A Proper Young Woman’s Guide to Anal Etiquette: Foreword
By: Lord Odie
Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supervision. Any physical resemblance to a real person that any fictional character herein may bear is probably intentional and is meant as a compliment. Furthermore, all fictional characters in the following fantasy are professionals and good at what they do. So please, don’t try this at home; if such things were even physically possible. If you still insist on trying this at home, please send all pictures and feedback about the experience to myself at: lordodietheauthor@gmail.com. If I can’t stop you I can at least make sure you’re doing it right. Consider yourself disclaimed.
Background
Our story takes place in the not too distant future where the proper, conservative upbringing of respectable young ladies includes the ingrained obedience to authority figures of any type, whether it’s teachers, bosses, parents, or significant others. In the case of heterosexual relationships the authority figure is obvious. In far more common lesbian relationships since, for some unknown reason of nature, women now outnumber men five to one, one of the two partners inevitably takes on the role of authority and the other quickly becomes the subservient. Both heterosexual and lesbian relationships are equally acceptable in the society of the day. Regardless of the type of relationship, one thing is consistent throughout all decent, socially acceptable pairings: the unyielding anal submission of the subservient female. The anal submission by the dominant female is totally at her own discretion.
Young ladies are expected to be instructed by their mothers and older sisters from the time they come of age, which is the time they start having sex on their own, to accept objects into their anal cavities. This training continues into the girls’ late teens and early twenties as they’re taught to accept still larger and larger objects into their nether holes until they can’t achieve sexual satisfaction without those holes being fully, and sometimes painfully, packed. That doesn’t infer that anal training stops there. A proper young woman’s anal education is a lifelong commitment by all members of society.
This isn’t to say that sexuality is publicly flaunted, as such displays are considered gauche and amoral in the future. In the privacy of the home, of course, anything goes and usually does; sexual depravity being the norm behind closed doors. But in public, what is considered proper social behavior has come full circle to what was acceptable maybe in the 1950’s. A little bit of cleavage on display is okay but tits about ready to pop out of a top is too risqué. A skirt at mid thigh length is perfectly acceptable whereas if the ass cheeks are clearly visible below the hem line, the lady in question is likely to get arrested for solicitation. Equally, that’s not to say that every passerby is oblivious to the very likely fact that all the conservatively dressed business women walking down the street have large plugs up their bottoms and maybe a set of tight nipple clamps crushing their aroused nipples, if the lady in question were so inclined. Quite the contrary in fact. It’s just socially unacceptable to mention such things in polite company. A knowing glance at the cute girl in the next cubicle as she squirms uncomfortably in her office chair is enough to communicate that everyone knows the reason why.
This is the way of the future world. And this is the world in which we find our main protagonists. Meet the Wilders family, consisting of the buxom Laura and her five beautiful daughters: Emily, Cora, Naomi, Mary and Amanda.
Name: Laura Wilder
Age: 46
Occupation: Bank branch manager
Vital Statistics: Tall, petite, 34FF cup breasts, dark red hair
Laura is a very desirable cougar and socialite, and the mother to five lovely daughters. She was brought up in a strict, conservative family; which in today’s day in age means the most strenuous anal capacity training imaginable. Laura insists on teaching strict anal discipline to her five daughters, which makes her a good mother by today’s meter stick. She has a ‘thing’ going on with her young secretary, Tanya, while she looks for a new Mr. or Mrs. Right. Her husband, Dave, died of a heart attack a few years prior leaving Laura and her daughters to want for nothing; financially at least. But this has left Laura’s other wants yearning for the strict discipline that she has enjoyed at the hands of her late husband ever since she was a teenager.
Inspiration:
http://gweedopig.com/index.php/2009/08/23/hottie-of-the-week-bianca-beauchamp/comment-page-2/
Name: Emily Wilder
Age: 18
Occupation: High school senior
Vital Statistics: On the short side, very petite, 32B cup breasts, fiery red hair
Emily is the youngest of five daughters and a veteran of both the swim and tennis teams. She is the black sheep of her family in that she hasn’t taken to extreme anal penetration as enthusiastically as her older sisters have; and nowhere near as much as her mother insists she does. Although she doesn’t like to admit it, she really does get off on anal stimulation just as much as her siblings and mother. It’s just that her teenage rebelliousness insists that she prove her mother wrong; even though she know deep down that her mother is right. Emily is currently pursuing Matt, the captain of the boys swim team.
Inspiration:
http://galleries.onlytease.com/1162p-p/pics/14n.jpg
Name: Cora Wilder
Age: 18
Occupation: High school senior
Vital Statistics: Medium height, athletic, 34D cup breasts, brown hair (dyed black)
Cora is Emily’s closest sister, being only 10 months older than her. While Emily is introverted, Cora was a social butterfly on the varsity cheerleading squad and is up to date on the latest gossip for almost everything and everyone. While she is just as athletic as her younger sibling, she has a slightly more curvaceous figure and larger breasts which she flaunts freely, much to the chagrin of her very conservative mother. Cora is currently in-between serious relationships right now but she has an on again, off again relationship with her best friend Stacy; who is also on the cheerleading squad.
Inspiration:
http://www.redbloodedthing.com/galleries/Met-Art-Provare-Dark-Curly-Hair/met-art_AF_765_17.jpg
Name: Naomi Wilder
Age: 22
Occupation: Waitress and aspiring model
Vital Statistics: On the tall side, petite, 34C cup breasts, brown hair
Naomi relishes in her role as the middle, wild child. With a rock hard body very similar to her younger sister Emily’s, but with larger breasts, she can turn heads whenever she wants to. Naomi is an aspiring model who holds down a day job as a waitress in a private, European style club in between gigs. She distinguishes herself from her mother and sisters by being masochistic almost in the extreme; which was saying something for a family of overtly masochistic women! She is currently dating Dale, the night manager of the club she works at; despite her mother’s disapproval of him. She’s also seeing Rebecca, a fellow waitress at her club, on the side.
