A Proper Young Woman's Guide to Anal Etiquette

A Proper Young Woman's Guide to Anal Etiquette - Chapter 20

By: Lord Odie

The Obligatory Disclaimer

The following is a work of pure sexual fiction 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 consenting adults over the age of 18. They are also BDSM professionals and good at what they do. So please, don't try anything that you're about to read at home, if such things were even physically possible. If you still insist on trying things at home, please send all pictures and feedback to me about the experience. If I can't stop you, I can at least make sure you're doing it right. Consider yourself disclaimed.

Black Tie Affair

What were good friends for? Mark and Veronica Dermott had a black-tie dinner to attend this Saturday evening honoring the good work of local charities and philanthropists. In addition to the local dignitaries like the mayor and city council, the governor, both senators, several of the representatives, and a good portion of the state legislator would be present. Photo opportunities for such a worthy cause were priceless PR tools for the upcoming elections. Laura didn't consider herself overly political - actually, she considered government at most levels to resemble unsupervised kindergarten classes - but she did keep up to date on current events.

Laura had already [personally] congratulated Mark on his upcoming philanthropy award for selflessly donating so much of his free time to the local Free Women's Clinic for younger, under-privileged women without health insurance coverage. Generally speaking, after graduating from college, young people couldn't land jobs with good benefits until they got some experience under their belts. This left a gap in coverage for most people from their early 20's to their early 30's. For young women specifically, this is the primary time when good anal wellbeing habits learned earlier at home are reinforced. Sensing that need, Mark had dedicated his free time to ensuring these needy young women had someone looking after their wellbeings. He had also worked with local businesses and charities to ensure that the Free Women's Clinic was nearly as well equipped as the Dermott Clinic. That he had been able to pawn off older equipment from his clinic to the Free Clinic at near retail prices to finance new equipment for his own practice didn't matter much in the grand scheme of things. A good deed was still a good deed!

Everything had been all set for Mark and Veronica to attend. Eliza was going to spend the night with Laura, Cora and Emily to give her parents some alone time to celebrate... And then Veronica had been paged for a shift at Richard Johnson Memorial. The hospital was affectionately known as "Double Dick's", or sometimes just, "Double D's" in reference to the minimum cup size required to work there, as the joke went. Evidently, all the on-call doctors had come down with anal fever and couldn't come in. That extra monthly income for being on-call for the local hospital always seemed like free money until a required shift actually popped up at the most inconvenient time! After several frantic screen calls to work out all the schedules and details, Veronica had agreed to show up for a shift at 6:00 PM, Laura had agreed to be Mark's date for the evening, Eliza would take Cora and Emily out for dinner and a holo, and then the trio would head back to the Wilder's home for the night.

That was how Laura Wilder found herself this Saturday evening: in the Dermott's massive family bathroom, seated on one of their three enema units. Their enema units were considerably more expensive smart devices than the units in the Wilder's family bathroom. Also, unlike the ones back home, all three of Laura's lower holes were being cleaned out simultaneously.

Laura sat back at approximately 45-degrees with her legs held up at about a 75-degree angle away from her torso and spread to a comfortable 120-degrees apart, with her knees bent 90-degrees. While the arm and leg rests and the padded bench her back rested against had multiple restraint points to secure a woman to the unit, none were currently holding Laura still. The unit was only set to intensity level 4 out of a possible 10. That was more than enough for a deep cleansing. However, for the safety of the female, full restraints were required for anything over setting 6, the unit wouldn't even engage until everything was secured!

Even at level 4, Laura was impressed with the unit's power! It wasn't the first time she had found herself sitting here, and nor would it be the last! Upon sitting down and placing her knees and legs in the stirrups, she had selected the "Full Orifice Cleaning" at level 4 and relaxed for the 20-minute duration. An expandable grommet with a built-in recession for her sphincter to rest in had inserted itself into her rectum and expanded uncomfortably wide until it made a water-tight seal with her asshole. After that, a porous vaginal probe had inserted itself into her pussy and expanded until her front hole was pleasantly filled. Thirdly, a lubricated, self-guiding catheter had pierced her urethra and had made another water-tight seal with her bladder's sphincter. Once all the telltales had gone green, all three of her holes had begun their thorough power-flushings.

