Mommy Milkers

Story by Inja on SoFurry

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Royce, a nerdy guy is dragged by his folks on vacation where he thinks he won't have any fun. He is left to his own devices seeing as he is old enough now, but he makes friends with an older woman who gives him a vacation he won't soon forget. (Don't ask me why this story is called Mommy Milkers, it just sort of stuck because of Brienne and I can't think of a better name :P)


This is a work of fiction. Unless otherwise indicated, all the names, characters, businesses, places, events and incidents in this story are either the product of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are of legal and consenting age, likewise if you are reading this story, you should be of legal age in your respective country. All characters are my own creation, any resemblance to existing characters is purely coincidental and not intentional, please do not use them without permission. If you would like to use them in a story, please feel free to send me a PM. ********************************************************************************** Royce groaned as he flopped back onto his hotel bed, it was his last summer holiday before he went to university. All he wanted to do was relax and play video games, but his parents had thought some sun and sand would do him a world of good. So, the young scruffy brow furred wolf found himself alone in a hotel room in Hawaii. It wasn’t like he was a trouble child, his folks even admitted he was old enough to be left alone, but they for some reason didn’t think it was right to leave him back home in Iowa. Royce wasn’t the partying type, so he definitely wouldn’t have destroyed their house if left alone, at worst he might have organized a LAN party with a couple other of his geek friends. He was more into Magic the Gathering than he was chasing girls, which he knew probably disappointed his father…probably even his mother too. But he knew he was no ladies’ man, though he was tall, he was skinny. With his scruffy brown coat and pale brown eyes, he wasn’t much to look at and he knew it. It sure as shit didn’t help that he needed glasses to see as well, although thankfully in the last year his folks had finally sprung for contacts, so he didn’t look quite as dorky as he used to. “Go out, make friends, be normal!” his mom had encouraged before she and his father had left for a deep see diving tour that morning. They expected Royce to have fun, out in public and surrounded by strangers, it was like they didn’t know him at all! Royce hated talking to people he knew, let alone complete strangers. Plus, what kind of a loser went around trying to make friends in a hotel, especially at his age? At first, he tried to just pass the time watching television in his room, but the combination of lacklustre options and his guilt about ignoring his mother’s wishes soon began to eat at him. He knew he couldn’t lie to his parents, so he had no choice but to actually leave his hotel room and go outside, if even just for a little bit. That way, when they asked if he’d been anywhere, he could answer honestly and say yes. With some determination, Royce stuffed his towel, a bottle of water from the minifridge and a change of shorts into a small bag before heading down to the hotels indoor pool. He knew he looked like a tourist, wearing his oversized Green Lantern tee shirt and a pair of swim trunks that looked two sizes two big; Royce made his way down to the pool with his sandals clapping loudly with every step. He’d snuck in a graphic novel into his bag at the last moment, if push came to shove, he could at least just read it beside the pool to pass the time he supposed. Royce was surprised to see the pool area was relatively quiet, there thankfully weren’t many people around and the few that were there all seemed to have the same idea as he did. There were no young kids splashing around and screaming, there was only one person swimming, though he couldn’t quite make out who or what they were from a distance. The young wolf selected a spot that looked vacant, a row of four loungers set off to one side and were the furthest from the most occupied part of the indoor swimming pool area. On one of the loungers was a fluffy pink towel, a pair of sunglasses and a mobile phone, which indicated someone was using it. Royce didn’t mind however, they had set up on the left-hand side most lounger, so he took the furthest one from that and set himself up to lay down and begin reading his graphic novel. “Oh, hello there” a soft, and very definitely female voice said suddenly, as a shape moved in the background of Royce’s novel he was so focused on. When he looked up from his book, he was met by the sight of a very wet and very busty older bovine woman. She was clearly older than him, perhaps closer to his own mother’s age if he had to guess. She was curvy, perhaps maybe even a little bit chubby, but in a cute way. She had a little bit of a belly, thick thighs and a plump but very shapely butt too. He supposed some might call her voluptuous, but that would probably put her on the wrong side of what he thought was cute chubby. But most of all, Royce found it hard to tear his gaze away from her breasts, her big, heaving and very wet breasts…which were barely contained behind the world’s smallest bikini top. He marvelled at the engineering of her bikini; the straps must’ve been made of woven titanium to be that thin but still manage not to snap under the weight of the cow’s udders. “When you’re done staring, my eyes are up here” the cow teased with a little laugh as she saw the young wolf’s obvious gaze at her chest. She was obviously used to that sort of reaction and thankfully didn’t seem to be very upset by his staring at least. “Oh, shit…s…sorry!” Royce almost yelped and quickly snapped his eyes up to meet hers. He swore he was blushing so brightly that his cheeks might actually burst into flames they felt so hot. “It’s fine, I wouldn’t have the girls out in such a small top if I didn’t want people looking at them” she teased, giving a shimmy of her shoulders which just made those massive mounds shake hypnotically. The cow laughed again as Royce’s eyes immediately dropped back down, despite his best efforts not to. “I’m Brienne, by the way. Just so you have a name to go with the tits” the older woman offered with another teasing smile. “Roy…Royce” the young wolf stammered as he fought the urge to stare at Brienne’s tits again. He also had the sudden urge to rest his book over his lap, for no particular reason at all, especially not one he hoped Brienne wouldn’t notice. If she did notice however, she certainly knew better than to say as much. Instead, Brienne took it easy on the young man and just lay back on her lounger to rest a little. “Are you old enough to be out here on your own, Rolls Royce?” the bovine asked with only a hint of a tease this time. “Yeah, I turned eighteen a couple months ago. But my folks still dragged me out here despite that, last summer before I start college” the young wolf bemoaned his situation. It wasn’t lost on him just how easy Brienne seemed to be to talk to, especially for being an old and very attractive woman. Royce was normally prone to tripping over his own words whenever he tried talking to the opposite sex. “That sucks, but surely it’s not all bad?” Brienne asked as she rolled onto her side to face him, of course this caused a shifting of her bust again. Though either she didn’t notice it or just didn’t care as she once again gave the young wolf another look at her generous cleavage. “No…it’s definitely looking better” he replied with an almost squeaky voice. Royce couldn’t help but notice the strange smile the cow flashed when he said that though, for some reason he couldn’t help but feel like he was in danger. But that was ridiculous, he was the predator here, she was just a cow. What could she do to someone like him? “Where are your folks now?” Brienne asked in an off-hand sort of manner, as if she were just making polite conversation. If she were plotting to murder him, she was doing a damned good job of hiding it. “They’re out on a deep-sea fishing cruise, said they’d only be back around dinner time” Royce replied without thinking. “Oh my, it’s not even ten in the morning now, what ever will you do to pass the time?” Brienne said in a rather strange tone, one which made Royce’s crotch twitch and tingle for some weird reason. “Care to join me for a bit of a swim?” she offered with a nod of her head toward the pool. “Uh, sure…” Honestly, she could’ve asked him to help her rob a bank just then and he would have done it. Those goddamn tits of hers were downright hypnotic, he’d have opened a church and started a religion praising them if he weren’t so mesmerised and distracted by them. Before he knew it, Royce was treading water in the pool alongside the much older woman he had only just met. He hadn’t noticed it before, but now that they were so close, he saw just how beautiful her eyes were. Deep pools of emerald, framed by fiery red hair that was probably a bit curly