Inspiration:
http://www.bettinabush.com/babe-of-the-day/
Name: Mary Wilder
Age: 26
Occupation: Legal aid and secretary
Vital Statistics: Medium height, curvaceous, 36FF cup breasts, brown hair
Mary is the second oldest sibling of Emily’s and the only one of Laura’s daughters to match her in the breast size department. Mary never had a problem in the lady department; being uninterested in men all together. When she was a junior in high school she was involved in a bad car accident and can’t feel her legs anymore and is confined to a wheelchair, being incapable of walking. Fortunately, nothing is wrong with her lady parts and her desire to use them. She lives with and works for her fiancé, a 34 year old lawyer named Victoria. Victoria, for her part, finds all manner of interesting things to do with her beloved Mary and her chair bound condition.
Inspiration:
Name: Amanda Wilder Fallon
Age: 28
Occupation: Small business owner and inventor
Vital Statistics: Medium height, curvaceous, 36DD cup breasts, dark red hair
Amanda is the oldest daughter of Laura. She is the only one of her siblings to have graduated from college with a degree so far; which she earned in mechanical engineering. Amanda is just as curvy as her younger sister Mary, but with slightly more proportional breasts and her mother’s dark red hair. Her husband, Todd, 31, is also a college graduate with a degree in computer engineering. Together, they own a company called Anal By Design, which specializes in sophisticated, high end computerized training aides designed for the use of extreme anal dilation and capacity training. Amanda really enjoys being self employed and insists on personally field test everyone their designs; for safety and liability reasons of course.
Inspiration:
http://hosted.met-art.com/met-art_mw_47_127//full/met-art_mw_47_9.jpg
A Proper Young Woman’s Guide to Anal Etiquette: Chapter 1
By: Lord Odie
Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supervision. Any physical resemblance to a real person that any fictional character herein may bear is probably intentional and is meant as a compliment. Furthermore, all fictional characters in the following fantasy are professionals and good at what they do. So please, don’t try this at home; if such things were even physically possible. If you still insist on trying this at home, please send all pictures and feedback about the experience to myself at: lordodietheauthor@gmail.com. If I can’t stop you I can at least make sure you’re doing it right. Consider yourself disclaimed.
Masturbation
Eighteen year old Emily moaned softly to herself as she tried to jill herself off as quietly as possible in the soft confines of her own bed. She’d already kicked off her sheets and was lying, naked from the waist down, spread eagle for all the world to see; should anyone other than her sister, Cora, have been present in their large bedroom to observe her. She’d taken care to ensure the rest of the family was sound asleep fifteen minutes ago when she’d begun her nightly masturbation session. She knew Cora wouldn’t have bothered her even if she had been awake; other than to maybe watch her performance quietly and lock the mental recording away for later use. But her sister almost always got herself off earlier in the night and slept like a very satisfied rock until Laura, their mother, woke them up in the morning. Emily glanced at the clock again. 3:24 AM. Good, she reassured herself. She should be able to orgasm at least once or twice, maybe even a third time if she was still feeling horny, clean up and be back to sleep without anyone being the wiser to her nocturnal activities.
Emily was still wearing her old, faded, tight pink Hello Kitty T-shirt, which was her favorite nighttime sleepwear. And that was it. She glanced down again, past her perky, medium sized breasts, with the rock hard nipples clearly visible even in the dimly lit room’s light, over her flat, athletic stomach to the empty doorway and out into the hall; it was a nervous “God, please don’t let anyone be there” action she did repeatedly while she masturbated at night. She would have locked the door to their bedroom if any of the rooms in the house, other than a few of the closets, actually had doors on them. Her parents had firmly believed that a close and loving family had no secrets to hide from each other and therefore no reason to close any doors; and even less reason to lock them. The first thing Emily’s father had done with all the doors in any house they’d ever moved into was remove all the doors and put them up in the attic, only to be re-hung if and when the house was resold. It was kind of a forward thinking concept, even in today’s day and age, but Emily had grown up with it so it was as normal as normal got; even if it was a bit inconvenient when she attempted to get herself off in relative privacy.
Emily returned her attention to the moist slit between her legs. If her mother ever caught her doing what she was doing to herself there’d be Royal Hell to pay. That was sure as death and taxes!
Well, it wasn’t as much as what she was doing to herself but how she was doing it.
Emily’s right hand was working her clit furiously; her left hand was busy plunging two fingers in and out of her dripping pussy, trying, and succeeding, to tickle her G-spot each time she bottomed out in her sloppy front hole. While her fingers focused on the – all too important – task at hand, her mind was replaying her memory of the captain of the swim team’s glistening, barley clothed body climbing out of the school’s Olympic sized pool. Of course, in her version of events, the skimpy little Speedo he wore for competition swimming was conspicuously absent; the source of the large bulge in the front of said Speedos was not. Emily had been, not so subtly, pursuing Matt for over a month now and she’d finally succeeded in getting that elusive first date only yesterday. She couldn’t wait for Saturday night to get here so she could be alone with him! She’d succeeded in winning his attentions where at least a dozen other girls who’d been fighting for them had failed. The race for Matt’s heart, or at least his loins – “those huge, beautiful loins” Emily obsessed longingly to herself –, had been ongoing ever since he and his longtime girlfriend had broken up a month and a half ago. A pack of starving wolves fighting for a succulent lamb lost in the woods was not an inaccurate metaphor for the weeks long contest. “And Matt thought he had faced fierce competition when he won state last year in the 100 meter butterfly!” Emily added mirthfully.
