A Proper Young Woman's Guide to Anal Etiquette Ch. 15

A Proper Young Woman's Guide to Anal Etiquette: Chapter 15

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.

Later that Night

Emily walked sleepily down the hallway from her and Cora's bedroom to the family's communal bathroom to take a mid-night pee. She still wore her red garter belt and matching stocking from Family Masturbation Time earlier, but had taken off her high heels before bed. A plug strap attached to her garter belt ran down between her cheeks through her 3.5" wide, 16" long smooth nighttime retention plug. The strap then parted to lay on either side of her still moist slit as it ran back up to the front of her garter belt. The young redhead idly played with the obvious bulge the long plug made against her otherwise toned stomach as she walked.

Her maximum capacity was up to 3.85" after nearly two weeks of Anal Therapy. She was quite happy with how far she'd come in such a short period of time. She was pretty sure she would be more dilated than Cora was by the end of the summer at this rate! Her goal was 4.5" by September. Zoe Chandler - her anal therapist - had told her that was a questionable goal, but attainable if she practiced hard at night. Cora was only too happy to help and took great pleasure in reaming out her younger sister's widening back hole for an hour or more every night before bed with a thickly veined dildo at or near Emily's current maximum dilation. Despite the pain, Emily came often and hard. She knew her latent anal masochism was developing quickly.

Thinking of Cora, her sister's musky pussy juices were dried on her face from when the two siblings had fallen asleep in a gentle 69. The young redhead ran her tongue over her lips as she walked in fond remembrance for the slightly older brunette's taste. A loud bump in the night had awoken her and she'd realized she had to take a piss. She assumed that her eldest sister and Todd had come back home from their night out on the town. The likelihood of an intruder getting past the family's expensive home security system was remote in the extreme so she wasn't worried.

Sure enough, the couple rounded the corner into hallway ahead of her. Amanda's left arm was over Todd's shoulder and he was almost carrying her as they came. The position caused her left 36DD tit to come halfway out of its cup to expose most of her nipple. Emily noticed a light nipple clamp teasing her sister's fleshy nub. It was nowhere near the level of clamps she or their mother wore, but Amanda had never been a nipple freak like them either. Emily moved to the side of the hallway as they passed to give them room. They both nodded to her as they went and continued their soft conversation.

"Come on, baby. Let's get you in the room. I'm sure you need some relief. Six hours is a long time!" Todd commented.

"Can we just go to bed, baby?" Amanda replied. "I'm tired and sore."

"Nope," replied Todd. "This whole thing was your idea to test out the prototype..."

And with that they were out of earshot, but Emily was almost certain she heard her oldest sister whimper pathetically.

Emily slowed down to glance into Naomi's room. As expected, athletic torture mouse was strapped into her own Gute Nacht Bett. Their mother had told her to take it easy, but the rebellious middle Wilder daughter didn't have to work tomorrow and was taking the opportunity to put her new bed - or possible herself - through its paces. Naomi had obviously been watching the online videos of Helga, the saleswoman from German Sleep Systems that had sold their mother their new beds. Her legs had been pulled backwards so far that they were behind her shoulders. Naomi wore cuffs on her ankles; these had straps on them running to the headboard. Her arms where pulled over her calves and then crisscrossed behind her back where her wrists where cuffed and strapped to the footboard. Naomi's quickly growing 34DD cup breasts were bound tightly at the base with another strap running upwards and supporting most of the lithe 22-year-old's body weight. Her head was pulled backwards by her hair, and her mouth was held wide open by a ring gag set behind her teeth. The headboard and footboard straps where rocking the young woman's body back and forth with powerful, purposeful strokes to fuck her helpless ass with a thick, evil-looking dildo - a dildo that Emily recognized as one of their mother's Schlampenzähmer light-grade torture dildos mounted to the Spin-Drill and Rotator attachments. Emily remembered her mother telling her that Schlampenzähmer roughly translated to, 'Slut Tamer' - a high-end brand of German torture dildos. An additional dildo was mounted to the front of the bed and fed into Naomi's mouth. Every time she rocked forwards on her darkened and bloated tits, the thick oral dildo would sink deeply into her throat. Whenever her butt was fully implanted on the spinning, rotating torture dildo, soft, painful sobs could be heard coming from the suffering woman. These sobs were quickly silenced as the oral dildo was thrust down her throat once again.

