you (for some reason) always wanted to see your roommate, scaramouche, in a dress or a skirt

It was his birthday and he was drunk when he was opening his gifts. As a joke, you got him a maid dress

he opened your gift and stared at the dress. Since he was drunk, he went to his room and put it on. He came back into the room where you and all the guests were, him wearing the dress

"How do I look?" He says in a drunk voice, striking poses