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Going Fem: What would someone need to do for their first time?

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Hello, I was hoping to get some information from anyone who has experience with cross dressing. I have a male character who is being done up as a woman to go to a bar. They are a typical male CIS character.

If a CIS man were to cross dress as a pretty woman, what would the first time process look like? The character has access to a drag queen who is running the makeover, so the character themselves doesn't need the technical knowledge.

Is this for a story? If so I'd need to know more about the story. You can private message me if you don't want to share that here.