Discoveries

by Jennifer White

 

Tommy had to stop to catch his breath. He had just made himself come so hard! It was a good thing he had done it into a towel, so that it wouldn't get all over his sister's skirt, that he had taken from her closet. It was a cool, lightweight material, and he loved how it felt against his skin.

He sat up, and looked down admiringly at the full cups of his mom's bra he was wearing. His sister Jan had bras too, but they were too small. He wanted to have big breasts like his mother. But Jan's clothes fit him just fine, and she liked to dress up all pretty.

Some of her things he just borrowed, like the skirt he was wearing now. If he tried to keep it, she might notice it was missing, and investigate. But with a whole drawer full of panties, or her drawer full of girl socks and nylons, she'd never know he was taking something to add to his permanent collection.

His mom had some cool stuff too, but Jan dressed up like all the girls at school did, in their sexy little outfits. Of course, mom wouldn't let her go out of the house sometimes in the outfits she selected. But mom didn't know that as soon as Jan got to her friends house, she'd change into something even skimpier. But Tommy smirked neither of them realized that while they were out having a good time, he was wearing *their* clothes.

It really got him off like nothing else. He loved looking at pictures of women. His friends from school all had copies of Playboy that they stole from their dads. He loved seeing the naked women. He was very turned on by all the girls. But when he was alone, it was even more exciting to dress up as one of them, and pretend that he too was a girl.

 

Tommy's father had divorced his mother and left, when he and Jan were still very young. He didn't even visit them, and had stopped the child support payments long ago. Tommy's mother always had bad things to say about him, and men in general. They were bad. They hurt women's feelings. They didn't *have* feelings. He had heard his mother talking to her friends on the phone about it. He felt ashamed to be a boy.

But when he could dress up, he was his true self. A girl. He wished he had been born a girl. Jan was so lucky. He desperately wanted to be pretty like her. And now that she was a teenager, she was starting to develop breasts. She had a period. He felt *so* jealous.

Yet he knew already that if he went around telling people that he wanted to be a girl, he would be shunned. His friends would drop him like a hot potato. His enemies would make fun of him. Even the girls at school would tease him. So he had to keep it a secret.

Tommy wished that somehow his mom would go on a long vacation, and take Jan with her. Then he'd have the whole house to himself for a long time, and he could try on makeup, and the other girly things that Jan had. He had worn her necklaces, but her bracelets were too small to fit over his wrists. And he didn't dare ask to get his ears pierced like hers. It made him feel sad that she could do all those things and he couldn't. Mom wouldn't even let him grow his hair long!

Tommy sadly undressed. He folded up the skirt, so he could return it to Jan's closet before she came home. The panties, the nylons and the bra were all *his*. He hid them under the mattress in his bed. Sometimes he put them in his closet, but he was going to dress up again before he went to sleep. So he used his alternate location, under the mattress.

 

* * *

 

"Tommy, your friend Jim is here!" yelled his mother.

Jim liked to shoot hoops, as did Tommy. He met his buddy, and soon they were in the back yard playing a game of one-on-one. Jan was watching TV. And their mother was putting away the groceries. She had bought a new box of tissues for Tommy's room, so she went in to put them on his night stand.

"What a mess" she said, putting her hands on her hips. How many times had she told that boy to make his bed? It was all a mess now, with the cover all tossed about. She shook her head, and went to make the bed.

The sheet was pulled too far over to one side, so she had to pull it out to straighten it. When she did so, she saw something white fall out from between the mattress and the box spring. She bent down to pick it up. When she saw what it was, she gasped. It was one of her bras.

She had bought three new underwire bras on sale, because they were a brand that was very comfortable on her. But when she did the wash, only two turned up. Now she knew where the third one had gone to. She lifted up the mattress to see what else was under there.

She discovered a pair of Jan's panties, a pair of nylons, and one of Jan's tank top shirts. Jan had said that someone was going through her closet, but it had seemed unlikely that anyone would have been doing that. She had thought Jan was overreacting, as many teenage girls do. But she had been wrong. Someone *had* been going through Jan's things. Tommy.

