Re: your first time
I was house-sitting for a week during the summer between my junior-senior year in high school. The family had a daughter who was in college, so her bedroom was just as she had left it from high school.
I knew nothing about a fetish, but I knew I was very attracted to the girls in high school who wore Tretorns, Keds, and some styles of Nike and Reebok. In the late 80s, when leggings hit the market, it was irresistable not to be attracted to a girl wearing leggings and Keds or Tretorns.
After a day or two of watching their parents extensive movie collection and making sure the dog was walked and fed, I ventured into the college girl's room. The drawers were empty, save a pair of socks, t-shirts, or panties. Going into the closet, I saw several pairs of shoes, and then an old pair of Keds in the back. They were Champion-style, with the yellow "Comfort Arch insole" and cute blue labels.
I remember smelling her Keds and getting extremely turned on. I undid the laces, and peering inside, I saw her small toeprints in the Keds. I didn't know what to do, but I walked over to her bed and laid down, pulling down my pants and underwear. I remember rubbing the soft canvas along my hard cock, moaning in pleasure. Somehow, I decided to stick my cock inside her Ked, and slide the canvas sneaker back and forth. It wasn't long before I began to build to orgasm; I remember telling myself not to come in her Ked, but passion overtook me, and I humped the Ked harder. When I came in her Ked, it felt so good. After lying there for what seemed like several minutes I pulled out and surveyed the damage. The sneaker was pretty fairly ruined.
I remember trying to dab at the staining canvas, but eventually giving up. I stuck them back where I found them. Interestingly enough, I did see her wear those Keds, and wondered what she noticed, if anything at all. From that point on, I became fascinated with the cute Keds sneaker, and the rest is history.