Intober 2023: Day 01 - Pegging

"Alright everyone, we're going to have a very special class today, and our friendly Hylian vai here is going to help me." Ashai rested her hand on Link's shoulder and squeezed him possessively with far more force than her students would be able to see.

If the voe had made one mistake... well, it was probably sneaking into Gerudo town in disguise as a vai. If he had made a second mistake, however, it was thinking that the woman who literally taught classes on voe wouldn't be able to recognize one. Sure, the disguise was good, and most Hylians were pretty hard to tell apart unless you really got them out of their clothes but she of all people he should have known better than to feel smarter than. He was definitely squirming slightly in her grip and under the eyes of her students. She didn't think he was going to try to run. He knew she had all the leverage. Run or disobey and get properly reported to the guards, put every Hylian under more scrutiny and be the one who ruined the whole black market of voe intruders that the town needed more than it let on. Better for him to play along and hope that she didn't intend to be the one who ruined things. She didn't. Fun didn't have to ruin things.

"Now, I understand that it can be hard to tell a Hylian voe from a vai when we see one," She felt him tense and she smiled a little, "Even my little friend here, she may look like a vai, but could you really be sure if you met her out in Hyrule? You could be letting the voe of your dreams slip right out from under your grasp."

"Ms. Ashai, does this mean we should approach every Hylian we see?" One of the students asked.

"Hmm? You're certainly allowed to, and there's no harm in pulling in the occasional vai. In fact, it happens quite often. While this isn't something helpful in the long term, there's no reason to simply throw them away. Remember, a vai in the hand is worth two voes in the bush."

"But Ms. Ashai, how do we... partner... with a vai?"

"Why, that's what this class is about, my most impatient of students." Ashai delivered it with a pause for the others in the class to titter at her expense, "After all, a Hylian vai could not handle partnering with one of us the way which we might partner with each other. Sure, many of them think they could, but it's not worth the risk of finding out the hard way that their eyes were bigger than their stomachs."

Ashai stepped behind her desk and pulled something out, she held it up for the class (and Link) to see. The girls made noises of mixed interest and embarrassment, Link made one of uneasy confusion.

"This, my students, is a strap." She ran her hand along it, "I made this one myself out of pieces of ore gifted to me by a Goron suitor. You may make yours out of seal tusk, polished stone, whatever strikes your fancy, just keep in mind that if you wouldn't put it inside yourself, you shouldn't try putting it in somebody else. Of course, if you do not wish to make one yourself, you can always purchase one from myself or one of the vendors in town who sells Hyrule exploration gear. Though they may not be as nice as the ones you end up making yourselves."

She set it on the table and let her words hang for a moment, letting Link look at it. She wasn't sure just how innocent he was, some of the older Gerudo talked about him and the princess like they'd merely been good friends, some talked like they had been lovers. Either way, she doubted that he'd ever been on the receiving end of something like this, even if his body looked all but built for it. He was more feminine, more appealingly proportioned, than just about any of the foreign voe she'd seen. But she'd also realized many years ago there was a good reason she wasn't ever going to be "Mrs. Ashai."

"Now, I would be willing to wager that most of your straps if not all of them will be smaller than this one, as an excessively large one is of benefit to nobody. However, even if you consider your strap to be quite small, this is another important component of things." She brought a jug of fruity-smelling oil from under her desk. "Like the strap, I make this myself, but you may get your own from wherever you please. I'm even willing to divulge my recipe for a price."

She uncorked the bottle and dunked the whole of the business end of the strap inside, then brought it out and pumped her hand up and down it a few times slowly. Link blushed under his veil and looked away.

"The first step is to properly and thoroughly lubricate the insertable portion. The comfort of the partner is everything, students. Unwelcome pain is the greatest foe of romance. Welcome pain... well..."

The class gave a lusty giggle, though it was more to do with her timing than anything. Ashai often got the impression that her students came in knowing nothing about the world, the other sex, or intimacy and walked out knowing nothing about the world and intimacy. This was a rare opportunity to teach a second subject.

"Now, with the insertable portion lubricated, you want to give the same treatment to where you intend to insert it."