Last night’s masturbation session had been the most fervent in recent memory as she’d celebrated her hard won dating victory in her own, private way. “Tonight’s is promising to be almost as spectacular” she thought to herself as she came closer and closer to losing herself over the peak of her approaching orgasm. Emily tried, again, to ignore the large hunk of latex buried up her bottom hole as her hips gyrated in rhythm to her expertly dancing digits. Tired and failed. She would have just taken the plug out before she started diddling herself but she’d long since realized that her orgasms didn’t seem anywhere near as strong when she masturbated with an empty butt; Emily was just too well trained for that to be the case. “Damn my mother and her notion of a proper upbringing to Hell”, she thought as the peak drew ever closer. “If it wasn’t for her insistence on such a ‘proper’” she vehemently cursed the word, “upbringing for a young lady I wouldn’t have this need to have my butt packed just to get off!” she complained bitterly. Emily always told herself she kept the – thrice damned – plug up her bum while she masturbated just in case she got caught so that she’d have a readily available out. She didn’t like admitting the truth; even to herself in the privacy of her own mind.
Her mother had always insisted that her daughters, of whom Emily was the youngest, maintain a properly dignified amount of anal dilation; which meant that they were all required to sleep with a large, smooth plug buried deep up their backsides since they were old enough to have sex. Her older sisters had taken to it well enough, enthusiastically some would say – very enthusiastically in her oldest sister’s case –, but the young Emily was a stubborn child and had refused to accept her mother’s anal administrations with anything approaching the gusto of her older siblings. For example: Her oldest sister, Amanda, was ten years older than herself, an intelligent, driven college educated woman with a degree in mechanical engineering, and happily married to a really great guy. And she still kept her back hole well stretched and open for anything her overbearing mother, or overly supportive husband, fancied to shove up there. In fact, if Todd – her aforementioned husband – wasn’t around, she’d damn sure invent something to stretch her butt out still further just to satisfy her own craving for it; just because she could! It was all madness to the young woman masturbating quietly in the dark!
Emily’s mind lingered on her oldest siblings butt without her realizing she’d switched mental gears. The way it just gaped loosely open on the rare occasions when it wasn’t being forced open wider still by her husband’s cock, a large plug, a first, or something similar. The memories of that well trained posterior had always excited her more than she cared to admit. Just focusing on it now brought her to the peak of her nearing orgasm. “Wait, God damn it! I’m supposed to be thinking about Matt, Matt, not my sister’s butt” Emily scolded herself; trying to get her mind back on track. “Damn my mother to the very depths of Hell for this entire anal fixation!” That was Emily’s final though before a hand closed around her wrist and jerked it away from her throbbing clit just as the waves of orgasm where about to knock her off the very precipice of that very peak.
Emily gasped in frustration and instant furry just long enough for her eyes to fly open and see her mother standing over her, grasping her arm firmly and with disapproval on her face. Emily’s approaching orgasm immediately retreated in a full route from whence it came; her free hand frozen in mid plunge into her still spasming cunt. “Mother!” was all she was able to get out as she gasped for air. “I… I can explain!” she stammered in an attempt to justify her current state of arousal.
“Explain what?” Laura asked sternly. “How I caught you red handed, or wet fingered as the case may be, getting yourself off and leaving that wonderful bottom of yours completely neglected? Is that how I raised you young lady?!” she demanded. Emily remained silent and looked down, not wanting to meet her mother’s furious eyes. It was then she noticed that her hand was still half buried in her pussy; she quickly removed her fingers. “I thought not.” her mother replied to her own obviously rhetorical question. “Now clean those evil fingers off while I get out you masturbation kit.” Emily, ever the obedient daughter whenever she had no choice on the issue, immediately brought her soiled hand up to her mouth and began sucking the pussy juices off of her fingers while her mother turned on the bedside lamp to shine some light onto the situation.
As the light was clicked onto its dimmest setting, Emily, who’d been happily going about her business from just the glow of the nightlight in the hallway, immediately squinted her eyes in sudden shock at the brightness. She realized she must be a sight for perverted eyes now that the entire picture was clearly visible in the increase light: a damn near naked teenager wearing only a ratty T-shirt that left very little to the imagination laying across her bed with her legs spread as wide as they would go, an empty, sopping wet front hole, the base of a obviously large butt plug nestled comfortably between her wide spread butt cheeks in her rear hole, and Emily sucking her cunt juice slicked fingers – at her mother’s command – clean one by one; just the way she’d been taught to do. Any decent 20th century porn director worth his AVN awards would have given at least half a dozen money shots to film a scene like that. The panorama wasn’t lost on Emily’s mother who felt her own cunt moisten at the incredibly hot spectacle.
Laura, for her part, was the picture of a MILF in her purple babydoll chemise. In her late 40’s, she was determined to keep a hard body despite having given birth to five girls, and at this she succeeded spectacularly. She had to since she was officially back on the market after her husband’s death three years ago. Sexy chemises were her usual nighttime wear. They were comfortable to sleep in, and hot as Hell to anyone catching an eyeful; which was normally only her daughters. The one she was wearing tonight was one of her favorites: a sheer three-quarter cup affair which came dangerously close to exposing her now hardening nipples and barley contained her still firm FF cup breasts. Like her wayward daughter, she too was naked from the waist down; she and all her daughters normally went this way around the house. Also like her youngest and oldest daughters, she was a red head. Oddly enough though, the middle three girls had all turned out to be dark haired beauties. All six of them also shared the same pubic hair style that was the norm these days: that being nonexistent. It was hard to hide things like that when they had always slept bottomless around each other for as long as each had come of age. But what brought all six of the women truly together was the glimpse of hard latex that was usually poking out from between all their bottom cheeks; in this, Laura was no different than her daughters. “Those that can’t may teach, but those who can teach best” her mother had always said when she’d been growing up.
Incidentally, her late husband’s favorite saying had always been, “a pussy is for fucking and an ass is for stretching… and then fucking”. They’d always agreed on the basic theory if not the exact wording. And that was one of the main reasons her parents had loved Dave when they’d all been around; God rest their souls!
