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The New Pup

Chapter Text

Stiles picked up the ringing phone and pressed it to his ear. "Hello," he greated in a warm voice. "This is "Waggin' Tails Trainers", how can I help you?" Stiles had on his business voice as he propped his legs on the wooden office desk. Work had been slow lately and the thought of having a new pup to train made him excited with prospect.

"Yes, I have a friend and I was wondering if I could make an appointment for him by chance?" The man on the other side of the line sounded uneasy but at the same time, confident.

"Does your friend have a name?" Stiles asked absently.

"Oh! Yeah! It's Derek. Derek Hale. And I'm Isaac Lahey," the man- Isaac- replied.

"Well Isaac, is your friend Derek a pup in training?"

"Umm… yeah. I guess so. He has no real experiences but he gave me this number because he's too embarrassed to call himself. He's been looking into your… well services, and is interested." Isaac stuttered through the while thing. It was apparent that he was embarrassed to be making this call too.

"Ok. When day is Derek free? I can set up an appointment starting Thursday." It was now Tuesday and Stiles was already almost bouncing up and down with excitement over the new pup but knew it looked professional to wait.

"How about Friday? He's off work that day."

"That sounds good. Tell Derek I look forward to meeting him," Stiles told Isaac in an easy voice.

"Will do. Bye… I guess," Isaac said before he hurriedly hung up.

Stiles say back in his chair, face splitting with a smile. He couldn't wait 'till Friday.


The week passed slowly but around six on Friday a young, nervous looking man knocked on Stiles' door. He opened the door and motioned the man in. "Come in, come in!" Stiles beckoned the man back to the kitchen and they both took a seat at the table.

"You must be Derek," Stiles said with a warm smile.

"Yes, Sir," Derek nodded. He had dark brown hair and bushy eyebrows.

"You must be here about the training then, I assume?" Stiles liked to get down to the point. There was no use in small talk.

"Yup," Derek responded, looking down at his hands awkwardly.

"It costs $50 a day. I have a weekly discount of $320 if that's more what your looking for. I provide all equipment and food for however long you stay and we train every day. You will be in the dog mindset constantly so you need to think this through carefully before making a decision. You can safeword out any time but there are no refunds." Stiles laid it all on him at once and Derek had to think about it before responding.

"I was thinking about staying a week, maybe adding on extra days if I want." Derek responded slowly, sounding a little more sure of himself.

"I have a few guide lines though. Before we start the training I will preform an enema on you to thought clean you out. It's not as gross as you think it will be. If by chance you do get hurt I would of course be liable and will pay for whatever medical charges you have. Before we start I will go over everything I plan to do and you can object to anything you absolutely don't want to do. I promise you will be safe and well cared for while your stay here. I have a form for you to sign before you leave today. If you decide to follow through with the training I would like you to be here the same time next week so you have time to take off work and to think this over." Derek nodded along as he processed everything.

They talked about a few more details then Stiles had Derek sign a few forms. Derek went home shortly after and Stiles was left to wait out another week.


Making good to his word, Derek was knocking at Stiles' door six o'clock on Friday evening. He had nothing with him but his car keys and Stiles told him he could put them on the hook that was by the door.

Derek followed Stiles to the playroom and was shocked to see all of the toys he had stoked inside. Butt plugs with tails on the end, gags of all sorts, different leather bondage items; Derek was excited about what the week had in store for him.

Stiles explained to Derek that he would be using most of the items around the room so to look at them and tell him if he didn't want any used on him. Truthfully, Derek wanted to feel the influence of each and every toy in the room.

"You need to pick a safeword next. What shall it be?"

Derek thought before answering, "Bumble bee."

Stiles nodded before leading Derek to the bathroom. It was a huge, holding a bath, shower, a padded table, and a toilet. "Lay yourself over the table and grab onto the edges while I get you ready for the enema," Stiles commanded.

Stiles searched through a few cabinets before finding everything he needed. "Have you ever had an enema before Derek?"

The man only shook his head and looked around nervously. "It'll feel a bit odd at first but it's necessary. Tails are worn for long periods of time and I don't want you to get an infection. I take care of my pups."

Stiles lubed up a few of his fingers and started to work them into Derek. He instantly sprouted a large boner by the time Stiles was ready to put the tube in him. Derek moaned in discomfort and the long tube fed into his ass. "I'm starting to flow now, pup. Just hold into the sides of the table."

Derek did as he was told when he felt a sudden rush if water and jumped forward. "Shh shh pup. I've got you," Stiles whispered while running a hand up and down his back. The water flow abruptly stopped and Derek almost kneeled over with relief. "Hold it in for a second then I'll help you to the toilet." Derek nodded in agreement and just laid and waiting.

