A Proper Young Woman's Guide to Anal Etiquette Ch. 01

As Laura went to retrieve Emily's masturbation kit from under the bed, Emily was treated to the appealing -- despite herself -- sight of the base of a truly massive plug protruding from her mother's shapely ass as she bent over. "Damn!" Emily thought to herself. "A girl has to work hard at that for decades to take something like that up her butt and walk around like nothing was amiss." Which was exactly how her mother had accomplished such a feat. Laura had had just as proper of an upbringing from her parents as Emily and her sisters had had from Laura and Dave. As big as she knew the plug was up her mother's rear end, and only God knew how big it actually was, she knew that her mother was capable of taking much larger; much, much larger. She was just going easy on herself for her nighttime plug. Emily felt the familiar surge of lust and admiration she always felt when she saw her mother's distended ass from so close. The sight before her restarted her previously stalled arousal; all thought of Matt lost for now. A girl just couldn't grow up being personally involved in as much mother on daughter, or sister on sister, sex and not be turned on at such a view! She was her mother's daughter, after all, and despite her own preferences, there was anal work that needed doing. The fact that the 'anal' in question was in reference to Emily's own, uncooperative back hole was a minor point.

"Ah! Hear it is!" Laura quietly exclaimed quietly, still trying not to wake Cora, as she hauled the large suitcase size kit out from under the bed. "There's actually dust on this thing! We need to spend a lot more quality time together, you and I, young lady!" Laura exclaimed. Emily's masturbation kit was pink with Hello Kitty stickers stuck all over it; she'd always had a thing for the franchise; even today. The fact that such a cute box held such sinister tools of anal education, inevitably targeted at the youngest Wilder daughter's illogically resistive anus, had always so turned on all of the other women in the Wilder household was no secret to anyone. And it was about ready to be opened back up to administer an aptly deserved lesson to the young woman in question. The well used kit was placed on top of Emily's nightstand and reverently opened, revealing the tools with which Emily's back hole would soon be abused with. The top of the kit contained a row of a dozen flesh colored, realistically veined, dildos ranging from two inched thick and six inches long to a whopping five inches thick and eighteen inches long, as well as a row of twelve similarly sized butt plugs just beneath. There was an empty spot in the lineup of butt plugs where the plug that was now being diligently tongue washed in the teenager's mouth would nominally be stored; it was the second smallest one. The bottom of the kit contained an assortment of miscellaneous tools: inflatable butt plugs, nipple clamps, anal beads of various and frightening sizes, magnetized dildo harnesses, magnetized chastity belts, magnetized suction cups, magnetized handles, several more specialized plugs and dildos, a few punishment catheters, ball and dildo gags, etcetera. Fun things like that. Although, there was nothing present in the kit that wasn't a common enough teaching aide for any young woman of proper, conservative upbringing.

Laura selected the three inch wide, ten inch long veined dildo form its storage place and gently massaged it as if it was a real cock. "Ah. The veined dildo: A girl's first line of defense in the never ending battle against having an asshole that's too tight." Laura observed as she reached back into the kit for some lube and a magnetized handle. "We'll start with this one tonight and work our way up something more fun another night." She commented offhandedly. The plugs and dildos themselves were all magnetic and could be attached to a multitude of accessories. The handle Laura had selected and snapped onto the intimidating dildo was a sturdy two handed affair; perfect for getting a firm grip with both hands to drive whatever point had to be made home into whatever resistant hole happened to be available.

Her tools selected, Laura moved to the foot of Emily's bed and crouched down between the reclining teen's widely spread legs as her daughter continued to finger her already slack rear hole. "Go ahead and get your fingers out of mommy's way, dear." Laura instructed. "Just pull your cheeks apart and help mommy stretch you out a bit more by staying relaxed." Laura continued and Emily immediately complied. Laura paused for a moment to appreciate the view and wonder if her own ass had ever had that small of a gape; certainly not for many, many years. Maybe when she was sixteen and had been having sex with her then boyfriend for almost a year, but certainly not long after that since her parents had found out about the affair soon thereafter and had started her anal dilation training almost immediately. The yawning black cave that was Emily's rectum was clearly visible in the soft light, just below her obviously moist pussy. Her hands were on each ass check pulling them apart as hard as she could but the open hole itself was only a pitiful two inches across at its widest point. That was just unacceptable in any daughter of Laura Wilder's!

