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Ask him what he’s into, for starters? Particularly hobbies.
You’d be spoiled for choice if he’s into the typical reddit fair of gaming, anime and scifi/fantasy. Uniforms, costumes and specialty clothing are always a winner and assist a great deal in getting into the flow of things.
Imagine an existing dynamic and where you’d each fit as the characters, and taking into account how open minded you each are.
Teacher/student? Put together a school uniform-style outfit and tell him to dress more business like, as though he was a teacher. Think of a scenario like you being “kept after class” for some private tutoring.
Secretary/Manager? Break out a tight fitting blouse, pencil skirt and some stockings and heels.
If he likes something more fantastical, then Elves (not the christmas kind) and Catgirls are sure winners. You can easily buy a few items at a costume shop like ears, skirts, fairy wings etc. Catgirls give you the chance to flex your makeup skills too and put together an alluring cat-like look.
The best thing to do would be to surprise him with the outfit and encourage him to play along. Find a time you can get changed in secret and surprise him with a bit of roleplay dialogue when you show up that invites him to you.
Good luck!