A Proper Young Woman's Guide to Anal Etiquette Ch. 03

Emily continued to moan in pleasure from today's episode of forceful cunt lapping; not that she minded it in the slightest, as she regularly endured this from her older sister. Her moaning was only occasionally broken by a soft squeak or a slight intake of breath as the randomly moving plug found a new and interesting way to stretch the pliable ring of muscle between her parted ass cheeks. She soon felt her combined anal and vaginal orgasm approaching quickly, and its approach heralded the disappearance of any possibility she had of summoning the internal fortitude to stop her sister from doing anything she wanted to her willing, hormone filled body. With a final moan of acceptance of her sealed fate, Emily gave up what little resistance she had left and awaited the coming of the waves of orgasm that were already tickling the tips of her toes high above her head.

Cora felt the tightening of Emily's pussy around her tongue as it sought out the depths of her sister's delicious hole, and knew what was coming. Not slowing down in her manipulations to her sister's squishy cunt and now sloppy ass, Cora expertly pushed her sister right up to the edge of orgasm, and then smiled to herself as she deliberately pushed her younger sibling right off the edge into screaming, convulsing oblivion. Getting another woman to orgasm hard enough to the point of almost blacking out was something any good sister -- or mother, or aunt, or daughter, etc. -- should know how to do. And Cora was an established expert at pushing Emily's buttons.

Riding her sister's jerking cunt while maintaining orgasm inducing suction was a difficult task. Even though Cora had long since mastered the task of riding out Emily's convulsions, it still took all her concentration to achieve it. So much so that she had to stop the twisting and turning of the butt plug in order to do so. She simply buried the thick latex monster up to the hilt in her younger sister's ass and grabbed onto the base to gain an extra hand hold on Emily's spasming hips. Cora's effort was not without reward as Emily's powerful orgasm lasted over a full minute before her back collapsed onto the bed. Afterwards, Emily just lay there breathing hard and whimpering softly in defeat.

Releasing her oral death grip lock with Emily's now thoroughly drenched pussy, Cora stood up licking the residual wetness from her lips. "God! I can't believe how good she tastes!" she proclaimed to herself. Pushing the blue jean-encased ankles of Emily's legs farther forward and down, Cora let go and was amused to note that Emily just held them in that position as she tried to recover from her mind blowing orgasm.

It was a recovery that both sisters knew full well would never take place.

Reaching under Emily's bed, Cora retrieved the younger woman's masturbation kit. Upon sliding out the heavy container and opening it up, she retrieved her favorite dildo harness and wrapped it around her slender waits and snapped it on over the cheerleader skirt she still wore. As expected, the harness was already adjusted perfectly to her hips; after all, Cora used the dildo harness from Emily's kit more often than anyone else did.

She knew that Emily was currently dilated enough for a three and a half inch wide toy by virtue of the one that had already spent the entire day stretching the unwilling nether hole. Feeling particularly horny herself, she was in no mood to waste time stretching her sister out to accommodate a still larger plug up her already sore bottom. Coming to this decision quickly, she selected a fourteen inch long, three and a half inch wide, realistically veined dildo and snapped its magnetic locks onto the front of the dildo harness.

Standing up, she paused to admire herself in the room's full length mirror. She would have been an image straight out of a futanari manga: a hot cheerleader with a massive ebony cock protruding from her miniskirt adorned hips. She stroked her faux-cock a few times and made wet kissing motions towards the mirror for added effect, before returning her attention to her still compliant younger sister.

Moving back over to the bed with her reclining, panting sister, she noticed her own -- now licked clean and discarded -- bottom trainer lying on the bed next to the exhausted looking young woman. Without a second thought, she bent down to retrieve it. Reaching back behind her she unsnapped the rear strap of the dildo harness and, lining the cleaned plug up with her still gaping rear hole, began to push the four and a quarter inch thick butt stretcher back up her abused rectum. She winced sharply as the dry latex grabbed at her sore ass tissue as it forced its way further into the depths of her perpetually yearning-to-be-filled back hole. Cora eventually had to squat slightly and reach around with both hands to force the plug fully up her tender asshole. She sighed softly as she felt her sphincter wrap itself around the comforting mass of the four inch thick neck of her butt plug once again. Re-snapping the leather strap and securing the harness once more around her waist, Cora thought to herself how much it was going to hurt to pull that unlubed plug back out of her bottom again. It was an eventuality she found that she was actually looking forward to.

