Double client

A/N: This one is loooong and pretty much just sex xD

“Shikamaru, your next client is a double.” The boy looks up at the words, getting up from his sprawled position on the couch. The clothing he wore was a simple net top and a small leather jacket, loose shorts clothing his legs. He stretched, the black netting etching itself onto a surprisingly toned front.

“Alright.” He began heading towards his room, wondering who the two were. Normally, in this kind of business, you only get customers one at a time. Most people were ashamed of coming to a whore house, especially those looking for a male entertainer.

He knocked before entering.

“He looks a bit scrawny.” The first words to land on the Nara’s ears weren’t unusual. Most of the time when they came looking for a man, they didn’t picture someone as small of frame as Shikamaru. Though he had grown a bit from his constantly mistaken for underfed frame, he wasn’t the most built male in the place.

“You were the one to set the criteria, Jiraiya.” A smooth voice said from the side. Shikamaru’s eyes drifted over, seeing a shorter, younger man. While the first to speak had long, thick white hair, this one sported thinner black tresses. Both wore their hair in a ponytail at the base of their skulls. The black haired male let his bangs frame his face.

Both had unbelievably thick hair, even when compared with his own brown ponytail.

“Hey, you little Uchiha punk, all I asked for was an experienced guy with some muscle and stamina.” The first one, Jiraiya, snapped even as his eyes began raking up and down Shikamaru’s body. Shikamaru smiled lazily, which turned out to appear soft and inviting to others. Go figure.

“We will see how experienced he is.” The other one, not yet named, stated. His own eyes took in the younger male, though not as wolfishly as his companion. Shikamaru relaxed under their gazes, keeping himself open and inviting while he let them talk.

“I hope to please you both.” He spoke into their lull, giving them his soft, lazy smile again. Jiraiya seemed to be falling for it, a grin spreading across his features as his eyes began to sparkle. The other remained silent, giving off the air of watching and waiting.

“How exactly would you please us both?” Jiraiya asked, advancing a few steps. Shikamaru remained where he was, tilting his head to look up at the taller man, ignoring his plain looking slacks and top and downright scruffy appearance. The rules of the house were to pay before hand, additions charged after the fun.

“Any way you want.” Shikamaru replied. He’d learned from other entertainers not to give specifics so soon. If he had said one thing when Jiraiya was thinking another, he could turn the man off. Who was to know if the white haired male was a prude or a pervert?

“He’s smart.” The black haired male said, eyeing Shikamaru more critically now. Shikamaru tilted his lips, just barely; accenting his olive toned skin and almond eyes. The man smirked.

“Itachi, I think it’s time we get down to business.” Jiraiya said, finally revealing the name of the black haired male to their entertainer. He swiftly pulled his shirt over his head, tossing it to the floor. Shikamaru was surprised by how tan and muscular this Jiraiya was. He’d been expecting something more pudgy and…old trying to be young. Not actually succeeding.

“Always the rush.” Itachi said, not removing his clothing. Jiraiya turned to him, grinning lecherously.

“Why not rush? I paid for sex, not chit chat.” He advanced on Shikamaru, reaching out and tugging on his small jacket. Shikamaru moved so that he was still facing Itachi with Jiraiya at his back, undressing him further.

“Would you like me to undress you, Itachi?” He asked, making a point to keep his laziness and the minimal excitement growing in his abdomen in check. Soft words, neutral tones. At least until they made it clear what they wanted.

The man seemed to consider, sweeping dark orbs over the smaller males now exposed torso, watching as the large tan hands began massaging at Shikamaru’s stomach and chest. He smirked lightly, nodding.

“I would.” Shikamaru gave him the inviting smile he’d been using, stepping away from an obviously disappointed Jiraiya. The older man huffed at Itachi, crossing strong arms over his bared chest, pouting.

“I’ll be back, Jiraiya.” Shikamaru said over his shoulder, tilting his lips for the man before turning back to Itachi. He didn’t catch the way Jiraiya’s eyes gleamed, moving down to mentally grope and fondle his ass.

Itachi held still, seeming almost serene as he watched Shikamaru reach down, unbuttoning his silken black shirt from the bottom. The other’s hands were dangerously close to his awakening member, snaking away in an almost teasing fashion as he followed the buttons up. At the top, after undoing the last button, he slid both hands under the soft cloth and began pushing it back and off the pale shoulders, skimming his fingers and palms over Itachi’s soft skin as much as he could.

Jiraiya could feel his cock twitch just from the sight. Their entertainer’s skin looked so good, so exotic, against Itachi’s. The soft way he touched the Uchiha made the older man immediately fantasize about those hands on his shaft, lavishing soft and dark and exotic all over his nether regions.

The sight of the other was almost too much; kneeling down, his back flexing in a way that made Jiraiya want to lick all along the ridges and valleys his muscles and bones created, sliding Itachi’s pants and boxers down, looking up at the Uchiha as he exposed the man. Jiraiya could just see it in his exotic doe eyes, the question shining softly with the dark sin of what he wanted to do with the erection bobbing so close to his lips.

Jiraiya couldn’t keep the grin off his face.

“As much as I would love to see what you’re oh so perfectly poised to do, I’m more of a doer then a watcher.” He spoke, rubbing a hand against the bulge in his pants. Shikamaru stilled, tilting his head to view Jiraiya over his shoulder. The motion was dead sexy to the old pervert, curving the others back while he was still on his knees, his mouth open in a small ‘o’ as he breathed, eyes asking in just that darkly exotic way he’d imagined they would.

He suddenly remembered he didn’t even know their entertainer’s name.

“What’s your name, anyway?” He asked, rubbing a little harder as his arousal increased from the sight displayed before him. He nearly groaned as the others lips curled deviously, turning around and slowly climbing to his feet.

“Shikamaru.” He said, voice deep and husky as he stepped forward. He moved Jiraiya’s hand, replacing it with his own, rubbing in a softer, more teasing manner. The older man shuddered.

