Hmm... Perhaps it could possibly be worked into the Rich Boy x Servant scenario? It wouldn't have to be the basis of the roleplay like it was in the Crossdresser x Classmate one, but perhaps the servant could be coerced into dressing up like that at some point? I suppose the role is also more familiar to me; a bit snobbish, haughty, and controlling. This set up was my second choice anyway, as I see a lot of potential for humorous conflict. About what age did you have in mind for those boys?