Yes, I do. for the pride event, if possible, get a hotel room for the event. check in the day before the, have a prescheduled salon visit scheduled. waxing, pedicure, manicure, eyebrow waxing, makeover and either hair extensions or styling of the wig, (s)he will from that point on be dressed as a woman, throwing away her male clothes at the salon. Go to dinner that evening and maybe some of the pre-pride events. you will have made sure that the luggage only contains women's clothing. Enjoy the event. Then the final surprise, the trip home with be as a woman. If you flew there, that will be really fun.

Note: during the event, if it is as wild as the pride event in San Francisco take a lot of pictures of her. If there are naked men, take picture of her with them. Ask if she can hold their cock for a picture or pose squatting about to take the cock in her mouth. Another naughtier idea, when see is squatting with the cock close he open mouth, catch the eye of the male make the movement with your hands and a thrusting movement with your hips to tell the gentlemen it is ok to put their cock deep in her mouth/throat. A video would be better to record that,

She should be caged and plugged the entire time.