There are many who would volunteer and wear just about anything you could come up with including make up and doing their hair. Try making s bet that you can't lose.
Only a ***** would dress up like a girl, unless he was being extremely silly and trying to make you laugh he might put on your bra over his clothes but panties and dresses and all that ****, nah, don't think a straight guy would do it unless he was what you call a sissy or ***** n into that cuckold lifestyle.
tell him that he would feel much better in girl clothes than guy clothes :). make him wear the most girly dress you have with some small heels to start him out :). and panties because a thong would kind of hurt being small on his 'package'
you cant if he doesnt want to
Tell him how hot & sexy he will be. Then put him in a thong,stuffed bra and hooker dress.
I won a bet with my boyfriend. I made him wear a super short French maid outfit with a hot pink thong, I put a lock on the belt so he couldn't take it off. I made him also wear knee high boots. I made him serve me and all my friends for 6 months. :)
dress me dress me
I am me. A monk.
what's the context? does he want to?
Well, you know best what to have him wear. Do it in such a way that he feels nice and femme, maybe a little bit slutty, and maybe? just a little bit humiliated? Fun and games!! Have fun with it!
Have him wear a short knee length a-line dress or skirt with a net petticoat underneath. Those type dresses make any guy look sweet and feminine. Get a bra with silicone breasts of at least a c cup. have him prance around the house swinging his hips side to side and jumping up and down in place to see his boobs bounce.