A Proper Young Woman’s Guide to Anal Etiquette Ch. 02

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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 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. Consider yourself disclaimed.


Emily awoke the next morning to the sound of soft moaning and wet slapping coming from down the hall, in the direction of her older sister Naomi’s room. She sat up sleepily and glanced over at her sister Cora’s bed in time to see her pushing her masturbation kit back under her mattress. Cora sat back down on her bed and picked up the substantial rear plug she’d obviously just retrieved out of her masturbation kit and began to lube it thoroughly before she noticed her younger sister had also been awakened by the rhythmic noises coming from down the hall. Cora mouthed a silent, “Good morning,” to her sister before setting the lubed plug conveniently on her nightstand and lying back down to pretend to be fast asleep.

“It’s going to be one of those mornings,” Emily thought to herself with much amusement as she rose slowly from bed; the large plug her mother had forced into her ass during the previous night caused her movements to be slow and measured. “Well, I’d better get myself used to it if mother is going to be taking a more personal role in my anal health,” she continued. And, truth be told, Emily really wasn’t all that upset at the turn of events her life had taken over the past night.

She made her way out into the hall with the bathroom as her anticipated destination. Overly large anal plugs did have a tendency to reduce a girl’s bladder capacity and she needed to use the toilet in a bad way. Halfway there she had to pause outside of Naomi’s room to observe the goings on inside. As she’d expected, Naomi was laying face up on her bed, legs tucked underneath her lithe body. Her weight was supported by her knees and shoulders, leaving her hands free to toy with her young breasts. Laura, their mother, was sitting on the bed between Naomi’s wide spread legs administering to her daughter’s needy asshole. The base of a massive plug clearly visible between the cheeks of the attractive cougar’s shapely ass did not escape Emily’s attention. Her mother had obviously been trying to stir Naomi to full wakefulness for quite awhile now, considering the progress she’d made at opening up her middle daughter’s back hole this early in the morning.

Laura’s forearm was pistoning into the younger woman’s ass, from wrist to elbow, back and forth with forceful, determined strokes; the result of which caused Naomi’s body to rock back and forth in rhythm of the impressive fisting. Naomi was squirming on the bed and moaning loudly with her back sharply arched. Her lacy black nightshirt was scrunched up just below her pert breasts while her fingers were crushing and rolling her very hard nipples as brutally as she could as her hips gyrated in rhythm to her mother’s pounding forearm. Emily could clearly make out the outline of Laura’s deeply embedded arm through Naomi’s muscular stomach, as her mother’s skilled hand rediscovered every nook and cranny of her sister’s bowels. For her part, Naomi was doing her very best to force herself even farther down onto her mother’s arm. Naomi had always been the most masochistic of Laura’s five daughters; which was saying something for a family of overtly masochistic women!

Naomi’s figure bore a strong resemblance to Emily’s: toned and petite but with slightly larger C cup breasts atop her shapely frame. Where Emily, her oldest sister Amanda and their mother all had varying shades of red hair, Naomi had long luxurious brown hair which reached to the small of her back. She’d also done quite a bit of modeling since she was a teenager and never had to try very hard for the attention of the guys; or the girls for that matter. And her appetite for anal abuse, which was on full display to her younger sibling, was on par for all the Wilder women. It was a first-hand illustration of what Emily’s own tender asshole should be expecting from her mother on what was almost certainly to become a regular basis from now on.

Laura jumped slightly as she just happened to notice Emily standing in the door-less entryway to Naomi’s bedroom.

“Oh!” she breathed in obvious surprise, but expertly not breaking her arduous rhythm. “I didn’t see you standing there. I apologize for the delay. I should be in to wake up you and your sister in a few minutes. Naomi here was just having a hard time shaking off the ‘sleepies’ so I figured I’d kadıköy escort help her wake up with a healthy dose of endorphins,” Laura said while looking back down onto her orgasming middle daughter. “An endorphin release first thing in the morning is so much healthier for a young woman that half a dozen cups of coffee, I always say,” she continued, lecturing both of them, as she emphasized her point be driving her arm so hard into her daughter’s spasming rear end that her elbow disappeared from sight. “Come to think of it, it would probably be healthier for me as well,” she added as an afterthought as her mind was drawn to the slab of latex she’d hidden away up her own bum.

