This story features Jack and Maddox from Deep Under. Although it can be read as a standalone, it will be more enjoyable if you’ve read Deep Under. Please use the Jack&Maddox tag to see all Jack & Maddox epilogues.
Maddox watched the video, his cock rising lazily in response to it as Jack finished toweling off. Jack tossed the towel into the hamper and gave him a hopeful look.
“No point getting dressed,” he confirmed. He was still naked himself, stretched out in bed with his head elevated to see his tablet. On the screen, a dark-skinned twink was getting fucked by a light-skinned bear with a full beard and impressive guns. Maddox’s attention was mainly on the bottom, who was nowhere near as hot as his own big, masc, thoroughly submissive guy, but he did have something that’d been attracting his attention of late.
“What are you watching?” Jack lay down next to him, curling into him and hooking his chin over his shoulder to see the screen. Maddox knew the exact moment he noticed the cage on the twink’s dick, because he went very still and his cock, which had been floppy-but-interested a moment ago, started trying to drill a hole through his thigh.
“Is that something you’re thinking about doing?” Jack asked, a little quaver in his voice that he cleared with a strangled cough.
“Locking your cock up?” It did have a certain appeal. At any rate, he’d been enjoying videos that featured cock cages lately.
He owned Jack’s cock, and they both knew it, but it was out of his reach for a good portion of every day. Maddox didn’t suspect Jack of disappearing into the men’s room of the FBI offices to have a quick wank, but the fact was that he could. There’d been limits on what he could impose on Jack during Jack’s undercover days, but he had a desk job now. If he was wearing a cage—a cage only Maddox had the key to—it wouldn’t be anyone’s business except theirs.
“Maybe,” he answered, stringing Jack along for now. “Does it appeal to you?”
Was that a no-really no or a no-please-make-me no? He checked on Jack’s expression and decided it was a no-but-I’d-do-anything-for-you no.
“I like your cock.” He gave it a squeeze. It was good and hard, nearly dripping. “I like it best when you’re so turned on, it turns purple.”
“Then why are you watching that?”
“It’s another form of chastity play. Look at this guy who’s getting fucked.” He held the tablet under Jack’s nose as he continued to give him a rough wank with his other hand. “Does he seem into it?”
Jack squirmed in his grasp as he looked longingly at the screen where the twink really did seem into it, except for the fact that he wasn’t hard. The twink wasn’t hard because he couldn’t get hard, because the cold metal cage didn’t allow it, and Maddox wasn’t sure whether that did it for him or not
“Here, watch this.” He handed Jack the tablet, then got between his knees and took him into his mouth.
“Oh God,” Jack groaned. “Why?”
“What’re you complaining about? Most guys would love having their tops go down on them.”
“I do love it.” Jack clenched the tablet as if it might leap out of his hands, but his eyes weren’t focused on it. “Except you only do it when you want to torture me.”
Maddox laughed. It was so true. “Don’t come,” he warned as he sucked him back down again.
“See? Fuck, Maddox, please?”
Maddox grinned around Jack’s cock, but he didn’t stop what he was doing. Unrelieved pleasure was always the best way to get Jack to really beg, and his dark, sadistic heart loved hearing Jack beg. Would he beg the same way if his cock was locked up so tight that he couldn’t come? They might have to find out.
Don’t blow, don’t blow, don’t blow. That was all Jack could manage as Maddox tortured him with his mouth. For a guy who gave very few blowjobs, Maddox knew what he was doing. Or maybe it was just that he knew Jack, knew exactly how to use his teeth and fingernails—pressure and pain mixing into pleasure—to hit all his buttons. And all Jack could do was lie there and take it, keep his hips still and his eyes on the video Maddox had ordered him to watch.
The video wasn’t helping. Because what if that was him? What if Maddox did want to lock his cock in a cage? Jack would say yes, of course. He’d say yes to anything. And he’d hate having his dick caged and love that he hated it and love Maddox all the harder for making him love this thing he hated, and he didn’t know if he could stand to love Maddox any more than he already did.
The very first time they’d ever played together, back when he’d been undercover and Maddox hadn’t even known his real name, Maddox had fucked him and walked out on him, left him hard and unsatisfied. But as soon the door shut behind him, Jack was taking care of himself. The denial had been no more than a matter of minutes. Now that they were in bed together every night, Maddox sometimes left him riled up for days, and Jack rarely jerked off to relieve the pressure. He enjoyed Maddox’s power over him, but it was a choice he made. What if he didn’t have that choice?
He groaned at the thought. His mind was his own worst enemy right now—right behind Maddox’s tongue. Why Maddox thought he had this kind of willpower, he didn’t know. He always ended up begging Maddox to stop, so anxious about accidentally disobeying him that the pleasure cascading through his body was just another form of pain. That was why he should have a cage, why he should be locked up and never allowed to come and—
Oh God, he did want it. And he was so fucking close. “Please, sir.” He reserved the word sir for moments of true desperation, a sort of signal. Like yellow, except for being too wound up to resist any longer.
