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

Author's Notes:

I'd like to take this opportunity to introduce Mary Wilder and a few more characters that 'may' (cough, cough) be showing up in the main story line before not too much longer. I'd also like to showcase some of the more extreme examples of everyday anal dilation that exist in Europe at the same time as the Wilder clan is living it up back in the New World. If you'll remember, public indecency is still a criminal offense in the States; not so much in most of Europe.

Even though this story actually takes place in the UK, all measurements are in Imperial (US) units for the ease of my American readers. Anyone used to the Metric system will have to forgive me. Because we all know that us crazy, backwards Americans will never give up our yards! [American] Football would never work in centimeters...

And fear not! Laura and the girls will return in the next chapter to complete their long overdue physicals...

Across the Pond, Part I

At the same time that Laura and her two youngest daughters were undergoing routine physical examinations at the Dermott Women's Clinic, on the other side of the pond, Mary Wilder – Laura's second oldest daughter – and her fiancée, Victoria Marie Deveraux, were just finishing up their day at work. Victoria worked as the Head Mistress for Saint Patty Parker's Finishing Academy in downtown Nottingham, while Mary was her personal executive assistant.

The pair had actually met at Saint Patty's eight years ago while the then eighteen year old Mary was attending as a student and thirty-one year old Victoria was teaching the Personal Ambition and Morality course. Mary had a full ride scholarship as part of the court settlement from her accident. Victoria was only teaching as a side job after she'd graduated from law school. Nevertheless, Associate Mistress Deveraux and Miss Wilder had taken a liking to each other almost immediately. Neither one of them had expected that they'd still be wandering the halls of Saint Patty's so many years after they'd originally intended the school to be nothing more than a stepping stone to bigger and better things; but opportunities come from where you least expect them. Life is funny that way.

Saint Patty's is a world-renowned finishing school devoted to instructing young women in fine society, art, music, proper behavior, self respect, and personal motivation. Many of the most successful female political and business leaders throughout the world darkened the doors of Saint Patty's in years past; including the CEO of Macrosoft, the Vice President of the United States, and the Prime Minister of the United Kingdom. Eighteen and nineteen year olds worldwide compete for openings in the school after they graduate from secondary school; or high school as it's called in America. Students normally graduate after a single year and then move onto institutions of higher learning; more often than not with generous scholarships already lined up; although some students find that attending Saint Patty's for a second year better prepares them for adult life.

Of course, as society has evolved from generation to generation, so has Saint Patty's: As a direct result of that, proper anal etiquette has been a major part of the curriculum for decades. A respectable degree of anal dilation is expected from all young women before they are ever granted acceptance; even with the knowledge that each girl's nether opening will get significant attention throughout their continuing education. During Mary's single year as a student, her maximum capacity increased at a faster pace than it had since she'd first begun anal training with her mother when she'd come of age. Of course, Victoria's own backside was never missing out on any action either. As Saint Patty's firmly believes in leading by example, all the mistresses spend almost as much time in the school's extensive Detention Hall as the students do.

That year was also Victoria's first year as an associate mistress at Saint Patty's. Because of that, she and the other two first-year mistresses had daily punishment and dilation sessions scheduled from 06:00 AM to 08:00 AM; Monday through Friday. Unluckily for Victoria, her first class didn't start until 10:00 AM, so she normally spent an additional hour or so as Senior Mistress of Corrections Svetlana's personal project; the 08:00 AM hour was generally pretty slow in the Detention Hall, after all. Despite the additional pain and suffering she'd undergone, she couldn't argue with the results. Even to this day – though Chief Mistress Svetlana now technically works for Head Mistress Victoria – Victoria has given the older woman a free rein on the training regime for Saint Patty's head mistress; it's a setup that Victoria only regrets occasionally, but has never once tried to reverse.

***

Victoria pulled her Jaguar F-Type into the garage of her townhouse in an upper middle class neighborhood outside of Nottingham and put it in Park.

