How do you get a boy to dress like a girl?

give him money (i would do it ) Get him to wear your panties. starting small with panties though is a good idea try silk or satin as they feel good on a boy's private region. then adding more clothes slowly may get what you want but that all depends on the boy if he likes you simply tell him that a boy dressing like a girl is something that you like some boys will never do it but by bringing up the subject frequently you may eventually talk him into doing it but do not push it on him if it is not his thing you may lose him. outta 10 men crossdress in a way, wether it's hidden, just a pair of panties, or full blown, with wigs, makeup, and breastforms like I do. it's just a matter of figuring it out. It's actually very healthy, and a great turn in role playing in the bedroom. Just bring it up, like 'it would be so hot if we traded underwear for a day cause you'd be thinking of me all day'. It's simple Get a bunch of girls to be secretly invited to your house and force the clothes. One day with the help of my friends, we forced my 13 year old brother to dress like a girl cheerleader. He had on the spankies and a blue sleeveless top with a sports bra underneath. He also had to wear a short blue Cheerleading skirt, with cheerleading shoes on. We even gave him pom poms and made him do some cheers.