I never thought I'd have the stones, but damn did it feel good.
For the majority of my life, from about kindergarten well into adulthood, I've had a friend named Steve. Steve had a pool, and he would always invite me over to swim. It was always fun, and we would always mess around in the pool.
One night, just before sophomore year of high school started, Steve invited me over to his house to hang out and swim. I said sure, and I went home and changed. I grabbed a bathing suit and headed right over.
We swam for most of the day, until it eventually got dark. At that point, his sister Annie came out of the house. She was home before she went out for her first year of college. She was nothing special, a bit on the chubby side but with a cute face, brown hair and green eyes. I always thought she was cute, but I had never thought of her in a sexual way, perhaps except for a puppy love crush in the second grade.
She was wearing a black bikini, and she slipped right into the pool. Right away, I noticed her tits nearly hanging out of her top. I'd say they were 32D, and they were full. They were glistening wet from the water, and I couldn't take my eyes off of them. I even got hard in my bathing suit. Later, she got out of the pool to do a cannonball, and her bottoms rode up to show camel toe. My dick was rock hard at that point.
When we all got out of the pool, we all dried off on the back deck. When we went inside, I said that I had left my keys in Steve's room. They said they'd wait for me in the dining room. I ran upstairs straight to his sister's room, and made for the dresser. The first drawer was shirts and makeup, but the second was a jackpot; panties and bras. I grabbed a pair of blue and pink plaid, silk panties with bows on the hips, and stuffed them into my back pocket. I went back downstairs as if nothing had happened.
We hung out for a while, and then I went home. It was like 11, and my mother and little sister had gone to bed; my father was at work. I went into my bedroom, locked the door, and stripped naked. My cock was already hard, about 7 inches long. I laid down on my bed, and pulled out the panties from my pants pocket. I wrapped the inside of the crotch around my dick and started jerking off with them. It felt so good, the soft fabric tickling my cock as I stroked it fast and squeezed it hard.
Then, I took the panties off of my dick, and I decided to do something different; I put the panties on and wore them. They felt good, riding up against my asshole and squeezing my dick up against my body. I put my hand into her panties and jerked off, every time I stroked down feeling the soft fabric against the tip of my shaft. It felt amazing.
I began to imagine her bouncing up and down on my dick, moaning and screaming my name. I stroked faster and faster. The panties hugged my balls, and my shaft began to throb. As I imagined Annie riding me, I came in her panties. The stain spread all across the panties as I blew a good hard load.
I sat there for a few minutes in her cum stained panties; it was the best jerk I'd had in a while. I kept those panties and used them until they were worn out from my cum. I've done some other crazy things, but those are for another story