Pretty Woman

"Alright, but I want you two to remember something: whatever you do, affects me. So behave yourselves!"

"Thanks Daddy!" Emily chirped, and Tyler found himself being dragged out the door with barely enough time to grab his jacket against the cold night air outside. He was herded into Emily's Mercedes, and sat with a lead ball in the pit of his stomach while she seemed totally carefree, singing long with the pop music blaring from the speakers.

At the apartment of Emily's long time best friend Shay, Tyler stood awkwardly in the living room while his sister chattered away with her friend, until she motioned him over. "So we're going out tonight, and Ty's coming." Emily said. "As it turns out, little brother has a thing for women's clothes." Shay looked completely unsurprised, and grinned slyly up at him as he blushed furiously.

"Emily! Jesus! You're so blunt." he hissed, only to be waved off and dragged towards the bedroom by Shay, normally any red-blooded American man's fantasy. The pretty redhead had what most considered a knockout figure, going in and out in all the right places while snug fitting clothing only served to put her assets on full display.

"Emily's gonna hang out while I help you get dressed so it isn't too awkward, okay?" Shay said as she released his wrist and started digging through her drawers. "Take off your clothes hon let's see what I've got to work with." Tyler opened his mouth to protest, but just then she held up a pair of mouthwateringly sheer panties, and he silently undressed, standing naked in the middle of her room with his hands folded modestly over his half hard cock. Shay was tossing through her clothes left and right, and finally she turned back to start handing him things. Tyler pulled sheer black panties up his legs, feeling his cock twitch to life at the sensation of smooth fabric against his bare skin. Shay glanced down, giggled, and glided over to help him into the matching bra she had in her hands.