Emily only shook her head. Naomi was certainly earning her self-claimed title of Most Masochistic Wilder tonight for sure! Although, if she didn't know her older sister better, she could have sworn that the noises Naomi was making could almost be described as regretful of her self-imposed torment.

Continuing down the hall, she passed her mother's bedroom; but light and sound coming from within caught her attention. Glancing into the dimly lit room, Emily could see her mother bound face-up onto her bed. The large TV mounted on the ceiling above her illuminated the writhing woman quite well while leaving the rest of the room concealed in darkness. Laura's legs were spread wide and pulled sideways into a perfects splits. She could see cuffs on her mother's ankles attached to the smart mattress to hold them in that position. Emily could also make out a thick wedge underneath her mother's hips to lift her bottom off the bed a foot or so and point her spread buttocks straight upwards. The result was an extreme 210-degree splits that would have been in the realm of a contortionist a century earlier, but was a quite common position for modern women to endure. Emily herself practiced a similar position during her daily stretching routine.

Emily crept into her mother's bedroom to investigate further. A robotic aperture extended from a mounting point in the mattress behind Laura's butt and drove a dildo that looked at or near the 39-year-old's current maximum capacity into her mother's wide-open asshole with surprising force speed. Judging from the light glistening off the thick tool, Emily assumed it was a heavy-grit punishment dildo like her mother both loved and hated with equal zeal. What looked to be a standby rack near the armature contained three more lubricated dildos. The first dildo looked to be a recently used heavy-grit punishment dildo while the other two Emily recognized as unused Schlampenzähmer light-grade torture dildos. Emily was a little surprised. Her mother hadn't taken to the new torture dildos like Naomi had.

A second robotic armature mounted next to the first worked a large fist-shaped dildo in and out of her mother's cunt with sloppy squishing sounds. The painful horrible clamps she had worn earlier during family masturbation were on again and crushing Laura's thick nipples. An almost too wide ball gag was stretching her mother's jaws as far as they physically could. As expected, the straps of the gag were being drawn down into the bed immobilizing Laura's head and pulling the corners of her mouth back painfully. A rubber tube extended from the thick punishment catheter secured in the woman's urethra to a nozzle mounted on the front of the ball gag. Emily could see air bubbles in the yellow line slowly make their way towards her mother's mouth as she recycled her own urine.

Glancing upwards to what was onscreen, a younger looking version of Laura was bound to her old bed in a nearly identical manner to her current position. Emily's late father knelt beside his wife's bound form with one fist buried into her puffy red cunt to the wrist and the other was working a large dildo into her upturned rectum. Emily's expert opinion judged it to be another heavy-grade punishment dildo like the one pulverizing her mother's beautiful bottom in real life.

Onscreen, Dave commented absentmindedly - almost rhetorically to himself as he worked - to his suffering wife. "See? It's going in easily now." Emily could clearly see his arm muscles bulging as her father worked the horrible toy in and out of her mother's defenseless bottom. Almost any adverb would describe the motion of the dildo better than 'easy'! "I think you're almost ready for the next size up. I know it'll be a new record for your hungry ass, but I have faith in you that you'll be able to take it with enough effort."

The image of her younger-looking mother groaned pitifully behind the giant ball gag tightly strapped into her mouth. On the bed, her real-life mother groaned to mimic her on-screen counterpart. Now Emily understood the purpose of the pair of pre-lubricated dildos on the standby rack. One looked to be slightly smaller than the dildo violating her mother's ass and the others slightly larger. All were intimidating in both size and texture, but the torture dildos looked more so. She assumed her mother had programmed the bed to switch out the dildos reaming her bottom to correspond to when Dave switched out the on-screen dildo.

