Chosen One, 100

For Some People, Penetration Is the Most Comforting Act There Is

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Spencer had been hammering Isaac for nearly a full hour now, his cock unrelenting as he pounded in and out of Isaac’s ass, and Isaac held his arms, legs wrapped around Spencer’s middle, not letting Spencer get away with letting up for a second. “Come on,” he said. “Harder, harder. Skip wants you to go harder, doesn’t he?”

“Yeah,” Skip agreed, masturbating breathlessly on the bed by Isaac’s head, watching Spencer go with undivided attention. “Yeah, go harder, Spencer, come on.”

Spencer nodded and, like he had every other time he’d slowed down and risked letting Isaac think, he found the energy and started fucking Isaac even harder. His face was all sweaty and so was the rest of him, and it was a really good look for him. His hair was painted to his forehead and he was shining all over in the low light and his cock was so impossibly hard inside Isaac. He pressed his lips to Isaac’s and kissed him fiercely, so strongly he almost cut Isaac’s lip with his tooth, and Isaac kissed him back just as hard because he wanted it, he wanted all of Spencer.

And for just a minute he had him, until Skip said, “Spencer, Spencer, I’m going to…” And then Spencer’s attention was back on Skip where it should be, and Isaac was happy to give him up. He lifted up, still fucking Isaac right into his mattress, and turned his kiss on Skip just as Skip started to cum, coating Isaac in another load.

They kept kissing until Spencer was cumming too, slamming into Isaac while he and Skip swapped moans. Skip’s balls were in licking distance and not licking them was so hard, but Isaac managed it, watching them move and imagining them in his mouth, imagining tasting them and sucking on them and hearing Skip’s noises as he did it, and Isaac didn’t need Spencer’s hand as it came down to touch him, he was already cumming too.

Spencer lay on top of him and Skip beside him, and they held each other in place there for a bit, looking up at the ceiling. “I love you guys,” Isaac muttered, as his brain started to work again.

“Yeah, we love you too,” Skip said, kissing Isaac’s cheek. It was nice to hear it. He never doubted it, but hearing things that made him feel good was helping Isaac a lot. Doing things that made him feel good was helping a lot. Being honest with himself about what he wanted was helping a lot, and right now he wanted sex and affection in that order. “And that was pretty awesome, we’ll have to do it again.”

“Yeah,” Isaac agreed. “Now?”

Spencer laughed, letting his dick slip out of Isaac so he could lay on his side. Isaac hadn’t been joking, and Spencer’s still-hard dick seemed plenty serious too. He ran his finger through the cum collected on Isaac’s chest. “I probably have another one in me, but we should get cleaned up. But maybe we could do it again in the shower room?”

Isaac’s dick jumped. “Okay,” he said immediately. “Let’s go.” He got up, prompting laughter from the two of them. Spencer climbed down the ladder, and Skip leapt off the bed, and they kissed at the bottom as if just being reunited, the tips of their dicks kissing as well, and it was really cute. Isaac watched them for a second before climbing down.

When he was halfway down the ladder, Skip turned and suddenly licked a line of Spencer’s cum from the inside of Isaac’s thigh, all the way up to his hole, and he dipped his tongue inside, licking around it for a second before stepping back. “Hm,” he said. “Not bad.”

“It’s better than not bad,” Isaac assured him, feet hitting the floor. “You should taste it again.”

“Nah, cum tastes weird the more loads you’ve shot in the day. Maybe in the morning when it’s fresher.”

“That makes no sense,” Isaac said, trying not to laugh. “Nothing changes the taste of cum.”

“Fruit does,” said Spencer.

“No,” said Isaac. “Trust me, I’ve blown guys who ate a lot of fruit and it didn’t do anything.”

“Oh.” Spencer blinked. “Huh.”

“Maybe I’ll be willing to test that, after Spencer’s done with you in the…” Skip looked over as the door opened, and there were Peter and Nicholas, damp, naked, together, and both hard. “Oh, we may have to reschedule that.”

