I don't know why I like it. The interest in wearing female underwear was there since my puberty.
I may not know from where this interest comes but I know what makes it special for me: Feeling it on my skin, knowing this is uncommon for a male to do and showing myself to a woman. It has something humiliating, thinking about what she might think about me, maybe she smirks (hopefully) about it. She could also show it to her female friends.

Humiliation itself, why does someone enjoy being humiliated? I really don't know, it's strange but we all want to do what we like and if it's being humiliated with special things then do it! I do it.

I would wear female clothes on my own but being forced to makes it A LOT better. Forced feminization is great for me and I also love chastity. So that's the perfect combination: Forced feminization through chastity.