Laura set the formidable tool to the side for the moment to quickly dip two, then three, then four fingers of her right hand up her daughter's rear. In no time at all, she had half her hand buried into the quickly expanding back hole of the young woman; all the way up to her perpendicularly extended thumb. "Emily may not play with her cute little butt as much as I know she needs to for a girl her age, but her butt itself certainly remembers the lessons I've taught it in the past." Laura thought as Emily gasped and moaned softly at the intrusion into her most private orifice. With her hand so buried, Laura began rotating it 180 degrees, clockwise and then counterclockwise and back again, inside of her daughter's ass; trying to get the maximum amount of dilation for the minimum amount of effort. Aloud: "Shhh. Now quite down, baby." Laura's hand went through another series of twists and thrusts as her daughter gasped and moaned at the intrusion. "You don't want to wake up your sister, who's sleeping so soundly, just because you needed your mother to remind you how to properly treat this little hole of yours." She reinforced the point by turning her hand towards the bed and pressing firmly downward. Emily gasped as empty black nothingness appeared above Laura's hand. "Good" Laura thought to herself. "Let's open this up a little more before we start playing for real." Emily's mother placed her left hand on top of her youngest's pubic mound to hold her steady and then began pulling the no longer overly resistive sphincter in all directions with the four fingers of her right hand already burred into the young orifice. This continued for several moan filled minutes as the loving mother worked her daughter's pliable hole open wider and wider, quite literally, with a skilled and knowing hand.

In no time at all Laura was able to see at least an inch of spare room above the top her hand no matter which direction she pulled the willing young asshole. Not allowing her daughter to get comfortable with the level of dilation she was already experiencing, Laura quickly folded her thumb over her hand and pressed her fist forward; it quickly disappeared up Emily's backside with only a soft 'sluuuurp' to mark the occasion. Emily was a bit more responsive than her compliant asshole to the situation as she let out a -- none too soft -- moan of mixed pain and building pleasure. "Emily!" her mother, as quickly and as silently as she could, admonished her daughter. "Mind your volume or I'll fetch one of your penis gags out of your masturbation kit and mind it for you! And it will neither be a thin or a short one!"

"Sorry, mother." Emily responded much more quietly, her volume now under control. "I'll try to -- ungh -- keep it down." The chastened teen apologized to her mother under her reproachful glare as the older woman began twisting her now closed fist around the inside of the young woman's rectum.

"Honestly, Emily. If you would have just taken care of your own hole's basic needs, I wouldn't have to be doing it myself at half past the ass crack of early in the morning." Laura continued, berating her daughter as she moved her first around inside the sloppy hole of her daughter's ass, ensuring no spot was left unstretched. "You think I don't have my own needs I could be satisfying right this very instant instead of teaching you how to do something you should know how to do yourself by now?" she continued. Emily, wisely -- except for the odd moan and gasp -- continued to remain silent as her mother worked her rear hole over to her satisfaction.

A few quiet moan filled minutes of expert motherly fist to daughterly ass lecturing passed into eternity; Laura nodded to herself and slowly withdrew her hand from her daughter's now quivering anus. "There now; that wasn't so bad. You should be all nice and stretched out for a proper buggering. Now turn over onto your front, reach back and spread your cheeks so mommy can make you feel good. And I don't want to hear a word of protest from you, young lady!"

Emily, her aversion to anal all but forgotten in the heat of the moment, didn't need any further encouragement. She quickly flipped herself over onto her belly, raised her butt invitingly off the bed and spread her shapely legs. Reaching back with both hands to spread her now much looser nether hole open to her mother's administrations, she lay breathing heavily with her butt slowly and unconsciously rotating in lazy little circles in its anticipation of more attention from her mother.

