Intober 2024: Day 21 - Pegging
Celebrities & Fan Fiction Story

Intober 2024: Day 21 - Pegging

by Revmh 17 min read 4.4 (3,500 views)
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"Welcome, friends, to the night class." Ashai addressed a smaller, more exclusive group of students than usual. "I know there have been some... rumblings... about night classes costing double what day classes do, but I assure you that tonight, I'm going to show you something that will make those prices seem like an absolute steal."

She had been a saleswoman before she'd been a teacher, but part of teaching was selling. At least when you charged for lessons. Night classes already did away with desks and chairs in favor of sitting around on a semicircle of cushions. The lights were lower and there were a few (emphasis on few) free snacks and drinks to be had. Most nights, what she had to sell was the exclusivity and the more personal touch. But tonight, she really did have something special. Her students grumbled.

"Now, I understand that, when I show you this, there are going to be some questions." Ashai raised her hands performatively, like she was surrendering. "Feel free to ask them, though one at a time, and you have to promise that tonight's lesson doesn't leave this room. That means no telling your friends, no telling the day students. Though I wouldn't mind the increased business, by any means, I certainly couldn't handle a sudden rush of students."

"Can you hurry up, teacher?" Torda grumbled. "I hate sitting criss-cross."

Ashai's brow wrinkled for a moment. If there was going to be one problem student for this special lesson, it was going to be Torda. Torda complained about how hard it was to pay for night lessons on a guard's salary and complained about how they didn't do enough to justify the increased price. Torda complained about how her bringing in vai for lessons was against the spirit of the rules even if it didn't break them. Torda just complained. Perhaps it was what she found fun.

"Well, you know how I like a bit of performance." Ashai hid her frustrations. "You're certainly welcome to sit at one of the desks instead, if you're so uncomfortable."

"The chairs are worse," Torda grumbled.

"Then you can certainly stand," Ashai fought the urge to add that Torda was also more than welcome to leave.

Torda didn't stand or move, simply sitting there and continuing to shift with a sour face. Ashai went on, picking up a little bell she had on her desk and ringing it. A moment later, a figure covered in a head-to-toe cloak came out from the back room slowly. Jingling coming from under the cloak suggesting a matching bell.

"Now, you know that I've had in vai for my demonstrations before," Ashai gave a meaningful look to Torda, "Which the guards have graciously allowed to continue. There was some dispute about the laws regarding my classes, which I quickly sorted out with the help of Captain Teake and a couple of legal records."

"Why would vai be a problem?" One of the other classmates asked. Ashai quietly thanked her for the chance to grandstand.

"Well, you see, it's not their gender which was the problem in this case." Ashai quickly wrote a few Gerudo symbols on the board. Ones which denoted property and livestock. "But, historically, when we first started allowing outsiders into town, it was under the pretext that they were protected and under the discretion of a Gerudo superior. Vai, in this case, were to be treated as almost... pets of the Gerudo superior. Where, with voe, they could be allowed in so long as they were clearly and visibly possessed by the Gerudo superior. For the Gerudo willing to apply for the proper licenses, she could possess vai temporarily similar to a sand seal, and a voe somewhat indefinitely."

A murmur passed through the students. The character which Ashai had not put up on the board, but which she put up a moment later, roughly translated to 'slave'. It was perhaps the single most detested word in the Gerudo language.

"What brought an end to this was that vai began to complain about this relationship. In fact, many Gerudo took this too far and started to offer what they called 'entry contracts'. They would allow a vai entry and boarding in exchange for a debt, which the vai would pay off while working within the town. However, between the cost of their living space and the interest, some vai wound up locked into contracts which they could never pay off. The vai successfully argued that they had been turned into slaves, despite Gerudo law strictly prohibiting it. So now, vai are allowed free entry to the town, though this does mean that we get the occasional voe sneaking in while wearing a disguise."

The second murmur was much more impassioned, and a lot of the students were looking over at the cloaked figure standing beside Ashai. She was leading them in the right direction, but she needed to lay a little more groundwork before she could do the reveal.

