Pretty Woman

Tyler was as nervous as anyone could be. Hazel eyes darted for the door as silky black stockings slid up smooth white legs to meet garter straps attached near lacy white panties. Next came the bra, straps catching on skin slightly sticky with perspiration. Heart pounding as the black pencil skirt glided into place low on lean hips under a sheer white blouse. Lipstick in a shade of modest red slicked a pouty smile even as Tyler jumped at every little noise from downstairs. Mascara and eyeliner helped the hazel eyes to really pop, and as the eighteen year old boy stood back, there was a feeling of absolute rightness in his chest. He smoothed his hands down the front of his skirt, turning this way and that to admire the way he looked in the attic's full length mirror.

These were his older sister's clothes, but they fit him just right, even if the empty bra cups looked slightly odd in their deflated state, and the stockings had a run in one of them. Briefly, Tyler wished he had a pair of heels to complete the look, but his sister had smaller feet than he did so he was out of luck. As it was, the sheer fabric of his stockings molded perfectly along the sensual curve of his legs, and that was enough to get him hard. That would never do, he thought as he noticed the tent start to form in the front of the skirt. Shoving a hand under it, he found the rigid length of his penis and, with some creative rearranging, managed to tuck the offending organ up between his legs, held there by the snug fit of the panties he was wearing. Feeling silk and heavenly soft cotton against his bare skin made him exquisitely aware of his every move as he stepped to one side, peeking briefly out the window to make sure the driveway was still empty before he went back to rummaging through the boxes that had been left when his sister Emily went to college a year ago. A smile touched his red lips as he found a string of pearls, fastening them around his neck and returning to the mirror.

From an early age, Tyler had been good at entertaining himself.