A Proper Young Woman’s Guide to Anal Etiquette - Chapter 14
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.
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Foreword
I’ve decided to switch formats for my stories going forward. Instead of long, 12k to 20k word stories that take multiple sittings over multiple days to complete, I’m going to start writing shorter stories that I can bang out in a single evening. I tend to wander off too much during the longer stories.
Also, I had a big plot arc laid out involving Cora’s birthday with the cast from England, Emily and Cora returning overseas with Victoria to attend Saint Patty Parker’s Finishing School, maybe some visits to Rosa Culo Paraíso with various characters, etc. The problem is that that is a linear plot where I have to write one part before the next part can logically begin. I want to write about whatever fucked up idea may take my fancy at the moment, so I’m going to try and stay away from committing myself to multi-part stories and entangled plots. So, let’s see where all this goes…
On, and I do plan on eventually finishing up the Expo Part III. If I don’t get around to it, I’ll release what I have written so far as part II ½ and call it done.
Family Masturbation Time
Laura Wilder groaned in pain as she tightened down the second Full Force XL nipple clamp that she’d purchased from The Expo several weeks back. She continued tightening the clamp until the pain emanating from the targeted nipple matched that of its sister. Laura stood mostly naked in the Wilder Home’s large communal bathroom in front of the wall-length mirror. The toned 39-year-old mother of five masochistic daughters wore only a lacey, deep purple garter belt, matching stockings, 5” black high heels, a painfully thick punishment catheter, and her horrific nipple clamps. She was preparing for Family Masturbation Time. After all, the family that masturbated together, stayed together!
“You really do love those things, don’t you?” came a question from Amanda behind her.
“Love; and hate,” Laura replied as she choked back tears of pain. “So, you’re headed out then?”
“Yup. It’s date night tonight and Todd is taking me dancing!” replied the 28-year-old redhead happily. The younger woman wore a tight, satin little black dress with a build in leather corset that ran from under her ample 36DD bust to her wide hips. The strapless dress itself covered her from just above her nipples – leaving just a hint of areola – to maybe 2” below her crotch. An inch or so of naked thigh was visible beneath the hem of her dress before being coved by her black stockings. The straps of her garters were clearly visible. Her nearly 6” high heels made Amanda roughly equal in height to her mother. If she were to bend over, anyone behind her would get an eyeful! It was almost too revealing for public. If not for the fact that it was mid-evening and she was headed for the club scene downtown, she could probably have been arrested for indecent exposure.
This wasn’t France or Spain after all! Public nudity and anything to do with anal wellbeing was strictly a social taboo here in America. Of course, neighbors – and especially female neighbors – talked anyway. In hushed voices during early morning jogs or yoga classes, or quietly in supermarket aisles, female neighbors discuss the states of their anal wellbeing not-so-secretly with each other. So, things were changing ever so slowly; but it would likely be decades before the US caught up with Europe’s level of social liberalness. And God only knew how depraved Europe would be when the US caught up to where it was right now!
Todd had been in town after his sales trip finished up several days ago. Laura was a little sad that her extended time with her eldest daughter was coming to an end, as the couple would be returning home in a few days to get back to normal life. It had been years since they’d spent so much time together and Laura was happy for every orgasm they’d had together in the past couple of weeks.
“Are you sure you and Todd don’t want to stay for tonight’s Family Masturbation Time? You came so hard and so often yesterday evening, and I really apricated Todd pumping his load down my throat there at the end. I don’t get the chance to choke on real dick much these days!” Laura said hopefully.
“Sorry, Mother, but Todd and I have reservations,” the buxom daughter explained.
“Well, don’t be out too late then,” suggested Laura despite herself. Her oldest was more than capable of making her own decisions, but she couldn’t help being a doting mother.
“We won’t,” Amanda lied as she stepped up to her mother. Her sexy strut caused her nearly exposed breasts to jiggle enticingly. With each step, her barely contained nipples threatened to pop free. The two met and kissed each other deeply for several seconds while their fingers quickly found their unprotected gashes – Laura was nearly naked and nothing protected Amanda’s pussy once the thin fabric of her dress was brushed aside. Each dipped three fingers into the other before breaking the kiss and licking their fingers off in a traditional farewell or goodnight between close family members.
Todd appeared at the bathroom door in a handsome, well-tailored black suit to collect his bride. “Ready, baby?” he asked.
“Ready!” said Amanda and turned to leave. Laura watched the sway of her daughter’s attractive, full butt as she left. She couldn’t help but notice her daughter’s odd motion as she walked, but didn’t think much of it. Although, when her fingers were inside her daughter, the hard presence of a sizable plug was obvious through the thin membrane separating her daughter’s two fuck holes. Maybe she was still adjusting to its size with her corset compressed waist; or maybe it was the obviously thick catheter in her urethra than Laura had had to work her fingers around to get into the younger woman’s pussy. It didn’t really matter.