A few minutes latter the water had taken its effects and Derek was a whining mess from the cramps. Stiles helped him over to the toilet where he released immediately. "Good boy," Stiles praised while helping Derek off of the toilet.

Stiles led Derek back to the playroom and told him to kneel in the middle. He went to pick up a few items then brought them back to Derek. As Stiles put the supplies on Derek, he explained what they were and why he was using them.

"This is a collar. It's simple and just a black leather. It has a buckle to secure it in place and a matching leash." Stiles showed Derek the collar before slipping it on his neck.

"These are gloves. They both have a bar inside of them for you to curl your fingers around. They strap at the wrist with a buckle and you won't be able to get them off without help. They are simply to restrict any finger and hand movement." Stiles once again showed Derek the gloves before securing them on as well.

"This is a leather strap that folds your legs together. It will force you to only be able to crawl and you have to find your own balance." Stiles strapped the leather around Derek's ankles and forelegs.

"This is a cock ring. It will restrict any and all orgasm." Stiles tightened the ring around Derek's hard cock before picking up the last object. "This will be your tail. It's a rubber shaped tail that is attached to a small butt plug. Each day I'll change the plug to a new and bigger one. You have to inform me if you need to go to the bathroom so I can remove it." Stiles slowly inserted to plug into Derek's already loose ass.

"I have a gag I will latter be using but for now I want to know if something feels wrong. Other than that you are to remain silent unless I ask you a direct question or you need to go to the bathroom. You will from now on call Master and respect that I am above you. If you understand pup, nod your head."

Derek nodded and Stiles picked up his leash. "Try to keep up," he said as he started to walk. It took Derek a minute to get used to how his legs were tied but after a while he has in stride with Stiles. They walked a few laps around the playroom before Stiles abruptly stopped. Derek almost ran into the back of his knees but was lucky, and didn't. "Good boy," Stiles said as he bent over and pet the top of Derek's head.

"Why don't I get you some dinner then I can show you where you'll be sleeping. Tomorrow will be a long day so I want you to got lots of rest tonight." Derek nodded excitedly at the proposition and Stiles told him to stay while he got Derek his food.

Stiles came back a few minutes later with chopped up lasagna in a dog bowl. In the other hand he had another dog bowl filled with water. Stiles sat the two bowls on a mat in the middle of the floor and unhooked Derek's leash before telling him he could eat.

At first it was weird for Derek to have to smash his whole face in the bowl just to get to the food, but he didn't care after a while. He lapped up the water after finishing the lasagna. He then sat back on his heals quietly, waiting for further instruction.

"Let's clean your face up before you go to bed. Follow," Stiles simply commanded and turned for the bathroom. He wiped Derek's face down with a wet rag before leading him back into the room.

"You will be sleeping in this kennel at night," Stiles pointed to the steel cage in the corner. "If anything happens and you need help I will be able to hear you if you yell. There it a dog bed laid out on the floor of it already so it should keep you warm." Stiles walked a few paces forward, opened the cage door and said, "Hurry up pet! Get in."

Derek slowly crawled in and curled in a small ball that the cage would allow as Stiles closed and locked the door. "Goodnight pup," he said as he turned out the lights and left the room. Derek was left to his own thoughts about what the next day had in store for him.

Chapter Text

Derek woke up early the next morning to the sound of his cage rattling and the smell of oatmeal. "Rise and shine pup!" Stiles said happily. Derek, not being a morning person, had to stretch his sore muscles before even thinking of moving. He slowly crawled over to his oatmeal and began to slurp it down. He drank the water that was set out too, then looked up expectingly at Stiles.

"I need to go to the bathroom, Master," Derek said in a small voice.

"Ok," Stiles replied and clipped the leash to Derek's collar, then lead him out of the playroom. Derek was confused why they weren't just going to use the bathroom in there until they came to a back door. "Dogs go to the bathroom outside." Stiles slowly pulled out the butt plug then sat it on a table. She then opened the back door and lead Derek out.

"Go pup," he said once they were standing in the middle of the back yard. Thank god he has a thick fence, thought Derek. He peed quickly then awkwardly squatted to poop. His face was warm and red when Stiles wiped his butt at the backdoor with a strip of toilet paper.

Stiles led him back to the playroom. Once back inside and they were soon making laps around the room again. Stiles then stopped in the middle of the room and told Derek to stay as he went and grabbed a few more supplies. He came back with a new tail, a gag, and nipple clamps.

"Today's going to be a step up from yesterday. Instead of a safeword you will have a safe signal. If you punch the ground with your hand I will stop what I'm doing and take everything off of you. Nod if you understand." Derek nodded and Stiles went ahead, "Now I'm just going to put your tail in."