Now, 12 minutes later, she was halfway through the all-important, 10-minute long, "High Temperature, High Pressure, Agitation Phase". Sweat glistened off her naked, flushed body as she sat on the unit and moaned. Her swollen belly looked like she was easily 8 months pregnant. The 122-degree water that had been forced into her body was being kept to temperature by continuous re-circulation through the unit's built-in heating element. The water wasn't hot enough to scald her tender insides, but it was awfully close! The nearly 1 quart filling her bladder and the 1.25 gallons filling her rectum was beyond uncomfortable. Thankfully, the vaginal probe didn't make a water-tight seal with her vaginal lips. Hot water was gushing out of her cunt as fast as the high-volume pump could force it inside. Glancing down between her sweaty flushed 34FF tits, she could see the ripples and waves moving across her taut skin as the high-power vibrator somewhere deep in her colon stirred the water with its powerful vibrations. The fact that her nipples were rock hard did not go unnoticed!

Glancing up, her attention focused on the four people in the shower. Mark had gone in to take a shower. He'd asked Emily to accompany him. Laura didn't think this was unusual. Who wants to shower alone anyway? Cora and Eliza had joined them almost immediately.

Emily had her legs wrapped around Marks thick waist as he pounded his large cock into her young cunt. Emily was alternating crying out to the ceiling and kissing the older man fucking her deeply on the lips. Behind Emily, Eliza wore a sizable strap-on - well, sizable for Emily's petite frame and inexperience - and was enthusiastically ramming it up the young, petite redhead's nether hole. Cora knelt behind Mark. The slightly older raven-haired young woman had her lips locked onto his asshole as she rimmed him out with her tongue. Her right hand was massaging his balls, and her left hand was buried up Eliza's bottom. Laura wished she could join them, but she'd need to finish her hole cleaning and get dressed if she and Mark were to make it to the dinner on time.

Just then, Veronica entered the bathroom. She was wearing a white, cup-less corset. The corset was only tight enough to accentuate her curves. It wasn't tight enough to give her an over-exaggerated hourglass figure. Her heavy 36G breasts jiggled enticingly as she walked on her 5" heels, and her thick nubs were crushed with medium-strength clamps. Her bald cunt and widely gaping open asshole were clearly visible as she walked. Her legs were covered in sheer white stocks held in place with garter straps built into the corset. Unused dildo straps hung between her shapely legs. She was adjusting small golden earrings in her left ear as she walked.

"Mark. You'll be late if you don't hurry up and cum in Emily. I still need fitted with a retention dildo, and then you and Laura need to get ready," the Dermott matriarch said with a quick glance to the shower area before walking up to the vanity to adjust her makeup.

"Almost... done... baby," came Marks reply as his thrusts into Emily intensified. Seconds later, he exploded with a satisfied grunt. Emily felt him swell and came at the same time. Mark took a few seconds to regain his breath and then pealed the young woman's legs off his midsection. Eliza grabbed them before Emily had a chance to lower her legs and leaned back. Emily was forced to reach behind her for balance as Mark disengaged and took a final rinse. Cora immediately scooted forward and locked her lips onto Emily's still quivering gash and began to suck her sister's and Mark's cum out of the tasty cunt. Eliza tried her best to maintain her balance while slowly thrusting her strap-on into 18-year-old's backside.

The display of closeness between the two families - and the incredible vibrations shaking her colonic walls - finally took Laura over the edge into orgasm. The 46-year old mother of five cried out as she came violently. She couldn't help but reach up to twist and crush her rock-hard nipples as came.

"That sounded like a fun one," Veronica commented from the bathroom's vanity after several seconds as Laura calmed down. Laura glanced over at her friend. The 48-year-old busty brunette was leaning over the counter. Laura had an amazing view between her muscular butt cheeks, straight up her empty wide-open asshole. Veronica's entire backside and easily visible cunt was framed perfectly by her stockings and garter straps. Like Laura's own bottom hole, it had been decades since her friend's nether hole had last been able to close naturally.

"It was," Laura confirmed as she relaxed to endure the last few minutes of the all-hole cleansing. She didn't take her eyes off her friend's bottom.

Mark finally exited the shower, grabbed a waiting towel and began to dry off. Behind him, the three younger women were still at it in the shower. "Well, hurry up and get over here," Mark said impatiently. "You'll be late if I don't fit you with a daily dildo," he added mischievously.