when it was dry. He could also smell her suncream, a sweet almost fruity and coconutty scent that he found rather appealing. “Your folks wouldn’t mind you talking to me, would they?” Brienne asked as she slowly swam around and circled Royce in the deep end of the pool. He didn’t know why, but the way she was circling him brought to mind the image of a shark circling its prey before striking, which was ridiculous when he considered that she was a herbivore. “No, why would they? I’m an adult now” Royce said defensively and with a bit more conviction that he intended, which just made him blush as he realized he must sound like a kid trying to convince an adult they were an adult too. “That’s good to hear, I wouldn’t want to do anything inappropriate with you” Brienne almost purred into his ear. A strange sound considering she was not a species which typically did purr, but she also did it while pressing her barely covered bust up against him from behind. As expected of a young man such as Royce, his swim trunks did tent more than a little in response to the unexpected but very welcome physical contact. He of course was ever so glad the water would obscure such a sight, or at least he hoped it would. When she swam back around in front of him again, Royce couldn’t help but notice the strange way she was looking and smiling at him. “Why, what would you want to do with me” Royce asked nervously. Of course, he knew what he hoped she would want to do with him, as most hormone riddled young men such as himself would tend to think, but he doubted a beautiful older woman like Brienne would ever entertain such thoughts as that. Especially about someone of his species, that would fly in the face of nature itself, surely. “Oh, you know, nothing you wouldn’t want to do or wouldn’t enjoy, of course” the bovine said in a non-committal and very obtuse sort of way. Royce was quickly learning that Brienne had a strange way of speaking, she said a lot without saying anything at all. What she did say was also never very direct either, like she was saying one thing while meaning another, or perhaps she was meaning exactly what she was saying. Either way, Royce was quickly becoming confused and very flustered. Matters were only made worse by the way she kept accidentally brushing against him or touching him, her breasts were constantly brushing against his back and sides but never letting him get a direct touch. The same was true for his crotch, Brienne kept accidentally brushing or rubbing against his bulge with her behind or hip, but never outright groping him directly. It could all be explained away as simple and innocent accidents, but the way she looked and smiled at him, he was sure they weren’t. But Royce being Royce, he was too shy and too awkward to come right out and say as much. Eventually they decided they’d had enough of swimming for the moment, which the young wolf wasn’t sure if he was happy or sad about. On the one hand it meant she would finally stop teasing him the way she had been, on the other hand, it meant she would stop ‘accidentally’ brushing up against him with her tits and behind. His dick could only get so hard after all, if she made it any worse, the darn thing would likely explode. “Was that your stomach?” Brienne asked at the obvious sounds of hunger coming from the young man laying close beside her after they had returned to lounging beside the pool. The poor young wolf was still trying in vain to attempt to cover his bulge she had spent the last hour causing, but he only succeeded in making it that much more obvious. “Yeah, sorry” Royce mumbled in embarrassment as his stomach continued to gurgle and groan with growing urgency. He hadn’t expected to be down by the pool this long, or to be so active either, so Royce had forgone having a hearty breakfast and now his stomach was thanking him for it. “Tell you what, why don’t you join me for lunch? My treat!” Brienne offered with a cheery smile as she already started to collect her things in preparation to leave the pool area. “Uh, sure…if you really want to?” the young wolf asked with uncertainty. He had only just met this woman and now she was offering to buy him lunch? Something strange was going on, but between his hormones and now his hunger, his brain wasn’t even close to working at full capacity. He may as well be trying to understand Quantum physics just then with how little of the situation he was truly grasping. “Of course, it’s the least I could do. Follow me” the bovine said as she finished collecting her things and started heading for the exit. Royce scrambled to collect his items and follow close behind, though he knew he was not near as smooth as he would’ve liked to have been. If anything, he probably just looked like even more of a bumbling idiot as he fumbled and nearly dropped his book into the pool in his haste to gather his stuff. Once they were on the move, the young wolf was surprised to see she wasn’t leading him to the hotel’s restaurant, instead she was headed to the elevators. “Uhm, where are we going?” Royce eventually asked when he saw they’d gone up past his floor a few moments later. Then again, why would they go to his floor, or his room even. There was nothing of interest there for someone like Brienne, there was also no reason for her to even know which floor he was staying on anyway, so it would have been weird if not worrying if they had. “To my room, of course. Never had room service before?” the pretty cow asked with a friendly smile. Why would she be taking him up to her room? Surely they could get the same food down in the restaurant, where everyone else was probably still eating breakfast or possibly brunch. Royce frowned as he tried to figure out why she had decided to take him back to her room to get him some food instead. The young wolf followed close behind the older bovine, his brow furrowed in confusion. Even when she opened her hotel room door and let him inside, he didn’t see anything different from his room that would shed light on this being the choice of location for their brunch date. At most the room was a little more spacious, the bed was a little bigger too. The view was better, but if only just because it was higher up and could see out further across the beach and ocean far below. “The menu is on the bedside table, under the telephone” Brienne said as she walked past Royce and headed into the adjoining bathroom. “You can put your stuff down on the cuck chair” she called from the bathroom a moment later, once she was out of sight. “The what chair?” Royce frowned as he looked around, not sure what she had actually said. There wasn’t any other chair besides the single seater sitting in a corner of the room facing the bed, so he assumed she meant that and deposited his damp towel and graphic novel now stuffed into his bag onto the seat, then made his way over to the phone to have a look at the menu. Again, the menu was nothing fancy, it just had all the usual fare one would expect from a hotel restaurant. Royce didn’t see anything that would make coming up to Brienne’s room any better than going down to eat with everyone else, or perhaps she knew he was an introvert and hated crowds? Yeah, that must be it, she obviously just wanted to make him more comfortable while they shared a meal together. “See anything that makes your mouth water?” Brienne asked as she stepped out of her bathroom finally. “Not reallyohmigodyou’renaked!” Royce yelped as he slowly lifted his gaze from the menu in his hands to look at her, his eyes going wide the instant he spotted her. Brienne was standing in the middle of her room, wearing nothing but a bright smile. The young wolf didn’t know where to look, his eyes kept wanting to feast on the sight before him, but his natural shyness demanded he look away. Before him was a completely nude and very gorgeous older woman, her bare breasts now on full display. Those generous soft brown furred mounds capped with dark pink areola and stiff little nipples. It was something he had only ever seen on a computer screen until now, but it was so much better in person. Wait, she wasn’t wearing bikini bottoms either, he could see her…her…pussy too. Royce thought his eyes were about to pop out of his head they had gone so wide, but standing before him was the first real vagina he’d ever seen. He could see the pouting lips, perhaps a bit bigger than he was used to seeing in porn videos, not the neat little slit of professional porn stars. This was the cunt of a real woman, the sight and scent of it quickly filled his senses. His sensitive canine nose easily picked up that growing scent of something primal, no, he knew what it was, his entire body knew it. His cock was growing harder as a result, it was that feral instinct to breed, she was excited and his body knew it! “Yes, I am” Brienne laughed softly as she slowly walked a little closer to Royce, but when she saw how nervous he was, she stopped dead in her tracks. “We don’t have to do anything you don’t want to do” the bovine said with a reassuring pat to his upper arm. “We can also do everything you do want to do…if you want