Stiles did it quickly then talked a little about the gag. "It's just a simple ball gag that fits in your mouth. You can still breath and make sounds around it if you need. Open up." Derek opened up and Stiles slipped the gag into his mouth. "Now I'm putting on the nipple clamps. You'll feel a pinch but nothing to bad." Derek sucked in a breath and Stiles pinched the clamps over his nipples. "They vibrate along with that butt plug in your ass, pup," Stiles said with a wink.

"Now we will work on obedience. Just listen to what I say pup and you'll be fine. Now sit." Derek sat. "Lay down." Derek slowly rolled all the way onto the ground. "Good boy. Back up." He listened and was on his knees before Stiles could reprimand him. "Follow me. Pay attention and don't run into me knees."

Derek let Stiles lead him around and stopped behind him when he came to an abrupt haunt. "Good boy," Stiles would praise as he pet behind Derek's ears.

"The next exercise should be pretty easy. All I want you to do is follow commands. Sit," Stiles said in a stern voice.

Derek awkwardly sat with the tail and Stiles praised him for it.

"Now, lay down." Derek complied once again.

The exercise went on for a while longer and when they were done Stiles gave Derek a new bowl of water. Stiles had Derek walking behind him again when the vibrator and the clamps turned on.

"Nnghh," Derek uncomprehendingly said from behind the gag.

"Keep up," Stiles snapped and Derek tried.

The vibrations stopped and continued at random times. Derek couldn't expect anything. Once Stiles was satisfied he gave Derek more water and pulled out another chain with a single clamp attached to the end.

Stiles was silent as he attached the chain to the one already hooked up and pinched the head of Derek's cock. Derek was confused by what was happening and wined when he felt the harsh metal clamp his tip. It stung like a bitch and he glared at Stiles.

"I know, pup," was all Stiles said.

Stiles led Derek to the living room and sat on the couch. Derek tried to follow him up but Stiles pulled on the chains. "Dogs stay on the floor," Stiles said as Derek cried out.

Stiles proceeded to watch a movie, Derek thinks it's "Rise of the Empire", but he's not sure. Derek stays on his knees for half of the movie then he decides to lay down. But laying straight down on his chest would hurt his nipples further. Stiles' legs were slightly spread apart and one in front of the other. Derek lay behind the first leg and rested his head atop the other foot. He sighed and curled his gloved hands by his face.

Stiles peaked at him and snorted through his nose in amusement. He then leaned back and continued to watch the movie. Derek is a cute pup, he thought.

The movie finished and Stiles led Derek to the kitchen. Tonight he made tomato soup. He poured some in a bowl for himself and some in Derek's dog bowl. Derek slurped it up, more going up his nose than down his throat. Stiles cleaned him up again then lead Derek to the bathroom. Derek whined in fear of having another enema or whatever they were called. It wasn't too fun the first time.

"Oh, pup. Just a bath. Promise," Stiles grinned.

Derek nodded and they enter the bathroom. Stiles took the gloves, clamps/ chains, and the leather leg straps. He left the collar, butt plug (tail), and cock ring intact.

Derek kneeled in the tub and Stiles ran water over his sweat stricken body. Stiles soaped up a loofa and scrubbed Derek's body. He shampooed Derek's hair, then rinsed everything off.

"That's a good boy," Stiles muttered as Derek stepped out and dried him off with a bushy towel.

Stiles put Derek's accessories back on and led him to his cage. "Goodnight, Derek. Maybe if you're a good boy tomorrow I'll let you sleep on the end of my bed."

Derek barked in agreement and curled up in the cage, settling in for the night.

Chapter Text

The next morning Stiles came and let Derek out of his cage. He then left to make breakfast. Derek really had to pee and did not enjoy doing his business outside yesterday. He slowly stood on his feet and went to the bathroom. After he was done he flushed the toilet with some difficulty because of the gloves.

He walked back into the playroom and was met with the sight of an angry Stiles, food bowl still in his hand. "What were you doing, Derek?" he asked through grinded teeth.

Derek just looked down and dropped to his knees. "I'm sorry, Master."

"Don't talk right now. Not only did you stand without permission you also used the toilet when just yesterday I told you that dogs went to the bathroom outside! I'm disappointed, pup. You were doing so well." Stiles put the food bowl down and muttered, "Eat your food then wait in your cage. I'll be back." He then left.

Derek ate his food and kneeled in his kennel. Tears streamed down his face when he thought of how disappointed Stiles had looked. He just really had to go, though.


Stiles came back ten minutes later with a crop in his hands. "I know that we haven't talked about punishment yet, pet, but I think it's time that we do. Yesterday I told you that dogs went to the bathroom outside. This morning you disobeyed that. I know that I didn't specify it was a rule, so I'll go easy on you. This time. Only five lashes. Can you do that for me, pet?"

Derek nodded from within his cage and murmured his agreements. "Of course, Master. I would take more if it was asked, Master."

