A true story, your comments appreciated.
It was the summer following my Sophomore year in high school. I had just turned 16, and gotten my first car, which opened the door to dating, although I was inherently shy, and still very much a virgin. My forays into things sexual were extremely limited, consisting of nothing further than some pretty intense making out that included some fairly benign groping, and all of that outside of the clothing. As is common to all 16 year old boys, I was a walking poster child for hormone overload, and jacked off constantly, my mind reeling with imagined visions of the myriad of things I longed to experience with some willing young thing that had yet to materialize in my lust filled life.
Among my favorite masturbation fantasies was my friends younger sister, a nubile beauty not quite 14, but over flowing with budding puberty, and development. To say that I lusted after her is to say that Andy Rod.... plays a fair game of tennis, and finally, one day, my shameful prayers were answered in a very surprising way. I was driving alone along a well travelled roadway through my town, intending to drive out to a new subdivision that was under development, but not yet occupied, to check out possible sites for future make out sessions, or street racing, which was a popular pass time for my crowd. As I rolled to a stop at the main intersection in town, I spotted Linda, my friends sister, seated on a bus stop bench. I tapped the horn, and got her attention, and I felt my balls tingle, as she stood, and walked over to the car, smiling broadly. She was wearing a small, and very snug pair of yellow shorts, her creamy thighs fully on display, and the shorts moulded to the puffy outline of her pussy in front, and clung saucily to her perfect little ass in the back. Her top was a cropped tee shirt, equally snug fitting, and her pear shaped breasts made two enticing mounds under the shirt. The hem of the shirt had been cut off, leaving a wide expanse of her smooth, tanned tummy exposed, and, as she leaned into my car window, my dick went fully hard inside my tight Levis.
We chatted a minute, and I explained my mission, and she asked if she could ride along with me, and I, of course, agreed. She slid in, and surprised me by moving across the seat until she was snuggled right up to my side. I could smell the freshness of her, and a faint lingering of some type of cologne, and my dick throbbed, as her bare thigh rubbed up against my jeans covered leg. I managed to navigate to the deserted subdivision, and wandered aimlessly down one street after another, and was surprised once more, when Linda directed me to stop behind some high units of lumber. I stopped, and shut off the engine, then sat there trembling, completely unsure of what was going on. Linda snuggled in closer against me, and dropped her hand onto my thigh, and I all but unloaded into my jeans at the contact. I gulped, and managed to look at her, and she just smiled coyly, and asked if I liked her, and if I thought she was cute. Boldly, I slid my arm along the back of the car seat behind her, then, let it drop onto her shoulders, as I blurted out that I indeed did like her, a lot, and that I thought she was beautiful. She giggled sweetly, nodding, then simply asked me it I would like to make out with her, which I answered with a muffled groan, and a quick move of pulling her close, and kissing her soft, lush mouth.
Things heated up quickly, both of kissing passionately, our tongues duelling as though we had done this countless times before, and, as our mutual lust built, I again very nearly shot my load, when I felt her small hand groping my very tented crotch. I gulped, my heart hammering like crazy, as she gripped my rigid erection, and milked it over my stretched Levis several times, then, gasped again, as she attempted to shove her hand under the waistline. The jeans were far too tight, and stretched with my aching boner, for her to accomplish this, so, she very calmly said that we needed to move into the back seat. I couldn't believe any of this was happening, but, in a flash, we ended up stretched out on the back seat of my car, once more kissing, and groping. I managed to push up the tiny tee shirt until it gathered under her chin, and she opened her bra, releasing her small, but succulent breasts with their strawberry tipped nipples, and I mauled them, awkwardly tweaking the nipples, and generally making an idiot of myself in the process.
She chuckled softly at my feverish attempts to stimulate her, then finally tired of my lack of polish, and pushed me away, and firmly down onto the car seat. I lay still and watched then, as she once more explored my protruding erection with her delicate fingers, then, reached for, and unbuttoned the fly of my jeans. She slid her hand inside my white briefs then, and I nearly passed out cold, as her warm hand closed around my throbbing erection. She squeezed it, then began stroking it in a steady up and down rhythm, all the while staring into my wide eyes, and smiling. It may have taken all of a minute, two at most, when I suddenly became very aware that I was going to cum, big time! I groaned, my balls suddenly boiling over, and I felt my dick flex, and swell in her moving grip, then, I erupted, spewing what seemed like gallons of my pent up sperm onto my undies, and completely sliming her still pumping hand. She giggled sweetly, continuing to stroke my ejaculating dick until I was more drained than I had ever been in my life, then, calmly extracted her gooey hand from my undies, and wiped it off on the leg of my jeans. She leaned in, and kissed me then, saying something I never caught over the loud pounding noise inside my head, and sat up, re secured her bra, and settled her tee shirt in place. I fumbled with redoing up my jeans, then sat up, and we got back into the front seat, and I drove her home, as she chatted on about her summer plans, and school, never making a single reference to what had just taken place.
When we got to her place, my friend was there, and we went up to his bedroom, where he chided me for being seen with his 'lame' little sister, while at the same time thanking me for giving her a ride. I just shrugged innocently, telling him that she was actually okay for a kid, while at the same time I was secretly savouring the afterglow of the most intense moment of my young life. Linda and I repeated the action on three, or possibly four, other occasions, all of them mainly similar, with me toying with her pretty little tits some, and ending with her jerking me off into my undies. The following school term, I finally connected with a real girlfriend, and just sort of drifted away from Linda, but, she is fondly remembered to this very day!