Her High School Anal AdventurebyJack_Love©
*all persons depicted in this story are at least 18 years of age*
Back in high school, Jessica Esposito was the hottest fucking babe there was: an stacked 18-year-old brunette bombshell with a beautiful cascading mane of hair that was so long it would tickle her ass when she was naked. She had those gorgeous thickly-fringed huge clear brown eyes that only teen girls have; deep provocative inquisitive innocent wells. She had huge, round, overly-developed tits, a big, gorgeous pear-shaped ass flaring out from her miniscule waist like a bell, amazingly long, smooth slender legs, wide, full, pink smiling lips, and skin as pale and clear as milk. Her voice was always confident, bubbly, playful, feminine, and oh-so-sexy.
She got around, too. But something was always so friendly and intelligent about her that, although she surely fit the description 'slut,' I never really thought of her like that.
Hers was the first asshole that I ever fucked. Here's the story:
She was years ahead of all of us, intellectually, in terms of maturity, and of course, sexually. In fact, it was she who arranged the fateful camping trip. It was to be her and five guys, me being one of the lucky dicked chosen-ones. There was Jim: the lazy dope-head, Carl: the outdoorsy type, Jason: the shy guitarist, Steve: the lazy drummer, me, and our single ying-counterpart: the beautiful miss Jessica Esposito.
"Come on guys!!" she shouted excitedly as we were packing the van. Her short, pink miniskirt, 'Megadeth' T-shirt (no bra) pink running shoes, and calf-height white socks hardly seemed like camping attire, but the weather was hot, and so was she, so...
We all tried to please her, conspicuously helping out all over the place, being overly-friendly, and basically kissing her ass in every conceivable way possible; utterly pussy-whipped young cocks, the lot of us. ...Cocks which, unbeknownst to us, would be rewarded with the privilege of fucking her tightest of holes in just a few short hours.
We rolled into our campsite and began setting everything up: the tents, the bonfire, the food, etc. Jason was strumming lazily on his acoustic guitar; the windswept romantic; 'dyin' for love' (and dyin' for pussy) Carl in his plaid lumberjack-shirt chopping firewood, hoping to impress Jessica with his manliness (not quite ripened yet, though it was) Jim sparkin' up a fatty, Steve fiddling around with dinner, and Jessica and me behind the van speaking low.
"I think you're a very special girl, Jessica," I crooned cheesily, my motives less than saint-like.
She smiled and came close to me, her nipples almost touching my chest through her tightly-stretched T-shirt, "Thanks..." she said smiling, playing along.
I reached behind her and gently grabbed a couple handfuls of her gorgeous, sizeable, soft, round, teen ass-cheeks through her miniskirt.
"Oh my!" she cooed smiling in mock-surprise, and returned my embrace.
Her huge, soft boobs now pressed firmly into my chest; I could feel her hard nipples through Vic's wired-shut skull. We kissed, gently, passionately, and wetly. My hands crept under her miniskirt, and soon I was kneading her sweet, bare, warm, young bum-cheeks in my hands. Reckless, adolescent lust was quickly building up between us like the static before a storm...
I could feel that she had on the skimpiest of thongs, which I cheekily slid my fingers beneath so I that I could caress her asshole and pussy directly. Meanwhile, I pressed my hard cock into the fold of her pussy through our clothes. I could feel her pussy getting wet with my fingers. Our breathing was quickly becoming heavy and ragged...
"Holy shit you guys!! Pppppfffff!" It was Jim, already fucking stoned, and having the giggles.
Jessica just giggled too, not the least bit uncomfortable, and seductively waved him over towards us. The wasted young man stumbled up to us grinning, slightly red-faced and embarrassed.
"Is she not the fucking hottest girl you've every seen?" I asked Jim rhetorically while staring into Jess' dreamy, teenaged eyes.
"Pppppfffff! Fuckin' A!" he says without the least bit of tact, totally spellbound (and indubitably totally turned on) by our gorgeous, young female host.
"C'mere," Jess says to Jim smiling, "and feel this for me, will ya?" as she guides Jim's trembling hand onto her huge, warm, soft boobie, with its big, hard nipple...
As his fingers touched her awesome, welcoming mam, Jim nervously made a desperate little sound indescribable except to say that it was reminiscent of a chicken's sudden cluck- "Ounh!" and his poor face looked sickish. His overwhelmed little heart was a strong mix of horny-as-all-hell, awestruck, grateful, and sheer nervousness. Jessica just laughed at his awkwardness putting him somewhat at ease, his erect young dick pressing out desperately from inside his faded jeans.