“Have fun you two!” Laura called out as the pair turned to leave.
“We will, Mom,” replied Todd as he ran his eyes up and down his mother-in-law before walking over to her to kiss her just as deeply as Amanda had. While he did so, he reached down and thrust two, then three then four of his sizable fingers into Laura’s wet pussy and then lifted her right off her feet. Laura could only groan into her son-in-law’s mouth as her feet dangled uselessly beneath her and her body weight fell entirely onto Todd’s strong hand through her now drenched cunt.
“Now who’s going to make us late?” chided Amanda from the doorway.
Reluctantly, Todd put his mother-in-law down, broke the kiss and turned towards the hallway. Laura only smirked to herself. All men ever wanted was to see a woman naked – and preferably hurt her. Dave had been the same way.
Smiling to herself, Laura turned and stepped out of the bathroom and into her master bedroom. The swaying of her heavy 36FF breasts almost took her breath away as the clamps rolled around on her freely bouncing tits. A thin sheen of sweat still glistened off her mostly nude body from the extra-hot, extra-large enema cycle she’d just completed. She could feel water from her enema drip out of her temporarily empty bottom as she moved.
It was Family Masturbation Night at the Wilder’s and Laura couldn’t wait!
Almost every night for the past two weeks Laura and her daughters has masturbated together – just like a proper, loving family should! She still felt guilty that she had allowed the habit to lapse the last couple of years. Before Dave had passed and Amanda and Marry had moved out, Laura and her of-age daughters had masturbated every night in the living room while Dave watched them from the couch, jerked off and recorded them. Dave normally shot his wad on Laura’s chest so that she and the girls could lick it all up.
Generally, Laura and her daughters masturbated in one of two ways. The first was by attaching a sturdy dildo to the floor, impaling themselves on it and then laying back. With their shoulders on the floor and their arms normally bound underneath them, they would raise up their pelvises with their leg and abdominal muscles to extract the dildos before relaxing and allowing the weight of their bodies to fuck the dildos back deeply inside. While masturbating in this way, they normally wore high heels and knee spreaders to keep their legs spread wide so Dave and the cameras to get a good view of their glistening cunts and the thick dildos being rammed into their backsides. This position also allowed an easy outline of the dildos passages through their rectal tracts as their torsos were stretched.
The other way was with masturbation frames. The girls would lie backwards onto the plastic frames and throw their legs over their heads. By raising the corners of the frames up a couple of inches, each ankle could slip under the brace on either side and behind their heads. A padded bench could then be cranked up underneath their lower back to angle their widely spread butts straight up. Similarly, a padded headrest could be adjusted so that their pussies were about a foot away from their faces. Dave would normally then lock their ankles in place for the duration. Each woman then used a thick dildo with a handle attached and fucked their back holes as hard as they could. Dave was preferable to this method as he could take hold of the dildo if need be to really ram it in deep and hard. It was also easier to swap out the dildos for larger or rougher models if the mood overtook him. The best part was that the frames folded down and could be stored underneath the couch in the living room!
Regardless of the method, Family Masturbation Time lasted for at least half an hour and each woman was expected to continue pleasing herself until Dave was satisfied – in all senses of the word. It had been part of their nightly routine. Afterwards, they’d all eat dinner together, have recreational time for an hour or so, then training and/or punishment time, and then Dave would put first his daughters and then his wife to bed. Of course, it generally took a couple of hours for him to put Laura ‘to bed’. If their daughters weren’t so exhausted from training or punishment time, their mother’s screams of pleasure and pain and her silly, unheeded cries for mercy would likely have kept them up way later than their allotted bedtimes!
Dave had always told her that she looked her cutest when she was begging and pleading with him for leniency while he was working on her anal wellbeing. Of course, he never gave in! He cared for her too much to allow that. If Laura’s cried grew too loud however, Dave would lovingly silence her with an oversized ball gag, kiss the tears from her pleading eyes, retighten her ever-present nipple clamps, and go back to whatever he had been doing his wife’s poor asshole.
Just the thought of their old playtime together was enough for Laura’s already wet pussy to start dripping. She would have loved nothing more than to bring up an old family home video of Dave wrecking her bottom with an oversized punishment dildo and masturbate herself silly; but she had motherly duties to attend to. Although, she did have one particular video in mind for later that evening. Banishing her thoughts for later that night, she finally paid attention to the goings on in her bedroom – and her bald cunt spasmed at the sight.