Maddox lifted his mouth off his cock, giving it a last swipe that sizzled like fire along his shaft. “Hand me one of those cock rings.”
Jack fumbled through the drawer on his nightstand for a cock ring.
“Not that one.” Maddox shook his head at the ring Jack extended to him. “You know what I want.”
He’d offered the one Maddox wore to keep himself extra hard, hoping Maddox was about to fuck him. But no, it was still torture on the table, apparently. He sorted through the drawer again and found the ring Maddox sometimes put on him, the one that was so tight he couldn’t come in it.
“Yeah, you do know what I want,” Maddox said when Jack handed it to him. He hitched his body higher up the bed and gave him a lingering kiss. “How’d I get so lucky?”
“How did I?”
Maddox grinned, and somehow Jack found the strength to grin back, despite knowing things were about to get really bad.
“What else?” Maddox asked himself with a calculating look in his eye. “The prostate massager, I think. No, the manual one. I’m not in a hurry.”
Jack closed his eyes as a shudder ran through him. Yeah, it was going to be bad.
Maddox manhandled Jack’s cock and balls into the ring then rotated around so that his groin landed temptingly close to Jack’s face. “I’ve got a deal for you. Make me come, and you get to come.”
“Really? All I have to do is make you come?”
“Twice. Did I forget to say twice?”
Jack thumped his head against the bed with a groan. Maddox never came twice. His favorite post-orgasm thing to do was go to sleep with his hand wrapped around Jack’s still-hard cock. There was no way Jack was going to win this battle, but the fact that he wouldn’t be getting off tonight didn’t dim his enthusiasm for getting Maddox off.
He ditched the tablet and reached for Maddox’s cock. This was his talisman, his favorite cock in the world. If he could only have one cock in his life, he’d choose Maddox’s over his own. And wasn’t that what a cock cage was? The subjugation of his pleasure to his master’s? Pleasing Maddox was his sexuality.
He set to it, trying to focus all his attention on the warm column of firm flesh in his mouth but unable to ignore the hard plastic massager working at his prostate with a rocking rhythm that mimicked Maddox’s mouth on his shaft. He wished it was Maddox’s cock up his ass even as he relished having Maddox’s cock in his mouth. Basically, he wanted Maddox’s cock everywhere, always. And if he didn’t get Maddox to come soon, he was going to lose this challenge by coming before he’d even made Maddox blow once, never mind twice.
Maddox didn’t do cocks up his ass, but he would sometimes take fingers if he was in the mood for it, so Jack slicked up one hand and worked it behind Maddox’s balls to tease at his rim. When Maddox didn’t redirect him, he went deeper, probing with two gentle fingers at Maddox’s prostate until Maddox started moaning. He was always so stoic, but prostate stimulation loosened something in him that made Jack’s heart tender and his cock hard. He focused his tongue on the sensitive underside of Maddox’s cock and felt the tingling pressure that meant he was about to come. He opened his throat to accommodate the bucking thrust of Maddox’s hips as Maddox took over the rhythm and found his own climax.
Jack swallowed, continuing to suck even as the stream dried up. If he was going to get Maddox off again, he’d need to keep him hard.
Maddox swatted the back of his head. “Stop.”
“How am I supposed to make you come then?”
“Not my problem.” Maddox rolled onto his back, brushing Jack off his body. He gave his softening cock a reassuring squeeze, then heaved a big yawn. “I’m ready for bed. How about you?”
Jack could accept it—lie down to sleep in that nebulous state between emotional satisfaction and physical dissatisfaction—but he had a feeling Maddox would be disappointed if he did. He hadn’t suffered enough, not in the way Maddox had been looking for. And thoughts of hard cocks and cold metal cages, not to mention the fact that he had a ring wrapped around his junk and a prostate massager crammed up his ass, had him turned on enough that sleep wasn’t going to come easily. He had a day job now. Maddox couldn’t just leave him lying awake half the night in a state of frustration, though he doubted that argument would work. Maddox wouldn’t mind that he was suffering. Maddox liked him suffering. In fact…
“No,” Maddox answered before Jack could finish the sentence. He quirked an eyebrow, suggesting it was Jack’s move.
“I’m so fucking horny. What if I…?” He moved a hand to the massager Maddox had left buried in him.
Maddox raised both eyebrows this time. “You’re going to fuck yourself?”
“If you’ll let me.”
Maddox crossed his arms behind his head. “Turn around. Ass up.”
He rotated himself so he was on all fours, pointing his ass with the massager extending from it right at Maddox’s face. This was going to be easier than he’d expected.
“Don’t touch your cock,” Maddox warned.
Right. He should’ve expected that. He lowered his chest to the bed and reached for the massager, but it disappeared from his ass.
