Pokemon Mystery Dungeon: Training Smeargle

Story by DarkWolf79 on SoFurry

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

#26 of Story Commissions

When a group of pokemon take a break while exploring a dungeon, they decide to use the newest member of the group for a little relief and entertainment. Hope he's up for it, cause these boys are eager to get started.

September 2020 Patreon Reward for Chobin


"Holy crap! How big is this place?"

"Relax, Toby," said Cress, the large Chesnaught pushing a curtain of ivy out of their path. "Lyre and I have been through here before. Should be a nice place to rest right about...ah-hah! Here we are."

Beyond the wall of vines was a beautiful cavern, sunlight spilling in from a large opening in the ceiling, looking out at the bright blue sky. A small waterfall spilled over the edge, splashing down into a pool that filled the back half of the cavern, the reflected sunlight dancing over the walls. It was the perfect place to stop and rest for a while.

"Wow," said Toby, his eyes following the light playing off the walls. "It's amazing! I've never seen anywhere like this."

The young Smeargle was still a rookie, new to being part of a rescue team. He wore a green bandana around his neck, the color a perfect match for the green tip of his paintbrush tail. An identical bandana was wrapped around the neck of his father, a Lucario named Ray.

"That's one of the most important things for a rescue team to know - how to navigate through places like this, and where all the hidden spots are," said Ray. "You never know when you might need a place to rest or make camp when you're on a mission."

The last member of their party stepped through the curtain of ivy, the vines swinging down behind him and blocking the cavern from view to any passersby in the tunnel outside. The red bandana around the Mienshao's right bicep was a match of the one worn by his teammate, Cress, though the Chesnaught's looked a lot smaller wrapped around his bulging biceps.

"And lucky for us, today's just about helping train you up," said Lyre to the young Smeargle. "Pokemon get lost in these caves all the time, especially youngsters like you who decide it would be fun to go exploring. But good news for you, Cress and I know these caves so well we could walk them blindfolded. By the time we're done, you'll know them almost as well as we do."

"But for now," said Cress, holding up the satchel containing their lunches, "Why don't we take a break and have something to eat. And I don't know about you, but after spending all morning hiking these caves, I wouldn't mind going for a swim," he added, eyeing the clear blue water.

After Cress passed around their packed lunches, the four pokemon sat on the floor of the cavern to eat, enjoying the sunlight shining down from the clear, warm day outside. The Chesnaught dipped his feet into the pool, and was soon joined by Toby, the cool water being surprisingly refreshing on the Smeargle's aching feet. He hadn't down this much walking all at once in a while, and it was nice to get some time to relax and get his energy back. They filled their canteens from the waterfall, before diving into the pool, swimming and splashing and taking some time to relax and enjoy themselves. The life of a rescue team could be hectic, but they weren't on duty today, and they were determined to enjoy it.

Though it soon became clear that some of them had very specific ideas about how they could enjoy their time together.

Toby was standing chest deep in the pool, enjoying the combination of the warm sunlight and cool, refreshing water when he felt someone swim up behind him and wrap their arms around his shoulders.

"This place is beautiful, isn't it?" said Ray, hugging his son to his chest.

"It really is," said Toby. "It's incredible."

Ray grinned. "And I know how we can make it even better."

Toby opened his mouth to ask him what him what he meant, but quickly closed it with a squeak when he felt the Lucario press his hips against his son's rear and start grinding his sheath against him. A sheath that the young Smeargle was intimately familiar with. A sheath that even now he could feel starting to swell as his father's cock started to emerge and rub against his furry backside.

"Daaaad," whined Toby. "Are we really going to do this here? Now?"

"You bet we are."

The blush that had been spreading over Toby's face went from a small flame to a raging fire as Lyre appeared in front of him. The long, purple-tipped white fur that normally hung from Lyre's wrists was floating around them in the water, the movements almost hypnotic as he took the Smeargle's hips in his hands and pushed his body up against the boy's, his larger purple-furred sheath and balls grinding against Toby's smaller, sandy-furred boy bits. Despite being a teen, Toby was still smaller than either Lyre or his father, especially considering both of the older men were fighting-types, naturally making them stronger and more muscular than the wiry-framed Smeargle.

