A Proper Young Woman’s Guide to Anal Etiquette Ch. 05

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

Previously in Déjà Vu, Part I:

When last we left our heroines, they were fighting for their lives against the impending Martian Zombie Invasion… Err… I mean ensuring that their anal health was properly looked after. (If I made the incorrect choice of narrative, let me know.)

Amanda had come to the realization that she needed to spend more time with her family and Laura had been busying herself with being a very naughty girl. Certainly not the type of role model she should be for her daughters. It’s time for Amanda to set her mother back on the straight and narrow!

Or, more appropriately, the wide and gaping…

Déjà Vu, Part II

It had been a close thing and Amanda knew it. One or two more ” Can mommy’s little girl this” or “Can mommy’s little girl that” and Amanda would be picking out the largest heavy grit punishment plug she could physically take and presenting it to her mother to be brutally buggered with instead of the other way around. She couldn’t help it. The reaction was almost instinctual. And there was a yearning part of her deep down inside that longed to remove the ball gag from her mother’s mouth, fill her own mouth with the red rubber orb and start sifting through the punishment plug collection for something appropriate for an uppity daughter who was presumptuous enough to try and punish her own mother. And she knew Laura would be more than willing to accommodate her request.

But she quieted that desperate inner longing. After all, her mother did deserve to be punished. And while Amanda was sure she could invent some dastardly offense to require such punishment of herself, that would have to wait till later. Perhaps a tag-team punishment session with Cora and Emily? Amanda proposed the idea to herself theoretically. Her tautly stretched anal ring spasmed at the very thought of being pounding by a horrendously sized punishment dildo by her two firm-bodied teenage sisters; taking turns so they didn’t wear out quickly of course; a tag-team like that could last quite a while, after all. Amanda felt her pussy moisten noticeably at the thought, while her sphincter continued to clench up at the excruciating prospect, but both orifices by now knew the decision had already been made. There would be no Wilder rectums fit for play by the end of this night!

But Amanda had to return her attention to the asshole at hand for now. Her own would have to wait its turn.

Finally, the massive head of her mother’s impressive daily dilator slipped free of its fleshy bonds. The juicy pink hole leading up into her mother’s abdomen remained nearly as broad and as deep as the five and a half inch wide, eighteen inch long dilator plug that had just vacated the older woman’s posterior. Such gorgeous sights reminded her yet again why extreme female anal dilation was so common in today’s day and age. It was just too damn hot to be otherwise! To think of all the millennia of tightly closed and unpenetrated rectums the human race had had to endure before it collectively came to that conclusion often baffled her. What a savage species humans were!

Amanda reached past her mother to place the impressive rectal trainer on top of the dresser so that it was out of the way for now. With both hands now free, she slipped her fingers between Laura’s toned ass checks – allowing just the tips to slip inside the worn-out hole – and pulled them as widely apart are she could. The huge ass-chasm that greeted her was indeed awe inspiring. Amanda could swear she could see far enough up her mother’s bum to observe her diaphragm contracting and releasing as the older woman breathed. The sight of her mother’s gaped and ruined anus brought Amanda back to one of her favorite training sessions that she shared with her mother. It was her favorite because it was the first time – certainly not the last – that Todd had joined them. And as obscenely gaped as her mother’s rectum was at this very moment, the sloppy bottomless black hole leading into the deep recesses of her body was nothing compared to the dimensions it had achieved by the end of that training session!

As Amanda released her mother’s desecrated anus – noting that it didn’t even try to fully close after her fingers stopped prying it apart – to rummage through the open drawer for a few more pieces of bondage gear, she allowed her memories to replay that night for the thousandth time.


“Good kadıköy escort girl, Amanda! Mommy knows that that’s an awfully big dilator plug for her baby girl’s deprived little bottom, but you took it without too much crying and hardly any begging. Perhaps it’s almost time to step up your maximum capacity to the next size, but we can discuss that during tomorrow night’s training session. Now, no arguing with your mother! Mommy’s backdoor is packed to its maximum capacity just as painfully as yours is. Or did mommy’s little girl forget already? I swear, baby! Mommy herself just got done crying from her sadistic daughter forcing that huge dilator plug up mommy’s poor butt. If mommy didn’t know any better, she would think that her baby girl actually enjoys watching her mother cry and beg for mercy!

