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When It Suits

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“Are you sure you wanna try this?” Arin looked nervous as Jack smoothed down the skirt that Suzy had picked out for him.

“He did say he wanted to try,” said Suzy, and she was crouching in front of the two of them, wearing a calculating expression. “Now… are you ready, Jackie?”

Jack nodded, biting his lip.

“I need you to use your words, baby girl,” Suzy said, in a voice that was a bit like butter - it was enough to make Jack’s toes curl.

“I’m ready,” Jack said.

“Who are you ready for?”

“... you, Daddy.”

“Good girl,” said Suzy. “How about you and Arin lie back on the bed, so Daddy can get you nice and ready?”

Jack nodded.

“Yes, Daddy,” said Arin, and he reached out, grabbing for Jack’s hand.

Jack squeezed Arin’s hand.

Arin squeezed his back.

Jack got up on his elbows, looking down, and there was Arin’s cock, all wrapped up in its nice metal cage.

He’d first discovered it when he and Arin had gone beyond occasional awkward making out during late night Grump videos, and Arin had left a wet spot in his pants, but didn’t have a boner.

There had been some… assumptions, and then some surprises, and now Jack was almost used to seeing Arin’s cock wrapped up in the metal.

Jack licked his lips.

“I was thinking of something special for my special girls,” said Suzy, and she held up another metal cage.

Jack licked his lips.

This was a trial run.

She’d let him out when they finished their scene.

But first… he had to put the thing on.

“You ready, baby girl?”

Jack nodded, shy.

“What are you ready for?”

“I’m… I’m ready for the… you know, for you to do the… thing.”

“Who are you talking to, Jackie?”

“Daddy.”

“What are you ready for, Jackie?”

“... Daddy, I’m ready for you to… to lock me up.”

“Such a pretty little thing, too,” said Suzy, and she was carefully placing his balls through the ring, then sliding his cock through the cage.

She placed it in the cage, then locked the cage with a “click” that was very… final.

“There we go,” said Suzy, and she stroked Jack’s tummy, pushing up Jack’s dress a bit more.

Jack squirmed, biting his lip.

His dick tried to get hard.

That was… that was uncomfortable.

“Now,” said Suzy, “we don’t want you to get too drippy, do we?”

“Drippy?”

“What does Daddy tell you, baby girl?” Suzy was directing her speech towards Arin.

“Daddy tells me that… babies with their cocks drippy like that, they have to be nice and padded up,” said Arin.

“... right,” said Jack, as Suzy got the diapers out.

They were pink.

They were very, very pink.

They even had little bows printed onto them.

“Lift your hips up for Daddy, Jackie,” said Suzy, and Jack’s hips were up, his feet planted flat on the bed, his caged cock cold against his thigh, already beginning to warm up from the heat of his body.

Jack lifted his hips until he was settled down on the cushy softness of the diaper, his legs being forced apart as Suzy pulled it up between his legs. She taped him in, and his caged cock was surrounded by the softness, by the plushness, by all of the warmth, his legs forced open.

He was still on cloud nine when Suzy was talking to Arin, cooing at him, about he was being such a good girl for Daddy.

And then they were both done, and they were the both of them sitting on the bed, diapered, in dresses, and there was their Daddy, standing in front of him, her hands behind her back, a smirk on her face.

She was wearing a suit, and she looked heavier about the crotch than usual.

“Now,” said Suzy, crossing her arms, moving to sit at the chair by the window, “are you gonna be good girls?”

“Yes, Daddy,” said Arin.

He elbowed Jack in the side.

“Yes, Daddy,” Jack parroted.

“Entertain Daddy, why don’t you?”

“Uh….” Jack’s arousal was enough that his cock was trying to swell in the cage, and he was drooling even more. “I’m not so good at tap dancing.”

“... what?”

Suzy burst out laughing, and Arin gave Jack an odd look.

“Make out with Arin,” Suzy said, when she could breathe again. “And make it look good.”

“... oh,” said Jack, and he blushed, dark red. “Um. Right.”

He turned to kiss Arin, and Arin cupped his cheek, leaning in to kiss Jack back.

They kissed sweetly, and Arin moaned theatrically.

“That’s so nice,” Suzy simpered, “but if I wanted to watch that kind of thing, I’d watch network television. Make it more interesting.”

Arin grabbed Jack by the hips, pulling the smaller man into his lap. He wrapped his arms around Jack’s middle, and he kissed Jack like he was in a porno, grabbing Jack’s ass through the diaper, pulling their crotches together, beginning to grind them together.

