The Girly Tutor: First-time Feminization Romance

Lilly Lustwood


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“I’m not going to study if you’re not going to play dress-up!”
This is an illustrated romance novella, complete with beautiful images inside. Enjoy!

Two years ago, I was a tech darling—overpaid, overconfident, and living rent-free in Manhattan. Then my startup collapsed overnight, my salary became a curse, and I found myself one paycheck away from disappearing.

That’s when I took a job I didn’t understand.

Live-in tutor. Penthouse near Central Park. One widowed billionaire. One grieving nine-year-old girl who refused to study—and instead wanted to play dress-up. I told myself it was temporary. The makeup. The dresses. The name she gave me.

Glinda.

But grief has a way of uncovering truths you’ve buried your whole life. As I helped Allie heal, I started unraveling too—falling into a softness that felt less like pretending and more like remembering. And somewhere between fairy wings and quiet dinners, I fell in love with Peyton Sinclair… a man who saw me clearly and never asked me to be smaller.

The problem? I wasn’t just crossing lines. I was crossing into myself.

Note: This story contains transgender romance, transgender transformation, gradual feminization, friends-to-lovers, coming-of-age, and first-time feminization tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
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