Boy Becomes Waitress – Transgender Transformation and Crossdressing Romance

“The job’s yours—just be on time, wear the uniform, and smile pretty… Helena.”

Close your eyes, give me your hand, darling.

It was supposed to be a temporary gig. One broken factory machine, one exhausted diner owner, and one mix-up I didn’t correct.

Suddenly, I wasn’t Harold anymore—I was Helena Frost.

The tips were good. The uniform felt… weirdly right. And Boris Stanley—the mysterious regular with the quiet voice and too-intense stare—kept sitting in my section. Kept calling me Helena like he meant it.

Then I found the file. Then I found out I was a test subject.

Now I’m more woman than waitress, and I don’t know whether to sue him… or kiss him again.

Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
Note: This story contains transgender romance, rapid feminization, enemies to lovers, romantic comedy, crossdressing romance, and first time with a transgender woman 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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Published on May 01, 2025 20:48
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