The characters from the Gilmore Girls are the property of Amy Sherman/Warner Bros. I'm just borrowing them.

Gilmore Girls: Prostituting Rory (Ff,inc,anal)
by LL

Things didn't change at chez Gilmore, Lorelai thought, everything seemed the same as when she'd last been here, two years ago for the funeral of her father, and even then it didn't look like it changed since she visited the time before that. She wracked her brains when - was it Rory's twelfth or had they visited sometime after that? She thought they might have stopped once on the way back from New York city, when it was late and she had an excuse not to stay long, but was that before or after Rory's birthday? She couldn't remember, which was another sign of the stultifying samesness of her mother's house; if you dropped the her back when she was pregnant, and just about to leave, she'd not have noticed any difference in the next sixteen years.

Her mother hadn't changed much either, her hair might have had a few more grey hairs, but even those were concealed by the red dye in a perfectly sculptured coiffure. Her face might have been attractive, but it remained stern and dominant, like Lorelai was a perpetual disappointment. As Lorelai was sure, that to her mother at least, she was, she hadn't bothered to announce she was coming, just turning up in her 4x4 and ringing at the doorbell. If the maid who answered the door was surprised that someone claiming to be her employer's daughter had turned up she hadn't shown it, but then Emily's help was hired as much for their discretion as any other skill. On coming into the second lounge, where Lorelai had been placed, her Mother had shown no surprise either, despite not having seen Lorelai for two years. That was the famous Emily Gilmore poise - the world could be about to be hit by a giant asteroid and Emily would keep her reactions within the boundaries of decorum.

"Tea?" Emily asked.

Lorelai would have preferred coffee, but that wasn't on offer and she knew better than to ask, not when she was here to ask a favour from her mother, or perhaps make her an offer would be a better description. She nodded, "Yes," instantly adding, "please." The extra word cost nothing.

"For two," Emily said to the maid who was now standing behind her. She didn't add the word, politeness might be free, but it wasn't for the hired help.

The woman left and Emily sat down on the couch, a respectable distance from her daughter. "How have you been?" she asked politely.

"I'm doing well. Works great, relationships great as well, I've been seeing this woman for the last eighteen months, it's going well."

Did her Mom's lip quirk a little? Lorelai wasn't sure. She didn't think that Emily was jealous, it had been sixteen years since they'd been lovers, her Mother making regular love to her whilst her gay Father was entertaining his latest beau in the main bedroom. Even so she blushed a little.

"That's nice to hear," Emily said. If she noticed Lorelai didn't say anything about Rory she didn't mention it. "You must bring her round to dinner."

That still didn't answer whether her Mother felt anything; you didn't invite your ex-lover's current squeeze unless you were over them, however, given the number of times Lorelai came over, her Mother must have suspected that the chance of her being taken up on the offer was close to zero. Despite that Lorelai nodded politely back replied, "That would be lovely," in a non-committal tone. She quickly changed the subject, "How are you?"

She wasn't expecting any personal insights and didn't get any, the reply said more about her Mother's geraniums than it did her life. Still it filled in the conversation until the maid knocked on the door and brought in the tea, placing it on a sideboard. Emily gestured to the woman to take it over to the table, before dismissing her.

The door shut and Emily got up to pour the tea. Lorelai wondered if her Mother had read things wrong and thought Lorelai was here to rekindle the relationship. Ten years ago that would have been a risk, Lorelai hadn't left home because she disliked being her Mother's sextoy, even sixteen years later she could remember the pleasure as her Mom pounded her ass. So much had she enjoyed it that not until she'd been with her current girlfriend almost a year did she let her into the hole which she still regarded as Emily's. No, she'd left because even as a teen she realised that she also wanted to be independent, to get that she needed to leave home and to leave home she had to become pregnant. She didn't regret any of it, but her pussy still quivered a little when she remembered.

"Milk?" her mother asked.

"A little," replied Lorelai. Emily poured the tea and then added the milk as she always did. She brought the two cups and saucers over and placed them on the coffee table in front of Lorelai. She sat down and waited.

Lorelai took a small sip, she didn't think much of tea as hot drinks went, but this was just about drinkable. She also realised she was using it to stall for time. She took a mental deep breath. "Rory's doing well, she's just passed the entrance exam for Chilton."

Was there a faint touch of a smile at Emily's lips. A told you so that Rory was following in the footsteps of privilege that Lorelai had told everyone she'd eschewed. "She always was a very bright child."

"She's sixteen now, a young woman," replied Lorelai. She paused before saying the next words, even though she'd talked it through at length with Rory and the teen agreed that what they were going to do was for the best. "I've some photos if you want to see them."

Her mother nodded politely, though Lorelai suspected she was more excited than she looked at seeing her granddaughter. Lorelai reached into her bag and pulled out the glossy prints, hoping that seeing them would make her mother more excited still. Looking down at the first she was sure it would. She slid the first photo across the coffee table towards Emily. The photo was off Rory in the shower, the door open so that you could see her naked behind, soap trickling down it. It got a reaction, even if it was only a slight widening of the eyes. "She's turning out to be very attractive, don't you think?"

She didn't give her Mother time to answer before she passed across the second photo. It was from the same time as the one before, but in the previous one Rory had been facing the wall and it was possible she'd had it taken unaware, this one had been taken to show she was. The teen was looking over her shoulder a smile on her face, that was both welcoming, sexy, wicked and innocent. It had taken them a long time to get the right expression, giggling all the time as Rory pulled expression after expression, many of them comical until they'd got to the right one. "I might be biased, but I think her smile lights up the room," Lorelai tried to keep her voice neutral.

