big."

"Anything else? Should I get her some skirts?"

"Not yet. She needs to *believe* on the inside that she is a woman, before she is ready to wear the right clothes. Today, we started with a few superficial things. But as her mental state progresses, she will earn the right to wear high heels, skirts, blouses, and the rest."

"Sounds good" said Chrisy.

Tom was hearing all this, and wondering what he could do to get out of it. He couldn't go into work with pierced ears, painted nails, not to mention a stuffed bra under his shirt! He hated how they were talking about him, as if he wasn't even there.

"Remember" said Karen turning to him, "you aren't a woman yet, so you are still a slave. After today, I don't think that even you can believe that you're a man. Today, we have made you completely sexless. Now it is your job to earn your womanhood. As you progress, we will give you more and more freedom. But to earn it, you will need to prove to us that you think of yourself as a woman. You will need to demonstrate that you have feminine thoughts, feelings, and desires. When you make me believe that you really are a woman in your heart, on that day, you will be free."

 

Tom went home with Chrisy, without speaking a word in the car. He was afraid to say anything. All he knew was that things had gone from bad to worse.

 

* * *

 

It was a warm day, so when they headed for the mall, Chrisy insisted that Tom (or Jenna as she called him now) needed to wear shorts instead of jeans. Then she said that the bulky sweatshirt he had on needed to go as well. She handed him a plain white T-shirt to wear instead. He obeyed her. He had to.

Tom felt *so* self-conscious walking through the mall. His legs were freshly shaved, and he could still smell the rose scent from the bath oil. Worse than that, you could clearly see his bra beneath the thin cotton fabric of his T-shirt. Just as Karen instructed, they first went to the jewelry store, to get his ears pierced.

The girl tried to pretend that everything was normal, as she helped Chrisy select a pair of pretty silver hoop earrings, over two inches in diameter. But she kept staring at Tom's chest, making him feel incredibly uncomfortable.

"Would you like to wear these home, or should I just bag them up" she said to Chrisy.

"Oh, they're not for me. They're for my husband" she replied, pointing to Tom. "We need to get his ears pierced, and then he will wear them home."

"Okay..." she replied.

Tom blushed bright red. Did she have to be so blunt about it? She said it as if she was buying a loaf of bread or something, not helping to turn her husband into a woman! And did the earrings need to be so flashy, so long and dangling? With his short hair, they were so easy to see!

With a little pinprick of pain, he now had one pierced ear. And then another. He looked at himself in the mirror, and could not believe that he was wearing earrings!

 

Now Chrisy took him to a lingerie store, and helped him pick out panties. Some where white cotton, some were in different colors, some had lacy trim, some where shiny and glossy looking. One pair were thongs. It was all very scary for Tom to think of wearing them!

"We need some matching bras" she told the saleswoman.

"What size do you wear dear?" she replied.

"They're for him" she said, pointing to Tom. "He has never been properly fitted for a bra. Would you please help him?"

"Certainly" she said, although there was clearly some trepidation in her voice.

Tom stood behind the screen, as she started to measure him up, and explain what the cup size and the band size of a bra were. With his proper size written down on paper, he met up with Chrisy again, who helped him pick out several colors of bras to go with the panties.

Tom thought they were done now, but it wasn't to be. Chrisy now marched him over to the nail salon, and asked how long of a wait it would be for a manicure.

"Oh, about fifteen or twenty minutes" said the girl behind the counter. "What's your name?"

"Jenna" said Chrisy, as the girl wrote it down.

Tom and Chrisy sat down in the chairs. She handed him a copy of Glamour, and told him to read it while they waited. He felt like every woman who walked into the place was staring at him. It was almost a relief when the receptionist called out "Jenna? We're ready for you now."

Tom and Chrisy both got up. The girl pointed them to a woman in a white coat who was waiting for them. She turned to Chrisy and said: "Hello Jenna. I'm Alicia."

"I'm Chrisy" she replied. "This is Jenna."

"Oh sorry" said Alicia, who seemed very confused now as she looked Tom up and down.

"Jenna needs a manicure, but she has never got a manicure before. Help her pick out a pretty color, perhaps something in a light pink?"

"Sounds good" said Alicia, who guided a helpless Tom back to her station, so she could start on his nails.

 

 

When Tom returned to the waiting area, his nails looked very different. They were a bright pink color, with a very shiny clear coat finish on top. He was holding a slip of paper which had the name of the color written on it: "Strawberry Flirtation". Chrisy paid for the manicure, and a bottle of the nailpolish, so he'd have some for touchups.

