How to Train Your Human's Asshole

Hiccup and Toothless have been official mates for a few weeks now, and while it's been going great there is one thing that they have yet to accomplish in their relationship, something that Toothless had accepted would be a challenge but figured that Hiccup would work on it at some point.

Hiccup has yet to be able to suck or get fucked by Toothless properly.

Now, again, this was sort of to be expected when a scrawny human decided to become mates with a dragon that's at least twice the size of him but still, Toothless didn't really feel like a true mate by not showing Hiccup the same amount of love and passion that he had been showing him.

Now, don't get Toothless wrong, he loves sucking and getting fucked by Hiccup. Feeling Hiccup's small human cock drill into his ass or slide around his mouth with all of his efforts is like snorting dragon nip to him, and while Hiccup does offer his arms to service him while he's doing so, it's just not the same as feeling his human's ass or mouth wrap around his dick like a tight sleeve.

Also, it's not like it never came up. Toothless has mentioned on a few occasions on how he would like to fuck Hiccup but Hiccup always comes up with some sort of excuse like he's just not in the mood for that.

Toothless suspects that the main reason why Hiccup has been so reluctant is the fear of Toothless splitting him in half due to the very noticeable size difference. While that did concern Toothless as well, he also knows that his Hiccup is stronger than he appears and can likely do it if he just tries.

At one point, Toothless considered to just deal with it and maybe, eventually, Hiccup will be able to take more and more of the foot and a half long cock minus the knot, but no, this was something that needed to happen sooner or later, he just needed to figure out how.

Then, one day, he gets an idea. He has Meatlug and a few other Gronckles spew up long rocks in various sizes and lengths, ranging from the length of a pencil to just under Toothless's own length. Of course Meatlug did wonder what he needed these rocks for but all Toothless told her was it was for a special project.

Once the rocks were cool and set, Toothless takes them to Hiccup's house. Hiccup himself was setting up for the next day's training lesson, so that bought Toothless just the right amount of time to hide the rock dildos and make his way to the kitchen.

He could hear Hiccup walking up the steps, the clink of his metal leg was indistinguishable, so he decides to hide in a dark corner of the house. It was almost dark, so it was a perfect time for him.

Hiccup opens the door, looking exhausted from a long day. Out of the corner of his eye, he could see the glow of Toothless's eyes and chuckles. "You know, your eyes give you away right?"

Toothless groans. "Thanks for the note. How was your day?"

Hiccup shrugs. "Not too bad. Snotlout and the twins were supposed to help me, Astrid and Fishlegs but they decided to use the day to see which dragon could hit a target from the longest distance."

Toothless chuckles. "Aw, my little Hiccup is all tired. Guess that means you're heading straight to bed? Don't feel like…doing anything tonight?"

Hiccup sighs and shakes his head. "Toothless, have I passed up a chance to mate with you yet?" He motions his head to the stairs and Toothless excitedly runs up the stairs and waits.

Hiccup followed close behind and once he entered the bedroom, he could see Toothless lying on Hiccup's bed and could already see the red of Toothless's member showing. Hiccup chuckles. "You horny bastard."

Hiccup takes off his clothes as he makes his way to the bed and shows that he too was erect. Toothless jokes back, "You horny human."

"Yeah yeah, less talking, more mating." Hiccup brings Toothless's head closer and starts attacking him with kisses. When they first started mating, kissing was something that Toothless wasn't quite used to doing but over time he learned to like it.

Hiccup then reaches over and grabs the tip of Toothless's cock in his small hands and gives it a few strokes. While that did feel good, Toothless realized that wasn't what he wanted to accomplish that night. He pulls away from the kiss and says, "Hold on, there's…something I need to talk to you about."

This gets a worried look from Hiccup as he asks, "What is it, love?"

Toothless rubs the back of his neck with his tail before saying, "Hiccup, this time that we've been spending together as mates has been the greatest of my life. However…there's something I still need from you and I think you know what it is."

Hiccup had to think for a moment before he realized what Toothless was talking about. "You want to fuck me. Don't you?" Toothless nods, making Hiccup sigh. "Look, the problem with that is plainly obvious. You're a full grown Night Fury, I'm the smallest teenage human in the world, I just don't see how that would work out."

"I know." Toothless replies. "Which is why I decided to help you out a little." Before Hiccup could respond, Toothless dashes off of the bed and to the closet where he opens the door, revealing the rock dildos inside.

Hiccup's initial reaction went from shock to confusion to realization. "Toothless. A-are those for me?"

Toothless nods. "I know you want to take my cock as much as I do, and I want to do whatever it takes to make that happen."

Hiccup didn't know what to say. It was true that he had considered trying to take the big dragon dick which, at that moment, was staring right at him, fully hard and twitching in need of being put into something.