Out loud Laura said “I’ve been getting suspicious of your early morning activities, young lady, for a while now, but last night’s little escapade confirmed my suspicions. You were nowhere near as quiet as I think you thought you were. So I figured tonight I’d just check on you to see how you were handling things. Imagine my surprise to see you jilling yourself with just your pathetic little nighttime plug in. What would your father do if he were still alive?” Laura demanded quietly so as not to wake Cora, who was sleeping on the other side of the room. Emily could say nothing to help her current plight so she didn’t say anything at all; she just continued to suck her already clean fingers. “I’ll tell you what he’d do. He’d take both of us down to the basement, and maybe all your sisters too just to emphasize the point, and shove punishment plugs up all our asses! And we’d be sleeping with those, or larger, for a damn week!” Despite herself, Laura felt a pang of desire at the thought. She hadn’t been forced to wear one of her frighteningly large punishment plugs in years; there was no one around to punish her, after all. But as for her daughter, that would soon be corrected. “Starting tomorrow, I’m going to take charge of your nightly masturbation; which will be conducted when Cora does hers. You should be taking notes from her; she knows how to work a girl’s asshole over!” Laura said glancing over her shoulder at her sleeping second youngest daughter.
Emily glanced quickly over at her sleeping sibling; following her mother’s gesture. Cora was only ten months older than herself. They’d always been in the same grade at school leaving most people to think that they were twins; even though they bore little physical resemblance to each other and even less of a resemblance personality wise. While Emily was mostly introverted and favored swimming and tennis as sports, Cora was a social butterfly on the varsity cheerleading squad and was up to date on the latest gossip for almost everything. While both were toned and athletic, Emily was very petite and proud of her perky B cups while Cora was a bit more curvaceous and often displayed way too much cleavage, for their mother’s taste at least, with her much larger D cups; sizable assets which benefited her greatly when she’s been competing for the cheerleading squad. And of course, for the boys and girls in the dating pool. Despite those seemingly outward differences the two sisters were as close as any two sisters could be and were almost inseparable. During the day they ate lunch together, hung out in gym class together and had the same circle of friends. At night, even with Emily’s aversion to anal, they had spent many a happy evenings locked in a passionate 69 while they drove toys, fingers, and sometimes even whole fists, into each others’ maternally trained nether holes. Their mother would often watch them – quietly and approvingly – play in that manner from their door-less bedroom entrance before returning to her own bedroom and her own masturbation kit. This was an act of loving, sisterly bonding that they’d been taught by their next older sisters Naomi and Mary when both of them had still lived at home. They in turn had learned it from their oldest sister and their loving mother. And if history was any teacher, Laura had been probably been properly instructed in it from her older sisters and mother.
At this very moment, however, Cora was sound asleep on her front, half twisted up in her sheets, wearing a comfortable blue, cotton, sleeveless shirt. Conveniently, her derriere wasn’t a part of her that was covered up by her bedding and she wasn’t wearing anything other than her top either. This left the large round circle of the base of a butt plug, considerably larger than Emily’s but equally considerably smaller than their mother’s, clearly visible in the dim light. Even though Emily and Cora had come of age at about the same time, and had spent many hours lying on their mother’s bed, side by side, spreading their butt cheeks apart with their hands while their mother ravaged their rear holes in turn with progressively larger toys, Cora had taken to a proper upbringing enthusiastically while Emily had only grudgingly suffered thought it. After Laura had considered her two youngest offspring sufficiently trained in the proper mannerisms of young ladies, she’d let them continue their training at their own pace. Cora had continued with gusto while Emily had gradually all but stopped her anal dilation; which lead up to tonight’s predicament.
Laura continued berating her youngest daughter, “I’d just always thought you weren’t as interested in such things as a young girl should be. Imagine what would happen if you went off to college next fall and your roommate found you masturbating with such a small plug up your bum. You’d be socially ostracized! This is for your own good, young lady!” Emily diplomatically decided not to mention the fact that not all girls were brought up in the proper manner; some girls her age had never even so much as had a finger up their butts. The idea was absurdly odd to even her; she had no idea what her mother would say if she tried to use such an argument in her defense. Emily opted for discretion and so maintained her quiet finger sucking while her mother ranted her irritation.
Laura reached down between her youngest’s legs – past the excitedly dripping pussy – to easily extract the large, relatively speaking, plug from its hiding place. Despite the lack of regular stretching and workouts that the rest of the female assholes in the household subjected themselves to on a daily basis, Emily’s sphincter was nowhere near as tight and resilient as it once had been. She only grunted softly as the widest part of the plug left her body, leaving her with a very temporary feeling of emptiness; and her back hole gaping open a mere inch and a half across. The plug was about two inches in diameter at the base, about two and a half inches at its widest point and about six inches long; a sizable toy indeed at some earlier point in ancient history. Laura just looked at it and shook her head, then looked down at her daughter’s smallish gape and back at the plug.
“The first thing that needs to go is all of your small plugs. We might as well donate them to Good Will tomorrow since you won’t need them anymore.” Emily wanted to protest but thought better of it. “Now open up and clean this off.” Laura said as she lowered the slightly stained plug to her – for the moment – obedient daughter’s quickly opening mouth. Emily, to her credit, didn’t even flinch as her lips locked around the base of the soiled plug and her mouth and tongue got to the distasteful business of sucking it clean; it’s not like it was the first time she’d tasted that part of a woman’s body. Fortunately, the plug was only slightly stained since Emily still diligently maintained her regular enema regime; just because she wasn’t a fan of butt sex didn’t mean she didn’t like to be clean. “And get those fingers to work doing something useful for a change.” Laura demanded as she turned to get Emily’s masturbation kit. Emily quickly readjusted herself so that her forearms were under her butt cheeks and her hands went to work inserting fingers into her momentarily empty ass. She easily reached inside with three fingers of each hand and pulled hard; preparing herself for what both women knew was soon to come. Emily grunted in quiet consternation at the self imposed, and very unwelcome, stretching of her nether hole.
