Gilmore Girls Ch. 2

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Rory's first time.
2.2k words
4.51
180.5k
16

Part 2 of the 2 part series

Updated 10/24/2022
Created 11/01/2002
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Rabbit77
Rabbit77
15 Followers

"Oh Jesus! Oh Jesus! Oh Jesus!" Rory Gilmore screamed, as her mother pumped a dildo in and out of her tight young pussy. Ever since they first fucked a week ago, they couldn't keep their hands off each other. Although they had been best friends and incredibly close before, it was nothing compared to how their relationship was now. Mother and daughter, best friends, lesbian lovers…the only thing that bothered either of them was that they hadn't been fucking for years. But whatever they might have missed out on, they were certainly making up for now.

"That's it, Mom! Give me that hard fucking cock! Jesus, that feels so fucking good in my cunt. Oh Jesus…" Rory was on her hands and knees on her mother Lorelai's bed, as Lorelai fucked her from behind with the strap-on dildo. Her perfect little teenage tits jiggled ever so slightly, as her mother pounded her relentlessly. Even though her hair was messed up and she was sweating heavily, she still looked incredibly beautiful. Although she was 18 years old and sported a healthy B cup, she was often mistaken for much younger. With her innocently angelic face and smooth clear skin, she sometimes looked like a girl barely entering puberty. She didn't look so innocent right now, however, with her firm round ass up in the air and a big dildo fucking her unbelievably tight virgin cunt.

Since Rory and Lorelai did everything together, Lorelai wanted to be the one to take her daughter's cherry. She first fucked Rory with her smallest and most petite dildo, then gradually worked her way up. Last night, they had both decided that Rory was finally ready for her first taste of a real life cock. So Rory invited her boyfriend, Jess, over for dinner that night. Although she had been dreaming all day of how his cock would feel inside of her, right now all she could think of was her beautiful mother, as the inevitable orgasm washed over her.

"Oh fuck, that's it. I'm fucking cumming! I'm fucking cumming!" she screamed, as the intense pleasure rolled over and she collapsed onto her stomach. Lorelai pulled out of her, then lay down next to her and kissed her tenderly. She stroked her hair and kissed her neck lovingly, while Rory lay there exhausted.

"God, Mom, that was incredible. Do you think it's gonna be that good with Jess?"

"I don't know, sweetie" Lorelai responded. "It's hard to tell with teenage boys. They're usually eager enough, but sometimes they don't really know what they're doing. But don't worry, I'll be there to help you guys out. Remember, little girl, whatever you need I'm always gonna be there for you."

"Oh, Mom. I love you so much." Rory put her arms around Lorelai and hugged her tightly, as their naked tits pressed up against each other. She then lowered her head and started to suck on her mother's hard nipple, while sliding one of her hands between Lorelai's scrumptious thighs. She slowly made her way down to Lorelai's soaking bush, as Lorelai purred in delight.

"Mmm, I've taught you well, little one. Yeah, that's it, that's it. That's…Shit!" she exclaimed, as she heard the doorbell ring. Jess must've decided to be on time for once in his life. She'd never liked that kid, and she downright hated him at the moment.

"That must be Jess!" Rory squealed. She popped up excitedly and ran into her room to put on some clothes. Lorelai gazed longingly at her little round ass as she ran, so filled with love and desire that she thought she was gonna explode. "Could you get the door, Mom?" Rory called out. "I need to get dressed."

"Sure thing, honey." Lorelai got out of bed and threw on a short wraparound skirt, not bothering to put on any panties underneath it. "I doubt that I'll be needing them tonight," she thought to herself. She then put on a tight Velvet Underground t-shirt and looked at herself in the mirror. Her firm round tits looked great in the shirt, as her still rock hard nipples poked out obscenely.

She walked down the stairs, as the doorbell rang again. "Hold on, hold on!" she yelled. "I'm coming." She reached the bottom of the stairs and opened the door, where Jess was standing on the front porch. Although she couldn't stand the little punk, she could understand why Rory was attracted to him. With his dark good looks and bad boy persona, he was just the sort of boy who she would have fallen for at that age.

