Simba's First Time

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#4 of Story Commissions

After following Timon when the meerkat sneaks off for some early morning fun with a new friend, Simba is introduced to all the fun things horny males can do with one another.

Commission for an anonymous sponsor.


"Where's he sneaking off to?"

Simba raised his head as he watched Timon disappear through a bush and into the jungle. It had been a little over a month now since he'd started living with Timon and Pumbaa after the pair found him in the desert. So far, he'd really been enjoying his new life here, even if the food had taken some getting used to.

But lately, he'd noticed that Timon would disappear for a while every morning while he thought the other two were still sleeping, and would either return before they woke up, or if they already had, he always made sure to bring back some breakfast for them to share. Simba would probably never have caught on if he hadn't seen Timon return one morning and, thinking he and Pumbaa were still asleep, pretend to go back to sleep until the others started waking up. Timon was definitely hiding something - Simba had tried to get away with enough things in his life that he could recognize when his friends were trying to keep things from him. Maybe it had something to do with the other thing the young lion had noticed. For the last few days, every time Timon had snuck off to ... wherever it was he was going, he'd had to move even more carefully to avoid waking up Simba or Pumbaa thanks to the hard length of meerkat meat swinging between his legs. But every time he came back, the smaller male's penis was nowhere in sight.

That was the reason that Simba had decided to follow Timon to see where he was going and what he was up to. Simba had gotten hard before, of course, but he had no idea how to make it go back down other than just waiting for it to stop. It was especially annoying when he got hard now, forcing him to hide from his new friends until his penis retreated back into his sheath. If Timon knew of some way to get rid of his erections faster, maybe he'd be willing to tell him what to do. Neither Timon nor Pumbaa had had any problems answering any of his other questions since he joined up with them, so even though it might be an awkward conversation, Simba was hopeful that the meerkat would still be willing to help him.

Careful not to wake up Pumbaa, Simba climbed to his feet, shaking himself off and stretching before following Timon. The meerkat had enough of a head start that Simba couldn't see where he went, but he didn't need to - Timon's arousal had made his scent even stronger, and the lion cub had no trouble following even though he still wasn't totally familiar with the area yet. Timon's scent got stronger as Simba caught up with him. Not wanting to startle his friend, Simba slowly pushed a large leaf out of the way and, careful to stay hidden, he peered out into a small clearing. What he saw made his jaw drop. He wasn't alone.

A large black cat was lounging back against a tree, his hindlegs spread wide and his long black tail lashing back and forth leisurely across the ground. Simba hadn't seen another feline since leaving the Pridelands, but he could tell the other cat was definitely male - if his deep voiced moans of pleasure weren't enough to give him away, the long pink penis sticking up between his legs certainly was. Though it was hard to get a good look at the big cat's full erection, mostly because about half of it was currently stuffed in Timon's mouth. The meerkat stood between the black cat's legs, his feet on either side of his tail, his mouth sucking and slurping at the bigger male's cock, his hands fondling the velvety black sac hanging below it while his hips humped back and forth.

In his surprise, Simba obviously wasn't being as careful about staying hidden as he should have been, because even through his lust-filled haze, the other cat quickly spotted him, chuckling softly to himself.

"Well, hello there young one," said the cat in a smooth rich voice. He glanced down at the meerkat currently occupied between his legs. "Friend of yours, Timon?"

Ears perking up in surprise at the big cat's words, Timon pulled himself off the other male's cock with a slick pop, gasping for air as he turned to see who the cat was talking about. As he turned, his cock slid out of the big cat's tailhole. When he spotted Simba, Timon's whole body went stiff for a moment as he quickly tried to figure out what to do. Realizing that there was no way the young lion could have missed what he was doing, he decided that there wasn't much point in trying to explain away what he'd been up to. Shrugging to himself, Timon just fell back on his usual carefree attitude, and he'd just see where it took them.

"Good morning, Simba. Didn't think you'd be up this early."

"Morning," said Simba, reflexively. "Timon, what were you doing just now?"

