Sammy let out a small sigh of relief. Well, that was good. This thing was pretty ridiculous wear even now. He felt nervous suddenly again, and crossed his legs to hide his small manhood for a moment longer, at least. She offered him a small bag, and Sammy took this as the time to change back into the ridiculous leather pants he had come with. He did so in front of her, though he tried to be quick about it. A surprise?
He'd be very surprised if it wasn't a dildo, the way this was going.
"Well, I'll think about it when I'm out... uhm..." He said, grabbing the bag. "Thanks for giving me a shot, Miss Wright."
Made up like this, as long as he didn't get hard and nobody looked too closely, he could pass for a girl. He turned to leave, slowly slipping out. He milled around for a few hours at home, contemplating life and what exactly he had gotten himself in to. He weighed the pro's and cons here. Miss Wright had the clout and influence to take him places he could have only dreamed of going if he did this. But that same influence could be used to blackball him, and make sure that he could never get somewhere without... dressing and acting like a woman. And then there was the matter of his arousal at what was happening. He shouldn't have been getting hard about a woman wanting to make him into a girl, should he?
Finally, he caved. He left his apartment and went on a shopping spree with the money provided to him. The beauty products were the first things acquired -- he figured those would be pretty expensive -- and the rest was spent on clothing. He was about to get about two of everything. Two panties, two... bras... two skirts, two short shorts, two shirts, a tank top -- one set of girl's shoes, which were sized differently than mens and gave him some issue for a moment or two, and then a pair of heels. And, of course, a dress and a chemise.
All these things, and nobody stopped him once. Nobody gave him a strange look. And the strangest thing was he almost had fun going on this ridiculous shopping spree with no one the wiser.
He slept in that chemise that night, and he had to wash it the next day; he couldn't stop himself. He rubbed one out into his panties, just imagining the situation he was in and looking at himself in a small mirror. He had to wear the other to Miss Julia Wright the next day.
He wore the dress -- a black, strapless one -- blue heels, and underneath a pair of pink panties. He didn't wear a bra, but he didn't think she'd come after him for that. Lot's of girls didn't wear a bra with a strapless dress, right? He knocked on her office door that day, at 11 o'clock sharp. He was going to be famous, damn it, and he was going to see just how far Julia Wright was planning to take this. He hoped it wasn't some kind of sick joke.