Diddy Kong was travelling to a certain island he hasn't been to in so long. An island where he met many good friends when he was younger and fought off some space... alien... wizard pig? Yeah, he still has no idea what the deal with that is. But regardless, he has kept in touch with most of them. Banjo for instance and hearing his adventures. As for Conker... well, there's a reason most don't talk about him anymore. Poor guy fell HARD.
Diddy arrives at the island and looks around. Not much has changed over the years. But he himself has. He has a more curvy and feminine body. Thick thighs, curvy hips, a plump rear and found out more about himself that he likes having sex. Especially with the same gender~ Yes, there was no denying it, Diddy is a huge slut and he's not ashamed of that.
He finally locks eyes on a certain tiger and walks towards him.
"Timber!" Diddy greeted as the tiger boy in questioned looked at the monkey and was quite surprised at the transformation. Diddy still wore a red tank top and his hat. But he also wore some shorts with some stars on them. He also has a backpack with him.
"Diddy! Wow... I haven't seen you in forever! You, uh... grew up." Timber said, looking at his friend's body.
"Yep, yep! And you grew up too. Still cute as ever~" Diddy teases with a giggle, making the tiger blush and crossing his arms.
"I'm not cute! I'm handsome. Anyways, what brings you here?" Timber grumbled before perking up again.
"Just wanted to hang out with my friend. Say, I have an idea! Why don't we have a race? Like good old times?" The feminine monkey boy says, his voice filled with excitement and his tail swishing back and forth like he's part cat.
"Hmm... it has been a while. What are the stakes?" Timber asks, interested. He has gotten a bit rusty since, well... he still has job to guard the island he grew up on.
"Bragging rights and the loser has to do something." Diddy says with a smile. That seemed a little vague, but whatever. Timber's game. He still has the cars, hovercrafts and planes. "So, you in dude?"
"Oh, I am so in. I'm gonna kick your ass." Timber said with a grin as the two shook hands.
'That's not all you're gonna do~' Diddy thought with lewdness. Of course he had an ulterior motive.
The races began and Diddy began to lose intentionally on purpose. At first, Timber didn't notice, but over time, it was becoming more blatant. Especially Diddy's comments.
"Oh no! I lost again! Oh well. You're just too good Timber!"
"Aww, I was just too slow. Maybe you will kick my ass."
And so on and so forth. Timber was starting to get suspicious.
"Well, I lost. Guess it's time for the winner to decide. But first, lemme get ready." Diddy says and that left Timber confused. Ready for what?
He turns around and thinks for a moment. Why would Diddy lose on purpose? He knows he's a skilled driver and his karting experience helped him improve even more. It just didn't make any sense. Plus, he's been acting weird since he got here.
"Look, Diddy. I don't know what you're planning. But I think you-WHAT THE HELL?!" Timber began and turned around, and his eyes widened at what he saw.
Diddy was already dressed in his slut attire, as he nicknamed. He wore thigh high red socks, red arm warmers with yellow star patterns on them, and a red thong that did little to hide his crotch. His red hat now had the word 'SLUT' written on it.
"I had to get more comfortable. Hope ya don't mind, buddy." Diddy says, as if this was completely normal.
"Where the hell did you get that and why are you wearing it?! I thought had a girlfriend!?" Timber cried out, pointing at him in shock.
"Oh! I also got you stuff too. Ta-da!" Diddy scrounged up in his backpack and found blue thigh highs, blue arm warmers and a blue thong. Along with a very familiar gold symbol on the side. Rareware.
"WHY DO YOU HAVE THAT?!" Timber shouted. Now he was more confused. Was this... was this his own outfit too? Why?! "And you still haven't answered my question! I thought you were straight! What is all of this?!"
"You mean Dixie?" Asked Diddy. "Yeah, we broke up. Her loss."
Timber blinked twice. Diddy and Dixie broke up? But why? "Turns out I like boys better than girls." Diddy continued. Answering Timber's question. "Pretty much everyone wanted to fuck me. Especially with a body like mine~"
This was… Out there. It's been so long since Timber had last seen Diddy, so what exactly changed before this moment? "I… Are you serious about this? Is that why you lost on purpose!?" Timber exclaimed. Diddy nodded. Acting like this was all normal for him.
"Pretty much." Diddy replied. "Not gonna lie, I've been feeling a little horny during my trip here. And I almost forgot how handsome you looked, Timber~"
Was Diddy really acting like this? Hell, was this Diddy AT ALL?! Or was he being mind controlled somewhere? "Now then, why don't you put these on?~" Diddy went on. Holding up the outfit he had just revealed. "Trust me; you'll feel a lot better than in that plain old hat~"
Timber looked at the outfit, then Diddy slowly, and then back to the outfit. This was really happening and he isn't some weird screwed up dream. Okay. Cool. The tiger slowly reached it and starts putting it on, as Diddy watched like an excited kid gifting him with a present.
