It was late, and Andrew wanted to go to sleep, but he needed to get ready in the bathroom. Unfortunately, his sister was busy taking a shower. This was a regular occurrence late at night, and it was extremely annoying. He got impatient, so he knocked on the door and said, “Emma, can you please get out? I’d really like to get to bed.”
“Give me a minute,” responded Emma. “I’m almost done. I’ll be out in like 2 minutes.” A few minutes later, she left the bathroom. He headed in, and began to brush his teeth. Behind him he noticed a pile of clothing. He kept glancing at it as he continued his bedtime routine, feeling a very strange urge growing in him. As he was about to leave, the urge consumed him. He approached the pile, separating the different articles of clothing. It was what his sister had been wearing earlier today: A pair of grey sweatpants, a black cami, and a grey calvin klein bralette & panty set. As if in a trance, he stripped down, and started to put her clothes on. He tucked his penis back, giving the image of a flat crotch under the soft panties, and then put on the bralette. Before he put on anything else, the urge subsided. Looking in the mirror, he couldn’t help but feel feminine. He turned slightly to the side, appreciating how his butt looked in the panties. He almost enjoyed how feminine he felt. He shook his head, dismissing the thought, and he changed back into his clothes, finished getting ready, and went to sleep
The following Saturday, Andrew had the house to himself, as both his parents were away at a conference for a week and his sister was staying at a friend’s house. He was just finishing lunch, and after cleaning up, he began to head back to his room to get back to work. As he walked down the hallway, he noticed that his sister’s door was open. As he passed, he saw something in the corner of his eye that grabbed his attention: her closet was open, revealing a lot of her clothing. Suddenly, that strange urge began to grow again, and Andrew walked into Emma’s room. In a trance, he went over to the closet and began to look at her clothes. There were crop tops, tank tops, t-shirts, bodysuits, rompers, skirts, and dresses. His focus swiftly turned to the dresses and skirts, looking through them. He needed to find something feminine, he just wasn’t sure why. As he looked through the dresses, he saw a variety of options: A light pink t-shirt dress, a red bodycon dress, a black fit and flare dress with a white and pink floral print on it, and more. He questioned how he knew what type of dress they each were, but quickly dismissed it as normal. He decided on the floral dress. He put it on his sister’s bed, and headed to her dresser. He opened the top drawer to see all of his sister’s bras. There were at least 15, all ready to fit his sister, but he instinctively grabbed one, taking his shirt off after he put it down. It was smaller than the rest, a push up A-cup bra that she probably just missed. It was black and had lace trim, and he put it on like he had been doing it for years. The padding was comfortable, and pushed up fat that he hadn’t noticed before to a respectable C cup. The soft cloth felt nice on his nipples, which had been more sensitive lately. For a moment he thought that he might be growing breasts, but he dismissed that idea, saying that he just was a little out of shape. He then put on a matching pair of panties, which were very soft, again instinctively tucking his penis back. He walked over to the bed, his chest jiggling in the bra. He put on the dress, zipping up the back with ease. He then headed back to the closet, and looked at the rack on the floor. There were three levels on it, each for a different set of shoes. The top was casual: sneakers, flip flops, and boots. The middle was dress shoes, both heeled and flat. The bottom row was sandals, again both heeled and flat. He went through the sandals, looking for something casual but feminine. He eventually chose a pair of gladiator sandals with a medium heel. The straps were black, and the heel was a tan color. He put them on, and was able to walk in them with ease. He headed over to his sisters mirror, the skirt of the dress swishing on his oddly smooth feeling legs as he walked. His walk felt feminine, but he liked it more than his usual walk. He walked over to the mirror, and looked at what he was wearing. He loved it. He inspected the dress, looking at the red and white roses printed on it. He twirled in it. He loved how feminine he felt. He couldn’t believe it but he truly wanted to keep wearing the outfit. He wore it the rest of the day, enjoying everything he did a thousand times more, until he knew that his sister was coming home soon. He went back to her room and took some pictures of himself, posing in such a way to show of his cleavage and his ass, like he has seen girls do on instagram. He then changed out of the shoes and the dress, making sure that he put everything back carefully. He stood there for a moment in his sister’s bra and panties, almost unable to take them off. After moment he took off the bra and put it away, but he couldn’t bring himself to take off the panties. He put on his regular clothing, putting his usual underwear in the hamper, and went back to his room.
When his sister came home, they at dinner together.
“How was your day?” Emma asked.
“Fine”
“Did you do anything fun?” Andrew got scared. He had to fight his body to not tell his sister. For some reason he just wanted to tell her and put the clothing on right then. Instead he just said “no I just watched TV and played some games.”
“Alright”
A couple of hours after dinner, Andrew went to bed. He put on his pajama pants, enjoying how they felt on his panties, and then put on a shirt. In his sleep he dreamed of being able to wear girls clothes all the time. Though it was a good dream something felt wrong, he just couldn’t place it. When he woke up in the morning, he had never felt more happy. He got out of bed, and as he headed to breakfast, he noticed that everything he wore was a bit snugger. “How am i getting so out of shape?” He thought. “I’m going to exercise today.” He went outside to the kitchen to find his sister making breakfast.”What are you making?” He asked after saying good morning.