“At least I hope she does. Mommy knows she really enjoys watching her pretty daughters beg and grovel. And you were such a good girl for not giving mommy the mercy she was begging for! After all, as much noise as mommy made with her silly protests it all fit in, didn’t it? Right up to the base!

“Now that we’re both stretched to our maximum capacity, let me text that darling boyfriend of yours so he can come in here and help mommy with the next part of tonight’s lesson. As mommy told her beautiful girl before we started, she needs to be punished for scoring a D on her multi-variant calculus test last week. That was naughty of mommy’s little girl to try and hide that test grade from her loving parents. Mommy and daddy love our baby girl and want to make sure she is successful in her career; and college is very expensive. You need to spend more time studying and less time suckling cum out of Todd’s amazing cock. There’ll be plenty of time in the future for him to ram that handsome penis of his down your throat. If he’s really that horny, tell him to come by the house more often and he can use Mary all he wants. That’s what good sisters do for each other; they make sure that their boyfriends never have to be deprived of willing holes to fuck.

“Oh, hello Todd. I’m glad you could join us. We were just discussing your needs and…

“Well yes. Of course mommy meant her own wet fuck holes are available to you whenever you want. You’re mommy’s oldest daughter’s boyfriend after all, and that makes you practically family! We were…


“Patience, Todd. You can play with Mommy’s pussy later. Well, maybe just a little bit longer…


“Okay! That’s enough for now, Todd… We need to…


“Oh! My! Mommy’s pussy is so wet…

“Oh! Mommy’s future son-in-law can certainly play will her hot cunt anytime her wants to!

“Of course mommy will lick all the sticky cum off of your fingers. Mommy is the one who dirtied them in the first place. […]

“Now where was mommy … Oh yes! Now, Todd, if you’re going to date mommy’s naughty little girl seriously, you must know how to punish her appropriately. A woman needs constant reminders on proper behavior which includes frequent punishment. Mommy and her wayward daughter have spent the last hour or so dilating each other to our current maximum capacity for this lesson.

“Why thank you for noticing, Todd. Mommy does have quite a large dilator up her needy bottom. It took years of hard training for her to take such a wide tool. Daddy is always good to mommy and he still keeps buying his loving wife larger and larger dildos for her flexible backside. Perhaps with a lot of work you could get Amanda as open as mommy is! And wouldn’t that be fun!

“Now for tonight, you’re going to practice your technique on mommy first to make sure you know what you’re doing. Then mommy and Amanda will switch places and you can show mommy what you learned.

“Now before we begin, we need to restrain mommy securely. Normally, mommy would never dream of interfering with anyone as they play with mommy’s loose asshole, but some of the punishment dildos we’ll be demonstrating on mommy tonight are quite painful. Sometimes mommy can’t help herself and tries to either pull away or block access to her naughty hole. This sort of behavior is unacceptable, and mommy would deserve more severe punishment for such bad manners, so to prevent it we won’t give mommy the option.

“The first thing we need is the arm binder on the dresser. See how mommy puts her arms behind her back and her elbows touch easily? Mommy spends a lot of time in her arm binders playing with daddy. Lace the binder all the way up; tightly. Pull a little tighter. No, Mommy’s shoulders can’t touch but they can come close. There you go.

“Of course you can play with mommy’s tits when you’re done. It’s not like mommy can stop you! Just be sure to be rough; this is supposed to be punishment for mommy. Uuuunngh! That feels nice. Be sure to hurt mommy’s nipples too; mommy loves it when her nipples are played with roughly. Aaaaaagh! Oh yes! Mommy’s pussy is getting wetter!

“Amanda, go get Todd a nice set of nipple clamps for mommy’s tits. The alligator clamp ones with üsküdar escort the strong springs.

“Now, Todd. While not necessary for proper anal punishment, some women love to have their nipples clamped while they’re punished. Mommy is one of those women. Mommy’s oldest daughter isn’t (yet); but hopefully she’ll learn.

“Aaaaaahhh! God, that’s good. Now the other one…


“Fuck! That smarts! Thank you, Todd.