"Oh, that?" said Timon, turning to face Simba properly and giving the lion cub a good look at his own dripping erection. "Just having some fun. Oh, introductions! Simba, this is Bagheera. Bagheera, Simba."

"Charmed," replied Bagheera, bowing his head to the young lion.

"Nice to meet you," said Simba. He may not be in the Pridelands anymore, but the other male was obviously bigger and stronger than him and being polite certainly couldn't hurt. "So, is that how you've been doing it?"

"Doing what?" asked Timon.

"Making your penis get soft again. But, wait ... that can't be right. If what you were doing makes you go soft, then why are you still hard now?" asked Simba, gesturing with a paw to the pink erection between Timon's legs.

Both Timon and Simba jumped slightly as Bagheera started laughing.

"Not exactly," said Bagheera. "What you saw Timon doing is called a blowjob. It's when you lick or suck a male's penis, and it feels very good for them. Timon was helping me get rid of my own erection, and then I was going to help him get rid of his." Thinking for a moment, Bagheera added, "Do you know about mating?"

"Um, a little bit," said Simba. He'd spotted his parents in the act a couple of times but didn't really know all the details. "I know that when a male and a female mate, that's how they have cubs."

"That's right," said Bagheera. "But did you know that males can mate with each other as well?"

"Whoa, really!?"

"You bet'cha," said Timon. "And the best part is, when it's just us guys you get to have all the fun of sex without having to worry about having cubs later."

"Sex?"

"That's another word for mating," said Bagheera.

"That sounds like a lot of fun," said Simba. "Can you show me how?"

Timon and Bagheera looked at each other for a moment, before turning back to Simba.

"Are you sure about this?" asked Timon.

"I'm sure," said Simba, stepping out into the clearing and revealing his own erection hanging below him. "Watching you guys do that made me hard, and if there's a way to make it go away that feels good, I want to learn how to do it."

At Simba's words, Timon's cock throbbed and a line of precum shot out onto the grass. Taking a breath to get himself under control, Timon said, "Alright then, kid, we'll show you how it's done. First thing I need you to do is come over here and lay down on your back."

Simba hurried to do as he was told, trotting over and flopping down on his back, his stiff penis resting against the soft fur of his belly. Timon walked over to straddle the cub's tail, just like he'd been doing to Bagheera.

"Alright, kid, let me walk you through how all this works," said Timon. "When males want to have sex with other males, there are a few different things they can do, but there are two that I really prefer. You already saw me and Bagheera there doing the first one - it's called a blowjob." As he spoke, Timon took the lion cub's sac in his paws, gently rolling them around and enjoying the soft golden fur covering them. He then moved one paw up and began stroking Simba's cock, making the cub squirm a little at the good feelings coming from the meerkat's touches. "It's when you lick a male's dick or put it in your mouth and suck on it. A male's cock is very sensitive, and when something feels good, doing it to their cock can make it feel even better."

"Dick? Cock? What does that mean?" asked Simba.

"Just other words for penis," said Bagheera. "Our friend here has quite the mouth on him." He chuckled. "In more ways than one."

"Haven't heard any complaints from you about it before," said Timon. "Well anyway, I'll let you get a feel of what Bagheera was enjoying later, Simba. Right now, I'm going to show you the best way for two males to have sex."

"And how do we do that?" asked Simba.

"Well, I don't know if you noticed, but that was actually the other thing I was doing with Bagheera when you got here. When two males have sex, one of them puts his penis inside the other," said Timon.

"You want to put your ... dick, inside me?" asked Simba, stumbling slightly at using one of the new words. "How?"

"I'm glad you asked," said Timon, raising a paw to his mouth and slicking up two of his fingers. "I'll put it in here." He put his spit-slick fingers against the cubs tailhole, and pushed firmly and smoothly, the difference in their sizes letting Timon's fingers easily slip inside the cub's virgin tailhole.

"Timon, that feels weird."

"Weird in a bad way?" asked Timon, grinning, "Or weird but you kind of like it?"

Simba squirmed as Timon's fingers sank deeper into his rear. It was a strange feeling, but not an altogether bad one. "I think ... I think I like it."