“Chocolate chip pancakes for the both of us. I think it’s a perfect start to a day to spend together. I feel like we don’t spend enough time together.”
“Yeah, I guess. What’s the plan?”
“I say we watch a movie or two and then you choose something to do. So you have any ideas?”
“No, but i’ll think of one.”
After a nice breakfast, Andrew went to his room to change. It had occurred to him that if he bends over his sister might see the panties, and he didn’t want to take that risk. He changed into normal boxers, almost feeling disgusted by their lack of comfort as he put them on. He couldn't believe it, but he wished he could wear panties all the time. He put on a pair of jeans and a T-shirt, all of which felt weirdly uncomfortable. He went to the living room and let his sister choose a movie. It was pretty long. Both of them enjoyed it for a while, but eventually Andrew stopped paying attention. Not only was his lack of panties causing that urge to grow, but his uncomfortable clothing was scratching his skin, especially on his chest and nipples every time he moved. When the movie finally ended, his urge was consuming him, to the point where he didn’t feel discomfort anymore.
“Did you think of anything to do?” asked Emma. “If not, I have some possible ideas.”
“I’ve always sort of wanted to see what it’s like to have a manicure and a pedicure,” Andrew said shyly, though secretly extremely eager. “I’d gladly give you one. They always feel great, and they make me feel great afterwards because my nails are so beautiful,” responded Emma, clearly excited to do this. They went to Emma’s room, which greatly excited Andrew, allowing him to ignore his great discomfort on his chest. She had him sit down on the floor while she got her supplies. She came over and sat down, carrying a box. She opened it up, pulling out her supplies: nail clippers, a file, and a base coat polish. “How long do you want your nails to be?” asked Emma.
“Long,” responded Andrew, just noticing how long his nails were, smiling with glee at the thought of how feminine they were going to look.
“Alright,” said Emma. “Put your hands on the floor so I can reach them.” As she grabbed the file, he stuck out his hands. She held his right hand and filed each finger into an oval shape. She then repeated this with his left hand. “Before I put on the base coat, look through the box and choose what color you want your nails to be.” He looked through the box, finding that he loved so many of the polishes, particularly teal, turquoise, coral, white, baby pink, and baby blue. He finally chose the pink, as it was clearly the most feminine.
“I’ll have this color,” said Andrew.
Emma began painting his nails with a clear base coat. He was surprised by the cold feeling, but he very much enjoyed it. About 15 minutes later, his fingernails were done. After Emma asked him if he wanted a different color for his toenails, to which he responded no, she began the pedicure. Andrew didn’t really pay that much attention, as he was to busy staring at his nails in glee as well as trying to ignore his irritated skin. Emma noticed this. “What’s wrong? Are you not enjoying your nails?” she asked.
“No, I am. My clothes are just feeling really uncomfortable for some reason, particularly on my chest.”
“Could I take a look?” asked Emma, “I might be able to help you, I just finished the pedicure anyway. Could you take your shirt off?”
“I guess,” said Andrew, taking his shirt off. Emma was surprised.
“What the fuck, he has breasts!” thought Emma. “How is that possible?” She realized there was only one option, and she was going to have to play it off as something else. “You’re skin must be just a little sensitive because you’ve gotten a bit out of shape. I think that I have something to help you, as long as you're not uncomfortable with wearing some of my clothing.”
“If it helps, I guess I’ll wear it,” said Andrew, feigning reluctance.
“Alright, let me just find it.” Emma went over to her bra drawer, and rummaged through it, until she pulled a bralette it out. It was striped and was a racerback. Andrew put it on, but it felt too tight.
“This doesn’t fit me,” He said, taking it off. His chest jiggled painfully.
“Let me find something else then.” She rummaged through the drawer again until she found the bra that he secretly was wearing yesterday. “This is a push up bra. It’s going to make it look like you have boobs. Are you okay with that?” she asked.
“Yeah it’s fine, as long as it helps,” said Andrew.
“I doubt that you know how to get a bra on, so let me help you.” She helped him put in on, making it as comfortable as possible. “Does that feel any better?”
“Yeah, actually a lot better.”
“Didn’t you say that the rest of your skin was irritated too?”
“Yeah, just not as much as my chest was. It still is really annoying, though.”
“Alright, give me a minute,” said Emma, walking over to her dresser. She pulled one thing out of each drawer going down, except for her bra drawer. She layed out the clothing on her bed, motioning at Andrew for him to come over. He looked at the bed and saw a pair of black spandex panties, heather grey leggings, and a white tank top. “It’s going to be the most comfortable if you tuck your penis. Andrew did that, before putting on the rest of his clothing.
“Thanks, this feels a lot better,” said Andrew, glancing over to the mirror to see that in every way except his face and his hair he looked like a girl.
Andrew and Emma spent the rest of the day playing board games and watching movies. Andrew really enjoyed because he felt feminine, and a lot like his sister. He couldn’t help staring in glee at his nails and chest. Emma, on the other hand, was concerned. She was pondering the theory that he might be turning into a girl. She eventually decided that it was ridiculous, and unless there was more evidence she would completely reject it.