Pretty as a Princess 2: TRANSGENDER, First-Time, Crossdressing

An Illustrated Transgender-Themed Novel of Feminine Discovery.

Ray didn’t mean to become the girl everyone saw—he only wanted to be liked. To be neat. To be seen the way Bonnie saw him.

But once again, a little curl becomes a wave. A simple compliment becomes a dress. And a mother’s pride becomes something harder to say no to.

In this emotionally rich, gorgeously illustrated sequel to Pretty as a Princess, Ray finds himself caught between the comforting routines of femininity and the ache of not knowing where he truly belongs. What begins as a quiet summer of playdates and hair setting slowly evolves into something deeper—a story of soft rituals, blurred lines, and the delicate power of being chosen.

When Bonnie and her friends crown him their “honorary girl,” Ray is startled by how right it feels. Jump rope, kittens, dress-up games—he’s part of something. Wanted. But that comfort comes with new demands. A boy must become something... prettier.

At first, Ray struggles. A botched hair tutorial. A teasing cousin. A green dress he’s unsure he wants—but can’t stop touching. And when strangers begin mistaking him for a girl in public, the world outside feels less forgiving. Boys laugh. Cashiers misname him. And still, his mother, June, insists on polish. On rules. On curlers, panties, and the right kind of softness.

As the pressure mounts, June plans something a salon perm. Ray resists, but a compromise is struck—Bonnie’s mother will do it in private. Before the appointment, Bonnie invites Ray to a girls-only tea party, and he prepares like a princess in setting lotion, rollers, bobby pins, and trembling hands.

He wants to belong. He wants to resist. He wants to look beautiful... but not always. Not only.

Featuring 9 exquisitely rendered illustrations, Pretty as a Princess 2 invites readers back into Ray’s delicate world—where motherly expectations blur into subtle dominance, where friendship offers both comfort and complication, and where one boy’s slow, sweet unraveling continues to unfold.

Perfect for fans of feminization fiction, and crossdressing stories, this novel delivers page after page of sensory detail, emotional vulnerability, and quiet surrender. If you ever longed to be told how to dress, how to sit, how to feel, this book was written for you.

Ray didn’t choose to be their princess. But when the ribbons are tied, and the curls set in place... maybe he doesn’t want to untie them either.