tagCelebrities & Fan FictionGilmore Girls: Fantasies of Lorelai

Gilmore Girls: Fantasies of Lorelai


Lorelai heard a tapping on a window. She looked up from her meager meal and searched for the source of the noise. It seemed to be coming from Rory's room. Lorelai got up to investigate. She peered into Rory's dark room past her daughter's bed towards the window. She saw a face nervously fogging up the window and then the tapping continued. Dean was standing outside probably hoping to talk to Rory, but since the fiasco after Rory's dance Lorelai wasn't about to let him go with giving him the business. Again she was going to have to remind him of his promise not to harm Rory (or her reputation).

She flicked on the light and walked towards the window. Dean's eyes quickly adjusted and he realized that he had unwittingly gotten Lorelai's attention instead of her daughter's. He involutary twitched when the shade shot up in front of the window. Lorelai unlocked the window and slid it open. She leaned down to meet Dean's gaze. "Well hi there," Lorelai quickly said.

"Hi...," Dean said while he inwardly grimaced knowing that he was in trouble.

"How you doin'?"

"Fine," Dean let out.

"Good. Shouldn't you have a squeegee with you?"

"I was just..." Lorelai cut in, "Looking for Rory? She's not here."

"Okay," Dean said.

"I'll tell her you tapped."

"Thanks," was the only thing Dean could think to say at the moment. Lorelai moved to close the window, but Dean just stayed there. She leaned back down.

"Something else?," she inquired.

"I just...I wanted to say that things got all messed up," Dean explained.

"Yes, they did," Lorelai quickly agreed.

"And I'm sorry," Dean said.

"Uh-huh," Lorelai retorted disbelievingly.

"But nothing happened," Dean stated earnestly.

"Okay, I have to go."

"We sat down, and we were reading this book and then we fell asleep," he further explained.

"Pick a more interesting book next time," Lorelai almost spat out. She crossed her arms and sighed. She did believe that Rory and Dean hadn't had sex and that he was a gentleman, but she wasn't willing to fully give up this grudge just yet.

"So am I public enemy number one with you?," Dean asked.

"Number one? I don't know," Lorelai thought about her present situation with her mother and how they were yet again not-on-speaking terms. "Would you settle for top five? I still a little hot for that crazy, bomber guy who's been living in a cave for a year."

"Please just tell me where I stand," Dean pleaded.

"I don't know where you stand, okay? All I know is my sixteen-year-old didn't come home one night, and you had something to do with that," Lorelai said letting how upset she felt pour into her words.

"I told you, nothing happened," said Dean.

"I heard," again Lorelai's tone sounded rather disbelieving.

"You can hate me, but you have to believe me," Dean responded. "I would not let anything happen to her."

"You happened to her," Lorelai interjected.

"I won't hurt her," Dean further stated.

"You know, I was sixteen when I had Rory," Lorelai's words gave away her fear.

"I know," Dean said adamantly. He wished he could just convince her that wasn't going to happen with Rory.

"That is the same age she is now."

"I know," Dean repeated this time softer.

"She wants to go to Harvard."

"She will go to Harvard, and if she doesn't, it won't be because of me," Dean reassured Lorelai. Dean sighed. He felt this argument was becoming futile. He stood up from his crouching position and was about to walk away when he heard, "I don't hate you."


"No, though I did imagine abut twenty different ways to remove your head from your body," Lorelai confessed.

"Yeah, which one looked best?"

"Hedge clippers. Dull ones," Lorelai said letting a smile play across her face.

"Sure," Dean agreed, "you wouldn't want it to go quick."

"Exactly," she said. Lorelai felt her resolve to hold this grudge against Dean soften a great deal. He crouched there for a second thinking that perhaps there was hope that this relationship could be saved.

"Okay, I'm going to go," Dean said. He had been cold this entire time.

"Dean, We have a really nice front door. You might want to use sometimes."

"Got it," he said.

"Dean?,"Lorelai asked, "Are you cold?"

"Freezing," Dean admitted.

"You know you can come in and warm up for a minute."

Dean was happy to accept the offer, after all his assets were frozen. He walked to the front door while Lorelai closed Rory's window. He stood there a moment until he heard the door unlatch and Lorelai welcomed him in. They stood there a minute Dean letting his feet warm up and flexing his fingers to allow the blood to circulate more freely.

"Would you like some coffee," Lorelai offered.

"Yes. Thank you," Dean eagerly accepted. He was desperate for some warmth.

