A Proper Young Woman’s Guide to Anal Etiquette Ch. 01

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A Proper Young Woman’s Guide to Anal Etiquette:


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.


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 canlı bahis 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 bahis siteleri 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 bahis şirketleri 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.

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