"I thought you would." Timon pulled his fingers out and stepped forward lining up the tip of his dick with Simba's tailhole. "So I think you'll like this, too."

Timon slowly pressed forward, gradually increasing the pressure as he worked the head of his dick against Simba's pucker. After a minute or two, he managed to push through the cub's resistance, slowly sinking his dick inside the lion until he was hilted under the cub's tail. When his balls were resting against the base of the lion's tail, a shudder ran through Timon's body as he looked up at Simba, seeing the predator laid out in front of him. Having not gotten any complaints from Simba about what he was doing, Timon pulled back and started into a steady motion, humping in and out of Simba's tailhole, grabbing just below Simba's hind paws and holding his legs up and spread, giving the meerkat a tantalizing view of the cub's bits resting against his stomach, and his own shaft sinking into that gold-furred rump.

Having Timon's dick inside him was definitely a strange feeling for Simba, but it was far from a bad one. Even though it was his first time, the difference in their sizes meant that he'd been able to take the meerkat's full length without any real difficulty. Simba had been a little worried when Timon had started, but as the meerkat started humping into him at a steady pace, Simba found that he actually really liked the feelings that were spreading out from his rear. For his part, Timon certainly seemed to be enjoying himself, moaning and mumbling incoherently to himself, practically drooling over Simba as he fucked him.

"You'll have to forgive Timon," said Bagheera. "Our little friend has a bit of a thing for having sex with males that are bigger than him. The size difference really gets him going. Not that I can blame him."

"Why's that?" asked Simba.

"Well, Timon has a thing for males that are bigger than he is. I, on the other paw, enjoy having sex with males that are smaller than me. In fact, I was wondering if maybe you'd be interested in having some fun with me."

Simba thought about Bagheera's offer for a minute. "Sure, that sounds like fun. As soon as Timon is done, we can -"

"Oh, we don't need to wait," said Bagheera, climbing to his feet. He moved to stand over Simba, squatting down to bring his own stiff erection close to Simba's face. The black cat's low hanging balls were resting against Simba's chest, with the cub only able to see the bigger male's cock, sac, belly, and hindlegs. "We can get started right now if you'd be willing to try what Timon was doing when you arrived."

Simba's eyes were drawn to the panther's stiff length as Bagheera tensed the muscles in his groin, making his cock bounce up and down in front of Simba's muzzle, the sight and smell of the big cat's dick and balls becoming his whole world.

"Go on, Simba," said Bagheera, moving his cock forward until it bumped against his nose, smearing his face with pre. "I'm sure you'll like it once you give it a try."

Bending his head forward, found that far from being unpleasant, he rather liked the scent of the other male's cock. Unsure of exactly how to start, and since Bagheera hadn't really given him any instructions about what exactly he should do, Simba just did what came naturally. He gave the tip of Bagheera's cock a tentative lick, not really knowing what to expect. To his surprise, the other male tasted really good, and Simba began licking over his length in earnest, drawing happy moans of pleasure from Bagheera. The feeling of the cub's rough little tongue swiping over his barbs was driving the big cat wild. After of few minutes of Simba giving his dick a thorough licking, Bagheera spoke up.

"That's very good, Simba. It's been far too long since I've had another cat lick me. But why don't we try something even better?" The big cat reached down and wrapped a paw around the back of Simba's head. "Do you trust me?"

"Yeah, I trust you, Bagheera," said Simba.

"So then instead of licking my cock, why don't you try sucking it like Timon was doing before? I'll help you out with getting a feel for it since it's your first time. Just please be careful with your teeth. I'm sure you understand that bites and scrapes down there can really hurt."

Pulling the cub's head forward, Bagheera slipped his dick into Simba's muzzle. He pulled Simba down until the tip of his cock poked at the back of the lion's throat, making him gag. Bagheera pulled back slightly, giving Simba room to breathe and get used to having a cock in his mouth without taking much of it out of that warm, wet muzzle. It didn't take long for Simba to get used to the new feelings, and he tried to speak around the big cock stuffing his mouth, but Bagheera got the message. He started pushing Simba down further, sliding his cock into the cub's throat, not stopping until Simba's lips were kissing the base of the panther's cock.

