A Proper Young Woman's Guide to Anal Etiquette Ch. 13

A Proper Young Woman's Guide to Anal Etiquette: Chapter 13

By: Lord Odie

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 Note

This story is still incomplete, and I have not touched it in years. I might complete it one day, but not likely. My imagination has wandered away to other characters who need my attention more.

My writer's block on this chapter is one of the contributing things as to why updates stopped, even though I have continues writing other stories in this setting. So, I'm calling this done for now and moving on.

Previously in The Expo, Part II:

While browsing the Expo's many wares, Laura met up with a new friend. Now, onward to Anal by Design!

The Expo, Part III

Next up, Laura managed to pass by the booth of Parisian Plugs without stopping. The company sold designer, name brand plugs. While she thought their soothing floral patterns and exciting color motifs were nice, she was not going to pay five times the cost of a normal, retail plug just to get a fancy logo emblazoned on the bottom. However, judging from the long line of women browsing the large booth's shelves and lining up at the cash registers, she was in the minority on that opinion. She sighed to herself as her trek continued.

Not too far down from the superb example of capitalism at its finest was a booth Laura had to stop and take a look at: Anastasia's Secrets. The company had been named after a character in a trilogy of softcore BDSM books from earlier in the century... which Laura couldn't remember the name of now. Damn it! Laura scolded herself. Those books had been high school required reading for second year senior American Literature for decades. Oh well, she'd remember the name later.

Anastasia's Secrets had been her and Dave's go-to store for the more severe items in her massive collection of plugs and dildos. After all, they specialized in providing bondage equipment, leather and latex apparel, anal training gear, extreme enema paraphernalia, and a host of other fun items. Most of her punishment and torture dildo sets - and more than a few nipple clamps - had been purchased from their website and retail outlet store a few cities over. Dave had actually bought her a gift set of their Please and Pain torture plugs for her fortieth birthday. She hadn't dared to actually play with them in years. They scared the hell out of her when she was forty and Dave was experimenting to see which coarse texture caused her to cry out in the most pain, and they still scared the hell out of her today years later!

Although, maybe Amanda and I could bring them out of retirement this weekend, Laura thought to herself mischievously. Her sphincter spasmed around her Dilation Master XXL in involuntary protest at the mere thought. To be honest, she was pretty sure her anal dilation had regressed to a point where those toys probably wouldn't go in without a significant investment of time and energy on Amanda's part. Which would be fun! Laura admitted to here self as her anal ring spasmed again.

As Laura pushed her way through the on looking women outside of the booth, the first thing she saw was a raven haired saleswoman fielding questions about the demonstration she was giving. She was tall; a few inches over six feet. The heels of her crimson, thigh high latex boots pushed her head up another five inches so that she was towering over the gathered women. Above the boots were just a few inches of skin before the black material of what looked to be old school latex panties covered her nether region entirely. Laura thought that a little odd as full panties had gone out of fashion when her grandmother had been young. Modern underwear was either of the crotch-less or gaper varieties - or some kind of variation - or just part of every woman's plug strap.

Above the odd looking underwear was a matching, severe looking crimson latex corset with thick black boning. Considering the woman's above average height and stocky build, the narrowness of her waist as the corset crushed inwards was impressive. But not nearly as impressive as her G or H cups breasts as they spilled out of the garment's built in quarter cup bra! Each massive mammary was topped with a rock hard nipple pierced with large stainless steel barbells in the center of wide, pink areolas. Laura's mouth immediately started watering as she imagined sucking on each one. Completing the saleswoman's look: her arms and shoulders were bare, her face was strong and unyielding and her black hair was pulled up into a tight bun on the back of her head. She looked like the quintessential mistress out of every woman's fantasies; or nightmares to be more accurate.

