First Time Masturbating with a Girl

Growing up, our family often vacationed with my parent’s best friends who had a daughter my age. She and I spent a lot of time on vacation often in the same bedroom as well as spending nights together as my parents would go out late. We were like siblings, best friends who fought at times. 

In high school we weren’t together often, but one summer we spent a week at the lake, again sharing a bedroom. Nancy was blossoming into a beautiful young woman I found quite attractive but still considered a sister. I had long found her attractive, but never thought of her sexually.

One night, we were sitting on the bed playing War, the card game. We were being silly with the game and laughing a lot. Finally, after a long game, I’d won, but Nancy pushed the cards off the bed and started wrestling me. She was bigger than me at this stage and quite strong. 

I fought as hard as I could, but when she pinned me to the bed, she grabbed my crotch squeezing my now hard cock. I squirmed trying to free myself, but she kept me pinned and gripped my cock through my shorts. 

“Did I make you hard like this?” she asked teasingly. “You naughty boy!” she said jokingly. I felt my face flush with embarrassment. She kept gripping it. “I bet you like to play with it, don’t you? What do you call that? Beating off?”

What could I say? “Yes, I play with it. It’s called beating off.” 

“I want to watch you do it. We have at least an hour until our folks get home. I really want to see how it happens. I’ll let go when you agree.”

As much as I love having her holding my cock, I knew that it wouldn’t take much longer before her gentle stroking made me cum. “I’ll undress and do it if you’ll undress and let me look at you.”

She didn’t hesitate pulling off her flannel nightie which gave me the impetus to strip down and give her a show. I lay on my bed and she sat at the end of the bed with her legs spread to let me see her furry pussy. 

Trying not to cum too fast, I rubbed my nipples, inner thighs, and more with a light touch before I touched my ready-to-burst cock. When I began slowly stroking my dick, she licked two fingers and began fingering the outside of her pussy. I almost came, but kept the stroking slow to delay the orgasm. 

Looking at her young naked body for the first time since she’d developed really turned me on. This girl I always thought of as a sister is now a sexy young woman with a gorgeous body. Her tits were mesmerizing, but I had to look at her pussy when she began rubbing it. I stared intently as I continued stroking.

Nancy squirmed when she slowly slid her fingers deep inside her vagina and then began thrusting them in and out. I’d gone past my point of no return and was about to explode exclaiming, "Oh god Nancy, I’m going to cum hard!” just before my first spurt shot across the bed landing on Nancy followed by several other spurts not as intense.

Watching me intently as I spurted, Nancy began thrusting her fingers incredibly fast. Her orgasm was incredible to watch. She shook, she moaned, she yelled out. Her body pulsed uncontrollably until the climax passed.

We were both sound asleep in our separate beds when our parents got home. Her family moved out west and we never saw each other again, but oh what a memory!