A Proper Young Woman's Guide to Anal Etiquette Ch. 07


"And here I thought you actually just wanted to sleep," Emily managed to get out in between their tongue play and the cruel treatment her nipples were enduring.

"Wrong again, little sister!" Cora corrected lustfully before shutting Emily up with even more powerful spit swapping. Emily's will dissolved submissively from her dominant sister's advances.

After a few minutes of this loving abuse, the younger sister began to spread her legs open to give her fingers access to the dripping cunt between her slender legs. This was the opening Cora was looking for in her cunningly devised ambush. Relaxing her own legs, the three and a quarter inch wide, twenty-two inch long strap-on fixed to her waist sprang free and flung itself upwards to collide with an audible 'whack' against Emily's drenched pussy.

Emily's eyes shot open at the unexpected impact and looked at her sister questioningly. To her credit, she neither paused in her passionate kissing nor pulled away from what was clearly a sizable phallus strapped to her sister's pelvis; knowing full well its intended target. Emily's eyes slowly closed again, in acceptance to her fate, as Cora moved her hips back and forth; causing the thick tool to massage her sister's engorged vaginal lips.

"Could you give me a hand here, Em? My hands are kind of out of the way to help us much," Cora asked her sister softly before returning to their kissing.

Without verbally responding or opening her eyes, Emily reached in between their bodies with her free hand and leaned forward. Finding the pre-lubricated shaft with her hand, she skillfully lined the brutally thick - for her tight and untrained ass at least - dildo up with her loosened sphincter and helped Cora guide the first few inches inside her needy rectum. Only a few slight gasps escaped Emily's lips as Cora fed more and more latex up her nether hole.

With only about eight inches in total buried up her sister, Cora began a gentle back and forth fucking motion. She intended this to be a soft and extended lovemaking, not a brutal fucking like their normal sisterly activities seemed to revolve around. Of course, Emily had no idea of the true length of the twenty-two inch rectal rooter that she was soon to be fully impaled upon. To Cora's knowledge, the young waif had never peen penetrated that deeply before. She wondered how many inches she could fit into her younger and less experienced sister before Emily figured out that something special was happening.

If she was a betting woman, she'd wager about fourteen inches.

With the initial penetration accomplished, Emily reached her hand back to rest on her sister's hips. She pulled forward gently to encourage Cora to fuck her ass deeper. If only she knew how deep Cora's strap-on could force itself into her guts, she might not have been as eager.

Trying to avoid tipping off Emily to her true plight, Cora continued her gentle rhythm; allowing her tool to penetrate a little deeper into her oblivious sister with each inward thrust. Emily only moaned with desire as the violation of her tight hole became deeper and deeper. Throughout it all, Cora kept her little sister distracted with their energetic spit swapping and the cruel manipulation of the younger woman's now very sore tits.

After nearly five minutes of gentle butt reaming, Cora estimated that she was about twelve inches deep into her sister's most private orifice. Emily was out of her mind with masochistic desire. Over and over again she would beg her older sister to ram the huge butt splitter into her pert ass hard, fast, and without regard to her comfort or likely pleas for mercy; and over and over again Cora would refuse. It was a pace that Emily was unfamiliar with. Their parents and older sisters were fond of much more rigorous sex - especially where anal sex was concerned - and they had trained their daughters and younger sisters to both love and crave a vigorous rectal pounding; the more forceful the better. Because of this, Emily had yet to reach a single mind-blowing orgasm; and after five minutes of intercourse without one was something Wilder women were just not accustomed to. Cora could admit to herself that if the roles were reversed, she too would be going out of her mind in frustration.

"Please, Cora!... Quit... teasing me!" Emily demanded in between Cora's slow, yet deep and deeper, thrusts into her bottom hole. "I need... to cum... so bad!"