"What a day," she announced rhetorically to the lovely young woman seated next to her. Glancing sideways, she admired the form of her beautiful fiancée, Mary Wilder. At only a medium height and with brown hair, the younger woman's best features were undoubtedly her perky 36FF-cup breasts. They were certainly what had gotten a younger Victoria's attention in the first place. Though, as impressive as they were, many young women had equal or greater womanly assets. What had eventually won Victoria's heart had been the younger woman's bright eyes and zest for life despite the loss of the use of her legs. The young woman's shapely ass and very well trained and responsive nether hole had played a great part in their eventual engagement as well. Victoria was fond of her personal theory that all the nerve endings her love had lost in her legs had been relocated in between her legs. It was a theory that Mary found hard to disprove as her dominant fiancée drove her to orgasm after orgasm.

Despite nearly a decade without the use of her legs, Mary still maintained a trim, hour-glass figure which accented her delicious breasts and full hips delightfully; a testament to a daily workout regime focusing on her core muscle groups. The fact that Mary enjoyed her role as a masochistic bottom even more than Victoria enjoyed being a sadistic top was just icing on the cake!

Victoria was no slouch in the looks department either. At thirty-nine, her curvaceous figure turned almost any heads that were in the vicinity; both male and female. With long, light-brown hair, a pretty face, 36HH breasts, trim waist, and firm buttocks packed into a 5' 8" frame, Victoria could have had almost anyone she chose to have: man or woman. If she'd had the mind to do so, she probably could have had multiples of both on speed dial!

However, because of her looks, she'd often found the hardest part about teaching to a room full of sexually over-charged girls at Saint Patty's was keeping her young charges to pay attention to the lessons she was trying to teach and not the deep cleavage of her low-cut blouse; or the ever-present outline of her large nipples; or her well-rounded ass squeezed into her tight skirt and shaped perfectly by her six-inch heels. Of course, all of the above was the mandated attire for all mistresses at Saint Patty's; a dress code that Head Mistress Victoria did little to alter.

That her first husband had left her ten years ago for a younger, significantly more submissive woman with larger breasts, a stretchier ass, and an even more advanced case of anal masochism was more of a result of the five to one ratio of women to men on the planet than him actually growing tired of his bride; that, and the fact that his penchant for rough breast play during sex had gradually exceeded even Victoria's tolerances for kinkiness. Like nearly all women these days, Victoria was a perfectly willing – even enthusiastic – participant in extreme anal play, but being suspended from her breasts for hours at a time while her husband played with her nether hole had finally become too much.

However, the taste for such extreme kink still remained with Victoria; but on the reverse side of the bondage. Thankfully, Mary was only too happy to allow Victoria to do the very same things to her that Victoria herself had complained about to her ex-husband so vehemently. The hypocrisy of it all never failed to bring a smirk to Victoria's lips. Perhaps she and her ex were just never meant to be. After all, having two sadists in a relationship was nowhere near as interesting as a well paired sadist and masochist.

She had asked Mary to marry her over two years ago and their wedding was coming up this summer; mere months away. There was only going to be a small ceremony here in England with close friends and family, while the main ceremony would be back in the United States – Mary's family was considerably larger and more conservative and would want to participate in the ceremony. They were both looking forward to the wedding back in the States; and, of course, spending more time with Mary's mother and sisters. Victoria had always thought Laura had the best toy collection.

Mary smiled back weakly – exhausted from her strenuous afternoon – but said nothing in return. Victoria's heart melted; or maybe it was her pussy. Mary always knew exactly what to say – or not say – to get Victoria's motor going. Victoria smiled back, killed the engine, and then opened her door and exited the vehicle.

No sooner had the car's engine died than Alicia, their live-in maid, appeared from the house's inner door pushing Mary's home wheelchair. Victoria had called ahead to provide instructions and Alicia had followed them to the letter; just as she always did. As Victoria moved around the front of the vehicle, she nodded approvingly at the massive slab of latex protruding from the chair's seat; exactly where Mary's well-shaped butt would soon rest. "Thank you, Alicia," Victoria said as she opened the passenger side door while the maid positioned the chair for the transfer. "You even attached the studded plug, just like I requested."