Of course his biggest fear with that is that Toothless would end up poking right through him, however Hiccup also trusted that Toothless would never suggest this if he thought Hiccup was going to get severely injured from this. So, he smiles and hugs Toothless tight while saying, "Thank you, love. Let's do this."

Toothless smiles. "That's all I need to hear. Alright, which one do you want to start with?"

Hiccup looked at each dildo. There were eight of them, the shortest one being about 6 inches and the longest being about 15 inches, a few inches shorter than the thing dangling between Toothless's legs, and each one appeared to be an inch or two longer than the last.

Hiccup picks up the second shortest one which was about 8 inches. Toothless comments, "Alright, I'd say that's a good start."

Hiccup nods before realizing something. "Uh, one second." He reaches into one of his drawers and pulls out a bottle of lube that he opened and slathered some of the gel-like substance onto the dildo.

Hiccup lays the dildo on the floor and after lubing himself up, he positions himself and proceeds to sit down. Being that it's a rock, the dildo felt quite cold as it slid up his anus, but at the same time it felt quite smooth and enjoyable.

Hiccup takes a deep breath before sitting down further, causing more of the rock dildo to slide up into him until before he knew it, his ass had hit the floor. Toothless's eyes widen from impression. "Wow, that was quicker than I thought. You sure you've never had anything up there?"

Hiccup grunts and grins while saying, "So I might have done this with other objects in the past. Tree branches, my bedpost, even the handle to Inferno, of course I gave that a good wash afterwards."

Toothless nods. "You think maybe you're up for something…bigger?"

Hiccup adjusts his position a little while saying, "Maybe, love, just give me a minute."

Toothless nods again before realizing something himself. "So, I think while you're doing that we can also give your mouth and throat a little bit of training. I don't know how you're plan-"

"Give it to me."

Toothless was a bit thrown off by this interruption. "Huh?"

Hiccup smirks. "What better way to practice than with the real thing?"

Toothless's eyes widen even more. "A-are you sure? I don't want to do anything that might hurt you."

"Just give me that cock of yours, you useless reptile." He says as he pulls the dildo out of him and motions to Toothless to give him the next one. Toothless takes a moment to mentally adjust to what's going on before he takes the dildo away and reaches for the third smallest one until Hiccup shakes his head. "Keep going." He says.

Toothless, again, was surprised that Hiccup was so eager to try something bigger, but he could see that look of determination in his eyes, the same look he got when he was making his first tail fin, so he grabbed the middle sized one, about 11 inches in length and hands it to Hiccup.

Toothless hands Hiccup the dildo but was still unsure if Hiccup was ready to put his dick into his mouth. Hiccup could see this worry, so he settles Toothless's mind a bit by hugging his head and giving him a kiss on the forehead before saying, "I trust that you're not going to hurt me. Not on purpose. I really do want this to happen, love. More than you know."

Toothless croons in understanding before lying down so that his cock is facing right towards Hiccup's mouth. Hiccup picks up the cock, feeling the weight of it in his small hands, and licks it a few times before slipping the tip into his mouth while also slipping the tip of the dildo into his ass.

Hiccup moans from the rock dildo in his ass but that gets muffled by the fleshy cock in his mouth. Hiccup takes a deep breath and relaxes his throat and anal muscles to allow him to take more of both the dildo and the cock.

Toothless was also moaning from feeling Hiccup's mouth finally wrap around the tip and first few inches of his cock. His initial instinct was to grab Hiccup's head and pull it further down but he didn't want to risk suffocating Hiccup, so he just let Hiccup go at his own pace.

Still, it felt really good. The part of his dick that managed to get inside Hiccup's mouth, which was only the first 4 inches at that point, felt the warmth of Hiccup's insides around it with a tight grip, making his large balls churn with seed that was almost aching to get released.

The taste of the pre-cum that Toothless was leaking sparked some strong emotions inside Hiccup. It was a little strange to say but the warm, salty fluid warmed his body up and allowed Hiccup to feel more love for Toothless than before.

Hiccup got halfway down the dildo when he had to pause to adjust himself and put some more focus on the cock right in front of him. He relaxes his throat muscles again and manages to slide two more inches down his throat, meaning that about a third of the cock was now inside him.

That, however proved to be too much for the small human as he coughed a few times on the cock and had to pull it out, causing him to lose his balance and end up taking the rest of the 11 inch rock dildo in his ass.

Toothless quickly got up and went face to face with him. "Are you alright, love?"

Hiccup coughs a few more times before saying, "I'm fine, babe. Just...bit off more than I could chew there." He kisses him to let him know he's ok. "It's ok, I'm sure with time I'll be able to take that thing in my mouth. Say uh, since I managed to get this dildo in, you mind handing me the next one?"

Toothless was surprised. "You want to keep going?"

Hiccup nods. "I want to really test my limit here and I think I can go for the next one. Oh but, could you help me get this one out?" Hiccup rolls over to his stomach with his ass facing Toothless.

