Tommy Boy

by Jennifer White

 

When Tommy's parents came home early from a dinner party at a friend's house, his mothers worst suspicions were confirmed. Of late, it had seemed to her that things in her dresser were out of order, and messier then she had left them. She put things away nicely, but the next day, there was disorder where once everything had been tidy.

Or there was the incident where her light blue bra disappeared for a week, then suddenly, it reappeared in her dresser drawer. There was no way she could have missed it with it's distinctive color. Her husband, Jack, had been out of town for the week on business when this all happened, so he couldn't have done it. So that left one suspect: Tommy.

She thought it might just be a stage. Now that he was getting older, and starting to mature sexually, perhaps his interest in all things female was peaking. She remembered from her school days, how the boys only seemed to have one thing on their minds all the time: sex. And so she ignored it for a while. But it kept happening.

 

She tried a few things, like leaving a note in her dresser drawer that read "for girls only". That only seemed to excite him more instead of deterring him. She was at her wit's end, and finally told her husband Jack, the boy's father. He of course was enraged, and swore it would never happen again. But it did.

And this time, as they walked in the door hours early, they found Tommy sitting on the couch, watching TV, wearing one of his mother's skirts, a silky blouse, under which was a one of her bras, stuffed full.

 

"You've even got makeup on!" stormed Jack.

"Tommy! You and your father had a talk! You promised not to do this again!"

 

The boy burst into tears, and ran into his room. This was the first time he had been caught red-handed, and the first time that anyone had seen him dressed up like a girl. He ran in shame into his room, slammed the door closed, and locked it.

 

* * *

 

Enough was enough. Jack decided that it was time to take action.

"This isn't just some phase" he said. "If we don't do something soon, our son is going to end up as a sissy. He's going around wearing your clothes! We can't let this continue. He needs to be broken of his habit, before it is too late."

"You're right" said Sue, concerned about what Jack might do to him now. "But we need someone who is an expert. We don't know how to make him stop."

"I agree" said Jack. "I found someone in the phone book. I'll make an appointment for this afternoon, and we'll bring Tommy in to see them."

"Thank you" said Sue, hugging her husband. "I was afraid you'd beat the boy or something."

"I want to" said Jack, still seething. "But he needs something more. We'll let the experts have a try at him."

 

* * *

 

And so it was that Tommy was dropped off at The Castle Clinic, a private facility run by Dr. Cynthia Castle. She spoke with Jack and Sue, as they recounted the details of Tommy's history of dressing up, and what the problem was all about. She was professional, understanding, and she reassured them.

 

"I've seen situations like this many times. There is nothing wrong with your son. It happens quite frequently in fact. We'll enter him into our program here, and in two weeks, you can pick him up, and he will have moved beyond his little stage of dressing up."

"Thank you doctor" said Jack and Sue, almost in unison, causing everyone to laugh. Sue went out to get Tommy, who was pouting in the waiting area, his arms crossed.

 

"I don't need to see a doctor!" he said.

"Tommy, please don't make a scene" said Sue.

"I'm not going in there! You're going to try to change me, and I'm not going to do it!"

 

"Tommy, listen to your mother!" said Jack, his temper flaring again.

"What? Are you going to hit me? Go ahead. It won't make a difference" said Tommy.

 

"Are you Tommy?" said a sweet voice, causing the boy to look up. There, standing before him was a beautiful nurse, wearing a tight white outfit. Her face was so sweet and pure, her hair long and blonde. On top of all that, she was quite busty, and the buttons at the top of her white coat seemed to strain, as if they were about to pop off.

 

"Come with me" she said. "Please?"

 

Tommy was in awe of her. Ignoring his parents, he followed the nurse down the hallway, and into a room.

 

"See?" said Sue. "He *does* like girls. We have nothing to worry about."

"I just hope that Dr. Castle is as good as she sounds. I want my son back, *normal*" he said, still in a huff.

 

Sue and Jack returned to their car, and drove home for two weeks of peace, as their son was "cured" at The Castle Clinic.

 

* * *

 

"Do you know why you're here?" asked the redheaded woman doctor.

"Yes" said Tommy. He knew, but he wasn't going talk about it. Dressing up was something he did in private. He didn't need or want to tell anyone about it. He swore to himself that he'd never stop doing it. He enjoyed it too much, and nothing make him feel more like himself, as when he was dress up as a girl. He had even worn a pair of panties under his jeans that day, just as act of defiance. He had bought them all on his own, at the mall.

 

"Are you really serious about wanting to be a girl?" she asked. Not in a way to shame him; not in a way to embarrass him. It was more like his medical doctor asking if he hurt when he coughed

"Yes I am" he said. "I like to dress up, and you can't stop me."

"Oh, I'm not going to stop you" she said, reassuringly. "Now tell me, if you are so serious, do you have anything on *now* that would prove yourself?"

"I have my pink panties on" said Tommy, surprised that he actually told her. She seemed so non-threatening, and so gentle about things, that somehow he felt comfortable enough to tell her. She smiled, and wrote a note on the pad of paper she held in her hand.

"That's nice" she said, smiling. "I can see that *you* are serious. I think you'll find your stay here quite enjoyable."

 

Tommy was puzzled. His parents had told him they were taking him somewhere to break him of his 'habit' as they called it. He thought he'd be punished or tortured. Not treated nicely. He didn't know what was going on.

 

"Tommy. Not an appropriate name for a girl, is it?" asked the doctor.

