A noise from below reminded Henry that he was still expected, and unfortunately, he didn't really have time to figure out what was going on. He was just going to have to put on the damn clothes.
First was the underwear. A lacy golden silk thong that was just barely large enough to conceal his cock, but which was so tight that it left no questions about what it was hiding, followed by a garter belt and a pair of long golden stockings.
Something downstairs thudded, and Henry remembered that he was supposed to be on a deadline. As much as he hated wearing all this, he hated the idea of being naked when this supposed "Mister Winters" took an interest in him even more. Next was the... other thing. The thing that Henry desperately didn't want to admit was a dress. The thing that most definitely WAS a dress.
He took a deep breath, and began to work it up his legs. The green satin felt like lightning against his skin. The dress was short and sheer, and left very little to the imagination. It was armless and backless, held up only by the straps that wrapped over his shoulders, with a narrow v-neck that plunged all the way to his hips and a hemline that ran only a few inches lower. Finally, there was a leather belt, embroidered with gold and set with an emerald, that tightened the dress around his waist while resting on his hips.
Then came the gloves, made of golden satin that ran halfway up his arms. Then a golden choker clasped around his neck. And finally the shoes - green, with a stiletto heel. As he stood up, he though for sure he'd never be able to walk in the damn things, and yet he found he kept his balance with ease, as if he'd been wearing them his whole life.
He looked into the mirror and gasped. Standing before him was... not a girl, exactly, but what a boy would be with a girl's beauty and sexuality. He stood with a natural sway to his slender hips ever-so-slight wasp waist above them. His dress barely concealed his package, and the V-neck pointed towards it like an arrow, place it tantalizing just out of sight. His now waist-length hair hung loose, and he quickly tossed it over one shoulder to give it a slightly more presentable appearance. Everything about him - EVERYTHING - was seemingly perfectly calculated to celebrate and present his body as if it was a divine gift to the human race.
Somebody knocked on the door. "Come on, Henry!" the boy from before said, "We need to get moving, now! The guests just arrived!"
Henry shook his head to clear his thoughts. "Coming!" he shouted, and for the first time he realized how high his voice was, as if he was still a young boy. With a practiced grace that disturbed him, he minced over to the door and opened it.
As familiar as the voice was, Henry certainly didn't recognize the boy who was waiting for him outside. He was about Henry's age, with olive skin and black hair he wore in a bob cut. His clothes were similar to Henry's, but all in red rather than green and gold, and with a ruffle skirt rather than Henry's plain one.
"Mister Winters is waiting for us," the boy said, and with a shock, Henry finally recognized his voice. It hadn't sounded like that in years, but the two of them had spent enough time together for him to recognize his best friend anywhere.
"Wait," he said, "Michael?! Is that you?!"
Michael glared at him. "Uh... yes?"
"What are you doing here?!"
"...did you hit your head or something?"
"But you're supposed to be back in..."
Michael rolled his eyes. "Come on!" he said, grabbing Henry by the wrist, "we need to get downstairs and into the lineup before our guest arrives."
Henry was mostly just too confused to protest as Michael hauled him to the stairs, and the two of them descended into what Henry was now beginning to recognize, with a rising anxiety, was the Devil's Inn - the whorehouse that Carol worked in.
...gods above, he was a WHORE.
The stairs came out into the main hall, where a number of boys were already lined up to greet whatever special guest had gotten "Mister Winters" so worked up. A middle-aged man, who Henry assumed must be Winters himself, wearing a brightly coloured but much less provocative dress of his own, stood by the front door, eagerly awaiting the arrival.
"Come on!" Michael said, and the two of them quickly took their place at the closest end of the line. Mister Winters let out of a sigh of relief as the door creaked open and the guest of honor entered...