She glanced at the bed's main readout. Evidently, Laura was 95 minutes into a 6-hour-long program. The hour-long video her mother was watching was set to repeat four times while the armature ran at 80% power and then another 47:30-minute video that Emily didn't recognize was set to play three times while the armature increased to 90% power, 95%, and then to 100%. She smiled to herself knowing that her mother would enjoy another four and a half hours of rough treatment as the helpless victim of the uncaring robotic devices. She was glad her mother was finding so many ingenious uses for her new bed and smart matress!

Paying closer attention to the various dildos, she noted that the used punishment dildo was 6.10" wide, the punishment dildo in use and the first torture dildo were bother 6.15" wide, while the last torture dildo was a frightening 6.20" thick. All four dildos were 24" long. The armature was running the current dildo into her mother's obviously sore rectum until it was fully seated and then back out again until only a couple of inches remained inside. Emily knew her mother's current maximum dilation was only 6.15" wide, so that finally torture dildo was going to hurt an awful lot!

Suddenly, the armature stopped it's powerful thrusting. Emily froze thinking she's messed something up, but immediately relaxed as her father's voice floated down from above her. "See, the larger dildo is going in pretty easy," commented Dave. Glancing upwards, Emily saw her strong father forcing the too-large dildo into his beautiful bound wife's bottom with both hands. "It's slipping right in..." Onscreen Laura cried out helplessly into her ball gag and uselessly tried to thrash out of the way. Mimicking the onscreen behavior, the armature extracted the punishment dildo out of her mother's ass, set it on the rack, attached itself to the identically sized torture dildo, lined it up with the large, gaping hole and buried it to the hilt in a single motion. Real-life Laura cried out in obvious pain behind her oversized ball gag as the light-grade torture dildo ravaged her tender insides in a way that mere punishment dildos never could. The armature quickly resumed its previous pace as her mother resigned herself to her horrible, self-imposed fate. Emily was momentarily transfixed by the soft humming sound her mother's anus made as the torture dildo sawed in and out of her body. It sounded like dozens of rubber bands being strummed at the same time. She'd never heard an asshole make that noise before.

Emily shook her head and quietly backed out of the master bedroom so as not to disturb her suffering mother. She kind of hoped she was still awake in an hour when her mother broke fresh territory with the 6.20" dildo.

* * *

"No. Please," complained Amanda softly. She was mounted back on the fitting machine she had been on earlier when she had been jackhammered down onto the maximum capacity, heavy-grade torture dildo before going out for a night on the town with her husband. The base of that same dildo was firmly reattached to the machine. She still wore her little black corset dress, but her still cathetered pussy was on full display again. Also, thick bands had been ratcheted down onto the base of each DD breast. "Can't we just go to bed? It's after midnight."

Todd didn't answer at first as he finished setting up the video cameras that would record the rest of the prototype fitting machine's latest test run. Finally, he replied, "Nope. This is too good of an opportunity to see if the fitting machine's new auxiliary motor is powerful enough; and besides, your bottom hasn't been really worked out since we were home together several weeks ago."

"But Cora and Emily pounded Mother and I's asses pretty good just two weeks ago," the restrained redhead protested. "I even got to a new maximum dilation!"

"Yes, you did," confirmed her husband, "And you're wearing your new 5.60" size right now. I help insert it, remember?" he asked as he finished what he was doing. Red lights illuminated on the four cameras surrounding her to indicate a live recording. Stepping over to the bed, he retrieved the silencing gag he'd used earlier that evening and approached his pouting wife. God! She looked so beautiful! Her full figure compressed by the tight corset and her large bound and reddening breasts excited him. Todd felt his dick hardening. He wanted to pull her down and make sweat love to his wife too; but he didn't. He couldn't help but bend over to give her a deep kiss before silencing any additional protests with the long, thick cock gag. He then attached the rubber hose coming from her catheter to the nozzle on the gag's base and released the clamp.

Amanda couldn't help but sigh with relief as the immense pressure in her bladder subsided at last. She couldn't swallow with the cock gag lodged in her throat, but her urine washed over her tongue before draining out of her moth down the dildo's hollow core and into her stomach.