 

As she made the bed, she wondered what she could do to cure her son of this behavior. It wasn't right for him to be going through his sister's things like that. She decided on a plan to make sure he never did it again. But she would need Jan's help. She hoped that Jan was mature enough to help, and not to tease her brother. She would need to have a long talk with her. And a couple of days to plan everything, and buy the needed supplies...

 

* * *

 

Tommy slept in to 9:00 on Saturday. It was his favorite day of the week. Nothing to do, no school, no stupid family visits, or any of that. Just time to relax, watch the game on TV, read a book (a book for girls, stolen from his sister of course...or one of her glossy magazines), and hopefully get some time alone so he could dress up.

He could smell breakfast cooking. His favorite meal of the day. His tummy growled.

"Amanda, time to get up!" called his mother, knocking on his door.

Amanda? Who was that? He must not have heard her right. He turned over and stretched. A minute later, his mother opened up the door and poked her head in.

"Amanda, it's time to get up. Rise and shine!" she said. "I've got breakfast cooking for you and your sister. Then we're going shopping to get new dresses for the both of you. I want you both to look pretty for Aunt Elizabeth's wedding next month."

What was she talking about? Amanda? Dresses for the stupid wedding? Huh?

 

"Come on slowpoke" said Jan, stepping into the room.

"I'm getting up" said Tommy.

She stuck out her tongue.

"I'll eat all the bacon before you get there."

"Hey Jan, what's up with mom?" said Tommy.

"What do you mean?"

"She called me Amanda. She said something about buying a dress today."

"That's right. We're getting matching dresses for Aunt Elizabeth's wedding. You and I will be the cutest two girls there."

"What are you talking about?" said Tommy, thoroughly confused.

Jan cocked her head and gave a funny look.

"What do you mean 'what am I talking about'? You know. Don't you remember our family discussion last night?"

"No..." said Tommy. "What did we talk about?"

"About how you're a girl now. About how you're Amanda."

"What?" said Tommy.

"I think its really cool that you're a girl now. You can move into my room, and we can have bunk beds. And now I can have all my girlfriends come for sleep overs, and you can join us. I am *so* excited that you're my sister now."

She stepped out of the room.

"Come on Amanda, the eggs are done! Lets eat."

Amanda? Him? A girl? He didn't remember any family discussion! Yes, it was a fantasy of his to be a girl, but he didn't know if he could handle *this*.

Tommy pulled on a T-shirt and went downstairs.

"Young lady, you do not dress like that around the house!" said his mother. He was wearing just boxers and the T-shirt.

"What am I supposed to wear?"

"I expect my girls to at least wear pants, if not a skirt. And no more boxers for you. What, do you think you're a boy or something? Go put on your panties, and come back here after you're properly dressed. And we don't go around this house without bras on! Do you hear me young lady?"

"Yes mom" said Tommy, as he scurried upstairs. Mom had just told him to put on panties and a skirt! And a bra! This could not be happening! He went upstairs, put on the bra and panties that were under his bed, then looked around for what else to wear.

"Here" said Jan, handing him a skirt and a cami top. "Come on. Foods getting cold."

He put on the skirt, and admired how it looked on him. Then he slipped on the top. He still could not believe that his mom actually *wanted* him to dress like this. He was so excited.

He went downstairs and ate.

"Jan, will you please teach your sister some table manners? She's eating like a boy."

"Look stupid" said Jan. "You have a knife and a fork. A piece of toast is not a utensil. Eat civilized."

Tommy mimicked his sister's manners, as she ate properly and daintily. What small bites! How are you supposed to get full eating little tiny bites like that? But he was eating like a *girl* does. So he wanted to learn the right way.

"Someone needs to shave their legs" said his mother in a teasing tone of voice. "When you shower today dear, don't forget. You want to look nice when we go out dress shopping later today."

Go out? As a girl? Tommy froze up. He couldn't do that. They'd all know about him! But he didn't want all this to end either, being treated like he was a girl. He didn't know what to do. Maybe she was just kidding. He'd go along with things for now, and cross that bridge when he came to it.

 

After breakfast, Tommy got up.

"Amanda, it's your turn to clean the table and do the dishes."

"Those are girl's chores" said Tommy.

"Exactly."