The three other guys came 'round the van to see what was the commotion, to the sight of Jim groping Jess' tits through her shirt, and me groping her ass underneath her miniskirt. Jessica had her eyes closed and was moaning out loud in pleasure.
"Holy fuck, you guys!! Lemme in on some o' that!" shouted Carl, wide eyed and stampeding towards us leaving a vapor trail of pubescent testosterone in his wake.
She let us all grope her simultaneously, then introduced some order by lining us all up standing against the van. She then had us all jerk our cocks as she blew us one by one! It was a fuckin' dream come true for us I tell you, man!
Her warm, soft, wet, teen mouth was like heaven as she sucked our dicks. She didn't make us cum yet, but told us to keep jerking our cocks, and stay hard. She stared up into my eyes as I fucked her gorgeous, hot, wet mouth. I reached down and grabbed her boobs as she slid her mouth up and down the length of my shaft, sucking me hard, sending me to heaven. I just watched and jerked off as she did the same to the other guys.
We then sojourned excitedly to the picnic table where she sat on the edge on a soft blanket, slid off her moist neon-yellow thong, and spread her long, gorgeous slender legs for our viewing pleasure. And viewing pleasure it was indeed, to see her sweet, perfectly waxed smooth teen cunt with its fleshy, self-parting lips, and its sweet, young sex juices slowly oozing out down onto her also waxed-smooth asshole, awaiting our stiff, virginal young rods to fuck her.
"Ppppppfffff!" went Jim inappropriately, staring incredulously into Jessica's cunt, his long, straining hard dick in his beating hand, his hips bucking slightly beyond his control. Actually, it was quite funny to see.
"Fuck me..." Jess said, smiling back at him, obviously flattered by his state of total sexual hypnosis.
Poor Jim could barely keep from cumming as he placed his young cock into her Cradle of Ecstasy and thrust slowly forwards. It slid easily into her hot hole, and once again he let out a strange, embarrassing sound not unlike the sudden cluck of a chicken, throwing his head back in obvious, if slightly nervous, rapture. She slid her tight T-shirt up over her mammoth boobs, letting them flop out, naked, in the open air, and Jim grabbed them like a hungry monkey goin' for a bunch o' ripe bananas. His whole body sweated quivered slightly beyond his control, and it seemed like a wonder that he didn't shoot his load right then and there inside of her.
Next, I slid my rock-hard cock up her wet hot pink young fuck-hole. It was fucking heavenly as you may well imagine. My cock pushed some air-pockets out of her sweet velvety young love-tunnel, making her pussy fart or 'queef' as I fucked her hard and deeply. "Ooh!! Ooh!! Make my fucking pussy fart your name!!" she cried squinting her eyes in ecstasy, her wet pussy queefing noisily as I gripped her boobs, jerking my cock in and out of her sweet hot tight wet young pussy-hole. I slapped her tits as I rode her sweet cunt...
We all took our turn fucking her soft pink young fuck-hole (the first time ever up inside a girl for some of us, I suspected!) until she announced the shocker:
"Now I want all you guys to fuck my asshole... Then you're all gonna cum on my asshole and we're gonna take pictures of it! Ok??" Our jaws dropped in unison. "Ppppppfffff!" went a quivering Jim. "I'll go grab my Polaroid," I said rushing away to go find it quick, my dick bobbing in the breeze as I raced away.
We were like a group of young fuck-happy dumb clowns, all just grinning and nodding an eternal 'yea' to this vixen's continuing lewd suggestions, jerking our young yearning meat-shafts like a pack of idiots.
She got into doggy position on one of the seats of the picnic table, thrust out her gorgeous ass and lubed it up with some KY that she seemed to have conjured out of thin air for the first guy in line. "Ok you cock, fuck my asshole, stud!" she enticed.
I was first, and slid my cock deliciously up her hot, tight, brown fuck-hole, all the way up to my balls. She let out a moan, and so did I; my first time ever up a bitch's asshole! It felt indescribably good, as you may well imagine. I fucked her asshole slowly at first, then faster and faster, slapping my sack into her smooth glistening pussy below with my every thrust up her arse, kneading and slapping her gorgeous young ass-cheeks with my hands as I fucked her awesome, tight shit-hole.
"Uh! Uh! Yes! Yes! Fuck my ass!!" Jessica moaned as I rode her. We were like a couple of dogs; a couple of horses, tigers, or whatever. The occasional air-pocket made her ass fart as I drove my dick deep up into her bum, which somehow just turned me on all the more. It was hot as fucking hell. I pulled out and her asshole gaped open wide, growing and shrinking like a sexy little mouth in the center of her ass, winking at me like the eye of an angel. It looked like a fish's mouth, except it was a girl's asshole.