As she broke into the front of the crowd, she was able to see the details of Mistress's 'outdated' panties more clearly. Ah! She'd seen these before online. They were actually universal chastity panties. With her close proximity, she could now see the built in rubber grommets securely holding the dildos in place. The base of the pussy dildo looked to be an imposing four-and-a-half or five inches in diameter while the urethra dildo must be nearly an inch wide! From her vantage point, Laura couldn't see the anal dildo clearly, but from what she could see of its base between the sexy two-inch gap between Mistress's legs, it was equally massive. Laura briefly wondered where the woman's internal organs were considering the sheer size of the dildos secured into her three lower holes and the crushing restriction imposed by her boned corset.

Mistress was standing behind a standard waist high bondage bench and gesturing towards the bound woman on it as she talked. Unlike Mistress - who was decked out in full dungeon attire - the bound woman wore street clothes and had most likely been a volunteer from the audience for this demonstration. She was situated on her back with her wrists secured to the top of the bench. Her gray dress slacks had been pulled down to her ankles and her legs had been double up and positioned over her torso. Straps built into the bench held her knees and legs tightly against her sides, which caused her feet and bunched up pants to rest over her face. Laura could see the woman's brown hair spilling out over the bench though. She still wore a deep blue, low cut silk blouse that covered her sizable breasts. A sizable triangular shaped pillow was under her hips and lower back, which pointed her bubble butt upwards towards the ceiling. Underneath her raised ass, Laura could see a pair of leather straps hanging down towards the bench - the thick dilator dildo they had been securing was sitting at the foot of the bondage bench; which she estimated was nearly six-inches wide. This was a lady whose anal wellbeing was being nicely looked after!

Inserted into the prostrate woman's upturned bottom was an evil looking blue dildo approximately the same thickness as the dilator she had been wearing before the demonstration, but of unknown length; though there was at least ten inches still outside of the woman's body. Mistress left had gripped the handle at its base as she absentmindedly worked the toy around inside of her temporary assistant's defenseless asshole.

"Now pay particular attention to the sounds of exquisite agony from my assistant here as the tiny pyramids of the Nefertiti's Pleasure torture dildo pull past her sphincter on the way in and almost turn her anus inside out when you pull back out," Mistress said as she demonstrated by grabbing the dildo's handle with both hands to very slowly work it in and out of its confining hole a few inches in either direction. "Even though each pyramid is only raised about five millimeters off the surface of the dildo, that's still plenty to get a really decent grip on your rectal tissues." The woman on the bench went visibly rigid and groaned in obvious pain as the nearly six-inch wide torture dildo passed through her sphincter and deep into her rectum. "This is because of the patented, lubricant-resistant latex material used in the construction of the tips of the pyramids. While lubrication still aides in insertion and intercourse, each pyramid type will grab at a woman's sphincter and rectal walls and almost pull them along for the ride. Trust me when I tell you that the sensations it causes are most... unpleasant," Mistress added with a slight shudder which she almost succeeded in hiding from the more observant members of her audience - Laura noticed it though.

Sure enough, on each downward stroke, the sphincter on the woman completely disappeared between the mounds of her nicely shaped derriere. On each upward stroke, the abused ring of red muscle was pulled upwards - almost past those same, beautiful butt cheeks - to form a cone of flesh centered around her asshole. Laura admitted it looked most excruciating, while at the same time wondering how much a set of these devilish devices cost. The soft groans and whimpering coming from the bound woman was making her pussy start to drip and her ass ache for some similarly rough treatment.

"The sensations only intensify if you start adding twisting motions to the strokes," Mistress added after about a minute of slow repetitions.

A weak, "Owwwww... Fcuk..." could be heard from the woman's covered face as Mistress grabbed the handle with both hands and added twisting to the thrusting and the pace started to increase slowly. Laura thought the voice sounded oddly familiar, but was getting too interested in the demonstration to pay it much mind. Each downward stroke of the dildo was a fraction of an inch longer than the upward stroke, and the dildo was slowly sinking into the bound woman. By now, only five or so inches of the dildo remained outside of the upturned butt.

Various women in the audience were asking technical questions about the demonstrated device:

"Is the toy plug washer safe?"

