Tuesday, April 30, 2024

Five Days to Sissy


The next morning, Alan woke up to find another pair of panties on his dresser, and another note: “Put these on and them come to Ma’am’s dressing room.” The new scanties were even frillier than Monday’s pair, with a big bow on the front and three rows of ruffles across the back. Shrugging in resignation, Alan pulled them into place and again felt his cock rise in response. He padded down the corridor in bare feet to his stepmother’s dressing room.

On entering, he found Violet standing by the vanity. She motioned to the delicate chair before it and said, “Have a seat,” as she turned the chair so that it faced away from the mirror. Apprehensive, Alan obeyed, wondering what was next in his stepmother’s plans. He looked over the array of jars and bottles and brushes on the vanity. “Yes, Master Alan, those are all for you!” Violet said.

She picked a bottle of liquid foundation. “This is the right shade for your complexion. Now close your eyes while I apply it.” With a small sponge, she wiped his entire face and blended it in carefully. When she was done, she lifted his chin with one hand and turned his face in both directions. “Yes! It’s a good choice.” She brushed his bangs back to observe his eyebrows. “Fortunately, your brows are in good shape—we won’t need to pluck them, for now.”

Violet searched among the cosmetics and found the eyeshadow, in a deep shade of pink. She applied some of the color to a small brush. “Close your eyes and keep them closed until I say to open them,” she directed. Alan felt the feathery touch of the brush on first one eyelid, then the other. It tickled and he struggled to keep them closed as ordered. “Open your eyes,” the maid said. “Very pretty…but we’re not done.” She picked up the eyeliner. “Close them again,” she said, and stroked an even line of black just above his lashes. “Now, open them and look up.” This time she drew a line just above his lower lashes. Looking closely, she nodded.

Next was the mascara. “Open your eyes wide,” she directed. Alan felt the curved brush on his upper lashes, darkening and lengthening them. When Violet finished his eyelids felt heavier. She then moved to lightly coat his lower lashes as well. “How wide and beautiful they make your eyes seem, sweetie!”

The next stage was lipstick. “Open your mouth in an ‘O’,” she said and coated his lips with the sweet pink color. “Now, purse your lips as though you were kissing,” she ordered, and then applied a second coat. “Oh, lovely, pink and wet and so girly!” Violet exclaimed. “Are you finally done?” Alan asked.

“Not quite,” the maid answered. She picked up a wide brush and applied a soft pink to his cheeks. “There! The perfect embarrassed look for a humiliated sissy!” she declared. “Now, go get dressed for school!”
“School?” Alan asked, shocked. “I can’t go to school with my face painted like this!”

“You can and you will,” his stepmother announced from the doorway. “I’ve already cleared it with the administration. It seems you’re not the first sissy they’ve had as a student!”

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