Diary Entry: Sissy Makeup Musings

What is happening to me?

After chatting with Mistress Lillith and prior to bed, I put on a pair of panties, played my sissy mantras on my headphones, and began watching the makeup tutorial videos she had referenced in her email assignment.

My smooth hairless skin, the panties gripping tight, training mantras on repeat softly pounding into my head, suddenly a cute girl discussing how to put on makeup–but nothing sexual-focused, no erotic suggestions. Just makeup. And damn I was turned on. Makeup has never been a thing for me. Not even close to getting aroused by it. I mean, I’m not one of those “beardo sissies”, but it was always more of a slight curiosity if anything.

Last night it became eroticized. 

The thought of painting my face, along with the rest of the changes taking place… staring into a mirror and looking myself literally in the eye as I made changes.

Sending pictures before, during, and after… of my face. Would I be humiliated to a large lump in my throat with the makeup? Or would I smile? I think I’d smile, but there’s a (small) chance otherwise…

Sometimes it’s hard to step outside of oneself and have awareness of what’s happening. The mirror and pictures would help bring the changes more closely into focus. This would be harder to compartmentalize. This would be pretty gay by almost any standard.

I reached out to Mistress Lillith and asked, begged almost, to train me as a sissy and teach me to serve as a submissive. “Not fantasy,” I said, “I’m looking for more of a real Mistress experience.”

Now on week 3 we are approaching areas I haven’t really explored before (well, maybe a little here and there 🙂 . This isn’t a limit being approached, more like a fertile untapped area for exploration. It’s exciting. And scary. Fear can be hot.

I’m not sure what is turning me on. (Mistress Lillith will probably roll her eyes at that statement!!) I don’t think it’s the makeup, but I’m not sure anymore. I think it’s the power exchange, but that doesn’t necessitate the sissy fetish. So there must be more.

I feel like a shy blank slate. I’m glad an experienced pro domme like Mistress Lillith is there to guide me through this experience!!


Breaking my sissies and submissives down to the point that they know longer know WHO they are is something I enjoy. Because then they ARE like a blank slate. Only those that wish to truly be broken down will though, this sissy of mine I have become very fond of, very quickly. Untapped potential and areas of exploration are a delicacy in the sissy trainer world. Sissy Exploration is desired by the sissy in training and the experienced sissy trainer – limits sometimes shift and get broken down – and what blooms from that?

Only time will tell.

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