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Rory To The Max	By : Tricky_Dick Category: G through L > Gilmore Girls Views: 328 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not own Gilmore Girls nor do I make any money from this completely fictional story. I don't know Alexis Bledel or Scott Cohen.

Chapter List
- 1-Rory's First Time
- 2-Oh Tristin, My Tristin
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- 2
Rory explored her mother’s old room and while looking through an album of photos she found a picture of Lorelei and Christopher from 1983. They looked really cute together…. The picture made her smile. She continued to snoop and uncovered Lorelei’s diary. She flipped through and read a few pages here and there and then suddenly froze. Lorelei had and entry about losing her virginity to Christopher. At first, Rory felt guilty about reading what her mother wrote….. something so personal. But the story of how and why it happened got her very excited. It was romantic and passionate, and Lorelei didn’t leave out any details about the sex. By the time she was finished reading the pages, her panties were wet. Emily burst in and Rory put the book back and shut the drawer. The oven timer was going off….. the frozen pizza was done.

Later after dinner it was clear that the storm had lifted and the roads were safe. The phones were still down but just the same Rory wished to sleep in her bed that night. Richard and Emily summoned their driver to take Rory home.
Meanwhile Max Medina’s car had broken down in Stars Hollow. (how convenient) AND to complicate matters Lane had run her fingers through a classmates hair and was FREAKING OUT about it. Unfortunately, there was no Rory around to talk to. When Lorelei and Max returned home and found Lane there Lorelei counseled Lane and then urged her to go home before Mrs. Kim sent out a search party with St. Bernards and everything.

Rory arrived home and the house was dark. She crept into the house and passed into the living room and froze. There was a man on the couch. There had NEVER been a man on the couch before! Who was it? She wondered. [OH MY GOD IT’S MR. MEDINA!!] she screamed in her head. She stared at him as he slumbered and she couldn’t help noticing how the blankets had fallen away and Max had a boner! [HOLY COW… I CAN PRETTY MUCH SEE MY TEACHER’S DICK! I’M NOT SUPPOSED TO SEE THIS!] she thought…. And yet she couldn’t look away. “Oh Lorelei….. God that feels so good.” Max moaned in his sleep. [He’s dreaming about MY MOM!!!] she gasped in her mind…. But STILL she couldn’t look away. In fact, she even inched closer. Max moved his hand down and opened his pants, “Yes Lorelei….. I’ll do whatever you want.” He sighed as he reached in and pulled out his cock. Rory’s eyes went HUGE. First, she’s never seen a cock…. Not from Dean or anyone else… only pictures in biology books and the penis was shown flaccid. Max’s cock was HARD and thick and while it wasn’t sticking straight up…. It would throb and bounce as Max was unconsciously moving to an unseen blowjob. “Yes baby lick it…. Just kiss the head.” He moaned. Rory’s curiosity got the better of her and she knelt down next to the couch. Now her face was less than a foot away from her teacher’s cock. She fully grasped the situation and her logical mind told her to cover him up and go to bed…. But her animal brain was telling her to ‘touch it’. Nervously she reached out towards Max’s cock. She was so careful not to wake him. Her fingers just grazed it…. Max groaned and his hips arched to get more of her touch. “Ah Lor….. don’t tease me baby… please.” Rory felt almost compelled to touch it again only more deliberately. “MMMMmmmYES” Max moaned as her small hand wrapped around it and gave it the lightest stroke. “Come on honey…. Don’t tease me anymore. I know you want it.” Max mumbled. Rory saw the precum oozing from the tip of his cock. [This is CRAZY… but I’ve got to know.] she thought as she put her lips toward the tip and ever so gently licked the tiny bit of precum from Max’s cock. “AHHHHYES!” Max moaned again. Rory stroked his cock a bit more as she catalogued the taste of Max’s precum in her mouth. As more oozed out, Rory leaned forward again and licked the tip…. But this time she wasn’t fast enough to get away. Max unconsciously reached out and gripped her head pushing her mouth down around his cock as he groaned in delightful satisfaction. Rory was shocked and caught but Max didn’t wake up…. No no…. he just held her in place and began to thrust upwards into her mouth with his cock. He was dreaming of getting a blow job and making it happen in real life. Rory didn’t know what to do…. Max was her favorite teacher. Considering that she’d never seen a hard cock before… Max had a nice cock. He tasted good and with his hand on her head, there was little chance she was going to get away. Max pumped his hard cock into her mouth and Rory felt compelled to let him. She was terrified that if she forced herself off his cock, he’d wake up and she’d be caught. Max began to move quicker…. More of his juice oozed into her mouth and she felt Max grab her head with his other hand….. then he grunted and thrust into her mouth…. Before she could react, Max came…. His hot spunk coated her mouth and Rory unconsciously moaned which made his cock twitch. Rory swallowed…. She had no choice in the matter…. But what happened next was completely unexpected.