Positioning herself between the widely spread cheeks of her sister's backside, Cora reached down to remove the fully seated plug up Emily's poor dilapidated asshole. What little resistance there was at the first extraction was gone as the plug slid quickly out of Emily's ass with the familiar wet slurping sound.

"Here you go, sis," Cora said as she passed the stained plug down to her sister. "This one needs cleaning too."

Emily took the plug which had spent the day up her own ass without question or complaint and began working her tongue down its length; cleaning off both the residual lube and her own stains along the way. Cora smiled to herself as she watched the submissive actions of her younger sister. "All it took to transform Emily into a totally submissive fuck slut was one good orgasm," she commented silently to herself. "Of course, the rest of us Wilder women are that way naturally, so I guess she has more self restraint than the rest of us combined."

The yawning chasm between Emily's spread cheeks was now visible again. Cora reached down with her right hand and sank it up to the thumb into Emily's soaked and well lubricated cunt. Rotating it around in the sloshing wetness for a few seconds, she extracted her hand and wiped the homemade girl lube down the length of her fourteen inch bitch tamer. Repeating the process several more times, it wasn't long before the latex horror was glistening with Emily's pussy juices. As Cora knelt down and lined the massive head of the faux-cock up with her sister's slippery back orifice, her mind drifted back to her own first lesson in using pussy juice as lubricant that she'd received from her mother.

***

"Now, Cora, let's move on to how a woman gives another woman a proper anal buggering with a strap-on. A girl's own juices make the perfect lubricant for this for many reasons. First of all because it's very slick; notice how wet you are after mommy brought you to a few orgasms with her tongue and mouth when she focused on your hot little cunt? Let's see if we can't get some of that cum out of you for a useful purpose. [...] See? Mommy's whole fist slipped right up to the wrist in your front hole and you barely even cried out in pain! Ah, the wonders of how relaxed a few strong orgasms can make a woman!

"After mommy rotates her fist around that tasty slit of yours a few times to make sure that it's fully coated in your juices, mommy can pull it out and wipe it all over her nice, big strap-on. Now quit complaining, young lady! I realize it's a little bigger than the dildo mommy was using on you earlier but it will fit. Mothers just know these things.

"Now I just need to get some more of your juices [...] there we go. It went in a lot easier that time. You barely jumped at all! We just need to make sure we have enough pussy juice, and wipe it all over mommy's strap-on again. One more time should do it. [...] I think you're starting to like mommy's fist up that horny young cunt of yours, aren't you. Well, that not something you should get used to. Pussy fisting should only be for very special occasions. A woman's pussy needs to be nice and tight to milk men's penises when they fuck us. You naughty girl! You really are enjoying this too much. Mommy will have to punish you after tonight's lesson.

"But that's for later. Now, reach back and spread your cheeks so mommy can line up her strap-on with your loose asshole. [...] See how easy that slipped in? I know mommy's big dick hurts now, baby, but it will feel really good in a few minutes; although mommy doesn't want to upset her baby too much so I'll push the other half in a little more slowly. [...] There! That wasn't so bad. Now you have the whole toy buried to the hilt up your bottom.

"Now pay attention to the sensations coming from your stretched back hole as mommy pulls her toy almost all the way out. Feel it slip past your rectal walls and pull your sphincter outwards slightly? It's not causing you much discomfort now since all that slippery pussy juice mommy slathered onto the dildo is still nice and wet. So just lay back and enjoy the nice deep rectal plowing mommy knows her daughters like. [...]

"Cora. I know you're getting close to your second anal orgasm, but pay attention to mommy for a minute. Now, mommy's big strap-on has been pounding away at your little asshole at a steady pace for over ten minutes now and you might notice that it's starting to become a little uncomfortable. This is because pussy juice is water based and is being absorbed by the walls of this greedy ass of yours. It's also evaporating offmommy's toy when it's outside of your body.