On her bed were her three youngest daughters engaged in a three-way 69. While three eager mouths were munching down on wet cunts, three fists were buried up the loose backsides right behind the front fuck holes. Although, Cora was busy working her second fist in beside the first in Naomi’s more dilated nether hole. None of them noticed their mother’s presence.
Each wore similar lingerie to their mother along with high heels. 18-year-old Emily and Cora wore deep red stockings and garter belt while 22-year-old Naomi wore a light blue set. They still liked to dress up for each other after all. Each young woman also wore a pair of nipple clamps. Emily wore sever alligator-style clamp on her perky 32B tits – which were very advanced for her age. She was still trying to work up to the horrible Full Force XL’s, but her nipples needed to time acclimate to such extreme pressure. Cora wore a much more sensible pair of basic clamps on her 34D tits. Naomi on the other hand, was wearing a fully clamped down set of Full Force XL’s on her growing 34DD breasts. The middle Wilder daughter had talked her mother into taking her into the Dermott Clinic the day after the Expo for a prescription of Voluptuzym to increase her bust size in preparation for her Gute Nacht Bett. She’d always wanted larger tits anyway. Dr. Veronica had fully supported the decision and written Naomi a prescription for double strength capsules. As was almost expected, Dr. Mark had insisted Laura go through another full examination that he supervised personally. She had spent almost two hours strapped down to a MGC in her friend’s husband’s office being rectally examined by the massively muscled doctor. She’d finally been given a clean bill of health – again – and wheeled out into the hallway by Nurse Patricia.
Shaking herself back to the present she said sternly, “Girls! Enough of that until after Family Masturbation Time!” All three young women quickly detached themselves and stood up at the foot of their mother’s “King” sized Gute Nacht Bett. Although, the German King size was nearly double the American King size. Five people could sleep comfortably on the massive bed with room to spare! Laura had always thought her old King size bed was a little small for the size of her master bedroom. She didn’t have to worry about that anymore!
In addition, when Amanda had found out about her mother’s purchase, she had ordered a smart mattress from her own company to go along with it. Smart mattresses were new devices that turned normal beds into all-purpose bondage, punishment and sex stations. Underneath the comfortable latex mattress was an assortment of programmable robotic motors and winches of various powers and functions. Additionally, robotic armatures could be mounted to hardpoints beneath holes in the mattress to add additional functionality. Amanda’s company – Anal By Design – and the manufacturer of the Gute Nacht Bett – German Sleep Systems – had partnered to sync their two product’s APIs into a seamless user interface. The result was a, “Fully realized, autonomous female subjugation device” – as Amanda had put it after spending the better part of a day setting it all up and adding custom programming for her mother. Laura was still easing her way into all its options and features. She was convinced that if the Germans couldn’t over-engineer something sufficiently enough, Amanda could one-up them!
Mounted onto four the bed’s hardpoints were thickly veined riding dildos sticking straight up. Each was close to its targeted hole’s maximum dilation and almost long enough to slam into the base of the lungs when fully inserted, but not quite. Laura’s was 6.05” wide and 22” long. Emily’s was 3.35” wide and 18” long. Cora’s was 4.30” wide and 18” long wile Naomi’s was 4.75” wide and 20” long. The thickness and rough texture should give each woman considerable enjoyment.
In front of each dildo were some wrist, elbow, ankle and thigh straps, a knee spreader, a thick ball gag some thin wires, and some rubber tubing. “Come on, girls,” Laura continued crossing to the bed, “Let’s get ready to masturbate. We’re going to have some fun tonight! Amanda told me she programmed in a surprise for us!”
All four women smiled in anticipation of the upcoming surprise. “What is it?” Emily finally asked.
“I have no idea, baby,” Laura replied truthfully, “And even if I did, I wouldn’t tell you! Now gear up.” Emily scowled in resignation as Cora laughed at her before joining her sisters and mother in preparation.
* * *
Five minutes later, the four were ready. Spread across the width of the bed, each woman lay with their keens almost touching their neighbor’s: Cora next to Emily, next to Laura, next to Naomi. Knee spreaders held their upper legs at about 90-degree angles. Ankle, wrist, thigh and elbow straps were attached to magnetic cables running into the smart mattress, as were the straps of the ball gags laying on their lips. “Ready, babies?” Laura said at last. Three excited acknowledgments followed. “Okay then. Bed, execute ‘Amanda Surprise 1’ please.”