"Thank you, Mistress," Alicia replied with a small curtsy. "When you said that Mistress Mary had been naughty today, I knew you weren't joking when you mandated which plug to use," she added. Despite working for her current employers for over a year, the size of the plugs that always seemed to find their way into Mary's well cared for rectum – or Victoria's well trained back hole for that matter – never failed to scare her slightly. Such large objects would never fit inside her tiny frame. At merely 4' 11", Alicia was a very petite twenty three year old. While her own backside was well trained by her mother, and now maintained by her employer, anatomy physically prevented such plugs from being used on her; her hips were simply not wide enough.

Not that Victoria wasn't constantly pushing the physical limits of Alicia's small rear hole. The mousey little red-head's perky 32D breasts and heart shaped ass guaranteed her continuous attention from the mistress-of-the-house's insatiable appetite for hot, young, female ass. The sizable plug that was continuously stretching her nether hole at all times was a testament to that.

The French Maid outfits that were her daily uniforms had attachment points built into their construction; which was really no surprise there as all modern women's clothes had similar hard points. Alicia's outfit was fairly traditional: It started with a tight black leather corset which made her already small frame appear almost fragile. Above the corset, a quarter-cup push-up bra enhanced her creamy white cleavage while at the same time leaving her hard, pink nipples exposed at all times. Below, a black mini-skirt that almost covered her pussy mound when she stood up straight and did nothing to hide her bald cunt and painfully plugged ass whenever she bent over – an act which she was required to perform for any movement that it could possibly be incorporated into. A frilly white apron, black garters and stocking, black patent leather high heels, and classic maid's hat completed the ensemble. She would have thought of herself as looking ridiculous – especially when she went to the market with nothing else to cover her body – if not for the fact that most of the maids she met in the neighborhood had a very similar attire; and compared to some uniforms she'd seen out in public, hers was downright conservative!

"Yes, she has been naughty," Victoria continued as she unbuckled Mary and helped her out of the car. Locking the wheels of the chair, Alicia quickly moved over to grab the leg closest to her and assist her mistress in aligning Mary's empty and well-dilated anus up with the pre-lubricated six and a quarter inch wide, twenty two inch long, studded latex rectum wrecker through the cutout in the woman's expensively tailored business skirt.

Mary only moaned at the familiar penetration of her favorite punishment dildo and gripped the arms guiding her downwards. Just like her mother, Laura Wilder back in the States, Mary had a full set of heavy grit dilation plugs for serious punishment – as did any proper woman – but she'd never considered those her 'favorite' punishment plugs. The large studded plugs that Victoria preferred to punish her with brought almost as much pleasure as they brought pain; which only meant double pleasure to an unabashed anal masochist like Mary Wilder. She let out a soft sigh of pleasure as she felt her butt checks come to rest against the chairs comfortable seat and the extra long rectal violator come to rest against the base of her lungs. Mary took a few seconds to enjoy the sensation of fullness in her behind as Victoria adjusted the lap restraint.

"You won't be sighing for long, Mon Amour," Victoria commented to Mary about her audible sound of pleasure. Turning back towards Alicia, who had taken position behind the chair, "Wheel her around the block for an hour or so, just to get her nice and loosened up for later tonight, won't you please, Minette?"

"Of course, Mistress Victoria," Alicia responded politely; understanding now why her employer had instructed her to insert a four and a half inch wide, studded dilation plug up her own bottom. That was quite a sizeable plug for such a petite woman as Alicia. Mary would not be the only one who would be sore and well stretched-out after their walk. She contemplated her probable fate tonight as she began pushing Mary out of the garage and down the short driveway to the sidewalk. Probably better than Mary if she had been naughty, she figured, as she looked down at the back of the wheelchair.

