Diddy Kong was hoping to spend some time with his girlfriend, Dixie, only to find out she wasn't home at the moment in the treehouse. He couldn't just up and leave after making his way here. He might as well wait until she finishes her business. It could be a good surprise when she comes back.
But what could the monkey boy do to pass the time? He looks around, there was her guitar that she and Diddy use to jam out from time to time. He wanders around the house until he stumbles upon her room. He knows he shouldn't pry into her business. But one, he was bored. And two, she wasn't here. So...
"Just this once. And Dixie'll never know." Diddy says to himself, and looks around, eventually stumbling upon one of her spare outfits. A pink beret, a top, some kneepads and a pair of panties.
Diddy blushes a deep red, having never been exposed to this before. But on the other hand, something compelled him to just... try them on. He has no idea why though. He looks around, making sure nobody was nearby.
"I guess... it couldn't hurt." The male monkey whispers quietly.
He takes off his shirt and hat and starts putting on Dixie's clothes. The hat felt comfy and snug, the kneepads fit, the shirt was a bit strange, but felt comfortable. And the panties were a little tight for obvious reasons.
"M-mmh... there." Diddy grunted a bit, feeling the tightness around his crotch. He goes over to a mirror and checks himself out. He almost looks like his girlfriend, save for the long flowing blonde hair and being male.
Diddy, began rubbing his nipples, giving out a quiet whimper as he feels the sensitivity on them. He uses his tail to lower his panties and then stroking himself, getting his penis erect.
"A-aahh... ahh... I-I can't believe I'm doing this... m-masturbating... i-in girly clothes...!" Diddy says to himself quietly, his tail rubbed and stroked his erection, getting it hard as the monkey boy played with his nipples.
He twists and turns them, eliciting some moans from him. He has no idea what's gotten into himself, but he found that he enjoys being so... feminine. He bit his lower lip as he began moving his hips, thrusting into the air as he moved his tail faster and started panting heavily.
"Hahh...!~ Hhah... I-I'm gonna cum...! I'm gonna cum...!~" He gave out a low moan, spraying his load all over the floor and sighs. He sank to his knees and was recovering from his climax. Then, it occurred to him. He just masturbated in his girlfriend's house, stole her clothes and did this.
He felt like a shitty boyfriend. Plus, he has to clean the mess he's made before she comes home. After taking off Dixie's clothes and cleaned up the mess, he acted like nothing happened when she returned home and hung out.
This went on for a couple of days. Diddy arrived to see that Dixie was out again, he went to her room and tried out her clothes again. At this point, he had gotten used to wearing some feminine clothes. Of course, he kept it a secret.
Like the other times, Diddy gained an erection. "Mmmn… I can just imagine someone seeing me like this. That'd be hot, actually~" He shuddered in excitement.

Diddy wrapped his tail around his cock and began jerking off with his hands behind his head. Moaning loudly as he did so. After all, he figured Dixie wouldn't be back for a while~ As he sped up, Diddy felt himself getting closer to his orgasm. 'Already?' He thought. 'Ah well. This feels too good to stop!'
Diddy practically screamed when he came. His cum shooting out and onto the floor. Diddy let out a sigh. No matter how many times he did this, it felt good every time. Now all he had to do was clean up before-
"Diddy?" Said a familiar voice. Diddy gasped when he saw the source: It looked like Dixie was home early, and he knew he'd been caught.
"D-Dixie! You're home early!" Diddy said to try and lighten up the mood. However, it didn't work at all.
"Were you…? In my…? WHAT THE FUCK?!" She exclaimed. Needless to say, Diddy was taken aback by this. She never lashed out on him like that before! She must be really angry with him.
"I-I can explain!" Diddy stuttered. Tears welling in his eyes in fear that Dixie would break up with him, or worse, tell someone about it.
However, instead of just slapping him or anything like that, Dixie noticed Diddy's tears and calmed down. Simultaneously gaining an idea. "Looks like this is gonna be the end of it… Unless you do what I say." She said.
"Wh-What do you want me to do?" Asked Diddy. Nervous about what his girlfriend was planning.
Dixie stared at her boyfriend. It's weird, how did he manage to pull off wearing her own clothes? He looked so comfortable too.
"First off, we need a change of clothes. It's obvious you like... girl clothes very much." Dixie says, eyeing the male monkey.
Diddy just blushes a deep red, not knowing what to say. He couldn't exactly defend himself since she was right. He wiped away his tears, trying to calm himself down.
"L-like what...?" He asked, curious as to what his girlfriend has planned.
"You like the color red and start patterns, right?" She asks, to which Diddy nodded on confusion. "Then I think we have the perfect outfit for you~ BUT! If you wanna keep this a secret, you'll do what I say. Deal?"
Diddy thought about it for a moment. He didn't want anyone else to know. They would think he was a damn weirdo or worse. He saw his girlfriend's outstretched hand. He sighs and shakes on it.
"Please, please, please don't tell anyone..." Diddy whispered, so embarrassed being caught like this. But on the plus side, she didn't wanna break up with him.
"I won't tell a soul… Unless you become a slut." Said Dixie. Pausing for dramatic effect.

