IF ARE UNDERAGE OR ANYONE OF THE FOLLOWING SQUICKS YOU OUT GTFO!!! NOW!

WARNINGS: light bondage, fingering, rimming, slash, sex toys, fisting

A/N: This was written for this prompt over on the new kink meme on LJ:

McCoy sets himself a challenge; multiples. As soon as Jim's come McCoy starts working him up again. How many times can he make Jim come in one night? Answer: A whole fucking lot. He ends up practically dragging the last one out of Kirk, though; "C'mon, babe, you can do it, come for me..." "Oh, God, I can't. I can't!" and then he comes so hard he's literally sobbing with it.

Any kink welcomed. Any at all. Except for blow jobs. (Kissing that particular area is a-ok, though.) Major bonus points for anal plugs, anal beads, and Jim's (backless!) briefs staying on until, like, the third orgasm. With McCoy's hands never once going inside them (as in, cock and balls are completely untouched skin-to-skin).

Leonard McCoy sat at his desk in his dorm room writing a letter to his little girl. His roommate was gone for the weekend and it was a quiet Friday night. Which was surprising considering that Jim Kirk was lounging on McCoy's bed. McCoy was amazed at how well behaved he was tonight; just sitting there idly filliping through Bones' old paper copy of Gray's Anatomy.

"You know, sometimes I'm totally jealous of women." Jim mused.

"And why is that, Jim?" Bones responded without looking up.

"Multiple orgasms"

This time Bones did look up.

He looked a Jim quizzically for a moment, "Men can have multiple orgasms too."

"No, they can't." Jim stated with a laugh.

"Yes they can, it's a medical fact." Bones replied in all seriousness.

"Oh, yeah? Prove it."

And that is how Jim Kirk came to be kneeling in his boxers, on McCoy's bed, with his hands bound to the headboard. Bones had to admit that it was nice view and one he would never get tired of. They fooled around now and then, but Jim's challenge to 'prove it' gave him license to explore territory that they hadn't before.

"Do you trust me, Jim?" Bones asked, sliding up behind him, caressing his toned stomach.

"What kind of a question is that?" was Jim's cocky retort.

Bones stilled and pulled back, "An important one. Do you trust me, yes or no?"

"Yes. Bones, you know I trust you…implicitly." The last word was no more than a whisper, Bones wasn't even sure he had heard it.

"What's your safe word?" he asked firmly, moving back to caress Jim's ass this time.

"Klingon"

McCoy's eyebrow twitched upwards. "Interesting choice," He said, leaning over to take some things out of his bedside drawer.

He laid them out on the bed where Jim couldn't see them and picked up a silicone ring from among them. Keeping it enclosed in his hand he fit himself against Jims form. He kissed the juncture of neck and shoulder, running his hands down to the waist of Jim's boxers. He shoved his hands down the front of the boxers and slipped the cock ring down to the base of Jim's already half hard member.

"I thought those were to keep you from having an orgasm," Jim said excitement evident in his voice.

"No, they're to keep you from ejaculating."

"What's the difference?" the bound man questioned.

"Shut up and I'll show you," Bones whispered against his ear.

He removed his hands from Jim's boxers and let them wander over the rest of his body, lips flitting over his back leaving light kisses in their wake.

"Mhmm, Bones," Jim giggled at the ticklish sensation, "aren't you going to take your clothes off?"

McCoy smiled against the nape of Jim's neck where his lips currently were. He moved aside to dispatch with his clothes. He didn't make a show of it; he just shucked off the shirt, pants and underwear, and returned to the strong, warm body that was tied to his bed.

"That better?" He breathed against Jim's ear.

"Much, but aren't you going to take off my boxers?" Jim asked.

"No," Bones replied playfully, his hand moving to cup Jim's ass, "They keep your cock out the way so well."

"How are you going to get me off if you don't touch my cock?"

"Prostate stimulation"

"You still need to take off my boxers to do that." Jim smiled back at him.

"Do I?" He replied with a raised eyebrow.