"No" he said.

"What is your *real* name?" she asked.

"Tommy" he said.

"No. I mean, when you're a girl. What is your name?"

"Oh. Tina. I'm Tina when I'm all dressed up."

"Tell me Tina, how long have you been dressing up?"

"Since I can remember" he said. Nobody had ever called him Tina before! It felt so good!

 

"Now Tina, my assistant Kate brought you in here from the waiting room. She's quite an attractive girl, don't you think?"

"Oh yes, very much so!" he said.

"When you see her, what do you want? Do you want to have sex with her? Or do you want to *be* her?"

 

Tommy was all excited. For some reason, he even got aroused at the thought of *being* a girl.

"I want to be her" he said.

 

"That is wonderful!" said Dr. Castle. She smiled as she wrote some final notes. "I'm so glad that you're going to stay with us here Tina. You're one lucky girl, with all that you have in store for you."

 

She called him a girl! This *was* like a dream come true for him, more and more!

 

"Kate, can you come get Tina, and help her get dressed?" said Dr. Castle over the intercom.

"Sure thing Dr. Castle. I'll be right there to help her" replied Kate in her soft, lovely voice.

They had both referred to him as 'her' again. Fabulous!

 

"Your legs are already shaved, right?" asked Dr. Castle. She sounded as if she'd be disappointed if he didn't

"Of course" he replied. "And my chest & armpits too."

"Good girl" she replied, as Kate walked in the door.

 

Kate took Tommy by the hand, and led him down the hall, down the stairway, and into a room. She locked the door, opened up a closet, and smiled.

"Please take all of your clothes off, Tina" she said.

"Why?" asked Tommy suspiciously.

"Because they are *boy's* clothes. You can't go around here dressed up like a boy, when you're a girl, can you?"

"No!" he said, suddenly filled with enthusiasm. He removed everything but his panties, and stood there in front of Kate. She took out a tape measure, and wrapped it around his chest, took the length of his arms, his legs, his waist, and more. She wrote them all down on a pad of paper, and then she turned to the closet.

 

"Lie down on the examining table" she said.

It was just like the kind in a doctor's office. Tommy laid down, as she had requested.

 

"First, we'll fit you with breast forms" she said. "These are c-cup sized, so they might take some getting used to. I assume you stuff your bra, but these will be like a part of you. I'm applying a glue which will hold them close to your skin, until the top layer starts to flake away. You'll need to re-glue them on every few days. Be sure to wash them carefully, and take good care of them. They're your boobs, until you grow your own *real* ones. You are not to be seen here, without boobs on your chest. Do you understand me?"

 

Tommy nodded enthusiastically. He could hardly believe it! She was gluing realistic looking boobs onto his chest! And he *had* wear them all the time! He held them with his hands as the glue dried. And she said that he was going to have *real* ones of his own! That was so exciting, that he felt himself get all hard, which was quite embarrassing, with Kate looking on.

 

"I'm sorry" he said, feeling ashamed that his body would betray him like that.

"It's not a problem dear" she replied. "Your little bitty thingie is so small, that I hardly notice it. Yes, it is a little big for a girl, but you're definitely not a boy. Not if you're *that* small. I'd have never even seen it, if you hadn't pointed it out. I can see why you think of yourself as a girl."

 

Somehow, her words made him go soft, which was a relief to him.

 

"Okay Tina. The glue should be all set in place now. Stand up, and check out your new boobs in the mirror."

 

Tommy sat up, and felt the weight of the silicon gel mounds affixed to his chest. He went over to the mirror, and smiled as he saw himself. They looked so real! As he stood there, Kate held out a bra for him. He put his arms through the loops of the straps, and she slid it onto him, fastening it in back.

 

"I expect for you to be wearing a bra at all time, except for when you're in the shower. Is that understood?" she asked.

"Yes Ma'am!" he replied, overjoyed at *that* rule.

Next, she handed him a red plaid skirt, that didn't even come down to his knees. He gladly put it on, followed by the white blouse that she handed him. She showed him how to tie a thin black tie into a bow. And then she handed him a pair of knee-high white socks. The shoes for the outfit only had a little bit of heel, which was a disappointment. But no matter; he was dressed up as a schoolgirl now, and he loved it!

 

Kate presented him with a cosmetics case, and helped him put on his makeup. She then showed him how he could style his longish hair into a style that was more feminine than how he wore it.

 

"As you let it grow out long, you can do more with it" she said, as he started to paint his nails. When the polish was dry, she placed a couple of rings onto his fingers, gave him a necklace, a girl's watch, and bracelets. She sprayed him with perfume, and had him examine himself in the mirror.

 

"You look very pretty Tina" she said.

"Thank you" he said, hardly believing his eyes. This was by far the best he had ever looked. He looked just like a girl now! He was so happy that he wanted to cry, but he didn't want to ruin his eye makeup.

 

"You are Tina now" said Kate. "And you are a girl. You can stay with us here, as a girl, for as long as you would like. But we do have rules. One of which is: you must *act* like a girl at all times. If we catch you pretending to be a boy, even for a few moments, you will be expelled."

"I won't" he said. "I promise!"

"Everyone else here, from Doctor Castle, to myself, to the others, are all real girls. You are the only person here without ovaries. But as long as you behave properly, as far as we're concerned, you *are* a girl. We won't tell anyone about you. But if for *any* reason, any person finds out you're not a girl, then you are expelled. I don't care how it happens; if even one girl suspects that you're not female, you're gone. Understand?"

