A Funky Friendship 

"Yo Diddy, ya have a minute?"

"Uh, sure." Diddy waved to DK who headed out into the jungle, then turned back into Funky's garage. "So what's up, Funky?"

"That shipment we've been waiting on came in this morning. Did you want to swing by later tonight and try it out?"

Diddy blushed, hesitating to answer. The two of them had a bit of an unusual friendship. While DK and the others maintained a professional friendship with the mechanic, he and Diddy had developed a more complicated relationship. 
Letting it slide one evening when they were all out for a drink, Diddy admitted that he wasn't as into Dixie as she was into him. In fact the spider monkey had a thing for his fellow males as well as his girlfriend. After letting his secret slip out, Diddy was surprised to see Funky not react with disgust, but intrigue. Later that evening when they were alone, Funky told him that he too enjoyed the company of other male primates, and invited Diddy to his garage after hours. They didn't go very far. Just an exchanged handjob or two…but as time went on things escalated further. 

It was Diddy's idea to start introducing anal play to the mix. It started with a bit of mutual fingering, but it didn't take them long before they upgraded to using bananas on each other. After a few weeks though, Funky decided to up the ante and ordered them a double headed dildo. Though surprised, Diddy was excited to keep pushing their late night experiments further. It took nearly a month to arrive, but the time had finally arrived to level up their playtime.

"I…should be able to sneak out once DK goes to sleep. The usual time?"

"For sure little man, catch ya then!" Funky gave him a fist bump and Diddy headed for the door. Funky smiled and his dick twitched in his shorts as he stared at Diddy's butt. "Love that little guy," he mumbled softly. 

… …

"Ah, it feels good to be free of these!" Diddy sighed, pulling off his shirt and hat.

"You said it," Funky replied, stepping out of his shorts. 

The two primates were already rock hard, as they admired each other's bodies. Diddy's length was small but proportional measuring about 4 inches. His balls barely hung from his body, usually remaining tight up against him.
Funky on the other hand, being a larger primate had a notably larger package. He was an impressive 8 and a half inches. His balls hung low, both being the size of small plums. 

"Looking good as always, Diddy," Funky said, winking at the smaller primate.

"Likewise. It's no wonder you have to wear shorts."

Funky chuckled as he grabbed a long box from the shelf. "Good jeans for my good genes, I suppose. Ok, here it is." He placed it on the floor between them, and sat down with his legs crossed. Letting Diddy open the box, they both gasped seeing the immense size of the toy. 

"D…didn't you buy the medium one?" Diddy stuttered. 

"Yeah, I did. This looks a little bigger though.'

"Bigger? Funky it's HUGE!" 

The dildo was a full 2 feet long and as thick as 3 bananas put together. It was far larger than anything the two of them had taken combined. They just stared at it in awe, trying to process the magnitude of the silicone monster. 

"I guess I'll have to return…"

"No!" Diddy exclaimed, cutting him off. "L…let's try it." 

"Yo it's bigger than you are dude! I mean I might  be able to manage, but you'd probably hurt yourself." 

Diddy reached into the box and pulled it out. He then leaned on his back and pressed the tip against his hole. "Go get the lube, and let's find out." 

Though Funky was hesitant, the sight of Diddy presenting his hindquarters was all the motivation he needed to comply. Taking a large pump bottle off of the top of his shelf, he set it on the floor next to Diddy and kicked the box out of the way. Pumping a large squirt into his left palm, Diddy slathered it on his end of the toy. The remaining lube on his hand, he slathered across his hole and pushed in two fingers, loosening himself. 
"Ah," he gasped feeling around inside his hole. 
The sight of the eager monkey turned Funky on further. His cock twitched, shooting a stream of precum onto Diddy's arm. 
"Hey watch where you're pointing that!"

"Maybe you should start with a banana?" Funky suggested, snagging a bunch off of the nearby table. Just to be safe." 

"Ugh, fine," Diddy grumbled. "Get over here and shove one in me." 

Funky broke off one of the largest bananas, and coated it in lube. Diddy lifted up his legs with both arms and puckered his hole at Funky. Getting on his knees, Funky pushed the banana into Diddy in one quick motion. 

"Fuck yeah!" Diddy moaned, his toes curling tight. "That's the spot!" With his tail free, he took some of the lube from the dildo and curled it up beneath Funky. The larger primate smiled as he felt Diddy slide his tail up to his opening, while pumping the banana in and out of the smaller monkey. 
"Feeling good, little man?"

"Oh yeeeeeah! How about you!" Diddy grunted as he forced his tail into Funky's butt. 

"Ah!" Funky gasped, his body penetrated by Diddy's agile tail. "You sneaky little monkey, try this!" Funky moved one finger down the side of the banana and used it to increase the stretch on Diddy's hole. As he did so, he grabbed a second banana and grabbed a bit more lube from the dildo and greased up the fruit. Placing it between his legs on the floor he nudged Diddy's tail with it. Diddy took the hint and pulled out his tail, grabbed the banana with it, and plunged it into Funky's backside. 
"There ya go sport!" Funky shouted, adding another finger into Diddy. 