Unlike the chair which Mary rode in during work hours, the backside of this chair was wide open for the world to see. As Alicia rounded the corner and began heading south down the street, she watched the sizable dildo extract itself about six inches from Mary's poor bottom, rotate thirty degrees and then pound back to its maximum depth. The speed of the penetrations was geared directly into the speed of the chair's wheels; the faster Alicia walked, the harder Mary would be punished. Of course, there was a ten-speed gear selection lever up on the handle. The higher the speed, the faster the fucking was relative to the speed of the chair. In the tenth gear, and when the person pushing the chair was at a decent jog, the speed off the attached dildo could make the female in the chair's teeth rattle violently. Alicia had witnessed that occurrence on many occasions when she'd accompanied Victoria on her daily morning jog.

Of course, Mary's workplace wheelchair was identically equipped. Its inner workings were just hidden from view for the benefit of the clueless students. The helpful young women actually thought they were doing Mary favors when Victoria instructed them to wheel her around Saint Patty's school grounds for an hour or so every afternoon so Mary could get some fresh air. Although, truth be told, they were indeed doing Mary's ever eager asshole marvelous favors.

Feeling a little more sadistic than usual – which Alicia was sure was partly due to the growing soreness in her own tight hole – she clicked the lever from second to third and then to fourth gear. The higher gears brought about a noticeable change in the sound the fucking mechanism made as it went about its business; as well as the sounds emanating from Mary on the receiving end of the device. Neither woman made any comments regarding the gear change as they walked along.

Mary let out a soft groan of mixed pleasure and pain. She swore she could hear the vibration of her tightly stretched sphincter from the plug's latex studs ripping in and out of it. She knew it was her imagination, but she swore it was an audible hum. It almost sounded like a plastic comb running over her fingers.

Such public displays of anal depravity would have mortified her nineteen year old self before she'd come to Saint Patty's those many years ago but now, at twenty seven, she found such things normal; almost comforting. She almost pitied her mother and sisters back in America for the backwardness they had to put up with.

No sooner had that thought crossed her hormone-addled mind than she was once again reminded that she lived in Europe. As she was pushed past a bright red Porsche 911 Carrera, that had just parked along the side of the road, the woman in the driver's seat got out of the car and bent over to reach back inside. As Mary and Alicia approached, they could easily see up inside the woman's fully dilated rectum as her mini skirt rode high on her hips and the gaper panties she wore stretched her sphincter to its maximum. Her bald, moist pussy lips were equally visible under her yawning rear chasm as the skirt rose further.

"Good evening, Mrs. Carver," Mary managed to get out as they passed.

Without standing up or attempting to cover herself, the woman simply looked back over her shoulder and answered, "Hello, Mary. Pleasant evening isn't it?" as she stuck her shapely butt out a little farther for Mary's viewing pleasure. The shape of a large pink latex cone affixed to the driver's seat was clearly visible as Mary was wheeled past. Mrs. Carver was cleaning lubricant from it with a tissue.

"Very pleasant," Mary answered as she admired the woman's destroyed anus and beautiful car equally.

"Have a good ride, dear!" Mary heard her say as they walked past. She knew that Mrs. Carver had a full view of the thick toy plowing into her defenseless ass as the wheelchair rolled away; just as Mrs. Carver knew that Mary and Alicia had had an unobstructed view up her gaping asshole as she'd cleaned off her driving cone. Despite the wanton displays of anal perversions that had just been exhibited by both parties, all Mary could think was: who the hell parks a Porsche 911 Carrera on the side of the street?!

Perhaps she'd been in the UK a bit too long, she thought.

"I will," Mary called back over her shoulder; and she planned on just that.

After another minute, Alicia clicked the lever to the fifth gear and the fucking mechanism began to whine slightly. Mary rolled her head back and closed her eyes to fully enjoy her punishment. Alicia took the opportunity to admire her charge's deep cleavage from her higher position. God! She wished her breasts were that size naturally! Maybe if they were, she could attract a nice man or woman and settle down instead of being a mere maid. There was always time though; she was still young.