Without giving his wife a chance to adjust, Todd activated the fitting machine's secondary function. Slowly, the padded board she was strapped to rose unstoppably upwards - while the thick heavy-grade torture dildo lodged in her rectum remained stationary. Amanda tried as hard as she could to scream out in agony, but no noise was heard. The silencing gag directly interfered with her vocal cords. Being denied the ability to even scream was the ultimate humiliation!

Todd crossed to the room's queen-sized bed, stripped off his boxer shorts and laid back to enjoy the sight of his suffering wife and stroke his rock hard, 10" dick. It didn't take the machine long to build up to its operating tempo. Amanda was being forcefully pounded up and down onto her maximum diameter heavy-grade torture dildo with appalling force. Her bound tits were bounding so hard that they were nearly smacking her in the face. Todd knew she was going to be out of commission tomorrow while she recovered, but that was okay. Her pussy would still be available for his dick to fuck.

It was then that he noticed the shadowy figure of Emily watching her sister suffer from the doorway. He couldn't help but notice that the 18-year-old cutie had three fingers buried in her cunt as she observed. The young woman was more petite than Todd preferred, but right now, he so horny that he would fuck just about anything.

"Hey there, kiddo," Todd said loudly, shocking the young voyeur. "Care to join me on the bed? You can get a better view from here."

It only took Emily a few seconds to reply, "Sure!" and step into the bedroom.

* * *

Five minutes later, Emily groaned in pleasure as she rode Todd's thick cock deep into her teenage pussy. Her smooth 3.5" wide, 16" long nighttime retention plug had been swapped out with a 3.75" thick, medium-grit punishment dildo that was mounted to the bed underneath Todd's muscular butt. Every time he thrust upwards into her young body, she would jolt upwards, only to fall back down onto his thick shaft and the much thicker dildo that was reaming her nether hole raw. The powerful nipple clamps he'd placed on her already sore nubs had hurt horribly at first, but now only added to her growing pleasure.

"God! You are so tight with that dildo in your asshole!" moaned Todd as he gave the young woman a series of powerful thrusts. Emily only cried out in pleasure as her brother-in-law roughly fucker her front hole.

In the corner of the room, Amanda continued to be jackhammered up and down onto her heavy-grade torture dildo - momentarily forgotten. She would have been pissed where it not for the massive pain-gasm she could feel building from deep inside her ravaged body.

* * *

"See, the larger dildo is going in pretty easy," commented Dave from above her. Laura tried to cry out and thrash, but she had restrained herself too well and the smart mattress was unforgivingly strong. Her bottom hole had had enough. After three and a half hours of rectal abuse - the last hour of which being the rarely used Schlampenzähmer light-grade torture - she was done.

Onscreen, Laura's late husband was forcing the too-large dildo into her younger self's bottom with both hands. "It's slipping right in..." The robotic armature that had been tirelessly fucking her asshole stopped and extracted the 6.15" wide torture dildo out of her spasming hole. Laura's efforts redoubled as the final 6.20" light-grade torture dildo was retrieved and lined up with her defenseless sphincter. Without pity or remorse, the robotic armature rammed the almost too big dildo into Laura's hole as best as it could; but it still took nearly a minute for the tool's full length to bottom out. Laura screamed as loud as she could behind her too large ball gag as lights danced in her vision.

Dutifully, the armature slowly worked itself back up to its normal operating speed over the next half hour. Laura continued to moan in pain, even after the three orgasms she experienced. The fist-sized dildo that was still wrecking her dripping cunt barely registered anymore.

Finally, the video of her and Dave ended and the video that had been recorded of Laura and her three daughters masturbating earlier than night started. At the same time, the horrible torture dildo sawing in and out of her asshole picked up speed and force noticeably. It was all too much. The pain shooting through her body. The images onscreen of her and her daughters ramming their butts down onto their riding dildos. Laura came harder than she had in what seemed like years as the pounding of her holes continues without interruption. It lasted for almost a full minute.