to do anything?” she also gently offered. “Uh huh” Was all the young wolf could say as he continued to look the nude older woman standing before him over from head to foot and back again. The front of his swim trunks were by now very obviously tented with his interest in what he saw. Seeing as he still seemed to shellshocked to do anything, Brienne reached out for Royce’s hands and guided them up to her breasts, letting the young wolf touch and squeeze at her mounds as he wished. “Wow…” he almost squeaked, which very clearly did not sound like something someone with experience would say. “Have you ever done anything with a woman before?” Brienne finally thought to ask, to which the young wolf simply shook his head as he stared down at his hands now holding the first pair of real tits he had ever touched in his life. Well, aside from his mother’s when he was a baby, at least she assumed Royce was breastfed as a pup. “Hmm, well then, in that case…how about I teach you everything you need to know about women?” the bovine offered with a genuine smile. “T…teach me?” Royce finally snapped out of his daze and looked up at her face. “Teach me what, exactly?” he asked, a strange sort of giddy eagerness starting to overtake him at the implications of such an offer. “Well, everything of course. From foreplay, to making love and everything in between” Brienne offered with a smile and shrug of her shoulders. “But first, let me help you relax a little…just sit here on the edge of my bed” she offered while gently guiding Royce over to sit on her bed where she had indicated. Royce jumped in surprise when his still wet swim trunks were unceremoniously yanked down before he was made to sit on the edge of the bed, suddenly finding himself as naked as Brienne was, save for his Green Lantern shirt. He watched the older woman with wide eyes as she smiled reassuringly down at him, before she guided his knees and then thighs apart in order to kneel between them. The raised brow wasn’t lost on him, but he just assumed it was because the bovine wasn’t used to dealing with canine anatomy. His breath caught in his throat when her hands reached out and touched him, or rather, she touched his sheath. He was already rather excited, which just resulted in a more plump than usual sheath, but Royce was not yet presenting that typical canine lipstick his kind was so well known for. It didn’t take much stroking and encouragement from Brienne to get his red lipstick to appear, however. Her hands were so soft, yet firm and direct, they felt almost magical. It really did feel better having someone else touching his junk compared to his own hands. It certainly didn’t hurt having a nice pare of tits to focus on as well behind the hands exploring his crotch for the first time too. “There it is” she cooed softly when she saw his flesh begin to peek free. “I’m going to kiss it now; this might be a bit intense for your first time but just relax and try enjoy it” the bovine said encouragingly. Royce watched with bated breath as she leaned forward slowly, until her head and muzzle blocked out the view of his crotch. Then he felt it, an almost electric sensation as soft lips wrapped about his flesh. It felt hot and slick, strangely soft but not at the same time, but it all felt good, almost too good in fact and quickly had him wanting to try buck his hips up against her lips, but her hands at his waist firmly held him down in place so he couldn’t. It also kept feeling better the more of his cock she sucked on, Brienne kept her head right where it was as the young canine’s length swelled and grew inside her muzzle. “Oh…oh God” Royce groaned and huffed, even whined a little as he shifted constantly. He couldn’t sit still, the pleasure was almost overwhelming as his sensitive prick was kissed, licked and sucked by the older woman who seemed to know exactly what she was doing. It was easily the most intense sensation he had ever felt in his life, it felt so damned good, but weirdly there was also a sense of needing to pee as well, which confused him. “I can’t…something…nngh!” he panted and groaned, something weird was happening in the pit of his stomach. He almost felt like he wanted to throw up, but not quite. His balls churned, maybe even felt like they were on fire. But his cock, it had never been so damned hard before, he swore it had grown two sizes too, the way it pulsed and throbbed between Brienne’s lips. “I need to…I need…” Royce whined and growled, he felt a rush of emotions and sensations all at once, his mind couldn’t process it all, there was just an immense growing pressure in his groin and then…white hot bliss. It felt similar to when he pleasured himself, but infinitely better and far more intense too. Royce’s vision briefly went white, though he didn’t know exactly for how long though. When his vision returned, he was staring up at the ceiling, he was now laid back on the bed with his hands gripping Brienne by the ears as his hips bucked up against her muzzle, his knot battering against her lips eagerly. He couldn’t stop himself, his body just kept on bucking and jerking, every move of her lips or tongue on his flesh made him jump and whine. After what felt like ages, Royce finally had the where withal to release his grasp on her ears, which then let the bovine slowly slip her muzzle off of his now spent and deflating cock. “So, I guess it’s safe to say you enjoyed your first ever blowjob?” Brienne asked with a smug little grin as she made a show of licking her lips. He hadn’t thought about it before, but she had had his cock fully inside her mouth when he came, so that meant that…she swallowed his load? God that was so damned hot… “Y…yeah…that was amazing!” Royce laughed between heavy pants as he tried to recover his breath. “Sorry about grabbing you by the ears though” he mumbled soon after. “It’s fine, I’ve had worse” she smiled and gave his thighs a gentle and reassuring pat. “If you think that was amazing, wait until you try fucking” Brienne teased suggestively. “Fucking…you mean, you and me, together…like…for real?” Royce suddenly sat up and stared at Brienne with look of disbelief. “Well, yeah, of course. But only if you want to…do you want to?” she asked, even though she pretty much already knew the answer. “Yes! Please!” the young wolf nodded his head eagerly and began to move, as if thinking they were about to do it right that instant. “Woah, slow down there, Romeo” the bovine laughed and gently pushed him back down onto the bed. “You need to recover first, even you young guys need at least a couple of minutes to reload before you can go again” Brienne pointed out as she poked his by now soft length as it retreated back into his sheath. “How long are you on holiday here for anyway, I forgot to ask earlier” she suddenly thought to ask. “Uh…we only landed yesterday, which was Sunday, so we leave the following Sunday…so a week?” Royce struggled to say, his mind was very clearly not firing on all cylinders at the moment, so even basic arithmetic was rather difficult at present. “Oh, same as me. Perfect, we’ll have plenty of time for your private lessons then” Brienne said with a broad grin. “Really?” Royce asked with optimism, suddenly this holiday was starting to look up! He thought he would be stuck doing nothing fun and being bored out of his mind, instead he would be getting the world’s best lessons by a total MILF! Or at least he assume she was a MILF, he didn’t actually know if she had kids or was even married for that matter. But surely, she wouldn’t be doing this sort of thing with him if she were married, would she? “Sure, if you want to of course” Brienne replied with a knowing grin and shrug of her shoulders as she pushed the young wolf to lay down properly on her bed before climbing up to lay beside him. “There’s no rush, we’ll get to do everything you’re probably thinking about in that pointy eared noggin of yours” she laughed as she could clearly see the gears working in the young man’s mind. “So, you mean, we could do…that again, what we just did?” he asked hopefully, his fluffy tail batting against the bed beside him. “Sure, if you want. But a gentleman should also return the favour” Brienne pointed out with a stern look. “You wouldn’t want your partner to feel used and unappreciated, would you?” she gently suggested and guided the young man in the ways of proper bedroom etiquette. “N…no, of course not!” Royce replied quickly and already began to move down toward her knees as if he had planned on doing so all along. “Not right now, I meant in the future!” the cow laughed as she grabbed Royce by the scruff and gently pulled him back up to lay beside her. “I mean, I will be teaching you how to eat pussy at some point, but not right now. I think today should be about getting you used to being touched and pleasured by someone else. That way you won’t be so…eager and rush things” the older women gently suggested as she lightly brushed a hand against his chest, slowly working her way down across his tummy and towards his once again twitching sheath. “Oh…oh, yeah. Makes sense…” he mumbled, though not entirely