I started wearing ladies underwear when I was 15, at first it was typical teenage horniness, and girls at school always wearing skimpy thongs I could see over their trousers all the time, so I would "borrow" my sisters underwear and j*** off with them imagining they were the girls from school. Then came curiousity. "how could these be comfortable?". So I tried them on, and the fabrics were so nice against my body, but it wasn't until I had them on for longer periods (in secret obviously) that I noticed the uncomfortable "wedgie" feeling disappeared. I then began to wear them when I jerked off, til I felt profoundly guilty that these weren't mine, and "normal guys" don't do this. It wasn't until I hit 19/20 when I confessed this to my then girlfriend, who after having a good giggle about it, asked me if I wanted to try again as she didn't find it that weird compared to some things people like. So, sure, I wore a pair of hers, and things progressed til she had given me 10-15 pairs to try on, get the feel of the styles and fabrics, and see what I like. Nearly 10 years later, I have my own place (she and I broke up a year later from that event, not because of the knickers) and have a secret drawer filled with my own knickers, AND I have a drawer for complete sets of lingerie too. A few of my friends know, and a few female are so comfortable with it that we've been out shopping together, and if I bend over and accidently flash I get a little *ping* of the waistband and a laugh from them. I love my friends to bits, I am so comfortable with it now because of them (and my ex, who is still a friend) that I wear them around the house daily now, not quite ready to take the next step and wear them to work. My advice to guys who want to try, don't wear your sisters without permission (cant hurt to ask, but I get the fear), and if you have friends you can trust then talk to them! Female friends have the best advice as they learn everything from a young age. Pick who you tell though, as the wrong person doesn't always keep secrets as I learnt with one person who is no longer in my life. Life is one big experiment, Live a little.