"Yes, dear," Veronica replied with a roll of her eyes. "I'm sorry to have kept you waiting so long..."

Mark just chuckled. He and Veronica crossed the bathroom to an old-school plug fitting bench. These days, most households had some kind of automatic plug fitting device. Actually, an expensive, full featured, fully automated one was in the master bedroom's changing room. The Dermott's kept this old one around because Mark liked to handle plug fittings manually most days.

Veronica crawled onto the low bench. Her knees found the independently moving knee-to-shin pads easily. She bent over and allowed her 36G breasts to slip through the cutouts, and her face came to rest on the U-shaped pad that ran across her forehead and cheekbones. Veronica's position spread her legs maybe 90-degrees apart from each other. Finally, she placed her arms behind her back and waited patiently. From her seat on the enema unit, Laura had a great view of the bench. She was maybe 10' away and 45-degrees behind and to the side of Veronica.

Mark quickly wrapped a wide strap around his wife's forearm, immobilizing them in the small of her back. He then began stepping on a small foot pedal maker "#1" until Veronica grunted. Laura could hear a soft mechanical ratcheting sound and her friend's breasts began to bulge out. She knew that a thick band had constricted around the base of each of the brunette's bulbous tits. Switching to foot pedal "#2", Mark began to pump. It only took a few pumps for Veronica's now orb-like tits to be pulled downwards forcefully, accompanied by more ratcheting sounds and more stressed grunting from Veronica. Next, Mark brought a wide leather belt around Veronica's lower back, yanked it in place and buckled it securely. This caused Veronica's butt to stick straight up at the ceiling as her back was arched severely as Mark strapped her knees and legs in place. Finally, Mark began pressing foot pedal "#3". This caused the knee pads to rise, which forced the arch in Veronica's back to an even more extreme, until it looked like her buttocks were nearly at an 80-degree angle from her backbone. Thoe older brunette just moaned in discomfort at the extreme angle but made no attempt to move or resist. Not that she was in any position to do either!

Laura had to admit that this position did give Mark unfettered access to his wife's completely defenseless holes. She had to lick her lips as she admired her friend's now massively gaping asshole, and slightly gaping cunt, the latter of which was now clearly dripping with excitement.

Picking up a 1.025" wide, pre-lubricated punishment catheter, he quickly sunk the entire length into Veronica's already red, sore looking urethral opening. He gave the end of the metal sound a few quick twists to enlarge its tip just inside Veronica's bladder, locking it in place. A special key would be needed to remove it. Although, tubing could be attached to drain the bladder throughout her shift.

Next, Mark picked up the massive 7.35" wide, 24" long, lightly veined dildo that would spend the next ten hours or so locked inside the 48-year-old's dilapidated rectum. Veronica had achieved 100% Certified Capacity several years ago and Mark was not about to allow his wife to lapse a fraction of an inch. Because of this, all her dildos were now 7.35" wide - daily, punishment, torture, medicated... All! While this didn't allow her ruined sphincter to a moment's respite, it did allow her dildo collection to be quite small for her age.

Despite years of being constantly dilated to 7.35" wide, her poor asshole still wasn't entirely used to being open that wide yet. Even half an hour of being empty and her asshole had already closed up significantly. It took the huge, muscular man several minutes, and all his body weight, before the impossibly thick head of the Veronica's daily dildo to finally slip inside. She let out a pain-filled scream, shook horribly, and whimpered as her loving husband fed the entire 24" length into her protesting body.

By this time, Mark was once again fully erect. He lined up his cock with his wife's now gaping cunt and shoved in his entire 11" length in one powerful thrust.

Veronica cried out! "Baby! Are you sure you have time? You're going to be... Ooohh... late," she protested halfheartedly.

"There's always time for a quick cunt fucking!" Mark replied as he built up his pace. "I'll be quick," he added reassuringly. By now he was squeezing both of her meaty ass cheeks and using them to run his cock into her quivering snatch with powerful thrusts. Veronica only groaned in a mixture of pleasure and pain as her contorted body was lovingly grudge-fucked by her large husband.