Jack whined - he barely got any stimulation, but it was… it was better than nothing, and then Suzy was sitting next to them, Suzy was putting her hand on his hip, Suzy was watching the two of them as he kissed harder, as Arin’s tongue stroked along his own, Jack’s own hands moving to Arin’s chest, kneading the soft skin.

“Play with Arin’s tits, Jackie,” said Suzy, and she sounded like she was moaning. “Show Daddy those lovely, lovely tits.”

Jack unbuttoned the front of the shirt with nervous fingers, and he squeezed Arin’s chest in both hands, pressing the palms of his hands against Arin’s nipples.

“Look at that,” said Suzy. “Look at those lovely, lovely titties.”

“They’re a pretty awesome pair of tits,” said Jack.

“Suck on them,” said Suzy.

“Yes, Daddy,” said Jack, and he leaned forward.

* * *

Arin moaned and wriggled, humping against Jack’s mouth, still sucking, flickering his tongue along the tip of Arin’s nipple, nipping around Arin’s nipple, then sucking it hard enough to pull off with a “pop.”

Arin was squealing, whining, wriggling, his hands tangled in Jack’s hair.

“Fuck, please,” Arin gasped. “Please, can I… please?”

“Can you what, sweetie? What’s my baby girl want from Daddy?”

“I want… please… can I come out of the cage, please?”

“No,” said Suzy sweetly, and Arin sobbed.

This felt like it was part of the game.

“But… if you’re a very good girl,” Suzy said, “maybe you can take Daddy’s cock.”

“I’ll take it,” Arin said quickly. “Please, Daddy, give me your cock.”

“What about you, Jackie?” Suzy prodded Jack in the side.

“I’ll… I’ll do anything Daddy wants,” Jack said, a bit dazed.

What was he gonna do?

“You wanna suck Daddy’s cock, baby?” Suzy cupped his cheek, thumbing his cheekbone, her skin so soft against his scruff. “You wanna wrap those pretty dick sucking lips around me?”

Jack blushed, from the roots of his hair to his neck, and Suzy smiled.

Arin laughed, not unkindly.

“Y-yes, Daddy,” said Jack. “I’ll… I’ll get it ready for you, Daddy.”

“Such a good girl for Daddy,” Suzy cooed, scooting a bit so that she could sit on the bed and lean against the wall. “Now… gonna make it nice and wet for Daddy?”

“Yes, Daddy,” said Jack, rolling onto his belly and crawling towards her.

His dick, still trapped in the diaper and the cage, was squished, but… pleasantly so.

It was strange.

* * *

Jack had sucked cock a few times.

We all have our own lives, our own misadventures.

But sucking Suzy’s cock was odd - it was colder, without any of the regular heat that Jack was used to, and it didn’t leak out anything particularly interesting.

In some ways, it was as exciting as sucking a hunk of silicone really can get, because, well… it didn’t pulse, it didn’t get any wetter.

But Suzy moaned like he was sucking on a piece of her, and that was worth all its weight in anything.

Especially when Arin joined him, crowding in closer, so that he was kissing Jack over the silicone cock, deep, hard, porn star kissing, and Suzy had a hand on each of their heads, and was moaning like she was being paid for it.

“That’s what I like to see,” Suzy cooed, and her sharp little fingernails were digging into Jack’s hair, as he slobbered up and down her cock, as Arin moaned against him, holding his hand tightly, using their hands to jerk off Suzy’s dick.

Jack was grinding against the bed, which didn’t do much good, but he was also sliding a sneaky finger into Suzy’s harness, under her slacks, and she was smirking at him, as he began to stroke her clit with the very tip of his finger, looking up at her through his eyelashes.

“You know,” said Suzy, “I think that Jackie should have a chance getting fucked by Daddy’s dick. She hasn’t had a go at it yet, after all.”

Arin nodded, breathless, although he looked a little disappointed.

“Aw, are you gonna feel neglected, baby?” Suzy patted his cheek, and her painted fingernails looked dark against his pale, flushed skin. “How about… while I fuck her, little Jackie gives you oral?”

“What about the nappies?” Jack burst out.

“We’ll take it off first, dumbass,” Arin said, in a tone of good natured ribbing.

Jack blushed, but he prodded Arin in the side.

Arin prodded him back.

“I was gonna let you have a regular blowjob,” Suzy said casually, as Arin kept giggling, “but since you decided to be a brat, I guess some caged oral it is, huh?”

“Wait, no, I -”

“Too late,” Suzy said sharply, and she slapped him on the hip. “Lie flat.”

“... yes, Daddy,” said Arin.

Jack grinned, a bit confused, but enjoying himself.