“Use this.” The dildo Maddox put into his groping hand was a big one. The blue monster, Jack guessed from the ridges. It had a tapered head and widened toward the base. Too big to be a butt plug but meant more for stretching than prostate stimulation. Jack could sometimes come hands free, but there was no way he could do it with this thing. And if he asked Maddox to take the cock ring off, Maddox would only laugh.
But the point wasn’t to come. He didn’t have permission to come. The point was to get Maddox to come. So he gave himself up to the embarrassment, leaning into his desperation, letting everything he felt tumble out of his mouth with unusual abandon—how fat the dildo was, how it hurt even as it felt good, how it came nowhere near giving him what he needed, how turned on he was and how badly he needed to come, how ridiculous he felt fucking himself for Maddox’s amusement, how he knew Maddox was getting off on his suffering, and how he loved him for getting off on it.
Maddox was getting off on it too. Jack could sight under his arm past Maddox’s knobby knees and sturdy thighs to the growing length of his cock, which Maddox had absentmindedly begun stroking. His strokes sped up as Jack moaned and groaned as if he were close to coming, pleading with Maddox for permission, which only made Maddox snicker and move his hand faster. When Jack could tell from the sound of his breathing that he was almost there, he spun around and dove for Maddox’s cock, fastening his mouth over it to suck for all he was worth. Maddox thrust into his throat, caught up in the rush of his orgasm.
His second orgasm.
Maddox slumped back onto the bed, letting the force of his climax drain the tension from his body. He didn’t know whether to be angry or impressed.
“You conniving bastard.”
“All’s fair,” Jack said with a smirk. “You owe me now. A deal’s a deal.”
Maddox didn’t welch on his deals, but he wasn’t letting Jack off easy either. If he did, Jack would only be disappointed.
“Just for that, you’re coming with the ring on.”
“This ring?” Jack wrapped a hand around the base of his cock where the tight silicon ring had him beautifully contained. “No way. I can’t.”
“Oh, trust me. You will.”
When Jack shivered, the dildo crammed up his ass eased its way free with a wet plop.
“Go clean that up, then get back here. I thought someone wanted to get to sleep early tonight, but no, apparently we’re doing this.”
“We don’t have to, Maddox.”
“But we do, babe. We really, really do.” He shooed Jack into the bathroom, taking advantage of his absence to lay out his tools. Prostate massager. Nipple clamps. Lots and lots of lube. All that desperation Jack had just faked in order to wind him up? He was going to mean every bit of it by the time they were done.
When Jack came back to bed, he made him lie down on his back and hitch his legs up.
“Hold those good and tight for me, babe. No interfering.”
Jack gave him a look like he would never dream of interfering, but he’d never been told he could come and then not given enough stimulation to get the job done before. Usually Jack was trying to resist his orgasm, not chase it, but Maddox made him chase it now, holding the massager still and making Jack undulate his hips to work himself on it, tightening the nipple clamps only enough to tease, leaning down now and then to give a lick or a nibble to a nipple or a cock.
How long had Jack’s cock been this hard now? It strained in its bonds, the tip exactly the shade of purple he’d been dreaming of when they started. Looked like he’d gotten his way after all. He grinned at the thought, and Jack gasped.
“What are you thinking about?” Jack asked.
“How much I like fucking with you. You’re gorgeous when you suffer. Five more minutes.”
“Until what?” The fear in Jack’s voice made Maddox grin harder. His man knew him too well.
“Until time runs out on this offer. Come now or come never.” There was a good chance it’d be never. The video that had started this whole thing flashed through his mind, and now he had no doubt he loved it. Jack coming never. Hard and hurting and wanting him. Always.
Jack’s gaze was pinned to his face. Maddox didn’t know what he saw there, but apparently he found the stimulation he needed because his eyes rolled back and come started oozing from his cock in long, slow streams. Drizzly, but endless. Maddox could have been a bastard about it, but he wasn’t. He took over the rhythm Jack’s hips had abandoned, scraping the massager against his prostate until the come stopped flowing and Jack started screaming. Okay, maybe he was a bastard.
“Fuck, Maddox. Please?” Jack held up his arms, and Maddox dove into them, cradling his guy who was flush from his climax and decorated with nipple clamps and streaks of come, who still sported a prostate massager sticking half out of his ass, and who was doing something that was almost crying.
“Shh, babe.” He removed the nipple clamps, then fished out the massager and went into the bathroom to clean it up. When he came back out, Jack’s tears had dried, but he was still soft-eyed and soft-bodied. Maddox rolled him onto his side and curled around him.
“Sorry I don’t have a hard cock for you to hold tonight,” Jack said.
“Hard or soft, it’s still mine.”
“Am I getting a cage?”
“I think you know the answer to that.”
A soft noise somewhere between a groan and a sigh slipped from Jack’s mouth—maybe at the thought of a cage, maybe because Maddox had just wrapped his hand tight around his balls. Either way, he was asleep in a moment, leaving Maddox to nuzzle into the back of his neck and give thanks to whatever miracle of fate had made this possible.
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