Lorelai led him to the kitchen and pulled a mug from out of the cabinet. She poured some coffee in the mug. She turned to give the coffee to Dean, but rather than handing it to him, she tripped and ended up spilling hot coffee on him. Dean gasped, that coffee was hot, hot, HOT!! And she had spilled it right on his crotch.

Lorelai quickly grabbed a dish towel and tried to dry his pants. She couldn't believe she had done that. She was flustered. Dean could help but say, "Ow, ow, ow..." She dabbed away at Dean's pants and felt something rather long grow. Dean froze. He looked horrified at the noticeable bulge in his pants growing.

Lorelai stood up and stared at Dean. Dean nervously stared back and was half expecting Lorelai to make up an excuse to escape from this awkward situation. But rather than an excuse Lorelai drying become slower. She dabbed the dish towel along the length of Dean's now semi erect penis. Dean stared back at Lorelai still horrified that he had lost control of his body. However, luckily for Dean Lorelai's thoughts were more in awe of the size of Dean's package. She continued to dab and then decided to drop the ruse altogether and dropped the towel and felt Dean's growing erection.

Lorelai couldn't believe she was being so bold, so forward. Dean opened his mouth to say something, but nothing came out. He had never thought of Lorelai in a sexual manner, but at this moment he felt an overwhelming urge to tear her clothes off. Lorelai looked into Dean's eyes. The feeling of lust it looked like was mutual.

Lorelai slid her hand behind Dean's neck and pulled her lips towards his. Dean slowly kissed her back and leaned back against the counter. Lorelai's body pressed against his chest and she wrapped her arms around his neck. Their eyes closed and let each other's tongues enter the others mouth. Their breathing became deep and heavy. Dean leaned forward as Lorelai lead him torwards her bedroom. Lorelai couldn't believe she was doing this. I mean Dean was her daughter's boyfriend! But, she felt a pulsing need in between her legs. The size of Dean's package if she was correct was going to be epic and worth unveiling. Dean followed her entranced.

She started walking up the stairs, but stopped when she felt Dean's hands wrap around her and cup her breasts. She loved the feeling of Dean's subtle massage. Her hand came down and rubbed Dean's package. Dean felt the need to reciprocate, so he let his hands slide down Lorelai's chest under her waistband, into her panties and finger her moist clit. "Oh boy," Lorelai thought. She hadn't been touched in this manner in the longest time.

She let the out her breathe quickly as she felt Dean's pelvis meet her backside. Dean felt his own erection slide up between Lorelai's butt cheeks. Even with all the material in between Dean could feel Lorelai's taut butt. He let one hand unbutton the top of Lorelai's jeans as the other slid onto her warm skin down underneath her underwear. Dean was inexperienced in love making or knowing a woman's body, but countless research sessions on the internet had made him an expert at locating a woman's clitoris.

Admittedly Dean had done the research in fears that he would disappoint Rory the first time they ever decided to have sex. Now he was using that information for Rory's dark haired beauty of a mother. The irony was lost to Dean as he found the small nub he had been looking for and rubbed it with the rough calluses of his hand.

The sensation of the ridges of Dean's hand rubbing against her clit made Lorelai shiver. She loved that sensation that caused electric bursts of pleasure explode in her brain. Dean's right hand rubbed Lorelai's breasts over her shirt. Lorelai reached her left hand over her shoulder and placed it on Dean's neck. She pulled his head forwards and turned her head to kiss him. Lorelai's tongue snaked into Dean's mouth. "MMMMMmmmmmm," she hummed as her nipples hardened against the insides of her bra.

She felt Dean's attentions return to her clit as both of his hands found their way underneath her panties. She broke away from Dean's face as she felt Dean's long fingers enter into her. Dean had found his way inside her. Dean had never done this before and was surprised at how much moisture there was inside of Lorelai. Lorelai stared unbelieving at the hands in her pants. One hand rubbing her clit the other rubbing her insides. Perhaps it was the taboo of the situation or the fact that Lorelai hadn't had sex in awhile or the fact that Dean was showing a natural aptitude for pleasing her body but Lorelai was feeling so turned on.

Both of her hands reached behind he and latched onto Dean's butt forcing Dean's large erection to further dig into her backside. She couldn't believe that her daughter's boyfriend was doing this to her. She couldn't believe that she was allowing this to happen. Those thoughts disappeared as Dean's ministrations intensified and Lorelai felt something climatic building inside her. Dean felt Lorelai's insides quiver as she let out a loud moan.