“Shikamaru, huh?” He nearly panted the name. The boy was good with his hands, stroking and petting through the material of his pants in a way that was just delicious. He didn’t even notice Itachi until the man was behind Shikamaru, pale hands slipping under the waistband of their entertainer’s shorts. “Well Shikamaru, we have a lot in store for you.”

Jiraiya could feel when Itachi grabbed Shikamaru, the boy’s own hands stilling, a slight spasm twitching through his fingers.

“I think it’s time we undress Shikamaru…” Itachi whispered, nibbling lightly along the boy’s ear. Jiraiya nodded, reaching out and tugging at the shorts. Shikamaru’s hands resumed to what they were doing, petting through the cloth. Before he could slip his hand up to the waistband and down, Itachi’s arms were around his bared waist, his hands grasping his wrists.

Shikamaru turned his head slightly, giving Itachi a questioning look. The Uchiha bent down, giving the other a light kiss, sliding his hands down until he had intertwined their fingers. He moved their hands up then, hooking into the waistband and pulling down until Jiraiya was fully exposed.

“Gods Itachi, his skin looks so dark compared to yours…” Jiraiya said, lips moist from his hot breaths and wet tongue, watching as Itachi bent again, biting and sucking at Shikamaru’s neck. He moaned when he felt Shikamaru’s palm touch his base, the Uchiha’s fingers still woven in as they both began to stroke.

While doing that Itachi brought the other hand back, beginning to do the same to Shikamaru’s own hot member. He pressed forward, his erection nudging at Shikamaru’s ass, causing the boy to moan, pushing back.

“Fuck Uchiha, you trying to make me cum early?” Jiraiya asked, moving his hips with the stroking. His hands lifted to Shikamaru’s front, tweaking a nipple and caressing a stomach, enjoying the feel of him under his fingertips.

The Uchiha remained quiet, pushing Shikamaru forward until the boy’s leaking cockhead nuzzled into the older man’s, drawing sounds from both of the males.

“You are, you little cocktease.” Jiraiya panted. He lifted his hands away from Shikamaru, pushing at Itachi’s hands, stepping up to the boy they’d paid for. Jiraiya’s lips attacked his neck, his ear, his lips, all while pushing him back towards the red blanketed bed, the headboard accented by smooth metal bars twisted into an intricate shape.

Itachi was the first to lay back, moving just until his ass was at the edge of the bed. Shikamaru looked behind him, following Jiraiya’s lead as the man continued nudging him where he wanted.

Shikamaru was just fine with this type. The kind of customers who knew what they were doing and not constantly asking him if he’d do this, or would he do that. What he hated most were the customer’s who asked him personal questions.

They knew he would do whatever they wanted, that’s what they’d paid for and what else was there to it?

“Shikamaru spread your legs wider.” Jiraiya instructed, bringing him out of his musing. He found that while he’d been dazing out Jiraiya had managed to direct him onto the bed, legs straddling Itachi’s ribs while he was suddenly looking at the ripe fullness of the Uchiha’s cock. He swallowed, his tongue licking at his lips involuntarily.

Itachi had a beautiful cock.

He wouldn’t have needed a paycheck to lay lips to what he was being presented with. Slipping his eyes up to where Jiraiya was standing, looking them over, conversing with Itachi though he hadn’t been paying attention, Shikamaru was met with another gorgeous example of manhood.

His back arched as a slick finger was suddenly pushed into him, the long pale finger brushing near his sweet spot as it began stretching. He kept himself still, tremors running along his thighs as a devilishly sweet tongue began lapping up the trickle of pre-cum, the finger soon joined by another, pumping in and out.

“Oh now that’s inspiration…” Jiraiya said, appreciating the sight thoroughly. Shikamaru closed his eyes, enjoying the feel of Itachi’s tongue and fingers before he bent down, suckling the tip of the man in return. He felt him tense under him and suckled harder, eyes still closed. His hands began massaging at the man’s thighs, kneading the soft flesh under his palms.

Shikamaru jerked, suddenly feeling a delicious pressure on his cock, something massaging him in the center of Itachi’s tongue, making him quiver and whine around the Uchiha’s length. He could hear Itachi’s soft chuckle, feel it vibrate the muscles of his throat that were now around him.

The motions, if anything, made the tongue stud the Uchiha sported rub into him even more, causing still more of the little wanton sounds from Shikamaru. The boy’s ears were ringing in pleasure, leaving him unable to hear encouraging sounds from the white haired male despite his close proximity.

Soon a hand was in his ponytail, stilling his actions and drawing his attention back.

“Alright Shikamaru, ready for some action now?” Jiraiya said with a laugh. Shikamaru sat up, crawling forward and moving to get off the bed. Jiraiya shook his head, motioning for him to stay where he was, straddling the Uchiha’s stomach. He felt Itachi’s hands at his hips, holding him there as the man relaxed back on the bed.

“Just sit tight now, Shikamaru.” Jiraiya instructed. He moved up, aligning himself with Itachi’s opening. Shikamaru’s eyes opened wide, the question obvious in his expression. Jiraiya laughed again.

“Your eyes were closed when I was stretching him.” He explained, sliding in. Itachi tensed under Shikamaru’s thighs, his hands tightening as Jiraiya situated himself.

“Fuck, you never get any looser…” Jiraiya breathed, his eyelids rolling down in a rapturous sigh. Itachi murmured something in return, flexing his thighs as he wrapped them around Jiraiya’s waist. He pushed at Shikamaru’s hips, nudging him towards Jiraiya, who brought him closer with one hand at the small of his back.

“This’ll be good.” He said, lifting Shikamaru almost bodily, the boy barely needing to help as he was positioned over the Uchiha’s angry red cock. He licked his lips, feeling the slick head nosing at his entrance. He lowered one hand, gripping Itachi’s hot shaft and guiding it inside faster, gasping lightly at the feeling.

“Just move like you would normally.” Jiraiya said, helping to hold him up by placing a hand at his lower back. The other one he placed at Itachi’s hip, keeping him down as he began to thrust gently, allowing a rhythm to be set.