"So, when I host one of my classes featuring a demonstration vai, our fine guardswomen have to ensure several things. That the vai is not there against her will, that she is not under any sort of contract, all of these things are important to ensure that we avoid previously made mistakes. I was curious, however, to see how the laws had been updated in regard to voe."

She wrote another pair of words on the board. 'Prisoner' and 'punishment'. That got an extremely visceral chatter out of the students, one she had to quiet down by ringing the bell. The sound of the ring made her cloaked assistant jump a little.

"When re-writing the law, we could neither allow voe into the town like we did vai, nor could we bar them completely - since they might need to enter briefly to avoid storms or at the summons of the Chief. At the same time, as we were considering the adjacency of the contract vai to a slave, we had to consider the voe as well. So we did away with that entry law as well, though with some very interesting exceptions. For one, a voe who is properly married to a Gerudo may technically live within the walls of the town, though he is largely confined to the house. This makes living within Gerudo town unpopular, so most Gerudo with outsider husbands simply move away. One of the other exceptions would be a voe who has committed crimes within town disguised as a vai, or one who is a repeat offender when it comes to sneaking in. In these cases, imprisonment, execution, or punishment - including public display - are all allowable within the town's borders. So long as certain rules are followed."

Ashai stepped over to her cloaked assistant and ripped the cover away in a swift, practiced movement. The students all started talking at once, some of them shouting. Link, despite them practicing his uncloaking, still blushed red as a ruby from cheek to long, pointed ear. He folded his hands in front of his waist nervously, fidgeting and squirming. He was dressed in a thin, transparent veil around his face and a matching one around his midriff. In his mouth was a golden ring gag that exposed his wet red tongue and throat. The veil was held up by his earrings, and the body covering held up by a pair of golden fasteners clamped tight to his nipples meant to resemble piercings. His milky white skin was exposed, paler than most of the girls had probably seen in their lives. Smooth chest, thin shoulders, and taut arms all bare. The midriff covering stopped just below his waist, his pearly legs bare as well and his feet bare. Perhaps the most ostentatious and most eye-catching piece of ornamentation was on his crotch. Between his broad, almost feminine hips, his penis had been locked into a golden cage. From the end of it, where a little slit showed the fleshy pink of his head, a golden bell dangled.

"This isn't-!" Torda stood up. "You're-"

"Sit down!" Ashai rang the bell loudly again, and Link jumped a little again. "I'm going to explain to you exactly how and why what you're seeing is allowed."

Torda seemed like the only one willing to ruin the fun, but she was also the only guard in the room. She didn't sit down, but she at least backed away from the door while the others tittered excitedly. Ashai wiped the board and started to write a new set of words.

"One of the conditions, as I said, where this would be allowed, is if the voe is being punished. This voe has repeatedly broken into Gerudo town and-"

"He looks like one of the vai from your classes," One of the other students interjected. "The blonde girl."

"Purely a coincidence," Ashai blurted. "Blonde is not the most common Hylian hair color, but it's more common than you think."

"Yeah but... isn't that the same earring?" The student persisted.

"This earring marks coming of age in several Hylian villages." Ashai quickly lied. "I would hope that somebody who comes to both classes would remember that."

There was a bit of a snicker from the other girls and the student stopped persisting. That was a tool that, as a teacher, you always had but tried not to use. Saving it for when you really needed it, or when you really hated the student in question.

"Anyway-" Ashai continued writing, her ears twitching. Link kept fidgeting as the girls looked at him hungrily. "This voe has now, on several occasions, broken into Gerudo town while in vai disguise. Captain Teake will verify this, as she will verify that what I'm doing here follows all of the rules."

Ashai didn't mention the bribes. Things went better if you didn't mention the bribes. She was also counting at least somewhat on the fact that the easier something was to fact-check, the fewer people fact-checked it. Technically, most of what she was doing was legal. With a few minor nitpicks. She added a few more words to the board and then grabbed her ruler, pointing from the board to the associated item on Link.

"Firstly, the voe must be exposed in such a way that there is no ambiguity of his gender, but his... male organ... must also be contained in such a way as to make him incapable of impregnating any Gerudo." She gestured toward his cage. "There must be both a visual and auditory indicator of his imprisonment - a bell or a chime of some kind - and there must be no suitable desert footwear which might allow him to escape his punishment."

