The Zip Files Bk. 02: Zip Does Gymnasts Ch. 02

Episode Two of 'The Zip Files': Zip Does Gymnasts

Chapter Two: Denise Sablier Teaches Anal

Our Story Thus Far: Zack 'Zip' Zilch, the biggest loser in wealthy San Cajetan High School, has recently discovered that he has the ability to control women's clothing with his mind - among a few other erotic powers. In the first chapter of book two, Zip secured a trip with the San Cajetan High women's gymnastics team to a crucial meet. But, the night before what promises to be a weekend spent hanging out with extremely fit ladies wearing skimpy leotards, he returns home... to find his teacher Mrs. Denise Sablier waiting for him. Turned on by a trick he played on her earlier in the day, she has decided that the time has come to give him a very intimate lesson.

Note: while there are a few tidbits herein that become relevant later, this is for the most part just an extended anal sex scene. If you are for some bizarre reason reading this series for the plot, and/or just not that into this particular act, feel free to skip this one and pick up with chapter 3.

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While this is Zip's sophomore outing rest assured - all characters in this work are over the age of eighteen.

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Kneeling upon his bed, looking back over her shoulder, Zip's biology teacher slowly waved her large round ass back and forth impatiently.

Staring at it, Zip swallowed. Then, he slowly started to approach her.

Since he had come into his powers, he had gotten somewhat familiar with the delightful confines of the gooey self-lubricating pussy. But he had not gotten up inside the back door at all. Anal sex was something he knew of only from hearsay, school-yard rumors, and porn. Just about all he knew about it was that it was supposed to be very special...

Arriving just behind her, he reached out and stroked Mrs. Sablier's round ass, as it wiggled back and forth before him. He gave her deep firm buns a couple squeezes, marveling, and imagining what it might be like to be up between them.

"Have you done this before?" he asked her.

"Many years ago," she said. "It used to be a... a special gift I would give a guy. Es... especially if I didn't want to risk getting pregnant."

She sounded a little nervous. Zip gave her big ass-cheeks another couple of squeezes, contemplating how thick and round they were - and the little anus waiting between them.

"So you didn't enjoy it yourself?" he asked her, curiously.

Mrs. Sablier swallowed - and then shook her head. "N-no of course not," she said.

Zip was pretty sure she was lying - but didn't call her on it.

"I've never done it with my husband, though," she continued - squirming, as he gave her ass-cheeks another squeeze. "I... I didn't want him to get used to it. Or to think I was that kind of woman..."

"What kind of woman?" Zip asked. He gave her ass another squeeze, in from the sides - making her big cheeks smoosh together.

"N-never you mind that!" Denise snapped back over her shoulder.3

Zip nodded. Taking his hands off her ass he stepped back, and started taking off his clothes. But even so, he could not help thinking.

"So, if you've never done it with your husband, then you haven't done it in..." he said, taking off his shirt. He let the thought trail off.

Denise swallowed, looking down into his bed.

"Many years," she admitted. Her buxom ass gave another wiggle, as if she had suddenly been overcome by nerves, before him.

Zip nodded - and then finished taking off his pants. Standing behind her, naked, he reached out and once more put his hands on her ass. He gave it another couple squeezes, while its vast round contours wiggled nervously in his grip. Then, he spread her big cheeks apart... and blinked.

"What's this?" he asked.

Between her buttocks, he had finally noticed something. Her buns were so deep that it had previously been hidden amidst the deep shadows between her cheeks. But now he saw it: a clear plastic disc covering up her anus. He also noticed that her asshole was not puckered up all the way, but was spread ever so slightly - forming a dark portal, through which he seemed to be able to see deep into her body...

Reaching out, he touched it. Denise promptly shivered, and let out a tiny moan. Then she craned her head back around and looked up at him.

"That's a butt plug," she told him. "The wide base ensures it can't vanish up into me."

"Oh," Zip said. "I mean, uh, of course!"

This was his first time encountering that particular tool in person. Reaching out he caressed around the base. He noticed that even that slight stimulation, carrying up into her asshole, made her entire buxom body quiver, upon its hands and knees before him - giving him a hint of what he was in for.

"What's it for?" he asked, curious - as he continued to play with the plug and, by extension, her.