As Laura went to retrieve Emily’s masturbation kit from under the bed, Emily was treated to the appealing – despite herself – sight of the base of a truly massive plug protruding from her mother’s shapely ass as she bent over. “Damn!” Emily thought to herself. “A girl has to work hard at that for decades to take something like that up her butt and walk around like nothing was amiss.” Which was exactly how her mother had accomplished such a feat. Laura had had just as proper of an upbringing from her parents as Emily and her sisters had had from Laura and Dave. As big as she knew the plug was up her mother’s rear end, and only God knew how big it actually was, she knew that her mother was capable of taking much larger; much, much larger. She was just going easy on herself for her nighttime plug. Emily felt the familiar surge of lust and admiration she always felt when she saw her mother’s distended ass from so close. The sight before her restarted her previously stalled arousal; all thought of Matt lost for now. A girl just couldn’t grow up being personally involved in as much mother on daughter, or sister on sister, sex and not be turned on at such a view! She was her mother’s daughter, after all, and despite her own preferences, there was anal work that needed doing. The fact that the ‘anal’ in question was in reference to Emily’s own, uncooperative back hole was a minor point.
“Ah! Hear it is!” Laura quietly exclaimed quietly, still trying not to wake Cora, as she hauled the large suitcase size kit out from under the bed. “There’s actually dust on this thing! We need to spend a lot more quality time together, you and I, young lady!” Laura exclaimed. Emily’s masturbation kit was pink with Hello Kitty stickers stuck all over it; she’d always had a thing for the franchise; even today. The fact that such a cute box held such sinister tools of anal education, inevitably targeted at the youngest Wilder daughter’s illogically resistive anus, had always so turned on all of the other women in the Wilder household was no secret to anyone. And it was about ready to be opened back up to administer an aptly deserved lesson to the young woman in question. The well used kit was placed on top of Emily’s nightstand and reverently opened, revealing the tools with which Emily’s back hole would soon be abused with. The top of the kit contained a row of a dozen flesh colored, realistically veined, dildos ranging from two inched thick and six inches long to a whopping five inches thick and eighteen inches long, as well as a row of twelve similarly sized butt plugs just beneath. There was an empty spot in the lineup of butt plugs where the plug that was now being diligently tongue washed in the teenager’s mouth would nominally be stored; it was the second smallest one. The bottom of the kit contained an assortment of miscellaneous tools: inflatable butt plugs, nipple clamps, anal beads of various and frightening sizes, magnetized dildo harnesses, magnetized chastity belts, magnetized suction cups, magnetized handles, several more specialized plugs and dildos, a few punishment catheters, ball and dildo gags, etcetera. Fun things like that. Although, there was nothing present in the kit that wasn’t a common enough teaching aide for any young woman of proper, conservative upbringing.
Laura selected the three inch wide, ten inch long veined dildo form its storage place and gently massaged it as if it was a real cock. “Ah. The veined dildo: A girl’s first line of defense in the never ending battle against having an asshole that’s too tight.” Laura observed as she reached back into the kit for some lube and a magnetized handle. “We’ll start with this one tonight and work our way up something more fun another night.” She commented offhandedly. The plugs and dildos themselves were all magnetic and could be attached to a multitude of accessories. The handle Laura had selected and snapped onto the intimidating dildo was a sturdy two handed affair; perfect for getting a firm grip with both hands to drive whatever point had to be made home into whatever resistant hole happened to be available.
Her tools selected, Laura moved to the foot of Emily’s bed and crouched down between the reclining teen’s widely spread legs as her daughter continued to finger her already slack rear hole. “Go ahead and get your fingers out of mommy’s way, dear.” Laura instructed. “Just pull your cheeks apart and help mommy stretch you out a bit more by staying relaxed.” Laura continued and Emily immediately complied. Laura paused for a moment to appreciate the view and wonder if her own ass had ever had that small of a gape; certainly not for many, many years. Maybe when she was sixteen and had been having sex with her then boyfriend for almost a year, but certainly not long after that since her parents had found out about the affair soon thereafter and had started her anal dilation training almost immediately. The yawning black cave that was Emily’s rectum was clearly visible in the soft light, just below her obviously moist pussy. Her hands were on each ass check pulling them apart as hard as she could but the open hole itself was only a pitiful two inches across at its widest point. That was just unacceptable in any daughter of Laura Wilder’s!
Laura set the formidable tool to the side for the moment to quickly dip two, then three, then four fingers of her right hand up her daughter’s rear. In no time at all, she had half her hand buried into the quickly expanding back hole of the young woman; all the way up to her perpendicularly extended thumb. “Emily may not play with her cute little butt as much as I know she needs to for a girl her age, but her butt itself certainly remembers the lessons I’ve taught it in the past.” Laura thought as Emily gasped and moaned softly at the intrusion into her most private orifice. With her hand so buried, Laura began rotating it 180 degrees, clockwise and then counterclockwise and back again, inside of her daughter’s ass; trying to get the maximum amount of dilation for the minimum amount of effort. Aloud: “Shhh. Now quite down, baby.” Laura’s hand went through another series of twists and thrusts as her daughter gasped and moaned at the intrusion. “You don’t want to wake up your sister, who’s sleeping so soundly, just because you needed your mother to remind you how to properly treat this little hole of yours.” She reinforced the point by turning her hand towards the bed and pressing firmly downward. Emily gasped as empty black nothingness appeared above Laura’s hand. “Good” Laura thought to herself. “Let’s open this up a little more before we start playing for real.” Emily’s mother placed her left hand on top of her youngest’s pubic mound to hold her steady and then began pulling the no longer overly resistive sphincter in all directions with the four fingers of her right hand already burred into the young orifice. This continued for several moan filled minutes as the loving mother worked her daughter’s pliable hole open wider and wider, quite literally, with a skilled and knowing hand.
