A Proper Young Woman’s Guide to Anal Etiquette Ch. 03

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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. If I can’t stop you I can at least make sure you’re doing it right. Consider yourself disclaimed.


After School Special

“What a day!” eighteen year old Emily exclaimed as she dropped her purple backpack onto the bedroom floor and flopped backwards onto her bed. She was still wearing her school clothes from the day: a somewhat tight yellow T-shirt that hugged her young breasts invitingly and a pair of tight jeans that showed off the contours of her firm ass even more so.

“I don’t know what was worse. Mrs. Perkins popping a history quiz on us with no warning or spending the entire day with this huge fucking toy up my butt!” Emily continued in an overly dramatic voice. “I mean, didn’t they outlaw pop quizzes back in the 20th century? Certainly in the first half of the 21st century,” she amended. “And why do we need to know who did what in Renaissance Europe anyway? It’s not like that knowledge has any practical application. Even if it did, wouldn’t we have the internet right there to answer it for us!

“And this plug! It’s too big for me to wear around! It was all I could do to walk around looking normal so I didn’t embarrass myself with nine inches of latex buried up my ass!” she finished tartly.

“Oh, quit being such a drama queen!” Cora answered sternly as she sprawled out to relax on her own bed on the other side of their shared bedroom. She still wore her crimson and white cheerleading outfit that she’d changed into after school for practice. The outfit was pretty straight forward and traditional consisting of a cleavage enhancing halter-top, bare midriff and pleated miniskirt.

“Obviously, no one gave Mrs. Perkins the memo about pop quizzes; assuming you’re right about them being outlawed in the first place. Although, judging by your score on the quiz, I wouldn’t have too much confidence in your recollection of history!”

“Shut up, bitch! At least I passed!” Emily retorted.

“Hey! That’s not nice,” Cora said. “I wasn’t arguing with you. I’m just saying you didn’t do too good yourself,” she continued, defending herself. “And quit complaining about your plug. That pathetic little sphincter of yours is only being stretched out by what? A three inch neck? Please, sis! Mom packed me with one a full inch wider in diameter. And I had to go to cheerleading practice wearing it!” Cora exclaimed. “Try doing high kicks, jumps and generally dancing around with something the size of a fat guy’s forearm buried up your ass and get back to me!” she finished.

“Yeah right,” Emily responded. “It’s not all that much larger than the plugs you normally wear to school. I usually wear something half this size and I’m just not used to it,” she concluded. Emily brought her hands down to abdomen and pushed her fingers gently into her firm belly. It didn’t take long for her to identify the hard outline of the invading phallus buried deep within her colon. She could even get it to move from side to side as she alternated applying pressure to the left and then the right. The sensation felt strange yet oddly stimulating.

“Well you’d better get used to it.” Cora said glancing over at her younger sister and watching her play with her abdomen. “I think mom has discovered a new found interest in that tiny little back door of yours. I wouldn’t be surprised if you find yourself up to four inch plugs by next week. Maybe even five inch plugs by the end of the month!” she said evilly.

“Anything bigger than this and I’ll have to start wearing a small corset just to keep it from being obvious to anyone looking at me.” Emily complained. “I’m pretty sure, even with this one, half the people at school knew what I was wearing today just by the abnormal bulge in my tummy!”

“Bullshit!” Cora responded. “Most of the people in school already wear a larger plug than that on a daily basis. Everybody who doesn’t is a guy and don’t have to wear plugs to begin with!” she concluded; laughing at her own little joke about the differences between the sexes.

“Ha. Ha. Very funny. But not every girl at school comes from a family as conservative as ours is. I know a few of my friends don’t have a proper upbringing at all and are actually still virgins back there! If you can believe that! In this day and age! And they never even had as much as a finger or a tongue up almanbahis şikayet their bung holes!” Emily exclaimed.