sure he understood. However it sure looked like his body did, Brienne noticed. His reload time was impressive, barely even a couple of minutes and already he was starting to poke free of his sheath again. This was really starting to look like a really promising encounter, she got to pop a cute young wolf’s cherry, as well as teach him how to properly fuck. Royce certainly did seem eager to learn, which was more than she could say for most guys her own age. “Just relax and enjoy the sensations, there’s no rush” she cooed softly to the young canine as she cuddled against his side, her head on his shoulder as her hand just lightly touched and teased along his swelling sheath again. This time she wasn’t actively trying to make him hard, she wasn’t even gripping and stroking at him. Brienne just let her fingers gently caress and dance along the length of Royce’s sheath, occasionally she would reach down to cup and lightly caress his balls. She always did enjoy watching a canine get hard, the way that pretty red length of theirs slowly slid free and swelled for her, until it was standing tall and bouncing a little with the beat of their heart. Royce seemed to be the sort that also shot little almost transparent jets of precum when he got really excited too. She felt it against her wrist when she lightly stroked a fingertip up along the underside of his cock, tracing that thick cumvein there until she was touching her fingertip to the tapered point of his dick in a lewd imitation of the famous “Creation of Adam” painting, only here it was her fingertip and a young wolf barely half her age’s cocktip doing the touching. “Try hold out as long as you can, okay?” Brienne softly asked of Royce, just as her fingers wrapped about his dick and she started to slowly stroke him. God, she loved how his dick felt in her hand, the way it throbbed and pulsed so eagerly. It was so rigid too, the sign of youth, that she could barely bend it with how strong his pulse was in that wonderful red length. She wondered if Royce knew how big he was too, he didn’t act like he knew he was sporting a decently above average cock, he seemed far too shy for that. It was no matter though, it just made this whole encounter so much better for her, a big dicked geek she got to teach and turn into her own personal fucktoy. “Fuck, getting close…” Royce whined after a few minutes, which was to be expected. It was longer than she had thought he would last though, not to toot her own horn or anything, but Brienne knew she gave excellent handjobs, so the young wolf actually did pretty well. She didn’t stop or slow down either, her skilled fingers just continued to stroke and pump the young man’s length, until finally he erupted. His load was impressive as well, especially considering she could still taste his first one on her tongue. Royce came with such ferocity that he painted his chest and belly with ease; some even spattered against the side of her tits pressed against his shoulder. But mostly the last few thick spurts coated her fingers as she gave him the last few strokes until he started to whine as the pleasure got too much. Seeing he was finished for now; Brienne just brought her fingers to her lips and licked her hand clean of his seed again. “S…sorry…” Royce eventually mumbled when he came back down to earth again, his ears laid flat against his messy hair and his cheeks glowing with another bright blush. “Sorry for what?” she asked curiously as she idly toyed with the mess on his belly and chest. “Cumming too quickly” the young wolf muttered, seeming rather embarrassed and ashamed about that fact. “Oh honey, that’s nothing to worry about. It’s perfectly normal, especially this early on in your life” Brienne laughed softly and leaned in to give Royce a little peck on his cheek. “Besides, I take it as a compliment” the bovine said honestly as she smiled at the young wolf. “You’re young, your hormones are raging and all this is still new to you. Your body doesn’t know how to properly process all of this information yet, so it will happen again” she continued, now moving to sit upright and cross-legged beside him. “Really?” Royce asked with a touch of uncertainty as he stared up at her for reassurance. “Yeah, I promise. Hell, I know some guys my age that still cum super early” she continued. “Nothing wrong with that either, but they also make up for it in other ways too” the cow began to explain. “As long as you look after your partners needs and not just your own, that’s what really matters in the long run.” “I guess…you mean like, returning the favour, right?” Royce asked hopefully. “Exactly! Now you’re getting it” Brienne smiled and ruffled his hair affectionately. “Speaking of, if you can get hard again…I’ll suck you off one more time before we order lunch?” she teased. “Deal!” Royce growled playfully as he immediately began to stroke at his once again deflating cock. To Brienne’s surprise, the young mutt did indeed get hard again surprisingly quickly. For a seeming nerd, the young wolf certainly had an impressive refractory period. But she was a woman of her word, not that she didn’t enjoy sucking cock either. This time however, she noticed that Royce lasted even longer than before. He also seemed to be more in control of himself as well, a bit less whining and squirming this time, along with a lot more eye contact. He seemed to be getting used to being touched and pleasured finally, which boded well for the rest of the week ahead. Lunch was strangely relaxing and almost cathartic in a way, for both Brienne and Royce. They had simply slipped into fluffy bathrobes when their lunches were delivered but stripped as soon as the door was closed. Being naked with each other just felt more natural and the more time they spent together as such, the more relaxed the young wolf seemed to get. Granted, he still checked her out whenever she bent over, but he wasn’t constantly staring at her tits now. Royce was getting used to the idea of having a naked woman around, at least to the extend he wasn’t staring constantly. His body certainly did keep reacting though, even after his second blowjob, the young canine was still sporting a delightfully plump sheath and some exposed lipstick. For his next round of training, Brienne had Royce lay back for her so she could straddle his lap. This time she just slowly and teasingly ground herself back and forth against his growing length. There was no penetration yet, but it was the first time the young wolf actually got to feel a woman’s pussy against his cock. He did surprisingly well there too, granted he didn’t last more than a minute or two, but considering his lack of experience, it was far longer than she would have guessed he would at any rate. This then led into his next lesson, his first real interaction with female genitalia. Brienne diligently and patiently guided Royce through the intricacies of her nether regions, explaining in detail all the different parts of her anatomy and then showing the young wolf how to touch, tease and pleasure all the different parts. She hadn’t initially planned on letting his tongue touch her there just yet, but he proved to be even more of a quick study than she had bargained for. It wasn’t very long before she had Royce’s face buried between her thighs and his tongue worming within the slick embrace of her cunt. God, she loved those long and broad canine tongues, they really were fantastic for eating cunt, she thought. Even better when the owner was so eager to do it too! Soon it even turned into a game of sorts, the more tricks she taught him and that he figured out for himself, the more they took turns in pleasuring each other orally. Before he knew it, the sun had set and it was almost time for dinner, which meant his parents would no doubt be looking for him soon. “We’ll have to continue this tomorrow…stud” Brienne groaned and shifted her hips as she reluctantly tried to pull his muzzle away from her groin. God, Royce was a pussy eating devil now, how the fuck had he gone from such a shy and nervous young pup to a cunt devouring demon in such a short period? He was even grinning up at her like a cat feasting on the finest cream, his muzzle was damp and matted with the evidence of just how much he had made the mature bovine cum her brains out. She had sucked enough seed out of him too that she didn’t think she needed dinner either, which considering his size was an impressive feat all on its own. “We need to get you showered and dressed…Roy…Royce! Are you even listening to meeeeohgodthattongue…” fuck, she’d created a monster. After considerable effort and self-control, Brienne finally got Royce to cease fire and actually climb into the shower with her. Not that it stopped him from groping and fondling every inch of her though, but it at least let her wash her scent off the young man before forcing him to get dressed again. The mature bovine all but had to physically kick the young wolf out of her room and slam her door shut behind him before he would leave, but finally, she was alone. God, she wished she could’ve let him stay longer, she would probably