Double Diamond Delivery Day

by Jest

Chapter 4

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“So how are we going to figure this out, huh?” Kent offered. “Because I don't want to return either of you.”

“Maybe we should just… take turns?” Offered Diamond Crown through grit teeth, as if the mere suggestion caused him physical pain.

“I don't want to share him. I saw him first!” Diamond Tiara shouted, stomping her hoof in emphasis.

The human sighed. “Can't we just go with the turn idea? At least until we work out whatever your issue is.”

“Not likely I’m afraid,” remarked Diamond Crown.

“For once I agree with him,” Diamond Tiara exclaimed.

The human sighed once again and ran a hand down his face. “Fine. Whatever, but we are going to deal with this eventually.”

“Sure we will,” agreed Diamond Crown, who sneered at his counterpart. “Isn't that right?”

“Of course it is,” Diamond Tiara replied through grit teeth.

“Augh. I really should have read that warning all the way through,” Kent muttered to himself.

“Right, so who gets next?” Diamond Crown eagerly asked.

“Well it's not going to be you,” Diamond Tiara replied, jabbing a hoof into the other pony’s chest.

“And why not?” Demanded Diamond Crown.

“Because you just got one, duh!” Diamond Tiara declared.

“Well the rule wasn't in place then, so it doesn't count,” Diamond Crown retorted, throwing his nose up.

“That's not fair!” Diamond Tiara whined, turning to the human. “It's my turn now right?”

“Well actually Diamond Crown is right. It wasn't in effect yet so it doesn't count,” Kent exclaimed with a shrug. “Sorry Tiara, that's just how it works.”

The female pony grumbled under her breath. “Stupid femboy and his stupid tiny dick.”

Diamond Crown blew a raspberry at his counterpart. “Serves you right, jerkface.”

Diamond Tiara growled. “Fine, then let's flip for it then.”

Her counterpart nodded. “That sounds fair. Master, do you have a two sided dice handy?”

“Of course,” replied the human, who plucked a flat round circle of metal from his pocket. “Can you imagine paying for stuff with something like this? It's crazy to think humans used to lug around bags of these things.”

Diamond Tiara sighed and rolled her eyes. “Yes technology is grand now can we get on with it?”

“Well I thought it was neat,” Diamond Crown retorted.

“Suck up,” sneered Diamond Tiara.

Kent shook his head. “Alright Tiara, call it in the air.”

“One!” shouted the excited pony as the coin flipped.

Kent caught the coin and placed it on the back of his hand, revealing it to be a two. “Sorry Tiara but it looks like Crown won this one.”

“Hell yeah!” shouted the other male, who pumped a hoof in the air.

“Dammit. I should have known you were going to turn it over at the end there,” Diamond Tiara muttered bitterly.

“Well there ya go,” Kent proclaimed, putting his hands on his hips. “This may not be the perfect system but I’m sure in time you two can come to an understanding.”

“Not likely,” Diamond Crown muttered.

The human sighed. “A man can dream.”

“Whatever, now hurry up and take your turn so it can be mine again,” Diamond Tiara urged. “I want to get my pussy pumped full of human cum as soon as possible.”

“Fine by me,” Diamond Crown began, walking up to the human. “I’ve been itching to get that fat dick of his inside me again since the moment it left my mouth.”

“Wait, hold on a second here,” Kent urged, raising his hands. “I have stuff to do, I can't just spend my entire day having sex.”

The two Diamond’s shared a look as well as a smirk before the male copy turned back to Kent expectantly.

“Let's be honest. You were planning on playing video games for the rest of the day,” deadpanned the pony.

“Well I…” Kent frowned. “You aren't wrong but I did want to get my dailies done at least.”

“And you will! Right after I’ve proven that I can give you the best orgasm imaginable,” Diamond Crown declared.

“Good luck,” spat Diamond Tiara. “I damn near milked him dry.”

“Then how did he fill my mouth to the brim then huh?” Diamond Crown smugly replied.

The female pony muttered curses under her breath and sat down on a large plush chair, crossing her forehooves over her chest. “Whatever, just get it over with,” she remarked.

