Has he exhibited sufficiently feminine values and attitudes? Are there any complaints about his attitude? Does he have a quick smile and a ready ‘Yes Ma’am (or Sir)!’ for every request? If so, maybe he deserves a promotion—as your personal assistant. Be specific about the many ‘personal’ services you’ll expect him to perform for you.
Tip: You must ritualize your dominance over the one-time executive cum office pet on a daily basis. Institute a ‘Desk Time’ for your pretty assistant, perhaps in the morning. Have him prepare himself—and you—appropriately, then use him the way he once used the pretty secretaries himself—legs spread and bent over a desk.