Pretty Woman

His mother, taking full advantage of being married to the Governor with lavish shopping trips, often left her only son to his own devices while she shopped and gossiped with her friends, all as well-to-do as she was. So Tyler spent a great deal of time playing quietly among the racks of designer clothing. His taste for soft, silky things carried over to his adolescence, and earned him a reputation of "fag" when he came to school carrying a large purse that he had innocently mistaken for a sling tote. Throughout middle and high school he learned to be invisible, getting average grades and not making any effort to socialize at all. Thus, he managed to graduate in one piece, hiding a huge secret from the rest of the world. While most boys his age were just interested in getting to what was UNDER a girl's bra, Tyler took his time. He caressed the smooth fabric covering her body, memorizing the texture of soft cotton blouses and, under that, lacy bra cups. Despite having snagged a handful of girlfriends, the rest of the male population still thought he was gay, so eventually Tyler had given up trying. For awhile he had drifted listlessly, until the day he found that the spare room downstairs had been emptied into his attic bedroom- including boxes of Emily's clothes. The thought of actually going to a store and trying on women's things had been terrifying to him, but here was a ready source to feed his fantasies.

Now, as he stood admiring the way he looked with a properly stuffed bra, Tyler was in heaven. His fingers drifted lazily down the false profile of a woman's shape he presented, squeezing the padded bra and imagining what it would feel like to have proper breasts. Next came his flat stomach and hips, hands tracing the line where silk met cotton. Twisting a little, he smiled briefly as he admired the way wearing a skirt made his pert ass look pretty damn fantastic. There were seams down the back of his stockings, innocent and yet somehow arousing as hell with just that little detail.