Chapter 1
Hermione took a deep breath and mentally went over her safety checklist again. Locking, silencing and obscuring charms protected her prefect's room from anyone intruding or discovering her activities without a great deal of effort that would give her time to react. On her bed lay an outfit of ordinary muggle clothing from her own wardrobe, a button up blouse, a pair of trousers, her school uniform tie, underwear and a pair of socks. First she performed a simple transfiguration on the shirt and slacks, changing the buttons and fly over to the other side, the way men's trousers were made. She was also careful to toy with the cut a bit, taking out the girlish curves from the shirt and pants, making them into a set of stylish male clothing. Then, with a bit of mischievous delight she turned to the simple pair of cotton knickers. In order to pull off her little game, everything had to be just right.
She considered the different kinds of male underwear...although she'd seen bikinis and thongs in the men's section at department stores she didn't think that was right for this sort of thing, and so she debated between boxers or briefs. Again the possibilities were fascinating... she'd always been intrigued by the shape and construction of men's briefs, with the pleasing waistband and hole in the front...but then again boxers were equally as exciting with their fly and loose legs, a much different experience than wearing briefs which would probably feel very similar to her own usual woman's knickers. Finally Hermione decided to compromise and transfigured her underwear into black boxer-briefs that had the pleasant design in front to allow certain appendages air without taking them down, as well as being form fitting, but with the unique extended legs continuing onto her upper thigh. Hermione quickly removed her dressing gown under which she wore nothing and slipped on the masculine underwear with a thrill.
Her breathing quickened she was so excited, Hermione turned to her mirror and growled in frustration when she saw her breasts and long fluffy hair contrasting with the masculine underwear. While it was a rather kinky sight, it wasn't what she was going for at the moment. Hermione frowned at her chest... having a smooth chest to go with the male knickers would be so much sexier than having to bind herself down with bandages. Hermione ran her hands over her small but noticeable breasts squashing them down and felt a thin wooden rod sliding over her sensitive nipple. She jumped a bit at the sensation realizing she was still holding her wand then laughed with excitement! Magic of course! Having a kinky pair of gay male friends who enjoyed drag, she knew that both Draco and Ron had given themselves quite realistic temporary breasts. Wanting her transformation to be a surprise she didn't want to ask them for help, but at least she knew it was safe and reversible. Concentrating hard she drew her wand in circles around each breast watching the mounds diminish until nothing was left but a flat smooth boyish looking chest.
Hermione gathered her hair into her hands and held it back admiring the sexy male figure she now cast. Similar to her chest, Hermione now transfigured her hair drawing much of it up into her wand making it shorter and shorter until it only grazed the back of her neck where her collar would be. Pulling a jar of sleakeasy potion out of a drawer she then scooped out a bit - quite a bit less than was necessary when her hair reached down her back, and worked it in marveling at how her curly hair relaxed. She didn't go for absolutely straight however - as sexy as it would be, she left a bit of natural wave in the remaining hair to give it a tousled look as it hung. Adjusting her posture a little bit, Hermione let out a genuinely cocky laugh as she gazed at the mischievous looking young man reflected in the mirror. The lack of muscle definition and slight curves made her look almost prepubescent, but definitely male, and definitely attractive.
The view got better and better as she dressed until finally she stood in full masculine attire knotting her tie (turned black) loosely so it looked sharp but casual. She was just noticing that the pants didn't fit quite right when a gentle male voice broke the silence and said, "I think you're missing a rather vital piece of equipment."