have had him balls deep up her cunt by now if she did though. But that would have to wait until tomorrow, she thought with a broad grin. ********************************************************************************** When his parents finally did return and went looking for him, they found Royce fast asleep and laying spread out on his hotel bed. They assumed he just had a very busy and exciting day, judging by how he merely snorted and grunted when they tried to wake him for dinner, along with the grin plastered to his muzzle. At least it looked and smelled as though he remembered to shower before he passed out, so that was something they supposed. “I wonder what he got up to today?” his mother pondered over dinner later that evening. They had left a note telling Royce to order some room service when he finally woke up and not to touch the mini fridge in his room, knowing how expensive they tended to be. “Considering how tired he was and that grin on his face, he probably found a group of nerds to play that stupid card game of his with” his father growled and stabbed at his seafood dinner angrily, sending a calamari ring rolling off his plate in the process. “I really wish he was having dinner with us, I know he would love eating some of this beef” his mother said wistfully as she gently prodded with a carrot on her fork at the thin cuts of beef, which had been cut in such a delicate manner to look like curtains. “That’s what he gets, nerds don’t get to enjoy the beef curtains” Royce’s dad grumbled again as he watched his wife toy with her food. “That’d look better with some cream in there” he offered with a slight grin that made his wife blush scarlet. When Royce finally awoke a couple hours later and found his parent’s note, he saw it was already well after eleven at night, which meant the kitchen was now closed. Even though his stomach was rumbling, the young wolf felt more content than he ever had before. Now more than ever, he looked forward to the rest of his time in Hawaii. It almost felt like a dream, but he could still feel Brienne’s lips wrapped about his flesh as well as recall the taste of her on his tongue. He briefly wondered what his father would say if he knew what Royce had been up to all day, or what he and his new friend planned on doing the rest of the week if they were left alone together. He knew his mother would blow a gasket and probably get Brienne thrown in jail, despite Royce being an adult now and perfectly capable of making his own choices. But being the typical mother she was, his mom would still treat him like her precious baby and try protecting him, even when he didn’t need protecting. Just the thoughts of Brienne that came unbidden were enough to bring a fresh stiffness to his groin, briefly he toyed with the idea of pleasuring himself so he could fall asleep again. But the new more naughty and adventurous side of him decided it would be best not to; he would rather save up for his next encounter with Brienne. After all, their next lesson was undoubtedly going to be more in depth, most notably his cock in deep between her thighs, or so he hoped. Surprisingly, sleep still came relatively easy and soon Royce was back in the land of slumber, only this time, his dreams were filled with soft brown furred mountains and pillowy hills he couldn’t help but want to grab and squeeze. ********************************************************************************** Royce was eager to head off and go find Brienne again, but his parents had other ideas. They felt bad for leaving him alone all day yesterday, as well as not getting a chance to at least have dinner with him. To make up for it, they made sure to wake Royce up and drag him downstairs to have breakfast with them, where they thought it would be fun for him to join them on an excursion to some local tourist attractions. “Sorry mom, I kinda have plans with…a friend” Royce said as he tried to weasel his way out of having to spend the entire day with his parents. After all, what horny young man would rather be stuck with his parents looking at nature when he could be upstairs in a hotel room getting his dick wet with a real MILF? “Why don’t you invite your friend to join us then, hmm?” his mom asked rather hopefully. “I don’t think she’s into that sort of thing” he replied too quickly and without really thinking. “She?” of course his mom had caught that. “Wait, you’re spending time with a girl…a real, legitimate girl?” His father asked in disbelief. “Yeah, a real girl dad” Royce sighed and rolled his eyes. “Do you think we could meet her?” his mother pressed in that typical motherly sort of way. Of course she would want to meet Brienne, just to see what sort of ‘girl’ her precious little boy was hanging out with. No doubt she thought he was being corrupted by some random harlot, which technically wasn’t far from the truth, but still, Royce did not want her meeting his mother…ever. That would be a surefire way of ending the fun little thing he and the gorgeous bovine had going. “No, I don’t think it would be a good idea” Royce replied nervously, trying not to panic. “Why not?” his mother continued to press. “Is she ugly, son?” His father asked with a grin, suspecting that the only girl his son could get with would be hideous. “What, no!” he almost shouted at his father. “She’s actually very attractive, I’ll have you know!” Royce said, perhaps a little too defensively. “Uh huh, she’s not a real person, is she. Probably some character in a videogame or something” his father scoffed again, thinking he’d uncovered his son’s secret. Royce almost argued against that, but he thankfully realized his father had just given him an out. “Y…yeah, you’re right dad” the young wolf sighed and slouched back in his seat. “She’s an AI character I started talking to in one of the stores here” he began to say, but when he noticed the look of pity in his mother’s eyes, he quickly changed tactics. “I know she’s not real, so nothing bad is going on. I just…like talking to her, I think it’s good practice for me to talk to real girls is all” he laid it on thick and smiled at his mother, who thankfully seemed to be buying it. “Alright dear, as long as there’s no harm in it, but the sooner you talk to real girls, all the better” she smiled softly and reached across the table to gently squeeze her son’s hand reassuringly. Royce almost sighed in relief, at least that had thrown his parents off Brienne’s scent, it also thankfully seemed to have gotten him out of having to join them on their excursion to all the tourist sites as well. A short while later, Royce was standing at the shuttle drop off and pickup area, waving goodbye to his folks as they headed out for their all-day trip. “Folks gone for the day?” a familiar voice said from somewhere behind him. Royce nearly leapt out of his skin as he whirled around and was met by a grinning Brienne. “How long have you been standing there?” he asked, his heart thumping in his chest. “Long enough to have heard your mother to tell you to behave while she’s gone, which of course you aren’t going to do” the beautiful bovine teased with a playful grin that already had the young wolf’s crotch twitching in eagerness. “Yeah, but whose fault is that, really?” Royce teased back with a grin of his own, thanks to his newfound confidence. “Still yours, young man” the mature bovine pointed out. “I merely offer the opportunity to misbehave; it’s still your choice to accept or not. It’s called accountability” Brienne rightly pointed out. “Are you a lawyer or something?” the exasperated teen asked, she had to be with how easily she had turned that around on him. “No, just put it down to experience…speaking of, I think there are a few more important things I need to teach you, outside the bedroom” Brienne quickly noted when she saw the young wolf perk up. The confused look on his face was priceless, almost cute in a way even. “Relax, we’ll still get to the fun stuff later, but you’ll thank me for this one day” she said somewhat cryptically. So it was that Royce found himself in a pharmacy being led around by Brienne. While it wasn’t what he’d hoped they would be doing together right now, he had to admit, it was definitely interesting and enlightening. Brienne explained that even though she’d had a hysterectomy many years ago and there was no worry of Royce accidentally impregnating her during their lessons, she thought it would still be a good idea to get him used to using condoms. To her line of thinking, she thought more guys should be in charge of bringing their own protection, she did not want Royce to be one of the ones that left it all up to the woman. She also guided him in finding the right size condoms as well, pointing out the differences in size and shape, especially for a canine like him. “Normal condoms will work for you, but they might slip off if you don’t get the canine specific ones that fit over your knot” she was busy explaining. “Especially if you get a little too rambunctious in bed, but still, they’re better than nothing” Brienne offered as she dropped a box of both kinds into the basket Royce