* * *

Arin’s diaper was pushed down, and maybe Suzy had been planning this more than Jack had thought, because she hadn’t powdered Arin at all.

He stayed on his tummy, between Arin’s spread legs, and he took the head of Arin’s cock into his mouth, sucking on it through the metal of the cage.

The sensation was… odd.

Cold metal, with the hot, desperate flesh poking between.

It reminded him, absurdly, of being a child and wrapping a rubber band around and around his finger, although where had that come from?

Then his own diaper was being pulled down in the back, and a gloved, lubed finger was being slowly slipped into his ass.

… good thing he’d skipped lunch, it appeared.

“Such a good girl for Daddy,” Suzy said, her voice quiet, as she began to thrust her fingertip in, carefully.

Jack tried to relax into it, tried to put all of his attention of making Arin feel… something.

Judging by the noises that Arin was making, it wasn’t exactly… good, per se, but he was most definitely feeling something, judging by the noises he was making.

When Jack glanced up, his expression concerned, Arin gave a slightly haggard thumbs up, and he smiled at Jack.

“It’s… a tease, but I like it,” he told Jack, his voice rough. “Please don’t stop.”

“My baby girl likes her special treat?”

Suzy’s finger was all the way inside of Jack now, and it was curling, carefully.

“Y-yeah,” said Arin. “Unless… you were talking to Jackie.”

“I was talking to both of you,” Suzy said, “but I know Jackie’s a good girl and would never talk with her mouth full.”

Jack snorted, hard enough that he had to take his mouth of Arin’s cock and cough a few times, catching his breath.

Suzy rolled her eyes, pressing closer to him, her soft breasts warm against his back through her white button down shirt, her small hand on the back of his head, forcing his face into Arin’s crotch.

“Keep at it, Jackie,” said Suzy.

“Yes, Daddy,” Jack said sweetly, and he wrapped his lips around Arin’s caged cock and sucked, hard enough that Arin jerked forward, knocking the lock against’s Jack’s front teeth, which… ow.

In contrast to sucking Suzy’s silicone cock, this was… very drippy.

Jack’s mouth was flooded with pre, and he was drooling it out, down his chin.

He was bobbing his head, awkwardly fondling Arin’s balls, and Arin was still squirming under him, breathing heavily, his eyes sliding shut.

Suzy’s finger found that one good spot inside of Jack that made his hips hunch forward, his cock spitting out pre, which was absorbed into the diaper.

Maybe that was why she liked to diaper boys - she didn’t want to deal with all of the gunk that would end up pouring out of their dicks.

Jack whimpered around Arin’s cock, which made Arin groan, humping awkwardly into Jack’s mouth, trying to be careful of the metal.

“There we go… there’s my baby girl’s g-spot, isn’t that nice?” Suzy’s voice was sickly sweet, and it was making Jack’s cock throb harder.

It was already getting warm and stuffy inside of the diaper, and the cool air on his ass was nice - the second lubed up finger was nicer, if a bit of a stretch, and he groaned, letting go of Arin’s cage to suck on his balls, which made Arin groan harder, his toes curling into Jack’s ribs.

“Oh my god,” Arin gasped, and he was shaking, more pre dribbling down his shaft, puddling on his groin.

He was going to need to wash the whole mess of it, very soon.

Jack was going to need his own bath soon, probably.

But right now, he wasn’t going to worry about that.

He sucked on Arin’s balls, licked the heated flesh from between its metal confines, then took it into his mouth again, as Suzy’s third finger slid into him, more of a stretch than he was used to, but he had a feeling he could become very used to it, very quickly.

It was… it was good.

It was toe curling, eyes rolling in the back of the head good, and if he wasn’t caged, he probably would have cum already.

The pent up heat in his gut was already building - his cock was leaking so much prostate fluid, his legs were shaking, going tense, then turning to jelly.

“Oh, sweetie, you’re so tight for Daddy,” Suzy crooned, and she pulled her fingers out of him.

Jack made a disappointed noise, trying to get hump back against nothing.

“Oh, I see,” Suzy purred. “My baby girl is eager, isn’t she?”

Jack nodded frantically, still humping against nothing.

And then the blunt, thick head of her cock was pressing against his hole, and he went still, as she slowly, carefully slid in.

It was so slick, so tight, that it made him pause in his ministrations, to just lie there and feel it, panting, his forehead pressed into Arin’s sweaty thigh.

“You okay there, buddy?” Arin’s voice cut through.

“Mmm?”

“You’re kinda seizing up,” Suzy supplied, still barely in. She was using her regular voice, not her Daddy voice.

