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Grinding with Gretchen

''Feel me,'' she whispered, guiding my fingertips between her legs
Junior year I transferred to Pine Creek Academy, a private school where the tuition was more than the average annual income back home. PCA was known for its gothic architecture, serious academics, and liberal outlook. Anyone 16 years old with an honors grade-point-average, for example, was eligible for the mixed-sex dormitory known on campus as Chastity Hall.

I was still unpacking when there was a soft tap at my door. The girl who introduced herself as Gretchen, my new Residential Advisor, had blond ringlets, pale blue eyes, and a willowy frame that accentuated coltish legs that went on forever. Even in her PCA polo shirt and plaid skirt, Gretchen was achingly beautiful.

Unfortunately, as a Senior, and my RA to boot, she was clearly miles out of my league--as approachable as, say, Megan Fox. And Gretchen was, indeed, all business as she stood at my door reviewing the recycling rules, laundry services, quiet hours, and co-ed bathroom etiquette.

Then she checked her clipboard, and broke into a smile. "Cool! You're on the football team," she said enthusiastically, dropping the whole impersonal persona. "I'm on the Girl's Soccer Team. There's shuttle bus to the Athletic Center that leaves the dorm at 2:15. Don't be late, it won't wait!"

She turned to walk down the hall, but glanced over her shoulder at me. Her hair formed a perfect golden halo in the afternoon sunlight. "I'll save you a seat," she said with the kind of smoldering look that turns adolescent boys into groveling fools.

The 15-minute shuttle bus ride soon became the highlight of my day. The real Gretchen was as empathetic as she was hot. She took a genuine interest in my silly anecdotes about growing up in "Smallville," PA. Her descriptions of coming of age in New York City sounded like some kind of impossible alternate universe to me.

By the end of September, we were saving each other seats on the bus and even taking short walks around campus just so we could keep talking. It was on one of those walks that she asked, "Are you in a rush to get back?"

"For what?" I replied. "Frozen pizza and calculus?"

"OK, then. Let's explore," she announced, grabbing my hand and pulling me across the highway toward an abandoned dairy farm. As soon as we were out of sight of the campus, Gretchen pushed me against a barn, looked up into my eyes, and pressed her lips against mine.

"I've been wanting to do that for days," she said when we finally came up for air. At this point, the most important thing of my young life was to find a way inside that barn.

The front was chained, but a firm kick forced one of the side doors open. Inside sunlight streamed though chinks in the siding, revealing an old jalopy with no tires or engine, but a rear seat that was miraculously intact.

With the next kiss, Gretchen literally melted into my arms. I felt her lips part and her tongue caress my mouth, sending a cascade of shivers down my spine. A mere glimpse of Gretchen's naked thighs, or even the sweet scent of her perfume perfume, were enough to arouse me, so you can imagine the impact of a deep french kiss.

When we finally pulled ourselves apart, Gretchen was panting and looking me up and down through half-opened eye lids. In panic, I realized the outline my hard cock was plainly visible through the front of my khakis, and I shifted my weight in a futile effort to conceal it.

"Are you trying to hide an erection?" she giggled.

"Ummmm… guilty," I blushed.

"Don't be embarrassed," Gretchen said, her eyes searching mine. "I'm glad you're excited."

I didn't know what to say, so I just relaxed, and unclenched my legs. Gretchen looked at my lap and smiled.

"Look," she said, pulling the fabric of her white Pine Creek polo shirt down onto her breasts. She was not wearing a bra, and her stiff nipples poked against the soft pima cotton like a pair of hard, pink pencil erasers.

"See what you've done to me?" she whispered. With that, Gretchen slid down on the seat, her plaid skirt riding up her thighs until I could see the front panel of her panties.

"Come here, Horn Dog," she laughed, tugging my shoulders until I rolled over and my crotch pressed between her legs. "Haven't you ever seen white-cotton panties before?"

"Not… on... you…" I stammered.

"Kiss me again, and maybe you'll get to see underneath them one of the days," she teased, pressing her mouth against mine.

As our kiss deepened, I could feel her hips undulate beneath me, and I answered by rolling my own hips against the warm softness of her crotch. Gretchen moaned and her tongue plunged deeper into my mouth, her fingers stroking the back of my neck. I couldn't stop thinking about what she'd just said, about me seeing what was under those sexy white panties.

Soon, all that mattered was the delicious feeling of my cock humping the moist gusset of Gretchen's panties. Knowing all that separated me from the wonders of her pussy was a thin layer of fabric caused an almost unbearable excitement in me.

