Five times Chekov almost lost his virginity and one time he did (originally posted here):

Warning: to the best of my knowledge, this fic needs no warnings. 

 1) "Wait a second," the Andorian squinted. Half naked and tantalizingly blue, he said, "How old are you?"


2) In retrospect, Pavel probably should have researched Klingon mating rituals before attempting to seduce one. Thankfully no one in the Infirmary guessed the source of his (copious) injuries.


3) "This is going to be so much fun, you have no idea," Gaila grinned, dragging Chekov by the arm as she opened the door to her room. 

Chekov managed only the briefest of glances into the promised land (he caught sight of two beds, one occupied by writhing figures, long and lean, a peek of what Chekov could swear was a pointed ear) before Gaila was rapidly back-pedaling, grin no less wide though considerably less-directed-at-Chekov. 

"Never mind," she said. "Room's occupied." 


4) First Contact with a new alien species dictated the deflowering of a virgin; something in their culture mentioned this was a signal of new hope and life, a renewal of sorts. Pavel looked up hopefully at this news. 

"Right," Captain Kirk said. "Can they actually tell if someone is or isn't a virgin?"

"No, sir," Uhura said.

Kirk smiled a filthy, filthy smile, aimed straight at McCoy. 


5) They were drunk and there were kisses, maybe they were more than drunk, there was that weird hazy smoke - 

there was a tongue in his mouth and he sucked on it -

hands were crawling up his chest, beneath his shirt, sliding up his back, tracing his spine

hands were reaching for his belt and

unclasping it 

and

slipping fingers 

inside -

"Okay, that's enough," a gruff grip pulled Chekov out of the comfortable lap he'd been grinding into. "This is the last time I let Jim take you on an away team, you always seem to find the nearest alien brothel."

Chekov didn't weep as Bones hauled him back to the Enterprise, but it was a very near thing. 


and the time he did) "Huh," Chekov said. "That's it?"

"What do you mean, 'it'?"

"I thought - it would be more - more."

Sulu growled. "I'll show you more."