"Come on, Toby, there's no need to be shy," said Lyre. "Besides, it's obvious how much you want this."

The Mienshao pressed a little harder against Toby, and almost against his will the young canine could feel his cock starting to slide from his sheath, growing into the water until he was fully erect, his pink dick pressed against Lyre's.

"That's a good boy," said Lyre. "Now let's have some fun."

Lyre wrapped one hand around both of their dicks, squeezing them together as he jerked them both off. Toby's moans were soon cut off as Ray turned his head and pulled him into a kiss, his hands teasing his son's nipples as he moaned into the Lucario's mouth. Lyre didn't try to interrupt the display of father/son bonding. Nice as it was to rub up against this little cutie, the Mienshao had always enjoyed watching something so taboo, and enjoyed egging them on. Of course, the two men sandwiching Toby between them didn't go unnoticed for long.

"Uh, what do you two think you're doing?"

Breaking the kiss, the two older males in the water turned to look at Cress, the Chesnaught sitting on the edge of the pool, eyeing the trio curiously. Toby couldn't bring himself to look at the Chesnaught, averting his eyes and blushing furiously.

"Why, we're just having some fun with my son," said Ray, grinding his cock against the boy's ass. "This sexy little body of his is just too hard to resist."

"And having to watch that cute rear of his all day without getting to touch it has been torture," added Lyre. He slid his other hand down, cupping Toby's balls and giving them a gentle squeeze, making him gasp and shudder. "But don't worry big guy, it's not like he's a virgin or anything."

"Well, not anymore," said Ray. "We saw to that."

"Yeah, we did!" said Lyre. He turned back to Cress. "Don't let this blushing, bashful face fool you though; Toby loves it when we play with him, even though he never wants to admit it right away. Put our little Smeargle here's quite the slutty little puppy, and he loves having his daddy fuck him. Don't you, Toby?"

Lyre did something under the water that Cress couldn't see, but apparently whatever it was felt very good, because it robbed Toby of his ability to speak, leaving the Smeargle able to answer only with moans and whimpers of pleasure.

"He sure does," said Ray, answering for his son, and enjoying the way the boy was rocking back and forth between the two men, trying and failing to deny the pleasure he was feeling from their attentions. "He's always a little hesitant at first, but once he gets a cock in him, oh man, you should hear the way he moans."

"Wait a minute," said Cress. "Lyre, is this why you kept trying to get us to team up together on jobs? And why you're always going over to Ray's place?"

"Hell yeah it is," said the Mienshao without no shame whatsoever. "What could be hotter and kinkier than watching a father fucking his son? And the mouth on him. He's a natural born cock-sucker."

"Not just his mouth," said Ray. "It's like his whole body was born to take cock. I don't think I've ever fucked an ass this good."

"Dad," whined Toby, having finally found his voice again. "Don't say things like that! It's embarrassing!"

"Embarrassing! What's embarrassing about having one of the hottest little bodies around?" asked the Lucario. "Trust me, Toby. I've had plenty of males squealing and squirming on my cock, but you're the best, hands down. And don't try to act like you don't like it, too. You take cock like it's what you were born to do."

"Ray, that might be a little much, don't you think?"

"Oh, Cress, you wouldn't be saying that if you'd had a go with him already," said Ray. "Toby may try to deny it, but he likes it when a big, strong male takes control and gives him a good, hard pounding, or stuffs that pretty mouth of his with a juicy cock."

"Oh, I've got a great idea!" exclaimed Lyre. "Cress, why don't you try him out for yourself? Then you'll see we're telling the truth."

"Are you kidding?" asked Cress.

"No, that's a great idea!" said Ray. "You think so, too, don't you Toby? He cupped his son's face turning him to look between the Chesnaught's legs at his rapidly swelling sheath. As perverted as the idea of fucking his friend's son was, it was hard to resist the offer of a blowjob, no matter the source. "You can show Cress there what a talented mouth you have, and he can help keep you quiet while I pound this tight little ass. What do you say, Cress? Would you like my boy to come over there and suck you off?"

Cress thought about it for a moment. While the sight of Ray basically molesting his son had been a bit of a surprise, Toby wasn't complaining, or even really trying to resist the two horny pokemon pressed up against him. And it had been a few days since he'd been with anyone.

