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.

Déjà Vu, Part I

Just down the hall inside the Wilder home's large central bathroom, Laura was admiring herself in the mirror that took up one entire wall of the huge room. For forty-six, she looked amazing and not a day over what twenty-nine would have looked like just fifty years before; a testament to modern genome anti-aging treatments. She had another decade to look forward to before she could expect her magnificent breasts to start showing significant signs of sagging; despite their amazing 34FF cup size.

The bathroom itself was pretty average for modern upper middle class suburban construction. The spacious room was designed to accommodate several people simultaneously. The wall Laura was standing at consisted of nothing but an expansive wall to wall and ceiling to floor mirror that helped to give the impression that the room was even larger than it actually was. Against another wall there were three pairs of commodes and bidets; each separated by less than a foot. This close positioning allowed the persons occupying adjacent fixtures to 'assist' each other as necessary. Each bidet also came equipped with the necessary faucets to attach enema equipment of various types and purposes.

Across from the plumbing fixtures was the bathing area. This was separated from the main bathroom by a glass wall to trap heat and steam for the comfort of the bathers. The bathing area contained three large detachable shower heads. Sunk into the floor and extending out into the middle of the area was a large whirlpool tub big enough for four people comfortably; six people if the occupants didn't mind being crowded.

The last wall of the bathroom contained one long counter with four recessed extra large sinks and matching oval mirrors. Under the counter were cabinets containing all manner of things: personal hygiene items, towels, robes, enema equipment, medications, hair and beauty products, and even a few light bondage items like hand cuffs, ball gags and general purpose leather and rubber straps. The enema equipment included your standard fair of plugs, bags, injectors, lubricant, hoses, speculums, wands, etc. It was nothing out of the ordinary for a modern family and almost everything could be picked up in the pharmacy department of a local supermarket.

Bringing her attention back to the sexy woman staring out from the mirror in front of her, Laura tested the perkiness of her reflection's boobs by cupping them with her hands and pushing them up before allowing them to drop a few times. She nodding in satisfaction to herself at the pleasing swell of top boob and cleavage this created. Reaching behind her shoulders, she found the zipper to her expensively tailored dress at the base of her neck and began unzipping the back slowly. As the garment lost its tautness, her ample chest began to reveal itself gradually to her lust filled eyes. She watched with anticipation as the zipper reached the bottom of its track at the small of her back and all that was holding the soft fabric to her fantastic breasts were the dress's sleeves; and as she brought her shoulders forward, even those gave way to gravity's irresistible calling. Her breath caught as the dress finally slipped away and her proud tits swung free of their confinement for the first time since that morning. Instinctively, her hands wandered up to those two lovely orbs to caress and fondle them as she watched her reflection's response intently.

Laura was interrupted by the pleasant sounds that had suddenly started drifting down the hall and into her private sanctuary. It was obvious to the mother of five that her two youngest daughters were most likely being sodomized by her oldest daughter with what she assumed were Amanda's pair of expert fists. God only knew how many lucky women had been reduced to quivering orgasmed-out wrecks with their butts on the receiving end of Amanda's large – for a woman – and very strong hands. Certainly a lot more than Laura knew about; and she knew about quite a few. Laura could personally attest to the skill and determination of her oldest protégé's skills with her fists. After all, she had taught Amanda everything she knew on the subject of deep anal penetration of a woman's posterior using nothing but the only suitable tools for the task evolution had given women.

Laura's fingernails slid down the inside of her breasts as her mind peered inward and she reminisced on times past. Goosebumps rose across her skin in response to the gentle touch and her nipples hardened instantly.

The act of fisting had always been a favorite of Amanda's; both giving and receiving. At least twice a week – while Amanda was still in college – during her nightly training sessions, they would take turns fisting each other's ever-expanding assholes till the other exploded in orgasm after orgasm. Some of Laura's most cherished memories of her oldest daughter were while admiring the look of total concentration on her young face – as viewed from between Laura's widely spread legs – as the younger woman drove her fist as hard and as fast as possible into her mother's anus again and again and again. Amanda's favorite technique was to make a fist and pull completely out before punching straight back into her mother's always well dilated hole.

Amanda had needed constant pointers and tips as to the best way to get an arm as deeply into a woman's rectum as possible. Depths well past the elbow were common place and expected. If Amanda was having an off night and not pushing deep enough into her frustrated mother to get her to cum nice and hard the way she needed to, a refresher course was always given by her father. Dave was determined to make sure his oldest daughter knew how to deeply and properly fist fuck a woman's ass. Amanda's punishment would fit the crime. She was forced to sit on her mother's face and watch on enviously as her father pounded his fist into her mother's gaping asshole, all the way up to his elbow, for at least ten or fifteen minutes.

Laura would apologize fervently for her failure – as a teacher and as a mother – to her oldest daughter during these prolonged refresher courses. Either by greedily feasting on the sloppy young anus above her face or by pulling her daughter's hips backwards slightly to dig her tongue into her daughter's gushing cunt and freeing up the younger woman's asshole for a shallow anal fisting to help console her during her punishment time. Amanda always thanked her mother by cumming all over her face at least two or three times.