“F-fuck…” Shikamaru panted out, unable to keep it in as he began moving along Itachi’s cock, feeling the way Jiraiya’s increasing thrusts moved the body beneath him. Jiraiya smirked at him, bending down to lay a searing kiss on his lips, caressing with his fingers at Shikamaru’s back.

Shikamaru kissed back, moving faster now, one hand going to his unattended shaft and stroking at a faster pace than he was moving on Itachi. Jiraiya made a noise that sounded like a moan, thrusting faster, letting go of Itachi’s hips and grabbing Shikamaru’s cock for him.

The older man swallowed the low needy moan that followed, growling his approval and moving his hand faster, hips snapping forward and driving deeper and deeper into Itachi. He was rewarded with his increased vigor by hearing an arousing and oh so carnal sound from the male he was piercing, almost eclipsed by Shikamaru’s pleasured purring of his own name.

Eventually one of them couldn’t stand it, clenching around the hot shaft within him and gripping tight to the one riding him, body stiffening as another low-pitched sound rumbled from his chest. This created a domino effect, Jiraiya swallowing thickly and reaching his peak as well, ramming into the clenched hole and riding his orgasm as his hand went faster on the Nara boy, eventually driving him over the edge as well.

“H-ah, Jiraiyaaaaa!” Shikamaru moaned as he splattered seed across the man’s hand and stomach, getting a little on his own stomach. He could feel Itachi’s sticky cum begin dribbling out even before the other had pulled out.

“Your vocals are magnificent, Shikamaru.” Jiraiya complimented, pulling out of Itachi, strings of white seed clinging to his cockhead and creating a mess on the bed. He placed his hands on Shikamaru’s ass, lifting him up in a way that forced the boy to put his arms around his neck. Jiraiya chuckled.

“Don’t be afraid to speak up. Your voice is inspiration for many new things.” He said, massaging at the supple backside under his palms. Itachi sat up from where he was, moving over.

“I would think his body would be the inspiration.” Itachi spoke from the other side of the bed, eyeing the lithe body clinging onto Jiraiya. The older man chuckled again, kissing Shikamaru for a few heated seconds.

“Oh yes, his body is very inspirational, but not many can have such an appropriate bedroom voice. There is a difference between a staged moan and a real one. He is a very good entertainer” He put one knee on the bed, outside of the white stains he’d created. He dropped Shikamaru down, the boy letting go to help. Jiraiya took his time eyeing him while he was above him, loving the natural sprawl the boy fell into and how his olive-toned skin looked with white cum streaked across.

“It’s because it’s not staged.” Shikamaru said, relaxing back on the sheets, getting comfortable. These two didn’t care about showy positions or ego-stroking looks staged to earn more money. Jiraiya raised an eyebrow, Itachi focusing more on the boy. Shikamaru flushed a little under the combined gaze.

“It’s too much work to remain detached from my clients and not enjoy it. It’s not so sinful; I’m not ashamed of what I do, so I let myself enjoy it.” He explained, one hand dropping lightly onto his stomach before he remembered the ejaculated mess he’d created. Still a little embarrassed by their attention he blushed harder at this misstep, lifting his hand and licking his palm.

“Mmm, you’re very beautiful like that…” Jiraiya said, loving the soft blush on the other as he licked up his own spend. His tongue seemed like a wicked little muscle, a dark pink against his skin. He climbed onto the bed, pushing at Shikamaru’s bent knees, spreading him more.

Itachi climbed onto the bed from his side, moving to kneel with his knees almost touching one of Shikamaru’s hips and side.

“Now, I know you’re supposed to be entertaining us, but just sit back and relax. I want more of the real thing, so forget that we bought your services.” He slid his hands underneath Shikamaru’s ass, massaging and palming the boy’s delicious globes before nudging him onto his stomach. He gripped the boy’s hips, bringing him up onto his knees while Itachi moved up higher, positioning himself in front of the boy.

“Go ahead and do what you want to.” Jiraiya said, spreading the Nara’s cheeks with his hands, revealing the white stained pucker. “We’ll just correct you.” There was laughter in his voice as he bent down, licking at the hole, tasting cum on the sweeter side.

Itachi did love his sweets.

Shikamaru took that initiative, knowing already what they obviously wanted and began licking at Itachi’s limp cock, tasting some of the least salty cum he was sure he’d ever taste. He eagerly continued lapping, wondering how he hadn’t noticed before; remembering Itachi’s tongue ring rubbing against his hard shaft he groaned, suckling the cockhead. That had been distraction enough not to notice.

He groaned suddenly, back arching downward as Jiraiya drove his tongue inside, sliding an experienced hand up and down Shikamaru’s slowly awakening arousal. The boy made luscious, wanton noises, licking kitten soft along the quickly rising shaft. He moved his head down, sucking on one of Itachi’s balls, lifting a hand to stroke at his already half-hard state.

Jiraiya’s second hand moved around Shikamaru’s hips, cradling his sac and thumbing the slit, delving his tongue deep, lapping at the ring of muscle before pulling back and licking from the now pink star down to the soft skin behind the sac. He nibbled at the hanging orbs, right where a piercing he hadn’t noticed before was safely snuggled. He smirked, licking at the ring, tugging gently, drawing out a low and needy sound from the other, his legs spreading almost involuntarily, sinking a little lower on the bed.

“Naughty naughty, hiding such a treasure.” Jiraiya whispered, hooking his tongue in the ring, tugging and licking at the same time. Shikamaru made another of his low moans, shivering down his spine. In truth, he forgot he had it most of the time during these things. People hardly ever found it seeing as it was behind his balls and they wanted him to be searching them.

He felt a hand in his hair, looking up to see Itachi staring at him, eyes portraying his lust. Shikamaru swallowed, wanting to move up and kiss him, but then Jiraiya was messing with his piercing and he was melting, moaning, almost writhing. He was fully hard by this point and he felt that if Jiraiya kept this up he’d need to be brought up again very soon.

