The first time I bought an item(s) of woman's clothing was back in January of last year. I'd only just received my debit card and was eagerly online shopping! I remember being so scared my parent would find out I chose a specific time and date for the delivery when I knew he was guaranteed to be away, ended up costing quite a bit more, haha.
I guess it's kind of scary at first because it's like a step in to the unknown, even if you've worn some before, actually owning clothing from the opposite sex is a new feeling.
Good for you, anyway 🙂