From Fanboy to Femboy Part 1: A Femboy is Born by Chastain Tiffany

Author:Chastain, Tiffany
Language: eng
Format: epub
Published: 2024-06-12T23:00:00+00:00

Chapter 5

Dress Up

“Hurry up, this way!” Cassidy’s manager said as she pulled me down the dark hall.

From behind me I could hear Cassidy’s muffled singing and felt a pang of sadness that I wasn’t there to see her acoustic set. I tried to block my sorrow and think about how missing a song or two would be nothing compared to what I was about to do.

“Here,” she said as she came to a stop before a door. “This is Cassidy’s changing room. Inside, Susan will help you get dressed. You have 10 minutes before Cassidy’s next set so just do whatever she says and then I’ll get you back on stage.

I nodded my understanding then she swung open the door and pushed me inside. The door slammed loudly behind me as a tall, slender woman wearing tight blue jeans and a white spaghetti strap blouse sauntered towards me in tall black heels.

“A man?” she let out, with a sound of disgust. “Of course she can’t make this easy.”

She started circling me as I took in my new surroundings. The room was filled with brightly colored clothes hanging on racks and I instantly recognized many of them as outfits Cassidy had worn tonight. I was suddenly dying to reach out and touch them. To smell them.

“I don’t really have much clothes for a man,” Susan continued. “But then again, you don’t really seem to be dressed much like one anyways. I think I may be able to work with you after all.”

I had no idea what she had in mind, but I had a feeling it would definitely push my comfort zone to a new level. I knew that it would be worth it, however. “You can?” I let out anxiously.

“Yes. Are you perchance wearing matching panties with that bra?”

I felt my chest tingle at her words while my cheeks started to burn with embarrassment.

Is my bra that noticeable? How can everyone tell that I’m wearing one?

“Uhh… umm…” I muttered.

“We don’t have time for you to play coy. Just tell me!” Susan interrupted. “Better yet, just strip down to your bra and… whatever undergarments you’re wearing so I can really see what I’m working with.”

My face felt aflame now. I hadn’t considered that I would have to get undressed in front of anyone, especially to show off my bra and panties. I knew I didn’t have a choice, however. Not unless I wanted to disappoint Cassidy.

“O-okay…” I replied sheepishly as I began to pull off my shirt.

Susan quickly snatched the shirt from my hands and threw it into a corner of the room. “Hurry up!” she snapped at me.

I started fumbling with my pants button and then quickly unzipped them and started pulling them off, leaving nothing on but my pink bra, panties, and tights. Standing in that room in front of Susan made me feel exposed in a way I had never felt before. My hands covered my panties so that she couldn’t see them or my scared, shrinking penis.

“Ah, so you are wearing panties.

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