As Laura picked up the veined dildo she'd selected as she briefly admired her handy work in the now over two and a half inch diameter vortex leading up her daughter's backside. The pause was only a brief one as she readjusted herself on the bed to rise to her knees and line up the toy with Emily's needy ass. The change of position momentarily reminded Laura of the presence of her own large toy, safely wedged between her own ass cheeks, as it shifted welcomingly. But it was a momentary distraction as she refocused on the task at hand. With just little forward pressure, the head of the large dildo slipped past Emily's too tired to resist anus and, inch by satisfying inch, the thick tool made its way unimpeded into her daughter's moist bowels. All Emily could do was sigh and moan appreciatively as the entire ten inch length of the realistically shaped dildo was sheathed into her pert backside. Seeing any one of her daughters bent over with their butt in the air and a double handed dildo handle protruding from between two young and toned cheeks always gave Laura an internal chuckle. And she'd seen every one of her daughters in that very same position more times than she could ever remember. "Like Arthur and the Sword in the Stone, I'm Laura and the Dildo in the Daughter!" she giggled softly to herself as she did her best impression of her imaginary, heroic self. Single handedly, she grabbed the mythical 'sword' and began extracting the 'blade' from its 'rock', letting it pop free with soft sucking sound. "Proving once again that I'm Queen of the Wilders Bitches!" she proclaimed proudly to herself, smiling at her private fantasy. "Unlike Arthur, though, this 'sword' needs to go back into its 'rock'. And then out again. And then back in yet again. But faster. And with a lot of repetitions." she continued to herself as the smile on her face disappeared right along with the large faux cock back up her daughter's still lazily rotating bum. Emily just continued to moan softly -- totally unaware of the strange direction her mother's thoughts had taken -- as her bum was subjected to the penetrations of her mother's unstoppable tool.

Getting serious now, Laura grabbed the handle of the large dildo with both hands, over handed in the way a person from a few centuries ago would have churned butter, and began to pick up the pace. Emily was soon getting her butt truly and properly reamed. The veined toy was being extracted to the point that all but the last inch or two of the three inch wide monster stayed inside her sucking anus and then the remaining eight or nine inches would quickly be rammed back in so deep that the hilt at the base of the dildo made a soft, wet slapping sound as it made contact with her tautly spread cheeks. In fact, 'churning butter' wouldn't be a bad metaphor for the hot and sexy display.

The minutes dragged on and the pounding continued unabated. Emily was now sweating and writhing on the bed unabashedly while she bit down on her sheets and tried not to moan too loudly as she lost herself in the ecstasy that was radiating from her abused bottom. "I just hate it when my mother is right!" she cursed to herself as her previously lost orgasms resurfaced and again began washing over her again. "Awe, fuck it!" she conceded defeat and bit the sheets harder still; the large slab of latex continuing to ravage her pliable, young, rearmost hole.

Laura was sweating too, but from the upper body workout she was getting as she pile drove the three inch thick butt stretcher in and out of her daughter's sloppy rear end. "I should really be wearing a sports bra" she thought to herself as her massive mammaries swung violently back and forth in cadence to the pounding she was giving her youngest daughter's neglected rectum. Laura had enough sweat glistening on her toned body now that her large breasts were making a slight slapping sound of their own as they slammed into each other every time she bottomed out in her ungrateful teen's upturned ass. As her large breasts swayed back and forth, the thumb sized nipples topping each orb were getting a very nice tickling as they rubber across her babydoll chemise and had long since become hard as diamonds. She really wished she had a free hand or two so that she could give the stiff nubs the proper tweaking, pinching and rolling they desired. "You can take care of your own needs later, you horny vixen! Your daughter needs you right now." She promised herself as she continued the downward thrusting of the thick anal pacifier.

Despite her personal promise of a later reprieve, she'd already gotten quite worked up; Laura could feel her juices freely running down the inside of her thighs. Between the close up and personal view of her sexy teenager's most private hole being viciously brutalized by a large and relentless tubular intruder and her own renegade nipples being stimulated to the point that they felt like they would soon burst if someone didn't bite down on them soon -- and preferably very hard! -- she'd neglected to keep her own well trained bottom clenched down sufficiently enough on the nighttime plug that was situated deep inside her own most private hole. Too late she realized that her stimulated and relaxed sphincter had failed in its job entirely and the huge rectal dilator was slipping past her most intimate defenses; it descended almost a full foot to rest on her daughter's bed. Laura gasped in unexpected delight as her anus stretched pleasantly around the thick plug's four and a half inch diameter body. Her sphincter had just been expanded, without her explicit permission, from the mere four inch thick base of the impressive plug. And despite the next best thing to an entire foot of latex toy which now reached from the toned cougar's widely stretched butt cheeks to the sheets of her daughter's bed below, nearly as much of the thick bitch tamer still remained deep inside of Laura's suddenly grasping ass as what had accidentally slipped out.