"Yes; but I wouldn't exactly call the Nefertiti a, 'toy'!"

"Is there a suggested minimum age?"

"Eighteen, with parental supervision of course."

"Can my wife wear it to work like a dilator plug?"

Mistress paused for a few moments before replying with a smirk, "Prolonged insertion really wasn't the primary design, but I don't see why not..."

"Can I get a set gift-wrapped?"

"Of course! Our sales consultants will take your orders anytime; or you can buy online."

On and on the questions went. All the while, Mistress continued pulverizing the defenseless bottom of the bound woman. By this time, the torture dildo had bottomed out and the flared portion of the tool's pummel was slapping into the ruined asshole with each downward thrust.

"Ah, yes. You'll notice that the last inch or so of the Nefertiti's Pleasure is covered in smaller, sharper, more closely spaced pyramids," Mistress said in response to one woman's question. "This makes wearing the plug fully seated truly torturous as the sphincter is basically treated as a pin cushion! Although, we do have a few more advanced models that have this pattern running along the entire length of the tool," she added with an evil grin.

As the question and answer portion of the demonstration dragged on, the woman's sphincter was starting to give out and her rectum was being pulled past it to make a slight prolapse with each outward stroke. The woman's constant sobbing and moaning were only being interrupted as the blue dildo slammed into the base of her lungs; which solved Laura's question about its total length: just long enough! Laura was trying to determine whether she pitied the bound woman or envied her; a little bit of both if she were honest with herself.

"Any more questions?" Mistress asked at last; breaking Laura's concentration. There were none. "Well then, why don't we get our helper off then, shall we?" she asked to a murmur of agreement from the crowd. With that, Mistress looked away from the crowd for the first time to focus on the upturned ass in front of her. With both hands on the dildo's handle, her pace doubled; and then doubled again. Over twelve inches of thick, pyramid-studded latex emerged and quickly sank back into the now openly crying woman's destroyed asshole. The ruined ring of muscle between her buttocks was emanating a low hum of sound - like a thick rubber band being plucked repeatedly at high speed. Droplets of lubrication were occasionally flying off the dildo to splatter onto the woman, bench and Mistress's heaving tits. The leather clad saleswoman's large breasts were bouncing heavily in cadence with her motions. To Laura, it looked like a latex clad milkmaid was churning ass-butter with a maniacal enthusiasm!

Mistress commented to the crowd without looking up, "Now just imagine yourself in the same position as Melissa here and remember that your torture session has only just begun. If you have a husband, wife, boyfriend, girlfriend, son, daughter, roommate, or - hell! - just a close acquaintance who cares enough about your anal wellbeing, your torture sessions could last for hours on end. Just listen to the soft cries of agonized despair and just think: this could be you when you get home tonight!"

God! Laura wished it would be! She could feel pussy juice running down her legs and wish she could touch herself. Glancing around quickly, she could tell that most of the women in the audience were having the same reaction as she was. If she didn't know any better, she would say that the level of anal masochism was reaching epidemic proportions at the Anastasia's Secrets booth this afternoon!

Wait! Did she say, 'Melissa'? That familiar voice! Could it be...?

Before her train of thought could continue, Laura heard all the gathered women holding their collective breaths as the bound woman tensed for a few heartbeats before letting out a guttural cry of ecstasy. A small gush of pussy juice pulsed out and ran down her abdomen and onto her waist cincher. Mistress quickly wiped it up with a towel before it reached her blouse - which had bunched up underneath her heaving breasts - and then continued pounding the woman's poor asshole for another thirty seconds or so, refusing to allow her to come down from her mind shattering orgasm.

Finally, Mistress buried the toy to the hilt inside the upturned bottom and let go. "Thank you all for watching our little demonstration of the Nefertiti's Pleasure series of torture dildos. Can we get a round of applause for my helper, Melissa?" The crowd applauded enthusiastically. "For her assistance today, she gets to keep the demonstration Nefertiti's Pleasure as her free gift!" The applause continued. "Please browse through Anastasia's Secrets' booth, but be back here in half an hour for our next demonstration: the all new and redesigned Please and Pain™ 2.0 line of torture plugs with coarser textures and larger sizes guaranteed to bring out the anal masochist in all of us! Thank you!"

