Jon felt the breeze on his stocking clad thighs. The feeling was nice, he thought. The hem of the skirt was flapping on his upper thighs, and he felt great as his heels clicked down the sidewalk. He had his fingers entwined with Karen's as the two teens walked to school together.
"You look so sexy, Jon." Karen said to him, as she hugged his arm. Everything felt great to him, as she shook his ass while he strutted along with Karen toward school.
"Thanks, Karen." he said a bright smile on his face.
"You know, I'm really glad you wore the dress today." she said.
"Oh? Why wouldn't I wear it, when my beautiful girlfriend asked me so nicely." he joked to her, his breasts bouncing along, and almost spilling out of the top of his dress.
"Well, I mean, every other time I've ever asked you to wear a dress to school, you always told me no." she replied, holding him tightly.
"Wh-what do you mean?" he asked, his pace slowing.
"You always say that you're a man, and men don't wear dresses." she said.
"I-I do?" he said, his strut turning into a slow walk.
"Yeah. You're always telling me you only wear skirts and dresses for work, and that you don't want everyone to make fun of you for looking like a chick.
"What." he said, coming to a complete stop.
"what?" Karen asked, concerned.
"I don't normally dress like this?" he asked motioning to his sexy outfit.
"Gosh no." Karen smiled "But I'm really glad you decided to today. I'm sure everyone will accept you." She pulled him by the hand to the school which was only across the street now.
"Karen, I can't go to school like this, if this isn't how people are used to seeing me!" he reasoned, looking for an escape.
"Well, it's too late for that now, we're already here, besides, I'm sure they'll get used to it in no time!"