Diamond Crown grinned. “With pleasure.”

“Hey wait, don't I get a say in this?” Kent retorted.

“Do you want me to stop?” Diamond Crown replied, raising an eyebrow.

The human hummed thoughtfully, but ultimately shrugged. “Fine, you got me there. I am rather curious as to how you two stack up against one another. Since you won't let me literally stack you atop one another.”

“Blech, I’m never letting that factory reject touch me,” Spat Diamond Tiara.

“The feeling’s mutual, bitch,” Diamond Crown replied.

Kent sighed. “So where are we doing this then?”

“Lay on the couch. I wanna ride that dick of yours good and proper,” Diamond Crown stated, gesturing to the large black couch which took up a majority of the living room.

The human blushed slightly, and did just that, shucking off his pants and top as he moved. Though still a little self conscious under the gaze of the two ponies, Kent kicked off his underwear and laid down on the peice of furniture. When he turned back towards his lovers he quickly realized just how hungry they had become.

The male pony was visibly erect, his diminutive horse cock tight against his chest, while at the same time he licked his lips excitedly. Diamond Tiara meanwhile was a little more reserved, and tried to pretend like she was looking out the window while still stealing a glance every few seconds. Being eyed up in such a naked, and almost predatory fashion was strangely arousing to the man, and his own erection stood straight up a moment later.

“Mmm, that's what I’m talking about,” Diamond Crown purred as he mounted the couch and approached his target.

Who lay in rapt attention as the pony looked him up and down, as if contemplating the best possible position to employ. It didn't take long for Diamond Crown to figure out what that was though, as the pony turned around unexpectedly. Exposing his large, quaking thighs, and bountiful butt which shook with each and every movement the pony made.

The sudden about face was a bit shocking to the human, who quickly realized exactly what his partner was doing. Diamond Crown’s small hooves rested on either side of his master’s sides, and the pony’s ass hung invitingly above Kent’s throbbing member.

“Would you be a dear and guide yourself inside me?” Diamond Crown asked, looking over his shoulder with a pouty expression on his face.

The human was bobbing his head before he even realized what he was doing. “Of course!” He exclaimed.

“Thank you kindly,” Diamond Crown replied.

“Augh, gag,” Diamond Tiara exclaimed from the sidelines.

“You catch more flies with honey,” Diamond Crown retorted, while wiggling himself into position.

“And this perv knew what we were like before he bought us. Thus, he's into it,” Diamond Tiara pointed out.

“Fair. I suppose we’ll see who wins soon enough,” stated the other pony.

“I think both of your strategies are good. It's kind of a pleasant change that one of you is a little nicer than the other,” Kent offered.

“Are you ready or do I have to get back there and do that for you as well?” Diamond Crown demanded.

The human’s eyes went wide and he quickly nodded. “Right. I’m ready whenever you want.”

The pony glanced over his shoulder one final time and upon finding that the other male was indeed holding his cock up, began his descent down. “Mmm, there we go. Finally, it's time to see who is the best Diamond,” he muttered to himself.

Kent wanted to offer some manner of retort to the pony’s word, but the soft, plush feel of his lover’s asshole dismissed that urge. Instead, he merely lay back, and watched as the tip of his dick pressed against Diamond Crown’s entrance. The pony adjusted his hips a few times before finally finding a spot that gave him the leverage he required.

The human briefly wondered if he should have gotten some lube ready, but this unspoken question was answered a few seconds later. When with a mighty heave, Diamond Crown lurched back, and took the first inch or so of the human’s cock inside of him. Where he felt the surprisingly slick hole grip around the first part of his length, making the man realize that the pony’s designers had apparently accounted for this.

It wasn't exactly clear if the pony had merely been busy when Kent hadn't been paying attention or if it was built into Diamond Crown’s unique physiology. Either way the human was glad that he didn't have to struggle against an overly tight hole or the unpleasantness that would come with said dryness. The pony meanwhile, had no such considerations, and merely threw himself back, forcing the thick human cock deep into his hole.

