Direct Approach
Recent events have freed up some time, so this is my attempt to come back after so long away.
There's not too much in this short piece, just a pokémon making peace (and then some) with his trainer. I'm a bit rusty, but I think I did just fine here.
John stirred from his sleep, a little annoyed to have heard knocking on his door. The room service people sure were pushy! It didn't help that they weren't addressing any actual problems, like his room's lack of heat. Best get it over with, then I can get back to sleep. He shivered as the cold air rushed to greet him and quickly threw on his robe.
"Be right there!" he called out. John rubbed his eyes and attempted to appear as calm as possible. Instead of a guy in black formal clothes, it was his kommo-o, Kin, standing on the other side. The sight of him startled him awake.
"Uh..." John didn't know why, but he couldn't help but feel apprehensive about him. He seemed docile enough, but he couldn't shake the feeling that the dragon-type was secretly scheming against him. He then remembered that he was supposed to be in his poké ball downstairs. "Something on your mind?"
The kommo-o simply stared at him with his unreadable expression. Whatever was on his mind, John was not going to get a confession about it due to his silent mannerisms. Uncertain, he took a step back, and to his surprise, Kin nudged him backwards.
"What's goi--" He trailed off when Kin followed him inside and shut the door with his tail. The dragon-type locked the door, then pulled him against his chest. John shuddered when the comparatively warmer body pressed against his own, dispelling some of the cold. Suddenly he was picked up and dropped back onto his bed. Kin threw his trainer's robe to the side and crawled over him, draping the blanket over both of them.
"What's this all about?" John finally asked. When he didn't get an answer, he tried again, only to be cut off by a surprise lick. He lied there stunned as the kommo-o proceeded to kiss with him as much as he could, his arms pinned to stop any resistance. His heart began to race from both his rapidly depleting air and the notion that this was what Kin was thinking about the whole time.
As one of those claws let go of his arm and moved downward, he thought back to the first time they met. Kin had been a little jangmo-o at the time. He had wandered into his camp and crawled into his sleeping bag while he was asleep. After the initial surprise, the two of them had gotten along with little issue. Now the reclusive-ness he displayed when he had evolved made sense.
The feeling of his underwear being torn off along with scales against his inner thighs brought him back to reality. John looked up at the dragon-type, and for the first time in a long time, Kin was smiling at him. He didn't know whether to be happy or afraid at this point. The kommo-o pulled his trainer up and was about to kiss him again when John raised a hand, getting him to pause.
"Kin..." he began hesitantly. John did not completely feel the same way towards him, but flat-out saying as such didn't seem like a good idea, especially since things have gotten this far already. He leaned against his chest and shut his eyes, trying and failing to relax. "I'm... not sure about this... but I trust you." Gently, the kommo-o spread his legs and pressed his member between his trainer's cheeks. John winced and held on, trying not to scream as he was slowly impaled, not wanting to wake the others. Even with Kin taking his time, it hurt badly having something stick him there, but he endured, refusing to back out.
"K... keep going, Kin," he demanded when Kin paused. John fought back tears and gritted his teeth. His length was surprisingly warm, dispelling the cold with every inch until he could barely feel it anymore. When at last he felt his backside bump against Kin's scaly front, he let go of him and fell back in a panting mess, unintentionally making his tool slam into his sweet spot. John's vision blurred from the sudden influx of pleasure, and for a brief moment, he fainted. Kin was quick to catch him and set him down. The sight of his exhausted trainer nearly sent him into a rutting frenzy, but Kin held himself back. Instead, he lied on him and let him recover.
"That was... difficult," John groaned, "but worth it." He held on to his pokémon and nodded. Kin returned the nod and pumped in and out of his human. John no longer cared about making too much noise and began loudly moaning his pleasure, only encouraging the dragon-type to go harder. He fought a losing battle against the urge to faint again when he was turned over on his front, having never felt such ecstasy before. Mercifully, he had reached his limit, and in a few more thrusts, he blacked out as soon as he came.
The last thing he heard as he shut down completely was Kin's triumphant roar.
He let out a groan as he felt the warm rays of the sun brush against his face. Slowly, John opened his eyes and found himself in his rented room. There was an odd scent in the air, one that he knew wasn't in here a while ago, yet left him with a peaceful feeling. He was about to go back to sleep when he felt the bedsheet brush against his thighs.
Huh? A few more red flags went off when he shifted. Something was clutching his chest... he was hearing soft grumbling behind him... Perhaps most worrying of all was the fact that he felt strangely filled. He reached for his chest and felt two smooth, scaly arms over it. The events of last night came rushing back to him, and he immediately blushed, realizing it wasn't just some wild lucid dream.
"Mornin'..." John jumped when he heard the voice. It couldn't have come from Kin... could it? He sounded a lot happier than he usually did. "Thanks for last night. I really needed that." It had to have come from him; there was no other source.
"Kin, was that you?"
"Course I said that. Something wrong?"
"No, at least I don't think so... It's just... I know exactly what you're saying now." Kin turned him around and nuzzled him. It was strange seeing something other than apathy on his face, but welcomed all the same.
"So? That isn't a bad thing." He really was understanding exactly what was being said. It surprised him that his kommo-o was much more vocal than he thought. "The others would definitely be happy to hear the news."
"W-wait! We can't just tell them about what we did."
"They already know. In fact, they put me up to this. Besides, even if I didn't say anything, they would find out instantly." John froze in embarrassment, his mind already working out how things were going to be from here on out. If what he heard was true, they were going to be all over him. Then there was the matter of how his family would react if they heard about this... "Fear not, you belong to me first, and they know how I can be."
"I'm not sure how to take that... but I believe you." Somehow, he knew things were going to be all right. He leaned back into his pokémon's grip and went back to sleep.