Her hand found Link's shoulder again and hauled him over the side of her desk. She brought his pants down to uncover his ass and felt him freeze as he readied to be exposed to the class, but she kept the pants in place to hide his secret, only exposing the plump pale flesh of his ass. She spread it enough to expose the hole and drizzled a massive drop onto her target. She lubed her own finger next and then pushed it inside of him, feeling him freeze and tighten in an entirely different way. He was so warm and so tight on the inside, she couldn't help but wish she had the genuine article. Whoever got to pop his cherry for real was in for a treat, but she could at least take a first place victory by technicality.

"Now, you may question why I'm going to be using our vai's ass for demonstration. I would advise you generally to avoid this, however this is a unique case. As this vai is particularly more adept with this hole than her other, and with a strap of my size she's going to need all the help she can get." Ashai paused to let the class let out a mixed snicker and hiss, "As well, some vai even quite like it in the ass. Some voes as well, though I would discourage wasting their more reproductively useful fluids. I know for a fact that this one is going to quite enjoy being part of our little demonstration."

She slapped Link's ass gently with her free hand while she worked two and then three fingers inside of him, feeling his hole slowly relax and accept it. She wasn't treating him rough, aside from a few spanks here and there, so he was finding the adjustment easier than he might have otherwise. He was hardly the first voe she'd done this to, and they all learned to accept it. Some even came back for repeat showings. Ashai grabbed the strap and slipped it on.

"Now, you've likely noticed the shape of this one, and that's no accident. Because I knew that my partner would be receiving it anally, I picked out one which gives more pleasure to that particular hole," She gestured at it as she brought it to rest between Link's cheeks, "Notice how it's shaped. How the tip is relatively thin, then it blooms out like a turnip, then it gets narrower again before getting even wider than before. Sort of like a Gerudo's silhouette. Here's her head, her shoulders, her waist, and then the width of her hips at the bottom. With anal stimulation, pulling and pushing against the hole with things of varying sizes is extremely pleasurable. That's why you'll see ones which look like a forearm with a clenched fist, or even ones which look like gourds. But this one, I find, can't be beat. For voe, this wide part near the base pushes up against the prostate every time you thrust it inside, but even for vai the simple act of pulling the wide part out and pushing it back in can be quite exhilarating."

Ashai pressed the tip of her strap against Link's hole and started to ease her hips towards him. The tip was always an adventure, because it was nowhere near the broadest part of the strap, but it was about as broad as three of her fingers had been while being nowhere near as flexible. It felt almost oppressive, she had even heard "suffocating" before. She was inclined to believe it, though farther down was the part that made her assistants sing like birds.

When the tip finally broke in, Link started to voice his reaction but pressed a hand over his mouth, the other gripping at her desk desperately. His ass bloomed around it with probably more ease than he'd expected, but no voe expected his ass to actually receive her, at least until it was happening. As the wider part entered completely and his ass tightened around the narrowing middle of it, he didn't relax exactly, as she was pushing the great knob of the head further and further in him than he probably expected possible, but he did seem to shudder and almost sort of melt into it. Resting on his back, the tip had reached well past his navel, and he was feeling firsthand now that this extent wasn't as insurmountable as he probably thought. Though taking it was no mean feat, she'd half-expected looking at him that he'd take it like a champ. Some voe were simply built to be strapped.

"Notice how after the initial tension she's started to quite enjoy the process?" Ashai squeezed Link's cheeks firmly and moved her hips around, "With anal stimulation, the hardest part is often getting started. You are working against what the body is used to doing, so the recipient bares down, tries to resist what it feels is unnatural. But once it gets a taste of the pleasure you're giving it, it only gets easier and easier. Some recipients can take whole forearms, or even larger things, when trained enough."

She felt Link tense slightly at the mention and she slapped his ass playfully, suppressing a chuckle.

"If you wish to see something like that for yourself, I recommend finding your own strap partner. This one is going to be about at her limit when I get the bulky part of this into her."

Ashai started to really push deeper, bringing the widest part of the strap closer and closer to Link's ring. He could clearly feel himself being increasingly spread as she started to work further and further inside of him, the sensations unlike anything he was used to and seemingly only getting more intense with each passing second. She couldn't help but smile. If he thought this was a lot to take, he was in for a real surprise in a second.