Now as he walked through the mall, Tom felt even worse. Shaved legs. Stuffed bra. Dangling earrings. Plucked eyebrows. Painted nails. He had a man's body, but more and more outward symbols of femininity. How in the world could he go to work like that tomorrow? He would never be able to hide all of the things that Chrisy and Karen had done to him. Everyone would see him and know. There was no way to avoid it. He would be found out tomorrow, by every single person in his office.

 

* * *

 

Tom racked his brain that night, as he watched the movie with Chrisy, on the couch. He had to work. He needed the money. He *could* call in sick, but this wasn't going to go away. One way or another, he was going to have to expose his life to his coworkers.

When the movie was done, Chrisy turned to him.

"Karen told me to tell you something" she said.

"What's that?" he replied.

"She has hidden cameras in the bedroom. She has lots of pictures of you, sucking your sex toy, wearing your bra and panties. She said that if you don't go into work tomorrow, she will be forced to e-mail them to your parents, your brother, your boss, and the local newspaper. So I think you *have* to go to work tomorrow, whether you want to or not."

Tom almost wanted to cry now. He had been dreading this, thinking about it all evening. He had an idea, but he kept trying to put it out of his head. But he saw no other way. He had to try it. There was nothing else.

"I want you to teach me how to put on makeup" said Tom.

"Right now?" asked Chrisy.

"Yes. I'll need it to wear into the office tomorrow."

"Are you sure?" said Chrisy.

"Yes. Karen said I can't wear a skirt yet, but she didn't say I couldn't have makeup. So teach me now."

Chrisy took him by the hand, led him upstairs, sat him down at the vanity, and began her lesson.

 

* * *

 

In the morning, Tom showered. He shaved his legs, underarms, and double checked to see if his chest needed it too. He lathered up his pubic hair, and started to shave it as well, until there was only a thin strip of hair in the middle. Then he dried off, and put on his bra and panties. He picked the pink bra with the ruffled edge along the top, and the matching shiny silky pink panties. He slid in his breast forms, then went to pick out an outfit.

Among his man-clothes, there were mainly just dull dark colors for work. He chose the black pants, and a white button-down shirt. He skipped his usual undershirt, because he wanted to be sure that the bra showed through the shirt as much as possible.

Then he sat down at the vanity, and started with his makeup. He put on a thick base of foundation, to help hide his hair follicles. He applied makeup to his eyes to make them look deep, sexy, and alluring, including very long eyelashes, covered with mascara. He liked how the frosty blue looked on his eyes too. Then he accentuated his newly thinned eyebrows. Pink lip gloss on the lips, and gentle blush on the cheeks. A spray of perfume, and he was all set.

Instead of his usual black socks, he put on knee-high nylons, and then his boat shoes. He put hair gel in, and did his best to make it look spiky, instead of laying flat as it normally did. Anything to give it some volume. He went into the walk-in closet, and picked out one of Chrisy's old purses. He put his wallet into it, and his keys.

Next, he dug out a tie that he had seen Chrisy wear once. Instead of man's tie, which had a knot at the top and the part hanging down the middle, this one went into a kind of a bow. It looked very girly and feminine. Perfect.

 

"Well well, look at you!" said Chrisy as she looked up from the morning newspaper. "You look very pretty. Are you sure you want to go into work like that Jenna?"

"I can't hide the fact I'm becoming a woman" said Tom. "So I might as well really show them what I am now. I am going to march right into my bosses office, and tell him to start the paperwork to change my official gender. I'm going to tell everyone to start treating me like a girl at work."

"I'm very proud of you" said Chrisy, giving him a peck on the cheek. It was the most affection she had shown Tom in months, and his heart just melted from it.

 

"He did it! Just like you said he would" she said to Karen on the phone. "Yes. I'll make sure we go there right after dinner. Thanks so much!"

Chrisy hung up the phone, and shook her head. Karen was amazing.

 

* * *

 

Tom walked out of the office building, and he was just shaking. It had been *so* hard to walk in that morning, and tell the boss that he wanted to be called 'Jenna' from now on. And to face his coworkers in meetings, and act like nothing was wrong. They all stared at him, and all day long he heard the whispered rumors. He was called every name in the book. But he didn't care. Now it was out in the open. He couldn't hide what was happening to him, so now there would be no more sneaking around. Now everyone knew.

He was very surprised though, to see Chrisy waiting for him at the curbside, in her minivan. He got in, and she drove over to a nice restaurant. As they ate dinner, she gave him a couple of gifts: a diamond bracelet, and a necklace with a heart shaped pendant. He put them on and smiled. They were very pretty.

