Bobbi's Point of View
When Jessi (it's funny how I think of Jesse as Jessi when he's dressed like that) and I met, I thought he was really cute... So cute that I pretended to have trouble with some of the tech stuff in school to get his attention. I was thrilled when he asked me out.
But I think I fell for him when I got him to wear my clothes the first time. I knew he was joking when he offered, but I was feeling a bit mischievous, so I held him to the joke. He not only actually did it for me, but he looked good doing it! And for some reason, it always turned me on!
But as much as his crossdressing for me turned me on, it was even more of a turn-on when I got him to come to sleepover as a girl. And then, he agreed to spend a week as a girl, so I've been almost climbing the walls.
But let me tell you what drove me past my limit. After Jessi had fallen asleep, Amy showed us a small cheap-looking brass medallion on a rusty chain. It could change people physically, she told us. She said that it would make people change to fit any new garments, or to the body of the last person who'd worn it if it wasn't new. She fastened it around Jessi's neck, and touched it to a corset that still had the tags on. Then the most erotic thing I've ever seen happened. I moaned slightly as I watched Jessi's little bottom flesh out a bit and huge breasts grow on his chest. Knowing to look for it, I could still he that he was a man where it matters, and the thought alone made me orgasm. Quietly, fortunately.