How do you confess to your mother you enjoy wearing female garments?

If you know that your mother will be unable to come to terms with you wearing girls' things and you attend school ask the chaplain or person who helps you mentally and say you are asking for a friend who is too afraid to ask. Most of these people will realise that you're asking for yourself however will try to make it look like they believe that it is you friend who you are asking for. They can help and provide an outlet to tell them.

When confessing, make sure you ask her when alone and say it's a private matter. Ask her to understand and tell her that there is nothing wrong with you just because you wear them, also be sure to tell her that it doesn't mean that you are uncomfortable being a guy and that you need a check up and maybe even tell her that aload of people do it. She should understand and may even encourage you to do it. Soon after ask if you can purchase some girls' clothes.

Also ask her to keep it secret from your father or male guardian, he may understand however make you fell embarrassed.

However if you feel you can stop wearing girls' stuff, then do so and do not tell, telling someone about something that you've given up is very annoying and may get you a lot of criticism.