"Damn it!" she quietly cursed to herself, trying not to interrupt the sawing rhythm of the -- now, relatively appearing, very much smaller-- toy into Emily's orgasming, upturned ass. If Emily had noticed her mother's soft outburst she gave no hint of it; lost in the waves of anal orgasm that she was. Laura bit her lip in consternation as she tried to decide what to do; a half inserted butt plug was a distracting quandary, no matter what its actual size was. As quickly as the indecision came her mind, her body made its own decision; which Laura discovered a few seconds later as she finally noticed that her hips had already began to ride up and down on the smooth shaft piercing her cheeks. "Oh God yes!" she hissed to herself, throwing her head back in pleasure. She intentionally picked up the pace of her hips, needing to abuse her own needy hole more than ever now.

Despite the sheer size of the massive plug stretching her humble bottom, which was now being driven into the horny mother's ass by her very own body weight, the fact remained that it was still just a smooth nighttime plug designed for comfortable, long duration wear; it wasn't textured for short term pleasure. Laura soon groaned to herself in resignation to that fact. There was no way this was going to get her off. All this was doing was frustrating her still further and increasing her already running at full steam libido. "At least I don't have to keep this up much longer" Laura commented to herself as she noticed that her daughter's steadily building orgasm had hit its earth shattering climax. The younger woman suddenly went rigid and flattened herself on the bed below, emitting a muffled scream into the mattress. Laura immediately changed the challenging rhythm of the ten inch invader which was punishing Emily's tightly clenching bottom to a different one designed to push Emily's already strong orgasm just a little bit farther. She slowly withdrew veined tool to the halfway point and quickly, and much more forcefully, thrust it inwards as hard a she could; trying to burry every fraction of an inch into the teenager's spasming butt. Emily only grunted between her otherwise continuous screams as the three inch thick daughter tamer slammed into her quivering anal ring so hard it shoved her forward an inch or so with each thrust.

Again and again the skillfully employed toy slammed into Emily's barely coping sphincter. Again and again Emily grunted against her screaming, continuous orgasms as she was forced forward inch after inch by the forceful impact of firm, unyielding latex against the supple and all too yielding teenage flesh of her no longer resisting ass. Finally, totally spent, Emily went limp on her bed as her mother ceased the savage assault on her helpless back hole. All she could do was lay there and gasp for air and try and regain her senses.

Laura, also breathing hard, but for an entirely different and unsatisfying reason, leaned back on her heels to get some much needed air. The humongous plug resting on the bed beneath her slid still further up her butt as she did so, eliciting as soft sigh of desire from her lips. Quickly refocusing on her daughter she asked "See there? That's what your body needed. Not that silly thing you were doing to yourself when I came in here half an hour ago." she said reassuringly to her daughter as she leaned forward to softly squeeze and caress the cheeks of her daughter's still fully packed ass. The double handed handle sticking out between her daughter's pert butt cheeks was once again all that was visible of the ten inch toy. All Emily could manage in response was a jerky nod of agreement as her voice was still beyond her ability to control. Laura continued to massage her daughter's firm butt cheeks for a moment or two, enjoying how her manipulations of Emily's derriere caused the latex handle to flop tantalizingly this way and that, then lovingly patted her daughter on the rear and sat back up again. Reaching between her dripping pussy lips to the thick, smooth plug beyond, Laura grabbed hold of the base and began reinserting the entire length into her horny back passage until her sphincter closed around the four inch thick base, against its will, once again. Forcing it to accept a smaller diameter toy than it had inadvertently grown used to was not something she desired at this moment either. Her slutty, insatiable, rear hole demanded something larger, and with a pleasing texture; and she knew it. A demand she intended to placate as soon as she finished with the maternal nurturing her daughter currently required of her and she was able to return to her own room; and her own waiting masturbation kit with its considerably larger weapons of ass destruction.