After diner, they drove again, and Tom wasn't all that surprised to see them pull up to Karen's office. Then went inside, and met Karen herself in her office.

"Well Jenna, let me start out by saying that I am very proud of you. It is so wonderful that you have decided to share your femininity with the world. That tells me that you have accepted it, and you are ready to proceed to the next level."

Tom nodded and looked back at her.

"Show her" said Chrisy.

Karen smiled, and led them back to the bedroom. There was an outfit laid out on the bed.

"Go ahead, put it on" said Karen.

Tom stripped down to his bra and panties. First, he put on the girdle, which was very tight, but helped shape him to a more feminine figure. Then there was a black garter belt He put it on, the pulled the black nylons onto his legs, attaching them to the garter. Next, there was a white slip, which he put on. Then the tight blue pinstriped skirt came next. It was very form fitting, and hugged the curves the girdle seemed to give him. Now he put on a tight white blouse, very sheer and see-through. It was very poofy in the arms, with frilly lacy cuffs and trim. Last was a jacket that matched the skirt: dark blue and pinstriped, but cut to fit a woman. Now he looked like one of the secretaries at the office.

"Here are your shoes, dear" said Karen, handing him a pair of heels. The heels seemed so tall and so thin! How could he put them on, and stand up? He was about to find out, as Chrisy helped fasten them onto his feet. He took some tentative steps, and it took some practice before he could move comfortably without grabbing on to the wall or the bed to keep his balance.

"Because you have showed me that you think of yourself as a woman" said Karen, "you have earned the right to wear skirts. In fact, I insist, as your friend, that you really ought to *always* wear skirts and dresses, to show off your femininity better."

It wasn't an order. It wasn't a command. It was a suggestion, as a friend! Now in a skirt, for the first time in months, Tom felt just the slightest sense of power again over his own life. Karen's words from long ago echoed in the back of his mind: the more he became a woman, the more he would become free.

"I have a test for you now" she said. "I want to measure your progress."

She called Carol, who came in with a tray. On the tray was a set of fancy tea cups, steaming with hot tea. There was a sugar bowl as well. But when Karen removed the top of the sugar bowl, it held little white oval pills, instead of sugar.

"Pure estrogen" she said. "The female sex hormone. To a man, these would be frightening to think of taking, because they would make him start to grow real boobs, lose his ability to perform in bed as a man, and rewire his brain, among other things. But to a woman; this is what is *supposed* to be flowing in her bloodstream. A woman knows that this is something natural in her body."

"But your body is defective Jenna. You have a birth defect in your female body, and you lack the mechanisms to naturally produce this. Your body *craves* estrogen. Your breasts can't wait to begin growing out, so you can naturally fill out your bra. Your skin longs to be soft and smooth. Your brain is aching to be rewired so that you will start to think as the female that nature intended you to be."

"You want me to take some of those" said Tom.

"Jenna, I *know* that you are going to take some" said Karen. "The question is: how many will you take? Each pill holds the amount of hormones that a woman naturally produces in one day. But your system is way behind, starving for estrogen. So the question again is: how many pills are you going to take? Ten day's worth? A months worth? All of them?"

Tom looked at the pills in the sugar bowl. He *wanted* them. They would help really make him a woman, and move him closer to being free. He grabbed a handful, and began to take them with his tea. Karen, Chrisy and Carol all chatted with him, as they drank their tea. He needed a second, then a third cup, in order to wash down all of the pills he had grabbed.

"Carol, go get Jenna a prescription" she said.

After Carol left the room, Karen turned to Tom.

"Before Carol came to me, she was a man. She was a doctor. Now she is my secretary, by her choice. But she still has her medical license, and she can write prescriptions. She is writing out two of them for you right now: one for female hormone replacement therapy, and one for birth control. Birth control pills contain female hormones as well, the ones that tell your body that you're pregnant. They'll really help with your boobs, and your skin. You'll soon have the glow of an expecting mother."

Carol returned with the two slips of paper, which Karen handed to Tom.

 

"Chrisy, why don't you take Jenna shopping tomorrow, and buy her some nice pretty things of her own? She needs dresses, skirts, blouses, camis, pantyhose, heels, flats...a whole new wardrobe."

"That sounds fun!" said Chrisy. "I can help teach her about how to put an outfit together."

"And one more thing for you to do, when you get home."