Oh yeah, mom was treating him like a girl now. He almost forgot.

"What about the garbage?"

"Well, that's a boy's job. But since I just have two daughters, you two will have to take turns doing that too."

"I don't want to get my hands all icky touching garbage!" said Jan.

"Then use gloves" replied her mother.

Tommy did the dishes after clearing the table. Then he went back upstairs to take his shower. Jan and his mother showered in the bathroom downstairs, were all the 'girl stuff' was. He showered upstairs. He stepped in, and turned the water on. He looked around. The shower had changed.

On the hanging shelf over the shower head was a completely different collection of shampoos than normal. Plus conditioner. And a pink scented bar of soap. And a pink shaver! He was very excited. He used the girly shampoo, then rinsed it out. It made his hair feel silky and soft. Then he put in the conditioner.

While that soaked in, he went to work with the shaver, removing the hair from his legs. Then he did under his arms. He rinsed off the conditioner, and then used the pink scented soap all over his body. The shower door was all steamed up now.

There was a knock a the door, and Jan walked in.

"Jan! Don't look!" said Tommy.

"Why not?"

"You'll see me naked!" he said.

"Oh Amanda, you silly. Sisters see each other naked all the time. Don't be such a fuss-budget. I just wanted to tell you that mom said that after you dry off, put on your robe and your slippers, and come to my room. Got that?"

"Yes" said Tommy.

"Good" replied Jan, as she turned and left.

Tommy rinsed off, then went to dry off with the towel. His blue towels were gone, and pink ones were in their place. Hanging on the back of the bathroom door was a pink robe. And there were fuzzy pink slippers in the corner. He hadn't noticed them before. Jan must have dropped them off when she came in. Tommy stepped into the soft slippers, wrapped the silky robe around himself, and went to Jan's room after hanging up his towel on the bar.

His mom and Jan were both waiting for him in her room. Jan handed him a pair of silky white panties. He put them on with his back turned to the both of them, so they wouldn't see any of him. Then he turned to see her holding out a bra. He was disappointed that it was one of Jan's smaller bras, not one of his mom's big ones.

"Don't look so disappointed Amanda. You're just a young girl. Your boobs will keep growing for years to come. You'll fill out a big bra one day. But for now, you need something smaller, in your size.

Tommy took off the robe, and put on the bra. He was very good at it, having worn one hundreds of times before. His mom and Jan were impressed at how good he was at it.

"Your sister is older than you" said his mom, "so she has developed a little more than you. But I want you two girls to look the same for the wedding. So I got you these."

There were a pair of little gel inserts for a bra. The box said they added two sizes to your bust. Now Tommy's smaller bra was indeed filled out full.

"There. Just like you're sister" said his mother.

Tommy shivered all over. Those were words he had longed to hear all his life. 'You are just like Jan now'.

 

Next, Jan handed Tommy a pair of ecru colored nylons. He slipped them on carefully, so as not to snag them. He had ruined several pairs in the past before figuring out how to do it right. Again, they were impressed.

Then he was given a white slip to wear, followed by a long navy skirt. For the top, his mother gave him a white silky blouse, with lacy ruffles on the sleeves and neck.

"You're very pretty Amanda" she said, smiling approvingly.

Jan now had shoes for Tommy to put on. He had never worn girl's shoes before. Thankfully, these only had a little bit of a heel.

"You need to have something nice and formal on your feet, so you can really see how you'll look in the dresses when we go shopping later" said his mother.

Tommy was admiring all his pretty clothes. He was so excited! They were treating him like a girl, and he loved it.

"Now for your makeup" said Jan.

Tommy sat down, as Jan and his mother applied foundation, powder, mascara, eyeshadow, blush, and other little cosmetics to his face. He had never worn it before, and it made him feel so pretty, and so much like a real girl.

"Now put on your own lipstick" said his mother.

His hand was trembling as he put it on for the first time. Wow, it made his lips look so full, so wonderful. He just stared at himself as his mother put a wig of long blond hair on him, just like his sister's. He didn't move as the fastened it in place for him.

"When we go to the mall, we'll get your ears pierced today" said his mother.