Naomi, who’d been orgasming steadily for over a full minute already now, screamed in ecstasy and went absolutely rigid while her mother, her arm still just past the elbow inside the younger woman’s tightly clenched asshole, held finally still. Emily could see the muscles on Laura’s upper arm flexing, and the outline of an arm and fist inside Naomi’s abdomen, and knew her skillful mother was twisting and rotating her hand and forearm deep within her sister’s rectum while Naomi rode her early morning orgasm out to its earsplitting conclusion.

“Why don’t you go lay back down with Cora in her bed and mommy will be by in a minute to get you both up,” Laura said politely to her youngest daughter while her middle daughter was still wrapped around her arm and in full, mind-shattering orgasm mode. “In fact, I’m sure you both have full bladders that need emptying, I know Naomi sure did,” Laura commented while absent mindedly licking the salty taste off her lips. “She always did drink too much before she went to bed and she has no one else to relieve the pressure since Mary moved out. Why don’t you two take care of each other’s morning potty needs the way your mother and aunt Mollie always did when we were growing up together. It’s a beautiful way for sisters to bond!” Laura commented knowingly.

She and her twin sister, Mollie, had always been instructed by their mother to do just that every morning before they got out of bed to start the day. It had been something they’d continued to do even after they’d left home and gone to college together; and, truth be told, whenever they’d slept under the same roof together for family reunions and holidays.

“Yes, mother,” Emily nodded obediently and turned away from the arousing scene of rough anal incest before her to return to her own room and await her mother’s (re)awakening — her original destination of the bathroom having been totally derailed. Reentering her room, Emily went to her bed to retrieve a larger plug from her masturbation kit, knowing it would be needed shortly. She was having a hard time sorting out her emotions enough to tell if she was apprehensive about having a larger plug up her butt this early in the morning or aroused. Just the weight of the latex toy in her hand, as she produced the appropriately large plug from her kit, was enough to put butterflies in her stomach. In the end, she decided it was a little bit of both.

“Wow, Em’! That’s a lot larger than I normally see you volunteering to take!” Cora said in surprise from her prone position in her bed as she watched her little sister pump a few globs of lube into her hand from the bottle on her nightstand and begin to apply it up the seldom used ass stretcher. “And since when are you interested in ‘Mother’s Full Morning Treatment for Sleepy Young Ladies’?” she inquired. “I thought you were headed off to the bathroom like you normally do.”

“I was,” Emily answered as she kicked the kit back under her bed with her foot and sat back down on her mattress. “But Mom suggested that we take care of each other’s bladders the way she and aunt Mollie always do every chance they get. Then she said to wait for her to come and wake us up. I figured that pretty much singed me up for the ‘Full Treatment’ even though I’m already pretty much awake,” she said as her hands worked on liberally spreading the lube onto the toy that would soon find its way into her already sore bottom. The imposing hunk of latex measured nine inches long, three and a half inches in diameter for most of its body with a neck of about three inches at its base; it was the next size up from the plug her mother had decided she wear after she’d been caught in her failed, early morning masturbation attempt.

“Sweet!” Cora declared. “While I’m not as fond of drinking from the tap as mom and her sisters are, I’d never pass up an opportunity to lock lips with that pussy of yours. Of all the girls I sample on a daily basis, I love the taste of yours the best!” Cora said as she threw back her covers and slid over to make room in the bed for her closest sister.

Emily got up from her mattress and crossed the room to her sister’s bed and placed her plug on the nightstand next to the waiting butt stretcher already üsküdar escort there; Cora’s dwarfed hers by comparison. Cora’s chosen post ‘Treatment’ plug was ten and a half inches long, four and a quarter inches in diameter along its length and four inches around at the base; it was two sizes up from the one she had currently buried in her nether hole. As was a normal state of affairs for the horny young cheerleader, Cora was in the mood to be challenged a fair bit. Emily grimaced at the mere sight of it. The thought of something so large going up Cora’s bottom made Emily’s bottom ache in sympathy. Not that its length and girth surprised Emily that much. It was pretty par for her sister’s course.

