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Learning by Example

Posted by: Age: 17 then Posted on: 14 comments
13 likes 39 views Category: Masturbation Female-Male Tags: first time, hand job, pillow humping
I spent so many wasted years not quite knowing how to pleasure myself, but it all made sense the first time I stroked off my boyfriend.

I somehow never quite connected the dots as a kid. Although masturbation is part of my earliest childhood memories, I had no idea what I was doing and definitely didn't even know what an orgasm was. ​​​​​​​I like to read the first-time stories here, especially the descriptions where the sensation sneaks up on someone for an explosive surprise. I wish that had happened to me in those early days. As it was, I would masturbate daily -- at night, in the morning, sometimes in the afternoons after school -- but it never ended in climax. I just sort of kept going until the feeling kind of resolved without an orgasm, the tension easing away, my interest fading. This continued for years.

Somewhere around middle school after sex ed, I realized what I was doing had a name and had negative connotations. I used to feel guilty about it and worried I was harming my development somehow. Sometimes I was so filled with guilt that I'd get paranoid when the cat walked down the hall when I was touching myself, scared that she might somehow tell on me to my mother. It was totally irrational, but that's what happens when a kid is left to figure everything out by themselves!

All through the rest of middle school and most of high school, I went through my life semi-enjoying these inept attempts sexual pleasure. I was shy and socially awkward, and I didn't date until my senior year of high school. Seventeen years old and finally had my first kiss! I felt like I had so much catching up to do, so despite being an oblivious and awkward virgin, I enthusiastically went along with whatever my boyfriend wanted. It was a few weeks into the relationship when I saw his cock for the first time. I was so sheltered, had never seen any explicit porn, and never quite understood the physics of the male anatomy until that moment, when there it was in front of me.

My boyfriend Ryan and I were up in his bedroom, alone in the house, a movie playing in the background as we made out on pillows on the floor. When he pulled his hard-on out of his pants, I was so nervous. "Touch it," he encouraged in a whisper between kisses. I touched it. I ran my fingers gently up and down. He had what I now know was an average cock, but to my inexperienced teenage self it seemed mind-bogglingly enormous. I had no idea what I was doing, how to touch him. After a few seconds of my clueless fumbling, Ryan reached down and covered my hand with his, guiding the strokes the proper way, before he let go and returned his hand to where it had been feeling up my breast. I kept going like he'd showed me. He was uncircumcised, and the foreskin glided up and down over his cockhead.

In the moment I remember thinking how much it reminded me of those "water snake" fidget toys from my childhood -- those plastic sleeves filled with colored water, does anyone remember those? It was a totally unsexy thought to have, and I pushed it away and concentrated on what I was doing. I was a fast learner and an eager student, and I carefully watched my boyfriend's reactions, glancing back and forth between the ecstatic expression on his face and the hard cock pumping beneath my hand. His cockhead seemed to grow more swollen and redder the more I stroked the foreskin over it, and it thrilled me to know that I was creating that reaction with my own hands.

"Fuck, yes," Ryan gasped. "Faster." I increased my speed and squeezed a little tighter. I couldn't help but smile at the way he bit his lip and squeezed his eyes shut, eyebrows furrowed into an intense expression of pleasure. His hips began bucking in time with my strokes, and wetness began to seep from the slit of his dick. I began to feel for the first time a deep-seated, urgent arousal I'd never felt before. As I watched his swollen cock pumping into my hand, listened to the involuntary moans and grunts of pleasure he was making, there suddenly was between my legs a warmth and wetness I'd never known. I started unconsciously moving my hips along with him, squeezing my muscles, feeling the ache of arousal throb through my pussy.

"Babe, I'm gonna cum." Ryan's voice was a strangled whisper. He forced his eyes open and looked at me plaintively. "That's okay?" Chivalrous of him to ask, I now understand. At the time, I wasn't entirely sure what was going to happen.

"Yeah," I answered, trying to keep the nervousness out of my voice.

"Oh, fuck." Ryan threw his head back and arched his back, then looked down at his cock. I looked down too. I could faintly feel it pulsing in my hand as white liquid shot out of the slit and landed on his belly. He cursed in rhythm with every spurt. "Fuck, fuck, fuck." The liquid stopped shooting and slowed to a dribble. As I kept stroking, it smeared onto my hand. I was still stroking, unsure of when to stop, so he reached down and held my hand still. "That was amazing," he said. I watched his dick begin to deflate where it lay against his belly in the puddle of cum. "Yeah," was all I could manage.

Later that night, after he'd driven me home and my whole household was in bed, I lay in the dark and thought about the encounter. The warm ache between my legs started up again, and I squirmed beneath my sheets. So that's what masturbation was supposed to end up with. That was the happy ending, not the gradual loss of interest and pleasure that I always experienced. That was the orgasm I was supposed to be having.

I couldn't take the aching any longer, and I grabbed one of my pillows and stuffed it between my legs. I turned around in bed so I was on my belly, straddling the pillow the way I wanted to straddle his lap, thrusting my hips the way he'd thrust his own as he fucked my hand. I pictured that cockhead flushing deep read beneath the foreskin that stroked over it again and again. I pictured the tension in his muscles as the pleasure built inside him, and my own muscles began to tense. I pressed all my weight down where it ached the most, that throbbing point that I now know is my clit, and I humped against the pillow as hard as I could. In my mind I relived the pulsing of his cock as it began to erupt, the rhythmic contractions that forced out the jets of cum, the way he cried fuck, fuck, fuck with every spurt. 

Deep inside my pussy, I felt it starting. It seemed suddenly like all the blood in my body was flooding between my legs, rushing in and creating a tension within me that I'd never known. My insides felt like a water balloon about to burst. I held my breath and grinded myself hard as the pulsing started. The same contractions that I watched in his cock now rippled through my pussy. I pressed my face into the bed to muffle the moan that was spilling unstoppably out of me. All too soon, the feeling passed. I relaxed against the pillow and caught my breath. Rearranging the pillows in their proper place again, I laid back in bed and marveled at the glowing sensation I felt thrumming through my whole body. I tentatively slipped my hand into my panties and brushed across my pussy lips, feeling the slippery wetness that had seeped out. 

From then on, my masturbation life changed. I still had a lot of learning to do; I couldn't always get there every time, and often had to settle for the gradual resolving of pleasure instead of the explosive orgasm I worked for. Over the years, I've perfected it down to an art, and now consider myself an expert. I wish I had made the connection sooner instead of wasting all those years on unsatisfying sessions, but I'm doing my best to make up for lost time now!

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