“Yeah, sorry,” said Peter, coming into the room. “We’re going to pull the boyfriend card and steal him from you. Hi.” He kissed Isaac deeply, and Isaac kissed him back, hands running down Peter’s back, cupping his ass.

“Hi,” Isaac said, out of breath. Nicholas pulled him over, claiming his mouth in another kiss, hand on the back of Isaac’s head. “Oh, hi.”

“Hi,” Nicholas agreed. “Peter and I had a long talk in the shower just now.”

Right. Right, the talk. Isaac had forgotten that, but it was important. “It went…well?”

“Yeah,” Peter said, giving a smile. “We agreed that we both love you and the best thing we can do is stay out of each other’s way for a while. But starting tomorrow, because tonight we both want to fuck you. And for your sake, we’re not taking turns.”

Oh. Isaac felt himself warm right up. “Okay. I appreciate…”

“Don’t,” Nicholas told him, finger over Isaac’s lips. “You don’t have to appreciate us, we love you and we want to do something nice for you.”

Isaac smiled, sat down on his bed, getting them to sit on either side of him. “Okay, well I appreciate you anyway, so there. Sorry, Spencer, Skip. Next time.”

“Next time,” Spencer agreed, waving as he and Skip left. They shut the door behind them, which was fine.

Isaac wasted no time in taking their hands in his, kissing Peter, then Nicholas, then Peter, then Nicholas, letting them kiss him on his cheeks, his neck, his messy chest when they weren’t on his mouth. “It makes the most sense,” Peter muttered around Isaac’s nipple as Isaac made out with Nicholas. “For you to be on bottom with him riding you.”

“Yeah,” Nicholas agreed, moving to kiss Isaac’s collarbone. “And you on your knees behind.” They were talking past him like he wasn’t in between them, which was turning Isaac on more than it had any right to. Nicholas lay on his back and pulled Isaac onto him, smiling up at Isaac. “Does mean you won’t get to kiss him.”

“You’d be surprised what I can do.” Peter was between Nicholas’s legs on his knees, hands on Isaac’s sides. It was a good position, Isaac thought. He’d trained them well. He kissed Isaac’s shoulders, letting Nicholas kiss his neck, all of them moving closer together, Peter and Nicholas repositioning Isaac together so he was raised up, above Nicholas’s dick. He heard a cork pop and oil was poured down his back, down to his hole, on Nicholas’s dick.

With Nicholas pressed at his hole, they held him there, and Isaac started to move down, stopping when Peter’s hands tightened on his waist. “No,” said Nicholas. “We talked about who would get to go inside you first. And we decided you could take both of us.”

Isaac tried to smile and ended up gasping just a little as Peter’s cockhead pressed against Nicholas’s at his hole. “I didn’t expect you’d be working together so well,” he muttered, every part of him twitching in anticipation.

“Fighting hurts everyone, you and us,” Nicholas said. “And nobody wants that.”

“And we know you’ve been feeling crappy,” Peter said, with another kiss when Isaac tensed. “Hey, it’s okay. You can tell us why when you’re ready. But we want to take care of you. We thought about taking turns fucking you and having you pick who was best, but we thought that would stress you out.”

“You guys are the best fucking boyfriends,” Isaac said, idly wondering where Jacob was. He’d been at the academy for an hour or so but then left before supper.

“No,” said Nicholas.

“You are,” Peter agreed.

They pushed into him together then, two cocks entering Isaac’s ass at exactly the same time. “Ah!” It stung but not in a bad way and Isaac sank into it, lowering himself down onto both their cocks as they thrust up, not quite in time with each other but close enough, stretching him instantly.

It may have been a lot but Isaac was more than ready for both of them, and even together they slid in without too much trouble, each getting a little over halfway in before getting stuck and having to stop and kiss him again. Then they started thrusting, not together, both trying to hilt themselves in Isaac, and Isaac let them do it, holding onto Nicholas’s shoulders, feeling Peter’s hands on his hips, Nicholas’s on his arms.