Laura was watching all this as the enema unit she was on dinged completion and pulled its probes out of all three of her lower holes. She stood up on shaky legs and used a nearby towel to dry off the water that was still dripping out of her holes. Inside the shower, the girls were now in a three-way, mouth-to-pussy, fist-to-asshole triangle on the shower's floor. It was nice to see them bonding. Reluctantly, she left to get ready.

In the bedroom, she quickly dried off her sweat, although, her skin retained its flushed color. Although, her nipples remained hard in the room's cool air-conditioning. She quickly slipped on her cup-less black corset. Attaching a universal auto-tightener, she set it to give her a shapely, exaggerated, hour-glass figure and went to work slipping her black stockings on while her corset tightened. She put on her 6" black high heels and was tightening the horrible nipple clamps she'd bought at the Women's Health and Wellness Expo a few months back when the auto-tightener finally dinged completion. She had a love-hate relationship with the horrible little devices now dangling from her sensitive nubs. They hurt like nothing she'd ever subjected her poor nipples to, but the pain the produced caused her cunt to absolutely leak fluid.

When she returned to the bathroom, Mark had already cum. Eliza was orally cleaning his shaft off while Emily and Cora dried off. "Clean up your mother and then release her," commanded Mark. "I have to fit Laura and get dressed."

"Yes, Daddy," Eliza replied and turned to her mother's cum dripping snatch and dove in greedily.

"Come this way," Mark commanded Laura as he walked past her without a look behind him. He knew his commands would be obeyed. Laura loved being told what to do so offhandedly by a strong dominant - male or female. A small part of her once again missed Dave as she turned to follow Mark into the master bedroom's changing room.

Despite knowing what was waiting for her before-hand, she still whimpered when she saw the massive, 6.45" wide, 24" long, horribly studded, heavy-grade torture dildo mounted to the auto-fitter's spindle. This was equal to her current maximum dilation, and she'd only just achieved 6.45" wide last weekend during an extended session in the Dermott's huge family dungeon. Laura herself had lubricated it with slow-drying hot pepper lubricant as she'd been instructed to earlier and had secured it to the auto-fitter half an hour ago. At that time, it didn't scare her. The thought of it penetrating her sore backside was just theoretical at that point. Now with Mark impatiently patting the auto-fitter's padded bench, the threat was imminent. She had a very good idea how horribly each of the dildo's stiff pyramid-shaped studs would tear at her delicate insides. The last inch or so of the dildo's length was covered with smaller, stiffer, more densely packed pyramids - just waiting to dig into her soon to be over-stretched sphincter.

"Come on, Laura," Mark said reassuringly. "We don't want to be late," he said walking over to his wife's best friend. He reached down and kissed her gently while slipping three fingers into her dripping cunt. Laura tensed and widened her legs to allow Mark easier access. Submissively, she allowed Mark to lead her over to the auto-fitter. She leaned back on the 45-degree backrest as Mark lifted one leg, and then the other and belted them into position so that Laura was spread into a perfect, 180-degree splits. Firm pads rested on the tops of her thighs to ensure she wouldn't scoot on the backrest. Stepping behind Laura, Mark gathered up her arms and slipped them into an arm binder and tightened it down until her elbows met. He then fed the strap at the hands into a pulley end pulled them until Laura's arms were nearly pulled straight back and away from her body in a severe strappado. This caused her breathing to become harder as it put a lot of strain on her lungs. Coming back around to her front, he noticed that her impressive nipple clamps were nowhere near as tight as they should be and gave each a full additional turn.

Laura finally cried out as pain exploded into her already horribly crushed nipples. "Fuck!..." she finally said in defeat. She knew better than to beg him to loosen them.

"Ready for your French Fitting?" Mark asked as he tapped a few commands into the auto-fitter's control panel. French Fittings had become quite popular in Europe and were starting to become popular even here in the States. Although, with indecency laws in the US what they were, you had to be a lot coyer with how you talked about it. Basically, a French Fitting was having a maximum capacity torture dildo was locked into a woman's rectum while she was wearing a corset that restricted her waist. While wasp-waist-style corseting wasn't that fashionable, having an hourglass figure was. That still left little room in a woman's abdomen for a massive slab of latex to be inserted. Make it a horribly studded torture dildo, and a significant amount of force was required to fully seat the dildo. Thankfully, the Dermott's auto-fitter was the most powerful fitter commercially available.