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.