She glanced at her Mother. Emily wasn't looking at her, but down at the photographs of her granddaugher, her teacup held partly towards her mouth, but not being sipped as if Emily had better things to do. Lorelai pulled out the third photo, still from the same set, except this time Rory was out from shower and standing with a towel wrapped round her waist, her hands over her tits fingers splayed so that you could just, if you looked closely, see the nipple between them. "She's growing up so fast."

"As you can see from the next picture," Lorelai continued as slid the fourth photo across the table. In it Rory was facing a full-length mirror, she was wearing a pair of jeans and nothing else, an outstretched hand holding a black bra she'd just removed. Her wonderfully perky tits were more than adequately reflected and Lorelai took a quick glimpse at her Mother. Emily was looking at them, and as far as she had an expression it was entranced. The plan was working so far and Lorelai continued with her perfectly planned spiel.

"She's very studious," Lorelai slipped the next picture towards her Mom. It was a photo of Rory, taken from behind and to the side, doing her homework at the kitchen table. She was bent over totally concentrating on exercise book she was writing in, a tongue stuck endearingly out of her mouth as she thought. It could have been any family snap taken by a proud Mom of her bright, clever daughter as she prepared for her entrance exams to a prestigious school. Except for the fact the teen was bare-assed naked without a stitch on.

"This one is better," Lorelai peeled the next snap from the bundle and placed it in front of her Mom. Rory was still studying, except this time she was sitting on the sofa a book in front of her, posed so she was holding it up. Unlike before she was this time wearing a top, but without anything underneath, her legs just open enough to show a glimpse of her shaven slit.

Lorelai didn't give her Mom anytime to admire the pussy, instead adding the next photo onto the rapidly growing pile in front of her Mom. "She always likes to read before she goes to bed." A naked Rory lay face down on her bed, reading intently and not caring that she was being photographed with her butt in the buff.

"Not that she always works," the next photo was off Rory sitting on a bench dress in the middle of Stars Hollow, in the background several of the small town's citizens walked the sidewalk ignoring the teen. What none of them could see was that Rory had lifted the front of her dress and spread her legs so that the photographing Lorelai could get a shot of uncovered pussy.

"She likes to watch TV whilst eating pizza," said Lorelai, showing her Mother a photo to confirm that, a naked Rory lying on her front on the sofa, whilst lifting a piece of pizza.

"And she has ways to relax as well," Lorelai said. The picture she slid across was off Rory in a her pyjamas sitting on her bed, she was sucking a dildo like it was a popsicle and using her other hand to undo the lace round the top of her bottoms. Lorelai looked again at her Mother, the older woman fascinated by her granddaughter. There was one more photo...

She slid it across the table towards her Mom, "I'm very proud of the woman she's become," the brunette smiled. The final photo was off Rory lying on her side on her bed, as naked as nature intended. Her elbow rested on the bed and her hand was lifting her head was giving the camera a winning smile whilst her upper leg was up at a right angle pointing at the ceiling giving the best view yet of her teenage pussy, a dildo jammed in the tight hole.

Sitting back Lorelai let her Mom continue to look at the pictures for a moment before saying, "You can keep those ones if you like."

"Thank you Lorelai," her Mom gave the smallest trace of a smile as she gathered them up. "I might have some framed." It was an indication that she had liked what she'd seen and so she should, Lorelai was hot and Rory was her daughter. She raised her tea cup and sipped it delicately. Then she put it down and fixed her daughter with a gaze like steel, "We could play games all afternoon Lorelai, why don't you just say what you want?"

"I want you to pay Rory's Chilton fees, the scholarship only covers half of it," Lorelai said.

"And what you send me some pictures of her on graduation, perhaps lifting her skirt towards the camera?" her Mother asked.

"Rory's a virgin, what about first use of that sweet hole you've been admiring?" said Lorelai.

Her Mom inclined her head gently, "I was admiring more than one."

"Holes..." Lorelai said, nodding. She'd agreed the negotiations with Rory beforehand to make sure she wouldn't offer more than Rory would agree to. Her daughter, however, put a high premium on a quality education.

There was a further pause from Emily, "Chilton is an expensive school and Rory's got three years there before College. Harvard? Yale?"

"Probably Harvard," Lorelai said.

"Chilton would be a good start, I'm sure its the alma mater of a number of Harvard professors," Emily said, "But that is costly."

Lorelai went to the next stage, "What about that Rory comes to you every Friday during term? She's yours until Saturday after breakfast."

"Make it noon, I remember you as a teen, breakfast was optional," Emily said.

"Okay, for that you pay her fees, books and uniform and she gets a car on graduation," Lorelai said.

"A car? Why not? If she gets the grades..." Emily said.

"Straight A's," replied Lorelai, confident her daughter could get that, "She'll need money for school trips and extra-curricular activities as well..."

"Which we'll negotiate on a case by case basis," Emily replied and Lorelai nodded. The older woman raised her cup again and sipped her tea, "One more thing.... I want exclusivity. Rory's mine until she graduates, no other women or men or boys even, unless I say so."

"We can agree to that," Lorelai said, knowing how important Rory thought Chilton was.

"I'll write a check," Emily replied.

* * *

The first week at a new school was always nerve wracking; doubly so if it was a school as prestigious as Chilton and you were the daughter of a single Mom hotel manager. Still Rory was pleased at how easily she'd settled, not that she'd made any friends, but then she wasn't there to become Miss Popularity but to settle down and get good grades. And the education was as good as promised, the teachers both demanding and encouraging. The was school library the biggest she'd seen and stocked with the latest editions of seminal works, not those which had been cutting age during the sixties. And the homework was actually challenging, forcing her to think and not rattle off an answer in thirty seconds before settling in front of the TV with a pizza.