"If you pay attention to the sensations in your ass again as mommy fucks you with her big fake dick, you'll notice that the big dildo is no longer slipping effortlessly past your rectal walls and what was once a slight tug on your sphincter is now a firm pulling. Mommy can actually watch it dragging your sphincter back and forth a few inches into and away from your body. This sensation will only get worse over the next few minutes as the last of your pussy juice is worn away. What's left is really just sweat, waste and what little girl cum is left to lubricate the extended fucking mommy is going to give her daughter's needy bottom. This is really a great way to get that extra stretch out of a woman's ass! [...]

"Good girl! That was your most powerful orgasm yet! And we've only been at this for barely fifteen minutes! If you'll pay a little extra attention to your asshole, you'll feel it's totally devoid of lubricant down there now. This is what we want. Yes it is a little harder for mommy to driver her thick toy that deeply into your bottom, but mommy works out so she can keep up this pace for quite a while yet. But for tonight, we'll just go another fifteen minutes or so. Nonsense! This won't kill you. In fact, I think you'll have quite a few more powerful orgasms before I pull out. Daddy used to do this to mommy every night, with much larger toys than what's up your bottom now, just so mommy would have a good night's sleep. Daddy took such good care of mommy's dirty ass! [...]

Good girl! We're almost done! Just a few more minutes and my darling daughter should be howling in another deep anal orgasm. Now stop crying and just enjoy this. If you're a good girl and cum really hard for mommy one last time, mommy will let you pick out any one of her toys that you want and you can practice this technique on mommy's ass for the rest of tonight's lesson.

"Well, mommy really didn't mean you could use one of her punishment dildos, but I guess mommy forgot to specify; although, a nice thick punishment dildo would feel really good up mommy's hungry ass. It should also make sure Mommy sleeps really well tonight!"

***

Cora smiled to herself at the fond memory. She'd actually selected one of her mother's largest punishment plugs and had sawed it in and out of the crying matriarch's sore and orgasming asshole for almost a full hour and a half before the older woman passed out from sheer exhaustion, and a sustained and continuous anal orgasm that had lasted nearly forty minutes. Cora, ever the good and loyal daughter, had retrieved one of her mother's dildo straps and secured the punishment plug deep in her mother's bowels to make sure that it wouldn't slip out during the night. She'd then covered her snoring mother up to sleep it off.

Laura had slept until late the next afternoon and had woken up in a very good mood indeed. Such a good mood in fact, that she never did punish Cora for enjoying the pussy fisting too much. She did always believe in treating her daughters fairly and evenly.

"Please," Emily moaned, snapping Cora back to the present from her reminiscing. "Please use some real lube on it this time, Cora," Emily pleaded as the head of the wide faux-dick slipped past her stretched out anus.

"Every day after school you ask me the same thing and every day I give you the same answer," Cora replied. "'If I start going easy on you today, you'll just expect it tomorrow,'" Cora quoted for the umpteenth time as she pushed another few inches of the thick anal pacifier into her sister's unresisting backside.

"Yes, but I'm really sore back there today," Emily argued as she grunted in discomfort at the pulling sensation along her rectum as the latex prick slid home another few inches. "And I don't usually get ass fucked with something this large!"

"Well, I'm really horny today," Cora replied firmly, allowing yet another few inches of veined dildo to slide into her complaining sibling. "And it's nothing bigger than what you've already had up your ass today. So, if you think about it, I'm actually being pretty gentle with you. I could have picked out an even larger fake cock for your hungry ass to swallow. Actually, if you really want me to use your bottom the way it ought to be used, I probably should." Cora stopped the latex torpedo's forward progress and started to pull back out a fraction of an inch.

"No!" Emily cried reaching back with her hands to stop Cora's retreating hips; the half clean plug she'd been sucking on fell from her lips and onto her chest and finally came to a rest between her boobs, which were still covered by her yellow t-shirt. "This one's fine." Then after a moment, "And thank you for being so gentle with me. I really appreciate it." Emily continued earnestly.

"It's no problem, baby sis," Cora replied as she resumed her inward momentum. "After all, I'm really doing this all for you, ya know," she lied. "Now why don't you reach back and spread those boney butt cheeks of yours so I can really get a good rhythm going when I start fucking that tiny asshole of yours," she commanded.

Emily complied instantly; her mind too full of endorphins to do anything else, really.

