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.
dress me dress me
I am me. A monk.
Take him to the salon and get his hair and nails done. Take him to Macy's perfume counter. Take him to hear scottish bsgpipers and learn scottish dancing and encourage him to wear a kilt. Have him try some of the new man skirts.. Watch the movie Kinky Boots with him or see it on B'way. Get him a little soused and lead him to a womens beauty spa. Once he begins to get used to this then move on to womens underwear being sexy for a man to wear. Throw out his swimsuits and give him only speedos. Finally it is time to visit the big and tall womens boutique.
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.