"Yes Ma'am!" said Tommy. "I promise. Nobody will know I'm a boy. They'll all think I'm a girl."

"That had better" warned Kate.

 

"Good" said Kate, smiling. She pressed a button on the intercom, to summoned Dr. Castle. "She's ready."

"Good work Kate. Bring her to room 12C."

 

Now Kate led Tommy down the hall by the hand again, until they reached room 12C. They went inside. Dr. Castle was there, along with a very pretty girl, who was laying down on the table. She was *so* hot! Tommy wished he could be as pretty as her. He could tell that she was a *real* girl.

 

"Tina, this is Jenna" said Dr. Castle. "She's currently in a state of hypnosis. She is going to be your roommate. You are going to live with her in the girl's dorm."

Tommy was overjoyed. He'd spend all of his spare time with a girl like *her*? She was even hotter than Kate! She was dressed exactly like he was, in a schoolgirl uniform.

 

"You're a girl now Tina" said Dr. Castle. "And I've hypnotized Jenna into think you are one too. Even if she was to see you completely naked, in her mind, she will see you as being female. So if she catches a glimpse of you in the shower, she'll only see that its a girl. If she sees you gluing your boobs back on, she only sees you as a girl. To her, you are not a boy, no matter what do you do. Only Kate and I know that you *used* to be a boy. All of the other girls will think you are one of them. And Jenna will *know* it."

 

Tommy was beyond excited now. He was going to live as a girl, and be accepted as one! He was going to share a room with a girl, and a very hot one at that! He was going to *live* in the girl's dorm! It really was a dream come true for him.

 

"What do you think of all this, Tina?" asked Dr. Castle.

"It is so wonderful! This is everything I could have ever hoped for!" said Tommy.

"I'm glad you find it to your liking" she replied. "Kate has advised you of some of our rules?"

"Yes" he said, smiling. "I like your rules."

"Good. Now I'm going to tell you of one more special rule for you. While you stay here, you are *not* allowed to touch yourself or to masturbate. If you do it, we will know. You're being closely watched. And every day, we will take a urine sample from you. If you're doing it, we'll find out. And then you will be expelled."

"I promise, I won't!" said Tommy, ashamed to know that he regularly did do himself.

"Very good Tina. Oh and by the way, you might want to pluck your eyebrows. I think you'd look even prettier if you did. That will be all for now. Kate will show you to your room, and Jenna will come in a few minutes later. She won't remember any of this, so act like you're seeing her for the first time."

"Okay" said Tommy.

 

Kate led him again by the hand, this time outside, across the road, and into a two story brick building. As the walked in, Tommy could hear the hum of conversation everywhere. But everyone talking was *female*. He looked around in amazement. They were all real girls!

Some were pretty, some weren't. Some were thin, some were heavy. They all dressed alike in a uniform like his. They smiled as he walked by, and some even said hello. He followed Kate until he came to his room. She showed him his dresser, which was full of nothing but clothes for a girl. He was still looking around the room with her, when Jenna came into the room.

 

"So, you must be Tina!" she said. "I heard that I was getting a new roomie."

"And you must be Jenna" said Tommy. "It is nice to meet you."

 

Tommy didn't know what to do, whether he should offer to shake hands or what. But Jenna came over, touched her cheek to his, and made a kissing sound. Then she touched her other cheek to his, and did it again. This time, he joined her in making the sound.

"I'll leave you two girls alone, so you can get to know each other" said Kate.

"Bye Kate!" said Tommy. "Thank you *so* much for everything!"

"Not a problem sweetie. I'll see you around" she said, closing the door as she left.

"So" said Jenna. "Tell me everything about yourself!"

 

For the next two hours, Tommy did nothing but talk to Jenna. And he was dressed up exactly like her! He decided that it was the best day of his entire life.

 

* * *

 

When Tommy woke up the next morning, he hardly dared to open his eyes. He had the most wonderful dream, in which he was living in a girl's dorm, dressed like a girl, and able to act like one all the time! He moved his hands onto his chest, where in his dream he had on a bra filled with large fake boobs, which were glued to his chest. When he found that he *was* wearing a bra, and that he *did* have the boobs on his chest, he realized it wasn't a dream. It was *real*.

"I'm a girl" he whispered, as he opened his eyes, and looked over to the side. There stood Jenna, wearing only her panties. She was about to put her bra on, and he caught sight of her perfect, tight, slightly upward pointing breasts. Her body was so perfect! Her panties were high cut, trimmed with lace. She looked like a perfect angel, all there for him to take. But he remembered Kate and Dr. Castle's warnings. He was a girl as far as she was concerned, so there was no chance that he could have her.

But he was fully aroused by the sight of her, and he found his hand was touching his erect penis. Quickly, he withdrew it. What if he made himself come? They'd kick him out for sure. He didn't want to be thrown out of a heavenly paradise, on his first full day no less! He had to use all his willpower not to touch himself, or to even think about doing it with Jenna.

 

"Good morning missie!" said Jenna.

"Good morning, sweetie!" replied Tommy.

"How was your sleep?" she asked.

"Just fabulous. I had the most wonderful dreams" he said.

"Me too. I dreamed that I was with this boy, we were kissing, and I felt all warm inside. I wanted him so much! He was just melting me. I felt happy all over."

"I felt happy all over in my dream too" said Tommy.