Naturally, a fisting of this caliber always caused Laura to cum quite a few times herself. After all, this was one of the ways she and Dave played together when they were alone anyways. Of course, they had many other fun games that were common for married couples to engage in as well; almost all of which usually left Laura's poor and battered sphincter remarkably sore the next day.

"There! Now that you've seen how to do it properly," Dave would always say as he wiped sweat from his brow, "Do it again! And deeper this time!" After he'd finished giving his wife enough bicep motivated anal orgasms, it was usually very easy for Amanda to get her arm in just as deeply as her father; what with the smaller tools she had to work with. Dave had very big and powerful arms and hands. Laura had always loved being fisted by Dave. It was one of the reasons she fell in love with him in the first place.

Of course, Amanda always came faster and harder than even Laura did when it was time to change positions and Laura took charge of her daughter's anal pleasure using the exact same technique. Forcing orgasm after orgasm out of her daughter's delicate rectum as she punched her fist into the gaping chasm between her Amanda's butt cheeks. This gave her enough time to recover from her own anal orgasms. Soon enough, it would be time to switch places and Laura could be a bottom once again. Amanda did need a lot of practice after all.

This weekly training regime had remained fairly consistent until the young woman turned twenty-two and Laura introduced her to double anal fisting for her birthday. After that, the frequency of anal fisting during their daily sessions became closer to three times a week. Amanda soon became an expert at sinking both fists up her mother's protesting back portal until she felt the older woman's sphincter trying to swallow her elbows. At that point she'd alternate driving her arms in and out of her mother's poor ass – elbow to wrist and back again – as forcefully as she could. Laura had never been able to take more than ten minutes of such a brutal attack on even her well trained ass before the sensations became far more painful than pleasant. Dave, who was very aware of Laura's limits, never allowed Amanda to stop until at least twenty minutes had passed during each session; no matter how tired or exhausted his straining daughter might become. Laura never experienced such mind blowing orgasms as she'd always had towards the end of the twenty minute mark. Amanda had always given her mother a few good minutes extra; just to prove she could, and Laura was proud for her daughter's extra determination in her lessons.

Of course, after Laura recovered, it would be Amanda's turn to lay back and spread her cheeks so her mother could sink her arms into the sloppy hole that years of dedicated and strenuous training had transformed her once tight anus into. Amanda would always confide in her mother, as they cuddled afterwards in their mutual post-orgasm afterglow, that the double fisting usually became almost unbearable after only a few short minutes. She would then thank Laura with deep and passionate kisses for always going the fully allotted twenty minutes before stopping because her orgasms towards the end were amazing.

Like mother like daughter.

Laura's mind returned to the present as she stood in her family's spacious bathroom. Not to her surprise, she discovered that while she'd been far away in the past, her fingers in the present had found the hard nipples atop her glorious breasts. Her fingers and thumbs had obviously been very busy pinching and rolling her sensitive nubs; she could tell by the angry red coloration they were developing from the absent minded abuse. The pleasant dull and painful ache she was feeling from the tips of her tits confirmed it. Now that she was conscious of her mischievous hands transgressions against her defenseless breasts, she really allowed the tenderized nubs to have it as she dug her index fingers and thumbs deep into the base of each areola and squeezed as hard as she could. Her knees went weak with the pain in her mammaries and her pussy started to melt. Amanda slowly tilted her head from side to side and relished in the warm sensations flooding into her needy cunt as she began to roll her flattened nipples brutally without releasing any pressure.

God, she was such a pain slut when it came to her nipples. She'd been very surprised when most of her daughters hadn't grown to share in that trait. Thankfully, her youngest, Emily, showed just as much of an appreciation in painful nipple play as her mother did. It was one of their shared interested in which they bonded over. They could spend hours chatting over the pros and cons of each piece of Laura's expansive nipple clamp collection; trying them on as they went.

Speaking of clamps, her fingers were starting to tire but her poor breasts were just getting into the pain being inflicted on them; and she needed her hands free anyway. Moving over to the bathroom counter, she regretfully released her angry red nipples and was briefly rewarded with a fresh flash of pain as blood returned to the crushed tips.

"Let's see," Laura mumbled to herself as she opened the small jewelry cabinet on the counter which contained most of her favorite nipple clamps. "Nope. Nope. Not strong enough. Nope. I never liked the color of these against my nipples; why do I still keep this pair?" she continued shifting though her collection. "Not these. Huh, I wonder where this one's mate got to... Nope. Not that pair, those actually draw blood and I'm not feeling like that flavor of pain tonight. Nope... Ah! Here we go. A nice strong pair of bar clamps with constriction screws, perfect!"

Laura's nipples were already hard to the point of bursting; perfect for clamp application. Seating the first clamp at the base of her right nipple, she began to turn the screws which brought the two bars steadily together. She felt the bite as the unyielding bars started squeezing yielding nipple flesh; she kept screwing down. She knew she had the right amount of tension when she doubled over briefly in pain. Standing up, she gazed at herself in the mirror and was pleased to see misting at the corner of her eyes. "Perfect," she said as she reached for the second clamp. A minute later and a wincing and softly sniffing Laura admired her crushed nipples in the mirror. "Perfect," she repeated as she allowed her fingers to dip down to her completely drenched snatch.

