That made her heart melt again for him. A boy, who would let her dress him? And one that had very similar tastes to her? It was a dream come true. She led him around the mall, and picked out an outfit for him.

As they started out, Jack stopped at one of the stands in the middle.

"Lets get tattoos" he said.

"Mom would kill me!" replied Melissa.

"No, I mean the temporary kind."

She thought it was a great idea, so they each picked one out, without showing each other. The lady behind the counter applied them onto their skin, and they couldn't wait to show off for each other.

Melissa had picked out one with kitty. Jack thought it was really cute. Then he showed her his: it was a horse, running under a rainbow.

"Aw, how sweet. Very pretty" said Melissa. She suddenly blushed. What an insult to throw at a boy! But Jack just smiled, and seemed to take it as a compliment.

What a wonderful guy. She really wanted him now. She wondered when he would finally put his arm around her, and kiss her like she longed for.

They walked home smiling and laughing together.

* * *

Jack was uncomfortable in his jeans. He had been losing weight this summer so far, but they just weren't fitting right. He would have to go shopping with Melissa soon, and get a new pair. But those Capri pants she wore were so cute, he couldn't get them out of his mind. He wanted to try a pair of those himself.

Jack was humming a tune from Chicago, which had rented the night before. Becky had joined Melissa and him on the couch, and the three had a very good time talking afterwards. Jack was glad that he was getting closer to his sister this year. In the past, they had fought more than they should have, and their parents were glad to see the change.

"Can I borrow these?" asked Jack, looking at a couple of Becky's romance novels she liked to read.

"Sure thing!" she replied. She thought that he was looking for ideas on how to treat Melissa, and she thought it was sweet of him. But there was something more to it. When Jack saw the picture of the handsome man on the cover, holding the swooning woman, something inside him jumped, and he just wanted so much to read that book and find out what the story was.

He had never been interested in romance books before, but it looked so interesting! But then again, he had learned many new things this summer. Like that magazine he had stolen from his sister. He was going to drool over the pictures of all the girls, but he found out that all the articles were really interesting! So now he was regularly reading Cosmo, Glamour, and Vogue. Who would have thought that they were such good reading? He would sneak them out of her room when she wasn't looking.

One day when he was returning her copy of Cosmo, he looked at her open closet door. He walked over, and put his hand on a silky slip that was hanging there. He felt so excited! His heart pounded, and his breathing became rapid.

He looked around to make sure that nobody was there, and grabbed the hanger from the closet. Then he quickly picked out a skirt and a top, and ran over to his room.

Jack locked his door, and put on the clothes he had just taken from Becky's room. He felt so natural in them, like it was *right*. He read the romance book, and was completely at peace.

Jack found that he really identified with how the heroine was feeling. She was young, around the same age as him, and seemed to be almost a cross between his personality and Melissa's. The book was just enthralling reading for him.

Jack almost forgot to put his own clothes back on, when his mother called him downstairs for dinner. He carefully hung up Becky's clothes, and put them in the back of his closet. He would return them tomorrow.

* * *

The next day, after Jack's parent's went off to work, and Becky left for her job, Jack walked into her room to return her clothes. He hung them up in her closet, but looking at all of her things made him feel excited again.

Almost before he knew it, he had picked out another outfit. But now he went to her dresser, dug through her drawers, and found her underwear. He grabbed a pair of panties, and a bra. He took everything back to his room, and changed clothes.

Jack sat down, and read a few chapters from the romance book. The heroine's name was Jacqelyne, and the more he read, the more he felt exactly like she did. It was like her thoughts and feelings that poured forth on the page were just like what he felt inside. He had never found a character in a book that he could identify with like this! Jacqelyne.

Jack was due to meet up with Melissa, so he undressed, and put on his own clothes. But they seemed so dull, so drab! He wanted to wear something exciting, like Becky got to wear, or like Melissa did. He chose out the outfit that Melissa had picked out for him at the mall, but he kept on Becky's panties. At least he had them.

It was because they just fit so well! They felt so much more comfortable than his own boxers, and he decided that he would get a few pairs of his own to wear, next time he visited the mall.

After talking with Melissa for a while, he noticed that she had a strange look on her face.

"What's the matter?" he said. He had been noticing subtle things about people lately, like he could tell a lot more about what they were feeling. Something was making her uneasy.

"Jack, do you normally wear an undershirt?" she said.