Mrs. Sablier licked her lips, and squirmed back and forth. She was presented before him upon the bed like she was offering herself up on a platter, naked pussy and anus and all, and did not seem to be able even for a second to forget that fact.

"Well..." she said. She paused a moment, her lips quivering as he gave the plug another turn, then licked them, and softly continued. "In some ways it... it's kind of just another toy. Some women use them a bit like a vibrator, just to stimulate themselves. But... it also has... other purposes..."

Her voice was becoming husked, and coming with some difficulty, the longer he played with it. Despite her earlier protestations about not enjoying anal, he could not help but notice that her pussy was steadily getting wetter and wetter, the longer he toyed with the plug inside her anus.

"Like what?" he asked her, while continuing to twist the ring back and forth - marveling at the way that simple act made her busty body shiver.

Denise swallowed, and then let out a little sigh - her curvy hindquarters shifting back and forth, as he teased her butthole with her own toy.

"Well..." she whispered. "It's... it's kind of tight back there. Legendarily so, in fact. For some men, that's... kind of the whole point. But, if it's too tight, you won't even be able to get in. So, a decent girl who doesn't just give this up every time needs... needs to stretch herself out first. That's... necessary enough with any guy. But... doubly so with a... an over-endowed little brute, like you!"

And with that last cutting comment, after many long minutes of admirable self-restraint, the buxom and naturally-imperious teacher finally swung her gaze back, down and back between her legs - and gazed upon her student's penis. A tiny whimper emerged from her lips as she saw the immense beast Zip was blessed with, swaying back and forth behind her - just past her own nakedly dripping pussy. A look of trepidation briefly appeared upon her pretty face at the knowledge that, tonight, for once, it would not be that increasingly and obviously wet pussy it would be wrecking. But then, before she could give up too much of her pride, she tore her eyes away, lifted her head up high - and tried to pretend she hadn't been staring.

"I see..." Zip said.

Then, tired of playing with the plug inside her, he decided to take it out. Seizing it by a firm grip at the base, he began to tug.

Denise let out a stunned moan and put her head down, her entire body shivering, as it was slowly extracted from her. Zip stared in fascination as a variety of interesting and rather barbaric-looking contours pulled their way through the quivering tautness of her anus. At last, the fiendish plug tapered down to a rounded point. Her asshole kept a tight seal around every fraction of a millimeter as it came out, giving yet another foretaste of what his penis was in for. At last, it slipped out. Keeping her head down, Denise sighed, and wiggled her buxom hips back and forth with relief.

"God damn..." Zip said. Lifting it up, he studied it. Now that it was out of her the butt plug looked like an abstract art piece, with many swooping curves and flaring circles. Like someone had captured a slow-motion water-drop in eternal crystalline form - and then decided to shove it all the way up until it was nudging her colon. He was surprised how long it was. As he turned it back and forth, viewing its many contours, he was struck that, based on a few whimpering comments she had made here and there, it was among other things quite a bit larger than her own husband's penis...

"It's big," he commented, still studying the plug.

Panting hard, Denise nodded slowly, and then swallowed.

"I... I had to work myself up to that one..." she said. "First with just a little one. Then... a bit bigger. Then... then that behemoth." Said behemoth was, very noticeably, still at best only a small fraction of the total volume of her unruly student's penis.

Zip's eyebrows went up, still studying the plug.

"Work yourself up?!" he asked, surprised. "How long have you been wearing them?"

Denise bit her lip and blushed slightly. But ultimately she took her role as his teacher seriously, and could not help but answer.

"A few days... each..." she said. "About a week... total..."

Zip's jaw dropped.

"A few days... each?!" he said. He glanced down and stared at her buxom form, wiggling naked before him. "So... so that means this entire time, this past week... whenever you were teaching class you had..."

"One of those in my ass... yes..." she said.

Still staring in awe, Zip thought back to the last several days. To the succession of short, tight skirts his teacher had worn as she strutted her buxom ass back and forth in front of her classroom... and suddenly completely revised his mental image of what had been going on inside those skirts, every single day.

Then he looked down at her, at the back of her pretty head - and a sly smile slowly spread across his lips.