Only allowing two fingers of her right hand to enter her gooey cunt, she stroked them in and out a few times before extracting them and bringing them to her lips. The scent and taste was intoxicating as her mouth closed around the fingers and began sucking gently. She returned to the mirror-wall to admire herself as she transferred more and more sweet pussy juice from her overflowing slit to her greedy mouth. She always loved the taste of herself the best after a long day at work.

The image that greeted Laura in the mirror was breathtakingly hot. Her dress had concealed a full boned deep imperial purple leather corset that she wore to flatten and smooth her already muscular stomach. The corset actually had no breast cups at all which allowed her huge rack to sway incitingly from side to side - nipple clamps catching the reflection of the overhead recessed lighting - as her hands moved from her pussy to her mouth and back again. The deep purple of the hard and constricting garment contrasted provocatively with the pale white of her milky breasts and the dark red of her flowing hair. Below the bottom edge of the expensive lingerie appeared her sopping wet pussy; still being penetrated by two of her questing fingers. Her shaved bare front hole was in turn framed by the black silk stockings and black satin garters holding them up. Peaking out just below her wet pussy lips could be seen just a shadow of a large black mass. She was a serious piece of fuck meat if she's ever seen one; and she had seen many, many of them! Too bad Dave wasn't here to take her. She needed to be taken. And hard!

Even though the tightly closed corset shaped her already hot figure to the point of spontaneous libido combustibility, she actually wore it for a very functional purpose. Without the strong boned corset, her abdomen would have bulged outward obscenely with the shape of the gigantic five and a half inch diameter, eighteen inch long plug that she'd inserted before leaving for work that morning. The same toy was still deeply packed into her straining rectum.

She'd decided to wear a dilator plug this morning instead of a normal butt plug. The chief benefit of a dilator plug over a more traditional butt plug was that it had no neck for her painfully distended anus to find temporary relief by closing itself around. The only part of the plug's shape that deviated from the thick cylindrical tool was the large circular flange at its base. This ensured that the plug was not accidentally swallowed whole by the very ass that it was supposed to be training. The design allowed for the maximum strain to be placed on the entire length and depth of her expertly trained rectal track; from the tortured sphincter between her tones ass cheeks to the deepest darkest depths of her large intestines somewhere around the base of her ribcage.

As Laura's thoughts dwelled on the huge plug invading her body, her hips began to slowly gyrate. She allowed herself the pleasure of forcing a third finger into her dark front hole. She gasped and sucked her fingers harder as she considered the advantages to the toy her body was hiding in plain sight.

Another aspect to a dilator plug was that since there was no neck for her battered ring of rectal muscle to grip onto, she had to wear a dildo strap to ensure the toy didn't simply fall out of her ass when she stood up. While the thought was humorous, she would simply die of embarrassment should something like that ever happen in public; let alone in her conservative workplace. The dildo strap securing the huge latex rectal violator inside Laura was actually designed into her purpose built corset. It started as two pieces of tough leather from the left and right side of her pelvic bone in the front. These passed on either side of her dripping pussy to join up into a single strip of leather just past her moist hole. This allowed Laura's empty front fuck port to be used freely and without the need for her to undress. It also permitted her to urinate when nature frequently called. Her young secretary Tanya had verified the first feature worked as the designer intended over lunch – to Laura's screaming and writhing pleasure – and the greatly reduced space in her torso for urine storage in her bladder had ensured the nonstop trips to the ladies' room throughout the day.

Laura paused in her excited fingering to reposition the straps she'd been considering to allow her easier access, before continuing to stroke her fingers in and out of her steaming gash. Her mind continued to wander onwards as she considered the finer points of her lingerie's engineering.

After merging back into a single strand of leather, the dildo strap continued upwards through a metal tab in the base of the massive plug to guarantee that removal was impossible. It was finally secured to a buckle at the base of her spine. This same buckle also secured the constricting laces of the corset itself. Having the same buckle serve two different and necessary functions allowed a single small lock to be placed into it so that, without the key, removal of the corset and plug were virtually impossible. Laura had placed just such a lock in position before smoothing out her dress and leaving that morning. The key still rested where she left it: next to her and Dave's wedding rings on the counter next to the sink.

She didn't really need a lock to ensure the horrible plug remained where it was; she had more than enough willpower to leave it in place. Laura just liked the comfortingly submissive feeling of having the decision to remove it out of her hands. The fact that Dave had always locked her daily plugs deep inside her bowels before they left for work was something she deeply missed. While it was true that during today's workday she was just as powerless to end her bottom's persistent torment as she was when Dave was alive, it just somehow wasn't the same. Just making the key's unavailable for a time was no substitute for having someone else in possession of those keys. Someone who may or may not use those keys until they were damn good and ready. Someone whose sadism was just as well developed as Laura's own masochism...