A Proper Young Woman's Guide to Anal Etiquette

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 myself via the CONTACT form in my profile.. If I can't stop you I can at least make sure you're doing it right. Consider yourself disclaimed.

Wilder Nights

As Amanda walked down the hall towards Naomi's room, she briefly paused at the doorway to her two kid sisters' room. Just as her mother had observed half an hour ago, Cora was still jackhammering her sizable toy into the exhausted ass of an obviously orgasmed-out Emily. The poor girl simply lay where she was - not that she was going to go anywhere, restrained wrist and ankle to the bed like she was - and took the vicious pounding to her nether hole with exhausted-sounding grunts and moans. Despite the vacant look in her red and puffy eyes, it was obvious to Amanda that Emily was still very much enjoying all the loving attention she was getting from her sister.

We'll get that tight little ass of hers nice and opened up before not too much longer, Amanda thought to herself, as she watched the continuing anal violation of her eighteen-year-old sister. After all, there're a lot of horny women in this house who'd love nothing better than to break in a brand new hole! Amanda smiled slyly and made a mental note to arrange for some sisterly bonding time in the next few days for Emily and herself. She and the young woman had a lot of catching up to do; not that she intended anything like talking to be involved in their bonding!

Despite wanting to stay and watch the wickedly hot scene play itself out, Amanda hurried off to Naomi's room to check in on her.

Upon entering the room - without knocking, and uninvited - Amanda crossed to her sister's bed and flopped herself down. "So. How're you doing, sis?"

"I'm late, that's how I'm doing," Naomi responded as she finished getting dressed for work at Gapers: 'Fine European Dining at an Affordable Price'. Unlike a certain restaurant chain from earlier in the century named after the call of an owl, Gapers didn't try to pass itself off as a family restaurant. In actuality, it was what strip clubs from the previous century had developed into when they'd had to evolve along with an ever-changing society. Topless women pole dancing had long since become passé. After all, you could see more flesh at most public beaches since America had adopted Europe's more liberal attitude toward bare-breasted women in public. The new risqué was women publicly displaying their distended anuses to a paying audience. While Naomi wasn't a performer herself - Laura would have kicked her out of the house if she'd ever found out - she was 'merely' a waitress (although the waitress uniforms at Gapers left very little to the imagination). Laura still didn't approve one bit, but at least she allowed Naomi to continue to live under her roof despite her distasteful job.

Her work schedule was erratic, but this week's work hours had been more sporadic than usual and Naomi was none too happy about it. She had to be at work early tonight and she'd be leaving pretty soon; Naomi would be home in the early morning hours, after she helped close the restaurant. Of course, she should have been gone twenty minutes ago, but Amanda's help in ensuring Naomi was properly cleaned out had delayed her by almost half an hour.

"Mother hates me wearing these things out in public," Naomi commented as she pulled on one of her many pairs of black satin French cut gape panties, "which I think is just a bit hypocritical of her since I've seen her wear them on quite a few occasions when Dad was around," she added rebelliously.

At first glance, gape panties, or gapers, looked like normal crotch-less panties worn by most women on a daily basis - if panties were worn at all that was - before the differences became apparent. While most panties had a string in the back to ride over the base of a plug that was inevitably packed into the nether hole, the back of gapers instead came together in six adjustable straps ending in smooth metal hooks. Two straps went between the legs on either side of the pussy mound, two passed around the back of the legs where the ass cheek met the top of the thigh, and two came over the butt from above. The hooks were then inserted into the anus and pulled firmly apart until a wide fleshy pink cavern could be seen between two heart shaped ass cheeks. The more shapely the ass, the better the gape's effect; and it went without saying that all the Wilder women - regardless of their shape - had amazing asses!

