It was about 1991. I was 13 and staying at my friend Josh's house down the street one summer night. It was one of those sleepovers where we decided to just stay up all night bullshitting about 13 year old kind of stuff.
His parents were cheap and didn't run the air conditioner, and I had worn jeans that night for some reason. I mentioned that I was hot, and instantly he tosses me this silky pair of shorts and says "wear these.' I dropped my pants and started sliding them up, but before I could get them past my ankles Josh said "no, you don't wear underwear with them." So I slid my underwear off, and pulled these tight little shorts up over my cock and little bubble ass. Out of nowhere, my cock sprang to attention, causing a bit of embarrassment on my part. But I couldn't help it, I kept looking down at these shorts; The left leg was the shiniest black I'd ever seen, and on the right leg was this checkered pattern that encompassed the entire leg. I could see every curve of my slender body, my runner's ass looked amazing in them, and it was making me hard beyond belief.
Josh looked over and could see both my raging hard on, and the look of 50/50 confusion and enjoyment. He said "Don't worry, that happens all the time with these. And to my surprise, he pulls out another pair, this one black with red stripes down each leg. As he slides his underwear off, and pulls the shorts up, his long dick starts poking out his left leg instantly. "See, look, I wear these all the time and it still happens".
I still hadn't fully come to terms with what was going on yet, but I knew I wanted to wear these all the time. Josh could see it, and he let me keep the shorts to wear all the time, I which I did, all the way up the summer of my sophmore year. I wore many other pairs that I had convinced my mom to buy too; nikes with the no-seam front, this cray Mervin's generic brand that was hot, MacGregor ones that were also hot. My first pair of official running tights bought in 1997 at the Reebok outlet store--still have them, as you can see from my photos--The list was nearly endless. I was in good company too, we all loved to wear bike shorts with crazy designs on them during that time. It was a fashion statement, and one that got me my first solid crotch grab in my early years.