For all that they were trying to work together, Nicholas and Peter totally failed to set up a good rhythm between them, moving irregularly as they both tried to fill Isaac to the best of their ability. But it didn’t matter because they kept kissing him and touching him and holding him and they were whispering his name and other stories at him, fucking him deeper and deeper.

And when they both did it, first Peter and then Nicholas giving big thrusts, Isaac sliding the last bit downwards, both of them fully inside him, Isaac cried out a sound that could have been a combination of their two names as he came all over Nicholas’s chest. “Feels good, hm?” Peter asked, stroking Isaac’s nipple from behind.

Isaac nodded, no room left for words anymore, but that was okay. “Keep, keep going.”

“We will,” Nicholas said, moving. And then he got going, and Peter got going, and they were finally moving together again, and the room fell into that loud quiet that happened when everyone was breathing and sweating and concentrating on sex, doing their best to make each other feel good.

And then the door opened. “Oh,” said Jacob’s voice. “Hi.”

“Hi,” Isaac said, looking over at him. He was standing there with Leo, who was naked and holding his clothes, and also Jacob’s. “Hi, Leo.”

“Hi,” said Leo, staring. “I…guess I’m interrupting?”

“Not at all,” said Peter, smiling at him. “We’re helping Isaac feel better.”

“Leo was in the neighbourhood after I found him at work and suggested he should come to be in this neighbourhood since Isaac was feeling down,” said Jacob, shutting the door behind them. “I hope that’s okay.”

“Of course it’s…okay,” Peter grunted, giving a thrust. And then another. “Fuck, Isaac…” He gave one more and then started to cum, twitching as he filled Isaac’s ass. “Fuck.”

Isaac nodded, gesturing for Leo and Jacob to come over. “It definitely is,” he said, giving Jacob a kiss. “It means a lot to me…Nicholas, fuck, fuck…”

“Yeah, yeah” Nicholas agreed, moving harder, taking Isaac’s words away again as he started moving faster for a good minute, everyone else going quiet as they watched. “It’s nice to meet you, Leo,” he finally managed to pant.

“You too.” Leo smiled. “I guess you guys already have cheering Isaac up covered.”

“They do,” said Isaac, pulling Leo closer. “But seeing you also makes me feel better.” He kissed him. “Thanks for coming.”

“Here,” said Peter, pulling back. “One of you can slide in here if you…”

“No,” said Isaac, swallowing as he looked at Jacob’s dick. “No, Peter. I think Jacob can fit in there with you and Nicholas.”


“Isaac, are you sure?” asked Jacob.

“Holy shit,” Nicholas said, as he exploded inside Isaac, cock throbbing hard.

“I’m sure,” said Isaac. “Come on, no more speeches about how you don’t want to hurt me, I know you don’t so I know you won’t.” Jacob liked to worry about things, but Isaac really wanted this, so he put all his want into his voice. “Please, Jacob? I want all my boyfriends inside me at once.”

“Well…how am I supposed to say no to that?” Jacob asked, grabbing the oil and getting ready.

Peter moved so he was penetrating Isaac from the side a little bit, giving Jacob some room, and though it was awkward, Jacob was very receptive to Peter’s quiet instructions and was more than nimble enough to get in there, sliding his dick up with Peter and Nicholas’s. Leo sat on the bed beside them, watching raptly, hand on his dick.

“I’m ready,” Isaac said, taking a deep breath.

Jacob grunted, stroking Isaac’s hair, and he pushed, widening Isaac even further. Isaac gasped loudly, feeling the sting more acutely now, but he transitioned into a whinge as Jacob slid further in, wanting him all the way. “Isaac…”

“Goddamn,” Peter said, hand on Jacob’s back now as Nicholas held Isaac steady. “Goddamn, Jacob.”

Isaac nodded, eyes shut, but only for a second. “Hey, Leo?”

“Yeah?” Leo asked, voice distant.

“I know we don’t know each other super well, but I really like you and I was wondering if maybe you wanted to be my boyfriend too.”