"Hey, Lorelai. Can I come in?" Jess asked.

"Knock yourself out. Rory's upstairs getting dressed. You can go wait on the couch until she comes down."

"Yeah, whatever," he replied. He walked past her and into the living room, while she closed the door behind him. He certainly was a sullen little punk, Lorelai thought. But Rory liked him, so she guessed that she would have to as well.

"Man," Jess thought as he sat down on the couch. "Lorelai is so fucking hot!" Although he didn't like her any more than she liked him, he could never get over how incredibly beautiful she was. Those tits, those legs, that ass…and especially that face. He could see why his uncle Luke was so in love with her. He'd had to walk away from her quickly, so she wouldn't see the massive bulge that was growing in his crotch. Of course, he always had a massive boner when he was around either of them. Even though he and Rory had been going out for over a month, she still wouldn't let him touch her. Once or twice she'd let him feel her perfect little titties, but her pussy was strictly off limits. And she'd never even come close to touching his dick. But Jess was content to wait. When you had a piece of ass that sweet, you waited as long as you had to.

"Hey, honey. You been waiting long?," Rory asked him as she walked into the room.

"Um…no, not really," he muttered as he stared at her in shock. She was wearing her Chilton uniform, which she knew always drove him wild, but there was something different about it today. The skirt, which usually went down to the knees, had been cut so that it barely covered her sweet little ass. And her shirt was only halfway buttoned, so that her firm perky cleavage was clearly visible. She obviously wasn't wearing a bra, as her tiny nipples poked through the thin fabric and were visible even from across the room. As she bounded over to the couch her skirt flopped around, leaving her amazing hairless pussy clearly in view. Jess nearly came in his pants, as he stared in amazement at her beautiful little cunt.

She sat down next to him and kissed his cheek, which was her usual greeting for him.

"Um…you look really nice tonight," he stammered.

"Oh, you're so sweet. You look really nice too. So nice, in fact…so nice I could eat you right up." She looked at him and smiled, then ran her hands over his strong chest. She nuzzled against him, then bent over and started to unzip his pants.

"Wha…what the hell are you doing? Your mother's in the next room."

"Oh, I don't think she'll mind," Rory giggled. "Besides, do you want this or don't you?"

"Well, you know that I do…"

"Then shut up and enjoy it."

Jess couldn't argue with that logic. He put his head back and closed his eyes, as Rory unzipped his pants and then pulled them completely off. She then pulled off his boxers, leaving him only wearing an old Clash t-shirt. His cock sprang up and hit Rory in the face, as she moaned softly and put her hand around it.

"God, I've wanted this for so long," she said as she lowered her face over it. She wrapped her lips around Jess' cock, then proceeded to take as much of it into her little mouth as she could. This was the first dick she'd ever seen or touched, and she absolutely loved it. She sucked at it enthusiastically, quickly developing a nice rhythm.

Jess sat there in absolute heaven. Although he'd dreamed for months about how Rory's gorgeous mouth would feel around his hard cock, he'd had no idea it could be this good. He groaned in pleasure, as she sucked him relentlessly.

"That's it, honey. You're doing great," he heard a voice say. Opening his eyes, he was shocked to see Lorelai standing above them and watching, with a big smile on her face. "Use your hands a little more," Lorelai instructed. "Play with his balls and jerk him off while you're sucking him. Guys like that."

Rory followed her instructions dutifully, making the best blowjob of Jess' life even better. Jess didn't know what the hell was going on, but he didn't really care. He knew Lorelai hated him and didn't want him around her daughter, but she didn't seem to mind at the moment. Besides, he was too close to cumming to think about much of anything right then.

"Oh God, I'm gonna cum. I'm gonna fucking cum, Rory!"

Rory sucked him even harder and squeezed his balls, causing Jess to pump load after load of cum into her virgin mouth. She swallowed as much as she could, then pulled back and let the rest of it land on her face, just like Lorelai had taught her.

"Good job, honey!" Lorelai told her. "If you can't swallow it all, then just take the rest on her face. Guys love to cum in girls' faces, don't they?," she asked, looking down at Jess. Since Lorelai knew that Rory was going to be having sex, she thought that the least she could do was teach her to do it right. Lorelai loved sex and knew how fantastic it could be, and she wanted Rory to as well. Rory was her darling little girl and they shared everything with each other…everything.

