Archive of Our Own

“ Jay- ” Kai yelps, though it was far from a sexy sound. The two of them sitting on the bed, Jay trying to get his fingers inside Kai who squirmed uncomfortably. 

“Hold on- hold on, just give me a second-”
“Dude- it hurts!”
“It can’t be that- OW!”

Kai’s foot made contact with Jay's face, it wasn’t a full on kick, but enough to have Jay reeling back.

“You kicked me!”
“It was a reflex, I told you it hurt!”
“Sorry..” Jay whined, looking up with lube slicked hands and an apologetic smile; Earning an exasperated sigh from Kai.

“It’s okay but the mood is kinda dead and my ass hurts,”
They’d tried a few times now, they thought with Jay being smaller it’d be easier for the two. But they were both new to well- being gay. So neither had a lot of information about how anal worked in real life. 

Kai was quick to learn porn was not realistic. Especially when Jay tried to just push right in. Ouch.

For now, they’d mark tonight as another failure. Opting to instead just cuddle until dinner time. 
It was at dinner when Jay had the idea. Sitting across from Cole, his best friend. His gay best friend.

“Cole, I need to talk to you.” Jay asked after dinner, trailing behind the black ninja and shutting Cole’s bedroom door behind them.

“Sure, what’s up?”
“Can- or, would you fuck Kai?”

The silence in the air is absolutely suffocating.

“What? Like in general?”

It took a lot of rambling for Jay to finally explain the issue they’d been having, Cole going between flustered to giggling to actually taking the request seriously. 
Admittedly, he’d always had a thing for Jay and Kai. (And Zane. Most handsome men really.)
But in the past, he assumed they were straight, then they came out and Jay and Kai started dating, so Cole just assumed they weren’t interested in him.

And well - they haven’t confirmed if Kai was interested. And going to Cole first might have been a little backwards, but eventually Jay was peeking into Kai’s room.

“Kai?”
“Mh?” The brunette lazily answered, glancing up from his phone.
“I have a… proposition.”
“Go on?”

The door fully opened and Cole was there too, Kai raising an eyebrow at the duo. 

“What did you two do?”
“What? Nothing!”
“You look guilty.”
“It’s not- no, I just. Would you be open to uh- because you know how we’ve been having issues with personal time and-”

Cole finally cut in. 

“He asked if I could help you guys with anal,”
Kai’s face very quickly turned a bright red. Embarrassment and soon anger reflecting in his expression.

“You asked him what? ”
“I thought he could help!”
“Are you stupid? You didn’t think to ask me first?”
“I- okay yeah I just- Cole’s our friend! And he’s done this before, and I don’t want to keep hurting you!”

The last part made Kai hesitate, as annoyed as he was - Jay was trying to help. And they admittedly weren’t getting very far on their own. 
Cole was also… very hot.

“Fine.” Kai spit out, because while it made sense, he could still be a bitch about it.

“Really?”
“Really.”

Now that the lovers had stopped fighting, Cole moved to sit down on the bed.

“So..?”
“Wait- now? ” Kai exclaimed.
“If you don’t want to-”
“No no, just uh. Jay?”

Kai looked over to Jay, who perked up - locking the door before launching himself besides Kai. Bouncing against the mattress, pressing a kiss to Kai’s cheek before settling. 

“Yes- Yes I’m ready. I’m down. Teach away, Cole.”
Lube was still sitting out from Kai and Jay's earlier attempt, so Cole grabbed it and warmed it idly in his hands.

“How about you take off your pants, hot shot. Whatever is comfortable.” The nickname made Kai flush further, it wasn’t uncommon for the team to throw around nicknames but this felt more… intimate. 

Comfortable for Kai ended up with him pantless, but still wearing a shirt, with a pillow in his arms and holding it to his chest as Cole settled between his legs.
Cole had to stop himself from staring, Kai’s thighs looked soft - a comfortable layer of fat over the toned muscles below. Not to mention how cute his cock looked, resting limp for now.

“I don’t know how you’re gonna do any better, your fingers are huge.” Kai grumbled, earning a giggle from Jay - but Cole only hummed in acknowledgment, squirting lube on his fingers.

“Starting out, don’t press in.” He explained aloud, narrating as he began his work

“You need him relaxed, he’s too wound up like this - it’ll hurt. Just gently tease the area. Maybe press the tip of your finger in a little but don’t force it.”

True to his word, Cole was far more patient than Jay had ever been.
A large finger rubbing lube against Kai’s rim, Kai having to resist squirming under the attention, let alone the way Cole spoke - Kai didn’t exactly have the best view to watch so hearing what Cole was doing was surprisingly hot.

He didn’t even notice that Jay for once in his life was being silent, just watching Cole’s fingers intensely. Cole could almost imagine Jay writing what he was saying down on a clipboard with the focus he showed.
Turning his attention back to Kai, he smirked as Kai let out a soft moan that was quickly muffled by his pillow.