Tommy felt things get tighter in his panties. The more they did to him, the more excited he got. He wanted to run into the bathroom so he could 'relieve himself'. He didn't think he had ever been so aroused in all his life. He felt special. He felt like a girl.

"Hold out your hands, Amanda" said his mother.

Tommy held them out, as Jan and his mother put rings onto his fingers. Jan put a bracelet onto his right wrist. It was tight, but she got it on somehow. Then they set to work painting his nails! Tommy never had his nails painted before, but he had fantasized about it many times. He was in heaven as they put on three coats of a pretty pink color, and a clear coat sealer on top.

He stood up and looked at himself in the mirror. He looked like a girl. A real girl!

"All right girls, time to go shopping" said his mother.

"I just love going to the mall Amanda, don't you?"

Tommy had his doubts before about going out of the house as a girl. But seeing himself in the full length mirror now, those doubts were completely cast aside and dispelled. He looked like a girl. He looked just like his sister. Nobody would know it was him. He *wanted* to out now. To go shopping for pretty clothes. And to get his ears pierced!

"I can't wait, sis" he said.

Jan squeezed his hand. She smiled warmly.

"I'm so glad I have a *sister*" she said.

"I'm glad to be your sister" replied Tommy, squeezing back.

 

They all got into the car, and drove to the mall. They came in from the north side, so they had to go through one of the department stores. They looked at all the different cosmetics. Tommy loved the smells and looks of them all.

"We'll stop on the way out, and get each of you girls something as a treat" said their mother.

They entered the mall, and stopped at each storefront to look inside at the pretty clothes and the cute shoes. Tommy wanted them all. He was almost drooling when they stopped in to browse at a store that sold handbags and accessories.

"Can I have this one?" he asked his mother.

"Sorry Amanda, but I can't afford a Prada for a girl your age. You'll have to settle for something that isn't a name brand. Or you can borrow your sister's old Kate Spade."

'Amanda' insisted on having 'her' own bag, so 'her' mother bought a knockoff of a DKYN for 'her'. They continued into the mall, where they found the jewelry store where they sold ear rings, and did ear piercing.

"Can I get these?" asked Tommy, pointing to a pair of large hoops.

"I was thinking something smaller, like a stud" said his mother.

"Jan, your friends all wear these, don't they?"

"Yes" said Jan. "Or dangling ones like these."

She picked out a pair of silver earrings, with long dangling tear drops. Tommy looked at them, then looked back at his mother, like a dog begging for a bone.

"All right Amanda, you can have those" she said with a nod.

Tommy sat in the chair, as the pretty young girl who worked there cleaned off his ear with a wipe, which she explained would help kill any bacteria.

"Now when we put these in, you'll need to keep them in for at couple months at least. Otherwise, the holes will close back up."

"Sure" said Tommy excitedly. Although this was something different now. Up to this point, everything that had been done to make him feel like a girl could easily be reversed. He could always take off the bra, take out the falsies, and look like a boy again. But the earrings he had picked out were definitely *girly* ones. This would not be easily undone.

"Go ahead" he said, as she put the cold metal device up to his ear lobe. There was a quick shock of pain, then it was all over. Tommy flinched when she did the other ear. But now, it was complete. He was wearing earrings.

It was great to feel long hair touching him on the shoulders, the face, the neck as he moved around. But now he could also feel a little weight on his ear lobes, and feel the metal swinging about as he moved. He felt the skirt touching his legs gently as he walked. He savored the sensation of the bra straps digging into his shoulder. He proudly held his purse over his shoulder, and tucked it in between his arm and his body, like his sister and mother were doing. The heels of his shoes clicked against the hard floor of the mall. He felt like a real girl.

 

The three of them now went into the department store at the south end of the mall. It was time for Tommy and his sister to pick out a dress for the wedding. They went into the store, and Tommy was in heaven. There were so many dresses to choose from! He wanted to try them all on, now that he was a girl.

There were formal dresses, pretty dresses, sexy dresses, frilly ones, dowdy ones, short ones, long ones, one piece, two piece, a-line, sarongs, and a host of others. Tommy really liked a black one with a long skirt that featured a slit down the side, but Jan and his mother smirked at that choice. Instead, they picked out a teal blue strapless dress. Jan and he went into the dressing room to try them on. Unfortunately, Tommy didn't have any real boobs to hold the dress up, so it wanted to slip down on him.