Jim heard the snip of scissors cutting through fabric and goose bumps rose over his skin as the cold metal of the scissors glided across his ass, cutting a large hole in the back of his underwear.

"You were saying, Jim?" said Bones smugly.

"You kinky bastard," said Jim, eyes shining with delighted shock.

"Don't sound so shocked, Jim, I'm human too," replied Bones, biting a clothed ass cheek.

Bones continued to fondle Jim's partially clothed ass with one hand while the other reached for the bottle of lube next to him. He slicked his fingers and poured some onto the skin exposed by the hole in Jim's boxers. Jim shivered and emitted a gasp at the sensation of the cold liquid hitting the sensitive flesh. Bones chuckled darkly; bringing his gel slicked fingers up to play with Jim's opening. He circled it gently with his finger, applying more pressure as he went. Tightening the circle until the relaxed ring of muscle easily accepted his finger inside. He pushed a second finger in, encountering just the slightest resistance. He crooked his fingers forward, easily finding what he was looking for. He felt Jim's walls ripple and tense as he stroked it, hot and tight. He let out a soft happy groan at the feeling.

"Ahh, Bones…more, please!" Jim groaned; the two fingers not nearly enough.

"My pleasure, Darlin'" McCoy replied lustfully.

He slipped a third finger in carefully beside the others, slowly thrusting them in and out. Jim's heavy breathing and half gasped moans permeated his ears. He knew Jim needed more. He trusts his fingers faster and bent down to add his tongue to the mix. He flicked the soft wet muscle around his lube soaked fingers, and laved the edge of Jim's filled opening. Jim's hands tightened their grip on the bed rail he was tied to. If he was shocked at McCoy's actions he didn't express it. McCoy's tongue and fingers fucked and licked Jim open; he could feel the inner muscles of Jim's ass tensing around him and doubled his efforts. He struck that spot deep within Jim once more before Jim's whole body suddenly tensed for an infinite moment. A deep guttural moan escaped Jim's lips and his body went slack.

"Are you alright?" Bones asked smugly.

"I didn't cum," responded Jim through panted breaths, "I had an orgasm, but I didn't cum."

"Well, that was the point of this experiment. You ready for round two?" said Bones, kissing the center of Jim's back.

"Oh, hell yes…" came Jim's breathy answer.

McCoy smiled and picked up a well proportioned dildo from the collection of things he'd taken out of his drawer. He easily worked it into Jim's stretched and lubed ass. He turned the knob at the base of the dildo and it started vibrating lightly. He heard Jim's breath hitch in surprise. He worked the dildo in and out fucking him with it at an increasing pace. As he increased the speed of the trusts he turned up the speed of the vibrations.

Every time he pulled it out Jim would try to push back onto it, attempting to stimulate more of his already sensitive insides. The tip of the dildo bumped and rubbed against Jim's prostate, the dual sensations of vibration and being fucked causing the familiar tension of pleasure coil deep in his belly. His cock throbbed against the tight ring restricting its blood flow. He was so hard it hurt. So was McCoy. Jim could feel McCoy's weeping cock resting heavily against his thigh. He suddenly wished that it was Bones' thick, hard cock inside him instead of the hard vibrating plastic.

The mental image of his friend fucking him combined with the deep vibrations was enough to send him over the edge for the second time that night. Bones watched, pupils blown wide with lust, as the orgasm wracked Jim's body. His lean muscular back arched towards the bed and his head thrown back as he shouted out his pleasure. Bones turned the vibrations down slowly as Jim rode it out, gently bringing him back down.

Bones pulled the toy from his body and Jim's long fingers flexed against the unyielding metal of the bed rail. He took several deep shaky breaths. After a few moments of trying regain his center he turned his head back to look at Bones. Bones was sitting back on his hunches stroking himself, gaze fixated on Jim's ass. His eyes were black from lust and his was breathing fast. His heavy, purple cock glistened with precum.