“There we go,” Cole cooed softly, watching Kai’s cock respond to the teasing touches.

“To help him relax, it’s good to touch , too.” His free hand sliding up Kai’s thighs, feeling the smooth skin before wrapping around Kai’s length. Stroking him slowly to coax a full erection.
Kai’s face was soon pressed into the pillow he held, struggling to keep any other sounds contained as Cole worked. 

“Now that he’s relaxed and used to the feeling, start working gently in. Just little bits -  Kai can you look up at me?”
Kai really didn’t want to, but he looked up. Flushed and breathing heavy, biting back a low moan at Coles encouraging smile. 
Finally a finger began to press deeper, just the tip. Slowly fucking in and out, leaving a layer of lube to allow the next thrust deeper.

“Watch his expression. Go slow. Use plenty of lube.” The larger boy continued, looking far too calm considering the situation.
It was only then Kai noticed that Cole had, somehow, managed to work an entire finger inside him. The soothing touches to his skin and teasing strokes to his cock helping to distract him from the finger pressing and pulling inside him in strange ways. 

Strange, but not bad.

“Holy shit Cole,” Kai groaned lowly, Jay nodding numbly in agreement. He couldn't help but think how nice they looked together. 
At some point, Jay had slipped a hand into his pants, palming himself as he totally listened to everything Cole was telling him. He was listening, just- Kai was making such sweet sounds it was getting harder to focus. 

“Repeat the same as before, but with another finger. Work slowly until they fit.” 
Two fingers, two fingers. Just one felt massive to Kai, but the second one seemed to stretch him further than he thought possible. Previously, just one of Jay's fingers was too much. 

“The next part is the fun part,” Cole’s own breath was a little heavy now, pulling his fingers out until only the tips were still inside Kai’s stretched hole. His other hand held up to mirror what the other hand was doing. 

“Start near his entrance, and curl your fingers.” The fingers inside Kai and the fingers hovering in front of Cole curled.

“Massage gently along the top, work back slowly until-”
“Oh fuck- ” Kai suddenly gasped, his voice cracking as Cole found something good inside him.

“There it is, good boy.” 
“Oh-” Jay said softly, arousal practically dripping from his voice. 
“His prostate?” Jay asked, earning a proud nod from Cole.

Large fingers curled and scissored, Kai’s eyes hazy as they switched between watching Jay full on jerk himself off next to them and Cole’s lidded expression. 
Jay was absolutely not listening now, palm sliding along his own arousal with whiny breaths as he watched his best friend turn his boyfriend into a mess.

The thick digits began to move again, a shallow thrusting motion that had Kai’s toes curling into the sheets, his body struggling not to squirm as he practically clawed at the pillow he held. Pathetic whines he’d never made before being fucked out of him with every slick thrust. 

Cole’s fingers were moving faster now, the squelch of lube sounding out with every hard thrust. Echoed quickly by a moan or whine from Kai.
The red ninja's voice bouncing with the enthusiastic work from their teammate, he didn’t even notice when Cole somehow managed a third finger - too focused on the livewire running through his veins. 

“He looks so good like this,” Jay panted, Cole nodding as he scissored his fingers with a lewd noise. 
He’s taking this better than I expected,” Cole admitted, eyes glancing over to Jay’s cock. It was just as cute, a pretty pink head and wow did Jay leak. Cole still had the lube next to him, so the slick mess Jay was using was definitely precum.

“You could probably fuck him now,” Cole adds, his fingers slipping out with a shlurp that had Kai burying his face into the pillow again.

“What about you?” Jay asked, confusion creasing his brow while Cole’s raised in surprise.
“What about me?”
“Well- I mean, you helped so- isn’t it only fair?”
Cole giggled at Jays consideration, but only shook his head. 

“I think I’m a little too big.” He explained, Jay rolling his eyes.
That was until Cole unzipped his pants and- wow.
His cock was thick, curved and uncut. Not to mention large, If he somehow got that in Kai there’s no doubt it’d be visible through the boys stomach. 

“Holy shit Cole, that’s practically a third leg.”
“Mh chhl shh hih ouh.” Attention turned to Kai, who’s words were inaudible through the fabric of the pillow.
At the other twos’ blank expression, Kai sighed, putting the pillow to the side.

“ᴵ ᶜᵒᵘˡᵈ ˢᵘᶜᵏ ʰᶦᵐ ᵒᶠᶠ…” Still, Kai was too quiet. Gritting his teeth at the fact he had to use his words, he hated words! But he also was hard as hell and not being touched so he snapped.

“ I could suck him off!”  
That… wasn’t a bad idea. Kai had gotten pretty good at giving head, Jay still had a horrible gag reflex.

“I- you don’t have to, Kai.” Cole tried, suddenly having a pillow thrown in his face.
“You had your fingers in my ass, don’t give me that ‘you don’t have to’ shit.” Kai snarled, though there was no real venom behind it. Especially as he glanced away shyly and admitted.
“Also I want to.”