Timber put on the thigh highs, arm warmers and thong. It was nice and snug. It was actually kinda comfy in a way. But he seems so embarrassed. He feels so... exposed. Thank God, it was just the two of them alone.
"... Mmmm... O-okay... now what? This is so weird..." Timber asks and mumbles the last part to himself.
"Yay! You look so good, Timber! We match!" The monkey boy cheers, his tail wagging back and forth in happiness. "Soooo...  since I lost. You get to do whatever. And I know just the thing."
Timber raises an eyebrow at that as Diddy clears his throat and gets into it.
"Oh Timber, please don't use me and violate me for your... sexual needs...! But as the winner, you have the right to do it. I will obey!" Diddy said with as much drama and gravitas as possible. Timber couldn't help but snort and start laughing.
"Oh my God...! Stop, stop, stop... I... I can't...!" Whatever embarrassment he had at the moment, faded as the monkey was so over the top.
"Too much?" Diddy asks, tilting his head cutely and blushing a little.
"I think it's obvious you wanted me to fuck you a while ago, dude. Seriously, don't quit your day job." Timber snarked as his monkey friend rubbed the back of his head and chuckles.
Diddy got onto his knees and began fondling the bulge in Timber's thong. "I'm all yours, Timber~" He whispered before moving it to the side and allowing the tiger's cock to spring free. "Oh! You're huge!"
Timber smirked hearing that. Really getting into it now. "Think you can take it~?" He teased.
"I've taken lots of cocks before, Timber; I'm pretty sure I can handle yours'~" Diddy replied as he stroked Timber off. "Mmm… Looks tasty~"
Diddy winked at Timber before opening his mouth and taking his cock inside. "Oogh!!" Timber moaned loudly. "Holy shit~!"
Timber stood there as Diddy sucked him off with the skill of an expert. Bobbing his head, swirling his tongue, occasionally glancing up at him, the works! This begged the question: How many times had Diddy done this? Ah, who cares? This felt too good for pointless questions like that~
Timber rested a hand on the back of Diddy's head. "Mmgh! Suck my cock, Diddy!~" He groaned. "God, you're adorable~!"
'I know I am~' Diddy replied in his mind as he shuddered from the praise. 'You're quite the looker, yourself~'
Timber starts moving his hips, thrusting inside Diddy's mouth as he can hear the slutty monkey's muffled moans and loud slurping. He has done this before, huh?
"Ohhh, fuck, Diddy...~ This is actually awesome...~" Timber moans out, as Diddy let him have full control. He was just along for the fun. The monkey femboy wrapped his arms around the tiger's waist and closes his eyes.
'Oh God... so delicious~ Cock always tastes so good~' Diddy thought to himself with a smile, his own cock poking through his thing.
"You love sucking dick that much, huh? How about... THIS?!" Timber growls and starts shoving more of his length down Diddy's throat, making him gurgle.
The monkey opened his eyes, half lidded in pleasure as he stared at his friend with the most submissive and lustful stare imaginable. It was clear, he loves this~
This went on for a while before Diddy began tasting pre. "Nngh! I think I'm gonna cum!!" Timber groaned out. "Hope you're ready for it, Diddy!~"
'Oh, yes I am~!' Diddy thought lustfully. 'Gimme all your cum, Timber!~'
After a few more hard thrusts, Timber roared as he came down Diddy's throat. "Aaagh!!! Take my cum, you slutty monkey!!" He hollered. Diddy's eyes widened in surprise, but they quickly closed again as he swallowed the tiger's load. When he was finished, Diddy pulled away and swallowed the rest of Timber's cum. "Haaah~ Fuck yes~!"
"Phaa… Hah…" Diddy took some breaths. "So yummy~"
Timber helped Diddy back up. Once he did, however, he reached around gave the monkey's ass a hard slap. "AH!" He gasped. "You want more?~"
"I can't help it. Your ass looks so fuckable~" Timber shrugged. Making Diddy giggle shamelessly.
Diddy turned around and spread his plump asscheeks. Giving Timber a good look at his prize for winning. "Go hard~" He commanded. "Pound the shit out of me until I can't walk straight!"
Timber moved Diddy's thong aside, exposing that eager and twitching hole and freeing his cock and balls. The tiger grabbed his friend's waist and slowly nudged his cock at his anus, before shoving inside. Both males moaning as Timber began moving his hips.
