(A/N) I'm gonna put the warning here now. Sad chapter. Grab your tissues. That's all I'm gonna say because it is hard to write myself.
It was early fall when Hiccup and Astrid started to notice that Toothless was not as active as he usually was and that his appetite was slowly decreasing. He was being picky about what he ate as well and Both Luna and Stormfly began keeping their distance from him. This was concerning to Toothless' owners so Hiccup and Astrid took Toothless to the vet and they found out that Toothless had kidney disease and arthritis as well and that he would have only an estimate of a few more years left to live, so they decided to make what little time they have with Toothless the best they could, creating a bucket list for Toothless for things they want to do with him before he would pass away.
During this time they took Toothless on all sorts of trips and adventures all around the country and during this time Toothless and Luna decided to mate and they found out that she was pregnant with a litter of three puppies which they decided to keep and have trained as service animals for Hiccup and the twins Helka and Asmund. Even though Helka and Asmund didn't understand what was happening to Toothless and why they were doing this, Hiccup and Astrid tried their best to explain to them why. Even then it was hard because Toothless had been apart of Hiccup's life since he was about four or five years old and had been at his side since.
Through all they'd been together, fighting what life had decided to throw at them, it's going to be hard saying goodbye to his best friend when the time came.
Some of the things the Haddock's did to make Toothless' last day memorable were taking a road trip across the country and swimming in the ocean, making his favorite food even though he didn't always eat it, taking a lot of pictures and creating a digital scrapbook of all the memories they had shared throughout his life. They had his paw print encased in plaster as reminders of his great life as well.
Then one day when Toothless went to take a nap he didn't wake up. When Hiccup tried to wake him up for dinner, the dog didn't rouse, so that was when he knew that his best friend had passed away. Hiccup broke down against Toothless like he had many times when he was little and in pain. That was how Astrid found him and she realized that Toothless had passed away and sat down next to him and just hugged her husband as he mourned his longest best friend.
Later, Hiccup and his wife made all of the arrangements to have Toothless cremated. They called their family about what happened and they also had to tell their children that Toothless had passed away. Once they get Toothless' ashes they placed them on the fireplace mantel next to a picture of him and copy of his footprint that they had cast in plaster. Later that night Luna had her puppies. They decided that the black one named Ruthless who looked like Toothless but with blue eyes would go to Hiccup, the white with black ears and blue eyes little one named Midnight would go to Asmund, and the other white one with green eyes and black paws and ears-Eclipse-would go to Helka.
It took a few weeks before Hiccup could think of his best bud without wanting to cry. He began suffering more migraines as the stress he'd been through affected his side effects induced by his Neurofibromatosis diagnosis. He took off a couple of days from the forge when the migraines and nausea got too bad, and Astrid brought his new puppy to him in an attempt to help form a bond that once was with the next generation of Toothless' family line.
"Thanks babe. How are the k-kids d-doing?" Hiccup stuttered out as he tried to hide his eyes in the pillow, the simple sound of rain on their bedroom window setting his very brain on fire. Astrid set the black, hyperactive puppy next to her husband's shoulder, hopeful that Hiccup would somehow find a connection which could help him in these hard times.
"You worry too much you dork. They're just fine. A little upset about the loss, but they absolutely adore Midnight and Eclipse." Astrid rubbed comforting circles in Hiccup's back who sighed in relief at the soothing contact. She chuckled lightly when Ruthless cooed curiously, before growling in concern as he pawed his way at Hiccup's hair. The puppy had only recently opened his eyes and was still weening off of his mama, though he was full of energy despite only being about the size of Hiccup's own hand. Little thing didn't even had claws or teeth yet.
"I think he's worried about you." Astrid said with a content sigh
when Hiccup let out his own growl because Ruthless had pulled his hair back and let light into his sensitive eyes. The puppy's tiny barks weren't helping either.
"He's too hyperactive. Keeps letting light into 'm eyes." Hiccup mumbled in frustration. Normally he didn't have this kind of attitude nowadays, but Astrid knew he was just in pain and irritable. He was also grieving which was just the icing on the cake.
"Maybe he can help take your mind off of the headache." Headache was an understatement Astrid knew, but she wanted to add some light to the mood.
As if understanding what she was saying, Ruthless stopped barking and shoved himself in the crook between Hiccup's left elbow and his shoulder so his tiny black body was pressed against his owner's left cheek. Hiccup sighed at the warm contact and something other than his hair covering his eyes so they didn't burn at the light. Ruthless' soft breathing also helped keep his brain off of the irritating rain outside which was making his ears throb.
"I guess. Th-thanks little guy." Hiccup whispered as he was already beginning to fall asleep.
He dreamed of Toothless only to wake up to Ruthless, but somehow the puppy being next to him and the now soothed migraine made it easier to let go of the bond that once was and begin building on the one that was now just growing.