Well, it's true he has to do some reaching out, I don't want to discourage him. What he is asking for doesn't seen unreasonable to me. The roll play may be a bit of an issue, but the rest is simple outfit requests. Technically speaking, all companions are doing a role play to some extent.
Personally, I would start with the Fetish ad section of the site which currently has one advertiser, but a couple others also list "Domme" (just another type of fetish) as an option. That's 3 names I could drop right now as potentials. Not that you want a Domme session, but part of that type of service is a role play.
As long as you ask a lady politely, respectfully and with details of what you are looking for, she will give an honest answer. Although, it's easier to get a yes if she already knows you, is comfortable with you, and sees you as a good client. Offering a nice tip also helps grease the wheels to get you where you want to go.
Also mentioning you are a member here helps a bit as it shows you to be more serious than some lurker who chickens out at the last minute.