“I know,” Cora agreed. “What are their mothers thinking? What’s going to happen when they get into a serious relationship and their partner wants to have a little harmless anal fun and comes to find out they can’t even get a simple dick up there without a bunch of screaming and whining involved! I mean, I wouldn’t have kept my first real boyfriend very long if I couldn’t have taken his fist up my ass while I took his dick down my throat every day after school. I just don’t see how some women plan on being successful as a person in life if their ass never learned to how to gobble up whatever it gets offered!

“And what did you think you think those waist cinchers grandma gave you last Christmas were for?” Cora continued. “She obviously expected you to be wearing four inch dilators regularly by now too.”

“I just think our family takes it a little bit too far,” Emily came back. “Even most girls with a proper upbringing aren’t stretched to the extremes that mom and dad put Amanda, Mary, and Naomi through; or that mom put us through after dad died.”

“Well, from what I’ve heard from our older sisters, mom actually takes it pretty easy on us compared to what she put them through. She had to be a lot stricter with them because dad was still around to keep mom’s own back hole on a regular diet of thick latex cock. I know you’ve noticed as much as I have that the size of the toys mom masturbates with at night has slowly shrunk over the past year or so. She’s gotten out of the habit of having the strict discipline of dad to keep her bottom properly dilated. I talked to Naomi at breakfast and she told me mom actually had trouble taking a five and a half inch punishment plug this morning! Can you believe it! Our mom, Laura the Great Gaping Anal Queen, was grunting in pain from a five and a half inch plug! Dad would never have let mom digress to such a point if he were still around.”

“Yea. I know,” Emily admitted. “Although, if dad were still around, you’d probably be up to at least a five inch dilator for your everyday plug.”

“Yup. And you’d be maybe half an inch behind me,” Cora concluded and watched Emily wince at the thought.

They allowed the conversation to die, as each young woman contemplated the severe anal training that should have rightfully been theirs had modern medicine been better up to the task of emergency cardiac treatment. But technological wonders could only go so far.

Finally, Cora shivered to banish the sad memories and brought her mind back to the present and happier times. She rolled over onto her side to face her sister, who was still playing with the shape of the hard latex through her yellow T-shirt. Propping her head up with one hand, Cora reached back with her other to the base of the thick training plug wedged up her back hole. Wrapping her hands around what little extended out of her body she began to pull the firmly embedded latex out through her stretched anal ring. She had to bite her lip to keep from moaning in mixed pain and pleasure as the four inch neck gave way to the four and a quarter inch body of the ten plus inch long anal plug. Wanting to savor the extraction, Cora pulled the thick toy out as slowly as she could; savoring the sensation of having her anus temporarily pulled inside out as it resisted the extraction of the huge torpedo shaped toy.

Finally, she felt the plug slip free without so much as a pop; actually, it was more of a soft, wet slurp. Cora knew well from past experience that her ass had been utterly defeated during the course of the long day of relentless stretching by the thick plug. She doubted her nether hole had closed up much smaller than three and three quarter inches in diameter after it’d been freed from the iron heel of latex tyranny; barely smaller than the size of the plug’s neck which had spent the day teaching her sphincter its proper dimensions. A lesson her tired and sore muscle ring had learned very well. She knew it’d be hours before her anus returned to its normal unused gape of around an inch and a half. Like all women with a proper upbringing, a fully closed and self sealing asshole was a physical impossibility long before the twentieth birthday. Without the constant aid of latex tools, the vast majority of the female population of planet Earth would simply have shit running down their legs most of the day. It wasn’t called a butt “plug” for nothing!

In fact, while it still wasn’t polite to discuss the common practice of female anal dilation in public, society had quietly adjusted to its new norm. Women’s bathrooms were typically twice or three times the size as they would have been around the turn of the 21st century. This was because every stall was also equipped with enema facilities. When most women’s lower intestines were basically filled with rubber for most of the day, colonic cleansings every few hours were an almanbahis canlı casino anatomical necessity. Cora herself had administered three flushes during the course of the day, just to keep the pressure of her excrement at a comfortable level. Of course, the larger and more filling the plug, the more frequent enemas were required. Bearing that in mind, she estimated Emily probably only had to give herself two during the school day. She wondered how many trips to the bathroom their mother had to take on a daily basis just to keep herself cleaned out. A lot more than Cora herself, that was for certain; even with the smaller plugs her mother normally wore to work these days.