"Don't worry honey, there are ways to do it, even if you're a small breasted girl."

Tommy and Jan modeled their dresses together, in front of the mirror.

"I think we'll get you matching ribbons for your hair" said their mother. "And we'll do your hair up all fancy for the occasion. I feel so happy! My little girls are growing up to be beautiful young women."

 

With their new dresses in a long plastic bag, then in an outer bag sealed with a zipper, they could be safely carried to the car without fear of getting them dirty. In the mall on the way to the car, Jan kept bugging her mother to let her buy something else for 'everyday' wear. She finally gave in, taking them to a clothing store popular with all the girls in school.

"You may each buy one outfit" she said.

Jan picked out a pair of jeans and a white T-shirt that had pink trim and silver glitter spelling out the company logo. Tommy picked out a knee length floral skirt, and a powder blue top. Their mother paid for the outfits, which both of her children asked if they could wear home.

"No girls, you're going to have to wait until we're at home."

They took their new clothes to the car, and drove half way home, where they stopped for dinner at Jan's favorite restaurant.

"Now mind your manners Amanda" said Jan. "Don't embarrass me here!"
"I promise, I'll be good" said Tommy.

He in fact was good, sticking to salad like his sister did, and eating in small, dainty elegant bites. He tried to imitate her in all ways. She was his role model. He wanted to be just like her.

 

* * *

 

Back at home, Jan helped Tommy redo his room. She helped him hang posters, get put all the icky 'boy stuff' into boxes, and she even shared some of her things to make the room looked more girly.

"When we get the bunk beds, you'll move in with me" she said.

Tommy thought that was the coolest thing ever. He was Jan's *sister* now. She gave him some of her old clothes she no longer wore, as they emptied out his drawers. Now he had all girl clothes to wear, all the time. It was getting late, and he was tired now. Jan gave him an old nightie, which he put on.

"Good night Amanda" said his mother, kissing him on the cheek.

"Good night mommy" he replied.

"Sweet dreams" she said, shutting the door.

It was a wonderful end to his first day as a girl.

 

* * *

 

The next day, Sunday, was just as good for Tommy. All day long his mother and sister treated him as if he really was a girl. They called him Amanda, they acted like he was one of them, and they constantly did little things to remind him that he was now a girl.

Their mom took them to see a movie, and out to dinner again. When Sunday came to a close, Tommy was exhausted. It had been such a long, fun weekend. He loved all that he had done, and all that he had felt. It was great being a girl.

 

* * *

 

"Rise and shine! Time to get up Amanda" said his mother.

It was a gray and rainy Monday, and it was time for school. Tommy hated school, and most of all on a Monday.

"I laid out an outfit for you" said his mother as she closed the door.

Tommy got up, and turned on the lights. It took a second for his eyes to adjust to the brightness. There, on his dresser, was the outfit his mother had chosen: a navy blue skirt with matching blazer, white tights, and a white shirt. Tommy gulped when he saw the outfit. He couldn't go to school like that. The guys would kill him! A look of panic set in to his eyes.

"Jan, get in here" he said.

"What's up?" she said.

"Look what mom laid out for me to wear to school! I can't wear that!"

Jan laughed.

"Mom thinks this is 1950 or something. Nobody at school dresses like that anymore. I tell you what, why don't you wear my jeans skirt and the white top I gave you yesterday? I'll clear it with mom."

"But Jan, I can't go to school dressed up like...."

"Like what Amanda?"

"You know! Like a girl?"

"Why not?"

"Because, you know how they'll treat me if I do!"

"Now look Amanda, mom said that you're a girl now. If you're a girl, then you're a girl. I'm fine with that. But I can't have a sister go goes to school every day pretending she's a boy!"

"It's not like that!" protested Tommy. "Don't you understand?"

"All I understand" said Jan, "is that mom is so happy. She thinks you're really a girl now. She asked me if you've had your first period yet. Don't you understand? Whatever you did, you've convinced her that you *really* are a girl. I think you've got two choices. Either put on something pretty and go to school, or tell her that you're really a boy."