 

"I knew you'd be a perfect roommate" said Jenna. "They found a girl for me, who even dreams the same things I do."

Tommy giggled, as he watched her put on her skirt and the rest of her uniform. He got out of the bed, embarrassed that she'd see the bulge in his pants. But she seemed to take no notice, just as Kate said she would. And then Tommy got to live out a lifelong fantasy: he got dressed up as a schoolgirl, including full makeup, a ribbon in his hair, perfume, girl's shoes, jewelry, and everything. And then he went with Jenna to the school.

She showed him where the breakfast was served. There were hundreds of students there, all girls! And all dressed in the same outfit he was wearing. He was one of *them*! Tommy was so excited that he could barely eat. Jenna introduced him as "Tina" to dozens and dozens of girls. They were all so pretty. He was in awe of the scenery!

 

"There are so many new names" he said. "I'll never remember them all."

"You'll get to know a lot of the girls, in time" said Jenna. "You'll be attending class with them, studying with them, playing sports, having fun.... everything. In time, you'll get to know them, and I'm sure you'll make a lot of friends."

"You're so nice" said Tommy. "Thanks for helping me, on my first day."

"Think nothing of it" said Jenna, smiling.

 

Tommy watched how she clutched her notebook to her chest as she talked, as opposed to the way he held his arm down at his side, with his books. He raised his arms up to his chest, and hugged his notebook too. He had to remember to move, walk, talk and act like a girl. He didn't want to get found out! He couldn't. It was too important that everyone think of him as a girl. It was all so wonderful!

 

* * *

 

After spending his first full day as a girl, Tommy was so happy. It was everything he had ever dreamed of. All day long he had been with nothing but girls. The teachers were all women. The cafeteria staff were all women. Even the janitor was female. He really *was* the only male in the entire place. All these women, and him! He was exhausted from a long full day. After dinner, he and Jenna had studied about Jane Adams in their Women's American History class. Now it was time for bed.

Again, he got to see Jenna in various states of undress. Now she had on only a little pink teddy style nightie, with light pink trim. He had a blue one, although he kept his bra on underneath it, just like Kate had instructed him to do. He talked with Jenna some more, even after the bell rang for "lights out". He closed his eyes as he laid on his back, and he smiled. It was indeed the best day of his life.

 

Across the room, he could see the shadowy figure of Jenna. She was on her back, but her knees were up in the air. He could just make out something in her hand. Something that she moved to the spot right between her legs. She pushed it in, then pulled it out, as she started to moan softly. Tommy's eyes were popping out of their sockets, straining to see in the dim light of the room. She was doing herself with a dld!

All day long, Jenna had talked again and again about boys. In fact, Tommy decided that she was boy crazy! Now she was pretending to do it with a boy, right in front of him. He got so hard from hearing and seeing her do it. He wanted to touch himself so bad! Or he wanted to go over and climb on top of her, so it could be *him* inside of her, instead of the dld.

But no, he couldn't! What a torture it was to watch and listen for the next fifteen minutes, as Jenna pretended to have sex with some boy. Tommy finally drifted off to sleep, with thoughts of Jenna on his mind.

 

* * *

 

"I'm so sorry Tina" said Jenna the next morning.

"For what? You didn't do anything wrong" replied Tommy.

"Yes I did. I'm so used to sleeping alone, that I forgot you were there last night. I was imaging that I had a *boy* with me in the room, and it just drove me crazy! I had to do myself, right there in front of you. I'm sorry."

"There's no need to apologize" said Tommy. "I can understand."

"I'm glad you do" said Jenna. "In fact, I'll make it up to you. I've got an extra dld, which I've never used yet. Tonight, I'll give it to you, so you can do yourself, while I'm at it. That way, we can pretend together that we're double dating with some hot guys. We'll each have our own 'boy'."

 

She giggled. Tommy giggled too, although the thought of sleeping with a boy was disgusting. He could never do that! Although after hearing Jenna talk about boys all day long, he had a strange dream. He decided to tell her about it, because it would help make it sound like he was a real girl.

 

"I had a dream about a boy last night" said Tommy. "I can't remember much, but I felt warm all over, and so happy."

"Me too!" said Jenna. "In my dream, I was doing it with a boy. He was on top of me, taking control as he did me. Mmmmm, I felt so good!"

 

Tommy shuddered. He would never feel good about *that*! It was so strange that they had the same dream. But he didn't have time to think about it, there was much to do.

 

 

The day went very well for Tommy, as he got to spend it as a girl. But when he was at lunch, there was one moment when he almost slipped up, and acted like a boy. He was eating lunch at a table with Jenna and several other girls. They were complaining about their boyfriends, and how poorly they had treated them. Soon, it turned into a round of all-out boy bashing.

"Boys are so stupid" said one girl. "They only have one thing on their minds!"

"You're so right" said another girl. "They look at my boobs, not at my eyes. They only think of me as a object, not a person!"

"And they're so into themselves, always bragging about how wonderful they are. Who do they think they're fooling?"

 

"But they're so cute!" chimed in Jenna. "What, are you going to stop dating boys?"

"No way!" said the girl. "I *want* one. But that's not going to stop me from complaining about them!"

 

The girls kept on complaining, more and more, being meaner and meaner. Tommy felt a rage starting to build up inside him, and he felt such a strong urge now to step in and defend boys. But he knew he wouldn't. And he realized that by being so quiet about the topic, he was attracting suspicion to himself. And so, he finally added his own comments to the fray.

