Brian was a little shocked when he found his girlfriend trying on his clothes one afternoon. She'd called telling him she was off work early and would pick something up for dinner meeting him at his place.
He'd decided to get off early and spend the afternoon being playful. Those plans changed a little when he found her standing in front of his mirror in his shorts and tee-shirt.
He wasn't prepared for her confession either. She'd been doing it all of her life, from the age of six or so. Three brothers and a lot of hand me downs some of it she said but there were often other urges. Mostly it was just that proverbial "grass is always greener on the other side" sort of thing.
She just liked the way boys things felt on her. That slight coarseness in boy's clothes that gave her a light sense of masculinity. An opportunity to spit on the pavement or cross your legs without having to keep your knees together. Brian wasn't sure if he would ever fully understand it and said as much.
He did like Julie and there was no question over that, and if that sort of thing turned her on then he could live with it. He did ask questions about it. How it made her feel, what went through her head when she started dressing and that sort of thing, but she couldn't explain all of it.
The idea, when it came made him laugh and of course he said no. Just a pair of panties and a slip she'd said. Something sensuous and a reason to be playful she'd added that rainy Saturday. He did finally agree and there was a whole lot of understanding on that day.
Brian also began meeting other people that Julie knew in that world she walked in dressed as a male. Most females, but some males. The dinner at one of the largest clubs down town was a formal affair to raise money for Charity. One hundred dollars a plate but, more importantly also a reason for everyone to dress up.
Julie wanted to go. She also wanted Brian to go with her. Brian was a little turned off by the whole idea of what she was suggesting. He had liked her panties and slips and that nightgown he'd worn to bed one night but this was a bit much and he'd said so.
Although finally he did give in and more for the sake of her than for any other reason. Which lasted for a time as they shopped. It was his first dress and how odd that sounded as he stepped out of his first bubble bath. First pair of panties, slip, bra and silk nylons to wear with his low heels.
That whole evening was a list of first for Brian as he swished through their night together. By evenings end he was nearly faint when the long black sedan they'd rented brought them home. He hadn't once opened a door, nor pull back his own chair. He hadn't danced once as a male nor did he use their bathrooms.
He also didn't have to undress himself and of all the reason for that lingering kiss, that most of all, was worth it. He woke in his long flowing "A Bride's First Night" negligee with it's matching robe, and found his girlfriend Julie in his new silk pajamas fixing breakfast. They kissed and breakfast was put on hold as were most of Brian's objections over men doing what men shouldn't do.