Have a Little Courage
Halloween. It was a holiday meant to be filled with fun scares, all sorts of creative and crazy costumes, and the best thing ever for someone Teddy's age—free candy! Unfortunately, the young corgi wasn't really much of a Halloween fan, and for the entire month, he would feel nervous, on edge. Seeing everyone and everything decorated with monsters and witches stirred up deeply hidden memories. Memories of things that had happened to him before he was found by his Uncles. Monsters were real. They were real and while there hadn't been any sign of that sort of trouble in years, they were still out there, lurking in the darkness. 
So the idea of running around half the night, dressed up as one of those foul creatures, and spooking the heck out of other kids was not something that Teddy wanted to entertain, even if the end result was a pillowcase full of free junk food.
But, it was alright! So long as he was able to spend the night at home having fun—playing games or maybe watching silly movies, he was happy, and this year would be even better than the last few, because Courage was going to be over to keep him company! Well, technically, the pink dog would be going over to babysit (as his Uncle Muta would be taking Alex trick-or-treating and Uncle Baron would be working in his study for the night), but he was excited either way!
The corgi had even been given special permission to stay up all night, or at least as late as he could, to spend as much time with Courage as possible and watch all of the 'Halloween' movies that he could handle. Maybe the movie idea wasn't the smartest, with his monster-fear, but there were plenty of cute Halloween movies that they could choose from. Ones that wouldn't scare him at all.
It was early evening when Courage arrived, just as Muta and Alex were heading off, and with a bit to 'have fun', the two were left to their own devices for the night. First, they made a nest of sorts, just in front of the couch. It was made up of all the extra blankets and pillows that they could get away with taking, propped up against the couch and around the area they'd be sitting. A large bowl of popcorn, bottles of water and juice, and even a few small bags of Teddy's favourite candies (sour watermelons and gummy worms) were out for the canines to enjoy.
Courage was the first to take a seat in their nest, having set up the DVD player with the first of their movies, Halloween Town II, hoping that it was cute and cub-friendly enough to not frighten his young friend. Teddy crawled into his babysitter's lap, leaning back against Courage's bare chest. Thanks to his small size, even at the age he was, Courage was able to comfortably hold onto him, arms wrapped around his belly, his own head resting atop the corgi's.
The movie wasn't one that Teddy had seen before, and he was doing alright with it... up until the evil warlock announced his plan to turn all of the humans into monsters. Courage felt the young corgi tense at the scene, but hoped he'd be alright knowing it was just a movie. Then came time for the spell to actually be cast and the humans panicked... and Teddy started to as well, whimpering softly as he tried to hide his face. Courage began to rethink the choice to put on any Halloween movie at all, and knew he had to do something quick.
He didn't want to move Teddy and alarm him further, but that meant he also couldn't turn off the movie (the remote had long since been lost). Turning it off would also leave them in complete darkness, which wouldn't do either of them any favours either. The gears in his mind turned as he rolled through possible ideas...
There! Courage couldn't hold back his grin as the perfect idea hit him. Oh, he knew exactly how to distract Teddy, and he felt a little silly for not thinking of that first. It had been a while since they'd had the privacy to have some... adult playtime, and if he was being honest, there was a itch that he'd been wanting to scratch that his own paws couldn't quite help with. He just had to hope that the corgi would be up for that type of distraction.
Pink paws took hold of Teddy's round, soft belly, giving it a squeeze that he knew would get the pup's attention. Almost immediately, Teddy relaxed, and with another gentle squeeze, the pup let out a hum of contentment. Taking that as an invitation to continue, Courage started teasing his little friend in all the ways he knew the pup loved.
He rubbed over his young charge's belly, up over his sensitive chest and down again, groping and squeezing the pudge. Thumb pads grazed the corgi's brown nipples, and Courage had to hold back from giving them a good, hard tug. This was meant to be a distraction, so he needed to take his time, get Teddy really worked up before he got rough.
Thankfully, he was well practiced when it came to self-restraint, even if his red canine cock was twitching and making it's way out of it's sheath already. Just being able to touch his young friend this way excited him more than it probably should have, and the cute little noises, the 'mmms' and 'ahhs', little groans and huffs were music to his ears. Every sound sent a jolt of excitement straight to his cock.
“Feels good..” Teddy mumbled, squeezing Courage's thighs in his paws as he felt his own loins stir, every touch absolutely wonderful. One pink paw drifted down and over the dinosaur briefs that Teddy favoured, grasping the hardening length and fuzzy little balls through the fabric. “Mm..”
Courage's other hand drifted back up to Teddy's chest, and he gently pinched one nipple. It made Teddy's hips twitch upwards into Courage's paw, pleasure running all the way down to his toes. Further encouraged, getting exactly the reactions he wanted, Courage squeezed a little harder with the paw on the pup's boyhood, thumb dipping into the waistband of the briefs. “K-keep going..” Already the pup's breathing was heavier, and he reached down, tugging his briefs down to his knees to allow Courage better access.
Lowering his head, the pink dog stuck out his tongue to lap at the other hardened brown nub on the corgi's chest, slowly stroking the pup's little pink cock. This was all it took to make his little friend cum, hard, but it wouldn't be the end of their fun if he did. From their previous experiences, Courage knew it would just make him even more sensitive, more relaxed, which would make his plan go much easier.
Giving the pup's nipple a long, hard suck, he squeezed the little cock in his paw, and just as he knew would happen, Teddy came. His breath hitched and he clenched down on Courage's legs with his paws, shaking from the force of what would be his first, but not last orgasm of the night.