Simba struggled and squirmed at first, trying his best to ignore his gag reflex and breathe around the thick length in his mouth while Bagheera coached him through it. Eventually Simba started bobbing his head up and down Bagheera's length, his rough tongue running along the underside of the bigger male's shaft. Meanwhile, Bagheera was enjoying the feelings that sweet little cub-muzzle was bringing him, moaning and offering words of encouragement. The panther was already leaking precum pretty heavily, and fired off even stronger shots to wash Simba's tongue in his musk every time he looked down and met Simba's gaze, the cub's cheeks bulging around the black cat's penis. Despite his lack of experience with sucking cock, Simba's youthful enthusiasm was making up for any lack of technique, and he was quickly pushing Bagheera to the edge.

Though not as quickly as Timon. The sight of Bagheera pumping his dick into the young lion's muzzle combined with the feeling of stuffing his own length under Simba's tail was too much for the meerkat to handle, and he came, burying himself as deep into Simba's ass as he could while he pumped shot after shot of cum inside the young predator.

The strange feeling of Timon's cock jerking inside him and the warmth spreading through his insides was enough to make Simba pause his blowjob, pulling back off Bagheera's member as he gasped at the feeling. Once his orgasm had run its course, Timon pulled out, falling back onto his rump and watching the small trickle of cum spilling out of Simba's tailhole.

"Well, Simba," said Bagheera, moving so he was no longer standing over the cub. "Did you enjoy your first time being mounted by another male?"

"Yeah, I did. It felt kind of weird at first, but I really liked it!" said Simba, grinning. "Bagheera, don't you want me to finish sucking you?"

"Actually, I was thinking we could try something else," said Bagheera. "Now that you've seen what it's like getting fucked by someone smaller, how would you like to try getting fucked by someone bigger than you?"

Simba gulped nervously as his eyes flicked down to stare at the throbbing length between the panther's legs. Sure, he may have just had it in his mouth, but the thought of having that meaty length going into his tailhole made it seem even larger than it was. Still, Simba couldn't deny that the panther was very attractive, and he couldn't help but wonder what it would be like to let the bigger cat mount him. He'd certainly enjoyed having Timon's dick inside him - the slight fullness he'd felt had been really nice, and Bagheera's much bigger penis promised to stretch him open even more.

"Okay, Bagheera. Let's do it."

"Excellent! I was hoping you'd say that."

Following Bagheera's instructions, Simba rolled to his feet, lowering his chest to the ground and raising his rear as high as he could, his tail raised up, the tuft of fur at the tip hanging down like a lure, drawing attention to his ass. Once the cub was in position, Bagheera stepped over him, using one paw to hold Simba gently but firmly in place while he squatted down and lined himself up, until the tip of his cock was pressed against the cub's pink pucker, Timon's cum smearing against it as it leaked out.

"Alright, Simba, I want you to relax as much as you can," said Bagheera. "This might be a bit uncomfortable at first, but once you get used to it, I promise you're going to love it."

Bagheera began to slowly press forward, gradually increasing the pressure against Simba's tailhole. Even after getting fucked by Timon, Simba was still pretty tight, not really surprising considering the meerkat's size. But that had Bagheera even more eager to have his way with the cub - the promise of that tightness around his cock was just too tempting. It was hardly the panther's first time fucking someone smaller than him, so he knew what he was doing, and in no time at all, he sighed in pleasure as the head of his cock slipped past Simba's resistance, and inch after inch of panther dick sank into the cub's golden rump.

Simba yelped and squirmed as he was mounted by the bigger cat, his insides stretching to accommodate the panther's thick shaft, but Bagheera held him down, slowly and steadily working himself deeper and deeper until suddenly Simba felt the other cat's big black balls press against his much smaller pair. Such a quick entry would normally have been uncomfortable, if not outright painful for the cub, except for two things - first, Timon's cum made for an excellent lubricant, keeping Simba's insides nice and slick to ease Bagheera's entry, and second, the big cat's cock was absolutely crushing Simba's prostate, leaving the young cub wriggling in sensory overload at the pleasure washing over him.

