DISCLAIMER: I do not own any of the characters from Star Trek or the actors playing them. This is all fiction.
This was written for a prompt on the st_xi_kink (Star Trek Kink) meme community on LiveJournal, in which the prompt stated, "5 times Kirk has tried to get Spock to laugh and failed, and one time when Spock made Kirk ROFL."

Enjoy. =] Parts 4, 5, and 6 will be coming soon.

Jim Kirk was known for having pretty awful jokes. You know, the ones you got on gum wrappers and popsicle sticks? A whole section of his brain seemed to be dedicated to storing them, and he had a bad habit of pulling them out at the most inappropriate moments. Though, it didn't help that as terrible as the jokes were, members of the crew laughed. Even if they were just chuckles, they recognized that the joke had some tact.
There was one person, however, that would never muster even a chortle when Kirk decided to "pull a funny".

Spock.

No surprise, of course. Vulcans did not readily show emotions. The only time Spock ever conveyed any particular emotion was when he was holding Kirk to a control panel on the bridge, ready to choke the life out of the foolish soon-to-be-Captain for saying that he never loved his mother. Other than that, people could barely elicit a small smile out of the Vulcan. It just didn't seem possible.

Kirk was a sucker for a challenge, and he'd be damned if he didn't give it a shot. Many times, in fact.

The first time Kirk every tried to get Spock to laugh, he resorted to an old faithful of jokes: the fake finger. He thought he was being sneaky, feigning a good, firm handshake with his best friend Commander Spock....and then he let his "finger" drop, dramatically gasping, "Oh my GOD--my FINGER fell off!"

Spock promptly bent down and picked up the fake finger, inspecting it before looking at Kirk. "Captain, forgive me, but I don't believe your skin is made of silicon and plastic." He then nodded to the Captain and walked back to his post.

Maybe next time.

During the Enterprise's investigation of Mordan IV's continuous civil battles, Kirk had to find some way to keep the crew's morale alive. Though most of his friends gave small smiles and laughs at his attempt to make them laugh, Kirk never got even a glance from Spock. Perhaps he would have to take this to a more personal level.

While on shore leave a couple months back, Jim had made a purchase at a local gift shop with Bones, one that they would still joke about from time to time. Sitting in his quarters was a single white coffee mug with a picture of a scantily clad, greased up young guy in some sort of modeling pose. To the naked eye, the mug was just utterly creepy. Especially because it was Kirk who owned it. But then the uniqueness of the mug was revealed, and it often sent the viewer out of the room, shaking their heads and wondering why they even bothered.

Jim had offered to make Spock some tea one morning while the crew was scanning the surface of the foreign planet, looking for particularly sticky spots in need of some sort of intervention from the Federation. Spock, an avid tea drinker, happily took up the Captain's offer, a bit tied up at the moment with his control panel.

Jim whistled as he poured the tea into the mug, laughing inwardly at the possible laughs he would get from Spock. Or, he hoped he would get. He continued to whistle as he brought the mug over, handing it to the Commander.

And this is where the mug's true shock value came into play. You see, the mug itself stays intact when hot liquids are poured in. However--the picture does not. The hot tea caused the skimpy swimsuit on the male model to suddenly vanish, revealing his "goods" of epic proportions. A few officers on the bridge tried to hold back laughter once the image was revealed, as did Kirk.

Spock looked at the others, arching a singular brow and wondering what the devil was so funny. And then he saw the picture.

Brow still arched, he examined the picture for a moment before handing the mug off to Kirk. "....sometimes I worry about the absurd degree of effort you put into your jokes, Captain."

....Third time's a charm.

Kirk was a huge fan of bad punchlines, as well as tricks and pranks. He often used the computer in his quarters to access archives from the 21st century to read such jokes, and the cadets passing his quarters would stop and stare at the door because of the hollering laughter they heard from within. He enjoyed plain knock-knock jokes, or funny short stories. Whatever they were, he probably had them in his archives.

One day during a bi-weekly ship restock at the Starfleet base, the crew members on the bridge were sitting at their posts, waiting for some instructions as to what needed to be done. Chekov had found interest in hacking the main harddrive and playing some form of Minesweeper that he had no doubt created himself. Uhura decided this was the perfect opportunity to touch up her self-given french manicure. Two officers were tossing a rubber ball back and forth. Kirk was leaned back in his captain's chair, looking to be in deep thought over something. When an officer would come to him and ask if there was anything that needed to be done while they waited for the ship to be finished being restocked, he would simply shake his head and wave his hand dismissively. Clearly, he did not want to be interrupted.

"I got it." He suddenly said, thought not loud enough to really attract much attention. Even though there was silence on the bridge, nobody bothered to look at him or acknowledge that he had said anything.

"Mr. Spock..." the Captain started, swiveling the chair over in Spock's direction, who was hunched over his panel. The Vulcan looked up over at him as if to say, "Yes, Captain?" though he didn't actually voice it.

".....how do you make antifreeze?" Kirk asked with an arched brow, leaning his elbow on the arm rest of the chair. Before Spock could even open his mouth to answer (which would have totally ruined the joke, by the way), Jim finished, "...you take away her blanket!"

This joke elicited a couple chuckles from utterly bored-out-of-their-minds crew members, Chekov and Sulu included, but Spock.....Spock just didn't laugh at all.

"Captain, I do believe that antifreeze is made from methanol, ethylene glycol, and propylene glycol. I don't remember there ever being blankets in such an equation."

This was getting ridiculous.