In no time at all Laura was able to see at least an inch of spare room above the top her hand no matter which direction she pulled the willing young asshole. Not allowing her daughter to get comfortable with the level of dilation she was already experiencing, Laura quickly folded her thumb over her hand and pressed her fist forward; it quickly disappeared up Emily’s backside with only a soft ‘sluuuurp’ to mark the occasion. Emily was a bit more responsive than her compliant asshole to the situation as she let out a – none too soft – moan of mixed pain and building pleasure. “Emily!” her mother, as quickly and as silently as she could, admonished her daughter. “Mind your volume or I’ll fetch one of your penis gags out of your masturbation kit and mind it for you! And it will neither be a thin or a short one!”
“Sorry, mother.” Emily responded much more quietly, her volume now under control. “I’ll try to – ungh – keep it down.” The chastened teen apologized to her mother under her reproachful glare as the older woman began twisting her now closed fist around the inside of the young woman’s rectum.
“Honestly, Emily. If you would have just taken care of your own hole’s basic needs, I wouldn’t have to be doing it myself at half past the ass crack of early in the morning.” Laura continued, berating her daughter as she moved her first around inside the sloppy hole of her daughter’s ass, ensuring no spot was left unstretched. “You think I don’t have my own needs I could be satisfying right this very instant instead of teaching you how to do something you should know how to do yourself by now?” she continued. Emily, wisely – except for the odd moan and gasp – continued to remain silent as her mother worked her rear hole over to her satisfaction.
A few quiet moan filled minutes of expert motherly fist to daughterly ass lecturing passed into eternity; Laura nodded to herself and slowly withdrew her hand from her daughter’s now quivering anus. “There now; that wasn’t so bad. You should be all nice and stretched out for a proper buggering. Now turn over onto your front, reach back and spread your cheeks so mommy can make you feel good. And I don’t want to hear a word of protest from you, young lady!”
Emily, her aversion to anal all but forgotten in the heat of the moment, didn’t need any further encouragement. She quickly flipped herself over onto her belly, raised her butt invitingly off the bed and spread her shapely legs. Reaching back with both hands to spread her now much looser nether hole open to her mother’s administrations, she lay breathing heavily with her butt slowly and unconsciously rotating in lazy little circles in its anticipation of more attention from her mother.
As Laura picked up the veined dildo she’d selected as she briefly admired her handy work in the now over two and a half inch diameter vortex leading up her daughter’s backside. The pause was only a brief one as she readjusted herself on the bed to rise to her knees and line up the toy with Emily’s needy ass. The change of position momentarily reminded Laura of the presence of her own large toy, safely wedged between her own ass cheeks, as it shifted welcomingly. But it was a momentary distraction as she refocused on the task at hand. With just little forward pressure, the head of the large dildo slipped past Emily’s too tired to resist anus and, inch by satisfying inch, the thick tool made its way unimpeded into her daughter’s moist bowels. All Emily could do was sigh and moan appreciatively as the entire ten inch length of the realistically shaped dildo was sheathed into her pert backside. Seeing any one of her daughters bent over with their butt in the air and a double handed dildo handle protruding from between two young and toned cheeks always gave Laura an internal chuckle. And she’d seen every one of her daughters in that very same position more times than she could ever remember. “Like Arthur and the Sword in the Stone, I’m Laura and the Dildo in the Daughter!” she giggled softly to herself as she did her best impression of her imaginary, heroic self. Single handedly, she grabbed the mythical ‘sword’ and began extracting the ‘blade’ from its ‘rock’, letting it pop free with soft sucking sound. “Proving once again that I’m Queen of the Wilders Bitches!” she proclaimed proudly to herself, smiling at her private fantasy. “Unlike Arthur, though, this ‘sword’ needs to go back into its ‘rock’. And then out again. And then back in yet again. But faster. And with a lot of repetitions.” she continued to herself as the smile on her face disappeared right along with the large faux cock back up her daughter’s still lazily rotating bum. Emily just continued to moan softly – totally unaware of the strange direction her mother’s thoughts had taken – as her bum was subjected to the penetrations of her mother’s unstoppable tool.
Getting serious now, Laura grabbed the handle of the large dildo with both hands, over handed in the way a person from a few centuries ago would have churned butter, and began to pick up the pace. Emily was soon getting her butt truly and properly reamed. The veined toy was being extracted to the point that all but the last inch or two of the three inch wide monster stayed inside her sucking anus and then the remaining eight or nine inches would quickly be rammed back in so deep that the hilt at the base of the dildo made a soft, wet slapping sound as it made contact with her tautly spread cheeks. In fact, ‘churning butter’ wouldn’t be a bad metaphor for the hot and sexy display.
The minutes dragged on and the pounding continued unabated. Emily was now sweating and writhing on the bed unabashedly while she bit down on her sheets and tried not to moan too loudly as she lost herself in the ecstasy that was radiating from her abused bottom. “I just hate it when my mother is right!” she cursed to herself as her previously lost orgasms resurfaced and again began washing over her again. “Awe, fuck it!” she conceded defeat and bit the sheets harder still; the large slab of latex continuing to ravage her pliable, young, rearmost hole.
Laura was sweating too, but from the upper body workout she was getting as she pile drove the three inch thick butt stretcher in and out of her daughter’s sloppy rear end. “I should really be wearing a sports bra” she thought to herself as her massive mammaries swung violently back and forth in cadence to the pounding she was giving her youngest daughter’s neglected rectum. Laura had enough sweat glistening on her toned body now that her large breasts were making a slight slapping sound of their own as they slammed into each other every time she bottomed out in her ungrateful teen’s upturned ass. As her large breasts swayed back and forth, the thumb sized nipples topping each orb were getting a very nice tickling as they rubber across her babydoll chemise and had long since become hard as diamonds. She really wished she had a free hand or two so that she could give the stiff nubs the proper tweaking, pinching and rolling they desired. “You can take care of your own needs later, you horny vixen! Your daughter needs you right now.” She promised herself as she continued the downward thrusting of the thick anal pacifier.