"Shhh, now baby sister," soothed Cora at the other woman's growing frustration. "Just let your big sister work out that tiny little bottom of yours. If you'd quit whining constantly about needing to cum so bad and just enjoy the nice fucking your big sister is giving you, you might actually come to like this," Cora lied. No Wilder woman alive today would willingly submit to such a slow and drawn out butt loving if they had the choice between that and a fast and furious anal pounding that could last the same amount of time. The latter was infinitely more productive in the creation of pleasure producing hormones.

"But... Coraaaaaaaa!" cried Emily. "I need... to cum... so fucking... baaaaaaad!"

"No buts!" Cora shot back. "You'll take your nice butt fucking like a big girl and you'll like it! Is that understood?" she said as she forced at least another inch of lengthy bottom plunging toy up her sister's horny backside. She pulled at Emily's raw nipple extra hard so that her sister wouldn't notice the deeper penetration which by now had to have been well past fourteen inches. Emily only groaned animalistically and arched her back to give her sadistic sister even more access to her poor tits; this had the added effect of also forcing another inch or so of thick latex up her back hole. In Emily's lust-filled mindlessness, she didn't even seem to notice.

It's a good thing I didn't bet any real money on the fourteen inch mark, Cora remarked to herself. I think I'd have just lost my investment!

Finally, after only three or so more thrusts, Emily started to notice something was up. Grunting in unanticipated discomfort as Cora's strap-on violated reaches of her colon that had never before known the taste of latex, Emily's eyes shot open to stare at her sister questioningly.

"God, damn!... How long... is that thing... Cora?" she asked seriously.

"Oh, only about twenty-two inches or so," Cora commented dismissively. "I borrowed it from mother's full length set earlier this evening. I figured you'd appreciate it!"

"Twenty-two inches! Are you nuts!" Emily demanded as she actually got a full sentence out in a single breath. "I can't take anything that deep!"

"Of course you can, you silly goose!" Cora said reassuringly. "You've already taken three quarters of it," she added as she thrust her hips forward more firmly than she had previously to split her sister's lovely butt by almost two full additional inches of the three and a quarter inch thick latex column. Emily cried out softly in pain and clamped her eyes tightly closed.

Knowing that the cat was out of the bag now, Cora began to pick up the pace slightly and press forward more deeply with each slow and purposeful thrust. She knew from firsthand experience how uncomfortable the first few times were with truly deep anal penetration. Their mother had introduced her to the act only a few months ago as part of their more and more frequent training sessions.

Cora had cried and begged her mother to stop as Laura had plunged the twenty-two inch long, three and three quarter inch wide dildo deeper and deeper into her sore and protesting bottom. Had it not been for Naomi's energetic cunnilingus - Laura had asked her middle daughter to assist in Cora's training that night - distracting her while their mother violated her deeper than she thought possible, she might actually have tried to get away. As it was, once Laura had bottomed the thick and incredibly long dong up her spasming butthole and started a truly grueling ram-fucking with her chosen tool, Cora found out how pleasurable truly deep anal violation could be. She's cum so hard and so long that night that Cora herself had requested her mother fuck her deeply during their next three training sessions. Laura had happily complied with her daughters requests for a time before finally denying them as she had more to teach the young girl than deep fucking with a mere three and three quarter inch dildo.

So Cora knew how much Emily would appreciate what she was doing for her younger sister; as long as she could keep her distracted long enough to complete the soul-deep desecration of the younger woman's aching bottom. After a dozen more slow thrusts, Cora knew she only had a few inches to go before she was completely bottomed out in her sibling's butt.

"Fuuuuuck!... Coraaaaaa!" panted Emily. "Stop! I can't... take anymore!"

"Sure you can!" Cora responded quickly, not slowing her pace. "You only have an inch left to go!"

Well, it was more like two, but who was counting, Cora corrected herself.

"Nooooo... No more..."

"Come now! Wasn't it you who demanded that I fuck you despite any protests you might utter?" Cora reminded. "It couldn't have been more than a few minutes ago. Surely, you haven't forgotten your request already?"

