A Proper Young Woman's Guide to Anal Etiquette Ch. 06

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An average evening at the Wilder's: No ass left unstretched.
10.3k words
4.51
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Part 7 of the 13 part series

Updated 06/08/2023
Created 09/08/2012
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lordodie
lordodie
840 Followers

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.

Wilder Evenings

Once again, Cora and Emily are reclining on their beds discussing their days with each other. As would be expected, Cora is dressed in her normal cheerleader's uniform, which consists of a tight halter-top and a short, pleated skirt. The mere sight of the eighteen-year-old's large 34D breasts packed into such a tight top, and her amazingly tight ass, would give any teenager - male or female - wet dreams.

On the other side of the room Cora's sister, Emily, is dressed in a formfitting dark blue sweater and light denim shorts. While Emily's unbelievably perky 32B breasts were much smaller than her sister's, on her noticeably more petite frame they actually look very inviting as they strain to break free from the sweater's thin material.

As both girls laid back on their beds, their conversation was centered around the slight bulges in their midsections; Cora's tummy was uncovered due to her cheerleader's outfit while Emily had her sweater bunched up under her small tits.

"And today was worse than yesterday!" Emily continued in dismay. "I mean look at my tummy!" she said, as she poked at the slightly noticeable outline of the three and a quarter inch wide, twelve inch long dilator plug which their sister Amanda had fitted her with that morning after the family's enemas.

"Well, you didn't have to wear that tight sweater after she buckled that thing up that small back door of yours, now did you," Cora responded as she played with the more noticeable bulge of the four and a quarter inch wide, thirteen inch thick dilator plug their older sister had decided to shove up her own asshole. "I'm kind of screwed with this outfit - as I didn't really have a choice - but you could have changed clothes."

"Mom said I looked cute in this! And we didn't have the time anyway. We got rushed into the car too quickly after our plug fitting for me to have run back to the room and changed. And besides, Matt said I look sexy as hell in tight sweaters. I need to make sure I keep him interested in me before our first date on Saturday."

"Ah... So now it all makes sense! You're just trying to show off to our very own swim team captain!" Cora said teasingly. "You'd better pick up the pace of your training. He's from a very conservative family who believes in proper family values. I doubt his mother would let him date a girl who bitches so much about a silly little three inch anal plug!"

"Shut up, slut!" Emily shot back, "And it's three and a quarter inches thick, thank you very much! Besides, I doubt his mother would be validating my anal training on our first date anyway. It's not like we're getting engaged."

"I wouldn't be so sure. I have gym with his twin sister, Sybil. You should see the sizes of the plugs her mother fits her with! They're huge!" Cora said as she made a circle with her hands that was at least seven inches across. "She already has to wear waist cinchers just so she doesn't cause a scene anywhere she goes. In the shower after gym, it's easy to see why.

"How was gym class with your plug today anyway?"

"It was horrible! Mrs. Schneider had us doing jumping jacks and jump rope all period! I swear to god it was less for our physical fitness and more so she could watch our tits bounce for an hour!" Emily said with distaste. "And I almost came half a dozen times because of all the jumping around. It was like this stupid plug was fucking me silly every time I moved!"

"Maybe that was her plan too?" Cora wondered. "I've seen Mrs. Schneider work a class of seniors so hard that a few of the girls actually did cum from the workout. How embarrassing would that be? Of course, it was all passed off as being out of breath from the strenuous calisthenics, but people know what it sounds like when a woman cums hard; just spending five minutes on the internet will teach anyone that much!"

"Did she get in trouble for embarrassing her students like that?"

"I heard she was reprimanded for it, but that's about it."

"Well, that's stupid! Steven Miller was expelled just last week for getting his girlfriend off in English class. And the gym teacher goes free with just a warning? How is that fair?" Emily asked angrily.

"Dunno. That how it works. I guess if you 'accidently' get a student to cum during gym that's one thing. If you make your girlfriend cum in the back of class because you're fucking her with her own unbuckled butt plug while the teacher's lecturing, that's another.