"No, I don't unless its really cold in the winter."

"That's the shirt I picked out for you, isn't it?"

"Why yes! I knew you'd notice" he said, proudly.

"Well you look different. I mean....come with me" she said.

Jack followed her into her bedroom. She had him look into the mirror.

"Jack, look at your chest"

He did, but he didn't really notice anything.

"Look closely. At the color."

Jack looked again, then it hit him. How had he failed to see? You could clearly see the wide dark rings of color around his nipples through the white shirt.

"Oh no" he said, "I show right through."

"We need to do something quick" said Melissa. "Cindi and Rhonda will be over in a few minutes."

"I'd be so embarrassed for them to see me like this" he said. How could he have not noticed? He looked so slutty with his nipples showing through like that. He turned to the side, and you could also clearly see how they stood out from his chest. He shook his head.

"Quick, give me a bra" he said.

"I was thinking more 'jacket' or 'dark shirt'..." she said.

Jack motioned to her again, and she relented. She got out a bra, and handed it to him. Jack took his shirt off, so he could put on the bra. Melissa looked at his chest, smooth and hairless. He had such small boobs, he would look strange in a bra. It was too bad that she hadn't kept any of her older bras, which would have fitted him much better.

Jack put the shirt back on, and looked in the mirror. He looked very satisfied with himself, as he pouted and posed before the mirror. Now the large dark rings of color around his nipples were hidden, and his nipples themselves didn't stick out anymore. But you could clearly see that he was wearing a bra.

Suddenly, Rhonda and Cindi burst through the door.

"Melissa! Jack! Hey!"

They gave Melissa a quick hug. Jack looked sad and held his arms out. They reluctantly did the same to him. Strange, for a boy they thought.

"Those are really cool shoes" said Jack to Rhonda. "I haven't even seen those at the mall yet."

"Wow, someone noticed. I got them when I was in New York with my parents last week."

That broke the ice, and soon they were all talking together, chatting and gossiping, only the way that teenage girls can do.

* * *

That night when Jack got home, he took a shower. Not that he was dirty or anything, but as they four of them had sat on Melissa's bed and chatted, he felt so out of place. The other three had such nice, smooth legs, but his were hairy. He hadn't needed to shave for quite a while, so he didn't even know where his disposable razor was. He borrowed Becky's, which was in the shower, and he did his legs.

Once he dried off, he felt much better. He hated not fitting in, and sometimes when he was with Melissa, he would get so jealous of how she was dressed, or how she got to do her nails so pretty.

The next day, after Jack dressed up in Becky's clothes, he decided to borrow Becky's her, and try it on himself. Just to see how it looked. Melissa's nails had been so pretty, and her two friend's nails too. Only his had been dull and plain.

He decided to first do his toenails. After two coats, he moved on to his fingernails. It wasn't too hard to figure out. He was admiring his hands, when he noticed that he had missed a spot on his toe. He sat on the edge of his bed, and painted his toenail.

Just then, Becky walked in the door.

"Hey, that's mine!" she said.

"Sorry, I'll get you some at the mall today."

"Okay, just ask next time please?" she said.

"Sorry, won't happen again" replied Jack, not even looking up.

Becky shook her head. Little sisters were a pain sometimes.

* * *

Later that afternoon, Jack was watching a soap opera on the TV in his room, when Melissa walked in.

"Jack! Look at your outfit!" said Melissa, who was taking in the skirt and the blouse he had borrowed from Becky's closet.

"What do you think?" he asked.

"Those colors don't go together at all" she replied. And that top is way too tight on you. If your boobs are so large that they buttons are strained like that, then you shouldn't wear it."

"Really?" he said.

"Yeah, it makes you look slutty. Come on over to my place. I'll find something better for you."

They walked through the living room, past Jack's parents who were watching a movie. Jack's mother glanced at the outfit he was wearing.

"Is that Becky's skirt? She'll be mad that you've borrowed her clothes" she said.

"I'm going to Melissa's. I'll get one of her outfits, and then we might go to the mall."

"All right kitten, but don't stay out too late tonight."

"Aw mom!" protested Jack. He wasn't a young girl anymore! He was old enough to take care of himself.

It was so much fun to go through Melissa's closet, and pick out a really fun outfit. Jack found a little white tank top with thin straps, just like he loved. That and a short black skirt which really showed off his curves.

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