"Don't push me, pup," Stiles warned. "Out of the cage," he demanded.

Derek crawled over to Stiles on his knees and dropped his forehead to the floor. He was sorry. He really was.

Stiles walked off to the side and drug a small futon to the middle of the room near Derek. "Go ahead and lean over this, pup. Remember, if you need to, just safeword and I will stop. Do you remember your safeword, pet?"

"Bumble bee," Derek mumbled and did as he was told, then waited. He flinched as he heard the crop whistling and yelped when it made contact to his bare bottom. The strip it left burned and Derek twisted to his right. Stiles guided his chest back to the futon and laid another strip on Derek's ass. In quick secession two more were burned into Derek's hide. That's how it felt anyway.

"One more, pet. Can you take one more?"

Derek wordlessly nodded, only wanted to get this forsaken punishment over. And Stiles had said that he would go easy. Derek reminded himself to never get in trouble again.

Stiles must have really put his weight into the last hit. It made Derek jump off of the small futon and curl up on the cold floor. Bloody hell. That one hurt.

Stiles picked Derek up and set him on the four poster bed. Derek couldn't see anything through the thick veil of tears. Then he felt something warm on his butt. Ointment. Thank God.

It was only after Derek's crying slowed when he hear Stiles muttering two words to him. "You're forgiven. You're forgiven." Then Derek noticed that he was bawling, "I'm sorry. So sorry, Master."

Stiles looked Derek in the eye and smiled. "It's all okay now. Everything is forgiven and soon to be forgotten. Promise."

Derek nodded and relaxed against Stiles. He took a deep breath and tried to put the situation behind him. It was just like Stiles had said. It was over.


Stiles served Derek lunch and by then he was feeling much better. He used the backyard and Stiles complimented him the whole time. They practiced crawling at heel and Stiles was also pleased with him then.

"Time to start something new, pup. This is a vibrator," Stiles held up a shiny black bullet shaped object. "And this is a cock ring," Stiles held up another object, this one was a black, round ring.

Stiles kneeled down by Derek and stroked his soft member. Derek's eyes grew. He knew that he should expect this, but it was new to him. The whole sex thing. Derek had never really been able to hold a steady relationship. Or anything that resembled any kind of mutual friendships.

Derek gasped at the feel of someone else's hand on his hardening cock. It felt amazing. Better than he ever could have imagined. Then Stiles slipped on the 'ring' thing and left Derek to ache for a moment before returning.

"Flip over, pup. This should feel good. Don't worry."

Derek flipped over and he heard the pop of a bottle then warm fingers massaging his lower back and ass. The slick fingers ran over and then into Derek's crack, across his virgin hole. The sensation was new but not totally unwelcome. It actually felt kind of good. Electric.

Stiles ran only one finger between Derek's cheeks this time and put more pressure on his sensitive hole than before. The tip of his finger popped in and Derek jumped in surprise, accidentally pulling the finger back out.

Stiles rubbed his slick hand up Derek's back few times while whispering, "It's okay. Just relax for me, pup. You're doing great."

Derek took a deep breath and tried his best to relax. Stiles started repeating his earlier actions, dragging his wet finger over Derek's hole. This time, when he pushed the tip in, Derek didn't jump but he did tense up.

"Doing so good, puppy. You're being amazing for me. So good," Stiles praised and Derek relaxed. He trusted Stiles. Trusted him with this.

Stiles got half of his finger in before he pulled it out then pushed it back in. He was finger fucking Derek even if it was at a slow pace. Derek had seen too many pornos to not recognize this part. And he knew what was next.

Once Stiles could fit his whole finger in Derek, he added another. That hurt.

Derek grunted through the burn and Stiles reassured him that after the first time, it wouldn't feel this bad. But after awhile the pain bled to pleasure and Derek was pushing back against Stiles.

"That's it, pup. Now it feels good, doesn't it?"

"Mhhg," Derek moaned in response. It definitely felt better. A lot better.

Derek's cloudy mind didn't notice the switch from Stiles' fingers to the vibrator, but when it started to do its job, Derek was in heaven. And just when that pleasure was coming to a peak, it was stopped by the damned little right around his cock.

Derek looked back at Stiles, confused and quite frankly, a little hurt. Stiles only smiled. "That, my dear, is called edging. Fun, isn't it."

Derek shook his head 'no' and the vibrations stopped. "Take a minute to get everything under control and we will try again.

Derek's hardness never quelled though, and by the time Stiles turned the vibrator back on, he was so hurtfully aching in his confinements already.

This went on for three more times and then Stiles permitted Derek to have the most mind blowing orgasm of his life. He blacked out and when he woke again he found a hot bowl of food by the dog bed that he lay in. It was a nice day after the initial infraction. But just like Stiles had said, that was behind them and forgotten.