Did… Did he hear right? a slut?? He wasn't gay! He had a girlfriend for fuck's same! "Y-You're crazy!" Diddy exclaimed. "Although, if it's to protect my secret…"

"That's the spirit~ Come with me; I've got a much better outfit for you." Said Dixie.
[…]
'I can't believe I'm doing this…' Thought Diddy. He was in a replica of Dixie's outfit, only this one was red and stars on it. Both he and Dixie were deep in the jungle. For what reason? He didn't know. Still, this was better than being broken up! He guessed…
Eventually, the two reached a clearing with something in the middle of it. It was a suspended plank of wood with three holes cut into it. Two were smaller, one was larger. "There it is, Diddy." Said Dixie. "Why don't you get yourself situated?"
"I-If you say so…" Sighed Diddy. He walked over to the strange object and stuck his head and hands through the holes. "Is that it?"
"Hmm… Not just yet." Said Dixie. What was she doing? Diddy was kinda afraid to find out…
Suddenly, he felt something large being inserted into his ass. "Aah! What are you doing!? That hurts!" Diddy exclaimed.
"It's just a dildo. Don't be such a sissy." Dixie explained. "Although, Sissy Kong kinda has a nice ring to it~"
Diddy blushes some more as he squirms, feeling the dildo inside of him.
"N-nnh... ah-ahh... I-I never... ahh..." Diddy moans quietly, this all felt so weird to him. But on the other hand, it felt oddly good.
"Now then, since you look so presentable. I'm sure you'll be quite the hit, Diddy~" Dixie says and giggles.
Diddy was confused, why was he here and what did she mean by that? What exactly would he be doing?
"N-nnnh... M'not a si... sissy..." Diddy struggled to say, as he squirms from the dildo inside his ass.
He waited a bit, but when Dixie didn't respond, he got nervous. Did she abandon him? Leaving himself vulnerable to whatever she had planned!? "Dixie!?" He called. But like the last time, he heard no response from his girlfriend.
…Or was it ex-girlfriend now?
Diddy's tears came back and he started crying. He was just curious, he swore! Why did it have to come to this?? "Please come back, Dixie… I'll never do it again…" He sobbed. However, there was no one to hear him this time. So, all he could do was wait for Dixie to come back. There was still a slight chance that this was all some kind of sick joke.
Suddenly, Diddy heard leaves rustling. Was it Dixie? Oh please, PLEASE let it be Dixie! "Dixie?" He called. However, the response he got was anyone but Dixie.
"What do we have here~?" Asked an all too familiar voice. Oh no. No, no, no! Not him! Please, anyone but him!
The voice in question was none other than his and DK's rival, King K. Rool: Ruler of the Kremlings. Shit! Diddy was screwed, wasn't he?! "What're you doing here?!" Diddy exclaimed. Trying and failing to act tough.
K. Rool walked around to face Diddy. "I should be asking you the same." He replied. "No matter, though; this should be worth my time~"
Diddy's blood ran cold. "What're you talking about!?" He gasped. Was this his comeuppance for dressing like Dixie? Did she sell him to the Kremlings?! She would never do that! …Would she?
K. Rool gave Diddy an evil grin, looking at the crossdressing monkey trapped and in the situation he's in.

