Sissy Training with Kitty: Your Sweet Pinup Guide to Becoming Pretty
Kitty has always loved helping shy boys discover their softer side. There’s something so sweet about watching a nervous little thing blush when she first calls him “princess.” Sissy training with Kitty isn’t harsh or scary—it’s gentle, glamorous, and oh-so-irresistible.
She starts every session with you sitting at her pretty vanity table, surrounded by lipsticks, powders, and perfume bottles that smell like vanilla and roses. “Relax, sweetie,” she whispers, brushing your hair back with soft fingers. “We’re just going to make you look as beautiful as you feel inside.”
First comes the foundation—smooth and flawless, just like her own perfect skin. Then rosy blush on your cheeks, long fluttery lashes, and glossy pink lipstick that makes your mouth look kissable. Kitty steps back, tilts your chin, and smiles. “Look at my pretty girl already. Doesn’t that feel nice?”
Next she helps you into silky stockings, rolling them slowly up your legs while telling you how lovely they look. A lacy garter belt, a satin bra with just a touch of padding, and finally a fluttery babydoll nightie in soft peach or baby pink. Every piece makes you feel smaller, softer, more delicate.
“Walk for me, princess,” she says sweetly. “Small steps, hips swaying, hands soft.” When you stumble she catches you, steadies you, and praises every tiny improvement. “Good girl. You’re learning so fast.”
She teaches you to curtsey, to say “Yes, Miss Kitty” in your sweetest voice, to sit with your knees together and your hands folded in your lap. Each lesson ends with a gentle reward—a kiss on the cheek, a stroke through your hair, or letting you kneel at her feet while she tells you how proud she is of her new sissy.
Sissy training with Kitty is never rushed. She wants you to savor every moment of becoming prettier, more obedient, more feminine. By the end of the session you’re blushing, fluttering your lashes, and thanking her in the tiniest, sweetest voice.
“You did so well today, darling,” she murmurs, tucking a strand of hair behind your ear. “Next time we’ll try heels… and maybe some pretty panties you can keep.”
Ready to begin your sissy journey with the sweetest pinup trainer?