was holding. Already it looked as though she planned on letting him try with normal condoms designed for a standard cylindrical penis, as well as the canine specific ones mean to fit over the knot. “Next, we should get some lube as well…” the bovine said more to herself as she tapped a finger to her chin in thought. “L…lube…as in…butt stuff?” Royce asked wide eyed, he had never even considered doing that with Brienne. Though the thought of it certainly did make him twitch in obvious and very eager ways. Brienne just stared at the young wolf in silence for a long moment, before she rolled her eyes and gave a drawn-out sigh. “Okay, fine…if you want, we can try that as well, I suppose. But I was actually wanting it to help with normal penetration…” the mature bovine began to explain. “When women get to my age, we don’t always get wet and wild at the drop of a hat, so sometimes we need some help making things move along more smoothly” she gently explained. “Huh, never thought about that” Royce nodded slowly as he listened and learned. To be fair, he didn’t actually know how old Brienne was, but that was one thing he did at least know about women. It was never polite to ask their age; his mother had drummed that into him from a young age. Brienne was exceptionally patient and understanding as she explained all the different aspects of sex to the young canine, from condoms to lubricants and even the fallacy that was aphrodisiacs. Royce understandably was rather crestfallen to learn that there was no such drug in existence that would turn a woman into a drooling and needy mess with only one thing on her mind. She even showed him a few of the small selection of toys the store had on offer, again pointing out that the fantasy of all women craving massive horse cocks was just nonsense. In reality, the vast majority of women physically couldn’t handle more than five or six inches, due to various physical and genetic makeups. The few that could handle such massive members were not the vast majority of women like porn would have him believe, even her being a bovine, that did not mean she could take on a horse either. By the time they had returned to Brienne’s hotel room, it was just about lunchtime again, though this time they did not need to order room service thanks to the various stops along their return trip to the hotel, where they tried some of the local cuisine. While they weren’t over full, they were both a little stuffed, but by Brienne’s reckoning, they’d burn it off easily enough. Royce’s next lesson involved putting on condoms, first the ‘standard’ type so he could get used to the rubber wrapped about his length. Brienne demonstrated what she meant about them not being ideal for canines due to their tendency to slip off, with her hand grasped firmly about the young wolf’s member, she began to stroke him slowly at first. But, the faster she started to go, the more he could feel the condom beginning to shift and slide, mostly because of how he produced so much precum and the natural smoothness of his cock, there wasn’t much in the way of friction for it to remain in place and soon enough, Brienne was left holding the empty semi-transparent pink condom in her hand, while Royce’s dick throbbed and bounced in disappointment. Of course, she wasn’t going to leave him hanging either, this time she used one of the canine specific condoms. It felt a bit weird having it squeeze down behind his knot, but when the bovine started stroking his shaft again, this time he noticed it barely shifted or moved. “See, much better, especially for enthusiastic young wolves” Brienne teased as she kept a brisk pace of stroking the young canine cock. “Don’t hold back, you need to see why you’re meant to pinch the tip of the condom” the bovine pointed out. This time Royce lasted a lot longer than before, mostly thanks to the added layer of rubber wrapped about his length, but also because Brienne had done an excellent job of getting him used to being touched and pleasured. “Fuck, cumming…” Royce closed his eyes and snarled as he gave a few last bucks into Brienne’s stroking hand. He swore he must’ve cum buckets with how hard his cock throbbed and his balls jumped, but when he looked down at the condom, there was barely more than a teaspoon or two of white mess trapped in the tip of the pale blue rubber. “Huh, thought there’d be more…” he panted and sounded almost defeated. “Wouldn’t make a difference, you could cum a gallon and it’d still be fine. That’s why guys saying the condoms are too small for them is bullshit” Brienne noted as she slipped the spent rubber off her student and tied it off, before tossing it in the trashcan beside her bed. “Alright, now this next part is the most important choice. This is where you would officially lose your virginity…are you absolutely certain you want to proceed?” the mature bovine asked with a direct stare at Royce, as if making sure he knew just how important a decision this was. “Yeah, of course I’m sure” he answered, though he apparently replied a little too eagerly for her liking. “No, Royce…really think about this. Use your head, not just your dick…you only get to lose it once, normally it should be with someone you care about, someone you love…” Brienne said more firmly, as she tried to drill home just how big a deal this choice was. “Look at me, I doubt I’ll find that anytime soon and besides, when will an opportunity like this ever come up again either?” He sighed and began to say. “I know what you mean, that it should be with a girlfriend or someone important, but I don’t have anyone like that in my life, hell…I don’t even have any prospects in that regard” the young wolf continued, now having reached out to take one of her hands and hold it tenderly. “So yes, I’m sure, I’m lucky enough to have someone that cares enough to teach me everything you have and make sure I’m a good lover, so that one day when I do have someone like that in my life, I won’t fuck it up” he finished with a smile. “Either way, still better than fucking a hooker, right?” he had to throw that last bit in, just to break the building tension. “Well, I suppose you’re right there…” Brienne laughed weakly and shook her head at Royce. “Alright then, lay back and let’s begin” she directed, waiting for the young wolf to get into position. She knew it wouldn’t take much to get him hard again, especially this time. Sure enough, with only a minimal of her grinding herself back and forth along his sheath had Royce back at full mast in mere moments. This time, Brienne pulled back and retrieved another canine condom to slip down over his length. With one last look down at her young student, she moved into position and slowly sank herself down onto his waiting shaft. “Oh…fuck…” Royce groaned and swallowed hard, it was better than he imagined. So hot, slick and surprisingly tight. This must be what she meant earlier that even her being a bovine didn’t mean she could take on a horse, hell, it felt like she could barely take him! “Fuck, you feel amazing” he panted out, resisting the urge to dig his nails into her thighs and just buck up into Brienne. “Well, aren’t you sweet, if you weren’t already balls deep in me, that would go a long way to getting you there in the first place” she teased with a little peck to his nose. “Just relax and get used to that feeling for a bit” she huffed and cooed softly to Royce. She had to admit, he did feel pretty good inside her too. She could feel how eagerly he was throbbing and pulsing within her, along with how his fingers were dimpling into the soft flesh of her hips with how tightly he was gripping her. “If you want to cum, just cum, we can go again…as many times as you want” Brienne offered with a calm and soothing tone as she smiled down at him. She knew he probably wouldn’t last long again like this, but that was fine. He had just officially lost his V card after all; he deserved to enjoy this moment to the fullest. Just to help him along a little, Brienne began to slowly but deliberately stir her hips down against his. She could feel Royce’s length begin to throb and pulse harder within her as he felt her clench, grip and squeeze down around him while she moved her hips. As she expected, the young wolf wouldn’t last very long inside his first pussy and soon she felt the familiar pulses of a cock trying to flood her womb with his seed. Not that she needed to worry though, even if he wasn’t wearing the condom, there was just too much else that did not align with them to make impregnation possible. “That was…amazing” Royce groaned softly, once he came down from his euphoric high. Brienne was still straddling his lap with his slowly deflating cock buried inside her. Now more than ever, he was sure he made the right choice. How many guys could honestly say their first time was this good, even though he hadn’t lasted long, he knew Brienne didn’t mind. She was more than happy to let him enjoy himself and go again later, when he was ready again. There was no pressure to perform, just to feel and learn from the experience. Now he knew what to expect, not that it would stop him