“J-Jiraiya, please, you’re gunna make me cum again…” He panted, closing his eyes as he shook with pleasure, the older man sucking and tugging on the ring in a way he hadn’t even known could be done without pain being inflicted. He could hear Jiraiya chuckling, giving one last lick before pulling back. He lifted his hands away from Shikamaru’s heavy cock and balls, smacking one down playfully on his backside.

“You’re very sensitive for someone in this business.” Jiraiya said, watching as the boy slumped down, as if in relief. He eyed Itachi, the pale Uchiha shrugging minutely before increasing his grip on the brunette locks, guiding the other up to meet his mouth. Their tongues twined, Shikamaru enjoying the hot metal ball that ran along his own tongue.

Jiraiya enjoyed the view from the side, Shikamaru stretching up and tilting his head to reach Itachi’s mouth, leaving his body taut above the Uchiha’s. Jiraiya couldn’t help his eyes from wandering down, seeing the two rosy arousals so close, dripping and inviting. He grinned, reaching out and bringing the two together, pushing Shikamaru’s hips down to get them parallel. Delicious sounds immediately erupted from the kissing owners as he began to stroke.

“That’s it Shikamaru, just relax.” Jiraiya said, seeing the boy shudder and kiss Itachi harder. The pale man lowered his arms down, holding Shikamaru around the back as he increased the kiss, barely relenting for air. Shikamaru quivered, nearly bucking as Jiraiya’s other hand wandered back, pushing two fingers into his still stretched entrance, beginning to pump in and out with quick snaps of his wrist.

He shuddered all through his body as Jiraiya stretched out his long fingers, still pumping into him as his pinky began fiddling with the piercing. Shikamaru pulled back from the kiss, moaning loudly and spilling out against Itachi’s stomach and cock. Jiraiya smirked, bringing his hand back from the two dicks, licking at the spend there.

“Hmm, your stamina needs improving…But your sensitivity and vocals make up for it.” He commented, licking his palm clean in a consciously provocative way. Itachi smirked, petting at Shikamaru’s sweat dampened locks of hair.

“S-sorry, normally my customers have worse than me…” Shikamaru said, resisting the urge to just collapse on Itachi’s chest and cuddle him, drifting off to sleep. He could feel that the other male was still ready for more and it was his job to deliver.

“No, don’t be, you normally get less experienced people in this line of work. Why else would they pay for sex?” Jiraiya chuckled. “But there is always an exception.” He reached out, gently flipping Shikamaru off of Itachi’s chest. He leaned down, kissing Shikamaru as he lay panting softly.

“You know, you haven’t shown me that wonderful mouth of yours yet.” Jiraiya breathed once he’d pulled back. Shikamaru flushed, remembering his thoughts about the older man’s cock when he’d first been suckling Itachi. He got up, turning before Jiraiya stopped him.

“Get on your hands and knees and stay there.” Shikamaru gave him a minimally questioning look, doing as told. Jiraiya moved so he was sitting up against the head of the bed, legs spread and bent. He smiled, invitingly.

“Now, come to me, Shikamaru.” He said. Shikamaru swallowed, giving an amused and aroused smirk, moving on hands and knees towards the other man, swaying his hips and keeping his legs spread. The jewelry he sported glinted beseechingly to Itachi, the man licking his lips, his own pierced tongue aching to lick at it.

“Good, good, very sensual…” Jiraiya said, slipping a hand into his hair. Shikamaru smirked, bending down and licking a clean line up from the base to the tip, latching onto the end and sucking, hard. Jiraiya leaned his head back, closing his eyes and just enjoying the hot suction milking him and spreading tendrils of pleasure through his system.

“It looked better from behind.” Itachi said, moving up behind the boy. He placed his hands on the others hips, tugging until he was positioned with his ass in the air, upper body bent low, head bobbing now on Jiraiya’s engorged length.

“I’m sure it did.” Jiraiya agreed, opening his eyes. Itachi smirked at him, leaning down and running a tongue over the back of one of Shikamaru’s thighs. The boy shivered, shifting to spread his legs wider. Itachi continued, moving up and licking over all of the smooth skin, switching over to the other thigh when he reached the supple curve of his ass.

The ministrations left Shikamaru squirming, wanting the hot tongue to move higher, to slick across the dirty places, the good places.

“Please, Itachi…” He finally gave in, pulling away from Jiraiya when Itachi began lapping at his inner thigh, hands caressing his outer thigh. The Uchiha paused, his hands still caressing. “Please, I…I want you to lick me higher, lick me where Jiraiya did…” He begged outright, feeling a pulsing hotness between his legs again.

Itachi gladly lifted up, lapping at the hot crevice, delving his piercing into the hole, rubbing the smooth ball along Shikamaru’s inner walls. Shikamaru cried out, arching downward. Jiraiya watched the magnificent play of muscle spasms running up and down Shikamaru’s back, tensing his whole body in a wave.

The older man expected another explosion of white, but was pleasantly surprised when Shikamaru held it in. He grinned, looking around before his eyes landed on Shikamaru’s still bound hair. He grinned lecherously, reaching for the bit of elastic.

Shikamaru was too caught up in the rapturous feel of Itachi’s piercing hooking with his and pulling every time he licked at the skin behind his balls. He was concentrating, trying his best to not cum yet again when he felt Jiraiya lean forward, hands suddenly at his cock.

“Mmm, Jiraiya…Itachi…” He mumbled lowly, arching his back up and stretching his torso, feeling the other man sliding the hair tie over his dripping cockhead and down, the elastic restricting him at the base. Shikamaru made a whining noise, shifting his hips, reaching a hand down and over his stomach, tracing his hands through his pubic hair and to the warmed material.

“Just to help out. It’s not tight enough to completely block you, but it will hold it off for longer.” Jiraiya explained, nudging at Shikamaru’s shoulders. The boy looked up, eyes hot with passion as Itachi continued his oral assault at his entrance. Jiraiya smirked.