"So, let me get this straight," he said. Reaching down, he began to caress the tip of the butt plug back and forth, across her rounded buns. "You wore this in your ass for an entire week... including every single day you were in class... just so you could teach me a 'lesson'?" he asked. His smirk broadened. "I find that hard to believe..." he said, stroking the plug back up and across her rounded ass.

Turning her head up, Denise gave him a sharp look.

"Well... well you'd better just believe it, then!" she snapped. "Now get on with it!"

"Okay..." he cooed.

Still smirking, he did so. But perhaps not quite in the way she had intended. Slipping the now superfluous plug down, in between her naked thighs, he brought it close to where her vagina waited - unattended and drooling.

But the reaction, when he first touched it to her there, was not the one he expected. The moment she felt the hard tip caress her outer pussy lips her jaw dropped and her eyes spread wide as she realized - based on the fact that the hardened girth she felt pressing into her was merely intimidating rather than completely dominating - what it must be.

'Wh-what do you think you're DOING with th-that THING?!" she screeched. Her curvy hips recoiled forward, drawing her precious slit away from the toy.

Zip blinked.

"I was going to slip it up inside you," he said. "I figured you'd enjoy feeling it in there, while we fucked."

Rolling over, Denise lay on her back before him, facing her big ass into the bed - and then squeezed her thighs tight together, to help protect her naked pussy. Then, glaring up at him, she shook her head back and forth.

"You can't do that!" she snapped. Lifting up a hand she pointed it back at the plug. "That thing's filthy."

Zip glanced down at the clear plastic and frowned. "It looks clean enough," he protested.

"Only because I cleared myself out, first," she said. She nodded down to the two enema kits, one used and one new, lying at the foot of the bed. "That's the first thing those videos of yours lie about. I mean... most men aren't long enough to get to the colon, it's true - though you are undoubtedly an exception. But, even if you didn't get all the way there, sooner or later there will be some... you know."

The studious teacher, who he had personally witnessed detailing a great number of disgusting biological processes in enthusiastically clinical detail suddenly seemed momentarily lost for words - now that she was describing something coming out of herself.

"Filth," she finally settled upon - her lips quivering, in the wake of the word.

She took a deep breath, making her enormous bare breasts slosh upon her chest, then continued.

"So, I flushed myself out in advance. Because personally? I don't like dealing with that sort of thing during sex. It breaks up the flow. E-even if I am not getting anything out of it, and am just doing it as a gift, mind you!"

"Okay, well then you cleaned yourself out," Zip protested. "So, what's the big deal?"

Denise rolled her eyes, and scowled.

"Okay, so apparently I need to go back and give you an F in germ theory," the irate biology teacher hissed. She nodded towards the plug. "Just because you can't see it, doesn't mean there's nothing there."

Rolling over, she glared up at him. Then she reached up, fluffed her hair, and sighed.

"Look," she said, visibly calming down after the initial rush of panic she felt, at feeling the plug touch her pussy. "First lesson. You can go from front to back... but you can't go back to front." Reaching down, she pointed at her leaking pussy. "It's a very delicate environment down there," she assured him. "You don't want anything biologically active down there. The consequences can be quite... intense." She squirmed, as if multiple sorts of memories were running through her head. "That counts for toys, for your penis - for everything. Got it?"

Zip frowned.

"So if I fuck an ass, I can't fuck a pussy?" he asked.

She shook her head. "Not mine, at least," she said. "Not unless you disinfect every inch, crease, and ball-hair first," she said.

Zip thought about this and then shrugged.

"Fair enough," he said - bowing out of the argument, without actually agreeing to her terms. Reaching out - being careful to grip it only by the base and not the business end - he put the butt plug down upon his nearby desk. Then he turned back to her.

"So, now what?" he asked her.

She bit her lips, studying his giant cock.

"Well... normally I would say you at least owe me some foreplay first," she said, still staring at it. "But, I know you have an early morning so... and I already stretched myself out with the plug, so, let's just get to it." Rolling back over and presenting her ass to him, she looked back up over her shoulder.

"Second lesson," she said. "Unlike the vagina, it doesn't provide its own lubrication. So... you have to." She glanced down to the several bottles lying at his feet. "That's what those are for."