"Stacey is a whore for letting him do it anyway. I mean, come on! In public?! I wonder what her mother said afterwards. I know what our mother would say.

"And it wouldn't be anything good!" Cora concluded matter-of-factly.

Emily shuddered at the very thought. "She raised us better than that. I'd let Matt play with my plug in a dark theater - maybe - but certainly not in school. That's just horribly uncivilized!"

"Well, we were raised properly," Cora agreed.

"Speaking of English class," Emily said, changing the subject, "Missy and I were talking before my third period composition and rhetoric class. She told me about the lesson the she got from her mother last night. It actually sounds pretty fun; you interested?" the younger eighteen-year-old asked with hopeful enthusiasm.

"Depends," Cora responded hesitantly. "I assume one of us has to play the bottom?"

"Well, yeah!" Emily said with her best Valley-Girl impression.

"You up for a switch when you're done?"

"Of course!"

"Then I'm all for it!"

Emily giggled. "But you haven't even heard what her lesson was about. How can you be all for it?"

"Babe, Missy and I share study hall together; I've heard quite a few stories of what her mother does to her for her training. If what you have in mind is anything like the perverted shit I've heard come out of that girl's mouth, then I'm all for it."

"Well, okay then," Emily said as she stood up and began taking her shorts off. "Strip from the waist. We can't very well do anything perverse with your holes protected by your cheerleader's bottoms, now can we?"

"Nope," Cora agreed as she began unbuttoning her pleated skirt, "I actually think my holes have been far too protected all day!"

Lifting her hips up, Cora wiggled out of the small skirt and then raised her legs straight up to remove them completely. At that point, her legs were intercepted by Emily who finished removing the garment for her. Without letting go, Emily lowered Cora's legs down and sideways; positioning her slightly older sister on her side with her bum pointed straight out. With her sister so positioned, she began unbuckling the strap to the four and a quarter inch dilator plug trapped inside her sister's nether hole.

Cora giggled at her sister's unexpected assertiveness. "Nice, Emily. When did you become such a proficient sadist?"

"When I'm horny and my sister is looking so hot in her cheerleader's outfit, that's when!" answered Emily.

"But I'm usually wearing this and you're always horny, so that doesn't make any sense!" replied Cora as her sister finished unbuckling the large anal violator and began extracting the smooth thirteen inch toy from her pert backside. Cora only moaned at its passage as her own arousal peaked. "Could it have anything to do with your own - very recent - rediscovery of that tiny, barely-fucked-hole you call an asshole?" she said tauntingly.

"Why don't you just shut up and put that mouth of yours to work on something useful," Emily demanded as she handed her sister the recently freed - and slightly dirty - plug. Obediently, Cora took the thick tool and began washing its circumference with her tongue.

With her sister silenced for now, Emily stopped to admire the gaping hole between her lovely sister's athletic bubble butt. Her mouth salivated at the beautiful sight. Licking her lips, Emily quickly pulled Cora's masturbation kit out from underneath her bed and began rummaging through it for the supplies she'd need. She knew her sister would love what she had in mind. Her own pussy was practically gushing with anticipation. In fact, she was so hot with the scheme of what she had in store for Cora that she hadn't even bothered to remove her shoes or the sizable dilation dildo from her own sore backside.

In fact, the only thing that excited her more than the torment that she was about to inflict on her favorite sister was the knowledge that she was next.

Or maybe it was the fact that Cora would be the one to do the inflicting.

Slightly confused by the blurred distinction, Emily - undeterred - went about her business of preparing the torment that both of them would soon be enduring.

***

A little while later, Laura and Amanda arrived home at the Wilder domicile after their respective long days at work. After Laura parked her car, they walked through the garage's inner door into the large and well equipped kitchen. "God! What a day!" Amanda exclaimed as she arched her back and stretched; her massive tit meat straining against the expensively tailored little black dress as she did so.