She turned and whispered something into Chrisy's ear. Chrisy giggled, then Karen giggled too. Tom couldn't wait to find out what it was.

 

 

Later that night, when they were home, Chrisy and Tom undressed. She gave Tom one of her old nighties to wear. And much to his surprise, she invited him into the bed with her. He had been sleeping on the couch for months! This was his first time in bed with her since the second session with Karen, when she had brought Chrisy in to get involved.

As they laid down, Chrisy kept telling Tom how pretty he was, and what a wonderful woman he made.

"Karen said that thing between your legs won't work for very much longer. So I'm supposed to do something with it tonight, while I still can."

She rubbed him between the legs, getting him aroused. Then she spread his legs apart. She moved around to face him, then straddled him. She guided his stiff manhood into her warm inviting slit between her legs, and she lowered herself onto him.

"You saw how Karen and I made love" she said. "That's what you and I are doing now. You don't have anything between your legs anymore. What you feel, is a sex toy that we are sharing. You feel it penetrating deep inside your pussy. You are a woman now Jenna. You are female. You have a pussy, and you love how it feels when your lover fills it with a hard shaft, like I'm doing now."

She moved up and down, stimulating him more. She kept telling him how he was a girl now, and how she was putting it to him. He laid there, breathing hard, as she kept going at it.

"Soon, you'll have real boobs of your own, Bigger than mine. Look at my chest. Very soon, you're going to be just like this. *Feel* your boobs, as they grow out. With all the estrogen in your system, they're growing already. You're a woman Jenna. You are female now."

Soon after, Tom exploded inside of Chrisy. It was the first time he had made love to her in months, and he was *so* much in love with her now, and on the verge of tears. But they were tears of joy. She loved him again!

"Karen turned me into a lesbian" she said, as she lowered herself on him, and kissed his cheek. "I'll never sleep with a man again. I'll only sleep with girls. And Jenna, you are the only girl for me."

"I love you" said Tom. "With all my heart, as long as I live, I love you, and I will treasure every moment that we are together."

"I love you too Jenna" said Chrisy, as she settled down next to him, and snuggled close.

For the first time in his life, Tom really opened up, and talked to her about his feelings. By the time whey went to sleep, Chrisy was as much in love with him as she had ever been in her life.

 

* * *

 

"Karen, I just want to thank you again for all you did" said Chrisy. "I can't believe how my relationship with Tom has changed so much! He *talks* to me now, he doesn't mind helping out with the housework, he wants to spend *every* waking moment with me, he loves doing all the things that *I* love, even shopping and chatting with girlfriends! He is perfect now. All thanks to you."

"And you as well" said Karen. "You certainly did a great job playing your role."

"Yes, but you're such a genius" said Chrisy. "You have him convinced that he's on female hormones! He believes his boobs are growing that that he's becoming more and more female by the day. But they're just vitamins! I can't believe you got him to fall for that!"

"Well, if he really was on hormones, he'd lose his ability to perform in bed. And we can't have that, can we?"

"No way" said Chrisy. "And now, I always get to be on top. I get more stimulation that way, and he never complains because he gets to 'be' the woman. He really thinks you turned me into a lesbian too!"

"Have you thought about using a strap-on with him? Just every now and then, to help remind him of what he has become."

"I bought one, but I haven't used it on him yet, because he is still acting so good. But any slippage on his part, and I'll pull it out."

"Very good" said Karen, taking a sip of her tea. "Now there is another reason I asked you here today, other than to check on Jenna's progress. You see, there is another man who just came to me, and I need to convince his wife to help out. As you saw with your Jenna, if the wife helps out, I can crush a man in just days. Without her, it would take me months or even a year. But I want fast results. Would you be willing to speak to her, and tell her about the benefits you got from having Tom turned into Jenna?"

"Karen, don't be silly. Of *course* I'd be glad to talk to her. I'm just sorry that you didn't get your hands on Tom sooner. All those years I suffered with him acting like a typical guy! Now he's perfect, and it's all thanks to you. What's her number? Let me call."

 

Karen smiled as Chrisy told the woman on the phone how wonderful Jenna had become. Just a few months ago, it had been an unbelieving Chrisy on the phone, talking with Susan, who's husband had been recently turned into a woman named Monica. Now Chrisy was convincing another woman, and the cycle was complete. Soon, there would be one more feminzied man in the world, as soon as Chrisy got off the phone, and the wife came in to Karen's offices, to learn of her role in the plan. Her husband would become a woman much sooner than the wife would even think possible.

  

  

  

*********************************************
© 2004 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.