“So when are you going to stop pussy footing around with that fat ass of yours and start using some properly sized plugs?” Cora taunted as Emily slipped into bed with her.

Cora threw the covers over the both of them and used the motion to bring her hand up to Emily’s semi-hard nipple to give it a healthy tweaking through the thin nightshirt. Emily’s angry retort died unborn in her throat as she sucked in her breath slightly and arched her back in response. That elicited a slight smile from the older of the two high schoolers.

“Still a submissive whore for nipple play I see! Some things never change then. Good,” Cora stated and used her crushing grip on her younger sister’s nipple to pull Emily’s mouth up to her own.

As their lips met, they were quickly parted by young tongues eagerly searching for each other. As the sisters greedily kissed, Emily’s hand wandered down between her sister’s conveniently spread legs to find a very wet cunt waiting for her. And then it was Cora’s turn to gasp slightly as three of her younger sister’s fingers forced their way into her dripping front hole. Not to be outdone, Cora released the grip on the crushed nipple to search out another equally wet hole to hide her fingers in; it took her less than a second to find one.

“When you stop being such a stereotypical cheerleading super-slut!” Emily gasped as their lips finally broke away from each other a few seconds later. She was about to add something else to her angry retort but the pussy slicked fingers of her sister pushing past her lips silenced her. Emily contended herself with playfully biting the hand that was feeding her and smiling at her slightly older sibling as she hungrily sucked her self-made girl juices off the offered fingers.

“You know, I do taste pretty good,” Emily said absentmindedly to her sister as the offered fingers were removed from her mouth and returned to her snatch for another helping. “I can see why you and mom love going down on me so much.”

If Cora was about to add anything in response, she didn’t get much of a chance as Emily’s pussy soaked fingers were brought up to the older sister’s mouth to be sucked clean in turn. Emily’s fingers were quickly cleaned off and returned to the gooey slit from whence they’d come quickly, and the two girls just as quickly locked tongues again while they waited for their fingers to scoop up sufficient amounts of their sweet girl juices. This exchange of deep kissing, pussy fingering and digital tongue washing continued for a minute or two before Emily finally broke the cycle by throwing off the covers and sitting up to turn herself around.

“I know two bladders that will never get emptied if we keep this up for too much longer,” she stated matter-of-factly as she pushed the older teenager onto her back and, turned around in the bed, climbed on top of her.

“I agree,” Cora responded as the delectable girl parts of her youngest sister suddenly appeared above her, only inches away from her eager lips. “Mom will never get those plugs up our butts without us pissing everywhere from the pressure on our bladders if we don’t take care of the problem first,” she stated as a matter of fact.

It was normally part of ‘Mother’s Full Morning Treatment for Sleepy Young Ladies’ for Laura to drain the young lady in question’s bladder herself, partial as she was to the act, but it wasn’t the first time Emily and Cora had handled the function on their own; and they’d been taught very well how to drain both male and female bladders without spilling a drop as part of their proper upbringing.

Cora wrapped her arms around the torso above her tightly and pulled down; forcing Emily’s already spread legs to open up even wider. This maneuver also brought her lips into contact with the moist teenage pussy between them causing Cora to sigh in contented bliss as the heady aroma filled her mouth and nostrils. She felt the lips of her younger sister make contact with her own drenched cunt and a well-educated tongue began to go about its work; Cora let out another contented sigh in response.

Cora bathed the offered cunt before her with her tongue, from taint to clit hood and back again, greedily lapping up the juices she found within. She could tell from tuzla escort the feeling emanating from her own young pussy that Emily was doing the same for her. Truly, the age old and time tested 69 was the ultimate bonding experience for any pair of sisters, and Cora and Emily were no different. The fact that their mother and aunt Mollie were as close as they were and that they engaged in the very same pastime so often was another example of the bonding power of the sisterly 69.

Emily only let this go on for a minute or two before she found the wherewithal to remember that there was a purpose to their activity other than their normal playful, sisterly games. If it were up to the two horny sisters, Cora and Emily would continue give each other orgasm after orgasm until they were late for school; it’d happened a few times before when their mother had had to go to work early and they’d been left to their own devices.