"Oogh! Oh fuck...!~ That's it, baby...~ Just what I needed, ehe~" Diddy gave out a low moan, and once again, let Timber take control. He wrapped his tail around the tiger's waist and the sounds of their panting and skin against skin could be heard.
"MMmhg... aahhh... H-holy shit... how is this better than a girl's?! No wonder guys fawn all over you, dude!" Timber moaned out, watching as Diiddy's plump cheeks jiggle upon contact.
"Right? They can't get enough of my bubblebutt~ Now, c'mon Timber... really give me that glorious dick of yours! I'm not a pussy!" The monkey boy says with a cocky grin. Oh, he wanted to go all the way? He's really that eager?
"You want it rough, buddy? I'll give it to ya!~" He holds Diddy tightly and slammed into him hard, rough and fast. The monkey's eyes roll back and he smiles.
"Oohghg!~ Oh fuck yes!~ Right there! You're... aahn!~ S-scratching that spo-aaah! SPOT! Oh, damn...!~" The slutty monkey moaned loudly, his own cock twitching and leaking pre.
The two males kept going at it. Diddy's bubbly asscheeks kept bouncing and jiggling while he and Timber moaned and groaned loudly. "Hnng! God yes!!" Diddy hollered. "I love having your cock in my fat ass!!!"
Timber responded by giving Diddy's ass another spank. This one being so hard, it left a bright red mark on his cheek. "AHH!" Diddy moaned as he reached down and began masturbating. "Fuuuck~ This feels so fucking good!!"
Timber moved Diddy's hand out of the way and jerked him off for him. The pleasure of having both his cock and ass being pleased unison was all too much for Diddy and he let out a loud shameless groan. "Aaaahn~ This is the best ever!~"
"Nnhghg... Rrrgghhh... f-fuck... your ass is amazing!~ If I knew it was... ahhh... G-gonna be this great, I would've fucked you ages ago!~" Timber says between moans, he pins Diddy onto the ground, still stroking his cock.
"Hhngh! I... I'm gonna... c-cum! Oh God, I'm fucking getting close!!~" Diddy panted out, closing his eyes and giving out whimpers.
This went on for a while, until finally, Timber slammed deep inside and came in the monkey. Both males moan loudly, as Diddy shot his load all over the ground, his body shuddering.
"Ooohh... y-yeah... f-fill me buddy... F-fuckin'... fill me...~" Diddy moans with utter bliss, he slowly opens his eyes and looks so happy. The warm cum felt so good.
Timber pulls away and sighs, watching his handiwork with Diddy's loose ass and leaking cum. The femboy monkey lies on his back, catching his breath from the intense fucking and session.
"Hhah... oh yeah. That was amazing~" Diddy says and is surprised to see Timber hovering his ass on Diddy's cock. "Uh... what'cha doin'?"
"Well, it doesn't seem fair that you get to be the only one enjoying it. I thought I'd give it a shot." Timber explains, nudging his tight anus at the tip.
"Mm-mmh... N-not that I'm complaining, but I never fucked anyone. I'm usually the one being fucked. Besides, have YOU done this before?" The monkey asks, whimpering as he felt Timber trying to lower himself.
"Mmm... not really. Hey, this can both be our firsts!" The tiger said with a chuckle. And Diddy found himself excited. He always wondered what it felt like on the other side.
Timber winked at Diddy before lowering himself onto the monkey's cock. The two males moaning loudly as he did so. "Hnng… Oh fuck~" Timber groaned. "Y-You're so big~"
"Wanna start slow, then?" Asked Diddy. Timber shook his head.
"No, I can take it! Just watch me!" He retorted before moving up and down. "Oogh! Fuck yeah~"
"Mmgh! God, your ass is so tight!~" Diddy moaned as he grabbed hold of Timber's hips. "It kinda feels good to be the dominant one for a change!"
The both of them kept going at it. Timber bounced up and down on Diddy's cock while Diddy held Timber's hips tightly. In the heat of the moment, Timber reached down and began jerking himself off. Was this really what he was missing out on? He felt so stupid for refusing beforehand!
"Aaahh... ahh, aahh! Oh, yeah... this feels even better!~ No wonder you do this so often!~" Timber moans out, riding Diddy's cock as the two moan in pleasure.
