Five Days to Sissy

WEDNESDAY

So, it turned out school wasn’t nearly as bad as Alan imagined. Since his stepmother had advised the administration, he was transferred to a special section for sissies and other feminized boys. There were ten other students in the group, in various stages of transition. A few were nearly impossible to distinguish from true females and one was wearing just lipstick to acknowledge his emasculated status.

Still, Alan was alarmed when he awoke to find yet another step would be taken on Wednesday. In addition to a pair of lacy pink panties, a matching bra lay upon his dresser. “Bring this to the dressing room” said the accompanying note. Knowing by now that there was no use in resisting, he pulled on the panties, picked up the bra and followed instructions. Violet was waiting for him at the vanity. “That’s a good sissy,” she said, smiling. “Now, sit while I fix your face and then we’ll try on your bra.” Within minutes, she was done. “Stand up, dear.”

Alan obeyed and the maid wrapped the delicate pink device around his chest, hooking it in the back. She reached into a drawer of the vanity and produced a pair of false tits. Alan gasped, “Please, Violet, hasn’t this gone far enough?”

“Your stepmother has directed this, and it will be done,” she replied, as she slipped the two pieces of foam into pockets in the cups of the bra. She made sure they were arranged properly and stepped back. “Hmm, I’d say 32-B, just the right size and shape for a sissy your age. As you grow older, we may make them a bit bigger! Now, your school clothes…..” She handed Alan a tight-fitting t-shirt that clung to his bust, outlining the shape, and making the bra straps and back quite obvious. His trousers were a pair of stretch jeans with hems above his ankles, so that the sheer nylon socks he wore were evident. “Go to Ma’am’s room and let her see what a prissy little thing we have made you into.”

The tight jeans restricted Alan’s stride to a ladylike mince as he went to his stepmother’s boudoir. As usual, she was sitting in bed in her revealing negligee and she smiled as Alan entered. “How delightful you look, darling,” she cried. “Come closer.” Alan approached her bed. She reached out and gently stroked his faux breasts and then let her hand stray to the bulge at his crotch, feeling it twitch as she ran her hand over it. “Yes, all the expected reactions!”

She summoned Violet. “Master Alan is ready for school….and we have preparations to make for tomorrow!”