After Toothless became the Alpha, and Hiccup became the new chief, they both had more responsibilities now. Hiccup had to protect the villagers of Berk and spend some time with his long lost mother. While Toothless on the other hand had to look after the other dragons, infants, old, sick, and healthy. Toothless and Hiccup don't hang out much as they used to, and Toothless didn't have much company.

One afternoon, Toothless was exhausted from working so much and decided to rest a bit on an area that's northern from Berk where it's peace and quiet. The night fury found his spot, circled around himself with his fire, and positioned himself. He closed his eyes but not for very long. A figure swooped by and came towards him.

"Hello Toothless." It was none other than Cloudjumper.

"What do you want?" Toothless asked with his eyes still closed.

"Well I couldn't help but notice you're all alone here, is something troubling you?"

The night fury yawned and looked towards the stormcutter "Well... Hiccup and I have been drifting apart lately, ever since I became Alpha and he's become chief you know?"

"So you are alone then?"

"Yes..."

"I could keep you company."

Toothless looked at Cloudjumper with a bit of a confused look, Cloudjumper never exactly offered something like this before. "You'd do that?" Toothless asked

"Yeah." Cloudjumper laid next to where the obsidian dragon was and covered his wing over him. Toothless was confused at his sudden affection. "I also brought you this," Cloudjumper's throat shifted as he regurgitated a slimey pile of fish. "I thought you might be hungry."
Toothless devoured the fish Cloudjumper brought, because not only was he hungry, he enjoyed the flavor of Cloudjumper's saliva on the regurgitated fish.

"It's almost like you came looking for me on purpose..." Toothless suspected as he saw Cloudjumper's smile with his golden eyes staring back at him.

"Maybe I did, maybe I didn't. But it's lucky I did or else you've would've missed this." Cloudjumper closed his eyes and pressed his lips on Toothless's own.

Toothless was shocked as his body backed away but his head didn't. He'd seen Hiccup and Astrid do this all the time and wondered what did Hiccup meant by it being "magical". But now that it's happened to him so suddenly, he can't decide whether it is magical as Hiccup said or disgusting seeing as it's coming from the one dragon he'd least expected would do this.
Cloudjumper broke the kiss and looked at Toothless in a lustful way, seeing the impact it had on the little dragon. It took a moment for Toothless to process what just happened. He shook his head furiously, blushing, and looked at the bigger dragon angrily.

"WHAT WAS THAT FOR?!" The night fury yelled.

"Why it was just how the humans represent their affection, I wanted to try it on you~. It was rather nice I must say, I can tell you enjoyed it too." Cloudjumper had answered ever so calmly.

"EXCUSE ME?!"

"Calm down my little kitty~ you shouldn't be so hot headed about this." Said Cloudjumper as he nuzzled Toothless.

'my little kitty'?! Toothless thought as he let the stormcutter nuzzle him.

"Well what I don't understand is why you're doing this to me!" Toothless exclaimed.

"It's simply because I love you." Cloudjumper had snuggled Toothless closer to him as Toothless found himself purring at Cloudjumper's actions

What's wrong with you Toothless?! He thought to himself Don't be fooled! He's trying to play with your mind that's all... but... it is rather nice.

Toothless thought about it and realized that no other dragon seemed to care as much as Cloudjumper did. He realized that Cloudjumper was always there for him, especially how affectionate and considerate he was to him at his time of need. Maybe this dragon is supposed to be the one that will never give up for him and will stay by his side no matter what. Maybe this dragon felt as lonesome and didnt want him to feel the same no longer ever since his species of Night Furies wiped out and Hiccup had and will eventually move on.

Cloudjumper was rather surprised to see the smaller dragon snuggling back the affection, and looking up at him with his emerald compassionate eyes. Cloudjumper smirked and said "So you're giving in?" as the stormcutter licked the night fury's forehead and heard him pur with pleasure then licked the smaller dragon's lips as Toothless licked Cloudjumper's saliva from his lips and savored the flavor. Cloudjumper pressed his lips on the night fury's again but Toothless welcoming him instead. The stormcutter had pinned down the black dragon on the ground as he pushed into Toothless's mouth as the two tongues battled for dominance.

The 2 dragons had eventually stopped as they nuzzled each other and pressed foreheads. Cloudjumper whispered to the night fury the question that would change everything.

"Toothless...? Will you be my mate?"

Without any second thought, Toothless already had his answer. "Yes!" Toothless exclaimed as he repeatively licked a joyful Cloudjumper. They purred and nuzzled until the sun had went down.