Still as she got off the bus on her first Friday she was as nervous as she'd been at the start of the week, admittedly for a different reason. It had seemed such a good idea when she and her Mom had spoken about it, all Rory had to do was give up her holes to her horny, lesbian grandmother in return for a great education. But now that the time was approaching the trepidation was growing; what if she didn't like it? what if her grandmother didn't like it? what if...? what if...? what if...?

She forced aside her fears as she entered the restroom of the small mall a few blocks from her Grandmothers. It was time to make some changes to her uniform. Stepping into the cubicle she removed her blouse and bra, placing the bra into her little rucksack before slipping the blouse back on, but leaving more buttons open that would have been considered acceptable during the day. Next off came her panties and into her rucksack, she didn't replace them, but did slip on a pair of sexy stockings up her legs. They were little things but they made her feel more sexy and ready. Taking a deep breath she left the restroom, ignoring the appreciative glances and got the second bus that would drop her off near her grandmother's.

The doorbell's sound was deep and sonorous, more like it should have been on top of a church tower rather than a door, no matter how imposing the house. Perhaps it needed to be because the place was so big, certainly it was near to a minute before the front door opened and a middle aged woman in grey stood before her. If she was surprised to see a schoolgirl with too much cleavage on display she didn't show it, her face remaining impassive as she said, "Yes?"

"I'm Rory Gilmore. Emily Gilmore is my grandmother. I'm visiting her for dinner and to stay the night," Rory burbled, aware she could have probably stopped a quarter or at least a half into her sentence.

"Mrs Gilmore is waiting for you in the main room," the maid said and beckoned for Rory to follow her.

To the sixteen year old it seemed they entered a maze of passages for hours, but was only a couple of left turns and around ten seconds, before they stopped at the door which the maid opened and gestured for Rory to enter before her. The teen stepped into a room, which was probably as big as her entire house. Her grandmother got up up from a couch which must have cost more than most people spent on all their furniture. She stepped forward, "Rory," she smiled, "How lovely to see you again." She gently kissed the teen on each cheek with not the slightest sexual touch. She turned to the maid, the tone changing from friendliness to one used for addressing servants, "When will dinner be served?"

"Thirty minutes ma'am," the maid replied.

Emily didn't even bother dismissing her instead she turned to her granddaughter. "Good that will give me time to show you your room."

Rory was a little confused, she'd assumed she'd be sharing a room with her Grandmother. But she hid it well and nodded, "That would be nice."

Emily didn't take her straight there, first giving her a tour of the ground floor, which had half a dozen main rooms, plus two studies and the servants quarters (which they didn't enter). Emily then guided her granddaughter to the grander set of stairs and onto a landing that seemed longer than many streets. The older woman paused by one door, which she didn't open, "This is my room," she said. There was a sparkle to her smile which told Rory that she'd see a lot of this room over the Friday nights to come. The teen gave a smile back which she hoped wasn't too nervous. The older woman moved a little along the corridor to a room opposite. She pushed open the door and stepped in. Rory followed her.

It was much larger than her room at home, in fact the bathroom off to the side was probably bigger than her room. The furnishings, a massive wardrobe, a couple of comfy chairs, an oak desk and a book shelf filled with leather bound volumes were much, much more expensive than her cheap flat-pack furniture. "I hope you like it. I wasn't sure what books you'd like so I've got you some Shakespeare and Marlow, some Emily Dickinson as well as the History of the Peloponnesian Wars by Thucydides, in Greek with the English translation."

"They'll do, I'll read anything."

"Let me know what you want. I'll have them ordered. Reading is food for the mind," Emily smiled. She pointed at the wardrobe, "You'll want to change before dinner. There's a dress in there, I got the measuremets from your mother." She smiled, "I'll see you downstairs in ten minutes."

She left leaving Rory on her own. The teen wondered if she and her mom had got the wrong end of the stick; she doubted it, but her Grandmother hadn't made any move, despite Rory looking her schoolgirl sexiest. She opened the door and pulled out the dress. Putting on she decided that they'd definitely got the right end. The dress was a dark black, slinky and silky, tight with cuts down the legs so that her legs would show as she walked. That wasn't the only place it was cut away, there was a thin slip of material between the waist and her breasts, with her sides bare and the cleavage low cut. A final strip of cloth went up and tied round her neck leaving her back naked. She'd never worn anything so revealing and it made her both feel embarrassed and sexy. She glanced at the clock, a wooden box with gold inlaid numbers and quickly slipped into the high heels that had come with the dress; it was time for dinner.

Rory guiltily released she was a couple of minutes late. Her Grandmother was waiting for her in what she had called the second dining room. She too had changed and was wearing a sexy silver dress, which left plenty of cleavage exposed without showing everything. The older woman's eyes danced over the teen, "You look good in that dress," she smiled, gesturing to a seat.

"Thanks Grandma," said Rory as she sat. She gave Emily a dazzling smile, she wanted to give her Grandmother her money's worth, the fees were very expensive nor was the uniform cheap, "You look lovely in that dress as well."

"This old thing," tittered Emily, but you could see she was pleased at the compliment. She rang a bell on the table and almost immediately the door opened and the maid came in carrying a tray with two bowls of soup. "I'm afraid no pizza."

"That's alright," said Rory looking down at the thick green liquid placed in front of her and wondering what it was.

The dinner was uneventful, and if the food wasn't as tasty as pizza, it was still more than edible. They talked about lots of things as they ate, a little about school, but a lot about politics, history, literature even some philosophy, which Rory found fascinating, her Grandmother sipping some wine and Rory drinking her cola as they talked about Socrates and Plato. It was so interesting Rory almost forgot why she was here, though every now and then she caught a lascivious look in Emily's eyes as the teen moved in such a way that a touch more bosom was uncovered. After dinner they moved into one of the other rooms to take their coffee and continue with the conversation.

