Masquerade of a Renegade

Katherine walked around the room, checking to see if everything was perfect. She had just finished dressing Dito in his best dress. She looked down at him and smiled.

"You look amazing tonight." She said, admiring her own work.

"Thank you, Auntie. I'm so glad you could help me with this." Dito replied, looking up at her shyly.

Katherine chuckled. "Don't be silly. You're my nephew and I love you, of course I'll help you with all your big plans."

Dito smiled at her, a little more confidently this time. Katherine returned the smile and turned to leave the room. "I'll be out front with your father while you get ready." She told him before leaving the room and closing the door behind her.

Dito was left alone in his dressing room to finish getting ready for his first night as a crossdresser named Lola. He pulled the wig over his head and let it settle on his head, then he slowly put on the finishing touches that would make him Lola: thickly lined eyes, bright red lips and a long blonde wig that reached down to his waistline.

"My God! I look good!" he exclaimed as he gazed at himself in the mirror wearing makeup for the first time as Lola. He felt so different from how he looked before; his whole body felt different, like it belonged to someone else entirely. He felt free, like he could do anything now that he was dressed as Lola. When he took off this dress and wig, he would be back to being Danny again, who mirrored what society expected him to be, who wore baggy jeans and hoodies everyday just because that's what everyone else did too, but tonight? Tonight was special because he wasn't Danny anymore. Tonight he was Lola, who wore beautiful dresses and makeup all day long because she wanted to express herself however she wanted to without worrying about what other people thought of her - both men and women alike! It was empowering in a way he never thought possible before tonight but now that he had experienced it once, there was no turning back for Dito!