She paused with the strap at its widest point, spreading him as much as she was going to today, and maybe ever. The intensity of it was clearly more than he was ready for, as his hand shot from his mouth to grip the other side of the table when she started to wiggle and churn her hips. He didn't even try to keep himself from panting and squeaking for the whole class to hear. He was lucky that the sounds were plenty girly enough that nobody would suspect a thing. Then, when she felt he might be starting to get a grip on things, she finished pushing in and let his ass close around the narrower base of the strap, wide bulb burrowing inside of him. The knotty base which she had slavishly designed, perfected, for crushing a voe's prostate bore down on him with full intensity. He squirmed beneath her as she leaned forward and let her weight rest on top of him, completely filled and completely covered. He was even going to smell like her when he waddled out of her classroom later.

"Isn't she something? How about we give my assistant a hand, class?" She asked sardonically.

The class gave a loose scattering of claps, though many were watching the display with what had turned into a voyeuristic leer. When she straightened back up and pulled the wide knot out, she glanced between her legs to see a wet dribbling stain of precum dripping down the front of the vai disguise. But that was only the opening act.

"Now, sometimes you want to go fast, sometimes you want to go slowly and hit all the right spots. It really depends on what you are doing, and I'm afraid you'll have to make your own choices in the heat of the moment. Remember, getting it wrong is not the end of the world. Mistakes are part of the process. In this case, I'm going to go slowly and focus on thrusting in a very specific way, but in my situation, you might choose to pound away with reckless abandon. You can't know which is right or which is wrong until you try, so always communicate with your partner."

Even as she lectured her class, Ashai was slowly working the wide bulb of the strap in of Link's ass and then out again. Each time it entered and crushed his prostate she would really twist her hips and make sure he was feeling it, each time it was back out she would tease him with it before pushing it back in, never letting him know for sure when he was about to take the great width of it again. He was showing impressive stamina in that he hadn't cum down the front of his pants and the side of her desk yet, but he would. It was only a matter of time. Time which she wasn't sure she really had if she wanted to get to the Noble Canteen while Furosa still had that pretty assistant of hers working the counter. She changed tactics.

"Alright, well, that about wraps up the lesson, what say we make this vai cum before I let you out?"

The class nodded and murmured a general assent and Ashai started to thrust more rapidly, dragging the knot in and out of Link's hole rapidly. He groaned and whined in discomfort, but the streaking stain down the front of his pants only continued to grow. She slapped his ass, pushed his head down into the desk, pulled his hair, tried just about everything that came to mind to see if something specific would make him pop. Nothing really worked, he seemed to genuinely just have quite good stamina. Probably something very useful for him, though when it came while being on the receiving end of a pretty vicious pegging, it probably did more hurt than good. The class were all looking at him, all expectant and more than a little eager to see him finally give in to his treatment.

He couldn't hold out forever. When his whole body tensed, Ashai pushed his face into the desk by a handful of his hair and pumped a few times with vicious speed before she felt his whole body relax and start jerking, wet white mess spilling down the front of his pants from his untouched cock which jerked and slapped against the desk, desperate for any sort of attention. She buried the strap in him to its hilt, squeezing his prostate as thoroughly as she could. His noises were even less dignified than before. She was pretty sure they were even girlier too.

When he had finally finished, Link lay stunned on the desk, the strap still buried inside of him. Ashai turned and gestured to the class and they all applauded him. His blush only got deeper.

"Now everyone, come thank our assistant for her help today. A kiss on the cheek or the forehead would be very appreciated, I'm sure. You know how nice it is to be treated softly after something rough."

Link was forced to lay on the desk, Ashai's hips and the strap which was still buried to its deepest inside of him the only thing concealing his identity, as one by one each of the students came to the front of the class and thanked him personally before leaning down to kiss him. When they had all finished and left the classroom, his face was so bright red that she was certain he was about to either burst or pass out. She slid the strap out of him and set it aside from cleaning. He remained where he was, ass still gaping open slightly and a great wet mess still coating the inside of his pants.

"Why don't you go lay down in my bath for a while?" She tousled his hair, "I might still decide to use you for my night class too."