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Jestro looked at the dresses Macy laid out for him. "These are all for... me?" He nervously asked, "Don't you think it's weird a boy would wanna wear a dress?" He looked at the dresses. "...Do you think it's weird for a girl to like wearing pants then?" Macy asked. Jestro replied, "N-no, of course not! It's just..." What would people think about him? Wearing such things... Macy smiled, "I'm just teasing, Jes. Don't worry, I think you'd look nice in a dress," Jestro giggled, "Thanks, Macy." He picked up the dresses and left the Macy's room.
He got to his room without many stares from the squirebots walking by (why would a jester be holding some of the princess' old dresses?). He locked the door and gulped down his nervousness, why was he so scared of wearing a dress? It's just a piece of clothing.
Was it because it's something he's never ever tried before? He sighed and took off his clothes and changed into one of the dresses, a long navy blue dress. He looked at himself in the mirror and smiled. He looked so beautiful. He tried on another, they just felt so... fitting on his body. He never felt so good about his body before.
Then he put on a bit of make-up on his face (generously gifted to him by Macy), and he felt even better. He giggled, was this how a woman felt like? He wished he could wear a dress all the time without thinking people would shame him for wearing one in public.
Macy really was the sister (s)he always wanted.