"I'm still hard, so why don't you put that to better use?" Jim said a lazy, lust crazed half grin spreading across his face.

"You're ready for another go?" Bones asked while crawling back towards Jim.

"Shut up and fuck me."

"Aye aye, captain," said Bones lining up his cock and thrusting hard into Jim's pliant body.

"OH, FUCK!" Jim yelled as Bones hit his prostate; the sensitized nerves amplifying the feeling and blurring the line between pleasure and pain.

McCoy thrust wildly into the man beneath him, digging his fingers in to the narrow hips. His control was micro-thin after watching his friend get off twice. There was no way he was going to last long after that. Neither was Jim. His painfully hard cock was twitching and leaking inside the remnants of his boxers. He wanted to touch himself so badly, needed the relief it could provide. He knew McCoy wasn't going to let him, that's why he had been tied up. He needed to cum so badly it hurt. His only option was to push back against the other man's cock and urge him to go faster, harder. Bones complied and even through his erratic pace he managed to hit Jim's prostate on almost every upstroke.

Harsh pants and guttural moans filled the room as they drove each other toward their climaxes. Jim's balls got impossibly tighter as he let go first, cum shooting against the inside of his boxers. He cried wordlessly as his whole body tensed, his ass clenching tight and hot around McCoy's cock. The sudden increase in pressure ripped a primal shout from McCoy as he came deep inside Jim.

Jim hung limply from his bonds, eyes half closed and breathing ragged. Bones reached up and undid the ropes, carful to lower Jim to the bed gently. He flipped Jim onto his back pulled off the ruined boxers. He carefully removed the cock ring from Jim's now flaccid penis and tossed it aside.

"Bones…" Jim murmured as the older man slowly slid up his body.

"I'm here," he replied, kissing Jim sweetly.

His hand trailed low along Jim's hips and pale thighs. He pressed his lips hard against Jim's, kissing him deeply, possessively. Jim moaned lazily as Bones tugged at his bottom lip with his teeth. His large, probing hand has worked its way in between Jim's legs and was teasing his already abused hole.

"Think you can handle just one more?" He asked, one finger easily slipping inside.

"Mmh…You're going to be the death of me…" Jim mumbled out.

Bones chuckled, "That's my line, kid."

Jim breathed out a laugh and smiled his consent.

Bones grabbed the bottle of lube and spread Jim's long legs apart. He slicked the cool gel over his hand and liberally applied some extra to Jim's still lubed hole. He pushed two fingers inside with no resistance and a third one quickly followed.

"Jim, if this hurts or gets to be too much just say the word and I'll stop. Do you understand?" Bones asked concern coloring his voice.

"Keep going," Jim nodded.

Bones smiled and thrust his fingers in and out, spreading them apart slightly to further stretch Jim's ass. He slipped hi pinky in beside his other fingers and felt Jim press down on them.

"More?" he asked.

"God, yes," was the throaty response.

He pulled his hand out. He folded his thumb in to his palm and folded his other fingers around it, trying to make his hand narrow. He placed the tips of his fingers back at Jim's entrance and pushed. Jim took him easily to the second knuckle. He pulled out a bit and thrust again, pushing in a little deeper. He continued thrusting until he reached the widest part of his hand.

"Just do it, Bones!" Jim groaned.

He did. He watched in fascination as Jim's body swallowed his whole hand. Bones moved his fingers as much as he could, massaging Jim's prostate. Jim's body arched as he openly moaned and shouted. He rocked his hand back and forth in small thrusts, never ceasing his massage of Jim's prostate. Jim's back arched further, leaving the bed.

"BONES!" he cried chocking back a sob, "OH! God, Bones…more!"

Bones thrust his hand faster. Jim's eyes rolled back, his toes curled and his whole body went taut as he let out sobbing scream. His body fell back to the bed, eyes closed and limp, breathing heavy. McCoy gently removed his hand. He lightly kissed the exhausted man.

"Are you alright…Jim?" He asked.

"uuhg"

"I'll take that as yes," Bones said.