As young boys, my jack-off buddy and I discovered his sister's lingerie drawer!
When I was twelve and my buddy was thirteen, we discovered his sister's underwear. We had been jacking off together for about a year, he taught me how. When I'd sleep over at his house, we'd lie in bed and try different ways to pleasure ourselves, and compare notes, and tell each other about how we had jacked off when we were alone.
He had just got little hairs around his penis, I was still hairless. He would cum a little bit, and I had just started to have drops of cum appear when I climaxed. When we were alone in the house we would get naked and jack in front of each other, or go around the house with our boners stroking ourselves excitedly.
One day we were alone in the house, and naked, and we went into his sister's room, and he told me he'd worn her underclothes. I got very excited and wanted to try, and so we plunged into her drawer. I was shaking with excitement! He pulled out some panties, and I wiggled into them. We were both erect and bobbing in the air. He had a pair he liked, and he pulled them up, over his penis. My nipples were hard and excited, and I couldn't sit still. He pulled out a bra from the drawer, a red silky bra, and gave it to me to put on. I had to work to figure it out, but got it on, and ohhhh I felt so good!
I ran over to the mirror and looked, and that made me feel even better! My buddy put one on, too, a black one, and we both pranced and watched each other. He was rubbing his dick inside the panties, and I put my hand there, and the silky feeling was more than I could bare. My little cock began twitching and filling me with pleasure. My friend rubbed himself a little more, and then I watched him cum (his mouth always fell open) and a wet spot appeared on the panties.
After that, he kept a pair in his room, and every time we got together to jack, he would let me wear them to jack off in. I got to like the feeling so much of my dick sliding in the silky panties. If his sister was out, we'd go and get new clothes and bras and play in them, those were always our most exciting jack-off sessions!!