"What is the gag for?" One of the students asked.

"The gag is there because I like it," Ashai admitted.

"Wait, is his... thing... does it have to stay caged the whole time?" Another student asked.

"Yes, unfortunately it- Wait!" Ashai rang the bell loudly as several students got up at once. "I know your interest in a voe may begin and end with his breeding capabilities, but there are still many things you can learn about him like this!"

"What's the point of a voe if you can't fuck him?" Torda grumbled. Despite her loud wondering if any of this was legal, she was one of the first who had made for the door as soon as sex with Link was off the table.

"Well..." Ashai's ear twitched. To her, the appeal of the lessons was self-explanatory. But perhaps not everybody found it as fun as she did to watch a voe squirming in emasculated pleasure. "We can practice using insertables-"

"We already do that with the vai!" One of the students protested.

"But this time it will be a voe!" Ashai smiled, but she could tell she was losing them. "And in doing so, we'll be able to extract some of his sperm for... tasting and for... it's very good for your skin."

"I've heard that voe sperm tastes like honey," One of the students who had remained seated wondered aloud.

"Hmm, perhaps not honey, but it is very sweet, I assure you." Ashai pled. She had been feeding Link mostly sugary desert fruit the past week or so, it had better taste sweet.

"What good is knowing what a voe's sperm tastes like?" Torda - ever the complainer - scowled.

"Well, most voe want their wives to please them with their mouths. Some only occasionally, some very often. It can be quite important for voe to have a wife who performs proper oral stimulation." Ashai was maybe half lying, maybe a two-thirds lying. "It would be a tragic situation to get infatuated with the voe you think is your soul-mate, only for him to scorn you when you're intimidated by the taste of his sperm!"

A nervous murmur passed through the sitting students, and a more nervous but equally dubious one passed through the leavers. Eventually, though, they shuffled back to their seats.

"This will also not be a purely demonstrational class," Ashai tried to sweeten the pot as discontented murmurs kept scattering through the students. She grabbed one of the straps she had intended to use herself and quickly slipped it around Link's belly. Another insertable, one she had designed for specifically such a purpose, slotted into Link's gag when she lifted his veil and pushed it into place with a click. "I know some students are intimidated to practice 'riding' techniques with their teacher or fellow students, but with a voe..."

This, plainly, was not what she had told Link the class was going to entail. As she pushed him back onto the table and tied his wrists in place, he gave her an apprehensive look. But he had also signed up for these classes. Just like he'd signed up for day after day of her day classes. While it wasn't a 'come-what-may' agreement he was making with her, he was clearly still here instead of elsewhere because he wanted to be. As the students rose almost in unison and started to gather around the table, looking down at the restrained voe at hip height, Ashai could see his caged penis growing and making the cage snug.

"Alright, now, show of hands. How many riders will we have? Now how many penetrators?" She did a quick show of hands. All but one or two of the students were interested in riding. Life was a series of realizations that most people didn't find the same things fun that you did.

She grabbed one of her large, hydromelon-shaped bottles of lubricating oil and dipped one of the straps in it before handing it off to one of the penetrators. Then she drizzled the lubricant around the phallus-shaped strap around Link's navel and the banana-shaped object extending out from his mouth. Ashai did a quick tightness check on the student's strap. It was a long, beady obsidian rod like a meat skewer. From experience, she had found that the beads were just about the perfect size to press against Link's prostate, while the feeling of it going in and out reduced him to a whimpering mess very rapidly. The Gerudo slapped it wetly against his balls a few times.

"Oh no he doesn't like-" Ashai started, then stopped. "Most voe don't like that."

"Yeah, but...' The student looked at her strangely. "We're punishing him."

"Yes, but we're punishing him with the intent of extracting a sample." Ashai explained with annoyance. "Pain will make it difficult to deliver a sample."

"Difficult, but not impossible," The student's look grew stranger.

"Right," Ashai's ear twitched. "You can be rough, just... that... don't do that."