Still Emily made no move beyond undressing Rory with her eyes as she gave her views on the President's handling of the economy. After about an hour she smiled at her Granddaughter, "I think its time you went to bed, don't you?"

Here it was, thought Rory, it was early if she was going to sleep but as she wasn't it was much later than she expected as she'd expected to be deflowered virtually on walking into the house. She nodded and gave her most winning smile, "Yes."

"I'm not sure if you brought nightwear so I took the liberty of buying you some; its in the top drawer," Emily said.

Rory turned for the door. Her Grandmother was remaining seated. The teen turned back, a little confused but trying not to show it, "Aren't you coming up? To bed?"

Her Grandmother smiled, "I'm just going to have a brandy and reply to a few letters. I'll be going up shortly."

Rory nodded and left, so much said she was her Grandmother's whore, from the sexy dress to the way the old woman looked at her to what had been agreed with her own Mom, except her Grandmother wasn't making a move. Rory wondered whether she was shy and nervous, and dismissed the thoughts out of hand. Perhaps she was just having second thoughts about banging her own flesh and blood, except she'd banged Lorelai when she was younger (which was what had given Rory and Lorelai the idea). The teen mentally shrugged and went to the sideboard where Emily had said the nightie was. The mystery deepened as she pulled it out; it was not something a self-respecting Grandmother would get her teenage Granddaughter; so see-through it was almost invisible and whilst the straps held it up over her titties they only just did and it wasn't long enough to cover her pussy. Rory put it on, she had brought nightwear, but none as sexy as this and if Emily hadn't told her to wear it she'd certainly hinted to do so.

She quickly got washed and cleaned, before returning to the bedroom. She was unsure what to do. Was she expected to go to sleep? It was still early. Or call for her Grandmother to tuck her in? The older woman seemed like she was doing other things. Perhaps she was supposed to lie here seductively and wait? But if Emily didn't call she'd be there all night. Eventually Rory decided the best thing to do was leave on the side light and read some of the Emily Dickinson poetry.

She enjoyed her normally, but this time she couldn't concentrate. Every time she read a few lines they blurred and she'd find herself forgetting where she was and starting again.

For an old house, it must have been pretty well sound-proofed, as the first she knew that Emily had come upstairs was the knock on her door, "Rory, are you awake?"

"Yes," Rory called back, quickly putting the book onto the bed-stand and adjusting herself under the covers so that she looked as sexy as possible.

The door opened and Emily entered. She was wearing silk pyjamas and smiling brightly, but what Rory really noticed what was the huge lump sticking out from her pussy like a hard-on. Rory wasn't naive and she knew exactly what it was. Seeing its size the confusion vanished to be replaced by nerves; she managed a smile, but no words as her Grandmother approached.

She smiled, "I'm here to collect my payment, you know what that is?"

Rory nodded nervously, "You pay my fees and get to fuck me."

"Like a whore," her Grandmother smiled, "Just so we're clear I'm paying money for sex. You might be my Granddaughter, but when we're fucking you're just a prostitute, bought and hired."

"Yes, I understand. It's what I agreed to, I get an education and you get my hole."

"Holes, Rory," her Grandmother smiled wickedly, "I want my money's worth." She reached down and pulled back the covers, leaving Rory's pussy exposed to her gaze. She looked down lasciviously at it. "Lorelai sold you as a virgin, is that right?"

"Yes," Rory nodded nervously, "I mean I've used a toy on myself, but I've never had anyone else in there."

"They say you always remember your first time and your memories will be whoring it out for your Grandmother," Emily grinned. She reached for her pyjama bottoms and pulled them down enough that the dildo popped out the top. Uncovered it seemed even bigger, ten inches of plastic prick complete with a head like a mushroom and hard ridges which almost looked like veins. "As I fuck you I want you to be enthusiastic, not lying there like a damp cloth, I want to hear you screaming for more, yelling for it harder, fucking me back. Am I clear?"

"Yes Grandmother," Rory said and looked down at the huge dick, it was almost impossible to comprehend that in a few moments that would be in her, it seemed so big.

The older woman got on the bed, pushing Rory back with one hand whilst the other reached down for the teen's crotch. She slid a finger over the slit, "That is so hot, I'm going to love fucking that whore-hole." She continued down, pushing her hands between the thighs and easing them apart. Rory followed through, opening her legs for her Grandmother and reaching down to her cunt to spread it open between her fingers.

Her Grandmother moved on top of her, expertly guiding the toy to Rory's twat. The teen found that she was already wet, her pussy excited even if the rest of her was nervous. She waited, almost not breathing, as her Grandmother rubbed the tip of the toy over her pink wetness, sliding against the soft flesh without actually entering and taking her virginity. Rory looked up at her Grandmother, Emily's face was filled with excitement and lust, making the few seconds before she popped the teenager's metaphorical cherry last forever. She looked at the teen, directly staring into her eyes, "Your first time as my whore," she said and slid the toy between the gap.

At first it didn't feel much different that the times she'd used a dildo on herself, a little bigger possibly and her dildo was smoother and less lifelike. But it felt the same as it slid down the tunnel, the wet walls falling back and then swishing forward to envelope if like a hand going into a glove. But Emily was pushing deeper than Rory ever had, thrusting the toy into places the teen had never reached. And she was going harder as well, not caring about the tightness of the cunt, but just slapping away the resistance like a bull charging through the proverbial china shop. Rory gasped as the toy found spots she didn't know existed. If it felt different from a d-i-y job, it also was starting to feel a lot better. She looked up at Emily, a look of concentration on the Gilf's face as she slammed down. Her body was pushing onto Rory, her heavier tits heaving at the silk shirt and hammering at Rory's pert little pair. She moved faster and harder, giving her Granddaughter the full length of prick.