 

"Yeah" he said. "And they think sports is more important than *us*."

"My boyfriend does that!" said one girl.

"You're so right" said another. "They stare at the TV, not us sometimes."

"And they don't have any sense of fashion" added Tommy, now on a roll. "They'll wear anything, without thinking."

"I can't believe how bad my boyfriend dresses sometimes" said one girl. "He'll wear a shirt and pants that don't match."

"Or things five years out of fashion" said Jenna.

"Or things that just don't work!" said another.

"You are *so* right, Tina" said another girl.

 

The crisis was averted. His own boy bashing had made him escape notice. None of the girls at the table doubted that he was one of *them*.

 

* * *

 

Later in the week, Tommy was in another testy situation. He was with a group of girls, studying for a test, when somehow a topic came up that would scare the bravest boy: they started to take about their periods. It was so gross, as they talked about the bloating, the cramps, or the discharge from their vaginas. They compared notes on if they preferred pads or tampons. And he had to listen to it all.

But worse yet, he again knew that if he didn't get in on the conversation, it would raise suspicions. And so, he had to join in.

 

"I feel so grumpy" he said. "Especially right before it starts. Sometimes I just snap."

 

He had enough girlfriends to know how they got at "that time of the month".

"I know just how you feel" said Jenna. "I get that way sometimes too."

"I did that once, and really freaked out my boyfriend" said the blonde, across the table from Tommy. Her names was Alice.

 

"Speaking about boyfriends, you've never told us about yours" said Lisa, another girl at the table.

 

All eyes turned to Tommy. They wanted to hear about his *boyfriend*. Of course, he didn't have one, and he never would! But he didn't want to make up a bunch of lies; some day they might remember and ask him about the details. So he tried to sidestep the question.

 

"I'm not seeing anyone right now" he said.

"Maybe we should hook you up!" said Lisa.

"I know a cute boy too" added Alice. "I could introduce you."

 

Tommy couldn't refuse, or risk being exposed.

"That would be nice" he was forced to say.

"Who do you think is cuter?" said Lisa. "John Mayer, or Leonardo DiCaprio?"

 

Tommy felt panicked. How could he get them off this thread of conversation? He had to say something tough, until he could think of a way out.

"John, I guess" he said. "They're both cute."

"I think she deserves both!" said Jenna.

"Yeah, two hotties for Tina" added Alice.

 

Tommy felt sick to his stomach.

 

* * *

 

At other times, the girls talked about sex, which was quite uncomfortable for Tommy. As were the promises that they would set him up with a boy for the dance that was coming up the following Saturday evening. He *had* to find a way out of *that* one!

 

"Have you fucked a boy yet?" asked Jenna.

"No. I'm saving myself for marriage" said Tommy, finding a good excuse.

"Too bad" she replied, licking her lips.

"Maybe when Tina meets the right boy, she'll spread her legs for him" said Alice, laughing.

That *really* made Tommy feel sick.

 

"Come on, I think its sweet that she wants to wait to meet the man that she's going to marry" said Lisa, defensively.

That didn't bring much comfort to Tommy either. He wasn't going to marry a man! No way.

"Well I think that we should get her laid Saturday night" said Alice.

 

"I need to go pee" said Tommy, slinking away from the table.

 

* * *

 

Tommy was waiting at the lunch table for the girls to join him. He found a newspaper there, left by a teacher perhaps. He picked it up, and out of habit, he turned to the sports section to see how his favorite team had done in the match the night before. As he read the stats, he was startled by Lisa's voice.

 

"And you said you weren't seeing anyone" she said.

"Pardon?" asked Tommy, confused.

"Come on, who is he?" she insisted, as the other girls arrived at the table.

 

"What's up?" asked Jenna.

"Tina has a boyfriend!" announced Lisa.

"How do you know?" asked Alice.

"She's reading the sports section" she said.

"Oooh, is he cute?" asked Alice.

 

"I don't have a boyfriend!" said Tommy, defensively. Too defensively.

"Well, she must be reading the sports to impress *some* boy."

"Maybe she's just studying, so she can impress the boy we set her up with on Saturday" said Jenna.

 

They teased her, knowing it was a sore spot. But they were never as cruel as boys were, and they soon grew tired, and changed topics. Tommy realized he couldn't afford to let his guard down again, even for a moment. He was in heaven, living like a girl. He never wanted it to end. If he did something to ruin it all, he could never forgive himself.

 

* * *

 

On Thursday, Jenna and 'Tina' received permission to leave the campus for a shopping trip. 'Tina' didn't have a thing to wear for the big dance on Saturday. And so Jenna took 'her' shopping to find a new outfit. What a glorious moment for Tommy! He got to pick out different dresses, skirts, shoes, nylons, and more. He got to try them on. And he got to buy some for himself!

He ended up picking out a pink dress, with a taffeta skirt. It was *so* cute, and he couldn't wait to wear it, although he didn't know how he'd handle being set up with a boy. He *had* to avoid that. He needed to think of a way out of it! He loved being a girl in every way, except for "the boy thing". As the night of the party drew closer, he became more and more nervous. It took all of his concentration to make sure he didn't tip off the girls about his secret identity.

Each night as he laid in bed, listening to Jenna moan softly as she used the dld on herself, Tommy could not help but to think about boys. Boys wanted to do it with girls. If he went to the dance, they would think he was a girl. And they'd *want* him. He fell asleep do dreams of dating boys, kissing them, dancing with them, or even pleasing them. There was always a warm glow to his dreams, but the next day he'd feel upset about them.

