[GEMINIGUY]

[ORIGINAL; Fantasy
m/f Masturbation Cumshot 1st Time
m/F Oral Sex Anal Sex]

[Author's Note: I had originally made a Post here about Alexis Bledel being semi-nude on Mad Men sometime back, but it wasn't until after I bumped it and got several comments on it including Darklord's that I realized it's been a long while since I last posted a Gilmore Girls story! In fact, late October 2015 was the last time.
So I told myself, since I wanted to Post a story anyway, why not a Gilmore Girl story? I was thinking I'd love to see Rory get pounded - but wait, m.i.l.f. Lorelai getting pounded, that would be so hot. Then I thought of a way for BOTH to get cocked.
The subtitle is actually silly, and not totally accurate, but it was the first thing that came to mind once I had the basic story outline. I hope you enjoy "Gilmore Girls: Sharing Is Caring" ~ G]

[GEMINIGUY]

Disclaimer: THIS IS A WORK OF FICTION. THE AUTHOR DOES NOT CONDONE ANY SEXUAL ACTIVITY WITH PERSONS UNDER 18 YEARS OF AGE.

[January 1998 - Star's Hollow, Connecticut]

It was going to be a cold, snowy Winter in Northern Connecticut, where Lorelai Gilmore lived with her daughter Rory. But they were used to the cold weather, being life-long "Yankees". They actually loved bundling up long underwear, fur-lined boots, fur-lined hooded coats with layers of zippers, scarves tightly wrapped around their mouths.
Not that they were always outdoors in that cold weather. Often they were either at Lorelai's country inn or at home, both of which were well-insulated & well-heated. It was nice & toasty in both places.
Which didn't stop Lorelai & Rory from wearing heavy sweaters indoors & thick, insulated socks. And drinking LOTS & LOTS of hot chocolate! With marshmallows!
Rory had just turned thirteen this past October. Her young-looking mom had only been fifteen when she gave birth, putting her at twenty-eight now.

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People constantly thought the mother and daughter were actually sisters, and they did act more like close, loving sisters than they did mother and daughter.
Lorelai of course was much taller than her daughter, but both had long, beautiful dark hair, blue eyes and flawless skin. They both had amazing bodies as well, Lorelai at 36D-24-36, and Rory even slimmer, closing in on 34C-24-36. Their slim bodies made their already amazing breasts look even bigger.
The Gilmores had an unexpected guest at their home at the moment. Lorelai had had a tutor growing up who was eight years older than her. She had moved away before Lorelai had gotten pregnant with Rory.
Her former tutor had given birth to a son three years before Rory named Tim. She asked Lorelai if her son could stay with her for a while, she was in the process of moving back to Star's Hollow, but she and her husband were still looking for a suitable place to reside. They were unable to come back to Connecticut yet, but they were pretty much homeless.

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They didn't think it was fair to Tim.
Lorelai was happy to hear from her former tutor, who had actually became like a big sister to her growing up. And she was more than happy to take in her son for a while.
They put him on a plane and he arrived in Hartford a few short hours late. Since he was sixteen and had his license, he was able to rent a car to drive the rest of the way to Star's Hollow.
It was all new to Tim, having lived in one place for his whole life, but he was an adventurous boy, and up to the challenge. And the cold.
When the boy arrived at Lorelai's home, both mother and daughter were lovestruck at the sight of him. Tim was over 6'4", dark-haired, dark-eyed, ruggedly handsome and well-muscled. They did their best not to make their desires obvious to the boy, OR each other.
Of course Lorelai knew he was too young for her. And Rory, still a virgin, knew hardly anything about sex and boys, was somewhat shy around Tim. She felt she was too young and "too country" for the older city boy.

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Lorelai led him upstairs - Tim couldn't help staring at her perfect ass squeezed into those tight, tight jeans, and her slim thighs as well - to one of the spare bedrooms down the hall a bit from Rory's. She wasn't even thinking about how Tim did with the ladies, trusting he wouldn't be interested in her much younger daughter without even consciously thinking about it. Lorelai pointed out where the bathroom was, and what time dinner would be ready, and headed back downstairs as the boy unpacked.
Over dinner, it was Lorelai doing most of the talking, asking Tim questions, mostly about how his mother was doing, what was his father like, how had life been where they'd been living. Rory was mostly quiet, not sure what to say, what wouldn't bore the gorgeous city boy to death. From time-to-time, something Tim would say would make Lorelai ask Rory something related. Neither Tim nor her mother noticed the girl blush as she'd reply. All-in-all, Lorelai considered it a successful dinner.