"Ooooohh," the teen moaned. She knew she'd been told to, but even if she hadn't she was sure she have cried out in pleasure. Emily was slamming quicker and deeper, getting herself into a rhythm of passion. The teen shuddered and gasped, arching her back and pushing herself at the down coming Gilf. "OOoohhh," she groaned again, "Fuck me, fuck me hard and good."

"Mmmnn that's it you little whore, tell me how much you want it, tell me how much you want Grandma's dick," Emily grinned as she pushed and thudded down.

"Oooohhh give it me good and deep, Grandma, ram my tight teen pussy. I'm a dirty little skank hooker, fuck me like one. Ooooohhh, uuuuhhh, I want that plastic cock hard in my cunt," Rory squeaked and squealed and even though she was getting paid for it, it was also true. The thud of the dildo deep into her pussy was the most pleasurable thing she had ever felt, the sensations tearing through her were so intense she felt like she was about to crack. Her muscles were tearing and contracting, her heart pumping like it was about to explode, her brain fizzing in some sort of orgasmic overdrive. She reached out and gripped her Grandma's back, dragging her in faster and deeper, "AAarrhhh, uuurrhrhh, fuck me, fuck me, fuck me so hard."

Emily responded to the encouragement by hammering down even more violently, slamming into Rory so vigorously the bed rocked. Rory squealed in pleasure, her hands gripping the silk of her Grandmother's pyjama's, her nails digging into the soft material. The older woman's face was contorted with effort and lust, her mouth twisted and open, breathing heavily. Rory never believed her Grandmother's hair would be anything but perfect, but in fucking her she discovered she was wrong as some strands broke away from the coiffure. A trickle of sweat rolled down her forehead, something else Rory had once believed was impossible, before it dripped off and down onto the teen's face. Emily grunted, "Take it whore, take my big dick."

"Yes," squealed the teen, "Hammer my hole, bang my slit. I want you to fuck me hard and good, Grandma, fill your hooker granddaughter with cock."

"Uuuhh, uuuhhh," Emily panted in reply and slammed down. She might be old, but she had energy and Rory hoped she was half as active when she was half the older woman's age. "Uuuhhhhh, uuuuhhhh."

The dildo pounded down deep and fast, slamming at Rory's erogenous zones and making her buck with pleasure. Her back bent and every thing else shuddered and shook and she screamed her joy, "Aaaaarrggghhh, yessssss, aaaarrrgghhh."

"Uuuhhh, uuuuuhhh," Emily panted pounding down. Her body smacked into her granddaughter's crushing the teen onto the bed. She was going so fast that the toy threatened to drill all the way through. Rory didn't care, she was in heaven, her body a haven of delight. She dimly thought that enjoying it this much must make her a natural lesbian hooker, but the pleasure was so intense she didn't care. Her body bent again as she felt the bliss of sex come to her.

Without warning Emily rolled off, leaving Rory on the cusp of the orgasm. The older woman lay panting as Rory quickly replaced the toy with her fingers and slammed in. It was too late, digits failed to compete with dildo and whilst it felt nice, it wasn't earth shattering. She slid her finger out. "Was that okay?"

Her Grandmother ignored her, still getting her breath back after their hardcore sex session. But it only took a second or two for Rory to realise that the lack of reply wasn't because Emily couldn't speak, but because she was a prostitute, as much a hired help as the maid and you didn't converse with the staff, you just gave them instructions. Later on round the dinner table Rory might be her granddaughter again, but here and now she was a hooker to be fucked. As if to confirm that Emily turned, "Roll on your front Rory, I want to introduce my strap-on to your butthole."

"Yes Grandma," Rory rolled over as she was told, spreading her legs slightly so that Emily could move between them.

The Gilf remained in situ for a moment, looking down lustfully at the ass, before she spoke, "You might want to bite down on the pillow as anal sex can hurt the first time, especially if you pound the hole as hard as I'm going to."

"Okay," Rory did as was suggested, biting deep into the pillow and gripping it with her hands.

Emily continued to look down lustfully at the teenager's tush. "That looks such a tight little hole, I'm really going to enjoy it over the next few years. I'm paying a lot of money for this so you need to get used to idea of being anally banged; if you're anything like your mother it'll be my regular hole. I used to ram her there all the time, she used to love it, but not as much as me. But then she wasn't a whore who I was paying for."

Rory didn't speak, she was being talked about rather than too, an object for the older woman to slate her lusts with.

Without warning Emily was on top of her, the older woman gripping her ass cheeks and pulling them apart. Then placing one hand on the dildo she guided it to the virgin rosebud. It tickled as Emily placed it on the sphincter and brushed it over the hole, trying to find the centre point. It took her only seconds to find the small dent in the middle and she shoved in.

She had been right about it hurting. Rory bit the pillow as a surge of pain shot up her hole. But even as it burnt and stung a wave of excitement was merging with it. Emily raised herself a little and then thrust down again, the dildo ramming into the tight, virgin hole. Rory teeth gripped the pillow tightly as a rush of intense pain shot through her. Her nails dug tightly into the material as well, almost tearing through the cover and into the downy pillow itself. Emily was on top of her, hands on either side as the toy was in deep enough that Rory's ass held it in place. She thrust in and pulled out, each time getting a little deeper down into the virgin territory. Rory's anal walls resisted manfully, but they were no match for the lust filled Gilf. She pounded in, expanding the hole further and Rory's back bent in pain. Her eyes watered and she blinked back the misty tears, concentrating on what a good education she'd be getting and how she would sail into Harvard.