 

The afternoon before the dance, Tommy had decided that he'd pretend to be ill. Then he wouldn't have to go. But the clothes *were* so cute, and he didn't know if he'd ever have another chance to dress up as a girl for a big dance. Jenna kept going on and on about how wonderful it would be for 'her' to finally meet a boy, and how she needed her best friend there at the dance to help scope out a boy for *her*. She made him feel like he'd be letting her down if he didn't go. And so Tommy caved in, and got ready for the dance.

It was a dream come true to put on his new outfit, heavy makeup, shiny pointy strappy high heel shoes, do his hair "up", and to be going out like that. He wore extra jewelry for the occasion, including a ring that Jenna lent him. He wore an extra-tight girdle under his outfit, to help define better curves. He liked how the extra support and constraint felt. And with the extra layer of tight material, it made the bulge between his legs far less visible. In fact, it was too tight for him to even think of getting hard. Now even in a tight outfit, nobody would be able to know his secret. Now he was ready to go out, and his heart was pounding!

 

When they arrived at the gym, at first nobody was dancing. The girls mostly kept to themselves, as did the boys. Then a few girls went out on the dance floor by themselves. Pretty soon, they were joined by couples who were dating. Now it was the time for the braver boys to start approaching the girls. Of course, they started to hit on Jenna right away, since she was just about the best looking girl in the bunch. One particularly handsome boy was talking with her at that moment in fact. His name was Jason.

 

"I'll dance with you, if you have a cute friend for my roommate" she said, pointing to Tommy.

"I'll be right back!" he said enthusiastically.

 

And sure enough, just a minute later, he returned, flanked by a second boy who had long dark hair, intense eyes and a muscular physique.

 

"This is Phil" said Jason. "He plays on the football team with me."

"I'm Tina" said Tommy shyly.

"You're very pretty Tina" said Phil. "Would you like to dance?"

 

Tommy's heart skipped a beat as Phil held out his hand. Tommy was trembling as he put his hand in Phil's and let the boy lead him out onto the dance floor. Tommy's head was spinning as Phil danced with him. When they danced a slow dance, it was Phil who led, with Tommy almost swooning. He didn't understand why it felt so magical. He didn't understand why he *liked* it. He should have hated it, but it felt like the most wonderful evening of his entire life.

 

At the end of the night, when the chaperones came in, Tommy even let Phil kiss him goodnight. They exchanged phone numbers, and promised to call each other the next day.

 

"Tina's got a boyfriend!" sang Jenna.

"Mmmmm" replied Tommy.

 

They both giggled.

 

It was only when he was laying down in bed that Tommy suddenly blushed bright red, as he contemplated what he had just done.

 

* * *

 

When Tommy woke up the next morning, Jenna was already up. She was undressing for the shower, when she yawned and stretched her arms to the ceiling. Tommy got a look at her perfect body, completely nakd. This wasn't the first time he had seen her like that. And he prayed that it wouldn't be the last!

He wanted to touch himself so badly at that moment, and relieve the tension that was built up inside him from not being allowed to come since he arrived at the clinic. Jenna was so perfect, and he was completely aoursed now. But he knew he couldn't do it, which made him feel frustrated.

 

"Hey Tina, you've got a note" said jenna, stooping down to pick up something that had been slid under the door. That gave Tommy yet another great look at her perfect body.

"From who?" he asked.

"Doc Castle. She wants you to see her, right away."

 

Tommy felt a sinking feeling in his stomach. Someone had found out who he really was, and he was going to be kicked out. He felt like crying. He had been in heaven for all the time he had spent as Tina. Now he was sure it was going to come to an end.

So it was with a heavy heart that he put on his clothes and his makeup, then took the long walk down the hall, his heels clicking on the tiled floor and echoing off the walls. He knocked on the door and waited. A few moments later, Kate opened it up, and showed him in.

 

"How are you today, Tina?" she said.

"Tired. The dance last night was so much fun" said Tommy, hopeful that this wasn't the end. Kate didn't seem upset; perhaps he had the wrong idea.

 

"I hear you even danced with a boy" she said.

"Yes, I did" replied Tommy, surprised that she knew. They really *were* keeping tabs on him at all times. What had they learned about him? What could they want? He took a seat, being careful to cross his legs like the other girls did. He was careful to do everything like they did.

 

"Tina, I know you've been a good girl, and you haven't made yourself come yet" said Dr. Castle.

"Yes" he said.

It had been hard, but he had managed not to do it.

 

"When you hear Jenna making *herself* come every night, what do you think of?"

"It excites me" he said.

"I know you imagine that you are a part of the action on her bed. When you do that, who are you?"

"What do you mean?" asked Tommy.

"Are you the man doing her? Or are you *her*?"

 

"I don't know" he said. "I never thought of that."

 

Dr. Castle took some notes, then continued.

 

"When you feel an urge to touch yourself, are you excited because you're thinking of being with a man, or are you excited because of a woman's body? If you see Jenna with no clothes on, does her body excite you as a man?"

"I guess that Jenna excites me. But I'm not excited about being with a man. I could never do that" he said, not sure why she was asking these things, and writing down the answers on her notepad. Now she wrote down something on a small notepad, and handed it to him. He looked down, and recognized it as a prescription.

 

"What's this?" he asked. "I'm not sick."