Naomi had purchased these particular gapers from an online retailer in Berlin; and they came equipped with some extra features that were hard to find over here in the New World. While most traditional gape and crotch-less panties were designed to fully display the entire genital region, Naomi's pair only displayed the bottom two thirds of her cleanly shaven pussy lips. This allowed a standard or dilation catheter to be inserted into the urethra and become locked in place as the rest of the undergarment was secured around it. A small hole was conveniently designed into the front of the panties for the drainage port of the catheter to slip through.

Naomi held the panties in place with the tube extending from the base of the dilation catheter poking through the small hole. She'd already inserted the catheter and expanded up her pisshole before Amanda came in.

"True, but most women wear them with little black dresses or something," Amanda countered, "for occasions where corsets may be inappropriate and the abdominal bulge of a normal dilator plug would be... embarrassing. And what size is that thing anyway?"

"Oh, this?" Naomi asked motioning to her plastic piss plug. "It's only five eight's inches thick; I'm still working on wearing larger ones for extended periods of time. I'm really glad Nana gave us these things; they're great!" she said enthusiastically.

"Why am I not surprised you'd love them?" Amanda said shaking her head. "Anyway, your uniform skirt barely passes for a thick belt, that could be one of the reasons mother doesn't approve," she added holding up Naomi's deep red micro-mini skirt. When properly secured around Naomi's waist, the garment barely covered the top half of her firm bottom; leaving her wet pussy in front and gaping hole in back plainly visible to anyone who cared to look, and there would be a lot of people wanting to look when she got to work. After all, the girls with the biggest gapes invariably got the best tips. Naomi prided herself on being one of Gaper's top earners; for non-performers at least. If her mother would allow her to go up on stage she could probably double or triple her weekly pay check.

"Semantics!" Naomi insisted as she inserted one hook after another and tugged at the reinforced satin straps. "I'm not wearing anything at the restaurant that you wouldn't see walking down any street in Paris or Milan. It's not my fault that America is twenty years behind Europe in social development!" Naomi turned to look at her backside in the full length mirror and adjusted the straps to get her gape as round as it could; oblong or egg shaped gapes just looked odd, after all. The last few adjustments elicited grunts from the twenty-two year old brunette as the diameter of the growing darkness between her cheeks expanded again and again with each firm pull. "There. Perfect," she declared and reached for the garter belt laying on her bed to go over her purpose built lingerie.

"Really? Perfect you say? Honey, who the hell taught you how to properly fit gape panties?" Amanda inquired. "Certainly not our loving mother. She's the one who taught me and Mary when we were younger and that's not how you do it at all."

Naomi looked slightly hurt at her older sister's comment, "What do you mean? You put the hooks up your ass and shorten the straps until they're uncomfortable. How many different ways can there be to shorten straps?" she asked slightly annoyed as she placed her hands on her hips and shifted her weight to her left leg in the unimpressed-stubborn-little-girl gesture that she'd never grown out of. The gape panties were all Naomi had had a chance to slip into yet and her medium sized free breasts swayed back and forth with the jerkiness of her movements.

Amanda allowed her eyes to track the motion of the incredibly perky twenty-two year old tits in front of her before she answered. "Quit being such a prissy little bitch and come over here and I'll show you," she commanded as she half turned to fetch Naomi's nighttime dildo that rested conveniently on the night table next to her bed; exactly where Naomi had left it when she'd woken up and taken it out and tongue washed it clean before heading to the showers. "That is if you want to learn the right way. It may help your tip total," she added helpfully.

The thought of better tips took the edge off of Naomi's annoyance and she walked over to stand next to her big sister. "I'm listening," she said as her sister hefted the thick toy. The shaft was four inches wide and eleven inches long. It was the very same veined toy she's used to masturbate herself with yesterday morning after she'd abused her mother while the older woman had been preoccupied. It wasn't as big as Naomi could take, but it left her rectal cavity comfortably full all night. And what more could a masochist ask for?

To be uncomfortably full, that's what. Naomi made a mental note to shove the next size larger plug up her ass when she got home tomorrow morning. That should take the edge off.