"Mmmh... it feels amazing~ See? Isn't this so much fun?~ Go deeper!" Diddy says and smiles, moving his hips until the tiger did as he was told, slamming himself deep on the monkey's cock, balls deep. "Aagh!~ S-shit...~"
"Oohh... I... I don't wanna stop...!~ Fuck, it feels awesome!~" Timber moans, his tongue lolling out as he rises and falls quickly, feeling Diddy's cock hitting his prostate and giving small squeals of pleasure. "Hnh!~ Hha!~"
"Nnhgh... w-wait 'till you suck me off~ You'll enjoy it much better too~ Want me to-" Before he could finished, Timber nodded vigorously.
"YES!~" He shouted with glee.
"Dunno why I asked. You wanted it!~" Diddy gripped his friend's waits tightly and bucked his hips rough and fast. "Take it, tiger bitch!~"
The pleasure was so much, Timber's eyes had fully turned to hearts as his cock twitched. "HAAAAGGH!!!" He screamed in ecstasy as his mind shattered. "YES! FUCK ME MORE, DIDDY!! I LOVE YOU!!!"
Diddy laughed a bit. Who knew Timber could be so slutty?~ "Haha! Love you too, Timber~" He replied before his cock twitched inside of Timber's ass. "Nngh! I'm about to cum…!"
"Cum inside me! Pump me full!!" Timber begged and pleaded. "Fill me like a fucktoy! I need it!!!"
And with one final push, Diddy and Timber came in unison while they hollered in ecstasy. Diddy's cum filled the horny tiger while Timber's cum stained the ground beneath him. "Haaah~" Timber sighed in bliss. "That felt so good~"
Timber began to stand up, but Diddy's voice stopped him. "Wait, hold on." He said. "Let me just…"
Timber raised an eyebrow and was about to question Diddy, but then he felt a warm liquid inside of him. Was he…? Yep, he was pissing inside of him. "Oooh…" Timber moaned softly. It felt… Strangely good~
"How does my pee feel inside your ass~?" Asked Diddy. "I've always wanted to try that."
"Mmn~ Fuck yeah~" Timber breathed. When Diddy was finished, he shakily stood up and allowed some leftover cum and urine to drop out of him. "Thanks for that Diddy~"
"Don't mention it, Timber~" Replied Diddy. "Say… How would you like more?"
Timber cocked in his head in curiosity. What was Diddy planning? "Let me tell ya: Being a slut gets lonely sometimes. I'd love to have a partner to join me~" He continued. "Interested~?"
Timber's heart began racing. "Of course, Diddy!" He said excitedly. "Can I… Can I be with you too?"
Diddy smirked naughty. "Hell yeah, you can~" He replied. "We can be partners~!"
The two males embraced each other and began making out. Sealing the aforementioned deal and signalling the beginning of anew routine for them~
[…]
A couple of weeks have passed since they had their moment on the island. Diddy and Timber were no together and of course, doing what they do best. Being absolute sluts eager for sex and cum~
Diddy invited some horny men to have their way with them. Diddy and Timber wearing their outfits of course, and excited for some lewd fun~
"Hi guys~ I brought a friend. He's my childhood friend and partner~ Give him as much cock and love as you do me!~" Diddy announced and gave a wink. "Trust me, he's femboy slut material too~"
And with that, the sounds of skin against skin and moaning could be heard. Diddy gladly taking a cock in his ass, sucking one and giving handjobs to the others surrounding him. Timber was also having the time of his life, moaning loudly as he was riding on one male's cock and stroking the others.
"Aaahn!~ Hhngh!~ Y-yess!~ Please gimme your cocks!~ I can take t! Shove more in, please!!~" The tiger loudly moaned out, not caring how he sounded. The two were in their element and were rewarded with tons of cum and piss.
And whenever they were alone, they started making out like passionate lovers and doing all sorts of lewd activities. Diddy and Timber right now were in a 69 position, sucking each other off with such excitement.
They loved being so slutty with each other and Timber never wanted to stop. He has embraced this new lifestyle with Diddy. Soon, the two got close and came inside, filling each other's mouths.
"Pfha... Fuck, I love this... Say, you wanna join me in Smash as a plus one? I know some guys that'll love you~" Diddy said, parting away from Timber's cock and stroking him slowly.
"Really?! But wait, I'm not a fighter. Not even as an assist-" Timber started before the monkey kisses his cock.
"You didn't let me finish. I mean as a plus one as the Smash slut~ I'm not the only one. I know a cute kitty phantom thief and some weird cat, rabbit thing. Soooo...?~" Diddy waited for his answer, and was met with his dick being sucked on again. "Mmh!~ I-I'll take that as a yes. They're gonna LOVE you~"
And they started all over again. The sounds of loud slurping and muffled moans could be heard. This reunion was worth it~
END