“Itachi, I think you’ll make him cum again even with the tie on him.” He chided, running a rand through Shikamaru’s hair. Itachi pulled back, lifting up from where he was and looked at Jiraiya questioningly. Jiraiya gave him another lecherous look.

“Alright.” Itachi said, sliding his hips up to Shikamaru’s slick entrance. He bent over, wrapping one arm around Shikamaru’s chest, pulling him up onto just his knees and slipping inside, hissing softly from the heat.

“Still a little tight.” He said, keeping his arm possessively around Shikamaru’s chest, the other one slipping to hold him around the waist. He began moving his hips slowly, stretching Shikamaru even more.

Jiraiya leaned back, enjoying the sight as he thought.

“Where’s the lube?” He asked, seeing Shikamaru swooning against Itachi, leaning his head against his shoulder. The Uchiha’s piercing flashed, dark tongue flicking against their entertainers earrings, nibbling.

“D-drawer…” Shikamaru moaned, wanting to move and writhe against Itachi. The other’s arms kept him from doing so, forcing him to just enjoy the feeling of Itachi sliding in and out, pushing at his already stretched walls.

Jiraiya leaned over to the bed’s previously unnoticed side table. Of course it would be in there, quick access and all that.

He smirked when he saw some of the fun toys, reaching in for what he was after. Hmm, he might have to use some of those next time…

He watched Shikamaru, the doe eyes locking on his hands as he squeezed some of the plain substance onto his hand. He grinned, unseen by the boy as he began sliding his hand up and down his cock. He almost laughed when Shikamaru’s tongue flicked out, licking at his lips in hunger.

“Soon enough, Shikamaru.” He said, startling the boy a bit. He flushed, turning his eyes from the thoroughly lubed and ready shaft, biting his lower lip as Itachi sunk in deep, holding him tight.

“He’s ready.” Itachi said, biting down at Shikamaru’s collar, suckling for a few moments to leave a mark. He unwound his arms from the boy, taking care to slide out before Shikamaru could begin moving against him as he’d wanted to earlier.

Jiraiya smirked, remembering the toys in the drawer.

“Good, but there’s been a slight change in plan.” He gave himself praise for resisting long enough to lube himself up, but really, who could blame him for wanting to torment Shikamaru a little longer? The boy was gorgeous in the throes of passion.

Itachi raised an eyebrow, his hands wandering over Shikamaru’s sides. Jiraiya leaned back over, hands delving into the depths of the drawer, coming back up with all kinds of goodies.

Shikamaru’s eyes widened as he looked at what Jiraiya had pulled out, swallowing. Some of it even he hadn’t used yet, left there as a ‘just-in-case’ by the owner.

Itachi gave Jiraiya a raised brow, still not moving from behind Shikamaru. Jiraiya shrugged, still grinning, as he picked up something bright, cotton candy or neon pink from the pile, shiny and slightly see through.

Moving forward, he slipped his hand down Shikamaru’s length, stroking his knuckles across the dorsal vein in an almost loving manner before he began pulling the make-shift cock ring off.

“Have you ever used one of these before, Shikamaru?” Jiraiya asked, holding up the thing. It had ridges along the ring and one large square that obviously held batteries. Shikamaru swallowed, shaking his head, panting a little.

“N-no, no one’s ever asked…” Jiraiya couldn’t keep the grin from his face as he reached out, gripping Shikamaru by the dick and pulling gently, getting him to move closer. Jiraiya sat back against the headboard, moving pillows so he could be more comfortable.

He gripped Shikamaru’s hips, placing him right on his lower stomach, his still-lubed cock rubbing along the cleft of his ass. Shikamaru inhaled, arching slightly and rubbing back a little, causing Jiraiya to groan, increasing his grip.

“Hold on now, haven’t got this on you just yet…” He admonished lightly, breathing deep as he felt the warm ass press against him, the balls rubbing invitingly against his lower belly.

“You might cum again from what I have planned, but…” Jiraiya began slipping the professional cock ring on, Shikamaru’s back arching as it slid over his sensitive organ. Jiraiya paused, that ass squeezing him again.

“But with these toys it shouldn’t be a problem to get you up again…” He finished with soft breaths, trying not to pant. He fastened the pink cock ring in place, tight enough to block Shikamaru from release far longer than the hair tie would have had.

Jiraiya reached down, lifting Shikamaru up at the ass. He had the greatest temptation to just push him back those few inches and let him slide down his wet needy cock, but he had other ideas in mind.

“Itachi, would you do the honors?” He asked, once he’d gotten Shikamaru turned around, presenting his bright new cock ring to the other. He lowered the boy down, until he was leaning back against Jiraiya’s chest, his lower back pinning Jiraiya’s erection down, rubbing against it.

“It’s a very simple on off switch.” Jiraiya explained keeping his voice in check as Shikamaru wriggled a little, his spine easily felt through his skin by Jiraiya’s sensitive shaft, rubbing against the hungry organ deliciously.

Itachi nodded, dropping onto his hands and knees.

Jiraiya and Shikamaru both shifted at the sight, arousals twitching as Itachi crawled forward, showing a grace and erotic balance that showed his toned body to all lucky enough to see. Shikamaru whimpered, squirming, driving the ridges of his spine against Jiraiya who hissed, and increasing his hold on Shikamaru’s wrists that he held away from the boy’s body.

“Fuck Itachi you could make a man cum without even touching him…” Jiraiya said, Shikamaru quivering against him more and more the closer Itachi got to him.

Itachi paused above Shikamaru’s leaking end, eyes rolling up to the younger males. He held the doe gaze, opening his mouth and licking his lips. Shikamaru whimpered again, leaning his head back against Jiraiya’s chest, breathing out.

A sudden hotness over the head of his arousal made him jerk, writhing against Jiraiya, hands tightening into fists from the unforeseen pleasure. His writhing and shivering only increased the further down Itachi went, fire spreading from his hot cock throughout his body, unable to touch back.