With that, she got up and left the room, leaving Tommy to sweat it out. What a terrible bind to be in! He wanted to be a girl, but not in school in front of all his friends! Why were they being so mean to him? He stood there not knowing what to do.

 

"Did you tell him?"

"Just like you told me to mom. I think he's realizing it now. He can't go to school as Amanda. The kids would never let him live that down. He'll be forced to revert back to being a boy."

"Ssh, I think he's coming now" replied her mother, returning to her task of buttering the toast.

Tommy walked in the room. Jan and her mother turned around triumphantly to see him, so that he concede defeat to them. But both were shocked.

"Do these shoes go with this outfit?" asked Tommy, as he held up the black flats. He was wearing the jeans skirt and the white top, as Jan had suggested. He wore his wig, and he had his falsies stuffed into his bra.

"You want to go to school like that?" asked his mother.

"I know mom, you laid out an outfit for me, but it just isn't my style. I need to wear something more like the other girls do. You don't want me to get teased, do you?"

"Teased? Tommy, they'll eat you alive like that!" said Jan.

"Tommy? Who is Tommy?" he replied. "I'm Amanda, your sister, remember?"

"Mom?" said Jan, not knowing what to do.

Her mother decided to lay it on thick, and once more try to force the issue.

"If Amanda wants to go dressed like that, she can" said their mother.

She turned to Tommy, and looked him in the eye.

"Young lady, if you're going to dress like that at school, it tells me that you're really trying to impress the boys. I think you're to young to date boys yet, so you had better be careful. I don't mind you flirting with them, but you are not to start dating yet. Is that clear?"

"Yes mother" said Tommy.

"Now I know that boy Jim is very interested in you. And I know you must feel like he is your friend. But you are at an age now where boys will try to take advantage of you sexually, if you let them. Have you been kissing him? Is that what you two always do when you're alone?"

"No!" said Tommy.

"Good. You need to wait. When you get as old as your sister, you can date boys. You're just a young girl, and you're not ready for boys yet."

Tommy nodded.

"I know you like boys. I know you think about them all the time, and that you want to be with one. I know you imagine yourself kissing boys, and holding them in your arms. I know, because I was once a girl your age. But you need to wait. Now tell me, who is the cutest boy in your class?"

"I don't know" said Tommy, blushing. He didn't like boys! He would never date one.

"I think she has a secret boyfriend" said Jan. "She's being very coy, but a sister can tell when her own sister is in love."

Tommy blushed even more

"Amanda has a boyfriend!" taunted Jan.

They waited. He should have snapped at any moment. He should have given in, and told them that he was really a boy. But he just stood there.

"Mom, can we talk about this later? I have to get my makeup on, and I don't want to be late" said Tommy.

His mother looked at him with wide eyes. She had just given it to him with both barrels, saying things that any boy should have blown up at. But he didn't get mad. He didn't revolt against it. Instead, he wanted to get pretty for school. She realized that she had made a huge mistake. Tommy really did want to be a girl. For real. She hadn't helped cure him. She had pushed him over the edge.

Forced to make up his mind, he had chosen to go to school as a girl. If he went this day, he would go *every* day. He really *did* want to be Amanda. He really *was* a girl inside. She gasped as she realized this.

 

"Mom, I just talked to him. He really thinks that he is a girl now" said Jan. "What are we going to do?"

"Nothing" replied her mother. "Nothing. We'll let him go to school like that. If he survives the day, then we'll take him to the doctor, and start him on female hormones. He really does want to be a girl. If that is what he wants, then I think we should both do all we can to help him."

 

"Mom, I'm ready" said Amanda.

"Your makeup is very pretty" she replied. "Come on girls, you're going to be late! Grab your purses, and lets get going."

They drove up to the school, where they said their good-byes. Amanda and Jan ran up the steps to their first classes of the day, not wanting to be late. Amanda couldn't wait for class to start. Today was *her* first day of school, and *she* wanted to make the most of it. She got to her desk, and smiled as she put down her backpack and pulled out her pink spiral notebook. She was a schoolgirl now, and it was time for her education to begin....

  

  

  

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