"This ass is so hot and tight, Rory, I bet its agony to be fucked," Emily grunted and hammered down.

Rory squeaked into the pillow, dragging it towards her face. It was agonising, but it was also exciting, waves of ecstasy flowing up with the pain. The pleasure wasn't enough that she liked anal, but it was enough that she could just about cope with it. Her Grandma pounded down deeper, spearing her asshole with plastic dick. The older woman was putting in all her effort, giving the teen a hard anal fucking. The toy was going in deeper each time until Rory could feel the crash of her Grandma's hips against her as the strap-on went all the way in.

If the teen had thought the Gilf would slow when she achieved full penetration she was quickly disabused, if anything Emily went even more speedily, slamming the toy as far in as it would go with the vigour of a much younger woman. Rory's ass seemed to be on fire, as was her pussy, but with a different type of blaze. The cunt was leaking girl juice, the cum staining the sheets underneath her - it seemed her body was loving the anal, the teen wasn't sure whether it was because the pleasure was so intense or whether it was the pain that was the turn on. Or even both together. She screamed soundlessly into the pillow, a shriek of both agony and ecstasy and her teeth bit down so she could taste the silk, and through it, the feathers.

"That's it my anal hooker, let Grandma fuck your ass for money. I'd say you were a cheap whore, but we both know you were very expensive. Still as I get to fuck this tight ass every week I've got value for money," Emily grunted as she hammered in.

"Mmmmppfff," Rory snorted into the pillow. The older woman continued to vigorously sodomise the teen, her body smacking down and driving Rory into the mattress. She could feel sweat dripping down from Emily, coating the teen in the older woman's perspiration. The silk pyjamas were wet with it as well, coldly slapping at the teen's back with every thrust. Rory gripped the pillow, reminding herself how good her new school was and how much it cost. The dildo pounded deep into her asshole and her Grandma grunted something that sound like pleasure. Rory replied with a further squeal at the pillow.

"UUuhhh, uuuhhh, take it in your hooker ass, I paid for this hole and now I'm fucking it," Emily panted. "I bet you're soaking underneath you little whore."

"Mmmmpffff," Rory agreed as she was almost literally gushing. She raised her butt to meet the down-coming thrust, met it and was powered onto the bed. As she hit the mattress she could feel the soaking spot underneath her pussy. Her ass might have been pained, but to her cunt it didn't seem matter. Nor did it seem to matter to her Grandma who continued to pound her with speed and vigour, hammering her ass like one might do a stubborn nail.

"UUuhhh, uhhhhh," panted Emily, she slowed slightly but redoubled the power she put into fucking the teen's ass to compensate.

Rory grunted and rocked, shuddering on the bed as she came, girl cum spurting out her pussy to add to the rapidly growing wet spot underneath her. Her ass was so sore it was like a grater was being shoved down their; it was worth it for the pleasure. Her Grandma was right she was a whore, an anal loving one. She screamed and shrieked into the pillow. It came out as muffled cries "Mmmppff, mmmmppfff!"

Emily grunted again and stopped with a final thrust. She lay on Rory's back panting heavily, her dildo still encased in the brunette's back hole. The younger woman lay still, her mouth still fill with pillow and her hands gripping it like if she let go she'd be dragged into a black hole. After probably half a minute Emily levered herself up and sat against the headboard, the cock sticking out over the top of her pyjama bottoms like a rocket launcher about to let loose a V2.

Gingerly Rory let go off the pillow, she could see bite marks in the perfect silk cover.

"Suck my cock, Rory," her Grandma said.

"But it's just been in my butt," Rory gasped in shock.

Emily looked at her sternly, "I hired all your holes, every Friday."

"Yes, of course," Rory blushed and climbed onto her knees. She turned round so she was parallel to the headboard and put her mouth down. She closed her eyes not wanting to see the cock as it approached and opened her mouth. It tasted rank and bitter, as if it had just been pounded into an ass, she thought. But she swallowed it down, going deeper and thinking of her education the whole time.

"MMmnnn, that's it, that's a good whore," Emily said, pressing on her Granddaughter's head; she didn't exactly force her down, but it was stronger than encouragement. Rory took the cock deeper, trying to pretend she wasn't sucking in her own anal juices. The toy slithered across the inside of her cheek and threatened her throat; she gagged a little and saliva slithered down the plastic prick. Emily put more pressure on the back of her head and Rory swallowed more, her eyes watering and her stomach threatening to wretch. Just as she did think she was about to Emily released her and Rory's head sprang up.

"Carry on cleaning it, I want it shining," Emily said and placed her hand on the back of Rory's head again. The teen knew what to do this time and went deeper faster, so that she wouldn't need to be pushed. She let the toy graze across her cheek and at the top of her throat, before she pulled back. Emily let her get her breath back for a second before applying some more pressure and pushing her back down. Rory went, cleaning the cock and sucking up her butt juice.

Her head continued to go up and down, until her mouth was dry and the toy was so clean it could have been sold as new. Emily let go off her head and Rory brought her mouth up a final time, gasping for air as she let go off the dildo. Emily got off the bed and stood up, walking to the door. She opened it and turned, midway between the bedroom and the hall "The maid doesn't come in until after noon tomorrow. If you want breakfast there's some cereals in the kitchen."

She closed the door leaving Rory alone with a dry throat and a sore ass...