“Lorelei?” Max looked down at the brunette hair of his lover and as Rory looked up and their eyes met. Max was bleary eyed but it didn’t take long for him to recognize his student. “RORY?? Oh my God…. What just happened???” he sputtered. Rory froze like a deer in the headlights. She was completely guilty AND completely turned on. Her panties were soaked and she couldn’t believe what she had done. Max stared down at his favorite student with his cock STILL IN HER MOUTH and she was unconsciously sucking on it. “Rory…?” he said again. Rory realized that she was still sucking and let his quivering cock slip from her mouth. “Mister…. Um Max. It’s not your fault…. It’s my fault… I mean I didn’t mean to…. Okay I did mean to…. But then when you grabbed my head… but you were dreaming…. You didn’t know…. You couldn’t know…. you thought it was my mom…. And that’s okay…. Cuz I’m okay too…. Better than okay… I mean… I’ve never…. And it was crazy but also cool…. And….” She babbled. “Rory… this is so wrong… If your mom ever found out.” He started. “Don’t even say that…. My God. Promise you will never tell.” She begged. “No…. of course not. It will be our secret.” He promised. “Wait…. What did you mean by ‘better than okay?’” he asked. Rory’s eyes widened and she blushed. “Oh um…. Nothing.” She stammered. Max nodded at her and Rory paused and thought about it…. “I’ve never, you know, done that. So It was …. Uh….. good… cool…. I don’t know what I’m saying…. But I liked it….. a lot. Is that crazy? Is it wrong that I’ve got butterflies and other stuff?” she babbled. “Other stuff.” He asked. “You know…. I’m all ‘excited’”. She admitted. “Oh…. Well that’s completely normal and totally okay…. Not weird at all. “Even if you’re only performing oral sex, you can still get very aroused. Sometimes just thinking about giving oral sex can get a girl very turned on.” Max informed her. “Okay…. Well then that.” She grinned up at him. “Mister…. Sorry…. Max…. was that….. was I um…. any good?” she asked looking down at his cock. Max lifted her chin, “Rory… it was, you were excellent…. So good… really for your first time… it was an A+ performance.” He smiled.
Rory grinned and shook her head. All this talk had Max’s cock starting to harden again. Rory noticed it and stared at it. “It’s getting hard again.” She stated. Max covered it up. “Sorry hon…. I’ll cover it up.” He replied. “No don’t.” she asked and pulled the covers back. I’ve never seen one like this before. The textbook pictures are all limp. It looks pretty… I guess…. I mean sexy. It was so hard in my mouth…. And it tasted….. good. Can I touch it again?” she asked. Max just sat there with his mouth hanging open. Rory smirked at him and wrapped her hand around his cock. “Uh…. Rory… We can’t do this.” He sighed. Max’s resolved quickly melted as his adorable little student stroked his cock. “It so big and hard.” She said…. Making it throb in her hand. Max was helpless. On the one hand, this was a jail sentence for sure…. But on the other hand…. Her hands were so soft and she stroked it so nice and as he closed his eyes and enjoyed it Rory decided to try it again. “AAAHHHHHHH” Max moaned as Rory slipped his cock back into her mouth. “Rory stop…. Please… you… we can’t.” Max pleaded. Rory ignored his call for sanity. She was turned on and she had a willing participant who could never tell a soul. Rory didn’t need to worry about waking him up… so she pushed his cock deep into her mouth. “UHHHH” he groaned as this sweet nymph was driving him crazy. Rory was enjoying this experiment and she moved to get a better angle on her teacher’s cock. She bobbed on it and Max started to thrust up to meet her. She smiled around his cock. [I’m doing it right.] she thought.
Rory swiveled around so his cock slid more easily in and out of her mouth. [This is so much fun] she thought as Max was pumping and squirming under her efforts. She knew he had stopped resisting but what really surprised her is when she felt Max’s hand slide up under her skirt and right between her thighs. When his fingers touched her soaked panties Rory squeaked but Max knew what he was doing. His fingers traced right onto her swollen clit like he done it a million times. Rory stiffened for a moment and Max seized the opportunity and began to rub her clit. Rory moaned loudly around his cock and forced it deep into her mouth. Now the pair fully accepted what was happening. Rory’s hips rocked with Max’s fingers and Max pumped his hips matching Rory’s mouth to get the most out of her blowjob. Max rubbed Rory’s clit back and forth and then in circles. Rory twitched and moaned until her body stiffened and she came. Max wasn’t holding back anymore. He let himself enjoy this unbelievable situation. He slipped his fingers under the elastic of Rory’s panties and dipped his fingers between Rory’s sweet pussy lips. Rory purred as his fingers became coated with her juices. Then Max rubbed her juices all over her clit and rubbed it again. Rory squeaked louder and opened her thighs wider to give him better access. Max worked her clit and then pressed his fingers back into her tight pussy. Rory wiggled her pussy for him as Max pushed his fingers deeper into this tender virgin. Rory couldn’t believe what was happening but she did NOT want it to stop. Then she froze…. Max pressed two fingers up inside her pussy. It sent a wave of pleasure through her and as he began to rub the spot… Rory lost the ability to suck. She just moaned on his cock and sort of let him fuck her mouth from below. Max smiled knowing he had fully taken control. Rory moaned and groaned as she stuck her pussy up towards Max. Max grinned as he worked his upper body towards her ass. He took his free hand and pulled her panties down and in a snake like manner he forced Rory to roll onto her side as he used both hands to slip her panties off and push her thighs open. Rory was docile as his cock continued to pump into her mouth. Then she let his cock slip out of her mouth and she had to cover her mouth as a loud moan would have escaped her lips when Max began to lick her pussy. Max slipped his fingers back into her pussy and hit the spot again. Rory grabbed a couch pillow and squeaked into it as Max had her completely under his control. His tongue painted her clit…. He fingered her G spot and Rory bucked and thrashed as her pussy exploded. Max sensing her complete surrender decided that they were well beyond right and wrong…. He wanted her and he knew she wouldn’t or couldn’t deny him.