Lorelai then commanded Dean, "Make me cum". She repeated it as Dean endeavored to meet her demands. "Make me cum. Oh yes, make me cum." It sounded less like a command now and more like begging as Lorelai's pitch went higher. "Make me cum, oh make me cum, make me cummmmmmmm...," she pleaded. Lorelai felt the her pleasure starting to spike. She moaned loudly. "Yes that's it. Rub me like that. Oh don't stop, don't stop, don't stop, make me cuuuuuummmMMMMMMMM!!"

Lorelai took in a deep breath and let out a scream. Dean felt his hand and Lorelai's panties suddenly engulfed in fluids. Yet he continued to massage Lorelai's clit and insides. Lorelai felt her legs shake as tons of wetness made its way out of her. She fell forward on the stairs. She was barely able to remove her nails from Dean's butt cheeks in time to catch herself from hitting the floor.

Dean stood there over Lorelai looking proudly at his wet hands. Lorelai stayed kneeling on the stairs with her eyes closed savoring the heights of her recent orgasm. Dean looked nervously at Lorelai. He didn't know what could be possibly going on in her head. What was going on in his head? What had he done? He thought of what Rory would do if she were to discover this new development in her mother's and her boyfriend's relationship.

Lorelai stood and turned around. She smiled at Dean. "Dean, that was the best, perhaps there is something I can show you up in my room."

She took Dean's hand and lead him up the remaining steps to her bedroom. Dean looked around and studied the room. The dresser in the corner, the clothes strewn about almost in some sort of organized chaos. He continued to study the room when he felt Lorelai's hands push into chest and let him fall onto her bed. Lorelai jumped on top of Dean her legs planted on either side of his hips. She slipped her hands under his shirt and felt Dean's teen body. Oh my he was built.

She pulled his shirt over his head almost in a comical fashion wrestling with the fabric as it got caught on Dean's chin. She bent forward as Dean's shirt was thrown to the other side of the room. She placed her lips on his and her hands on his pecs. She slid her kisses over to Dean's neck and down his torso. She her body down Dean's legs and paused at his belly button. Lorelai had been very curious to see the extent that Dean was endowed.

She undid Dean's belt as she bit her lip. Dean arched his butt in the air as he felt Lorelai unzip his jeans. She reached under the waistbands of both his jeans and underwear and pulled down viciously. Lorelai felt something wack in the face. "Holy shit," she murmured as she found what had hit her between the eyes.

The sight which Lorelai beheld was for lack of a better word, beautiful. It looked to be a 10 inch long cock. It was really thick at the base with gorgeous veins up the shaft that led to the giant purple helmet. Her hand reached out and took a grip at the base. No her hand couldn't even fully wrap around Dean's large penis.

"Wow," she thought to herself, "this thing might split me half". Lorelai trying to make a fist let her hand slide up the length of Dean's shaft. Dean shuddered with pleasure. His member was on fire with pleasure and twitched with anticipation of what he knew was to come.

Lorelai had dated many men and knew how exactly to please them. But she had never tackled anything of this magnitude before. She looked at Dean's quivering penis. This would be her sexual Everest. Dean craned his neck over the profile of his own body to see what Lorelai was doing. Lorelai's eyes shifted from Dean's penis to his eyes. Dean's penis unconsciously twitched again as he studied Lorelai's lustful eyes. Lorelai grabbed the hem of her shirt with both hands and lifted the material off her body in one smooth motion.

She watched Dean's penis twitch again as Dean finally got to see Lorelai's generous C cup sized breasts tightly clasped by her bra. Much bigger than Rory's breasts. Lorelai reached behind her back and undid the latch of her bra letting it drop to the floor which caused Dean's mouth to also drop to the floor.

There she was, Lorelai, half naked her perky, youthful tits right before Dean's eyes. He couldn't believe that this was happening. He studied her nipples. Both were slightly puffy and the centers hard and pointing straight out. He was about to reach forward and squeeze those wonderful looking nipples when Lorelai licked her tongue across the top of Dean's penis.

She licked from where the skin of his scrotum met his shaft straight up the underside and reaching Dean's mushroom tip. Dean quivered and his fists clenched Lorelai's sheets tightly. No woman had ever given his penis these kind of attentions before. Lorelai wrapped her mouth around the tip of Dean's penis and sucked up the precum off of his slit. Dean then felt his glans being repeatedly licked with Lorelai's tongue. Lorelai was doing it so forcefully that a momentarily lapse of bloodflow occurred to the head of Dean's penis which Dean could only describe as, "heavenly."