* * *

When Rory awoke the next morning her ass ached. She moved gingerly at first, wanting to make sure her insides didn't come out, but when they didn't she tried bending over, stretching up and eventually sitting on it. The butt ached for each, but not agonisingly so, more like a dull throb and Rory realised that for next three years every Saturday morning she was going to have the same pain. Then she thought of Harvard and it was worth it. She looked at the clock next to the bed, an old-fashioned but expensive alarm clock complete with bells on top. It was not yet ten, early for Rory on a weekend. Usually she'd stagger out sometime after eleven to meet her equally just up Mom and together they'd zombie shuffle to the car and then on to Luke's for coffee and a cooked brunch. She didn't think her Grandma would appreciate the morning daze shuffle so she took a quick shower to wake herself up before pulling out the clothes she brought for Saturday morning.

They weren't things she'd have worn normally, being totally slutty; a pair of hot denims cut off at the top of the thighs and which clung to her ass as tightly as a limpet and a vest which was so small it hardly classed as a top. It was whore wear and she was a whore. She went downstairs.

"Morning grandma," she said as she entered the dining room.

Emily looked up from the morning paper, "Morning Rory," she said neutrally. She didn't mention that she'd fuck her granddaughter like a literal hooker last night and if her eyebrows raised slightly that might have been from the bitterness of the expresso she lifted to her mouth immediately the words were out. The teen posed for a couple of seconds against the door frame, trying to appear both casual and sexy as she stuck a leg out and leant her back against the wood. She was coming to recognise that to her Grandma she was both a bright star of a granddaughter and dirty whore to be fucked, she didn't understand yet how Emily separated them in her mind - if she did. The older woman put down her coffee and indicated some cereal boxes sitting on a table at back of the room, "Help yourself to cereal."

Rory did and also to some freshly brewed coffee (the real nectar of the Gods, the teen believed). She sat down, wincing a tiny bit at the ache in her ass. "Sleep well?" she asked conversationally.

"Very," her Grandma replied politely and returned to reading the paper. She was either not a morning or something very interesting was happening in the news.

The teen finished the rest of her breakfast in silence, wondering what to do when it finished. Should she sit here in silence? Go and find a television (if there was one)? Perhaps go to her room and read? Or dance round her Grandma whilst pulling up her top and down her hotpants? She was almost finished the breakfast and no nearer making a decision when her Grandma folded the paper and looked at her. "I see you're dressed as a whore."

"Yes, Grandma," Rory nodded.

The Gilf looked her over and it was hard to tell whether it was in approval or disgust, her expression remained the same. Eventually she gave a curt nod, "If you go into the second drawer in your room you'll find something more appropriate to wear."

Rory nodded and stood up, leaving the last few mouthfuls of cereal still in their bowl. She was bought and paid for and if her Grandmother wanted her to change she'd do it straight away, Chilton was worth it. She walked up the stairs wondering what was in the drawer and what her Grandmother meant by more appropriate. If it was a blouse and long skirt, her Grandma was expecting her to be good girl Rory; if it was an even smaller pair of shorts and top it was Rory the whore that her Grandmother wanted.

When she opened the drawer it took her a few moments to realise what it was. The only thing in there were what looked like several interconnecting leather belts, more like a missing part of an exercise machine than something you'd wear. It was only when Rory pulled it out she saw that it was shaped to fit round a body. She got out of her own clothes and stood naked in front of the mirror trying to work out how the leather strap suit fitted. Luckily the teen had a sharp mind and after a few experiments managed to get herself equipped. She blushed, as she looked at her reflection, she did look like a whore. The leather wrapped round her tits squeezing them out and making them rounder. Then it went up round the back of her neck and down under her sides, the straps sliding round her pussy lips, pulling at them and leaving the slit slightly agape and then round through her butt crack to a small belt at the back which held it in place. Dressed like this she didn't think she and Emily would be discussing the Schleswig Holstein question.

"I'm ready Grandma," she called as she descended the stairs.

"In the main front room," her Grandmother called back.

The teen finished her descent and walked towards the main room, her feet bare on the expensive carpet. Emily was sitting on an expensive chair, reading a book. She put it down on a table next to her as her granddaughter entered and placed her reading glasses on top of it. Her gaze transferred to the nearly naked teen, looking her up and down. "That's more appropriate for a teenage hooker to wear don't you think?"

Rory nodded, "It is."

Emily stood up and walked over and around her, her eyes moving up and down the teen. The difference in their clothes was apparent, Rory in just some straps, her Grandmother in an expensive skirt, with matching jacket and a blouse that was silk with buttons that weren't made from mass produced plastic. The Gilf stopped behind her, "Your mother gave me some pictures of you posing."

"She did," agreed Rory, she and her Mom had spent all day taking them as part of the sales pitch to Emily. They'd all been very sexy and the teen was kinda proud of how she'd come out in them, they'd obviously impressed her Grandmother as well as otherwise she wouldn't be here.

"They were very sexy, did you enjoy taking them with your Mother?"

"We did, it was fun," Rory agreed.

"You looked like a whore," Emily said, the words were without rancour or judgement, like she was stating that the sky was blue. "You'll pose for me, like the hooker you are."

"Of course," Rory nodded. Her Grandma went over to the bureau and opened it to retrieve what looked like a very expensive camera.

Rory thought she'd take the initiative and bent over sideways over the nearest couch arm rest, twisting her upper body so that her left tit was easily visible. Emily grinned and took a shot. "That's right Rory, you show me you're a whore."

