Two days after he painted the matching nails, Anna went out with some friends, so he had the house to himself for the day. He read for a while, watched tv, and played games, but he didn’t quite feel right. He didn’t want to paint his nails, they were still perfect, but something felt off. As he walked by his sister’s room on the way to the kitchen to make lunch, he stopped. The door was closed, and even though he knew it was fine to go in, he felt like something would happen if he did.

Shaking himself out of his trance, he went to the kitchen. He decided to make a sandwich for lunch. He cut two slices of ciabatta, and then went to the fridge to get out the fillings. Placing down a cutting board, he sliced up a tomato, and some fresh mozzarella cheese. He spread pesto on both slices of bread, and then began shingling genoa salami, then the cheese, then the tomatoes. Content with the sandwich, he went over to the table and began eating.

After devouring the sandwich, he headed back to his room, but stopped again at his sister’s room. He wasn’t sure why, but he wanted, he needed to go in. He went inside. He looked around, not really sure what he was doing. He stopped, he looked down at his perfectly manicured nails. He loved them, but he didn’t feel content, but he didn’t know what to do.

“Maybe if I give myself a manicure and a pedicure, he thought.” He went to his room and grabbed his supplies. He knew he could have just done it in his room, but for some inexplicable reason, he felt like he had to in his sister’s room. He painted his nails and toenails white. Even though he really liked how they looked, he didn’t feel content. He looked around again, before stopping in front of his sister’s dresser. He knew he shouldn’t open it, but he felt like he needed to, like something in there would make him feel content. He tried to stop himself, but he couldn’t. Opening the top drawer revealed sets of bras and panties.

“They’re so neatly organized,” he thought. “I shouldn’t” He stood there for minutes, trying to restrain himself, but in the end he couldn’t. He looked through until he found baby blue bikini cuts and a matching bra. Each were covered with lace. He stripped down. He pulled the panties up his legs, smiling at their softness before putting them on completely, his penis tucked. He put on the bra, latching it like he had been doing it his entire life. There was a decent amount of padding in it, making it appear that there was something there. He felt better, but he still wasn’t content. He went into her closet, he knew what he had to do.

The wall of the closet were lined with clothing and accessories. On the left, there were hangers that dresses and skirts, on the right there were tops. He opened a drawer and it was filled with leggings, opened another to find jeans. This is what he needed. He went over to the dresses and inspected them, he had to find the perfect outfit. Pulling the first hanger out, he took a look at the dress. It was a black skate dress dress with pink and red roses on it and a scoop neck. He put it back.

“I’m going to have to look through all of these,” he thought. He took out the next hanger, which had a mustard yellow cami mini dress on it that would show his cleavage if he had any. “This definitely would look good with the yellow polish.” He put it back, pulling out another, it was a red t shirt dress with athletic stripes on the sleeve. “Very cute! I’d probably look great in that.”

He continued looking through the dresses, and then the jumpsuit, and leggings, and so on, but he couldn’t make a decision, as if he had to look through all of the clothing first. As he was looking at her sweaters, he heard the door creak very quietly. He froze, but clearly made too much noise. The door to the closet swung open, his hand still on a sweater on the back wall.

“Excuse me miss, how did you get into the house?” Anna asked. Julian stood frozen. “Wait, a minute. Julian. Turn around.” He let go of the sweater and turned towards her, head looking down in shame.

“I-I-I-I’m sorry,” he said, “I just suddenly had an urge. I didn’t try anything on, all I did was put on this underwear…”

Anna cut him off. “You look so cute and girly! Now why don’t you calm down, let’s find you something to wear.”

“You-you-you’re not mad?” he asked in disbelief.

“Why would I be? Would I have preferred if you had asked me first, yes, but I’m not surprised considering how much you are tapping into your feminine side!” she giggled.

“Oh, okay,” he grinned and sighed in relief

“Now what do you want to wear? Hmm, let me guess actually.” Before he could say anything she had made an outfit. It was the cute athletic t shirt dress and a pair of red converse as well as fishnet stockings and ankle socks that were flipped colors of the dress. “You’re going to look so adorable in this! Put it on!”

Julian was amazed, she had found the perfect outfit for him. He took the fishnets first.

“Actually, wait. Come with me,” Anna said. He followed her to the bathroom, still just wearing the cute bra and panties he had picked out.

“Why are we here?” he asked.

“There’s no way I’m letting you wear a dress with even remotely bare legs unless we shave them. Hairy legs would ruin the whole outfit. And you know what? So would hairy arms. Come on, you’ll love how it feels.”

“O-okay,” he said with hesitation. “I mean I guess I do want to look my best.”

“Good!” she said. “Let’s get started.”

Anna helped Julian shave, making sure that no spot was missed.

“Wow, they’re so smooth,” he said, rubbing his legs.

“See, I told you that you’d love it!” she giggled. “I would ask you to trim your bush lol, but we don’t need to do that!” she started laughing and he laughed along nervously “yet,” she muttered under her breath.”

They went back to her room and he began to get dressed.

“Be careful with the stockings! I wouldn’t want you to rip them.”

He very slowly put them on, shivering a few times because of how they felt on his bare, smooth legs.

“These feel so nice,” he said.

“Good!” she said, smiling. “Now let’s get this dress on, you’re going to look so cute when we’re done!”

He put on the dress, looking down and seeing two bumps poking out of it because of the padding in the bra. He then put on mid ankle high socks with athletic stripes, inverse in color to the dress, followed by the shoes that matched the color.

“Why don’t you come over here and take a look at yourself!” she said, smiling.
He went over to the mirror and took a look. He gasped. He looked so cute, but there was still something off.

“Hey, my hair is pretty messy, we should do something about that,” he said.

“You’re totally right,” Anna said. “I’d be happy to style it. Come sit down at my vanity dresser.”

She began to brush his shoulder length hair, getting all the knots out.

“You really need to brush your hair more often, it would be so much better for you.”

“Yeah, I do. I think I will be now, especially if I want to look cute like thi-” he cut himself off.

“Oh, stop being silly. I know you like this, you’re literally wearing a dress, not because I suggested it, but because I caught you in my underwear. You’re being ridiculous.” She smiled at him as he looked into the mirror. Now, what do you think you would like better, a bun, braid, or pigtails?!” she asked.

“Uhhhh, hmmmm. I don’t know,” he said, thinking. “Wait!!! Actually I do!”

“Oooh, what do you want, I’m excited to know.”

“So, uh, girls at school with short hair like mine will braid theirs into two short pigtails, and it’s really cute!”

“OMG, that would look so cute with the rest of your outfit! That’s so perfect!”

Julian beamed with pride from that compliment as she made the pigtails.

“There, how does that look?” she asked.

“That’s exactly what I was looking for!” he said. “You’re right, me still trying to pretend like I’m not enjoying this sometimes is definitely stupid!”

“It’s good to hear you say that! I think we should go out to dinner, you’re so cute that it would be dumb to not show you off!” she exclaimed.

“But what if somebody recognizes me? That would be devastating!” he said in a nervous tone.

“Hmm, we can definitely make you unrecognizable, you’d just have to let me do your makeup.”

“Yeah, I guess I’d be okay with that.”

“Why wouldn’t you be? It isn’t any different than painting your nails in the end! If you like it, I’ll teach you how to do it yourself another time!”

“Alright, let’s do it!”

…. To be continued

What do you gals think?? I'd really appreciate feedback, or even suggestions on where to go next!