“F-fuck…” Shikamaru gasped, pulling against Jiraiya’s hold. The man held fast, breathing harshly as Shikamaru ground against him and Itachi gave him a front row seat to some of the best cock sucking he’d ever seen.

“You’re not holding back any, Itachi…” Jiraiya commented through a dry mouth, licking equally dry lips. The Uchiha’s eyes looked up, showing just how much he enjoyed tormenting the both of them. Jiraiya groaned.

“Just as long as you don’t make him cum…unless you want to bring him back up yourself.” Jiraiya warned. Itachi made a humming noise, setting Shikamaru off on another stint of shivering and shaking, writhing in pleasure.

Pulling back and off with a wet pop, Itachi proceeded to lick and kiss down the wet length, nibbling at the dorsal vein, letting his metal stud rub against the sensitive skin. When he got to the cock ring he paused, running his tongue all along the skin just before the pink material, going all the way around, drawing still more sounds from Shikamaru. He finally lifted his mouth off of Shikamaru’s skin, using his teeth to click the switch, setting it on vibrate.

Shikamaru nearly screamed, twisting and pulling and fighting with Jiraiya, moaning outright as the vibrations ran up and down the length of his hot cock. Jiraiya panted, holding tight to the thrashing boy, groaning lowly to himself as he heard some filthy words slipping through Shikamaru’s mouth as he ground back against him.

Itachi smiled, licking from the cock ring all the way to the tip before abandoning the hard length all together. Shikamaru made protesting little noises, wanting the heat back, wanting to be stroked closer and closer to his release by that devilish tongue.

Itachi leaned over to the pile of toys, lifting from it a strap of leather much like a collar, with a neon pink ball that matched the cock ring attached at the front. Jiraiya whistled.

“Nice choice.” Itachi smirked slightly, placing the ball at Shikamaru’s lips. The boy opened up, tongue dark against the bright pink of the sphere. His eyes were wide as Itachi slipped his hand back; fastening the buckle at the right tightness, making sure it wouldn’t be uncomfortable. Shikamaru quivered, the vibrations still purring against his erection in a maddeningly arousing way, the tightness staving off his release, saliva tainting one corner of his mouth as his jaw was forced to stay open.

He made pleading noises when Itachi picked up the handcuffs.

“Someone’s feeling kinky today…” Jiraiya said, licking his lips as he eyed the fuzzy things, neon pink again. Itachi only continued to smirk, taking Shikamaru’s wrists from Jiraiya in one hand, the pink cuffs in the other. He pushed them back, around Jiraiya’s neck and further, until Shikamaru’s fingers brushed cool metal.

Shikamaru’s eyes widened, fingers locking onto the intricate design of the headboard, giving pleading eyes when he felt the cuffs slide across his skin, clicking. He let go of the metal, tugging and feeling that yes, he was bound now. He felt Jiraiya’s now free hands move down, caressing and petting at his skin, tweaking a nipple.

“Soon, Shikamaru.” Itachi said, holding a thick black cloth in his hands now. Shikamaru whimpered, the sounds muffled slightly by the ball gag, the cloth sliding across his eyes and obscuring all from his sight. He could hear Jiraiya’s approving rumble against his back.

“Very nice. I’m curious…” He paused, breathing deep, inhaling sharply. Shikamaru whimpered again, rolling his neck, eyes searching the darkness for a source of light, a small bit of the picture.

“Now that’s just cruel, Itachi.” Shikamaru blinked, his skin tensing, waiting for something, anything. He had a feeling Jiraiya, although being truthful, was playing with him a little.

He felt shifting on the bed, his blood pumping quicker and quicker as he tensed further, mind reeling with so many different things it could have been. He yelped against the ball gag as something nosed at his entrance, his back arching off of Jiraiya along with his hips, the metal making hollow sounds as he yanked on the cuffs in a spasm, moaning heatedly.

“Look at him, so sensitive!” Jiraiya said right next to his ear, a hand pushing down on his flexing stomach, getting Shikamaru to settle back against his chest. The older man looked over, seeing Itachi pushing the dildo further in, breathing softly against the leaking head of Shikamaru’s erection. Jiraiya groaned, shifting his own erection against Shikamaru’s back lightly, taking the edge off a little.

Itachi leaned back once it was all the way in, just a few extra inches of neon pink not buried within the boy. He got up, moving up on the boy’s bound body, gripping at Shikamaru’s dripping and eager cock.

He reached over for one last thing, pulling out a leather collar with pink stones sparkling, imbedded within it. He turned, reaching out and placing it around Shikamaru’s neck, tightening it as tight as any choker. He clipped the small, three foot leash to the hook in the front; black leather dusted in pink sparkles.

“Neon pink bondage set, go figure.” Jiraiya said with a chuckle as he took in the shiny pink ball gag, the pink cock ring, the matching pink leash and collar, and the pink dildo, remembering what color the cuffs were. Itachi shrugged one pale shoulder.

“A woman’s set maybe.” He positioned himself above Shikamaru, sinking down without more preparation then what Jiraiya had given him earlier, keeping the leash in one hand.

Shikamaru cried out, the rapturous call broken by the colorful ball gag. His body tensed all over, tightening, pleasure rushing forward in what would have been a powerful orgasm if not for the tight ring of pink restricting the luxury. Shikamaru collapsed back, panting and shivering, muscles twitching under his skin, still so hard and wanton.

Itachi lifted his hips, feeling his entrance close around all of Shikamaru, swallowing his swollen cock hungrily. He pushed back down, hearing the broken whimpers again, seeing how much Shikamaru was enjoying it as he arched and panted through his nose.

Jiraiya almost came from the sight, Itachi seated on Shikamaru’s weeping dick, the boy thrashing and twitching underneath the luscious beauty. His eyes focused in on Itachi’s hole eating up all of Shikamaru, gripping the hot pole tightly as the Uchiha began lifting and lowering himself, one hand on Shikamaru’s stomach for balance.