Leo swallowed, audible even over everyone’s breathing. Isaac had been watching his stomach because it was hard not to, and he saw the exact moment he held his breath. “If…if that’s okay with all of you I’d really like that, yes.”

“Of course it’s okay with us,” grunted Nicholas. “Isaac dates who he wants.”

“And he makes good decisions,” Peter added, reaching down and adjusting Nicholas’s dick a little.

“And if you make him happy then we like you too,” Jacob confirmed, voice strained.

“Okay. Okay. Then yeah, of course I’ll be your boyfriend, Isaac.”

“Great.” Isaac kissed him, slowly and for a good minute, before pulling back with a smirk. “Let’s figure out a way to get you inside me too.”

“I don’t…see how that’s even…”

“If we…come at him from four sides,” Peter said, holding Isaac tight. “If we put his legs up to his shoulders…”

“Yeah,” said Jacob. “Yeah, that can work. Like this contortionist I saw once. Here, like this.” Nicholas handed Peter one of Isaac’s legs and Jacob the other, and then held onto his thighs. Nicholas sat up and got on his knees, and the other three did too, cocks together. Isaac was folded in half, holding himself up off the bed by the slats under Spencer’s, supported by everyone, and it was already so great.

And there was just enough room for Leo to slide in there, shaking, and work his dick into the space between Jacob and Nicholas. And he started to push inside.

Jacob whinged and came as soon as Leo was pushing, and that distracted Isaac for just a second from the flash of white pain that seared across his whole body. He remembered it hurting the first time he’d taken two, and it hurt even more now, but Isaac held his eyes shut and rode through it, knowing it would get better. It wouldn’t always hurt, and he wanted this so much, it was the best thing he’d ever done and four people who loved him were doing it for him, so he knew it wouldn’t hurt for long.

And it didn’t, eventually it didn’t. The pain stopped and then all Isaac could feel was all four of their hands on his body, all four of their breath on his neck, his face, his back. All four of their cocks in his ass, moving at different paces. Leo was most of the way in. Someone was cumming. Nicholas, Isaac thought.

Leo clung to Isaac’s left arm as he pushed in, and Isaac could feel, not in his asshole but in the energy of the room, the moment when he was all the way there, when his balls were fully touching the others and when all of Isaac’s boyfriends were fully inside him where Isaac wanted them. Isaac nearly screamed as he came this time, the orgasm on the bright side of painful as all of his feelings coursed out through his dick. There were tears in his eyes but they were good tears, they were perfect tears, because this was a perfect moment.

They were all four of them still inside him for a minute, two, and then Leo started to move again, hesitantly, and the others followed. Isaac felt Dark and realized that he’d let go of Spencer’s bed a while ago and Peter was holding him up with it, helping them all stay in place, and they all moved together now, not in tandem yet, but together, one group with one goal.

Leo came too, yelping Isaac’s name as he did, and Peter shot again with him, whispering love in Isaac’s ear. Neither of them stopped or even slowed down, just going and going and going and Isaac didn’t have to do anything, they just held him up and fucked him and touched him and loved him and Isaac felt safe, and he wasn’t thinking about Cameron or liars or centipedes or anything, just love and the four of them.

He lost track of who was cumming inside him, they were all cumming, they were all happy. At one point, they paused, all five of them panting together, Isaac’s legs resting on one of Nicholas’s shoulders and one of Leo’s. Isaac felt so full and…no, nothing else. Just love and fullness. “I love you guys,” he said, voice cracking. He thought he might be crying. “I love you guys so much.”

“We love you too,” Peter promised, kissing Isaac’s mouth.

“We love you too,” Jacob agreed, stroking Isaac’s hair.

“We love you too,” said Nicholas, forehead resting against Isaac’s.

“We love you too.” Leo was cradling Isaac’s side, clearly with no intention of letting go. “You let us take care of you all night, okay?”

“I will,” Isaac said. He’d tell them why he was upset, he would. He had to. But in the morning. For now, he just closed his eyes, let the people who loved him hold him, and surrendered to that full feeling and that feeling of overwhelming, unconditional love.

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