The applause continued for a few seconds before dying down as most of the women in the crowd made their way into the Anastasia's Secrets booth. Laura advanced upon Mistress and 'Melissa' to see if it was the same 'Nurse Melissa' she'd met earlier this morning at the Dermott Clinic. After all, the clinic had closed at 11:00 this morning so that the entire staff could attend the Expo, so it was possible.

"Thanks again for your help, Melissa," Mistress was saying softly to the bound woman as she bent over. "You can be my little fuck-slave any day!" she added playfully.

"You're welcome," came a weak reply that Laura recognized immediately. What were the chances?!

Mistress continued, "Would you like your free gift-wrapped, or would you like to wear it out?"

A few seconds passed before Laura heard a slightly less shaky response, "I'll wear it, please."

"Such a good little masochist!" commented Mistress as she playfully slapped Melissa's butt cheek. "I hope you have someone at home who will use it properly."

"Not yet, but I met someone this morning who I'd like to give the chance to," she answered as she giggled. Laura felt her face blush. She would indeed love the chance to abuse Melissa's nether hole with her new torture dildo!

"Well, I wish you the best," Mistress replied as she stood up, disconnected the Nefertiti's handle and gathered up Melissa's dangling plug straps. Passing each strap through the plug's base and on either side of the pubic mound, Mistress then pulled the straps tight - which forced the sizable plug even deeper into Melissa's distended bowels - before buckling the straps securely in place. Melissa grunted in discomfort as each strap was pulled snug. Her puffy, post-orgasm snatch looked even more delicious as it was compressed between the two straps on either side. Laura couldn't help but lick her lips.

With the new plug secured, Mistress released Melissa's legs and wrists and helped her slide off the side of the bench to her feet. Melissa held onto the bench for several seconds as she adjusted to her new, upright position. Slowly and gingerly, she bent down to retrieve her slacks - which were pooled around her ankles. She grunted heavily as the torture plug moved around inside of her body and knocked the air out of her lungs. Exhaling fully, she bent down again and succeeded. As she worked her slacks up and over her amazing ass, she commented to Mistress, "God! You have no idea how this really rips into you with every little movement! The sphincter is the worst! I remember you saying it had a special pattern, but fuck!"

Mistress laughed. "Oh, my sweet, little slave! What do you think all three of my holes have been plugged with since 6:00 this morning?"

"No! You're not serious!" exclaimed Melissa. She had been straightening out her blouse and repositioning her 34FF's after they'd bounced around inside her bra when she came to a dead stop to stare at Mistress in disbelief.

The latex clad dominatrix turned and belt over slightly to give Melissa a view of the base of the anal dildo secured in place by the chastity panties she wore.

"Holy fuck!" Melissa gasped as she read the imprinted Anastasia's Secrets and Nefertiti's Pleasure logos imprinted on the base. "And six-and-a-half-inches too!"

Mistress smiled and turned back around to give Melissa a view of the bases of her front two dildos. "The vaginal dildo is actually in the shape of a rounded crescent that wraps around the anal dildo so that it actually fits into my body. The urethra dildo is just a normal cylinder," she added.

"My God! Five-and-a-half-inches in your poor pussy and one-and-an-eighth-inches in your pee hole? How are you still standing after all these hours?"

"Lots of practice, my little slave. It's what I wear to work every day," answered Mistress. And with that, Mistress smiled, turned and walked into the booth with a debonair sway to her nicely shaped hips to start making sales. Melissa knew that sexy sway would undoubtedly cause the triple torture dildos buried in the tall woman to grid her tender holes painfully; but Mistress showed no signs of any discomfort at all.

Both women were temporarily memorized by the delightful sight of departing saleswoman before Laura regained her composure enough to say, "Hello, Melissa."