More from Kitty

• Forced Sissy Training with Kitty & Juliette

  August 25, 2026

  Forced Sissy

  The night Juliette and I broke him completely

  Forced sissy is the sweetest sound in the world when it comes from a man who still thinks he has a choice. Juliette and I had him on his knees between us, already dressed in the pink panties and tiny skirt we’d chosen. He kept insisting he wasn’t really a sissy. We just smiled and kept going. I held his chin while Juliette locked the chastity cage on tighter. Every time he squirmed I made him thank us for the privilege of being locked.

  We spent the next hour layering pure humiliation on him. I made him kiss Juliette’s boots while she filmed. Then she made him kiss mine. We took turns telling him exactly how pathetic he looked, how small he was, how lucky he was that two women were even wasting time on him. He tried to stay quiet at first. That didn’t last. By the time we had lipstick smeared across his face and a plug seated deep inside him, he was already whispering “yes Mistress” without being told.

  Juliette and I took turns using his mouth while the other sat back and laughed. We made him clean us both, then ordered him to describe how much he loved being our forced sissy. The more he resisted, the harder we pushed the humiliation. By the end he was crying, hard in that little cage, and begging us not to stop. That is when the real training begins — when the fight leaves and only the need to please remains.

  Some nights we keep him on the phone afterward and walk him through every second of it again. Phone sex lets us keep the humiliation fresh even when we’re not in the same room. We take turns describing how he looked, how he sounded, how completely we owned him. He stays locked and aching until we decide he’s suffered enough. Most nights that takes a very long time.

  ---

  If you think you can handle being trained by both of us, you already know where to find us. Come ready to lose everything that still feels like manhood.

  — Kitty

  Visit Kitty →  |  Visit Juliette →

• Sissy Training with Kitty

  June 7, 2026

  Sissy Training with Kitty: Humiliating His Tiny Penis on Our First Call

  Oh darling, let me tell you about my latest sissy training session that had me smiling the whole night. I adore welcoming a brand new sissy and diving straight into delicious small penis humiliation during our intimate phone sex call.

  He rang me up through my Kinky Pinup page, sounding so nervous and eager. Right away I cooed, “Tell Kitty about that tiny little clitty of yours,” and the sissy training began in earnest. I made him describe every inadequate inch while I giggled sweetly, turning his shame into the most addictive fuel for our steamy session.

  “Aww, is that really all there is, sissy? That pathetic tiny penis doesn’t even qualify as a cock. It’s just a cute little button for me to tease and laugh at during your sissy training.”

  He whimpered so prettily as I walked him through his first proper sissy tasks. On his knees, panties around his ankles, stroking that worthless little nub while I painted vivid pictures of his future in frilly lingerie and a sparkly pink cage. The small penis humiliation flowed naturally — telling him how real men would smirk, how he’d never please a woman, and how perfect he’d look all dolled up for me. Phone sex with Kitty always becomes full sissy transformation, and this new boy was completely hooked.

  By the end he was begging for more sissy training, promising to shop for the sluttiest outfits just to earn my approval. I love breaking in fresh sissies like this, wrapping their tiny penis humiliation in soft, sensual dominance until they crave it.

  Hiding a pathetic little secret of your own? Call me for personalized sissy training and the most teasing phone sex experience. I’ll turn your small penis humiliation into pure, blushing pleasure, one humiliating inch at a time.

  Call Kitty for Sissy Training Now →

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