"Not... what I... meant!" Emily grunted as the thick and realistically veined dildo started to ram into the bottom of her lungs on its never ending quest to get to the deepest point inside Emily's resisting body. "Please... stop..."

"Nonsense! You're almost there," Cora said reassuringly. "Trust me. Once you get this all the way in you have a few solid cums, you'll be begging for this every night!"

"Fuck you, Cora! Take it out!" Emily said vehemently, but made no move to try and escape the painfully deep violation of her tight backside.

Undeterred by her sister's anger, Cora continued to force more and more of the thick shaft deeper and deeper into her now crying sister. She had cried too when their mother had penetrated her this deeply for the first time.

"Trust me," Cora repeated. "I know it hurts the first time. Mommy only fucked me this deeply a few months ago and it hurt like Hell!" she confided in her agonized sister. "Just remember how much it hurt when mommy started stretching you back there in the first place, and now you're a certified anal masochist; just like the rest of us. And I know you've seen mother and Amanda take things deeper than this up their butts, so you know it's possible. So will you let your big sister make you feel good?"

Emily bit her lower lip and breathed in and out brokenly a few times before answering, "Yes," very softly.

Cora knew Emily's last defenses had finally fallen. "Good," she said and smiled down into the tear filled eyes of her favorite sister.

With one final thrust of her hips, Cora buried all twenty-two inches of three and a quarter inch thick bitch tamer up the protesting backside of the youngest Wilder. Emily only groaned pitifully and the extreme violation of her shapely backside.

"Good, girl!" Cora announced happily. "All twenty-two inches!"

Emily only moaned brokenly.

With her hips now flush with her sister's muscular butt cheeks, Cora asked, "Are you ready for your big sister to make all this suffering worthwhile?"

Emily only nodded her head sharply and kept her tear filled eyes tightly closed as she dealt with the intense feelings of the organ-rearranging penetration of her rectal tract.

Cora pulled her hips back about six inches or so before slamming the long faux-dick right back up to the hilt in her sister's bottom. Emily cried out in pain at the unexpected thrust.

Not letting Emily recover from that first epic, tooth-rattling plunge, Cora immediately pulled out and pushed back in again. And again. And again! All Emily could do was cry out silently in agony at the immense violation.

After a dozen or so thrusts, Cora could tell that the motion took noticeably less effort on her part as Emily's colon accommodated to this new and exciting way of anal intercourse. Emily's mouth still hung open silently as Cora continued the obscene desecration of her pert backside.

Finally, Emily made a sound. Not a cry of anguish or a scream of pain, but a long, low groan of masochistic pleasure. Cora smiled to herself as a small part in the back of her brain paraphrased a line from a classic movie: Your journey to the Dark Side is now complete, young Wilder!

Pausing momentarily in her rough fucking of her sister's now squirming butt, Cora slowly rolled Emily onto her front as she simultaneously lifted herself up onto her hands over her sister's back. Using her superior position, she spread Emily's legs with her knees to open the eighteen year-old's rearmost hole as wide as it could go and to align herself with the optimum angle to gain access to that orifice's deepest recesses.

Pulling back a full foot, Cora paused only momentarily to look down and enjoy the sight of her thick tool splitting two toned butt cheeks before slamming all twenty-two inches of thick ass breaking latex back into her beautiful, redheaded sister. Emily only groaned with unabashed lust at the violent shove as her sister bottomed out once again. From that point onwards, the pace and viciousness of the ass fucking was what any self-respecting Wilder woman would appreciate.

Emily had asked Cora to fuck her ass hard, fast, and without regard to her comfort or pleas for mercy. How could Cora refuse a request like that?

She didn't.

And as the pounding continued, and Emily was reduced to an orgasmed-out wreck, her only response to her older sister's frenzied pounding was to arch her butt to give Cora a better angle and to reach back with both hands to spread her cheeks to give her easier access.

Welcome to the Dark Side, Emily, Cora thought.

Welcome to the Dark Side...

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