1. It is key to force your boyfriend to bet or dare himself into being your girly. NOTHING is worse for a man then being willingly transformed into being a girl. This site is scatterbrained but here are my best ideas!
2. The main point of this site is to give you ideas on how to make this humiliation effective. THE MORE YOU CAN GET HIM TO DRESS LIKE A GIRL THE MORE HE WILL BE YOURS! The best humiliation is when he is NOT in the mood.
3. As for shoes, I recommend high heels---higher the better with fishnets. Boots can also be good. Remember that the humilation is both that he has to wear them AND the fact that he'll learn to walk in them. Make him practice stutting.
4. Men like sluts. So make him be his dream. Short skirts, skimpy underwear, bras, halter tops--whatever you think looks trashy he needs to wear. Having him spend money on the clothes and picking it out can be key to his humilation. Imagine his humilation if you bought HIM a dress for his birthday?
5. Makeup is key--part of the fear in a forced humilation is that he can't get out of the clothes and makeup if the fire alarm goes off. Heavy make up then is key. Foundation, mascara, eyeliner, blush, lipstick--cake it on your humilation target. The best thing about glue on nails and nail polish is that they are hard to get off--PERFECT for scaring him. In my experience, glue on eyelashes, even if not that long, can be terrifying for guys scared of glue. So I would say that they would be GREAT in any humiliation. I like french manicure nails, but anything girly should be good. PERFUME, often overlooked, is a nice addition too. Make him smell like a prostitute if you are going to make him look like one!
6. Hair is tough---I think long wigs are the best, particularly if he has hair to cover. While trying to make a male haircut girly is tough it can be done. God it would be fun to take him to a salon :). Dyeing hair can be fun too.
7. Shaving--a big step but a must if you want to have those feminine legs. He certainly can get by in the winter--most hair grows back in a week. Remember the goal is humiliation so don't forget his underarms.
9. Jewelry--tiny additions can be huge in these humiliations. Earings, necklaces, rings, anklets all add the girl touch so pile them on---remember matching doesn't matter. In a humiliation, the more tiny steps the more it adds up. And it is funny to watch him jingle around with so many braclets on.
10. TIME: The longer you can keep him dressed the bettter. A quick dare is something, but multiplied the longer it goes. Make him learn how to be a girl and make him do it often. Even a schedule that every second Tues is "Girl's Night" can be a great way to keep him home and docile.
11. CHEST: Men like women with chests, so give him a big one. It doesn't matter if it looks real, but the key is humiliation. Watch him try to sleep with DDs.
12. SPEECH: The voice needs to fit. Make him practice talking like a girl. Going even farther, you can make him practice picking up "men". And don't forget to call him gay if you think that will add to the humiliation (if you can get a guy to do all this he is probably straight).
8. Name and treatment-- treat your humiliated boyfriend like what he is dressed like--a cheap floozy. Give him a girly name and call him that. Order him around. It is particular good if you can get him aroused when dressed--take pictures too. Even if you let him keep the pics, the fact they exist adds to his humilation. Watching a man play with himself with long false nails is positively funny and should be documented in photos.
13. Make him dress up even if you are not there or before you get there. Then he is a participant in it.
14. Good luck and have fun! Email me if you these were belpful. Eventually I will put up more humilation ideas.