The first time I actually bought and tried on lingerie was a defining moment for me. By this time in my life, I had bought lots of things of things in stores either pretending they were a gift or adding them to other things like at a discount store.
I had hovered around the local Frederick's of Hollywood store many times. Just looking inside was a thrill. I had even gone inside browsing, but I didn't buy anything. A couple times, I had called the store and just asked the girl if they would have a problem with a guy trying on things there. She told me, no, it would be OK. Finally, I had to do it.
I was wearing a pair of pantyhose under my pants with no socks, something that at the time was pretty daring for me. I walked in and asked about a particular garter-girdle I was interested in. Back then, they still carried some girdles in the store. I must have been shaking when she showed it to me. Then came the moment of truth. I hemmed and hawed about it. And I finally asked her if I could try it on.
"Certainly," she said. She walked back to one of the back fitting rooms. OMG!! I was actually being led to the ladies fitting room to try on lingerie!! She placed it folded on a stool and said if there was anything I needed to let her know. I walked in and closed the door. This is it, I thought! I'm in the inner sanctum! I removed shoes and pants and started to put on the girdle. What fun!
The other clerk walked by, and she must have seen my stocking-clad feet. I could hear her quietly tell the other clerk with a chuckle, "He's wearing pantyhose." There was a bit of humiliation in that I really liked. I was admiring myself in the mirror for awhile when my clerk asked through the door if everything was fitting OK. I replied that it was fine. I realized that I didn't want to overstay my welcome, so I took off the girdle and got dressed.
I felt like I was walking on air when I walked out of the fitting room carring the lingerie I had just tried on. There were no other customers in the store. The clerk asked if I wanted to take that, and I said yes. Then I asked her if she would have a fully padded bra in a 36C. She took me over to the plastic drawers and looked for a bra in my size.
She displayed the fancy brassiere to me. It was quite delightful. I had never seen one quite that nice before. I asked to try it on as well and I was off again to return to my fitting room. This time, I removed my shirt and put on my bra and admired it in the mirror. I'd never had such a fully padded bra before and it was just wonderful!
I was giddy when I came out. "I like it a lot!" The clerk rang up my purchases, and I left the store with my Frederick's bag. Now I was a bit concerned of being seen by someone I knew. But somehow, I wanted the world to know I had just tried on a bra and girdle in the store! What a thrilling experience this had been!!