With the verbal command given, the four ball gags slowly ratcheted down until each head was pressed firmly into the mattress and the corners of their mouths were pulled back painfully. This caused their lips to pull away from their teeth. Then, the gags auto inflated until their jaws felt like they would dislocate. After that, the values auto-released and the rubber tube running from each woman’s punishment catheter to ball gag turned yellow as their bladders drained into defenseless mouths. As each woman struggled to gulp down the torrent of piss, their elbows were drawn together and down into the smart mattress nearly 45-degrees into a moderate strappado while their ankles were pulled firmly downwards so they couldn’t move. Finally, the large 120” TV mounted to the ceiling above the bed came to life and started playing recorded video from a training session years earlier. In the lower corner, a timer started counting up from 00:00:00. Around the edges of the display were several PiPs of the live feed recording tonight’s Family Masturbation Time for later viewing. Four bound women with clamped nipples and wet, bald cunts looked down on them in glorious high definition as they started to lift their bodies up with their stomach and leg muscles to fuck their assholes down onto the thick riding dildos. Their strappados prohibited some movement, but each was able to get into a decent rhythm.
Onscreen, a young Amanda around 20 years old was being held down by a younger looking Laura while Dave worked his fist into her already well-trained rectum. “Tonight, we’re going to go past my elbow, Amanda,” onscreen Dave said. “You’ve seen your mother take my whole arm often enough, it’s time for you to learn this valuable life skill!” Laura remembered that night. It had taken almost half an hour, but Dave had finally succeeded in his quest. She was really looking forward to watching the video; she hadn’t seen it in years!
Glancing at the real-life action going on in the PiPs, Laura could see the four bound Wilder women rapidly raising and lowing their butts onto their sizable anal dildos with enthusiastic gusto. The angle of the dildos and their taut stomachs made each thick toy’s passage from their pelvic bones to underneath their rib cages easily discernable. Laura had to admit to herself that what was going on in real-life on her bed was probably hotter than tonight’s feature presentation.
As the movie progressed and Young Amanda’s cries of pain and begging intensified, it wasn’t long before Laura heard Naomi’s muffled cries of orgasm behind her ball gag. Moments later, Emily sounded off followed by Cora. Laura’s own orgasm was so close! With a few more extra strong downward thrusts, she felt her climax hit at last. She screamed into her gag as she came before collapsing limply down onto the bed in momentary exhaustion. No sooner did she do so than the thin wires that she’d attached to her metal nipple clamps and metal catheter poured electric current into her most sensitive bits. She cried out in pain and began moving as quickly as she could. Within a second of resuming her pace, the electricity stopped. Glancing downwards to the counter, Laura saw it was currently at 00:02:47. They had a long way to go to the half-hour mark!
Onscreen, Amanda was now blubbering uncontrollably as Dave tried as hard as he could to work his elbow past Amanda’s straining nether hole. Onscreen Laura sat on her daughter’s face, twisting and crushing her daughter’s nipples while offering words of encouragement. “Just try and relax, baby. Mommy knows her baby’s orgasm is getting close. Just let it go and you’ll open up for daddy!” Within seconds, onscreen Amanda cried out in orgasm. Real life Laura and her daughters joined her in climax within seconds!
As soon as Amanda came down, she was relaxed enough for Dave’s elbow to finally pass through her battered sphincter. “Good girl!” Dave said happily as he began pulling out a few inches only to punch his arm back into the depths of his daughter’s rectum. “You’ll be taking deep fistings as well as your mother in no time at all!” he commented as his pace picked up and his arm buried itself deeper with each stroke. “Let’s see how far we can go, shall we?”
The minutes ticked upwards as each woman came again and again and again. The coursing current through nipples and urethras became more frequent and of longer duration as the tiring women grew weaker from their continued exertion. By 00:29:15, all four bodies were dripping with sweat and each woman struggled to get enough oxygen through her nose to keep up the motion of her body. Four assholes were by now quite sore and ready for a reprieve and four sets of nipples were screaming for release. Four dripping pussies continued to thrust upwards towards the ceiling as Laura and her daughters continued to masturbate as hard as they could, but they were getting tired.
Onscreen, Amanda’s poor anus was wrapped around the Dave’s widening bicep as he pounded his daughter’s useless hole with all his strength. Finally, Amanda came again, harder than she had the entire video; and then went limp – totally spent.
“Good, girl!” onscreen Laura cooed happily. “Mommy is so proud of her baby girl!”
Dave wiped the sweat from his brow and asked, “Would mommy like to be next?”
“Mommy would!” onscreen Laura proclaimed happily as she slid off her daughter’s face at last.
