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Chapter 2
by
smalldickryder
Which Letter does she answer first?
Can InTell her something small
Dear Mistress Kylie,
I’m Richard, 54, recently divorced and now dating a wonderful 48-year-old woman named Lisa. She’s sexy, confident, with full breasts and a wicked smile that makes my cock twitch, or at least it tries.
Here’s the problem: I have a massive small penis humiliation kink that I’ve hidden my whole life. My dick is only about 4 inches hard, thin, and it leaks pre-cum at the slightest tease. I get rock hard when I fantasize about a woman laughing at it, comparing it to real cocks, making me watch her get fucked by bigger men while she mocks my pathetic little clitty.
With Lisa, I want to tell her so badly. I imagine her discovering it, giggling as she holds it between two fingers, calling it cute but useless. I’d drop to my knees, licking her superior pussy while she describes how a real man would stretch her. The thought of her in lingerie, pointing and laughing as I edge my tiny prick without cumming makes me throb with shame and lust. But I’m terrified she’ll leave me. I’ve jerked off for years to SPH captions and videos, imagining my girlfriend’s friends knowing my secret, teasing me relentlessly.
Mistress, how do I confess this without scaring her away? I want her to own me, lock me in a tiny cage, make me her humiliated beta while she enjoys bigger cocks. The embarrassment turns me on more than anything. Help me explore this kink safely and erotically with my new girlfriend.
Secretly,
Dick
What's next?
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Dear Mistress Kylie
Letters to better understand the world
Mistress Kylie is here to answer your question. Submit a question in the inbox and Mistress Kylie will tackle your problem head on like your domme! Or at least train you to be the domme or sub in your sex life!
Updated on May 22, 2026
by smalldickryder
Created on May 19, 2026
by smalldickryder
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