“I’m… okay,” Jack said. “Just, uh… intense.”

“It’s all good, sweetheart,” said Suzy, stroking his back through the dress.

Arin pushed Jack’s hair off of his forehead, and he grinned at Jack.

“You’re doing great,” he told Jack.

Jack nodded, still panting, getting used to the feeling, his cock cushioned by the thick diaper, his heart pounding in his ears.

“Okay,” he said, after a few minutes. “I think… I’m ready.”

“I can keep going?”

“Yeah.”

“Good girl,” said Suzy, and she did indeed push further forward, until she was fully seated in him, and Jack groaned, as she swiveled her hips and pressed down on something… good inside of him, his prostate probably, and his cock twitched in the cage, or at least tried to.

He clenched around her, and he wrapped his mouth back around Arin’s cock, the cage clacking against his teeth as he humped shallowly back into Suzy.

“Oh, look at Daddy’s eager little girl,” Suzy said, and then she was… she was holding Jack’s ass open, oh no, she was watching her rainbow cock split him open, then slide almost all the way out, then slide back in, oh god, it was so… it was so depraved, and he was in a diaper to top it all off, to make it even worse.

Arin was moaning, and the pre in Jack’s mouth was coming faster, as Jack rubbed along Arin’s taint, trying to find that one good spot that stimulated the prostate.

And then Arin bellowed like he had just been shot, and Jack grinned around the metal in his mouth, because he’d found it.

“You okay, baby?” Suzy sounded genuinely worried.

Arin gave her a thumbs up, and Suzy giggled and gave a nice, hard thrust.

Jack groaned like he was dying - the pressure in his gut was getting unbearable.

And then… it was like he was cumming, except he wasn’t.

There was a lot more goo flowing out of his cock, and his ass was twitching, but because he wasn’t hard in the technical sense of the term, it was just… spasms going through him, without any of the lovely heat, pressure, or friction that would come from an orgasm into, say, a hand, or a nice firm pussy.

So he shook and he whined, then went still, letting go of Arin’s dick, drool dripping down his chin.

“I think baby girl is worn out,” said Arin, his voice rough.

“How about you, sweetie?”

“I… could use a break,” Arin admitted, grabbing between his legs and squeezing gently. “Can you take me out of the cage after the scene?”

Suzy grinned and shook her head.

“No, sweetie, we agreed, one month, remember?”

Arin gave an exaggerated sigh, but he was grinning.

“Oh well.”

“Now,” said Suzy, “which one of my sweet little girl’s is gonna get me off?”

“Daddy?” Jack’s voice was tired, but he smiled at her. “Daddy, will you sit on my face?”

“You want to lick Daddy?”

Jack nodded eagerly.

He’d just barely gotten a chance to touch her pussy, and he wanted to give it a… much closer inspection.

Suzy was kicking off her harness, wriggling out of her pants, and now she was crouching over his face, and Arin was shifting his own position, and Jack’s head was resting on Arin’s thigh, as Suzy’s weight rested on his sternum.

He pressed his face upwards, and he tasted paradise.

* * *

He could hear the sounds of Arin and Suzy making out, and the occasional moans she’d give.

When he slid his finger inside of her and curled it, she didn’t just moan, she clenched around him, her muscles strong and tight around the digit, beginning to grind down on his face.

She wasn’t just whimpering anymore, those were full throated “I’m being filmed” moans, and Jack grinned, wrapping his lips around her clit, then beginning to lap at her hole, sliding his tongue in, slurping loudly.

She came across his face in a gush of fluid, and it was almost as wet as when he had been sucking Arin.

Arin, whose cock was drooling down his collarbone, onto his chest, soaking into the dress.

Suzy flopped down on the bed next to him, panting, and she laughed, clearly light headed.

“I think… I’m done being Daddy,” she told Jack.

He gave a thumbs up.

“Do you want to keep the cage on?”

He shook his head.

“How about the diaper?”

Thumbs up.

“Can you talk?”

He shrugged.

Arin kissed the top of his head, and then he was being wrapped up in big, strong arms, while Suzy held onto his other side, kissing his temple.

“It’s okay,” Jack said. “I’m okay.”

“I know,” Suzy said. “But you’re small and you’re cuddly.”

“I’m not that small!”

“You’re smaller than me,” Arin said, and he kissed Jack’s head.

“... can I get out of the dress?”

“In a minute. Enjoy the moment.”

Jack snorted - even when she wasn’t being a Daddy, Suzy was… kinda bossy.

But he closed his eyes, and he did his best to follow instructions.

He liked to be good like that, when it suited him.