The two pumped the bananas in and out of each other furiously. Twisting them around and around as they did so, further stretching themselves out. 
"Enough foreplay, Funky, grab that monster and wreck me with it!" 

Funky wasn't even going to complain now. Both of their cocks were continually leaking precum from the constant milking of their prostates. Diddy's chest fur shimmered from the ropes thin liquid across it. Pulling out the banana from Diddy's hole, Funky quickly re-lubricated the dildo and pressed it against the smaller primate. Taking deep breaths, the thick tip slowly stretched him further and further until…POP!

"AAAAGH!" Diddy exclaimed, his tight hole now filled with the thick artificial cock head. 

"Oh shit, are you ok?" Funky asked, hands recoiled back.

"Holy Fuck!" Diddy moaned, eyes rolling back in his sockets slightly. The sudden explosion of pleasure he felt,  quickly caused him to pull his tail back from Funky, dropping the banana. "F…F….orget bananas! It's so big, but…ah…oh it feels so good!" 

Funky's face lit up and he quickly pumped a large squirt of lube into his hands. Rolling onto the floor across from Diddy, he slathered the other side of the toy. Lifting his legs up, matching Diddy, he pushed the tip of the toy against his hole. Being larger than the monkey, he had less trouble as he began pushing it inside. POP!
"OH MAN!" Funky groaned, his cock shooting out a long stream of precum onto his chest. "This is crazy good, dude!"

The two remained motionless for several minutes as their bodies adjusted to the size of the toy. Neither could believe they were able to get the insane thickness into themselves, but now that it had happened, they could only enjoy the pleasure of being stretched to such an extreme. Funky was the first to push more inside. Wiggling his body forward, he slid in another few inches a little at a time. As the tip of it found his prostate, his cock immediately shot out another ample stream. 

Diddy sensing Funky beginning to slide more into it, decided to see how far inside he could get it. He felt a strange mixture of pleasure and pain from how much his hole had been stretched. Luckily for him, the lube was the perfect amount of slickness to keep him from being ripped apart. His own cock throbbed, being touched from the inside by the tip of the dildo. He had never felt pleasure like that before. Scooting toward Funky, he felt the tip of the toy press firmly against his prostate. 
"Oh, yeah!" He gasped, the sensation nearly causing him to orgasm from the pressure.

Funky reached across in front of them and grasped Diddy's cock with one hand. The monkey gasped and his sphincter clenched with the sudden added pleasure. A devious smile grew on his face, and he wiggled his tail loose. Though his arm couldn't reach Funky's cock, his tail was more than long enough. Wrapping around the older primate's shaft, he gave it a squeeze with his tail. Funky moaned and Diddy watched as his older partner clenched around the toy. 

As they worked hand and tail, the pair began to moan and grunt loudly. Their bodies squeezed the dildo back and forth between them, as precum flowed out in steady streams. Their minds going blank, their bodies engulfed in pleasure, and both were nearing climax. 

"Ah, AH, AGH! F…Funky, I'm gonna…" 

"Me…ungh…too!"

"AAAAAAEEEEEEAAAAH!" Both of them screeched, tapping into their primal vocal range. Their cocks throbbed wildly as fountains of cum flew up into the air. Splashing together in mid air, their combined fluids sprayed out over the two of them. 
The pleasure of being stretched so far during orgasm was almost too much for Diddy. He could feel his muscles tense around the thick toy, squeezing it tight. The pressure on his prostate forced out even more cum than he thought he could produce. 
Funky likewise was overwhelmed by the sensations. He couldn't believe Diddy was able to take any of the toy inside his tiny body, since even he had trouble with it. 

After what seemed like an eternity, the two of them had released the last of their cum and were left exhausted in the afterglow. Their holes puckered, aching for relief from the monstrous toy. Releasing Funky's cock with his tail, Diddy wrapped it around the center of the dildo where it was still dry. Pushing himself back with both arms, he slid it out with a loud POP. 
"UGH!" He moaned as his hole slowly flexed and tightened back to a normal size. "Oh man." 

Funky, seeing that the toy was free from Diddy's body, yanked it out of himself with his left foot. POP. Funky's cock twitched as soon as it was free and he shot out a remnant stream of cum. 
"Dude!" Funky gasped, his limbs falling limp on the floor. He was exhausted and could barely move. "What the hell was that? I never came that much in my life!"

"Me, ah…neither," Diddy replied. "Did…did you still want to send it back? 'Cuz…"

"No way, little man! We gotta, ah…do this again…real soon." 

"F…for sure."

The two didn't say another word to each other for the rest of the night. The next morning was sure to include a significant bathing in the waterfalls nearby, but for now the buckets of combined cum would remain in their fur. As their cocks fell limp the two primates slowly drifted off to sleep.