Just as Jiraiya was wondering how long he’d be able to last with such a delicious sight in front of him, Itachi slowed down. The Uchiha leaned back, free hand sliding across Shikamaru’s skin and leaving twitching spasms in its wake. He gripped the pink toy, pulling the leash taut and forcing the boy to arch against Jiraiya, rubbing into the older male’s engorged length as Itachi pulled the neon toy out until just the blunt head of it was still within Shikamaru’s needy entrance.

Mirroring this, Itachi lifted his hips up until just the leaking head of Shikamaru’s cock was in his own hole. As synched as he could, Itachi rammed in at the same time he slammed down, filling and being filled at one time.

“Mmm, hmm!” Shikamaru moaned around the gag, his head rolling to the side as his arms tugged and thrashed, wrists rubbing almost painfully against the padding of neon fuzz on the cuffs. He shivered, feeling Jiraiya’s hands at his chest, pinching and rolling his nipples. He could still feel the man’s cock, hot and leaking against his back as he writhed and bucked.

Itachi continued fucking the bound male with the toy, jerking on the leash every time Shikamaru pulled away, arching up, or started to push into the Uchiha. Shikamaru whimpered behind the gag, wanted to push up into Itachi, to meet the quick thrusts of the neon toy but getting jerked every time he did so.

Picking up the pace with the bright toy, Itachi kept up with his own impalement by ramming in deep with the pink dildo and pushing Shikamaru’s hot dick just as deep within himself.

“Fucking beautiful, Itachi…” Jiraiya said, rolling Shikamaru’s pert nubs even more, bending down between the quivering arms and nipping at his collar bone, on the other side than the one Itachi had marked.

Itachi smirked at the man, feeling his completion nearing him, slowing down the hand with the toy as he sped up his own pace, pulling on the leash as Shikamaru attempted to begin moving against the now completely still toy.

Letting go of the toy completely, Itachi moved both hands to Shikamaru’s stomach, sliding down to his hips as he began moving up and down, faster and faster. Shikamaru cried out, writhing, thrashing against the bonds and the leash, pushing up into Itachi, trying to find his release as he felt Itachi spill out across his stomach.

Itachi pushed down on Shikamaru’s hips, keeping him down as he slid off, swinging one leg over Shikamaru’s so he was kneeling at his side as he had been earlier.

Shikamaru’s desperate pleas and begging were distorted by the ball gag, his wanting fingers kept at bay by the cuffs. He thrust his hips up into the air, desperate, wanting the sweet heat again. Hot, frantic tears welled in his eyes, slipping out and under the cloth binding when he felt the toy being slid out of him.

Itachi reached for the ball gag, still holding the end of the leash as he undid it, dropping the pink ball to the side amid a chorus of begging and whimpering.

“Please, please, Itachi, Jiraiya, please, fuck me, anything, please.” Jiraiya chuckled lowly, nibbling at Shikamaru’s ear lobes affectionately.

“You sound so good when you’re begging, Shikamaru.” He said, gripping Shikamaru at the chin, tilting his head and laying a kiss on his lips, sliding his tongue inside easily, silencing the quivering, needy voice.

While Jiraiya was busy with Shikamaru, Itachi had bent down, beginning to lap up some of his spill, leaving most of it as he moved up, swirling his tongue around and around a pert nub, rubbing his piercing against it wetly.

Shikamaru moaned into Jiraiya’s mouth, bucking. Jiraiya pulled away, looking down to where Itachi was sensually attacking Shikamaru’s front. He grinned.

“As much as I love the view, I don’t think Shikamaru can handle much more.” He said, lowering a hand to Itachi’s black locks. Itachi looked up, nodding as he saw Shikamaru’s pleasured, teary eyes. He moved up, licking at the tear tracks, kissing him deeply.

“All right.” He said once he’d pulled back, Shikamaru following him as far as he could. Jiraiya moved his hands down to the other’s ass, lifting him up, making sure his arms weren’t uncomfortable from the cuffs. There was just enough metal bar going up that it didn’t bend his arms too far back, only forcing him to arch his back forward.

“Ready, Shikamaru?” Jiraiya asked with amusement, holding the other suspended over his slick erection, waiting patiently despite how thoroughly hard and ready he was. Shikamaru nodded eagerly, digging his feet into the bed and pushing down, wanting to be filled and wanting it now. Jiraiya chuckled, lowering him down carefully.

The boy was thoroughly stretched, still snug around Jiraiya’s slicked up cock, but no longer a tight constriction. He smirked, thrusting a little, shallowly, just enjoying Shikamaru’s foul mouthed begging. The boy wanted everything at the moment, to be fucked, to suck cock while one of them rimmed him again or to be fucked into the mattress while one of them rode his mouth, or for them to ram into him with the fucking dildo again so long as he was fucked hard.

Itachi moved in-between Jiraiya’s legs, watching as Shikamaru frantically tried to gain release, pushing down onto Jiraiya’s thick cock with abandon, trying to gain friction that had been lost with his stretching. He pulled the leash taut again, Shikamaru’s body stilling as the memories came to him, still blindfolded and blind to most of Itachi’s movements.

This was followed by fresh suggestions of Itachi sucking him while Jiraiya fucked him, or the other way around, or he could suck Itachi while Jiraiya fucked him, just if Itachi would help him get his release.

Jiraiya’s hand moved away from Shikamaru, down to Itachi’s limp member. He grasped it, stroking shallowly, moving slowly with his hips so as to prolong Shikamaru’s release even more.

He felt Itachi start to move into his fingers, glancing over to see that the other man had one hand cupping his balls, the other behind him, wrist moving in a way suggesting a private finger fuck.

Jiraiya groaned at the images coming to his mind’s eye from that, long pale fingers disappearing into a hungry hole, moving in and out in a parody of a good fucking. He licked his lips, gripping Shikamaru’s hip harder as he stroked the slowly growing organ, glad that the Uchiha had such stamina at a time like this.

“Jiraiyaaaaa, fuck me!” Shikamaru demanded, tilting his head, the cuffs clinking against the metal, pushing down insistently on Jiraiya’s hot cock. The man bit his lip, restraining from doing just that, despite all that he wanted.