Cole couldn’t argue with that, honestly, he didn’t want to. The idea of Kai’s hot mouth on his cock was a wet dream.
Especially on all fours - wow, if Cole wasn’t hard before he would be now. 

They’d all stripped at this point, it just seemed easier. Kai looking up at Cole with those pretty eyes while Jay fiddled with the lube behind him. 

“Lube yourself up first, then push in slow.” Cole instructed, grinning when Jay saluted at him before following instructions.
Kai pawed at his cock suddenly, Cole gasping in surprise.

“We- we should wait until Jay is, so you don’t choke-” Cole whined, Kai’s warm hand stroking him slow. 
“Can’t choke on a handjob,” Kai purred, continuing his work before Jay tapped his ass.

“Pushing in,” He informed, and pushing in slow and steady. Extra lube on standby as he rocked slow into Kai’s ass.
And oh. Kai was so tight. And hot. And- and pretty? It was hard for Jay to think as he pressed deeper into the red ninja who in turn sucked in a breath, eyebrows pinching in pleasure at the fill. 
Jay’s hips pressing against Kai’s ass, both boys momentarily still as they processed the feeling. Cole wishes he could take a photo, the blissed out faces of them both in front of him made him throb in Kai’s hand.

That seemed to get Kai’s attention, burning eyes fluttering up to meet Cole’s gaze. Kai leading Cole forwards until he could wrap his mouth around the tip of Cole’s cock.
He couldn’t take much, just a couple of inches (which was still surprising to Cole) but made up for that with the way he worked the rest of the length with his hand. 

Turns out, Kai was really good with his tongue. Then he moaned around Cole - the black ninja letting out an open moan at the same time as Jay, who had apparently started moving. Shit - Cole’s brain was not working with such a hot tongue toying with the head of his cock.

Jay took the earlier instructions to heart, thankfully, working his hips slow and steady. Whining as he grabbed at Kai’s hips.

“Oh- Kai, you feel so good ah , thank you- thank you, Cole.” Jay moaned, his hips beginning to speed up, a passing thought in Cole’s head being how Jay looked like a horny rabbit. Passing, as Kai moved to squeeze his balls as he took more of his length. Apparently having warmed up enough to take at least half of it.

“Oh Kai,” Cole sighed, feeling the way Kai whined and moaned around him, he looked down to find a sight that almost had him cumming there and then.
Kai was flushed, teary eyes as he mostly used his hand to toy with Cole’s cock. His jaw slack as he rocked with Jay’s thrusts, Rubbing the underside of Cole’s arousal with his tongue.

Jay now leaning over Kai’s body, Kai’s moans turning whiny as Jay’s arm reached around. Stroking Kai in time with his needy thrusts, the two of them were a very attractive sight. Jay hadn’t stopped mumbling praises for both of them, stuttering and gasping into incoherency as he must’ve reached his limit inside his lover.

His hand never stopping where it stroked and toyed with Kai’s cock, grinding deep as Kai wound tight, Cole had no doubt if his mouth wasn’t filled he’d be nearly screaming as his climax overtook him. 

He couldn’t resist, reaching down to brush the hair out of Kai’s face to which the red ninja nuzzled him. 
Somehow that got to Cole the most, head thrown back with his own deep moan as his hips jerked. His load filling Kai’s mouth without warning, hell, even Cole didn’t get a warning as his cock throbbed with his finish. 

Once his brain was functioning again, Cole was quick to get up - finding a towel and the water bottle on the nightstand. He even brought over tissues and the trash bin, the plasma pair still pressed against each other. Cole having to coax them to move, Cole gently pulling Jay’s hips so he at least wasn’t still using Kai as a cock warmer.

The two of them very cuddly, somehow warning Cole’s chest and leaving a weird ache.
Whatever - aftercare first. Grabbing a tissue he held it out for Kai.  

“Spit,”
“Huh?”

There was a pause.

“Did you… swallow?”
“Tasted good,” 
“Oh, good to know.”

Next was wiping them all down before folding the towel under Kai’s hips, Cole working while two sets of eyes watched him contently. It wasn’t until Cole handed them the water bottle and stood up that Jay spoke.

“Where you going boulder brain?”
“Well- I uh,”
“C’mere,” Kai added, reaching up for Cole.
He wasn’t… expecting this part. Sandwiched between his two teammates, he was expecting the sex but the cuddles was a nice bonus. The kiss he received from Kai was also a very nice bonus.

“Huh?” An elegant reply to be sure. One that made the two brunettes giggle, Jay pulling COle down for his own kiss. 

“Why’d you do that?”
“Because we like you?” Jay added, confused. Making Cole fumble.
“Oh!”
“Stupid.” Kai muttered, resting his head against Cole’s shoulder. 
“”M sleepy now. We can talk more later.”
“Yeah- yeah I’d like that.” 

Gay best friend? Nah, gay boyfriend now.