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Tim went back to his bedroom, stripping down to t-shirt and sleep pants, keeping vigil. He wanted to see exactly which bedroom was Rory's when she came up to turn in for the night. Once he had that vital information, he settled down himself for the night.
Tim was very popular with the girls back home. Even the pre-High School girls went gaga over the older boy. After all, boys their age were so immature.
The boy had to admit, he preferred the girls who weren't in High School yet. He got off on their inexperience, their eagerness, their tight, tight pussies... He'd racked up A LOT of young virgins over the years.
But to Tim, none were cuter than innocent Rory. He loved the quiet ones. They were the sweetest...
The boy slept lightly for a few hours, until he was sure the girl's mother was fast asleep. After one in the morning, Tim made his move.
Rory was sleeping comfortably, cozily, and toastily, under a pile of comforters, also wearing her favorite flannel nightgown and a pair of insulated socks.

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Rory loved to be warmest in her own bed.
Tim slipped out of his bed, tip-toed to the door & listened. It was as quiet as a church out there. Easing open the bedroom door, he slipped out, closing it again behind him. Then he tip-toed down & across the hall to Rory's bedroom, hoping she hadn't locked it...
He turned the knob. She hadn't.
Grinning, Tim eased open the door & slipped inside, closing it behind him. He saw Rory asleep in the moonlight, the most serene, "angelic" look on her younger-looking than thirteen years old face. He wondered if she was dreaming.
He only wondered for a moment, as he tip-toed across the bedroom, slipping under the covers with Rory. She slept on, unresponsive.
Tim slid his hands over to her, feeling the warm flannel. He worked it up to her waist. Soon he felt the softer cotton of her underwear. He began to ease them down. Rory continued to sleep the "sleep of the just".
Slipping her underwear off of her, the boy slid his hand up the inside of her coltish leg, up her thigh.

[GEMINIGUY]

Soon his fingers were buried in the tangles of her unshaven pussy curls. Tim pressed his middle finger between her pussy lips, and his thumb against her clit. And he began to slide his finger up and down Rory's virgin slit as her strummed her clit lightly.
The girl didn't react at first. But her body temperature began to climb. That was what finally woke her up, when she got too hot under the pile of comforters.
Rory threw back her covers, the heat unbearable. And that was when she felt the hand on her young pussy, which had already began to moisten.
The girl gasped. She sat straight up in bed, clicked on her bed side lamp, and spun her head around.
"Tim!" She gasped, careful to keep her voice low. Who else would it have been?
The older boy smiled at her, and Rory's brown nipples immediately stiffened in her bra. But soon she found her eyes drifting downward, stopping at the massive bulge tenting his sleep pants. Rory's eyes widened.
She didn't know what to say. So she just let it happen.

[GEMINIGUY]

Rory started to moan. Her body temperature continued to rise. Grabbing the hem of her nightgown, she whipped it over her head, baring her very slim but already curvy body.
Tim admired her flat stomach, but even moreso admired her largish breasts tightly pack into her white cotton bra. Rory could feel his eyes on her young breasts, and blushed.
"Take off your bra for me?" Tim whispered.
Rory found she couldn't say no to the older boy.
Reaching back, she unclasped her bra, then shrugged it off of her shoulders, tugging it down her arms, before the cups pulled away from her high, firm breasts.
Tim marvelled at her amazing breasts, the large, dark brown oval-shaped areolae. He leaned over and sucked one of her throbbing nipples into his mouth. Rory gasped.
Tugging his cock out of the fly of his sleep pants with his free hand, Tim took Rory's right hand and placed it on his bare cock. The girl gasped once again, unbelieving that she was actually holding a real, live cock.

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He wrapped his larger hand around her dainty one, and began to move it up and down on his cock. When Tim was sure she understood what he'd wanted, he let go, and Rory kept stroking him as he switched nipples, leaning across her to do so, and rubbed her pussy and clit faster.
Rory moaned louder as he pleasured her, and she instinctively started began to jerk him off faster. Her loins felt like they were on fire, and that fire had spread up and down throughout her fragile young body. But the sensations gre even more intense between her legs, where she was now soaking wet with her juices.
The girl whimpered, breathing heavier as Tim strummed her clit faster. She was grinding her crotch up against his hand without realizing it herself.
As her body writhed and squirmed, her pussy started to spasm in orgasm. Tim kept strumming Rory's clit, as he slammed his middle finger and index finger into her pussy, tearing apart her hymen as he did so. Rory was far from noticing, the orgasm still washing over her body.