Nearly half of the man’s length had already been swallowed by the pony’s incredibly tight yet still welcoming ass. It would have shocked Kent, had he not already experienced how greedy and stretchy these ponies could be. It took mere moments for the feminine pony to adapt, his muscles shifting around in order to give his lover the room he needed to get further inside.

It was an amazing sensation to feel the pony’s internal parts move around in order to accommodate him. The precious few seconds of incredible tightness quickly fading away and being replaced by an intense spike of pleasure. Unlike his counterpart however, Diamond Crown was even hungrier, and he suddenly threw all his meagre weight behind his next push.

With a wet, satisfying slurp, the human’s cock vanished into his lover’s asshole, swallowed completely in a single heave. The confines of the pony’s asshole gripped tight the man’s cock, and for a moment it was almost painful. Then the relief came, and Kent let out a long sigh of pleasure, his muscles falling slack as he laid back against the couch.

“Fuck you feel good inside of me,” Diamond Crown muttered between soft, breathy moans.

“And you feel fucking great,” Kent remarked absently.

“Hmph. Amatuer,” Diamond Tiara added in a dismissive tone.

“Don't listen to her, you’re doing amazing,” Kent encouraged.

The other male grinned, and shot his counterpart a smirk. “I told you I’m the best.”

“Whatever,” Diamond Tiara muttered before pointedly looking away from the pair.

“Now then, lets really get this started,” Diamond Crown whispered huskily.

Kent had no chance to offer a word in edgewise before his lover began to bounce his thick, plush ass on the human’s cock. Immediately the man was utterly enraptured by the sight of the pony’s bountiful flanks shaking and quaking each time their hips met. It only took a few trips up and down Kent’s cock to make him fall head over heels for the sight before him.

His hands reached out and gripped the pony’s ass tightly, kneading the soft flesh as Diamond Crown continued to ride him without stopping. The tight confines of the feminine male’s ass gripped tighter still and a moan spilled past his lips a second later. It was clear that despite the pony’s cock receiving no stimulation, that he was still enjoying himself quite a bit.

His breathy, high pitched moans were more than enough evidence of that.

Soft fur and even softer flesh squished around the human’s digits, which almost disappeared into the pony’s ass. There was just barely enough resistance to Diamond Crown’s flanks to make it feel realistic, while still being the best butt Kent had ever felt. He could have laid there just squeezing and kneading away for hours, but there was work to be done, and the human quickly shook off the pleasure induced stupor which had briefly overtaken him.

His fingers gripped a little tighter, and with each downward descent Diamond Crown made, Kent pulled hard. While at the same time he thrust up into the pony’s tight backside, stuffing him full of cock. Each time their hips met it was with a heavy thump, and an even higher pitched moan came from Diamond Crown.

The human however, barely made a sound, only uttering the odd grunt every once and a while. Though he remained relatively silent, that didn't mean that Kent wasn't enjoying himself, rather he simply wanted to enjoy the sounds his lover made. They were just so cute, and the soft plap of their bodies meeting was oddly hot, the pony’s soft flanks conforming around the human’s more muscled crotch.

The sound of someone grumbling temporarily diverted the human’s attention towards Diamond Tiara who sat slightly closer then where she had been a minute ago. Though her attention was still mostly fixed on the window, she was glancing over to the pair nearly constantly, a hoof hovering over her own visibly soaked privates. Kent shot her a smirk, an action that prompted Diamond Tiara to scoff, and look away while not removing her hoof.

Chuckling to himself, the human turned back to the main attraction, namely the perfectly plump posterior before him. Fixing his grip, Kent eagerly got right back into the action while idly noting that his next orgasm was rapidly approaching. A feeling he seemed to share with his lover as Diamond Crown’s moans had grown louder, and even higher pitched over the last few seconds.

Not wanting his pony lover to have to do all the work, Kent thrusted a little harder, and generally put a bit more effort into his actions. Which paid off almost immediately when Diamond Crown’s next bounce faltered somewhat, his legs shaking briefly. A second later and the tremor was gone, the pony returning to the same pace he had a moment earlier. He wasn't sure how, but Kent knew that he didn't need to hold back for much longer, as Diamond Crown wasn't far from finishing.