“Not just yet, Shikamaru…” he said, pumping faster. He groaned, dropping his head back. Really, that wasn’t fair on Shikamaru’s part…Flexing that hot ass all around him like that when all he was trying to do was increase their pleasure.

“Patience, Shikamaru, patience…I know it’s hard, but it will be worth it, you’ll see…” He breathed out, nibbling Shikamaru’s ear again as he felt Itachi getting nearer and nearer to fully hard again.

Itachi squeezed the hand at his sac, rolling the orbs around, feeling pleasure pump through his system, lifting his tired cock from his body slower than any of them would have liked. He breathed deep, his fingers sinking in deep, brushing his prostate.

“Jiraiya, wait…” Itachi said, moving to the side. Shikamaru groaned, before hearing Jiraiya chuckle again. Suddenly the blindfold was tugged up, Shikamaru almost blinded by the sudden light entering his doe eyes. He blinked, turning his face, feeling Jiraiya turn it back.

“Look, you don’t want to miss this…” Jiraiya said, snickering as Shikamaru’s wriggling and flexing ass finally ceased, staring.

Itachi was in front of them, on his knees with his ass in the air, upper body low as he rested on one elbow. The other arm was back, holding onto the neon pink toy that had been in Shikamaru earlier, sliding it in. Shikamaru made a soft sound, the cuff clinking as he attempted to touch the man who was now pounding into his own ass, back arching.

Gods he just wanted to reach out and touch Itachi, his ass swallowing the toy as hungrily as Shikamaru remembered it swallowing him down, his cock twitching. He whimpered again, Jiraiya hissing as the boy clamped down on him, thrusting down.

“Mmm, Shikamaru, I know you want to touch, but I don’t know where the keys to those cuffs are…” Jiraiya said softly through a strained voice as he kept from thrusting back up with abandon.

Itachi continued to thrust the toy in, feeling his cock hardening under the onslaught, quickly dripping pre-cum, his completion swimming before his eyes. He stopped, panting slightly, pulling it out in a way that made both of his audience swallow huskily. He turned, raising a brow at Jiraiya.

“Alright, just wanted him to see the show. You would make a lovely entertainer, Itachi.” Jiraiya said as he pulled the blindfold back up, obscuring the erotic sight of a hard and dripping Itachi from Shikamaru’s sight. Itachi moved closer.

Shikamaru tilted his head from side to side, unable to see now that the blindfold was back but hearing when Itachi moved up, lifting his legs at the thighs, Jiraiya’s hands moving to help hold him up. Shikamaru wriggled, unsure if he was right about what they were planning when he suddenly felt Itachi’s cockhead pushing into his already filled hole.

Shikamaru moaned, his arms flexing where they were, bent in the air, his hands gripping the metal as a handhold. He began to shiver all over, quivering with excitement as Itachi finally sank in all the way, his and Jiraiya’s sac brushing. He could hear the little vibration from the cock ring, still buzzing and stimulating, the noise overshadowed by all others until now.

“Oh, god….” Shikamaru whispered, knowing he would have come again if he didn’t have the cock ring on him, loving the feel of the two hard dicks within him, rubbing along his walls intimately, almost too much, pushing him closer to the release he’d been craving.

“Oh, gooood!” He gasped as Itachi began to move, pulling back and slipping in, Jiraiya quickly joining in. Shikamaru gasped, muscles tensing as two different cockheads rubbed across his sweet spot, pulling at the ring of muscles.

Shikamaru wasn’t sure how he wasn’t tearing, feeling so full, utterly filled with gorgeous, luscious cock, blinded to what it looked like and only able to feel it, feel it and hear his own pleasured moans mingling with Itachi’s grunts and Jiraiya’s half formed comments and compliments.

He screamed, body tensing as a powerful orgasm ripped through his being, tearing the extreme sound from his throat as his body hugged the two organs tighter together, friction milking his ride even more.

He was unaware of any noises the other two might have made while they spilled inside him, their combined seed dribbling out before they were even out, not knowing how his arms pulling futilely against the bonds, his eyes rolling in pleasure behind the blindfold, spurts of hot seed staining his and Itachi’s chests.

He collapsed down, utterly spent and boneless. He could feel the hot spend of the other two slipping down his ass, Itachi pulling out and dropping his legs causing it to start dribbling down the back of his thigh as well as his inner thighs. His own cooling arousal was sliding down his and Itachi’s chests, leaving shiny tendrils of his lust behind.

Jiraiya sighed, relaxing. He pulled Shikamaru off of him, waiting until he saw the Uchiha reach for the keys and heard the chink, setting the tired out boy beside him. He lifted the blindfold, leaving the leash and collar while he reached down to pull the cock ring off. Somewhere among all the activity it had died.

“We’re all so dirty now.” He commented, amused. Shikamaru panted, lifting a hand and lazily waving towards a door none had bothered questioning before.

“Bathroom. Towels.” He couldn’t have gotten up even if he’d cared to try. Itachi lay out beside Shikamaru, giving Jiraiya a look. The man laughed, not bothering to argue as he got up.

When he got back Shikamaru was snuggled against Itachi, sound asleep, slowly being glued to the Uchiha’s side as he pressed his drying cum covered chest to Itachi’s smooth side.

“You two are adorable, all covered in cum and cuddling, with your long hair and legs entangling…” Jiraiya said, smirking down at Itachi. The man just held out a hand, cleaning both he and Shikamaru up with the damp towel. Shikamaru shivered at the feel, but stayed asleep, only clinging tighter to Itachi’s warm sides.

Jiraiya sat down, brushing his hands through Shikamaru’s hair, thinking.

“We should do this again.” Itachi only nodded. Jiraiya smirked lecherously, grinning down at the other man.

“He is such a lovely entertainer, I wouldn’t mind coming on my own.” Itachi merely shrugged, looking down at Shikamaru.

“Perhaps.”