"In a way, you are" said Dr. Castle. "You are a girl, but you're still reacting like a boy. I'm putting you onto female hormones and testosterone blockers, so we can stop your little *thing* from getting hard anymore."

 

He looked at her shocked. Hormones?

 

"Of course, you won't have to worry about it, after the operation. I'll schedule you to have your genitals removed, so you can begin your transition towards being a *real* girl."

 

"I don't understand" he said. "I thought my folks sent me here to punish me for dressing up as a girl."

"No dear, they sent you here because they wanted for us to turn you *into* a real girl, so that you could live out the rest of your life as one. You father said you were too weak and frail to be a real man, and you'd be better off as a female. You mother would be *so* excited to have a little girl, instead of a messy smelly boy. They both *want* you to become a girl. That is why you're here."

 

Tommy was stunned. He almost felt like crying. Somehow, it felt like his parents had betrayed him. They didn't like him as he was! They *wanted* him to be a girl. His head spun.

 

"Now tell me" said Kate. "Have you dreamed of boys yet?"

"Yes" said Tommy, admitting the truth. "Just a little. Its kind of weird though. Jenna seems to have the same dreams that I do."

"That's because at night, you're both undergoing the same treatment" said Dr. Castle.

 

"Treatment?" asked Tommy.

"Yes. She was sent to us because she had too much of an interest in girls. Her mother didn't want for her to wind up as a lesbian. So we've been making her like boys instead. And *you* have been undergoing the same treatment. It is already there in the back of your mind; a growing desire. You even let that boy kiss you last night, didn't you?"

 

Tommy had to nod. It was true.

 

"With a word, I can turn it on in full. You'll lose all interest in girls, and you'll become just as boy crazy as Jenna is. You'll think of boys all day long, dreaming of being with them, wanting them, wanting to please them. You'll want more than anything to have a boyfriend."

 

Tommy was stunned. They could make him want that? They could make him become as crazy for boys as Jenna was? Now he felt real fear. They were talking about making him undergo an operation, go on hormones, and have his mind reprogrammed!

 

 

"Before we remove the last of your maleness, tell me something Tina. The first time we dressed you up, you were so aroused that your little *thing* got all hard. Did dressing up today arouse you?"

"No" he had to admit.

"You've come to learn that skirts and bras are just clothes" said Kate.

"Yes" he replied.

 

It was true. After all the time at the clinic, it wasn't the clothes that got him aroused anymore. He hadn't even thought about. Wearing a skirt had become *normal* to him, and as such, it wasn't something that got him hard, although he did feel a wonderful pleasure from being dressed up all pretty.

 

"The first time we put you into makeup, you were going crazy. How do you feel now?"

"Its just a thing I have to do each day to look pretty" he said.

"Like a chore?" asked Dr. Castle.

"Yes" he said.

 

"So you agree that after all this time, now that you're *used* to it, you're not dressing up just because it arouses you. You're doing it, because you want to be a real girl."

 

Tommy felt a panic. He didn't want them to turn him into a girl! He didn't want to be a real girl, and to like boys!

 

"Once you're on the female hormones, your skin will turn soft. You'll start to develop secondary female sex characteristics."

"Such as boobs" added Kate, helpfully.

"The testosterone blockers will prevent any residual male hormones from working on you. Your body will be swamped with estrogen, and even your brain will react, absorbing the estrogen, and making you even start to *think* like a girl."

 

Tommy felt frightened now, right out of his wits. They would do all of that to him?

 

"But you do have a choice" said Kate, in a calm gentle voice.

"That's right" said Dr. Castle. "As you can see, there are two doors on the back wall. You can walk through either one of them, and determine your future. If you go through the door on the left, you will become a *real* girl."

"There is a nurse waiting in there for you" said Kate. "She will strap you down on a gurney after removing all your clothes. Then she will inject you with a strong tranquilizer so you are immobilized. Then you'll start on your first dose of estrogen. A 'loading dose', as we call it in medical terminology."

"That's right" added Dr. Castle. "Then I will conduct the first of many operations on you. When you walk up, your testicles will be gone, thrown into the trash can with a loud splat. I'll also put implants into your hips to give you a proper female figure. Today, if all goes well, I might also reduce the size of your nose. We'll see how the operation proceeds."

"You'll be scheduled for a boob job, a chin job, removal of your Adam's apple, permanent laser hair removal, and of course the big operation, where we cut off your soft little penis, and surgically create your vagina and labia."

"And don't forget that even before you step through that door, we'll say the word to switch on your new programming. Even before the nurse has you take your clothes off, you'll be drooling as you look at the anatomical picture of the man on the wall. Before your head hits the pillow on the gurney, you'll be dreaming of making love with boys."

 

Tommy felt like he had been slapped in the head. He broke out in a sweat.

"What.... what is behind the second door?" he asked, his voice shaky and stammering from the panic he felt.

 

"The door on the right holds a completely different fate for you. If you enter that door, there is a shower. You will undress, shower, and then put on boy's clothes. When you return to this room, Jenna will be here, waiting for you. You know that she is boy crazy. Once she sees you, she'll be all over you."

"And you know enough about her, after having lived with her for two weeks, that unless you're a great fool, you'll be able to make her fall in love with you."

 

"The choice is yours" said Dr. Castle. "Do you want to go through the door on the left, and become Tina, permanently?"

"Or do you want the door on the right" said Kate. "You'll be Tommy, and you'll have Jenna as *yours*."