Max moved around her and scooped up the tiny teen. Rory put her arms around his neck as he lifted her up and carried her off into her bedroom. Rory kinda knew what was happening but now it got very real. This man was going to take her. Her favorite teacher was going to make love to her. She studied him as he set her down and began to undress her. He unbuttoned her blouse and removed it. He reached behind her and unhooked her bra and removed it. Then he stood her up and unhooked her skirt and tossed it. He looked deep into her eyes and kissed her. It was the most passionate kiss she’d ever had and to make it dirtier…. She could taste her juice in his mouth. Rory watched as Max removed his t shirt and now slipped off his pants and underwear. Rory slipped off her shoes and left her socks on. Max leaned in and kissed her again this time laying her down on her small twin bed. He opened her teenage thighs and relished in the succulent juices of the virgin. Rory immediately grabbed a pillow and moaned into it over and over again as Max went right back to work on her young pussy. Rory was a plaything for the adult. She was a happy little toy. She wrapped her legs around Max as he licked and sucked her pussy. His fingers danced inside her trembling channel. Rory bucked and cried into the pillow as Max tuned her up like a porn star. Rory was gasping as Max gave her multiple orgasms.

Max crawled over her and opened her wide. Rory held her breath as Max rubbed his hard cock between her puffy lips. Her pussy juice coated the head as he dipped it into her tight tunnel. Max then kissed Rory and reached up and pinched her nipple hard as his cock pressed into her cunt and tore her hymen. Rory cried into his mouth. The pain from the nipple pinch distracted her from her hymen tearing and Max sank all the way into Rory’s twat. He settled and waited. He kissed her and played with her nipples, nibbled on her neck and whispered into her ear, “You are the sexiest girl in the world.” Rory squirmed until she became more accustomed to Max’s thick cock in her channel. Max sensed that she was beyond the pain and he repositioned his legs outside hers and pushed her thighs together which was ideal for the twin bed. Max lay completely across her body and as his glistening shaft pulled out of her glorious gash it rubbed right against her clit. Rory felt a wild tingle just before Max plunged into her juicy juncture. “MMMMMMMMMMHHHHHHHHHHPPPPHH!” she moaned into his mouth. Max grabbed stuffed animal and pressed it to her mouth as he began to fuck his prized student. Rory was in heaven. Feeling this man take her virginity was beyond any experience she thought she’d ever have. And yes she worried about protection and all sorts of thoughts raced through her head about her promise to talk with Lorelei BEFORE fucking somebody but she never even contemplated anything like this happening. Max was hard as a rock inside this amazing girl turned woman. Her pussy gripped his cock like a vice….. He pumped and thrust as the teen moaned and groaned into the stuffed animal. Rory’s body was like a tripwire….. closer and closer she came to exploding until finally she clutched at him as hard as she could pushing her face into his neck and shuddering. “MMMMAAAAAHHHHHHHHHH” she cried into his shoulder. Max was beside himself with glee. He was fucking the beautiful and brilliant Rory Gilmore and her pussy was legendary. The best part was…. Since she already swallowed a load of his cum, he knew she’d do it again…. But more importantly, he was lasting so much longer than he would have otherwise and he was going to take advantage of that.