“Okay, now that mommy’s arms are out of the way, lay mommy back on the bed and push her legs up and back as far they will go. Use the straps attached to the top of the arm binder to buckle mommy’s legs in that position. Ooompff… Mommy’s legs can come back just a little farther. Oooooooompff! There you go! Daddy always likes it when mommy’s ankles are right next to her head like this. Make sure the clasps are secure. Good job, Todd. With mommy restrained like this, both of mommy’s bottom holes are held wide open and defenseless; the way a woman’s holes should always be for her family!

“Next, unbuckle mommy’s dildo strap and pull out the dilator plug locked up mommy’s stretched out asshole. See how smooth it is? This is because it’s designed to stretch a woman’s backside; not punish it.

“Why thank you, Todd. Daddy has always loved the way mommy gapes open disgustingly when she’s dilated to her maximum size too. You two have so much in common! No wonder you get along so well!

“Now go over to mommy’s dresser and open the second drawer from the top on the right. These are mommy’s medium grit punishment plugs. Select the one that is the same size as the plug you just took out of mommy’s ass. Now notice how this plug is covered in small pointy triangles? This will hurt mommy a lot when you fuck her with it in a few minutes. These triangles will grab and pull at mommy’s poor anus and tear at her sore rectal walls, although this plug is designed to inflict pain on a naughty asshole without actually damaging it.

“But don’t let the moans and gasps of pain you’re about to hear fool you. Most women cum very hard when we’re punished anally; don’t let any of us tell you otherwise. Least of all mommy’s precious daughter. She cums harder than mommy does!

“Now line it up with mommy’s gaping butt hole and start forcing it in. UUUUNNGGHH! God, that hurts! UUUUNNGGHH! Make it go in all the way, Todd. UUUUUUUNNNGGHH!!

“Good boy, Todd. Most punishment plugs have a small neck at the base to let a woman’s asshole close in around when it’s fully inserted. Mommy just felt her sphincter close around it so now we’re about ready to begin mommy’s punishment.

“But before we start, go back over to the dresser and grab that ball gag mommy laid out earlier. Mommy doesn’t want her cries to hurt her future son in-law ears while he’s punishing mommy’s sloppy ass. You’ll have to press hard to get the rubber to seat behind mommy’s teeth.

“Oh! One more thing before we begin. A proper punishment should last at least fifteen minutes, but can go on for as long as is appropriate for the offense. Now since mommy hasn’t really been naughty lately, and daddy wants to punish mommy later tonight for letting her baby girl get such a bad math grade, we’ll just stick with the basics for this evening.

“Now a proper punishment fuck should be hard and fast. Pull the plug out about half way or so before slamming back into mommy’s ass. Don’t be gentle; this is supposed to be a punishment. Just find a rhythm that’s comfortable for you.

“Amanda, be a good girl and fluff your boyfriend while he punishes mommy’s butt.

“Now go ahead and plug up mommy’s slutty mouth and punish her naughty ass. Mommy talks too mu…









“Thank… thank you, Todd. That was very ob-observant of you to realize that mommy… that mommy was still cumming very hard after only fifteen minutes. Mommy thinks you did the right thing to fuck her sore bottom with the punishment plug for another ten minutes or so. Mommy will be very sore before daddy’s punishment session tonight even begins.

“No! Of course daddy won’t go easy on mommy tonight. Why should he? It’s not his fault mommy’s ass has already been punished! Really, Todd. Pay better attention.

“Now that the punishment is finished, it’s always important to show that you still love mommy even though you had to punish her. So lock the punishment plug deep up mommy’s ass and buckle it in securely to hold it in place.


“Yes. Like that. Now fuck mommy’s hot pussy with that amazing cock that Amanda’s been feeding down her throat for the past half hour. Mommy needs to cum some more.



“Fuck mommy!


“Fuck! You really do love mommy!

“Yes! YES! Mommy’s cumming again! Oh, Todd! Oh, Todd! Aaaaaaaaahhhhh!


“That was a very nice fuck, Todd. And a very good practice. Now untie mommy so that you can punish her naughty tuzla escort daughter. Let mommy’s legs down slowly. Give mommy a minute to get feeling back in her arms and legs.

“Now mommy just needs to unplug herself and… Todd! Mommy doesn’t need a padlock on her dildo belt. Mommy is done being punished for now and she needs to take her plug out to supervise you in how to properly punish mommy’s baby girl!