He briefly marveled at the pony for being able to take that much pleasure from getting fucked in the ass. That just made things better in the human’s mind, as it meant that he didn't have to worry about feeling too selfish when they had sex. Those were considerations for another time however, right now he was too focused on the simple feeling of plowing tight pony butt to think of anything else.

All that existed were the expertly trained internal muscles of his artificial lover and the way they massaged his length with such perfect precision. It was almost better than Diamond Tiara’s pussy, though Kent couldn't say for certain which one was better, or even if one was more pleasurable. Either way the human didn't care to rate them in the first place and was more than happy to simply enjoy the ride he was receiving.

A ride he knew would be coming to an end soon enough, as he noticed a tremor building in Diamond Crown’s right leg. Sure enough, it wasn't long before the pony began to orgasm, his moans becoming so high pitched that they were even more girly than Diamond Tiara’s. That didn't mean he stopped riding his human lover however, as even though his cock was spurting white jets across the couch, still Diamond Crown continued to bounce away.

Kent wasn't far behind though, and just when he drew close to finishing, his fingers dug into the pony’s flanks. Pulling the pony down hard against his crotch, the man forced Diamond Crown to remain there as he began to shoot his load deep into the othe male’s ass. Together they moaned long and hard, though Kent’s was muffled while the pony all but screamed his pleasure at the top of his lungs.

The human’s entire body remained tense as the seconds ticked by and he continued to paint the pony’s insides with his seed. Just like before, he came harder than he thought possible, absolutely emptying himself in Diamond Crown. Who was hanging his head low and taking short breaths between soft, half muffled moans.

The pony’s orgasm died relatively quickly while Kent’s went on for much much longer. Eventually it too ended, the man relinquishing his hold on the pony’s ass and sprawling out onto the couch, a wide grin on his face.

“Fuck that was good,” he muttered.

Diamond Crown grunted as he wiggled each of his legs in turn. “Damn stud. It feels like you damn near filled me to the brim.”

The human chuckled. “It sure felt like I did. Great job.”

“No thank you,” Diamond Crown retorted. “I’m fairly certain I spent everything I had.”

“Yeah yeah, you were both great now let me have a turn,” Diamond Tiara demanded, stomping up to the pair.

Kent blinked. “Err right now?”

“Yes right now,” Diamond Tiara stated, tapping a hoof impatiently as her counterpart slowly rose. “I have to prove my ass is better.”

“Well I…” Kent glanced at the pony’s backside, and after noting it was nearly identical, decided not to fight it. “-don't think there is any harm in that. Just give me a good thirty seconds to get going again.”

“Excellent, now get out of my way!” Diamond Tiara barked.

“Yeah yeah, hold your horses,” he muttered.

Diamond Crown grunted as he awkwardly hoisted himself off of the human cock which had impaled him, cupping a hoof under his backside in order to keep from spilling. He then maneuvered his way off the couch before trundling out of the room, making his way towards the bathroom.

Now alone with his other pony lover, Kent watched as she grabbed a cloth and wiped away the remnants of her counterpart’s orgasm. With that done she tossed it at the hallway, and quickly hopped atop the couch, mimicking the same position Diamond Crown had taken. Before he had a chance to warn her that he wasn't ready, she sat just below his cock, allowing it to rest in the cleft between her cheeks.

The human’s eyes went wide, a grin slowly crossing his features.

“Fuck thats good,” he muttered as Diamond Tiara slid his cock between her ass cheeks.

“So hot stuff, ready for more?” she teased, flashing him a wink over her shoulder.

The man hummed, and hawed while slowly growing hard once more. “You know what? Yeah. What's the worst that could happen right?”

“I’m getting next right after that!” Diamond Crown shouted from the other room.

“Quit trying to ruin this for me!” Diamond Tiara yelled back.

“Hold on a second,” Kent cautioned, only now realizing what he may have accidentally started. “Lets not go crazy. After this I’ll need a break.”

“Sure sure, you’ll get your break. Now get ready for the ride of your life,” Diamond Tiara exclaimed.

The human gulped.


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