Courage continued to stroke the pup through his orgasm, though switched to suckling on the other nipple as he did. “C-Courage..” Teddy's paws took hold of Courage's own, and the pink dog ceased his actions, knowing that he was ready to go on. 
The corgi got onto his knees and turned so that he was facing his older friend, and little cream paws grabbed hold of blue boxers. Courage's own excitement was more than obvious, his boxers quite a bit more snug than when they'd first sat down, and not wanting to cause him any discomfort, Teddy adjusted them so that the thick red cock hiding inside popped out through the unbuttoned fly.
“You don't have to, y'know.” It was something he always said, but really, he knew how much Teddy loved to play with him, how much that cute little pup loved sucking on his drooling cock. He could swear he saw the corgi roll his eyes as he lowered his head, taking the tip of that cock into his maw. Courage let out a deep groan at the feeling of Teddy's hot, wet mouth on his most sensitive bits, leaning back as one paw made it's way into the corgi's soft, fluffy hair. 
Teddy slowly bobbed his head, licking and sucking, enjoying the feel of the shaft in his mouth, the taste of the almost excessive pre-cum that constantly dribbled out. If he could finish the older dog off like this, it would make his night, but he had a feeling Courage was heading in a certain direction when he started his teasing. That didn't mean he wouldn't enjoy every second of cock he was able to have in his maw.
Courage was panting, trying to keep himself steady as that paw began to grip Teddy's hair, feeling his orgasm approaching fast. Gently, he pulled Teddy off of his throbbing member, and back up onto his knees. “I think you deserve a treat for doing such a good job.” The corgi's blue eyes lit up and he grinned, allowing Courage to pull him up. 
Courage's paw slid around to Teddy's bottom, a single digit slipping into his already slicked up, prepped hole. He looked at the corgi with a raised eyebrow and the pup just grinned wider, shrugging. With a shake of his head, Courage slid in a second finger, wanting to be sure that the pup would be able to take him with ease. “What can I say? I kinda had a feeling...” Not that Courage had volunteered to come over just to fuck the boy, but he wasn't about to complain. “Mmf.. C-can you.. y'know..”
Impatient as always, Courage thought to himself as he removed his fingers. “Just let me know if it hurts, okay?” Nodding, Teddy lifted himself up, putting his arms around Courage's shoulders to keep himself steady as the dog helped him line up his bottom right where it needed to be. As the corgi started to lower himself, though, Courage stopped him, a sudden spark of... inspiration causing him to smile. 
“You know, Baron is just upstairs.” Teddy tilted his head, confused and a little impatient. “You can get kind of loud when I'm inside of you... I think we need to make sure you won't accidentally catch his attention.”
“What do yo--” The corgi was cut off as his own briefs were stuffed into his open maw. He let out a, muffled, yelp of surprise, but quickly caught on, moaning around the dampened fabric.
“Much better.” With that, he lowered the corgi's hips himself, pressing the tip of his cock into that warm little hole. He felt himself throb with need as he slowly entered the corgi, allowing minimal time for the pup to adjust as he fully seated himself inside, just above the knot. 
“Mmmfmm.” Those muffled moans twinged his stomach in the best of ways, and he knew then that he'd be keeping this little idea in his mind for the future. “Mrrrm..”
“More, pup?” Teddy nodded, trying to move himself along the length, but Courage kept control of him, sliding him up and down slowly, much too slow for Teddy's liking. It was torturous, for them both, but he wanted this to last. Every achingly slow thrust into that tight hole had him tightening his grip, breathing harder as he growled low into the corgi's ear.
It made the pup whimper, but he held tighter into Courage, burying his head in his shoulder as he tried to push himself down harder. So Courage let him—releasing those yellow hips so suddenly that Teddy slammed himself all the way down, crying out into his makeshift gag.
It would amaze him to no end that a dog that was so gentle and kind in his day-to-day life could be so... rough, so “mean” during sex, as Teddy had said, playfully, the first time they'd done anything. He would reassure the pup throughout each act of intimacy, but when those waves of pleasure started to run through him, it was a like a switch was flipped. That instinct, that need to mate, would bring out a sort of dominance that even Courage didn't know he had.
And Teddy loved every second of it, even if some of their more fierce couplings left him sore for a day or two following.
Another yelp escaped as Courage pulled almost all the way out and thrusted back in, hard. Brown claws dug into his back and he did it again, fucking up into the corgi's bottom with want, with need. “Gonna knot you.. fill you up just like you want..” 
With a bite into Teddy's shoulder, he forced his knot inside, the fat ball inflating to keep him secured as cum poured into the pup's belly. Teddy held on tight to Courage as he moaned and whimpered, his entire body tensing as he came for the second time, dribbles of cum leaking down between his legs. 
It took a few long, long minutes of twitching and groaning before Courage calmed down enough to lean back, panting heavily as he came back to his senses. Teddy drooped against him, plucking the briefs out of his maw before sighing out, content. Courage gently wrapped his arms around his young friend, rubbing his back as they relaxed.
They would be stuck like that for quite some time, but neither would complain. Being able to cuddle close like this after cumming that hard made their 'mating' all the better. 
Teddy let out a small yawn as he reached up to plant a soft kiss on Courage's muzzle, and the older dog caught sight of a wide smile. “I'd choose this over trick-or-treating any day.”