"Uh…that's right."

"Now come here, honey."

Rory hopped off the couch and went over to Lorelai. Lorelai kissed her softly, then proceeded to lick all of Jess' cum off of her face. She unbuttoned Rory's shirt and pulled it off, then pulled off her tiny skirt as well. "Okay, honey. Lie down now and spread your legs." Rory obediently lay down on the floor and spread her legs, as Jess stared at her lustfully. Although he had just cum, he was 18 years old and was still rock hard, as Lorelai knew that he would be.

"Well, what are you waiting for?" Lorelai asked him.

That was all the invitation he needed, as he scrambled off the couch and practically leapt onto the waiting Rory. She giggled sweetly, as they held each other and kissed. Although she was a virgin, he certainly wasn't. He ran his hands between her legs and found her clit, then stroked it expertly. She started to yelp and moan, as he continued to fondle her hard little clit.

"That's great, kids" Lorelai encouraged. She was impressed with Jess. For a teenage boy, he really seemed to know what he was doing. He didn't just dive between Rory's legs and start to pound her, like many boys would have. Rory groaned and squealed, as the first orgasm washed over her. Although it wasn't as intense as the ones given her by Lorelai, it was still incredibly good.

"Okay, I think it's time now," Lorelai said. "Jess, you lie on your back. Rory, you get on top of him." The kids did as they were told, as Rory excitedly slid her tight cunt over Jess' thick cock. "OH JESUS!" she screamed. This was much better than any dildo ever could be. She bounced up and down feverishly, as he fucked the tightest cunt in all of Star's Hollow.

"Okay, you're doing pretty good, Jess" he heard Lorelai say. "But if you want to go out with my daughter, you're gonna have to know how to eat a pussy. Now let's see what you've got."

He opened his eyes to see the now completely naked Lorelai, as she got on her knees and then lowered her sopping cunt onto his eager face. He attacked her clit furiously, while reaching around and inserting two of his fingers into her tight asshole. "Oh fuck!" Lorelai groaned. As much as she hated to admit it, this kid sure knew how to eat a cunt. He continued to pound into Rory, who was almost going insane from the pleasure of her first real cock. She had already cum three times and was closing in on a fourth, as he finally shot his load into her. She fell off of him and lay on the floor delighted and exhausted, as she watched him eat her mother's pussy.

Although Lorelai had already cum a number of times herself, she showed no signs of wanting to dismount the young man. She stayed with her thighs wrapped around his head and her hands running all over her delightful naked body, as he sucked and nibbled on her hard clit. She thrashed and moaned like a rabid animal as yet another orgasm engulfed her, then finally pulled herself off of him. Yeah, he was good enough for Rory. He'd definitely passed the test.

She crawled over to Rory, who was still lying motionless on the floor. She placed Rory's head in her lap and kissed the top of her head. "Well, how was it?" she asked her, as she stroked her hair gently. "Oh, Mom," Rory said. "I love you so much…"

Rabbit77
Rabbit77
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AnonymousAnonymous8 months ago

Absolutely fucking fabulous, just the way I like it. I absolutely adore Cunt in every way possible, especially when I am eating one while fucking another and sometimes fingering a third. I never get enough, the more I get the more I want. Fucking my brains out with multiple women until we all pass out from the insane levels of sexual pleasure we generate. Ready to start over as soon as we recover. Cunt crazed fucker, Lancashire, UK.

AnonymousAnonymousabout 15 years ago
shorty

its great but quite short lol!!!

AnonymousAnonymousover 17 years ago
i hope see more gilmore girls and men too

i love it and i love to see a complete set of those

AnonymousAnonymousover 18 years ago
Part 3??

Very hot... is there gonna be a part 3?

AnonymousAnonymousover 19 years ago
Hot!!!

The only reason I watch "The Gilmore Girls" is to fantasize about fucking Rory and Lorelai at the same time. I am glad to know that there is some one else out there like me. Keep the stories cumming. They are really good.

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