I sank my my meat back in her posterior to the hilt and snapped a few POV Polaroids for posterity. I eventually made way for the next young buck.
We all took our turn up her butt, Jim nearly nutting (not that I blame him in the least!) and I snapped a Polaroid for each of the guys. The tight walls of her asshole, so hot and slippery upon our cocks, drove us near madness. Jess came three or four times at least. 'Twas fucking awesome, to put it mildly.
"It's time to cum now, boys!" she said breathily. "I want you all to jerk off one by one and cum on my asshole, ok? Except just one of you, how 'bout the man who brought the Polaroid, can cum up my ass, ok?"
I nearly fainted with elation that I was gonna get to cum up Jessica Esposito's ass, but quickly got a hold of myself in order to complete the task at hand. We nodded idiotically as she got back up onto the table, putting both her legs to one side and spreading her ass-cheeks wide apart for us. Her asshole looked up at us like the fantasy-come-true that it was. Each of our hard, throbbing young dicks oozed pre-cum desperately in our stroking, trembling hands.
So I was first; I planted my sausage back up into her rectum and anal fucked the teen babe for a while before pulling out to see he asshole gape once again. Then I slid just the tip of my hard dick back into her tight shit-hole and slid my fingers back and forth along the length of my cock until I came up inside her, "Ooh, shit!" I breathed, squeezing her huge, gorgeous tits as I came, thrusting my cock deep up her fanny, my hips fucking her beyond my control as I snapped a Polaroid or two of my cock cumming up her bum.
I finally pulled out and it was poor Jim's turn next. Jessica watched him, smiling playfully as he approached her slowly, jerking his hard meat in his hand, his face looking weirdly sickish as he stared at her bum. He barely had to jerk himself off for five seconds before he was moaning and cumming all over her asshole which she had been holding spread open for him... "Aaah! Aaah! Aaah!" he wailed mindlessly, stoned, and shooting his sperm all over her spread open asshole, pussy, and ass. Jess moaned softly with him as he came.
Next, Carl sidled up to her staring at her arse, trying to look more confident that he was, sliding his fingers back and forth along his rod... until he came too, blasting a big load of hot jizz all over her bum, adding to the cum already there, abandoned in lust... "Oh- fuck, Jessica, I love you!! I want to marry you!!!" he cried inappropriately, his dick still spasming and spurting cum onto her hole. Somewhat embarrassed, he made his retreat from the gorgeous smiling young feminine holed creature.
Jason went up to her next, staring transfixed at her asshole, jerked his dick and came quickly; probably one of the best moments of his life.
Steve then made his approach to her ass, staring as we all had directly into her tightest of holes. He jerked his dick for maybe half a minute and then came hard... "Holy fuck, babe! You are so fucking hot!" he moaned as he shot his cum hard all over her soft, hot, sexy shit-tube, pussy, and ass. The pile of cum thereon from all of them by then was sort of impressive, not to mention mine which had begun to drip from her asshole. I'd made sure to try and snap a pic of each of the guys cumming, and now I snapped a few of the finished product. Jessica was simply glowing and she posed quite willingly.
"Now watch this, guys!" she said at last.
She turned around and squatted atop the picnic table, her cum-dripping ass hanging out over the edge towards us. She flexed her ass muscles and shat out my cum, a little white stream of jizz dripping down from her asshole to the earth. The Polaroid camera caught the moment. Four loads of jizz dripped from all over her ass and pussy, as my own load amidst some farts, pooped out of her arse before us, and I, for one, was getting hard again from this horny spectacle! We all just stared, mouths agape, wide-eyed, our cocks hardening...
"Ha ha ha!" she laughed delightfully as she grabbed a towel and wiped off her ass with it. She climbed down and put her clothes back in place. We were awestruck!
Soon afterwards, Jim lit up another fatty, Jason resumed his windswept strumming, and everyone was happy, our tragic little broken adolescent hearts overcome with gratitude wonder and spent lust. We had taken part in the stuff of legends. The goddess Jessica was glowing like a firefly. ...And I made sure the towel she'd just used to wipe our cum off her ass found its way to the garbage can.
Just then, a huge van pulled into the adjacent campsite and out poured eight more fucking hot little young 18-year-old high school girls! And the driver was also a smoking-hot young woman, in around her 20s...
But I'll save what happened next for another time!