Lorelai removed Dean's penis from her mouth. She spat on one of her palms and started rubbing her saliva up and down Dean's shaft. Her other hand tweaked her own nipples for a moment before finding its way in between her legs.

Lorelai studied the large cock before her. She had always been a fan of erotic asphyxiation and she had found the perfect tool to gag herself with. She replaced her mouth on Dean's penis slowly forcing the shaft into her mouth. She made it halfway down Dean's shaft before her gag reflex kicked in. She bobbed up on his cock. Lorelai breathed heavily as a long chain of saliva fell from her mouth onto Dean's penis. Again she inserted Dean's penis into her mouth. Down she went to the halfway point her hand jerking the remaining five inches.

She fought her gag reflex and pushed down three more inches. She let his cock stay down her throat for a few seconds before she started to see stars. She bobbed up again this time taking even deeper breathes her breasts heaving almost uncontrollably. She continued to assault Dean's penis this way until after a eighth time she bobbed off his penis she felt another orgasm hit her. Waves of erotic pleasure hit her as she continued to finger herself.

Dean loved watching the spectacle. He leaned forward and pinched Lorelai's nipples. She screamed as the last climatic wave of her orgasm washed over her. Lorelai looked like an animal in heat. She pushed Dean back onto the bed and both of her hands and her mouth started to work Dean's cock. She bobbed up and down on his meat as her her hands jerked upwards twisting upon the length that they traveled. Dean gritted his teeth. Watching this was making him want to cum.

He closed his eyes concentrating on the sensation of Lorelai's mouth milking his penis. He began to groan as his climax grew. Lorelai removed her mouth from the equation jerking and twisting Dean's pole with both of her hands. Dean's eyes shot open. Lorelai's mouth was open and her eyes looked as though she was pleading. "I'm going to...I'm going to...," Dean was unable to finish his thought the pleasure being too much for him to even formulate words.

Lorelai simply nodded her head yes and said, "I know. I want you to cum. I want to see you cum." She cooed after she said this and watched as Dean's mushroom tip pulsed.

Dean suddenly let out a grunt. "Lorelai, I'm going to...I'm going to...I'm going to cum."

As Dean said cum a huge strand of semen shot up into the air. Another followed splashing Lorelai's shocked face. She quickly drew her mouth to his penis to stem the tide of mess caused by Dean cumming. Lorelai's mouth was instantly filled with Dean's seed so much so that it started to dribble out of the corners of her mouth. Lorelai swallowed to make room for more as she noted his sweetly tasting cum. Almost citrus flavored. Lorelai swallowed the mouthful of cum she had and slurped up the remaining cum leaking out of the top of Dean's penis.

Dean looked nervously at Lorelai as his dick started to soften. Lorelai looked disappointedly at Dean's dimming erection. There was so much more that she desired to do to Dean. "What the hell Dean," she said, "you are not going to stay hard for me." Dean looked away from Lorelai's accusing eyes. "No matter," she said, "I'm not done with you."

Lorelai slipped off her jeans and stepped out of them. She crawled over Dean's body stopping to kiss Dean's lips and then continued crawling until her panties were hovering right before Dean's eyes. Dean's eyes looked questioningly at Lorelai. "Lorelai, what-" he said before he was cut off by Lorelai rubbing her sex against Dean's face.

Her panties still bore the juices of Lorelai's climax and there was a certain musk that filled Dean's nostrils. Dean reached around Lorelai's legs and squeezed her buttocks pulling the source of the musk closer to his nose. He inhaled deeply her scent and licked Lorelai's panties. Lorelai looked down between her legs as she felt Dean's tongue lapping on the outside of her panties. She pulled aside the crotch of her panties to allow Dean's tongue to find access to her clit. Dean studied the new view in front of him.

He had never seen any women's labia and studied the beautiful pink petals of Lorelai's labia before him. He licked upwards on Lorelai's mound tasting the sweetness of her wetness. He found the nub of Lorelai's clitoris that he had found earlier and licked it for all its worth. Lorelai closed her eyes leaned her head back and started to unconsciously let her hips move back and forth, slowly humping Dean's face.

Dean's tongue and hot breathe found its way inside Lorelai causing Lorelai to hump Dean's face more urgently. Her Lorelai felt the level of her lust spiking she leaned her head back and let out a climatic scream. Lorelai reached down with one hand and pulled from the back of Dean's head forcing his face further into her sex. A new gush of fluids filled Dean's mouth as Lorelai's orgasm washed over her.

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