"Good. Now turn around and bend over slightly," Amanda said and Naomi instantly complied, like the good little masochistic submissive slut-bunny that she was. Lining up the four inch bottom stretcher up with her sister's forcefully gaped anus, Amanda quickly worked the thick toy about halfway in. She smiled to herself as she listened to Naomi's pitiful grunts and groans as the younger woman's back passage was once again stretched to a full four inch diameter. Actually, it was a little larger than four inches since the hooks of the gaper panties were still fully seated around Naomi's somewhat straining anal ring.

Ah, to be young again, Amanda thought to herself. It'd been years since a meager four inch plug sliding past her own well trained sphincter had gotten a similar reaction out of her. Not that she was a stranger to the sensations she knew her sibling was experiencing - her husband Todd ensured she felt very similar sensations every day they were together. The sizes of the tools involved were just considerably larger and much longer, but the idea was the same.

"Alright, now that your hole is being held open to a consistent size, go ahead and retighten the straps. I can tell just by looking at them that they're pretty loose now," Amanda commented.

Continuing to whimper at the latex intruder forcing her tender hole wide open, Naomi did what her older sister commanded and began adjusting one strap after another. "How does that look?" she asked when she felt everything was nice and tight.

"Let me check you out," Amanda responded. "Here, hold your dildo for a minute so I can use both hands," she said. Naomi quickly took over control of her latex violator as Amanda checked the tautness of each strap. From her superior angle, Amanda managed to get every single one of them just a little bit tighter. By the time she'd finished, Naomi's intermittent whimpers had turned into soft sobs of pain at her widely stretched ring of rectal muscle. Small cracks of blackness could clearly be seen around each hook as they shared Naomi's asshole with the thick plug; a plug that was no longer doing a very good job at stretching anything.

"There you go. Now it's perfect," Amanda commented as she took the dildo away from her sister and extracted it from the widely expanded nether hole once again. As the thick phallus slid out of the pink hole with a soft wet sound, the size of the cavern stayed at the original four inch diameter. The six straps of the gape panties bit deeply into Naomi's flesh as her abused back hole attempted in vain to re-close itself. The attempt failed utterly and it maintained its near perfect circular shape.

Setting the, now unnecessary, latex tool back where she found it, Amanda returned her attention to admiring her handiwork more. Placing a hand on each of her sister's hips and holding the younger woman steady, "I think you need me to help you into these things every day before you head off to work. What do you think?" she asked as she admired Naomi's succulent bubble butt and obscenely gaping asshole.

Despite the ache emanating from her horribly stretched hole and the straps biting into her pale flesh, Naomi couldn't argue the fact that she was getting off on the pain. The chances of her having an orgasm on the way to work were very high and she hoped she didn't wreck her car when it happened. The life of a masochistic pain slut was never easy, but at least it was usually eventful. "I think you're right," was all she could say in response.

Amanda took two of her fingers and easily inserted them into Naomi's drenched pussy and pushed backwards. The fingers pushed the thin membrane of flesh that separated the two holes upwards and outwards. As she wiggled her fingers she actually managed to get her sister's rectal wall to stretch past the ring of her muscle to be outside of her body. Closing the finger loop with her thumb, Amanda massaged the thin layer of flesh firmly between her digits and listened to Naomi's groans of pleasure as her lower holes were roughly played with.

Glancing at the clock on the wall, Amanda realized that Naomi was going to be late if she allowed her sister to have an orgasm. "That's enough for now, Naomi," she said. "You need to get dressed for work or you'll be late."

"Don't care... Just a little... More..."

"Nope. That would be irresponsible of you. Now pull yourself together and finish getting dressed!"

Visibly shaking herself back to the present, Naomi pouted and moved back to the foot of the bed to finish putting her garters and stockings on. She grunted loudly as she bent over to slip the stockings onto her feet as the position yanked her already maximized hole open just a little bit more. "Can we play more when I get home from work?" she asked her older sister.

"Of course!" she answered. "It's been a while since we've had some good old fashioned sister/sister bonding. Although, it may have to wait until this weekend; I've got a big day tomorrow at the convention.