cumming so soon again, but he would be better prepared on their next round. True to her word, Brienne let Royce go again, then again and again. Somehow, he managed to surprise her with just how often he was ready to go and soon they had even blown through both packs of condoms and now the young wolf was barebacking her doggystyle already. Royce had quickly gone from losing his virginity to fucking her like a pornstar in the span of a day and she couldn’t be happier. Brienne knew that he’d had a great first time, one that he would remember for the rest of his life. But that had quickly led to a great second, third and now…fuck, how many was this? She had lost count of just how many times the young man had managed to get hard again and fuck her. Especially seeing as he had seemingly drained his balls and the need to breed was all but gone, Royce was actually taking his time fucking her now. Brienne knew some guys her own age that didn’t know how to make her climax, but Royce had been a quick study and learned how after the first half dozen or so of his own. Now the sneaky shit was throwing in different angles, speeds, depths and putting together his own tricks to make her cum her brains out. He had learned very quickly what combination she enjoyed most and was not shy about using it on her either. Brienne stared up at the handsome young scruffy wolf as he folded her knees up by her tits, his hips clapping against the backs of her thighs and every thrust of his dick deep into her made her majestic mounds bounce from the impact. Frankly, even she was surprised she was still this flexible, but as sore as she knew she would be in the morning, Brienne knew it would be worth it. Another benefit of this position, aside from the feel of his hips against her thighs, Brienne was able to see the time as well, which was of vital importance in this instance. “Fuck me, I don’t want to tell you to stop…but you’re going to have to. Your folks will be getting back soon, can’t have you smelling like sex and bad decisions when you meet up with them” the bovine huffed and groaned. “You’re right, I’ll just have to fuck you twice as much tomorrow” Royce said with a grin down at her, which made Brienne raise her brows at the young man. Give a guy some pussy, and suddenly he has an abundance of confidence. It did look cute on him though, he still had that same dorky charm from when she had first met him, but now there was a layer of well-earned swagger behind it too. “Damn, get a little pussy and suddenly you’re Casanova…” she laughed and reached up to poke a finger against the wet pad of his nose. One last climax later and Royce finally relented in his efforts, he unfolded the busty cow and let her rest on the bed while he got dressed again, before saying his goodbyes and making a hasty retreat back down to his own hotel room. Meeting up with his parents in time would be the last bit of luck Royce would have for the next day or two, unfortunately. He had showered and changed, with only minutes to spare before they entered his room to collect their son for dinner. It seemed during their outing during the day, that his folks had major discussions about him, they both thought that it would be a waste for him to not see any of the sights while he was there. As such, he had no choice but to tag along with them the following morning, much to his disliking. At least he had exchanged numbers with Brienne the day before, so he was able to let her know about the change in plans, not that it helped him any. The cheeky bitch just sent him a snap of her cunt and said it was probably just as well; she needed to rest and recover after their time together yesterday. Brienne played a dangerous game with Royce the entire day too, knowing he was with his parents and was unable to sort himself out, it was the perfect opportunity to tease the unfortunate young man. She knew better than to include any details that could incriminate her, but that didn’t stop her from sending snaps of her naked body to him, but each image had a timer before it would automatically delete off his phone so there would be no evidence left behind in case his parents got hold of it. Wednesday was torture enough already, being stuck with his parents constantly in arms reach, so privacy was at an all time low. Brienne lapped it up as she teased him relentlessly, knowing he couldn’t do anything about it. Even when they got back to the hotel after dark, Royce was unable to escape as he was dragged off to dinner and a show. Admittedly it was a good dinner and an entertaining show, but even still, he would have much rather been balls deep in bovine. Thursday proved to be even worse, Royce was awoken before the sun was even up, just so they could go down to the beach for a special sunrise event. His only consolation was the fact that his parents actually let him have alcohol for the first time, a rather sweet and fruity drink that did warm him somewhat. Even he had to admit though, the sunrise over the ocean was spectacular, especially when the dolphins began to play and leap from the waves. Part of him felt guilty for not wanting to spend time with his parents and instead go have fun with Brienne, but the more immature side of him wanted nothing but to do just that. Royce finally began to realize this was the point where he was becoming an adult and he should probably start making better decisions, just how Brienne had forced him to before taking his virginity. Once he had accepted that, the rest of the day was easier to accept as he again joined his parents for another day of sight seeing and making memories with them before he went off to college. Of course, Brienne took it upon herself to tease him even worse than before. This time she included toys, specifically a thick red imitation canine one, which she stuffed under her tail and included the caption “This could be you, but you’re not here” and a tongue sticking out emoji. Strangely though, that image she didn’t set an expiration timer on. Of course, being the young horny wolf he was, Royce saved that image for later. Luckily, he did too, as by the time he and his parents returned to the hotel, it was close to midnight again. That lewd image served as the inspiration for two much needed releases before he was finally able to fall asleep. The following morning, Royce was up before his parents, though this time it was not in an effort to scamper off and head straight to Brienne’s room. Instead, he met them at their hotel room door before they all headed down to the restaurant to have breakfast together. He had expected to have a nice relaxing breakfast with his folks before finding Brienne and having some dirty fun later, but it turned out she had other ideas. Shortly after he and his parents had placed their meal order with the waitress, a familiar shape filled one of the seats behind his parents. When Royce looked up and spotted a grinning Brienne looking over his folk’s shoulders at him, the young wolf almost choked on his drink. Thankfully neither of his parents seemed to notice, though it wouldn’t the last time he would do so during the course of their meal. Nearly every time he looked up at her, Brienne was doing something that nearly made his eyes pop out of his head. She started off small at first, accidentally spilling something down her cleavage and then making a show of wiping it off suggestively while staring straight at him. Then she followed it up with a gratuitous simulation of performing oral on one of her vegan sausages, before she fit the entire thing into her mouth in one go. It was around that point that Royce was worried his erection might start tilting their table if he didn’t manage to wrangle it down one of his pants legs. It took everything in him not to groan or react outwardly from the bovine’s debaucherous displays, she damn near made it impossible for him to focus on the conversation with his parents. The final straw came when she finally finished her breakfast before Royce and his family, the young wolf watched as she turned and bent down to pick up her purse from the floor. She did it so fast and so subtly that it took a moment for it to register what he had just seen. Brienne was wearing a pretty, low cut green sundress, which showed off her ample cleavage. But it was short about the thighs as well, so when she turned and bent over, he got a good look up her skirt. Of course, the dirty bitch wasn’t wearing panties, and he got an eyeful of her pussy again, but that wasn’t what confused him. Under her tail was a round red disk of sorts, it looked shiny but soft. He frowned as he watched her walk a little awkwardly out of the restaurant and head back towards the elevators, and then it struck him. Royce’s eyes went wide and his cheeks turned a deep scarlet as he realized what he had seen, Brienne had been sitting there the entire time with that same canine toy inside her. What he had seen was simply the underside of the base of it nestled between her plush buttocks when she had bent over. Thankfully his parents had decided not to do anything too strenuous for the day, they were just