 

 

Dr. Castle folded her arms in satisfaction. Tommy wasn't the first boy that she had scared out of being a girl. It had all been very systematic. She had taken the arousal out of wearing female clothes. She had removed the aspect of teenage rebellion, by telling him that his parents *wanted* him to be a girl. And she had threatened the things that any male most feared: being confronted with the loss of his dick, and being threatened that he'd wind up with another boy.

It was a very powerful system. She could see it in his eyes. With all of his pent up need for release, and all of the desires he felt for Jenna, after being so close to her, and seeing her so intimately, he'd jump at the chance to have her. He knew how boy-crazy she was, and how she felt such an overwhelming urge for making love. She smiled. All that would be running through the boy's mind right now. Did he want to get his rocks off? Or to have them *cut* off?

 

 

Tommy stood there in silence, almost paralyzed inside. How could he even think like this? He absolutely loved the time he had spent as a girl. It was all so special to him. But did he want to become a *real* girl? The thought had never even crossed his mind.

 

"If you do not make a choice, I will be forced to make one for you" said Dr. Castle, applying even more pressure to him.

 

"A few times..." started Tommy in a shaky voice, "I've imagined myself being with Jenna. But I've imagined it with me being dressed up as I am now. I want to stay just the way I am. I want to like girls, and I want to have Jenna. But I want to be able to dress up like her, at least sometimes."

 

"It doesn't work that way" said Dr. Castle. "Staying in this room is not an option. You leave me with no choice. Kate, will you please set the time for two minutes?"

"Certainly Dr. Castle" she replied.

 

"When the timer goes off, Kate and I will say the hypnotic trigger word to kick in your reprogramming. If you are in this room, you will have no choice. The floodgate in your mind will burst open, and all of the new thoughts about boys will come rushing into your head. You will want them so much, that you'll rush into the door on the left, so that you can become a *real* girl. That way, you can have all the boys you will crave so much."

 

"Being a girl isn't bad" said Kate, encouragingly. "*I* sure love being one! It is so fun to be with a man, and to feel him as he makes love to you. I love going into a bar, and having all the men look at me longingly. They all want me. As they'll want *you*, once you become a girl. I'll make sure we give you really big boobs, so no man could take his eyes off of you, dear."

 

The clock started ticking, as Kate licked her lips. Dr. Castle decided to give him more motivation.

 

"You'll get to wear pretty clothes all day, every day" said Dr. Castle. "Whatever you like! As a girl, you can even dress up in boy's clothes, and it will be sexy. Your options will be limitless! I too love being a woman. And you will too, once we've removed those nasty things between your legs. They just don't belong there, do they? You were never meant to be a boy. And you know it."

 

Kate opened up a drawer, and pulled out a prosthetic device. It looked exactly like a large penis, along with dangling testicles. She pointed it right towards Tommy, holding it out for him to take.

 

"Take it" she offered. "That way, when we say the word, you'll be ready. When we make you want boys, you'll be so hungry for them, that you'll take this, put it into your mouth, and you'll feel a wash of new pleasures. Just think! In less that one minute, you'll be on your way towards becoming a real girl! Just like me."

 

Kate unbuttoned the top of her shirt, revealing to Tommy her large breasts, supported by a sheer underwire bra.

 

"This can be *you*" she said. "You need to make your choice. Do you want to feel me up? Or would you rather feel ones like these on your own chest?"

 

"Thirty seconds" said Dr. Castle.

 

"I just love being a girl" said Kate. "And so will you. Come with me Tina. Join us! Become one of us! Let us remove your little penis, so that you can become a real girl! Think how wonderful it will feel to have estrogen flowing in your bloodstream! Think how great it will be, to become just like Jenna. And me. I want you to be a girl Tina. I want you to become female. Nothing excites me, like being able to bring a boy over to *our* side. Are you one of us Tina? Are you a girl?"

 

"Five seconds!" warned Dr.Castle. "You had better get moving!"

 

Tommy stepped forward, opened the door, and went inside the new room, just before the buzzer went off.

 

* * *

 

 

Tommy gasped for breath, as Jenna screamed as she came again. Her eyes rolled back in her head, as the second orgasm of their lovemaking session washed over her. She and Tommy were both spent. He finally pulled out of her, and rolled over to lay at her side, and to hold her close.

"I'm so glad that you chose to be mine" she whispered into his ear.

"Me too" he said, breathless. "I love you."

"And I love you too, sweetie" she replied, as she stroked his chest. "I'll love you even more, once your boobs start to grow."

"What do you mean?" asked Tommy, confused. "I chose to be a boy."

"I know, my love" said Jenna. "But I liked you better as a girl. They may have retrained my mind to like boys better, but that doesn't mean that I'm not still turned on by girls. I've decided that bit by bit, I'm going to feminize you, until you look just like a girl. But I'll let you keep that thing between your legs, so we can still do this. You'll be my man, *and* you'll be my woman."

 

Tommy felt a strange rush. He could keep what he had between his legs, have Jenna, *and* be her girlfriend too?

 

"You mean..." he said.

"Yes. I'm going to dress you up as a girl. I'm going to make you become pretty. I'll get you on hormones, and make you grow boobs. You'll be a pretty girl all the time. *My* pretty girl. And we'll still be able to do this. Will you do that for me? Will you become Tina again? Will you let me turn you into a girl?"

 

"Yes" said Tommy. "I will."

"Good girl" said Jenna, kissing him on the cheek. "Good girl."

  

  

  

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