Five Days to Sissy

MONDAY

Alan woke up and found a note on his dresser, beside a small pink box. “Your journey has begun. By Friday, you will have a new life” the note read. He opened the box and discovered a pair of panties—girl’s panties, pink, with ruffles and bows…and another note: “Strip to the skin, put on these panties and then come see me in my boudoir—Stepmother.”

In the six months since his father had remarried, Alan had learned it was useless to argue with his stepmother. She thoroughly dominated his father and was determined to do the same to Alan. Blushing all over, he did as instructed, and found that the feel of the silky panties on his bottom and genitals was quite pleasant…and more than a little arousing. He struggled to hide his erect cock as he walked down the corridor to his stepmother’s room. He knocked and waited for her to reply. “Do come in, Alan, dear,” she called.

As he entered, she sat up in her luxurious bed, wearing a negligee that did little to conceal her voluptuous form, which only increased Alan’s arousal. He walked in cautiously, careful to keep his hands over the bulge at his crotch. “Oh, stop it, Alan,” his stepmother scoffed. “I know perfectly well how those panties affect you. After all, you’ve been stealing mine for the past month!” Alan gasped and started to protest, but she simply continued. “You thought I didn’t know? Darling, nothing happens in this house I don’t know about. The laundress reported finding my scanties in your hamper weeks ago!”

She stretched languorously, which merely made her superb breasts more obvious. Reaching for a bell, she summoned her maid. “Violet, you will find a selection of underwear in the bottom drawer of my dresser. Pack them up and move them to the drawer where Master Alan keeps his underwear. You may dispose of those masculine items, as Alan will no longer need them.”

“Yes, ma’am,” the maid replied, tittering with laughter. Violet glanced at the young man, clad only in the frilly pink knickers. “I hope you keep Master Alan dressed just like this from now on,” she said, smiling.

“This is how Alan will dress each morning, Violet,” his stepmother answered. “I will direct you each day on the clothes to lay out for him…but he will remain in only panties until I have decided on his attire. For today, find the lavender shirt and the very tight jeans in his wardrobe and lay them on his bed.”

“Yes, ma’am,” the maid said, and exited, snickering.

“Really, Stepmother, “ Alan pleaded, “what will Father say when he comes home from his trip and finds me like this?”
“Nothing, dear,” she replied. “He already knows all about my plans for you—and more. Now, go get dressed…you’ll be late for school.”

Oh, god—school! Alan thought. How will I explain all this?