After giving Simba some time to adjust to the new feeling of being spread wide around a mature male's cock, and to give himself some time to get used to the tight grip of Simba's tailhole around his length, Bagheera pulled his hips back, and as he did, Simba mewled and squirmed even louder and harder than before at the feeling of Bagheera's barb-covered penis plucking gently at his insides as the big cat pulled back. Bagheera immediately set into a steady rhythm, pumping his cock in and out of Simba's backside, enjoying the cub's tight squeezes over his cock, the young cub making the cutest noises as his prostate was pummeled and that big barbed panther dick stroked over places deep inside that Simba didn't even know he could feel.

They'd been going at it for several minutes when Bagheera was forced to stop, buried balls deep in the cub as Simba let out an especially loud squeal of pleasure and squeezed down hard on his dick. Over the sound of Simba's pleased whimpering Bagheera heard the sound of gentle sucking, and looking down he quickly found the source - Timon had slipped underneath the rutting pair, and had sunk his mouth down over every inch of Simba's dick, deepthroating the cub and fondling his golden furred sac. Glad to see that he hadn't hurt the boy, Bagheera went back to riding the cub's tail for all it was worth.

The added stimulation of the warm mouth on his cock and the stiff length in his ass was too much for Simba's young body to handle, and with a last cry of pleasure he came, pumping a respectable load down Timon's throat as the meerkat did his best to suck down every drop of lion spunk he could get. The spasmic squeezing of the cub's tailhole around his cock quickly pushed Bagheera over the edge. He buried himself to the root under Simba's tail, roaring as he pumped the young lion's ass full of his hot cum, pumping the bottom inch or so of his shaft in and out of that tightly squeezing rear as his balls pulled up to his belly and emptied into the golden-furred youngster. It was far too much for Simba to handle, and Bagheera could feel the fur on their sacs sticking together as his cum spilled out of Simba and ran down the back of the cub's balls.

As Bagheera pulled out, a stream of cum spilled out of Simba's tailhole, only to be quickly lapped up as Timon moved quickly into place to clean up Simba's cum covered backside.

"Oh, I needed that," said Bagheera, sighing in pleasure. "So, Simba, what did you think of your first time getting fucked by a bigger male?"

Simba, who was busy moaning at the feeling of the small tongue lapping at his stretched and pleasantly sore tailhole, took a few moments before he was able to gasp out an answer.

"It was ... that was ... I just ... wow!" said Simba, a dopey grin on his face. "I don't think I've ever felt anything that good. Next time, can we do that some more?"

Bagheera laughed, "Of course we can. But let's not worry about that now. Afterall, we're not done this time."

Simba tilted his head, confused, "We're not?"

"Not just yet," replied Bagheera. "After all, a male's first time isn't really finished until he gets to mount someone. And besides, why should I be the only one that gets to enjoy fucking someone smaller? Wouldn't you agree, Timon?"

Timon's body went rigid, and he pulled his face out from under Simba's tail, the fur on his face smeared with panther cum. "Are you saying what I think you're saying?"

"Well, I mean, it seems only fair, doesn't it? Simba's first time getting fucked was by you, so the way I see it it's only right that his first time fucking someone else be with you. What do you say Simba? How would you like your first time mounting another male to be with our little friend here?"

By now Simba had climbed to his feet, his young penis hanging stiffly between his hindlegs. Timon's attentions to his tailhole had felt good enough that Simba's erection had quickly returned, and as he thought about fucking Timon, he could feel himself getting even harder.

"Yeah, let's do it!" exclaimed Simba excitedly. "I mean, if it's okay with you, Timon."

Timon was momentarily speechless, looking back and forth between the two big cats surrounding him. Then his eyes dropped to stare at the barbed length hanging under Simba, and a tremor of lust shook the meerkat's body at the thought of taking the cub's dick. Bagheera's size meant that while he could take some of the panther's length, he couldn't take it all. It was just too big. But Simba was close enough to his own size that there was a very real chance you could do it. He reached under Simba and gave his cock a few loving strokes.