"I see," Zip said.

Reaching down, he picked up one of the bottles. He poured it all over himself. He had a lot of cock to cover, so by the time he had himself sufficiently slickened up from end to end he had used pretty much the whole bottle. Then, to help keep himself enthused, he reached out and caressed his tip against her buttock. Denise moaned, softly - and rubbed her rounded bun back up against him.

"What now?" he asked.

She bit her lip, and looked back over her shoulder.

"Well... now you just put it in..." she said. She glanced down, swallowed, and squirmed. "If you can..."

"That's it?" Zip asked.

"I... never said it was that complicated," she pointed out, kneeling and waiting before him.

He nodded. Then, reaching out, he took a firm grip on her curvy hips. Slowly, he brought his mammoth tip forward.

He noted, in an odd moment of reverie, that it was much easier to see what he was doing, since his target was right in front of him rather than hidden down between her legs. He felt her enormous buns rub against his cock-head, jiggling softly against its flared crests, as he slipped down between them. Then at last, like a missile reaching its target, his enormous tip slammed down into her tightly puckered anus - and stopped dead.

"Oh... shit..." he said.

He could feel some give in front of him, especially in the very center. But still, it felt almost like he was trying to shove his way right through a random part of her skin. He tightened his grip on her buxom hips and shoved harder - but got no farther. His immense tip rolled around against her taut entrance, pushing it open very slightly - but mostly seeming only to grind inside her shallow bowl like a pestle being vigorously stirred within its mortar.

"Am... am I doing something wrong?" he asked, after about a minute or two of this.

Her breath coming in quick pants, Denise shiverered, and then rapidly shook her head back and forth.

"No! No!" she gasped. "J-just p-push... h-harder!"

Encouraged by this request, he redoubled his efforts. He slammed his gigantic hardened penis into her again and again. And he marveled as, very very slowly, her tight entrance opened up for him.

"Oh... holy shit..." he gasped.

After having gotten rather used to having his way with her pussy, this was like an entirely new experience. It was kind of like a too-tight condom was being steadily advanced up his cock, yet while still squeezing and clamping down upon it continuously. Only gradually and reluctantly did it give way before him as his incessant probing allowed him to wriggle and worm his way into her, one tiny little fraction of an inch at a time.

At last, the flared head of his cock pushed through the taut opening of her anus. And, as if passing through her threshold, he suddenly shot down deep inside of her - to immediately find that same crushing clenching tightness bearing down on him from all sides.

"Oh, fuck!" Zip groaned, as he felt himself finally filling his haughty teacher's big round ass. It felt roughly like he was inserting his penis through her anus and directly into the center of a black hole.

"Oh... m-my fucking GOOOODDD!" Mrs. Sablier squealed - in a way he had not heard from her since the first several times they had had sex.

Finally he slammed to a halt inside her. Her enormous buns pressed and wiggled up against him, all around the base of his cock. And, as he rammed in all the way within her, his gigantic balls swung up - and, fortuitously, slapped right up against her still-empty pussy.

And, as they did so, Zip was stunned to feel what felt like a splash of moisture, shooting right out of her tender nether lips, right onto his big hairy scrotum. Looking down, he stared, in awe.

"Holy shit," he said. "Did you just come?!"

Lifting her head up off the pillow, Denise gasped in shock. Then, she shook her head.

"No... no of course not!" she hissed.

But Zip knew what he was feeling - and, in addition to the incredibly tight clamping of her anus all around him, what he distinctly felt was her gooey pussy juices running down to the underside of his scrotum.

"Yes you did!" he laughed. "Just the feeling of getting my entire cock in your ass made you cum, didn't it?"

Mrs. Sablier's face quivered with emotion, but then she took a deep breath, and shook her luscious head from side to side.

"Just... just hurry up and wreck me, will you?" she asked him - her impatient anus giving another ferocious spasm all up and down his long hard cock.

Zip did not need to be told twice.

"You got it!" he said.

But her muscular ass, clenching down around him, was so tight that it was easier said than done. He pulled backwards - and gasped in shock, as he barely budged inside her. The walls of her anus quivered tight against him, seemingly going wild - and what little motion he did make was almost perfectly matched by her buxom hips swinging back along with him.