Laura's eyes hungrily admired the swell of mammaries straining against their restrictive fabric as she watched her eldest daughter work some of the day's stress out. Laura's day at the Too Big To Fail Investment Bank had been a long and frustrating one. She'd forgotten how much harder it was to go though the day with an 'appropriately sized' daily plug locked inside her butt. She'd become far too accustomed to ones that were 'just big enough'.

"You're telling me! It's been a long time since I've worn something so large for so long," the mother of five commented as she unconsciously massaged her sore bottom through her equally expensively tailored business suit's skirt. "Beverly - you know my boss - kept asking me what was wrong as I fidgeted all morning during the board meeting. I finally had to tell her that I was suffering from a little rectal fever, but that I was okay."

"Hehe. And what did she say to that?" Amanda inquired as she continued to rub the knots out of the small of her back.

"She only smiled and told me not to worry about it. 'I see. That's been going around lately', she said. Come to think of it, she was out sick for three days last week with the same thing. Actually, she's still moving around a little slowly. I don't think she's fully over it yet to be honest," Laura said with her own smile. Beverly had confided in her last week that her husband had finally opened up her rear hole enough to get the next size plug to fully seat. Much to the forty-eight year old executive's distress, her husband had increased the size of her daily plug along with it.

Beverly had been Laura's boss at TBTF for nearly half of the twenty years she'd worked there. Accordingly, the women had quite a close working relationship. After all, when Laura had first started with the company at the tender age of twenty-six, she'd been Beverly's secretary. Back then, the two had enjoyed a near identical relationship to the one Laura and her own secretary, Tanya, did now. In fact, Beverly still had the keys to all the padlocks Laura's used to secure her daily plugs - a gift from Laura's late husband Dave at a Christmas partly long since forgotten. Because of that, Laura knew what she was in for when the hour and a half long lunch meeting invite popped up on her calendar shortly after the board meeting had ended. That meeting ended up being a major contributor to Laura's sore butt that she continued to massage through her skirt.

Beverly had politely explained that she needed to look out for the wellbeing of her best account manager, and the best way to do that was to ensure that her new butt plug was properly seated. It took the slightly older woman nearly half an hour just to ensure the gigantic fake phallus was situated perfectly inside Laura's overstretched rectum. Of course, that was after the half hour of Laura bent over her boss's desk with her skirt hiked up, hands spreading her cheeks apart, while Beverly worked the five and three quarter inch monster with vicious enthusiasm in and out of her spasming anus.

Beverly's own three daughters had grown up and moved out years ago, but her maternal instincts remained as strong as ever. Mostly, those instincts were focused on her well trained twenty-three year old secretary, Alyssa. Occasionally, however, her ex-secretary, Senior Account Manager Laura Wilder, found herself at their center.

During the course of the lunch meeting, the older woman's maternal instincts weren't finally sated until Laura had cum over a dozen times from the expert manipulation of her strained nether hole.

"But enough about my day, how was the Expo, honey?" Laura asked her daughter as she dropped her purse onto the kitchen counter and bent down to take off her five inch heals; knowing full well that the position gave Amanda a spectacular view of her upturned ass.

"It went well enough," Amanda replied as she admired her mother's muscular ass cheeks and the long legs beneath the conservative mid-thigh length skirt. "Today was really just a warm up for tomorrow; that's when the bulk of the convention's participants will be there. I actually never had to personally demonstrate a single thing all day! My girls did their jobs perfectly."

Amanda was truly very proud of her half dozen temporary employees. The GirlSupply modeling agency had provided Anal By Design a variety of twenty-something booth girls to showcase and demonstrate her company's wares to prospective customers. Despite a steady flow of people through her stall, there was always an eager booth girl waiting to be of service. More precisely, there was always a booth girl's eager nether hole to be of service. Amanda had no doubt that tomorrow would be different though; her own back orifice was likely to get quite the workout.

"I did bring home a few new items from our spring catalog that I'm sure you and the girls will really appreciate though," Amanda said mischievously and motioned towards the large gym bag she'd dropped just inside the door.

"Oooo! My heart's a-flutter!" Laura exclaimed as she stood up, after having freed her feet from her Italian leather high heels. "Something for tonight or something for tomorrow morning's plug fitting? This morning's session caught us all by surprise, by the way."