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Rory was still masturbating the older boy rapidly, as her orgasm slowly began to subside and she was regaining her senses, that was when Tim grunted, and started spewing jizz all over her.
Rory gasped, but couldn't stop jerking off his huge cock, as rope after rope splattered all over her largish breasts and belly. Tim spurt twelve or thirteen times, before the flow petered out.
He was still fingering her pussy, stretching her open a bit more. Finally the boy pulled his fingers out of Rory and mounted her. Her eyes widened. She knew what he was going to do. Part of her wondered if she should stop him. Another part didn't want to. Not that she could speak anyway.
Grabbing his cock, Tim guided it to her dripping opening, and started to push into the girl. Rory bit her lower lip, as he pushed his cock inside of her, stretching her young pussy.
Tim couldn't get all that deep in her at first. He began to pump his cock in and out of her, in and out. Rory gasped and moaned, eyes closing, head lolling back.

[GEMINIGUY]

He began to increase his speed, as Rory moaned louder, writhing wildly under him. Faster and faster he fucked her, his cock pushing further into her, stretching her open more, as she convulsed, her head thrashing from side-to-side.
As her convulsions increased, her pussy spasmed around his cock more powerfully, and as she threw her head back about to scream in orgasm, Tim bent forward, locking his lips on Rory's, as she screamed into his mouth.
Tim never slowed his pace. Her orgasm seemed to go on and on, once it faded [and Rory thanked him for containing her scerams], her pussy started to relax, and he was able to sink more than half of his length into the younger girl, and began to fuck her even harder and faster.
Rory came quicker, her orgasm hitting her harder and lasting even longer as he again kissed her to muffle the screams. The girl came A LOT, multiorgasming often as well. Tim lasted ove fifty minutes the second time, before kissing her once more as he cried out, pumping out another heavy load.

[GEMINIGUY]

He exploded deep inside of Rory, filling her pussy then her womb with his seed, much of it spilling out of her, splattering on her coltish inner thighs.
As Tim pulled out, he saw Rory was a mess of his jizz oozing down her breasts, belly, pussy and now thighs. But she didn't seem to care. She was utterly exhausted, smiling from the afterglow of their hot fuck, and quickly fell asleep.
Tim slipped out of her bed, leaving Rory the way she was, figuring she'd take care of it [once the jizz dried and her body started to get cold again, the girl did pulle the comforters back up over her body in her sleep] as she slipped from her bedroom and back into his, falling asleep fitfully.
Tim woke early in the morning, feeling AMAZING! Rory on the other hand overslept. The boy stripped out of his t-shirt and sleep pants, threw on his robe and went to take a shower. He sure hoped Rory did the same when she woke up before her mother could find out what had happened.

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Once clean as a whistle, Tim dried off and went back to his room. He slipped on a clean pair of fashion briefs, his jeans and a Heavy Metal t-shirt. Remembering it was colder her, the boy slipped on a pair of socks as well.
Heading downstairs, Tim could smell breakfast cooking, doubling his pace.
Lorelai heard him come into the kitchen, turned her head and smiled.
"Good morning!" She said, before turning back to the stove. "How did you sleep?" She asked.
"Fantastic!" He said, staring at her ass in another pair of tight, tight jeans. Then without meaning to he added "Just like that ass..."
Tim had been attracted to grown women before. He just never hooked up with one. He had to admit Lorelai was one of the hottest ones he'd ever laid eyes on...
Of course Lorelai had heard his comment. She smiled, feeling flattered a teenage boy love her ass. But he was still too young for her, so she planned to pretend she hadn't heard.
At least until she shut off the stove and turned around.

[GEMINIGUY]

Lorelai found Tim rubbing his cock through his jeans, his very large, hard cock...
The older female smiled. She just couldn't resist. Walking over to Tim, she dropped to her knees, unbuttoning & unzipping his jeans. She fished his cock out of his briefs & immediately started to suck on his huge log.
Tim was actually shocked. He hadn't expected the grown women to do such a thing. Plus he didn't get his cock sucked all that often. Most teenage girls thought it was gross, and rather jerk a cock or feel inside of them. Not that Tim ever complained.
And Lorelai was one HELL of a cocksucker! It wasn't long before his thick shaft was actually easing down her throat. And soon she was sucking on his cock rapidly, moaning around it as her nipples stiffened in her bra.
Lorelai started using her tongue. Back when she sucked a lot of cock, she'd always loved raking her tongue up & down the underside of a cock. That seemed to be a guy's weakness. It always made them cum quicker, & she had always LOVED the taste of cum.