Straightening up Rory turned full frontal to her Grandmother, her lips sensually licked round her lips, whilst she slid her hands down her sides. Her Grandmother snapped again, a flash filling the room. The teen ran her tongue out further, whilst moving one hand down to her pussy, she gently stroked it whilst with the fingers on the other hand she found a nipple and teased it. The camera flashed again. It was time for a rear shot, thought the teen, turning her back towards Emily. She could hear the camera shutter bang, it was an old fashioned camera with film, not a digital. The teen placed her hands on her rump, wondering how her Grandma was going to develop the photos, she couldn't just upload them onto a computer and print them out like she and her Mom had done with the others. Did that mean that some stranger in a photos hop would also be staring at her nakedness? She spread her ass, exposing the taboo hole that her Grandma had hammered so hard last night. The camera snapped. Rory widened the pull, blushing at the thought of some guy jacking his cock over her nakedness as he developed them. She didn't pull back, though, her education was that important and she was willing to pay for it. Her hole split open and she could hear Emily grunt something as she took another shot.

The teen turned round and walked over to one of the chairs. She sat down in it, striking a demure pose, out of keeping with the leather sex-garb she was wearing. Her Grandmother took the shot anyway, perhaps appreciating the contrast between the innocent expression and the whore dress. Rory moved her hands from covering her boobs and opened her legs a fraction, the camera clicked again. She continued with the move, sitting back on the chair and placing her legs over the arm rests. Emily's eyebrows raised at the lack of respect for the antique furniture, but she snapped away anyway and then again as Rory moved her hand down and slid a finger into her pussy.

The Gilf put the camera down, "That's enough," she said, her voice thick with lust. "Let see what you can do with that sweet little hooker tongue." She stood up and walked over to the rug and undid her skirt. It fell to the floor and she bent over to pick it up, her blouse drifted so that Rory could see that was no underwear underneath. The Gilf carefully folded the skirt up as she said to Rory, "Come and lie here. I'm going to ride that beautiful face as you tongue fuck me."

"Yes," Rory did as she was told.

The rug was hairy and tickled against her naked skin. She had barely time to notice it and to squirm into a position where it wasn't making her ass itch before her Grandmother was over her. The older woman lowered herself, slowly and delicately so as to look after her joints. As she descended Rory's vision became more constricted and the light turned to dark until all she could see was the puffy, plump lips of her Grandmother's cunt, looking like it was freshly shaven. The teen raised her head to meet it and licked up, sliding her tongue over the labia. "Mmmnnn, that's right, you dirty little cunt licker," her Grandma said. She continued down, pressing against Rory's head and forcing it back on the carpet. The Gilf wriggled, finding the exact spot where her granddaughter's mouth could connect with her cunt. "Tongue it, you slut," she said.

Rory did so. She was surprised how quickly it became wet, she had thought age made women drier, if this was true it didn't seem to have effected her grandmother, the woman pussy was damp and Rory's tongue made it damper. Unable to see anything or hear much beyond muffled grunts and groans, all that was left was taste and touch. She could feel the smoothness of her Grandma's thighs squeezing at her cheeks and the softness of her pussy lips as they vibrated with each touch of the tongue. The taste was bland with just a trace of salt and sweet, but with a tepid warmth like a coffee which had been left for too long. Still she lapped hard.

Above her Emily groaned and grunted, grinding her cunt at her teen granddaughter's face and getting the most she could from the teen. Cum leaked from the pussy, covering Rory's lips and down her chin, smudging her lipstick and rubbing it into her mouth, so she could taste the flavour of gloss and cum mixed. "MMnnnnn, faster, Rory, faster. I want my cunt to be pleasured."

Speeding up Rory ploughed her tongue into the wriggling twat, diving deep and hard, lapping down the juice. "Uurrhhh, urrrrhhh, that's better," her Grandmother called, "Use that whore tongue."

The teen pounded up, each lick producing a corresponding shake from the Gilf, her thighs clattering at the teen and her ass pressing down, pushing the back of the teen's head into the rug. Rory was glad that it was there, despite the tickling, it cushioned the back of her head and without it she knew she'd be suffering a splitting migraine. Her tongue swept up and faster and her Grandmother shook even more, squealing loudly in a most unEmily way, "AAaarrrrghhh, aaaaaaarrrghhh, aaaaaaarrghhhh."

"Uhhhh," with a grunt Emily lifted herself, her cunt dripping a mixture of cum and saliva. She looked down at her granddaughter and a faint smile creased her lips, "For a beginner you're a very gifted cunt licker, by the end of these three years you'll be fit for anything."

"Thank you," Rory blushed, unsure whether it was a compliment or not, but deciding to take it as one.

The doorbell rang, it sounded even louder inside than out, like Big Ben chiming in a house. Her Grandmother looked at her, "That will be Lorelai, you should let her in."

"Um, dressed like this," Rory indicated the leather straps she was clad in.

Her Grandmother's mouth twitched, "Of course. Your mother didn't think you'd be wearing a flowery dress and doing embroidery when she sold you, you should show her what a whore daughter looks like."

Rory blushed a little. She'd known intellectually that her Mom would know exactly what was happening, but somehow standing in front of her almost undressed made it seem more real and a little degrading. But then she thought of Harvard and what it meant to her. "Yes," she said and went to answer the door as her grandmother picked up the skirt and started to get back into it.

Her Mom's eyes widened in surprise and her jaw dropped as Rory opened the door with her pussy on display and her boobs plumped up. She quickly recovered her poise, perhaps she was her mother's daughter after all, "Are you ready to come home now?" she asked.

Emily appeared behind Rory, back to being fully dressed and with not a hair out of place in her coiffure as if a few minutes ago she hadn't had her cunt jammed down on Rory's mouth. "Invite your mother in Rory, whilst you get your things. You might want to change into something else, I'm not sure your leathers are suitable for the trip home," she smiled as a Grandmother might and then turned back to Lorelai, "We've had a very enjoyable time. I'm looking forward to Rory coming over next week."

* * *

If you have any views on this or any other of my stories, please e-mail me at [email protected]


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