Max turned Rory over and pushed her face into the pillows. He then buried his throbbing shaft into the willing teen making her shriek into her pillows. The fucking was on again as Max held her hips firmly and pounded his conquest. He knew…. Just KNEW that he could have her whenever he wanted after this. She was his…. AND if he married Lorelei he could have them both pretty much at will. Max savored each and every thrust into this tight teen. Her pussy began to flutter as Rory clawed at the sheets and pillows through another mind-bending orgasm. Max was gleeful….. He was twisting and turning her into his little slut. She would do anything for him now. The idea of getting caught or Lorelei finding out was completely out of his thought process. All Max wanted to do was own this little girl’s pussy and he was in complete control. Rory tried to catch her breath and Max slowed down and leaned over her and kissed her. “You’re amazing Rory….. You’re the most beautiful girl in the universe.” He whispered into her ear and he slow pumped her cunt. Rory just kept backing towards the hard cock splitting her in two. “You like that hard cock in your tiny pussy?” he asked. “YEeesssssahhhh” she moaned. “You want me to fuck you hard again?” he asked. “YES PULLEEEZEEE Mr. Medina.” She sighed. Hearing her call him Mr. Medina sent a wave of lust over the man. Her rolled her over onto her back…. Place her ankles on his shoulders and then pushed the stuffed animal back up to her mouth. Then Mr. Medina began to fuck Rory hard and fast. Her body shook with the full force of this man pummeling and penetrating her as deep as possible. Thrust after thrust until her pussy clutched and trembled is bliss…. And then again…. And finally again. At that point Max couldn’t hold out any longer. He had far exceeded even his own hopeful expectations and he climbed over Rory stroking his cock and stuffed it into her mouth. Rory purred as his second eruption of the night filled her mouth with hot, sticky cream…. Salty and slick as it slid down her throat. Spent, the pair laid on her bed, happy and satisfied. Max kissed and cuddled Rory until she drifted off to sleep and then he got up and washed himself in the bathroom and dressed and went back to the couch as if nothing happened.

In the morning, Lorelei woke up before everyone and made coffee. When Rory showered and walked out to the kitchen Lorelei was surprised. “OH KID!... I didn’t know you were home.” She said. “Why is Mr. Medina on our couch?” she leveled knowing she had Lorelei on the ropes in the first round. “Okay well, his car broke down and the snow…. But nothing happened.” Lorelei confessed. “Well the storm wasn’t as bad as all that… but imagine my surprise to find my TEACHER sleeping on our couch.” Rory replied. “Yeah…. I’m sorry.” Lorelei said. Rory smiled at her. “It’s okay mom. I like Mr. Medina…. And I know you like him too. Just don’t break his heart okay?” she asked. “Got it.” Lorelei replied. “You look happy…. Did something happen yesterday at grandma and grandpa’s?” Lorelei asked. “Nope…. Just things are good. Happy to be home…. Need coffee.” Rory replied. Later when Max woke up…. He and Rory played it so awkward that nobody would have even the slightest clue that they had sex. The performance was epic but Rory knew nothing would ever be the same between her and her teacher.
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Rory To The Max