We would start slowly, savoring the new sensations of our entwined bodies. As the heat rose between us, our hips ground faster and harder until with muscles clenched, we hovered at the edge of orgasm. Only then would we relax, catch our breath, and begin another slow climb toward ecstasy.

Eventually, Gretchen's moans turned to whimpers that caught in the back of her throat. We were no longer kissing, just grinding with primal urgency. As we neared another peak, Gretchen's went rigid in my arms and cried out with enough force to scatter the flock of pigeons that had been perching in the rafters. And instant later, I ejaculated, my cock throbbing between as warm cum gushed into my briefs. I was dimly aware that Gretchen had wrapped her long legs around my back and was rocking me tenderly as a I came.

It took a long time for our breathing to return to something like normal. When Gretchen gently rolled me off her, she took my fingers in her hand.

"Feel me," she whispered, guiding my fingertips between her legs. I was not surprised by the heat radiating from beneath her panties, but I was shocked by the amount of slippery liquid.

"Is that from me?"

"No, you big dork!" she said, swatting the side of my head with her free hand. "I came. That's my wetness."

Before letting go of my hand, Gretchen pressed my fingers until I found the groove at the entrance to her sex. Taking the hint, I forced my middle finger as deep as her panties would allow, and was rewarded with a gentle shiver and another satisfied moan.

"Can I touch you?" she asked. Following her example, I guided her fingertips until they brushed against the outline of my cock. She explored it eagerly, squeezing me softly through my pants. When she reached the tip, her fingers strayed into the wet spot. She ran her fingertips across it and then lifted them to her mouth.

"Mmmmm… not bad," she said, running her tongue across her lips.

I reached back between her legs, drew my fingertips along the slick liquid on her panties. I was amazed to find my body shudder with pure pleasure as I licked her juice off my fingertips.

"You like my taste?" she asked with a naughty smile.

"Apparently, I do," I answered.

Gretchen kissed me. "That's good, because there's plenty more where that came from."

The next afternoon, as we stepped off the shuttle bus at Chastity Hall, she whispered into my ear, "Stop by my room after 10PM?" We both knew there was no need for me to reply.

The rest of the day dragged on forever. My heart was in my throat when I finally knocked on Gretchen's door that night.

"It's unlocked, Jason," she called out.

The only light was from a couple of flickering candles on her desk and it took me a moment to realize that Gretchen was sitting cross-legged on small sofa, watching me with that mischievous smile of hers. When I saw her, she patted the cushion next to her in an invitation for me to join her.

"Do you ever imagine what I look like naked?" she asked out of the blue, catching me completely off guard.

"What? No… no… of course, not!" I stammered unconvincingly.

"Liar," she smiled. "Tell me how you think I look without clothes."

"Well, tan lines," I began. "Bikini lines, actually, drawn my eyes to your breasts and the triangle between your legs."

"Mmmm… I like that."

"Your breasts are small and firm. About the size of tennis balls. With puffy pink nipples that get very stiff and erect when you're excited. Your torso is long and thin, so thin I can see your ribs. Your stomach and abs are absolutely flat and end in sharp V covered in pale blond pubic hair. Your legs are also thin, and impossibly long. And where they join there's a visible gap…"

"You must be psychic," Gretchen said, standing up and peeling off her tank top and shorts. It was hard to tell in the dim light, but I was correct about almost everything except maybe her public hair, which was so fine and blond as to be virtually invisible.

"My turn," she began. "Wide shoulders and with muscular arms and pecs. A narrow waist and hips with a tight butt. No wonder you play 'Tight End.' Flat stomach and abs with fading tan lines from a Speedo, no, make that Jams. A thick patch of curly dark pubic hair, I think. A pale penis, not too long, but not too short, and it sticks straight out when and bounces up and down when you're aroused… Am I right?"

"I suppose there's only one way for you to find out," I replied. I pulled my shirt over my head, then unbuckled my belt and in a single motion, pulled down my shorts and briefs. My cock was rigid and, indeed, bounced up and down as soon as it was free.

"I AM!" she exclaimed, clapping her hands in delight, her eyes locked on my cock.

With that, she gently pushed me back into a sitting position on the sofa and lowered herself onto my lap. At first I thought she was going to guide my cock inside her, and I could feel myself twitch in anticipation. But that wasn't Gretchen's plan.

