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A Proper Young Woman’s Guide to Anal Etiquette Ch. 06

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. If I can’t stop you I can at least make sure you’re doing it right. Consider yourself disclaimed.

Wilder Evenings

Once again, Cora and Emily are reclining on their beds discussing their days with each other. As would be expected, Cora is dressed in her normal cheerleader’s uniform, which consists of a tight halter-top and a short, pleated skirt. The mere sight of the eighteen-year-old’s large 34D breasts packed into such a tight top, and her amazingly tight ass, would give any teenager – male or female – wet dreams.

On the other side of the room Cora’s sister, Emily, is dressed in a formfitting dark blue sweater and light denim shorts. While Emily’s unbelievably perky 32B breasts were much smaller than her sister’s, on her noticeably more petite frame they actually look very inviting as they strain to break free from the sweater’s thin material.

As both girls laid back on their beds, their conversation was centered around the slight bulges in their midsections; Cora’s tummy was uncovered due to her cheerleader’s outfit while Emily had her sweater bunched up under her small tits.

“And today was worse than yesterday!” Emily continued in dismay. “I mean look at my tummy!” she said, as she poked at the slightly noticeable outline of the three and a quarter inch wide, twelve inch long dilator plug which their sister Amanda had fitted her with that morning after the family’s enemas.

“Well, you didn’t have to wear that tight sweater after she buckled that thing up that small back door of yours, now did you,” Cora responded as she played with the more noticeable bulge of the four and a quarter inch wide, thirteen inch thick dilator plug their older sister had decided to shove up her own asshole. “I’m kind of screwed with this outfit – as I didn’t really have a choice – but you could have changed clothes.”

“Mom said I looked cute in this! And we didn’t have the time anyway. We got rushed into the car too quickly after our plug fitting for me to have run back to the room and changed. And besides, Matt said I look sexy as hell in tight sweaters. I need to make sure I keep him interested in me before our first date on Saturday.”

“Ah… So now it all makes sense! You’re just trying to show off to our very own swim team captain!” Cora said teasingly. “You’d better pick up the pace of your training. He’s from a very conservative family who believes in proper family values. I doubt his mother would let him date a girl who bitches so much about a silly little three inch anal plug!”

“Shut up, slut!” Emily shot back, “And it’s three and a quarter inches thick, thank you very much! Besides, I doubt his mother would be validating my anal training on our first date anyway. It’s not like we’re getting engaged.”

“I wouldn’t be so sure. I have gym with his twin sister, Sybil. You should see the sizes of the plugs her mother fits her with! They’re huge!” Cora said as she made a circle with her hands that was at least seven inches across. “She already has to wear waist cinchers just so she doesn’t cause a scene anywhere she goes. In the shower after gym, it’s easy to see why.

“How was gym class with your plug today anyway?”

“It was horrible! Mrs. Schneider had us doing jumping jacks and jump rope all period! I swear to god it was less for our physical fitness and more so she could watch our tits bounce for an hour!” Emily said with distaste. “And I almost came half a dozen times because of all the jumping around. It was like this stupid plug was fucking me silly every time I moved!”

“Maybe that was her plan too?” Cora wondered. “I’ve seen Mrs. Schneider work a class of seniors so hard that a few of the girls actually did cum from the workout. How embarrassing would that be? Of course, it was all passed off as being out of breath from the strenuous calisthenics, but people know what it sounds like when a woman cums hard; just spending five minutes on the internet will teach anyone that much!”

“Did she get in trouble for embarrassing her students like that?”

“I heard she was reprimanded for it, but that’s about it.”

“Well, that’s stupid! Steven Miller was expelled just last week for getting his girlfriend off in English class. And the gym teacher goes free with just a warning? How is that fair?” Emily asked angrily.

“Dunno. That how it works. I guess if you ‘accidently’ get a student to cum during gym that’s one thing. If you make your girlfriend cum in the back of class because you’re fucking her with her own unbuckled butt plug while the teacher’s lecturing, that’s another.

“Stacey is a whore for letting him do it anyway. I mean, come on! In public?! I wonder what her mother said afterwards. I know what our mother would say.

“And it wouldn’t be anything good!” Cora concluded matter-of-factly.

Emily shuddered at the very thought. “She raised us better than that. I’d let Matt play with my plug in a dark theater – maybe – but certainly not in school. That’s just horribly uncivilized!”

“Well, we were raised properly,” Cora agreed.

“Speaking of English class,” Emily said, changing the subject, “Missy and I were talking before my third period composition and rhetoric class. She told me about the lesson the she got from her mother last night. It actually sounds pretty fun; you interested?” the younger eighteen-year-old asked with hopeful enthusiasm.

“Depends,” Cora responded hesitantly. “I assume one of us has to play the bottom?”

“Well, yeah!” Emily said with her best Valley-Girl impression.

“You up for a switch when you’re done?”

“Of course!”

“Then I’m all for it!”

Emily giggled. “But you haven’t even heard what her lesson was about. How can you be all for it?”

“Babe, Missy and I share study hall together; I’ve heard quite a few stories of what her mother does to her for her training. If what you have in mind is anything like the perverted shit I’ve heard come out of that girl’s mouth, then I’m all for it.”

“Well, okay then,” Emily said as she stood up and began taking her shorts off. “Strip from the waist. We can’t very well do anything perverse with your holes protected by your cheerleader’s bottoms, now can we?”

“Nope,” Cora agreed as she began unbuttoning her pleated skirt, “I actually think my holes have been far too protected all day!”

Lifting her hips up, Cora wiggled out of the small skirt and then raised her legs straight up to remove them completely. At that point, her legs were intercepted by Emily who finished removing the garment for her. Without letting go, Emily lowered Cora’s legs down and sideways; positioning her slightly older sister on her side with her bum pointed straight out. With her sister so positioned, she began unbuckling the strap to the four and a quarter inch dilator plug trapped inside her sister’s nether hole.

Cora giggled at her sister’s unexpected assertiveness. “Nice, Emily. When did you become such a proficient sadist?”

“When I’m horny and my sister is looking so hot in her cheerleader’s outfit, that’s when!” answered Emily.

“But I’m usually wearing this and you’re always horny, so that doesn’t make any sense!” replied Cora as her sister finished unbuckling the large anal violator and began extracting the smooth thirteen inch toy from her pert backside. Cora only moaned at its passage as her own arousal peaked. “Could it have anything to do with your own – very recent – rediscovery of that tiny, barely-fucked-hole you call an asshole?” she said tauntingly.

“Why don’t you just shut up and put that mouth of yours to work on something useful,” Emily demanded as she handed her sister the recently freed – and slightly dirty – plug. Obediently, Cora took the thick tool and began washing its circumference with her tongue.

With her sister silenced for now, Emily stopped to admire the gaping hole between her lovely sister’s athletic bubble butt. Her mouth salivated at the beautiful sight. Licking her lips, Emily quickly pulled Cora’s masturbation kit out from underneath her bed and began rummaging through it for the supplies she’d need. She knew her sister would love what she had in mind. Her own pussy was practically gushing with anticipation. In fact, she was so hot with the scheme of what she had in store for Cora that she hadn’t even bothered to remove her shoes or the sizable dilation dildo from her own sore backside.

In fact, the only thing that excited her more than the torment that she was about to inflict on her favorite sister was the knowledge that she was next.

Or maybe it was the fact that Cora would be the one to do the inflicting.

Slightly confused by the blurred distinction, Emily – undeterred – went about her business of preparing the torment that both of them would soon be enduring.

Updated: December 18, 2016 — 9:34 pm
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