Finally, Cora spoke up. “You know, for all your bitching about that silly little plug you’ve got up your bony butt, you seem to be perfectly content laying there with it in and playing with it through your shirt. I think you secretly love it up there!”

Emily immediately stopped her playful manipulation of the toy through her stomach and glared angrily over at her older sibling. Cora simply glanced up at the ceiling as innocently as possible as she began tongue washing her significantly larger plug that had, until seconds before, been stretching the cheerleader’s sexy bubble butt. Emily opened her mouth to say something angry in response but there was nothing she could say. So she snapped her mouth shut and simply began unbuttoning her tight jeans and shimmying the faded blue denim off her shapely hips.

Cora watched Emily gyrate her hips to free herself from the skin tight denim with interest. As expected, Emily wore no panties under her pants. Once the fabric was free of the younger girl’s hips, Emily lifted her legs up to slip the trousers off; and Cora made her move.

With the grace of years of gymnastics and cheerleading training, Cora was at her younger sister’s bedside instantly. With her free hand, Cora grabbed hold of the jeans just as they were bunched up around Emily’s ankles and held them fast. At the same time, she used her superior position over her prone sister to push the legs down and back. The result was the most beautiful scene in the world as far as Cora was concerned. The repositioning of Emily’s legs caused the wet and puffy lips of the pussy at their apex to spread invitingly; the delicious pink girl flesh they’d previously hidden underneath revealed to Cora’s gaze at last. And, mere inches below that delectable front hole, was Emily’s painfully filled nether hole. All that was actually visible, of course, was the base of the thick plug that had spent all day violating her younger sister’s tender rectum. But it was framed by one of the most attractive pairs of ass cheeks Cora had the pleasure of daily sinking her face between; it certainly wasn’t the only one. She had managed to lose her panties, again, in the locker room after cheerleading practice after all. But that’s a story for another day.

Cora paused half a second to admire the soft white skin of her sister’s ass framing the large circle of black latex between them, and topped off with moist pink pussy lips before Emily was able to jerk her legs in protest.

“Hey!” Emily growled. “Just let me get this plug out first. My ass is really sore!”

“I’m here to help, sis,” Cora replied, “just hold this and I’ll get it out for you,” she said as she handed her own dirty plug between the two raised and spread teenage legs to her sister below. Emily barely had time to think about the unwanted offering as she accepted it without immediate protest. “Let’s just take a look at this tiny plug you’ve got here,” Cora continued as she squatted down at the base of Emily’s bed; being mindful to keep the legs spread high and wide.

“I’m perfectly capable of pulling it out myself, thank you very much,” Emily finally managed to get out. “Now let go of my legs so I can finished getting undressed and get this thing out of me!” she said angrily.

“Nonsense!” Cora responded. “Remember what mother always says: ‘When it comes to butt plugs, always ask for help,'” she quoted. Cora used the pause to sink three fingers of her unoccupied hand into the dripping snatch of her favorite sister. She was pleased to hear a soft, if very firmly restrained, moan of desire escape the lips of the restrained girl lying on the bed. Cora used her thumb to manipulate the little man in the boat as she worked the three digits all around the now soaking wet hole, causing soft slurping sounds to fill the small bedroom.

“Mother does NOT say that!” Emily protested. She tried to squirm away from the invading fingers in an attempt to escape. The attempt, she realized with a sudden sinking feeling, was only half hearted as her body betrayed her yet again. “Damn it!” Emily yelled silently at her body as it submitted to her older sister’s dominant mannerisms. “You’re my body! Listen to me!”

Her body’s only answer to her silent command was to start to slowly rotate its hips in time with Cora’s questing almanbahis casino fingers.

“God damn it!” Emily said softly out loud. It was meant to be a silent curse.