Despite her personal promise of a later reprieve, she’d already gotten quite worked up; Laura could feel her juices freely running down the inside of her thighs. Between the close up and personal view of her sexy teenager’s most private hole being viciously brutalized by a large and relentless tubular intruder and her own renegade nipples being stimulated to the point that they felt like they would soon burst if someone didn’t bite down on them soon – and preferably very hard! – she’d neglected to keep her own well trained bottom clenched down sufficiently enough on the nighttime plug that was situated deep inside her own most private hole. Too late she realized that her stimulated and relaxed sphincter had failed in its job entirely and the huge rectal dilator was slipping past her most intimate defenses; it descended almost a full foot to rest on her daughter’s bed. Laura gasped in unexpected delight as her anus stretched pleasantly around the thick plug’s four and a half inch diameter body. Her sphincter had just been expanded, without her explicit permission, from the mere four inch thick base of the impressive plug. And despite the next best thing to an entire foot of latex toy which now reached from the toned cougar’s widely stretched butt cheeks to the sheets of her daughter’s bed below, nearly as much of the thick bitch tamer still remained deep inside of Laura’s suddenly grasping ass as what had accidentally slipped out.
“Damn it!” she quietly cursed to herself, trying not to interrupt the sawing rhythm of the – now, relatively appearing, very much smaller– toy into Emily’s orgasming, upturned ass. If Emily had noticed her mother’s soft outburst she gave no hint of it; lost in the waves of anal orgasm that she was. Laura bit her lip in consternation as she tried to decide what to do; a half inserted butt plug was a distracting quandary, no matter what its actual size was. As quickly as the indecision came her mind, her body made its own decision; which Laura discovered a few seconds later as she finally noticed that her hips had already began to ride up and down on the smooth shaft piercing her cheeks. “Oh God yes!” she hissed to herself, throwing her head back in pleasure. She intentionally picked up the pace of her hips, needing to abuse her own needy hole more than ever now.
Despite the sheer size of the massive plug stretching her humble bottom, which was now being driven into the horny mother’s ass by her very own body weight, the fact remained that it was still just a smooth nighttime plug designed for comfortable, long duration wear; it wasn’t textured for short term pleasure. Laura soon groaned to herself in resignation to that fact. There was no way this was going to get her off. All this was doing was frustrating her still further and increasing her already running at full steam libido. “At least I don’t have to keep this up much longer” Laura commented to herself as she noticed that her daughter’s steadily building orgasm had hit its earth shattering climax. The younger woman suddenly went rigid and flattened herself on the bed below, emitting a muffled scream into the mattress. Laura immediately changed the challenging rhythm of the ten inch invader which was punishing Emily’s tightly clenching bottom to a different one designed to push Emily’s already strong orgasm just a little bit farther. She slowly withdrew veined tool to the halfway point and quickly, and much more forcefully, thrust it inwards as hard a she could; trying to burry every fraction of an inch into the teenager’s spasming butt. Emily only grunted between her otherwise continuous screams as the three inch thick daughter tamer slammed into her quivering anal ring so hard it shoved her forward an inch or so with each thrust.
Again and again the skillfully employed toy slammed into Emily’s barely coping sphincter. Again and again Emily grunted against her screaming, continuous orgasms as she was forced forward inch after inch by the forceful impact of firm, unyielding latex against the supple and all too yielding teenage flesh of her no longer resisting ass. Finally, totally spent, Emily went limp on her bed as her mother ceased the savage assault on her helpless back hole. All she could do was lay there and gasp for air and try and regain her senses.
Laura, also breathing hard, but for an entirely different and unsatisfying reason, leaned back on her heels to get some much needed air. The humongous plug resting on the bed beneath her slid still further up her butt as she did so, eliciting as soft sigh of desire from her lips. Quickly refocusing on her daughter she asked “See there? That’s what your body needed. Not that silly thing you were doing to yourself when I came in here half an hour ago.” she said reassuringly to her daughter as she leaned forward to softly squeeze and caress the cheeks of her daughter’s still fully packed ass. The double handed handle sticking out between her daughter’s pert butt cheeks was once again all that was visible of the ten inch toy. All Emily could manage in response was a jerky nod of agreement as her voice was still beyond her ability to control. Laura continued to massage her daughter’s firm butt cheeks for a moment or two, enjoying how her manipulations of Emily’s derriere caused the latex handle to flop tantalizingly this way and that, then lovingly patted her daughter on the rear and sat back up again. Reaching between her dripping pussy lips to the thick, smooth plug beyond, Laura grabbed hold of the base and began reinserting the entire length into her horny back passage until her sphincter closed around the four inch thick base, against its will, once again. Forcing it to accept a smaller diameter toy than it had inadvertently grown used to was not something she desired at this moment either. Her slutty, insatiable, rear hole demanded something larger, and with a pleasing texture; and she knew it. A demand she intended to placate as soon as she finished with the maternal nurturing her daughter currently required of her and she was able to return to her own room; and her own waiting masturbation kit with its considerably larger weapons of ass destruction.
Laura stood up slowly, allowing her muscles to acclimate to the new, vertical position. She walked over to her daughter’s masturbation kit and selected a smallish, for her at least, butt plug that was two and three quarter inches at the base, three and a quarter inches in diameter for most of its body and about eight inches in length overall. Returning to her daughter’s side she bent over and slowly extracted the ten inch toy already nestled inside the teenager’s backside, causing Emily to moan in disappointment at the sudden feeling of emptiness. Quickly before the, considerably larger than previous, gaping hole could even begin to consider attempting to close, Laura lined the slightly thicker plug up with it and pressed inwards. Emily began to groan softly as the plug met with all the brief, pitiful resistance her battered anus could muster. That didn’t last long at all and the plug quickly slipped past Emily’s sore, ever expanding sphincter; eliciting a slight ‘yip’ from the young woman. It finally came to rest against the moistened ring of the forcefully loosened muscle; a ring of muscle that Laura had now made her personal mission in life to retrain in the ways of proper behavior.