The last few inches of insertion were the most fun; for Cora at least. She could clearly see the progress of the thick latex dick as it made its way though Emily's rectal track. Since Emily's shirt had been pushed up to just under her breasts during the thrashing orgasm, and the outline of the imposing toy was clearly visible on the reclining woman's toned abdomen.

Finally, the base of the latex slab came to rest between Emily's firm butt cheeks; signifying a full fourteen inches of thick cock buried up the small teenager's passively accepting nether hole. Cora reached forward and grabbed a hold of the denim restrained ankles of her younger sister and, bending down slightly, brought them over her head and secured the ankles and almost-off blue jeans around her neck. Emily's legs now safely held in position, Cora stood up; the motion bringing Emily's hips clear off the bed with her. The geometry of the action pulled their hips momentarily away from each other a few inches before Emily's shoulders slid down the bed and her butthole again fully seated itself on the slick fourteen inch dilator buried in that most private of holes. Emily let out a soft groan at the firm packing of her asshole; her hips involuntarily making small circular motions in the air.

Cora was fascinated at how this angle let her observe the clear outline of the thick dildo pushing up under her sister's muscular midsection. "Oh," Cora thought to herself. "We're doing it this way more often from now on. This is just way too cool!" This position also allowed her to grab hold of Emily's hips with both hands for extra leverage. With Emily's butt floating about a foot off the bed and most of her weight on her shoulders, the angle was perfect for some truly deep anal buggery -- as their mother liked to call strap-on ass fucking. She adjusted her stance to make sure she had a good footing and prepared herself for the exertion to come.

What would eventually become a no-holds-barred backdoor plowing started out slow enough. Cora backed her hips up until the fourteen inch ass reamer came about halfway out of its home before sinking it all the way back in. Emily's butt met Cora's thighs for a split second before they bounced off each other; establishing the initial rhythm.

Emily cried out in mixed pain and pleasure as the first stoke was completed and the second began. She tightened her grip on her spread butt cheeks; ensuring -- despite her mental opposition to what was about to happen -- that her sister had clear and unfettered access to her rear fuck port. Again her butt bounced off of Cora's strong thighs and the third stoke was already underway. By the sixth time her bottom bounced off her sister, all Emily could do was moan in pleasure at the warmth emanating from deep in her bowels.

The relative gentleness of the initial strokes were slowly replaced by something far more primal as Cora extracted more and more of the thick bitch-tamer with each thrust; the thrusts themselves becoming more and more rapid as the minutes wore on. Cora began to pant from the exertion and Emily was now openly wailing at the sustained anal assault of the merciless fourteen inch monster. They soon settled into a fast and furious butt pounding rhythm that involved about twelve inches of latex being extracted on each quick and powerful thrust of Cora's hips. Emily's butt cheeks rippled again and again at the continuous impacts they had with her sister's thighs. Enough sweat and pussy juice combined at the point of skin contact that each time the thick latex tool bottomed out in Emily's quivering bottom, sharp fleshy slapping sounds began accenting the end of yet another deep gut wrenching thrust.

No sooner had they established a steady cadence that Emily had her first powerful anal orgasm. All thoughts of ensuring her sister had an unrestricted path right up her over tenderized asshole thrown aside, Emily let go of her bouncing ass cheeks to rip her t-shirt and bra away from her bouncing perky 32B tits. Once freed, her thumbs and forefingers closed in on her hard pink nipples; crushing and rolling them firmly. Of all the Wilder daughters, it was well know that Emily had inherited their mother's true love of rough nipple play during any kind of sex, and anal sex especially -- even more so than their masochist-to-the-extreme sister, Naomi. With the added pain now pulsing from her aching nipples, Emily's powerful orgasm hit a new peak.

Cora rode out her sister's first orgasm without modifying the punishing rhythm they'd already established. Throughout Emily's hard minute long orgasm Cora kept the three and a half inch thick, fourteen inch long, latex dildo slamming into her sister's red and abused butt hole with firm determined strokes.

Finally, the orgasm died down, leaving Emily panting and crying softly. "Please, Cora," she moaned. "I don't think my ass can take much more of this today. Can't we stop a little early today?" she pleaded.