Instead, I felt her fingers reach between us and part her pussy lips, spreading them over my cock shaft. By rocking our hips, we could make my cock slide between her moist lips without actually penetrating her. It was a sensation unlike anything I'd ever felt before.

We started slowly and began gathering speed, my cock gliding effortlessly between the moist heat of her clinging lips. Soon I could feel the sweat rolling down my torso as our bodies flowed together almost as one.

Gretchen turned her head upward and whispered, "Squeeze my nipples." I started by rolling her nipples between my fingertips, but soon found I could do an even better job by cupping her breasts with my hands while pinching her nipples between my knuckles. What I couldn't control was the sensation building in my balls.

"Ohhhhh, God!" I yelled. "Gretchen, I'm cummmmmmmming!"

Gretchen gave one of her signature squeals of delight and cupped her hand in front of my cock just as the first blast shot from the tip. With her other hand, she pressed me even more firmly between her legs so that every twitch my ejaculation vibrated against her swollen lips.

When I had finished, she she scooped up a few drops of my cum with the tip of her tongue before wiping her hands on a beach towel and cleaning off my cock.

Then, once again, Gretchen began to slide herself along my still very firm erection while at the same time, tracing her hand down the front of her stomach and over her abs. To my astonishment, she until her fingertips slipped between her pussy lips.

I'd never seen a girl masturbate and as her head leaned back against my shoulder, I peered down, watching her fingers rub small circles on what I now know was her clit. Not only was I seeing this private act for the first time in my life, I could feel her finger moving provocatively against my cock shaft. After my initial surprise, I resumed toying with her tits and nipples, trying to match my movements to Gretchen's increasingly feverish fingering.

Soon her breathing grew shallow and raspy. Her body stiffened, a long moan emerged from deep in her throat, and she clung to my naked shoulders with her head pressed into my neck. I realized I was still gently rocking my cock back and forth against her pussy lips. As her orgasm subsided, we collapsed onto the sofa.

When her eyes finally opened, Gretchen looked down at my cock, which was as hard as ever. "Your turn," she whispered to me, motioned toward my erection.

"My turn for what?" I asked naively, although I had a pretty good idea what she had in mind.

"To show me how you do it, Silly," she replied. "How you make yourself cum."

Up to this point, no one had ever seen me jerk off. At least, not that I knew about. But I couldn't deny Gretchen, so with my cheeks burning from embarrassment I reached down and wrapped my thumb and forefinger around my cock, which was already well-lubed with her juices.

"Wait," she said, pushing me off the sofa. "Do it standing up so I can see better." As I got to my feet, she pulled herself upright, bringing her eyes level with my cock. Even in the flickering candle light, I could see the intensity with which she watched my hand slide up and down the shaft.

To my complete surprise, watching Gretchen's eyes watching me jerk my cock was an incredible aphrodisiac which delivered a fresh jolt of excitement through my already overloaded nervous y. In what seemed like no time at all, I was fucking my hand and my cum was splashing across Gretchen's tits.

"Oooohhhhhh, Wow!" she exclaimed, scooping up a few drops on her fingertip. "That was sooooo cool… and tasty!"

Gretchen's sexual inventiveness was boundless. Almost daily we seemed to find new ways to masturbate each other, or for each other, often falling asleep in each other's arms. Sometime before Thanksgiving break, we added oral sex to our repertoire -- which Gretchen took as much pleasure in giving as in receiving.

By unspoken agreement, we managed to refrain from intercourse. Although if either of us had wanted it, the other would have surrendered without hesitation. It was the worst day of my life, when Gretchen tearfully told me that she'd been accepted at UCLA and intended to go.

Despite all that's happened since, we remain friends. Ironically, I now live in NYC, and Gretchen in West LA. We share our triumphs and tragedies, and sometimes talk long into the night. From time to time our whispered conversations even lead to mutual orgasms that bring back bittersweet memories. 

I suppose the good news is that although I've never found a partner as sensual or as uninhibited as Gretchen, the things we did paved the way for a lifetime of other sexual adventures. In a perfect world, everyone would have a first love like that.

* * * *


"Gretchen" is the first in a series describing some early, i.e. formative, sexual experiences. The names and time frames have been changed to protect the not so innocent and comply with the Lush TOS.

Next up is "Tracy's Mom," my affair with a thirty-something single MILF who rented the cottage next door when I was old enough to drive, but young enough not to know any better than to get involved with a lady more than twice my age. 

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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