“No, Todd. Mommy wasn’t telling you what mommy’s asshole needs. Mommy was just…

“No! Mommy is not trying to get out of her punishment. Mommy just thought…

“Please, Todd. Please don’t tell daddy that mommy was being difficult! Mommy was only…

“Yes. Mommy thinks that wearing the next size up punishment dildo is a proper reprimand for mommy not remembering her place.

“Yes, Todd. Mommy agrees that it’s not mommy’s position to give orders when she has a punishment plug in her back hole and cum dripping out of her front hole.

“My, my, Todd! You’re very strict! You’ll make some lucky woman an amazing husband someday. Hopefully, mommy’s little girl will continue to make you happy and it will be her. Mommy would hate to miss out on being punished by you again!

“Amanda, can you fetch the next size plug for mommy? And some more lube? The new plug won’t go in mommy very easily…


Of course, despite the compromise of Laura letting Amanda and Todd force the terribly large punishment dildo up her tortured butt hole, Todd had told Dave that she’d been difficult during the punishment anyway. Since he wasn’t actually lying, Laura had nothing to say to her angry husband in her own defense. But seeing as the dildo that was now ravaging Laura’s rectal track was the equal of any she had ever had up her ass previously, Dave thought that she had learned her lesson well enough and so only punish fucked her for another half hour that night with that very same toy. Further, Laura’s over stretched nether hole was not finally unlocked from the massive spiked dong until the next morning.

Laura had had to call in sick that day as she couldn’t stand up properly. Thankfully, Laura’s boss, Beverly, knew exactly what ‘Rectal Fever’ was from her own personal experience and Laura was told to take as long as she needed to recover. Actually, that specific reason was a checkbox on PTO request forms at nearly all companies these days, as it’s one of the most common reasons for missed work for female employees. Whoever said bureaucracy wasn’t adaptable?

As would be expected, that horrendous phallus had then become Laura’s official maximum capacity as far as Dave was concerned. So she spent the next night with it firmly locked up her tortured backside.

And the next.

And the next.

Laura did eventually get used to it; she always did. Although it was quite a while before Laura’s maximum capacity plug was increased yet again.

And again.

And again.

This was the way of things in today’s modern society. Laura had happily spent almost her entire adult life with Dave that way, just as Amanda was equally happy with her ever-expanding maximum capacity as a result of Todd’s loving care of her anal wellbeing. Every properly raised woman should be so lucky. Thankfully, most were.

That night’s training session had been one of the greatest evenings in Amanda’s young life. She and Todd still liked to watch the video of that night when they had a quiet evening at home together, laying oppositely on their own king sized mattress in their equally spacious master bedroom; Amanda playfully allowing Todd’s dick to tickle the depths of her throat while Todd lazily worked his forearm in and out of Amanda’s accommodating nether hole.

And the lessons Todd had learned that night had been put to excellent use over the years. He normally found a good excuse for conducting long punishment sessions on his loving wife at least two or three times a month. And every time Amanda felt those horrible punishment plugs violate her bottom yet again, she always thought of her mother and that special night. After all, Todd and Amanda’s own extra large sets of heavy grit punishment plugs had been a wedding present from Dave and Laura.

Her parents had actually gifted the monogrammed set to Amanda and Todd the night before the wedding, during Amanda’s final training session as an unmarried daughter; incidentally, that night is also among her favorite memories, but that’s a story for another time. The next day, Laura – being the hopeless romantic that she was – had insisted that Amanda wear one of the larger ones under her wedding dress throughout the ceremony. Of course, what started as simply ‘throughout the ceremony’ ended up lasting through the reception as well. Towards the end of the night, Amanda had tried her hardest to stay off her feet as much as she could since her rubbed raw rectal membranes caused considerable pain to simply stand; let alone to walk or dance. She’d tried to blame her condition on too much champagne, but she was pretty sure her mother saw through her clever ruse. Laura insisted that a happy bride should never be a stick-in-the-mud at her own wedding and sent bride’s maid after bride’s maid to keep Amanda on the dance floor well into the night. It was only later that Amanda found out that all her bride’s maids had had matching punishment dildos locked on under their dresses as an unofficial wedding party dress code. She should have expected as much though. Most of her bride’s maids were her sisters and cousins, after all.

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