Watching for another few seconds, Ashai saw the student grinding the tip pretty firmly against Link's back door, putting his legs up onto her shoulders. As she did, the other students were disrobing. Torda seemed to push her way to the front of the line. She hopped up onto the table, her clothes sitting in a messy pile on one of the cushions. She had wide, slightly chubby hips but one of the most muscular builds Ashai had ever seen. A thick crop of turquoise pubes that matched her hair and a navel pierced with a single bright pearl, skin the same watermelon red as distant cliffs at sunset. Ashai's type, if not for the fact that she knew Torda well enough to know she was absolutely not Ashai's type.

Mounting Link's face, Torda pressed the long, thin member extending from his gag against her slit, wincing slightly as she sunk down on it until she reached the base. Link's nose pressed against her swollen pink clit between her blue-green pubes. His eyes seemed watery and distant. The first bead was already in his ass, and the student was pumping her hips without waiting for him to warm up and accept her. Torda grabbed two fistfuls of his hair and used his head as leverage as she started to raise and lower her hips.

"Torda, not so rough-" Ashai grimaced. "You... whatever your name is, go slower!"

One of the other students, a thickset Gerudo with a bit of a belly, clambered up onto the table and straddled the shorter, thicker strap around Link's stomach before dropping her backside down onto him with a noisy slap. Link gave a full-body spasm.

"Gentle! Gentle!" Ashai winced. "You're punishing him, not killing him!"

"Didn't you say he was a nasty pervert who kept sneaking into town?" The strap-wearing Gerudo sounded a little bored by how slow it was getting her rod into him.

"Yes, but-" Ashai was torn between trying to micromanage their play and trying to patch other holes. She grabbed a glass and handed it to the strap-wearer. "Hold this up to his cage, do not waste his cum."

Link could take it, was the thing. She wasn't worried about three slightly rowdy Gerudo breaking the hero exactly. But then, what was it she was worried about? Was she worried that they'd scare him off? That she'd lose out on her teacher's assistant, or her favorite toy? For as rough as she'd been with him, she'd never been callous. Perhaps she'd gone about this a bit wrong to begin with. Or maybe she just felt left out.

At the same time, his endurance impressed her. Right as she was worrying about the strap, his body seemed to relax enough to take it. She was worried about Torda's grip on him, but when the Gerudo lifted her hands to push her hair back, he started bobbing his head in time with her thrusts like he was trying to fuck her. Her juices were running down the toy and round the gag, covering his lips, leaking through the cracks. Link's cage looked like it was straining to contain a full erection, little bell jingling wildly in time with several different forces.

The heavyset Gerudo seemed to either finish or run out of stamina rather quickly, and as she dismounted another Gerudo was there to take her place. Assuming that nobody went back for seconds, it would still probably be a while before this all ended.

"Hey teacher," The strap-wearing Gerudo got her attention. "He's... cumming already?"

"What?" Ashai darted over in disbelief.

With a couple of jingling, bobbing motions, several sets of eyes watched Link's cage bounce up and down, leaking white from the slit in the tip down into the glass. Through every lesson they'd done, Link had never cum this fast, hell, he'd never cum in twice this amount of time. Maybe it was that so many things were going on, maybe it was one thing or the other, maybe it was the crowd and the realization of how powerless he was. Hell, maybe it was just that he liked it a bit rougher. Maybe he was fully ready to just lie back and be used by whatever may come. The mental image of him squirming, helpless, mind totally melted, was like an aphrodisiac to Ashai.

The strap-wearing Gerudo took the glass and drained it all.

"Wow, that is sweet!" She exclaimed, then saw the rest of them glaring at her.

"That was for the whole class," Ashai grumbled.

"Oh... oh shoot." The strap-wearer pulled out, leaving Link's hole gaping slightly, winking in the air as his legs remained up on her shoulders. She handed Ashai the glass and undid the buckles of the strap. "Sorry."

"That's fine," Ashai sighed. "He can go more than once. Let somebody else-"

"Voe can go more than once?" One of the waiting students asked in awe.

"Some of them-" Ashai started. "Well, when you stimulate their back doors, they can. That's why these lessons are so important."

An excited murmur passed around the students. One of them, who hadn't even been interested in using the strap before, stepped up and gestured toward it.

"I want my voe to be able to go all night!" She declared, likely far too ambitiously. "Is it as simple as using one of those on him after every time, to get him back into things?"

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