Pausing in the tongue bathing of her slightly older sister, Emily closed her lips over her sibling’s urethra and sucked hard. She was rewarded with a small spurt of warm salty liquid, but not the torrent that she was expecting from the bladder of an eighteen year old after a good night’s sleep. This was not totally unexpected and Emily thought back to what her mother had taught her to do in such a situation. The memory was when Laura was first teaching her how to force a woman’s bladder to give up its contents. At the time, mother and daughter were locked in a passionate 69 while Laura gave directions to her youngest daughter in-between her own cuntoral administrations and gasps of pleasure.

“Now, Emily — Uuuung! Right there! — when you’re ready to drink up but the owner of the pussy you’re sucking on is too distracted to let loose, here’s what — Fuck yes! — you do. If her bottom hole is empty, like yours is now, you need to — Oh God, yes! Nibble on mommy’s clit just like that! — push your hand up her ass and press forward against her bladder. The pressure — Mmmmm… Harder! Nibble on mommy’s clit harder! — on her bladder will cause it to empty without her having to let go of the muscles voluntarily. She should be excited enough to — Oh, baby… baby… baby! Mommy taught her little girl so well! — be really lose back there and your hand should be able to slip right in. […] See? You barely noticed my hand slipping past your ass ring did you?

“Now for true anal sluts like you and me, you may want to make a fist and pop it past her sphincter a few times to — Oh my! This is turning you on, isn’t it? Can you suck on mommy’s pussy a little harder? Uuuung! There you go! — get her juices really running. Take your time and really have fun with the defenseless ring of muscle. Now, I’ll just slip my fist in and out of your little asshole a few more times and — Oh god! Mommy’s soooo close! — you should be ready to drain your bladder. […]

“There we go. I always find that a few dozen fist reinsertions are always what a well train ass needs to really get in the proper mood. Now, do you notice that when I burry my fist up your ass and press — oh yes, baby. Yes! — forward firmly it gets harder and harder for you not to pee? Alright, now I’m going to push forward hard and you’ll be unable to stop from peeing down mommy’s throat. Don’t worry about choking mommy; mommy knows what she’s doing. Just let it flow. […]

“My, my, Emily! That was an awfully full bladder! Mommy’s not going to be thirsty for awhile! Okay, now while it’s not necessarily part of tonight’s lesson, I hope you don’t mind but I’m — Oh, baby! Just like that! Mommy’s pussy needs that! — just going to keep my fist up your ass for right now. Anyways, now if her bottom hole is packed full of latex, like mommy’s is, you need to force the pee out of her a little differently. Now pull mommy’s plug about half way out and — Tongue! Use your tongue a little more! — shift it 45 degrees so that the tip is right up against the bladder and press forward forcefully. Now, be sure your lips are sealed around mommy’s urethra tightly. You don’t want to let any leak out. Now you try. Ummm… The bulk of mommy’s plug feels so nice stretching mommy’s dirty ass like that. Feel free to rotate it a few times in mommy’s sloppy hole. Remember what mommy said about having some fun with a non-resisting sphincter? Ooooo… That’s better!

“Now, shift it and press forward. There you go. A little harder. Harder! Oh shit! I’m pissing! I can’t turn it off! All of mommy’s hot piss is shooting right out and mommy can’t do anything to stop it! Good job, Emily! Keep gulping it all down. Push the plug forward a little harder. Uuung! There you go. Make sure to drain as much out as you can. Don’t spill any. Suck really hard to get out those last few stubborn drops.

“I think mommy’s empty now. Good girl! That wasn’t so bad now was it?

“Now normally, you would go ahead and shove the plug back up mommy’s ass and continue to eat her out, but mommy wants to cum really hard now so go ahead and take the plug out and set it aside. Grab that large veined dildo we used on mommy’s ass earlier tonight when we were learning about being stretched to maximum capacity. Yes, the really big one that made mommy cry. It needs to go back up mommy’s bottom again. Mommy was bad for crying so pathetically in front of her baby girl and need to be punished.

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