My first times out when I was 17, I was very nervous and chickened out many times before I did it. I figured everyone would notice this guy dressed like a girl. When I finally got the nerve, I got close enough to people where I could be seen but not touched.
No one really seemed to notice. That gave me more nerve and confidence. I began getting closer and closer to people. I walked among them and went into stores looking at the pantyhose, shoes, bras panties and other girly things. it was a huge deal when I bought my first pantyhose.
I was pretty sure I got looks from time to time but no one said anything to me. That all changed when one day while picking out pantyhose, a girl told me I had great legs, asked what pantyhose I was wearing and were they what I was buying. That was my first recognition for sure that I was en femme and wearing pantyhose. I panicked, put down the pantyhose and ran off. I was so freaked, I swore I would never do that again. A few day later i got dressed and went back and rescued the pantyhose I left behind.
I had been disappointed that I was out dressed and no one seemed to notice or make remarks or comments. I got bolder seeing how far I could go before I got a reaction. When I knew, I panicked. It didn’t stop me though. I kept going, getting bolder and doing more adventurous things.
I did get complimented again on having nice legs, nice shoes and did get asked about the pantyhose I was wearing and buying. I was even politely notified on a few occasions about runs in my pantyhose.
I guess the more you push the bold aspects of dressing and going out, the closer you will get to being noticed and be involved in personal encounters.