2/5 - (1 vote) Unless your mother dresses you up in girls clothing at age 3, I would assume about age 11 or 12 years old for most boys . I was probably an exception. I wore my first pair of panties at age 5. I was staying at my grandmother’s for the summer. One day, she left to go to a neighbor’s house to borrow some flower and chat for a few minutes. At this time I saw my chance to go into her room and look in her undies drawer. Since I’d been think about wearing girls undies...
