The next day, Jon met Madison out in front of his house. The previous day had been a whirlwind for him. Having his hair styled, and his face made up, had put him in a different mind set, and it seemed Madison was doing everything she could to push him across the line into womanhood. He stood, waiting for Madison, in a schoolgirl type outfit. Short Blue skirt, thigh high stockings, high heeled leather shoes, and a tight white top with long sleeves and a short middriff. He felt oddly comfortable, having done his hair and makeup this morning himself, he felt that no one would know he was really a boy, and felt at ease as a girl.
"Hay, sexy!" Madison called out as she sauntered up to him in her identical outfit. She planted a kiss right on his lips, and slipped her hand under his skirt to grab his pantie covered ass.
"Hi Madison," he said softly with a smile.
"You look so fucking sexy today, Jonnie." she said as she ran her hand across his bare stomach.
"I think you look way better, Madison." he said admiring her body. "But I don't recall you ever wearing anything like this before. You used to just wear baggy pants and shirts...." he pointed out.
"Well," she admitted "Every since you lost that bet, I just can't help myself. The thoughts of you in these outfits turn me on so much, I wear them just to see you in them." She smiled again as she leaned in and gave him another passionate kiss, this time squeezing his breast."
"Hi Madison...." a voice said from behind him. "JON!" He turned in shock to see...
"Karyn!" he squeaked in surprise. He hadn't expected for her to see him like this.
"Holy, SHIT." she said mouth agape.