"Oh, what the hell," said the Chesnaught. "I'm game for a little fun. How about you, Toby? You want to come over here and show me what has your old man bragging about you so much?"

Toby's face was blushing so hard his tan fur had turned a vivid pink. He couldn't believe he was in this situation, again. But, as much as he might have complained, there was no denying that he did enjoy it. It hadn't started out that way. At first, it was just going along with the sexual antics of his dad and his friend, more to make things easier for himself than because he really enjoyed it. But as time went by, and the encounters continued, Toby had grown to enjoy the attentions the older pokemon paid his body. He didn't like to admit it out loud, but it was the truth. Just like it was the truth that his eyes were now laser focused on Cress, the sight of the thick penis growing from the Chesnaught's sheath making him drool. As humiliating as it felt to give in, Toby finally nodded, unconsciously licking his lips at the thought of getting to taste the buff grass-type's cock.

Ray and Lyre quickly climbed out of the pool, pulling Toby with them. All three were fully erect, hard cocks bouncing and dripping water and precum as they shook the water from their fur and got the Smeargle into position. Lyre laid down on his back and pulled Toby down over him, the blushing Smeargle on all fours over the Mienshao, their stiff dicks rubbing against one another. They were soon joined by Ray and Cress, who was now fully hard and quite looking forward to getting some relief.

Cress knelt in front of Toby, taking his large cock in one hand and placing the other between the pup's ears. He tapped the head of his prick against the Smeargle's muzzle smearing his lips and even his nose with his pre, drowning Toby in his scent. Unable to resist any longer, Toby opened his mouth wide and sank down Cress' cock, the Chesnaught's hand guiding him along until he'd swallowed him to the root. His cock was almost as wide as Ray's knot, but Toby was able to take it, even if it did stretch his muzzle almost to the limit. Cress gasped as his cock pushed against the back of Toby's throat, the smaller canine only gagging slightly as he was held in place while his face was gently humped. He clearly had experience with sucking cock for him to be able take so much all at once without complaint.

"Oh fuck, you guys weren't kidding! You've got one hell of a mouth on you, kid," said Cress, looking down at Toby as he enjoyed the feeling of that warm little mouth suckling and swallowing around his aching penis. "Few sights better than a needy boy sucking your cock and staring up at you with those puppy dog eyes. Well, don't worry. After today, you can suck my cock whenever you want. And I'm going to want that to be as often as possible."

Toby's blush burned even hotter at the Chesnaught's words, his tan-furred cheeks bulging around the big male's heavily leaking cock, and he couldn't suppress a whimper at the knowledge that yet another of his father's friends wanted to use him for sex. Just like he couldn't stop his own painfully stiff erection from throbbing at the knowledge that he'd be going along with it, and would likely enjoy every minute of it. That big, meaty cock was delicious, and the thought of taking Cress under his tail made the Smeargle release a spurt of pre onto Lyre's belly and made his tailhole ache to be filled. A desire that was quickly fulfilled as Ray's cock thrust into him, the Lucario sinking slowly into his son's ass until his big, blue balls slapped against Toby's smaller, sandy colored sac.

"Oh, fuck yeah!" moaned Ray when he bottomed out inside his boy. A moan that was mirrored by Toby, though heavily muffled by the dick stuffing his mouth. He grabbed the Smeargle's tail a pulled it out of the way so he could enjoy the sight of his son's tailhole stretched around his cock, giving the furry length a few rougher, playful tugs. "Warm and welcoming, just like a needy boy-slut should be. And so tight! Even after all this time, you're still just as tight as the day I popped your cherry. You really do have a gift for taking cock, son. Now you be a good boy and suck that cock like you mean it while daddy has his fun."

Ray pulled back until just the head of his cock was still inside Toby, before thrusting forward, his hips slapping against the boy's cheeks as he set into a steady rhythm, his hands tightly gripping Toby's hips and pulling him back to meet his thrusts, letting the Lucario get his dick that little bit deeper into the hot, tight grip of his son's ass. The Lucario humping away at his backside had Toby rocking in place, which suited Cress just fine, who quickly fell into sync with Ray so that when his humping pushed Toby forward, Cress humped into his face, stuffing Toby full from both ends with every move. This also had the added bonus of grinding the boy's heavily leaking cock against Lyre's as he lay beneath the rutting males, thoroughly enjoying the sight of Toby getting his face fucked, grinning at the boy's warm precum on his belly and the almost hypnotic motion of the Chesnaught's big balls bouncing off the boy's chin.

