He resigns himself and asks for the dress

It was tearing him up to risk owing his sister something, but he couldn't imagine wearing the ridiculous t-shirt and scandalous micro skirt. He was doomed to be made fun of either way for wearing girls clothes either way, so he thought it would at least be better to pick whatever would cover the most.

"I'll... I'll take the dress... But please ask for something reasonable for the favor. I'll do your chores for a month if you want, just don't make me do something embarrassing..." he begged her. He was embarrassed to have to beg his sister to let him wear some girly clothes.

"You don't get to set conditions, bro. I'll ask for whatever I want, so you either want it, take what I had picked for you, or I go tell mom that you would rather go naked than wear my clothes. And I don't think she will let you change your mind if I do. So what is it?" She had given him an ultimatum and he knew that she had the higher hand.

"Can I at least know what I will have to do before picking?" he asked in a last resort.

"No and if you don't pick now I'll go see mom." She warned him. Owing her an unknown favor was horrible, but less so than going to school naked. He just grabbed the dress and began putting it on.

"Good choice, we'll have a lot of fun later." She laughed.

K-T undid every button on the dress, this would be a tight fit and he wouldn't trust the fabric to hold if he tried to slip into the dress with the buttons closed.

Of course when it came to closing the buttons back, it was easier said than done, the flow summer dress he remembered his sister wearing a few years back looked like it was molded on his body and he had to stretch it quite a lot to get any of the buttons closed. Most of the buttons on the top half and the one at the very bottom, about a handwidth above his knee, were fine. But to his horror the two next to last buttons were simply missing and they were the ones lining up with his crotch.

K-T couldn't understand why his sister had kept a dress that no longer fit her and had buttons missing, or why she hadn't had the buttons fixed if she wanted to keep it. While standing straight up and with his dick soft, the dress would remain closed, mostly. But he was afraid of what would happen if he got hard again or when he would sit down.

"Emily, it's broken. There are buttons missing! I need something else!" he begged.

"Listen, you asked for something long enough to cover and you got it. We have a deal. Now if you don't want it you get nothing and you still owe me, now that your dick has touched it it's unwearable." She told him.

He knew that arguing more wouldn't end up in anything good and he had to hurry to not miss the bus. They went down and he grabbed shoes and school bag before going out to take the bus. All he got from his mother was a stern nod, he knew that she didn't care that he had to wear girl clothes. She had given him pretty much everything his sister didn't want anymore and that fit him for years. The only reason he wasn't given dresses and skirts is because he refused to wear them so far. With his habit of losing or destroying them, his mother had decided that buying him his own clothes was pretty much a waste of money.

He reached the bus with barely a few seconds to spare and clad in a green dress with a pink flower pattern, he got into it, holding his school bag in front of his crotch.