going to spend some time on the beach or perhaps even just poolside, so that left Royce free to do as he wished. With growing nervous energy, he tried to remain composed, at least until his parents were finally out of sight. Once he was in the clear, Royce all but sprinted to Brienne’s hotel room door and gave three swift raps of his knuckles against her door. “Come in” Brienne called from inside her room invitingly, which the young wolf eagerly obliged and let himself into her hotel room. Brienne was still wearing that short green dress, but now she was laying on her bed on her tummy as she read a book. Though she didn’t say anything or even turn to look at him, Royce could tell by the slight grin on her lips that she was waiting for him to do something. The bovine was on her front, her chin resting in one hand while the other kept the book held open as she read from it. Down below, her legs were parted a little, just enough for him to get a peek up her dress if he wanted, but that wasn’t what he was here for and she knew it. When he climbed up onto the bed behind her and between her feet, Brienne didn’t move or say a word as he reached out and began to slowly push her dress up along her thighs and over the swell of her plush behind. Sure enough, just as he had seen earlier, there was that round red disk between her buttocks. Royce swallowed hard as he reached out and gently pressed against it, which got a soft huff and groan from Brienne. Still, she did not offer any direction or tell him to stop, she he simply grabbed the object and gave it a gentle tug. That made the bovine grunt as an inch or so of fake red length slipped free of her, but true to canine form, the knot was still trapped behind her snug little tail hole. If he really wanted to replace the toy with his own cock, he was going to have to remove it from Brienne, but thankfully she had already warned him to be gentle when it came to this particular act. So, like King Arthur pulling the sword from the stone, Royce slowly and carefully worked the toy back and out of her. Watching her ring resist and fight against the knot was strangely exciting, but ultimately her body would stretch and yield to his insistent tugging, with a lewd soft wet sound the knot finally popped free. The remainder of the toy was a lot easier to remove as well and soon he was holding the fake canine cock in his hand while staring at the small pink hole that looked way too small to take it. If he hadn’t been the one who just removed it, he would have a hard time believing Brienne’s dainty little asshole could take a cock that big. “Your turn” Brienne finally spoke as she panted softly, her face flushed with colour as she turned to smile back at him. “Just keep going slow, I don’t do this very often” she reminded him. Royce nodded in understanding; the last thing he wanted was to hurt Brienne. But she had told him that was impossible, no matter what he did, there would be at least some level of pain or at least discomfort in this act. The difference was, she was willing to endure it for him because she knew it would bring him pleasure, perhaps her too if he did it right. But for the first time, he was just to focus on his own pleasure and enjoy the sensations as not a lot of women would let someone as big as Royce under their tails. The young wolf made sure to use more lubrication on himself than was necessary, as well as reapplying Brienne’s as well, just for good measure. It was finally time; he was going to experience anal sex for real and with a gorgeous MILF to boot. Slowly he shuffled and crawled over her rump, letting her close her thighs together and between his knees to make it easier for them both. Her hands reached back to help guide him in too, one keeping her buttocks spread, while the other grasped and teased his tapered tip against her well-prepared tail hole. He let Brienne guide him in and followed her lead as he slowly sunk his prick past her pucker and into the incredibly tight hot depths of the bovine’s backside. “Fuck…feels better than the toy, that’s for damned sure” Brienne groaned out once Royce had managed to almost hilt her, only his knot remaining outside and poised between her buttocks. “So tight…and hot…feels amazing” he panted and growled softly, fighting the urge to begin thrusting and just fucking Brienne. She kept him in place for a moment as she adjusted to having him lodged in her guts, but after a while he was allowed to move, but only a little and very slowly too. As she had expected, Royce did not last very long again before he flooded her back passage with his hot white mess, though this time he took it in his stride that he didn’t last long, after all, he was getting to do something most men would kill for but never got the chance. Their second time was almost half an hour later, once Royce had sufficiently recovered. This time, he was the one laying down as Brienne rode him. She took the opportunity to show him how to play with her to make it even better, which he learned pretty quickly how to do and before she knew it, the damned dog had her cumming while she still had his prick up her ass. She had never really been able to cum like that before, usually the discomfort of something up her tail was enough to negate her own pleasure to the point she could at most only enjoy the sensations. But somehow, Royce had managed to make her pop, before he did again between her cheeks. That wasn’t the last miracle of the day either, by the fifth or sixth time she let the young wolf plough her behind, Brienne was surprised to find he even managed to make her cum just from anal penetration alone. She knew it was possible for some women to achieve orgasm that way, but she had never thought she would be one of them. Perhaps it was simply because she had never been that keen on anal before, or perhaps it was just because she had the wrong partner, but Royce seemed to prove her wrong and even managed to teach her something about herself in the process. ********************************************************************************** As much as he wished he could have spent all of Saturday with Brienne, especially being the last day before they both went their separate ways, luck was not on his side. Royce spent his morning and most of the early afternoon with his parents as they squeezed in one last activity. But they were merciful enough to give him a few hours alone before they were due to have dinner together. Of course, those few hours were spent between Brienne’s thighs, as well as beneath them and beneath her tail. It was almost like a grand tour of everything she had taught him, Royce was allowed to do as he wished with and to her. If it were a legitimate course worth a grade, he would have passed with distinctions and by the time he had given her a full display of practical application, the bovine was thoroughly satisfied and well-worn out. Unfortunately, that would be the last time Royce got to see Brienne before he was headed back home to Iowa, leaving the beautiful bovine nothing more than a fond memory. At least he could honestly say the trip to Hawaii had been one of the best in his life, he even got to make some wholesome memories with his parents before heading to college. A month and a bit later, Royce was finally on his own and heading to class when he bumped into a rather confused but friendly looking canine with curious brown spots who was clearly lost. “What’s the matter, big guy, lost?” Royce asked in a cheerful manner as he wandered over to the big mutt. “Yeah, I’m looking for Professor Tanner’s class…” he mumbled as he stared down at a printed-out map in his hands. “Oh, I see your problem…you’ve got it upside down” Royce laughed as he took the paper and turned it around. But when he saw the look of confusion only get worse, he sighed and shook his head. “Tell you what, my next class is pretty close to there, so why don’t I show you the way?” “Really? That’d be awesome, thanks!” the big brown spotted dog replied with a firm swat of appreciation to Royce’s should. He really was an odd fellow, the wolf though, but he seemed harmless and friendly at least. A short walk later and they were standing outside Professor Tanner’s classroom door. “Thanks for showing me the way, Rice!” the big dog said rather loudly. “It’s Royce, and you should know better than to be making so much noise in these hallways, Potato” a familiar voice said from behind him. Royce spun about and was met by a smiling Brienne, who looked very different wearing glasses and a long-sleeved fleece sweater. “Sorry, Professor Tanner, I won’t do it again” Potato mumbled as he slunk into the classroom with his tail between his legs. “I didn’t see your name on my call list” the bovine noted with a raised eyebrow at Royce. “Because I already graduated from your class, unless you offer a refresher?” he replied with a grin back at her. “Get to class, Royce, I’m sure I’ll see you around…and for God sakes Potato, stop sniffing the board markers!” she snapped as soon as she spotted the big mutt standing at the front of her class holding on of her coloured markers.