More from Kitty

• 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 →

  Featured on Kinky Pinup – Kitty

• Masturbating Turns into Filthy Ass Play

  April 29, 2026

  Masturbating with Kitty: When Solo Pleasure Turns into Filthy Ass Play

  Masturbating is my favorite way to unwind after a long day—legs spread wide, fingers circling my swollen clit while I moan softly into my pillow. I thought I had the apartment to myself when I slipped out of my tiny pink thong and started touching myself on the living room couch. My pussy was already soaked, two fingers pumping in and out while my other hand pinched my nipples. I was so lost in pleasure I didn’t hear the front door open.

  Suddenly my roommate’s brother stood in the doorway, eyes locked on my dripping fingers. Instead of running, he smirked. The heat in his stare made me even wetter. “Don’t stop on my account, Kitty,” he said, voice low. I bit my lip, slowly pulling my fingers out and spreading my legs wider so he could see everything. That’s when things got deliciously dirty.

  He dropped to his knees in front of me and buried his face between my thighs, licking my pussy like a starving man. But he didn’t stay there long. His tongue traveled lower, teasing my tight little asshole with slow, wet circles. I gasped as he pushed his tongue inside me—real, deep ass play that made my toes curl. “Fuck, your ass tastes so good,” he growled, spreading my cheeks wider so he could tongue-fuck me properly. I was moaning like a whore, grinding back against his face while my pussy dripped onto the couch.

  

  I reached down and pulled his hair, pushing him deeper. “Eat my ass like you mean it,” I demanded. He obeyed, licking and sucking my tight hole while sliding two fingers into my soaked pussy. The combination had me shaking, my first orgasm crashing over me so hard I squirted all over his chin. But he wasn’t done. He stood up, cock rock hard and throbbing, and rubbed the thick head against my spit-slick asshole.

  “You want it?” he teased. I nodded frantically. “Then beg for it.” I did—whimpering and moaning like the needy slut I become when I’m this turned on. He pushed inside me slowly at first, stretching my ass open around his thick cock. The burn felt incredible. Soon he was fucking me hard, balls slapping against my wet pussy while I rubbed my clit. Every thrust sent waves of filthy pleasure through me. “Harder,” I begged. “Fuck my ass deeper!”

  He pounded me relentlessly, gripping my hips so tight I knew I’d have bruises. The sound of skin slapping skin filled the room along with my loud moans. I came again with his cock buried balls-deep in my ass, my whole body shaking. He pulled out at the last second and painted my ass cheeks and lower back with thick ropes of hot cum, groaning my name as he marked me.

  We collapsed together, breathing hard, my body still tingling. What started as a simple session of masturbating turned into one of the hottest, dirtiest ass play encounters I’ve ever had. I already can’t wait for the next time he “accidentally” walks in on me.

  During my late-night phone sex calls I always share stories like this—telling callers exactly how it feels to have a hungry tongue and a thick cock claiming every hole. Nothing turns them on faster than hearing me describe getting caught masturbating and ending up with a well-fucked ass.

  Want more filthy adventures with me? Meet Kitty