Written in response to this prompt: I want McCoy to be a reluctant mentor to Chekov (non-sexual)
Maybe Chekov goes to McCoy for advice on how to get a guy to notice him (can be Sulu or Scotty)
Kirk/Bones, with bonus Jim teasing Bones about Chekov's hero worship, then equally jealous that Chekov didn't come to him!

There were times when Leonard McCoy wished he had any job other than Chief Medical Officer on The Enterprise. Dealing with an outbreak of Andorian influenza that affected 87% of the crew had been one of those times. Telling Lt. Flores that the alien pregnancy she had "contracted" on an away mission would have to be terminated as it's life wasn't compatible with her own had been another.

But this had to be the most miserable of all possible reasons to not want to be CMO. Bubbly, innocent little Ensign Chekov was sitting across from him in an exam room, after having requested vaccinations against all known STD's, and asking for advice about SEX.

There would not enough alcohol on the entire ship for him to forget this tonight. Maybe not enough in the whole universe. Damn kid!

"So, Doctor, if I like someone and want to be… with them, how can I tell them this?"

"Dammit boy! Why don't you go speak to Counselor Cheng about this? I don't do the emotional stuff."

When Chekov blushed, his freckles actually vanished. Too bad it didn't stop his mouth.

"I tried to talk with her, but it was too… um, awkward? I cannot talk to a woman about other men."

Ah crap. Not only had Chekov decided to lose his virginity, but he had a crush on a man here on ship as well. Sulu and Scotty seemed the most likely candidates, although what the kid saw in either of them McCoy didn't know.

Damn! He hoped the boy didn't have a crush on Jim. It was well known on ship that Jim would hump a rock if opportunity presented itself, but Leonard didn't like the thought of Jim being the kid's first. He had a feeling Chekov would spend the next five years following the Captain around like a puppy if he did.

McCoy continued preparing the multiple hypos needed and tried to figure out who the kid was aiming for.

"So the guy you like? Do you see him a lot?"

"Da. Everyday. So I don't want to make things uncomfortable in case they do not like me back."

"Hmm… Do you spend time together outside of work."

"Da, we "hang out" a lot. I think he likes me, but I wish to know for sure…"

Okay, that ruled Jim out. It sounded like Chekov was interested in either Scotty or Sulu then.

"Look kid, I don't know what to tell you. Either this guy likes you or he doesn't. If you're friends, I'd be surprised if he isn't happy to be friends with benefits. If you don't just like this guy but you actually love him though? You need to tell him that from the beginning, and you can't pussyfoot around. Tell him you care about him and let what happens happen, alright?"

"It vill be hard to say these things."

"Love is hard kid. Get used to it."

Chekov looked thoughtful while McCoy shot the hypos in his neck and ran a few scans. He then smiled and thanked the doctor for his "wise advice".

Later that night, Jim showed up in the doctor's quarters and laughed to see a ring of empty glasses on the table and a half empty bottle of scotch. "Bad day, huh?"

The older man gave Jim a mournful look. "You have NO idea!"

Jim smirked, "Hey, I saw Chekov and Sulu making out hot and heavy in the back of the rec room. Had to tell the boys to get a room. That wouldn't have anything to do with your dark mood, would it? I was kinda worried he was mooning over you, considering the way our navigator had been hanging around you lately."

"Sulu huh? Figured it had to be him or Scotty. I had to update the kid's STD preventions and he kept asking advice about what to do if he liked someone."

"Hey! Why didn't he ask me that stuff? I'm the king of relationships! I'm insulted!!!"

McCoy rolled his eyes in response. "You're the king of one night stands. I have a feeling our little Russian wants more than that with Sulu."

A moment later, Jim Kirk had maneuvered himself onto McCoy's lap and was kissing his breathless. "I don't know about that. I've managed to keep you around for a few years now."

"Hn. Ours in hardly a romantic relationship."

"Hey, you told me from the beginning that if we did this it wouldn't be a one night thing. I'll be here as long as you're willing. Tell me that isn't love?"

"In that case, scrounge me some actual whiskey for tomorrow night. I have a feeling I'm going to be dealing with an insanely happy Ensign Chekov and I'm going need something stronger than scotch to deal with whatever he tells me about losing his wirginity."

Jim kissed him again and pulled him towards the bed with a simple, "I think that can be arranged."

The next day, he was right, and when Jim showed up at his quarters with bottles of both whiskey and bourbon, McCoy decided that his lover was a good man to have around.