"I do have a question for you though. Do you actually like working at Gapers? I know mother hates it that you do."

"Actually, I do," Naomi answered as she hooked her stocking to the clamps on her garters. "I know it's not a proper place for a nice girl to work, and dad would not approve at all, but I enjoy it. Have you ever been to a European style club before?"

"Me? Once or twice while I was in college. Mom and dad never found out, of course. You can get away with working at Gapers being the middle child, but me, as the oldest daughter? I would have gotten my tits caned and then spent a week wearing punishment a dildo!"

They both laughed at the truth of it. Parents inevitably got less strict with each successive child. That was the way of things. The youngest kids always had the easiest time of growing up.

Amanda refrained from mentioning to her younger sister that the second time she'd gone to Gapers she'd actually been drunk enough to participate in their weekly amateur contest. They'd lined up successively larger dildos, each a full twelve inches long, from one side of the main stage to the other and opened the competition to all the girls in the audience. The winner got all the cash thrown onto the stage and free drinks for the rest of the night. The evening she'd participated there had been fourteen other tipsy 'Woo Girls' up on stage with her who'd stripped from the waist down and left their plugs at their tables. One by one they'd lowered their assholes onto one dildo after another in front of a full house of onlookers as tips rained down onto the stage. The only rule to advance was that the girls had to bounce their ass cheeks on the stage three times for the penetration to count.

After half an hour there were only two girls left: Amanda and a twenty something Asian beauty with monstrous - and obviously fake - tits named Ling. For the final showdown, all the lesser dildos they'd already passed were removed and a second set of colossal anal destroyers were secured to the stage. At the same time the pair would impale themselves and bounce their butt cheeks off the stage. If it wasn't for all the booze they'd obviously both imbibed that night, neither girl would have made it as far as she had. But in the end it was while Amanda - exhausted and resting her weight on the stage, fully impaled by a massive dildo - was waiting for Ling to bounce her tight butt cheeks off of the stage, that the Asian beauty finally called out in surrender.

The announcer then came out to proclaim the winner. Rather than let Ling extract her sore bottom from the oversized phallus, he'd simply placed both hands on her shoulders and pressed downwards firmly and impassively as he announced the impressive size to the excited crowd: Five and a quarter inches. It'd been a personal record for her at the time. Ling fought only for a moment before exhaustion took over and she allowed herself to be fully impaled on the massive dong. Amanda had tried to stand herself, only to be pushed back down, by the slightly bored announcer. Once all the patrons had finished throwing money at the stage, and most likely the owner got his sizeable cut, Amanda and Ling were allowed to extract themselves and Amanda was given a fat stack of cash $9,600 deep.

Upon returning to her table and her ecstatic girl friends, she'd been surprised to see that as a parting gift the management had helpfully attached her winning dildo to her chair. Initially, she'd been too tired and sore to play anymore, but with the taunting, chanting and general peer pressure of her girl friends she'd reluctantly agreed to re-impale herself at the table. And so she'd spent the rest of the night drinking with friends while the huge five and a quarter inch ass destroyer continued to dilate her blown-out rectum to new widths.

She still had that dildo at home in her closet. It often times came out when she had those same girl friends over to drink. Of course, it was never out for very long before it found a nice moist bottom to hide in; usually hers.

"But I only ever observed from the back," she lied. "It's an interesting place. No trappings of the proper society we were raised in, but an interesting place nonetheless," she added truthfully.

"That it is," Naomi agreed, "and thanks for showing me how to fit these things correctly. I can't wait to see how I do with the tips tonight! The customers can see right up me half way to my stomach. That should be worth some extra cash."

"I'm sure you'll knock them dead!" Amanda exclaimed as her eyes stared at the fleshy pink hole leading up into the depths of her sister's abdomen. The four inch wide anal cavern between Naomi's athletic butt cheeks should get her more than enough attention; no doubt about that.