Earlier that morning, after the family's morning enemas, Amanda had insisted that her mother and two youngest siblings be fitted with dilator plugs that were very nearly their maximum capacity. In Emily and Cora's case, Amanda told them that if she had to spend the night stretched to her new five and five eighths inch maximum capacity by the dildo locked up her aching bottom, the two over-eager teenagers could go through the day wearing three and a quarter inch and four and a quarter inch butt stretchers; Emily's selected toy was twelve inches long while her sisters was thirteen inches. The two youngsters couldn't argue her logic and had only moaned softly as their oldest sister inserted the two sizable toys into the pair's pliable anuses. Their dildo straps were then tightly buckled and small padlocks were attached to each girl.

In Laura's case, her daughter had chosen the aforementioned five and three quarter inch wide nineteen inch long ass titan; which had been locked securely in place for almost ten hours now. She had originally tried to argue against something so large, as she had a board meeting that morning but, at her eldest daughter's insistence, had allowed herself to be fully impaled on the painfully thick bitch tamer.

Amanda's own butt was packed full with a five and three eights inch dilator to match the rest of her family's size theme. However, Amanda's daily plug was the only one not locked in place as her back hole needed to be accessible throughout the day at the Women's Health and Wellness Expo. The keys to the other Wilder women's straps were kept at home for safe keeping; Laura's in the family's bathroom and Cora and Emily's in their bedroom.

"Both, actually," Amanda replied; her grin only got wider. "But before we get to that, we should really freshen up and change out of our work clothes."

"Agreed," her mother said. "I could really use an enema or two and get out of this corset. I swear; I've been wearing one for almost a solid day and a half now! I'm sure you can say the same."

"Now that you mention it, mother, with the exception of my shower this morning, I've been poured into a tightly laced corset for longer than that. It'd be nice to breath uninhibited for a while," she agreed before adding, "I mean the corset; not the plug sticking into my lungs. That feeling is rather comforting, actually."

Laura sighed. "You are your mother's daughter, aren't you?" she asked rhetorically as she stepped closer to the younger woman and leaned in for a deep kiss. As their tongues danced in each other's mouths, hands quickly found breasts in need of groping and nipples in need of tweaking. Both women were soon moaning in barely suppressed desire to rip off the other's clothes right there in the kitchen.

"Patience, dear," Laura chided as Amanda nibbled on her earlobe; all her daughters knew full well that their mother's ears were amongst her most sensitive erogenous zones after all. It was an empty reproach though as Laura's own hand was down the front of her daughter's black dress and was busy rolling the nipple it had found there forcefully between finger and thumb. With great self control, Laura pushed her horny daughter away; and regretfully removed her hand from the inside of the younger woman's dress.

"Patience," she repeated. "Now, why don't you grab your bag of tricks and meet me in the bathroom. I need to check in on your younger sisters."

"Alright, mom, but don't take too long or I might start without you!" Amanda made a playful biting motion with her mouth before grabbing her gym bag and making for the Wilder family's communal bathroom.

Laura watched her eldest daughter strut away and admired the young woman's curves. Damn! Dave and I do good work! She said to herself before turning to head off towards Cora and Emily's room.

"Now I wonder what those two young hellions are up to this evening", she thought to herself as she walked. "Whatever it is, I hope they're using proper lubrication this time. That was awfully selfish of them to wear out their tight holes so completely that their own mother couldn't even play with them. Of course, I really wouldn't have had a chance to anyway; what with me being tied to a bed all last night. But that's not the point!"

Laura smiled as she remembered last night's punishment session with Amanda. We really should do that again sometime, she concluded. Not tonight; I'm still way to sore for that! But definitely soon.

Her reminiscing had taken her almost to her two youngest daughter's bedroom. As expected, heated passion-filled moaning was emanating from the door-less portal. Laura slowed her approach, not wanting to disturb her daughters while they played, and peaked around the doorframe.

lordodie
lordodie
840 Followers