Laura moved up to the head of the bed, rolling her daughter over onto her back as she went, in order to face her directly. “There. Now that is a much more reasonably sized plug to be wearing to bed for a girl your age. We’ll work your butt up to something larger in the next few days.” Laura reassured her daughter as she cupped the young woman’s face in her hand. “I’m sorry I was so forceful with you earlier, but it was for your own good; you know that, don’t you.”
“Yes, mom” Emily replied, reaching up with her own hand to hold her mother’s wrist. “I’m sorry I was masturbating wrong in the first place.” She half lied. She really hadn’t desired tonight’s lesson but was glad for it now that it’d happened. The considerably larger plug wedged between her cheeks was uncomfortably wide but it felt good and proper in the afterglow of such a powerful anal orgasm.
“I’m glad to hear that, Emily.” Her mother replied. Handing the glistening phallus to her daughter, “now be sure to clean up your toys and put them back where they belong before you go back to sleep or we’ll have to add a spanking to your punishment first thing in the morning; and I know how much 18 year old girls hate to be spanked by their over bearing mothers!” she quietly half hinted, but with an underlying tone of complete certainty about the spanking if her orders weren’t carried out to the letter. She routinely warmed the bottoms of her daughters when they got disrespectful or too lack-some; like skipping out on their full allotment of cleansing enemas. Cleanliness is next to Godliness, after all.
Emily took the sizable toy, which had until very recently been plowing into her unprotected rear end, from her mother and hugged it between her perky breasts with both arms like it was her cherished, girlhood teddy bear. “I will mom. Promise!” she whispered in response.
“Good girl.” Her mother said proudly, bending down to kiss her youngest goodnight. It was a passionate, lingering kiss. A proper mother/daughter kiss. And as their tongues met, Laura’s hand wandered down between her daughter’s slender legs to the moist pussy between. She easily slipped two fingers into the post orgasmic slime she found there and worked their way around the inside of her daughter’s front hole; it was the first time she’d touched that part of her daughter’s anatomy this morning. In no time at all, the fingers were coated thoroughly with Emily’s juices. While Laura was fingering her daughter, Emily’s hand had found her mother’s leg at the knee and had quickly navigated up the thigh to the dripping pussy at its apex. Emily’s own two fingers had just as easily sunk into her mother’s horny cunt and soon became drenched in the older woman’s horny juices.
After a minute or so of hungry tonguing, Laura broke off the kiss with her daughter as four very wet fingers extracted themselves from two equally wet pussies. As if in unison, both women reached their dripping fingers up to the other’s waiting mouth, which eagerly opened to greedily suck the offered digits clean. It was a practiced maneuver for Laura and her daughters; as it was for most close, female relatives in proper, conservative families. The exchange of pussy juice in this fashion was a common way for mothers and daughters to say good night to each other; once the daughter was of age and had started her anal training of course. Laura had always insisted her and her daughters say good night to each other in this way ever since each one of them had reached the proper age. After all, sucking your own juices off of the offered fingers of a loved one was always a great trust building exercise.
After they had finished sucking the other’s fingers clean, Laura started to stand back up, but allowed her hand to drift back down to her daughter’s gushing slit to go finger diving for a second time; this usually wasn’t part of the normal routine but Laura wanted some of the teenager’s succulent juice to go and Emily was in no mood to argue. “Alright, I’m headed back to bed. You get a good night’s sleep and I’ll wake you in the morning.” She said as her third finger joined the previous two and slipped into her daughter’s drenched pussy to scoop out as much of the sweet girl cum as she could. Emily only inhaled sharply and hugged the veined dildo to her chest harder with both arms, which caused her breasts mould themselves around the thick shaft in a very pleasing manner. Her mother continued to harvest Emily’s juices for a few more moments as enjoyed the view of the supple breasts rising and falling in time with the young woman’s steady breathing. “I love you, honey” her mother said, reluctantly removing her fingers and then bringing them up to her hungry lips.
“I love you to, mom.” Emily said, finally devoid of her mother’s questing fingers and with the early stages of horniness returning.
Laura smiled sweetly to her daughter and turned to leave as she tasted her juice soaked fingers. She moaned softly as the taste of her daughter’s anal induced orgasms filled her mouth; closing her eyes in bliss. At the doorway to the bedroom, since of course there was no actual door, she turned to quickly wave goodnight to her youngest daughter a final time, not interrupting her fervent finger sucking in the process. She briefly noticed Cora still fast asleep, and blissfully unaware of what had just come to pass mere feet from her person, and smiled to herself. “Cora will be pissed as Hell in the morning when she finds out what I did to Emily; and that she didn’t get to play too.” Laura thought to herself as she turned and headed towards the master-less master bedroom, still relishing her Emily flavored fingers. “Cora really loves the taste of Emily after a really hard orgasm more than the taste of any of her other sisters; more than the taste of her mother even! I don’t know how I’ll ever make this up to her” Laura continued as she walked down the hallway. “I’m sure I’ll come up with something” she reassured herself. But for now, there was a satisfyingly over-sized, veined dildo just waiting to ravage her own very hungry asshole just around the next corner. Her free hand moved up to her hard nipples to give them the attention then demanded as well as she made her way towards her own impending anal induced orgasms. “It’s always such a rewarding experience teaching proper masturbation!” Laura concluded as she disappeared down the hall.
Minutes later, the soft sounds of wet slapping – emanating from an exquisitely trained asshole sparring against a latex juggernaut that was utterly unimpressed with its opponent – and deep, satisfied moans began drifting back down that same hall. The sounds continued for the better part of the next hour before all was quiet again inside the Wilder home.
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