And so it went, the horny poke-boy getting worked over by the trio of horny older males, moaning and whimpering at the taste of the cock on his tongue, the feeling of his father's dick pounding his ass, and the teasing touches of the Mienshao's penis against his own. Toby was soon lost to his lust, thrusting back to meet Ray's thrusts and pressing forward to bury his nose in Cress's crotch, desperate for more of the feelings that he could only get from being stuffed with as much cock as possible.

Cress and Ray certainly appreciated his efforts, the two of them getting even more forceful with their thrusts, and rather grabby with their hands. Ray bent over Toby's back, reaching below him and starting to jerk his son off, working his shaft with one hand and his knot with the other, making toby squeal in pleasure. Squeals that were quickly silenced by Cress when he grabbed the Smeargle's head in both hands, pushing Toby's head down as he thrust even harder. It wouldn't be a bit surprising if the boy's chin and nose were bruised after this from how hard his face was getting fucked.

And he wouldn't have it any other way.

Looking up at Cress, Ray could tell that the Chesnaught's orgasm wasn't far off. And as much as he'd enjoy pumping a hot load into his son, the look of blissful, sinful pleasure on the big guy's face gave him an idea.

"Hey, Cress. Instead of wasting your first load in his mouth, how about you finish up with this," said Ray, slapping Toby's ass playfully. "You can try out the best ass around, and give my boy here a preview of what he has to look forward to from now on."

Cress grinned. "Well, don't mind if I do."

Ray pulled out of Toby with a pop, and the Smeargle barely had time to register what was happening before he was pulled of the heavily leaking Chesnaught cock, leaving him gasping for breath. Without a word, Cress spun the boy around, wrapping his big hands around Toby's waist and lining himself up. Toby only had a moment to realize what was about to happen before it did, and Cress thrust his hips forward and pulled him back, hilting himself in the boy's tight ass in one go. Luckily for Toby, he'd gotten Cress slick enough (and Ray had stretched him out enough) that the entry was virtually painless, even if it didn't leave Toby speechless as all the air seemed to leave his lungs at once. After all he was taking a cock almost as thick as his father's knot, and coupled with the Chesnaught's length that didn't seem to leave room for much else inside him.

Toby's eyes rolled back in his head as Cress started to move, immediately hitting a rapid pace, the Smeargle's ass bouncing as it slapped against his hips. It was obvious the Chesnaught was so close to cumming, that he didn't care about dragging this out. He just wanted to empty his balls into his fluffy new toy. While Cress hammered away at the boy's backside, Ray and Lyre moved to stand in front of them, grabbing their cocks and quickly jerking off, enjoying the show.

The size of the knot pounding him meant that Toby's prostate was being pummeled with every thrust, and it quickly pushed him passed the point of no return, the Smeargle crying out as he came, splashing his impressive load over the cavern's stone floor.

The feeling of that tight ass squeezing him even tighter was the last straw, and Cress hilted himself under the pup's tail, roaring in triumph as he emptied his balls into the squirming Smeargle, enjoying how the younger male's body twitched every time his cock flexed and hosed down his prostate with another wave of hot spunk. And if the load leaking out of his ass hadn't been enough to cover Toby in the glorious stink of male on male sex, his father and Lyre painting his face with their loads certainly did, the two fighting types moving closer to make sure they got every drop of cum they could on the Smeargle's face until he was absolutely dripping in their seed.

Once all their orgasms had finally ended, Toby was left a shaking, cum covered, cum-filled mess, having been literally fucked senseless by the three on one assault. Not wanting to take his cock out of its hot, tight new home, Cress scoped Toby up, holding him flush with his hips as he waddled awkwardly back to the spring, all four of them settling in the water to clean up and enjoy their afterglows. After all, they'd need to rest up if they wanted to finish mapping the caves before nightfall.

And after nightfall, well, hopefully by then Toby would be ready for some more fun. Learning how to help other pokemon was part of his training, after all, and the three older pokemon were happy and eager to help teach him everything he needed to know.