“Such language from someone I’m only trying to help!” Cora said while managing, with great success, to sound offended. “And while I’m helping you out with your butt problem, why don’t you do something constructive with that naughty tongue of yours. I’m sure you remember what mother always says about dirty plugs in her house!” She glared down at her younger sister, fingers still working the soaked pussy, until Emily brought Cora’s dirty plug to her lips and began washing the day’s stains off with her tongue. “That’s better. Now be a good little girl and shut your fucking worthless mouth hole while I deal with your two needy holes that are actually good for something!”

Cora’s coarse language would have been offensive to anyone else who might have heard it; certainly their mother would have had a fit if she’d heard Cora talk that way to her sister. Emily was used to it though; it was all part of their sisterly banter.

With that shockingly derogatory statement verbalized, Cora bowed over Emily’s bent-in-two form, bringing her lips in contact with the hot pussy that she’d been playing with. Emily moaned out load; no longer attempting to hide her desire. Removing her fingers from the wet cunt, Cora buried her face into the delicious folds of her sister’s pink flesh; savoring the taste of the succulent young pussy juice like a starving man savors a fine steak. Sucking the labia into her mouth, Cora used her tongue to clean them off as best she could before allowing them to slip out again. Only then did she dive her tongue into the wet hole that was the source of all Emily’s delicious nectar.

All Emily could do was resign herself to her body’s desires and enjoy the sensations that her sister was giving her with that talented tongue of hers. For her part, Emily did her best to clean all the lubricant and slime that had built up on her sister’s plug throughout the day, but she was having a hard time with the task, with all the undignified moaning she was emitting.

Cora spent a few minutes devouring her favorite pussy in the world before moving her free hand down to the ebony disk parting her sister’s lovely ass cheeks. Although Cora normally referred to Emily’s backside as ‘bony’ out loud, she actually found it to be quite attractive. Grabbing a hold of the base, she began to firmly pull it outward. She encountered only moderate resistance as the three inch diameter of the plug’s base quickly grew to the three and a half inch wide mass of the toy’s main body. Emily’s low moaning and hip gyrations were only momentarily interrupted by a quick intake of breath as the increased thickness stretched her tenderized back hole wider than it wanted to be. But just as Cora’s own hole had learned well the day’s lesson on appropriate size, Cora found Emily’s nether hole to be an equally adept student in forced dilation. Nine slow inches later, and with minimal fuss, a wet slurping noise that matched Cora’s earlier one announced the plug sliding free of Emily’s now gaping anus.

Cora paused a moment in her snack of teenage snatch to admire the three inch dark pink cave that had magically appeared between her sister’s wonderfully toned ass cheeks. She could see the well-trained muscles of her sister’s sphincter trying to close the wet hole, but the attempt was less than futile. Just as Cora’s own distended bottom opening was still gaping wide — and she could feel air passing into and out of her colon with each breath she took — Emily’s ass would remain a wide open fissure for hours before it returned to its smallest unused state. Although, while Cora’s own normal gape was a respectable inch and a half, Emily’s anus at rest barely gaped an inch or so. For a member of the Wilder household, that lack of sustained anal dilation should have embarrassed her younger sister no end. As it was, Emily seemed to be content with her lack of anal self control. Cora would never understand some portions of her sister’s psyche.

The older sister could have sat there and just stared at that beautify glistening pussy and gaping ass for hours, but she didn’t want Emily to lose her focus and decide against, with actual sincerity, some sisterly after school fun. With only the slightest hint of regret, she returned her tongue’s attention to her sister’s front fuck port while returning the thick plug to its rightful place up her back one. Emily both grunted and gasped at the combined sexual assaults on her non-resisting holes. Which assault elicited the grunt and which the gasp, neither sister much cared.

With only minimal resistance, the thick butt stretcher slid back into its young, rectal sheath. Once at the halfway point, Cora stopped and began to twist and turn the latex toy this way and that in Emily’s distended anus; reinforcing today’s hard learned lesson in the proper shape a young woman’s asshole should always take. Not moving the butt plug more than a few inches in either direction, Cora continued to manipulate her sister’s tender sphincter with the plug in her free hand while her lips and tongue had their way with Emily’s spasming pussy.

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