"Sounds good to me," said Timon. "Alright, kid, why don't you show me what you can do with this." He gave Simba's dick another teasing squeeze.

"Simba, since this is your first time, why don't we let Timon take the lead," suggested Bagheera, raising a paw and pointing a paw at a nearby tree. "Take a seat over here and lean back."

Simba did as he was told, flopping down against the tree, his hard cock sticking up between his spread legs. Timon didn't waste any time before sinking his mouth down Simba's shaft, bobbing his head quickly to get the boy's penis nice and slick before the real fun began. When he was finished, the meerkat quickly climbed on top of Simba, facing away from the young lion and raising his tail as he lined himself up. Timon had always enjoyed watching his cock sinking into a nice tight tailhole, and he wanted to give Simba the same opportunity for his first time. Resting his pucker against the tip of Simba's cock, Timon took a moment to mentally prepare himself. Then, bracing his feet against Simba's legs, he began to push himself down, moaning loudly as he sank down, until every inch of warm, barbed lion penis was buried inside him.

Simba and Timon both moaned out in pleasure as the young lion's dick spread the meerkat's tailhole wide. After sinking all the way down until his own rear was flush with the lion's crotch, Timon shifted back and forth, enjoying feeling the (to him) large cock stroking his insides while letting Simba feel the tight grip Timon's ass had on his cock. Timon started to raise himself up to start riding the young cub, but his knees nearly gave out at the wonderfully strange feeling of the lion boy's small barbs tickling and teasing him as he moved. He settled into a slow rhythm that would let both males enjoy the experience for as long as possible, his own small dick shooting lines of precum into the grass every time he hilted himself on hot, meaty lion cock.

But the feeling of stuffing his dick into the small, tight male in his lap was an overwhelming experience for the inexperienced lion. He was eager to feel even more pleasure, and Timon's slow and steady pace wasn't fast enough for the eager, horny little lion. He reached out and grabbed Timon in his paws as best he could, pinning the meerkat's arms to his sides, before he began bouncing the meerkat on his cock, forcing Timon to ride him hard and fast, thrusting his hips up to meet the meerkat's rear as he was pushed down, pounding the smaller male hard and fast, the pleasure spiking and driving him on.

Simba's fast pace was hitting all of Timon's most sensitive spots relentlessly, giving the meerkat no time to get used to all the feelings washing over him, the barbed lion penis making him feel things he'd never thought he'd get to feel, the wonderful feeling of having a big predator buried balls deep in his ass. But the thing that final pushed the rutting pair over the edge was when Bagheera stepped forward and bent his head down, lapping over both small sacs and the pink cock bouncing against Timon's belly.

The feeling of that sandpapery feline tongue running over their most sensitive bits was too much for either of them to take. Forcing Timon down one last time, Simba thrust his hips so hard his rear was off the ground, letting out his own small roar as he pumped his load into Timon. The feeling of the cub's cock filling him with that liquid warmth he loved was enough to trigger Timon's own orgasm, his legs kicking uncontrollably as he came, Bagheera's rough tongue prolonging his pleasure and mixing it with a little pain as the panther licked up every drop of tasty meerkat cum.

When their orgasms had slowed to a stop, Simba collapsed, pulling Timon down with him to rest against his chest and belly, both of them panting as the lion boy's cock still slowly leaking cum into his small friend. When he could finally speak again, Simba shakily raised his head to look down at Timon.

"Hey, Timon?"

"Yeah, kid," panted Timon. "If you want to go again, I'm gonna need a little while to recover first. You did a heck of a job for your first time."

"Thanks," said Simba, blushing. "But actually, i wanted to ask you something else."

"Yeah? And what was that?"

"Well, I really like this sex stuff, and I want to try doing it some more," said Simba. "But next time, do you think we could try doing some things with Pumbaa, too?"

Timon laughed, patting his stomach, where he could swear he could feel the bulge of the cub's cock still buried inside him.

"Oh, don't you worry about a thing, kid. I think that can definitely be arranged."