"Uh...sure. Here" Toothless grabs the dildo with his tail and slowly pulls it out, getting lots of moans out of Hiccup and making his small human cock leak pre-cum onto the floor.

Toothless looks at the next sized dildo, about a foot in length, and pondered just giving it to Hiccup. However, something that Hiccup said earlier played around in his mind, something that edged him on a little to do something drastic.

Hiccup was waiting patiently for Toothless to put the next dildo in his ass when he could feel something looming over him and he could feel large paws pressing down on his side as well as something else that was large and fleshy poke his rear. He asks, "Toothless?"

Toothless leans his head down and says, "You said it yourself. What better way to practice than with the real thing? Unless of course, you don't think you can take it."

Hiccup looks back at the cock poking his backside and sees that it is certainly bigger than anything he had ever taken before, however, in that moment, all of the fear that Hiccup had towards having that monster inside him suddenly washed away. He kisses Toothless on the chin and says, "Do it, love."

Toothless nods and positions himself before gently pushing his tip inside Hiccup's ass. Hiccup was glad the dildos stretched him out earlier, because he was certain this would be nearly impossible otherwise.

Once the tip was in, Toothless pauses for a moment to let Hiccup adjust to the girth of his cock tip. Toothless's cock was about the same girth all the way down, except for the knot, with the tip being relatively thinner and a bit softer to allow him to get inside his mate's hole easily.

Once Hiccup felt himself loosen up a bit, he pats Toothless on the chin, signaling him to keep going, so he does just that. Toothless pushes a few more inches in before needing to stop, both to let Hiccup adjust and to show that he really does care for him and doesn't want him getting hurt.

Toothless glances down and sees beads of sweat dripping down Hiccup's face and his eyes were closed as he was trying hard to get used to the sensation in his ass. He wondered if they should stop, but then Hiccup opens his right eye and nods to him, telling him to keep going.

Toothless sighs before beginning to move his hips back a bit before pushing them a bit more forward, pushing even more of his cock inside Hiccup's ass. His dragon instincts told him to go faster, to really breed Hiccup like a female in heat, but his heart told him that that might just tear him a new hole so he kept going at a slow pace, letting his cock slowly sink further into the ass it was in.

Toothless could tell that Hiccup was slowly getting looser and that allowed him to go slightly faster, but still slow. He now had at least half of his cock inside of Hiccup's ass and continued to push in, letting the small human feel every inch of that large dragon dick spread his insides wider than any dildo.

Hiccup's body heated up from feeling the love that Toothless was giving. He wanted to show Toothless that same love back so he scratches him in his favorite spot under his chin, the one just above the sweet spot that makes him collapse because let's face it, he really didn't need a full sized dragon falling on top of him right now.

Slower and slower, Toothless pushes his cock further inside until, before either of them knew it, Toothless could feel his knot bump against Hiccup's ass cheeks, indicating that the whole main part of the dick was now inside of the human's ass. All 18 inches of thick dragon cock now nestled inside the tight ass like a Cavern Crasher in a crack in a cave wall.

Toothless had to admit he was quite proud of Hiccup for being able to take so much dragon cock. It made him wonder what happened to that talking fishbone that he saw when they first met. While Hiccup was even more proud of himself and glad that Toothless was able to share this love with him, made him feel pretty lucky to have such a passionate yet caring dragon lover.

Toothless takes another deep breath before starting to move his hips back and forth once more and starting to fuck Hiccup at a steadily increasing pace. Hiccup moaned and groaned from feeling the large dick in him which made his own small dick bob up and down while dripping pre-cum onto the bedroom floor.

Toothless's knot had popped out of his sheath at this point, but again he didn't want to put it in in fear of hurting Hiccup, so he just keeps fucking Hiccup at a pace similar to if Hiccup was another dragon but a bit slower.

However, that pace, combined with the tightness of Hiccup's ass, was proven to be just too much as Toothless thrusts one last time before his orgasm hits him like a herd of yaks, making him shoot cum deep into Hiccup's depths. Hiccup came with him, firing a much smaller load onto the floor.

The sheer quantity of Night Fury cum caused Hiccup's stomach to inflate a bit and since the knot didn't make it in, whatever cum didn't fill Hiccup's insides spilled out onto the floor, effectively shadowing the puddle that Hiccup made.

Once Toothless had settled from his orgasm, he takes a moment to let what just happened sink in. Finally, fi. na. lly, he was able to show his Hiccup just the amount of love that Hiccup had shown him several times in the past, and boy did it feel good.

He leans down and licks Hiccup on the face to make sure he's alright. When Hiccup opens his eyes, Toothless says to him, "Your ass is fit for a king. Throat could use some work though and maybe we can work on trying to get my knot in next time so you can experience all of me."

Hiccup smiles and kisses Toothless right on the lips before saying, "Like I always said, training can be tough but the results make it all worth it."