Clients came to Stiles for a lot of things. He was an experienced handler, was well known and respected in the community. Everyone knew that if they had a problematic pup, he was the one to bring them to. Most simply lacked discipline. New owners were often too over eager with them. So excited to simply have a new pup in the home, they forgot to establish firm boundaries, didn’t know how to discipline.
It usually only took a month or so. The owners had to be diligent in scheduling their sessions, though. Lapses in training could just lead to confusion and frustration and acting out on the pup’s part. He was something of a savant with them. He hadn’t been in the business too long-- most people still called him kid-- but he’d never had a problem he wasn’t confident in handling.
Sometimes there were bad owners. Sometimes there were rotten pups. But that could happen with anything, to anyone. Not everyone who came to him was really looking for the help that they said they were. They wanted quick fixes, or for him to establish unhealthy dynamics. Pups weren’t meant for pure obedience, nor utter decadence. It was a give and take. An equal relationship.
His latest client was headstrong-- the pair of them. His owner clearly had bought the pup as a luxury item and didn’t spend as much time with him as was needed. And the pup? Well he needed some breaking in. Combative and spoiled and arrogant. He was definitely one that would test even Stiles.
Today was their first solo session. Jordan-- the owner-- dropped the pup off on his lunch break and wouldn’t be around to pick up Derek until after work. Stiles didn’t usually offer kenneling services, but it was the only way he could keep them coming back and he could tell if anyone needed this, it was the two of them.
So he’d cleared his schedule, slipped on his most comfortable combat boots, his real leather gloves, chaps, and harness-- the ones that wouldn’t chafe through extended use. Derek was… a handful, and he was sure that they wouldn’t just be doing a usual lesson and then the pup would calm down. This was going to be an all day affair.
He hadn’t had a pup himself since… college. A lot of frat boys and city council members’ sons like to “take a ride on the wild side” and paid well for him to take control away from them, steal away their stress for a while. He wasn’t sure what Derek’s interest was, but the man made for one beautiful pup.
Cool, bright green eyes. Built like a brick shithouse. Quite handsomely hirsute. Stiles was amazed his owner had found a cage that fit his low hanging nuts and fat cock, found amusement in the dexterous way Derek could manipulate the rubber tail plug in his ass to show a whole host of moods besides excited. They were an attractive couple on paper.
But Jordan was clearly more focused on the image of it all-- expensive gear, memberships to exclusive clubs, an entire “play pen” for Derek in his apartment. And Derek was smart enough to know that, so he acted out. Stiles had seen the pictures. Wrecked equipment. Bite marks. Piss puddles. Hallmarks of an pup just begging for attention.
Stiles just had to teach him the right ways to ask for it. Derek had started following some simple commands for him. “Place” and “Come” took a little wheedling, but not much. “Watch me” went over simply well, but was met with a certain wariness. “Sit. Heel. Stay” were all on the agenda still. Derek did not like being controlled that way.
Stiles had tried incentivizing him in every way imaginable and they’d yet to make progress. So today they were trying something new. Maybe Derek just needed a… firmer hand. “Derek. Derek! Watch me.” Stiles didn’t bark at him, but kept his tone assertive. Derek had been pawing at something off the side of the room and glanced up at him, but then went back to his business.
Stiles tried again, this time with a clicker. He stood his ground. He didn’t move closer or raise his voice. “Derek, come.” Derek started to meander over, but clearly wanted to make a point that he was doing it almost more out of sheer boredom than anything else. Stiles raised a brow at him, tsked lightly. Derek just shook out his head.
“Derek, heel.” Derek stared up at him. “Derek, heel.” Derek huffed at him, breathy but bordering on aggressive. “Derek, heel!” Derek bared his teeth and barked. Stiles’ expression did not change. He did not bare his teeth back, nor did he yell. But with a flick of his wrist he snapped a riding crop against Derek’s backside-- the crack of the leather hitting his bare flesh a shock in the otherwise quiet room.
Derek’s eyes widened. His bark died in his throat. Stiles watched his cage jump. They stood in silence for a moment before Derek started growling, pouncing at Stiles’ ankles and trying to pull at his chaps. “Derek, sit! Derek, I will spank you again.” Stiles gave him a moment to behave before bring the crop down again and again.
Derek’s skin started to redden across a single spot. His meaty ass bounced and quivered with each strike and on his second lashing he made a high whine. He stopped growling, but he didn’t back up. He pressed his face tighter to Stiles’ feet and arched his back, presenting his tail and naked rear. When Stiles didn’t spank him again, he started to wriggle, made little, low noises.
“You know, Derek. Most people get into pup play for the praise. They like following orders and being rewarded. They want the unconditional affection.” Slowly Stiles ran the crop over his back, circling the dimples at the base before pressing into his ass crack and then across the cheeks. “Not that you’re doing it wrong, just that it should have been something you discussed with your owner initially or at the least disclosed to me in our pre session interviews.”
Derek whined at his feet, pushed his ass up higher. Stiles relented and smacked him once, twice, three times in quick succession. Each smack of the crop made his cock plump up, his breath come a little thinner. Derek’s cock couldn’t get hard in his cage, but pre had started gathering on the metal and was slowly dripping its way down the fixture and making spidery strings to the ground.
“You’re a bad boy, you know that?” Derek whimpered and Stiles spanked him again, relishing in the way an outline of the crop was starting to imprint in red. “You’re stubborn” SMACK “You’re ill tempered.” SMACK “You’re selfishly guarding your own interests and creating toxic dynamics with the people around you.” Derek looked up and Stiles held his eyes as his arms flexed and he bit the bottom of his lip with the force of his blows. SMACK SMACK SMACK.
Derek’s eyes watered and his inner thighs shook. His ass was a bright, hot red and his balls had drawn up tight to his body. “You’re going to have to trust me if you want to improve things. I’m not here to hurt you. Unless you want me to.” Stiles held Derek’s chin as he moved the crop to smack first against the delicate insides of Derek’s thighs once each before swatting sharply at his cock.
Derek cried out and thick, pearly cum gushed from his cage as he came, soft. Stiles gently rubbed at his dick head with the crop, letting him get some measure of friction as he rode his orgasm out. Then, tenderly, he lifted Derek’s hood away and brushed away his tears with a thumb. “Was that alright, pup?”
He bent down to look Derek square in the face, using his other hand to brush his hair back, wipe away some sweat. Derek took a moment, but then nodded, still too overwhelmed to speak. Stiles got into a squat to hold him, shushing him and petting through his hair as silent sobs wracked his body a while. Derek dug his face into Stiles’ nape, curled into him even though his frame was much bulkier.
And then, when Stiles went to pull away, kissed him. That was a major flag, a big no in his line of work. Not only would Jordan be quite unhappy, but this really wasn’t the way he should start a relationship. Even so, he wasn’t perfect all the time either, and so he kissed back, humming into it.
When Derek pulled away they were both a little gobsmacked-- red cheeked and dodging eye contact. “That’s… a bad boy,” Stiles lamely admonished.
Derek snorted, grinned at him that roguish, crooked grin that was entirely too dangerous, and let out a naughty, playful little woof.
They were both bound to get in a lot of trouble. For once though, Stiles didn’t mind.