In my teenage years I only had access to my mother's clothing. Size was a limitation. It wasn't until my thirties I felt comfortable purchasing my owns bras, panties and slips. Finally it was dresses and hosiery and heels. Of course a wig came next. The wigs were purchased under the pretext of Halloween costumes. I have to wear a wig to make the illusion work due to male pattern baldness. Underdressing does nothing for me. So, it is always a dress, heels and hosiery, all the proper undergarments, and, wig. I do forego makeup as I am an in-home dresser. The only skimping on the clothes is sleeping at night. Then , it is a nylon gown and panty. I frankly do not understand the appeal of wearing a bra under male clothing.