At 00:30:00, the timer paused and the movie playing abruptly stopped just as the widest part of Dave’s bicep was slipping into onscreen Laura’s well trained behind. It was replaced with another scene from inside the Wilder Home – the guest bedroom where Amanda and Todd were staying to be specific – but this one was recorded an hour or so ago by the timestamp in the upper corner. Onscreen, Amanda was wearing the little black dress and corset she’s left the house in earlier, but the cups of her dress were pulled down to the reveal her firm 36DD breasts. She was strapped to what looked kind of like an inversion board with her legs pulled up and her ankles secured in the same plane as her shoulders, but about 8” or 10” to either side. Her legs made a wide V which pulled her short skirt up to expose her cathetered cunt and empty, loosely gaping anus. Her arms were obviously bound behind her to keep them out of the way. A wide strap went around her thighs to secure her lower torso to the device. Below her was a 5.60” thick, 24” long heavy-grade torture dildo glistening with lubricant.
Laura tried to gasp behind her ball gag as she recognized what the horrible dildo actually was. Dave had mostly stuck to punishment dildos and Laura had only tried light-grade torture dildos a handful of times – and had not enjoyed any of the experiences. She couldn’t imagine the horrible agony such a large, heavy-grade torture dildo would inflict!
“Hi, mom! Baby sisters!” onscreen Amanda said happily. “You’re all showering and getting your enemas for Family Masturbation Time, so Todd and I have a few minutes to try out an experimental new machine I’ve been working one after some research trips to France. This is evidently a tradition for bridal parties and we’re trying to break into the marketspace; and maybe introduce the product into a few more liberal markets here in the US. Anyways, enjoy the show!” she said at last as Todd appeared onscreen with a silencing cock gag. After securing the long gag down his wife’s throat, he activated the machine.
Two padded panels none of the women had noticed hammered downwards onto Amanda’s shoulders and forced her body downwards onto the waiting dildo; and then hammered downward again; and again. The first few inches were easy, but her downward progress became slower and obviously much more painful as the dildo had to rearrange her innards to make its way into her body because of her severely corseted waist. Were it not for the silencing gag buried deeply in her throat, her Amanda’s screams of torture would likely have drawn the family’s attention – and ruined her surprise.
Suddenly, the thigh straps affixed to the four bound women finally came into play. The cables they were attached to were sucked into the smart mattress impaling the women fully on their dildos – and then the dildos rose 2” each! The mattress had concealed the full length of the special toys! Now each thick tool was long enough to push into the bases of their lungs. To make matters more interesting, the newly revealed final 2” of each dildo was studded with light-grade torture texture! As the dildos sunk home fully at last and started to rotate, four astonished cries of pain managed to slip past over-sized ball gags. The dildos kept rising out of the mattress until the strain of the strappados almost became too much – and they continued to rotate and grind the torture texture into four already sore assholes. The actual bases of each dildo were extra wide and covered in studs. No asshole present could accept such width.
The counter un-paused and continued to count upwards. Without warning, the dildos abruptly dropped 6” only to reverse course and shoot upwards again. While that happened, the thigh straps yanked their torsos downwards to meet the onrushing dildos. Four already sore assholes bottomed out against the too-wide, stud covered bases and were forced upwards violently. Electric current began coursing through their tender bits again despite their forced movement.
It was all too much! Every sexual part of Laura was screaming in agony. When her pain-induced orgasm hit her seconds later, it caught her totally off guard. She tensed up and cried out into her gag with all her strength as the waves of orgasm crashed over her continuously. Through the fog of her own continuous orgasm, Laura could just make out the three matching cries of her youngest daughters as their masochistic tendencies overcame them at last.
* * *
Laura barely noticed it was all over and that her restraints had relaxed. The counter was just blinking at 00:47:30. 17.5 minutes. 17.5 minutes they had all experienced near continuous pain-induced orgasms! Laura couldn’t believe it!
It took her nearly a full minute to work her arms out from underneath her and pop out the ball gag. Her mouth was dry from the exertion and she was sore all over. She felt like she’d just gotten her ass kick by some ruthless personal trainer at the gym. “Well, that was… unexpected,” she said at last to her stirring daughters.
“Can we do it again tomorrow?” came a weak question. Laura had expected something like that from Naomi, but was shocked to hear it come from Emily of all people! The girl who three weeks ago didn’t want anything to do with anal wanted to do it again tomorrow.
“Yeah, can w, Mommy?” came Naomi’s expected question.
Laura smiled before responding, “Yes, girls. Of course!” She considered for a few seconds before adding, “Although, knowing what this smart mattress is capable of now, I’m not sure why we need to waste the first half hour masturbating the old-fashioned way…”
Each of her three youngest daughters were taken aback for a few seconds before agreeing with her assertion. It was looking like 47.5 minutes of their evenings for the foreseeable future was planned!