"My, my... who would've known that one of my enemies are into... this?" The Kremling king mocks him, Diddy was panicking now. None of this makes sense. Why is he here?! "Well, no matter. Killing you would be too easy. Unsatisfactory. No. I think a much better idea would be to use you as you are..."
The evil king leaned towards Diddy and his eyes widened at what he heard.
"As a personal Kremling Slut~ And for my personal use as well." He said with such sick glee, almost like he fantasized for this moment.
Now, Diddy was full blown terrified. He tried to get out of the stocks he was in, but found he couldn't.
"Dixie! DIXIE!!! HELP!!!" He cried out, only to be met with K. Rool's bellowing laughter, seeing the normally confident Kong, reduced to this. "No, no, no! This can't be!!!"
"Oh, it's true!" Said K. Rool. "And might I say; you have quite the assets, at that~"
After saying that, K. Rool unveiled his cock. Holy shit, it was huge! His own dick was microscopic in comparison. How would he even take it!?
"W-Wait, NO!!" Diddy cried out, but K. Rool didn't listen and stuck his dick inside the monkey's mouth.
"Mmgh! Such a good slut~" K. Rool groaned before thrusting hard and fast down Diddy's throat. Diddy felt nothing but agony. This was torture! He should've just stopped dressing like Dixie while he still had the chance…
'Why is this happening? Why me??' Diddy thought as he felt K. Rool's cock throb. He wanted to cry and vomit at the same time, but found it impossible to do the latter. The former, however? That was all he could do.
"Ah, fuck~ So fucking good…" K. Rool moaned. "Get ready for my cum~"
Cum? Oh no. No! Nonononono! He wasn't ready for it!
With one final thrust, K. Rool came down Diddy's throat. He moaned in sick pleasure, but Diddy was groaning in agony. His tears increased as he tasted his rapist's cum. As he expected, it was utterly disgusting.
K. Rool eventually pulled away and Diddy coughed a bit. "Please… No more…" He sobbed.
"Now why would I do that when you're hard as well?" The Kremling leader asked as he walked behind Diddy. Wait, did he hear him right? He was erect as well?! It seemed his own body was betraying him just like Dixie did…
As the Kremling king looked behind Diddy, he could see the dildo still lodged inside Diddy's ass. He couldn't help but laugh at the sight.
"Hahahaha! You needed this pathetic thing to satisfy you?! Please. This is garbage compared to this!" K. Rool says and pulls it out, making Diddy squeal in pain at the sudden quickness of it.
Diddy then felt the tip poking at his entrance. This was Hell. This was probably his punishment. All the poor monkey boy could do was sob and act like a scared child.
"N-no...! I... I haven't...!" Diddy babbled, mixed with his sobs, but the cruel king of course, didn't care.
He grabs Diddy's waist and shoves his cock inside, making a noticeable bulge in his stomach from the size and girth alone.
"GHhghhghg! Hhahhhhhhh!!!!" Diddy's eyes widened in horror, screaming in pain.
"Hahaha! That's it...! Scream for me you little monkey whore! You'll be nothing more than some lowly fucktoy!" King K. Rool laughs and starts thrusting inside Diddy.
K. Rool was enjoying himself. The feeling of Diddy's tight ass combined with the sight of his jiggling ass was all too much for him. For Diddy, however? Not so much.

"No more… No more… No… No…" Groaned Diddy before his mind suddenly went blank. The pain slowly but surely faded, and in its place came pleasure. And his groans of pain turned into moans of pleasure.
Diddy muttered something. "What was that?" Asked K. Rool.
"M-More. Fuck me more!" Diddy confessed.
"Be more explicit. And more specific, at that!" K. Rool ordered.
"I… I WANT YOU TO FUCK ME, YOUR HIGHNESS!" Diddy screamed. Not giving a single shit if he sounded like he'd lost his mind.
K. Rool laughed at this. Who know his enemy could become his fucktoy? "That's more like it!" He said before going even harder. "Mmg! So fuckin' good!~"
"Aaaahn~" Diddy moaned loudly as his eyes turned to hearts. There was no way around it, his mind was shattered beyond repair. "Fuck yes! I love having your cock in my femboy ass!"
K. Rool grinned crazily as he felt himself getting close. "You want my cum, slut? DO YOU?!" He yelled.
"YES!! YES!!! FILL ME, YOUR MAJESTY!!!~" Diddy screams, not caring if anyone in the jungle heard him or not. Right now, he just wants to be fucked!
The evil king gave one last thrust and filled Diddy up, the monkey boy's stomach bloating like he was pregnant, feeling the warm Kremling cum inside of him.
"HAHAHAHA!!! TAKE IT, YOU SLUTTY MONKEY!" K. Rool shouts at him, hearing the male's slutty moans.
"Ooohhgh!! S-so much...! Urphh... BLEEGHGHGHGH!!!~" Diddy's eyes roll back as he vomited up the Kremling's cum, the amount was too much and stained the jungle ground, making a puddle.
K. Rool pulls out and watches as his cum leaks out of Diddy's asshole. The monkey boy was struggling to stay conscious from the intense session.
"I must say, you've been the best fuck ever. It would be an awful shame to just leave you, for a girl who seemingly abandoned you." The king says with fake sympathy, all the while, Diddy gurgled from the cum leaking from his mouth. "Wouldn't it be better to be the Kremling Krew's fucktoy? You wouldn't have to be alone ever again!
Diddy lit up at this? A fucktoy for the entirety of the Kremling Krew? He'd have to be a major-level dumbass to pass this up! "Y-Yes! I'll be your fucktoy! I… I love Kremlings~" He confessed. Sighing while saying the last part.
The evil king laughed before setting Diddy free. Lo and behold, he made no attempt to run away nor call for help. He was the Kremling Krew's property now…
[…]
Time had passed since that day, and Diddy had solidified his place as the Kremling's personal slut. His life was filled with cocks and cum, and he couldn't be happier.
As for Dixie? She felt a little bad about what happened, but it was probably for the best. Besides, she needed an excuse to break up with him for quite some time. Whenever anyone would ask her what happened to Diddy, she'd play dumb and say she didn't know. But deep down inside, she knew the full truth.
Everyone had their theories as to what happened to Diddy. From as logical as being kidnapped to more outlandish theories like an alien abduction. Nonetheless, he was the Kremling Krew's property now. But he wasn't complaining~
END