Stiles' idea of a place for dinner turned out to be a drive-through where they got burgers and fries. However, Derek became suspicious when Stiles drove them out into a remote area to eat.

Stiles parked the car but instead of reaching for the bags of food in Derek's lap he reached for his fly.

"I'm going to eat and you're going to put your mouth to good use."

"Seriously?" Derek rolled his eyes.

"And if I finish before I finish you will regret it." His voice dropped which send shivers down Derek's spine. He put the bags with his own food in the foot room and handed Stiles his dinner who immediately started to peel the burger out of its wrapper.

Bending over did things to the plug still inside him but Derek didn't let that distract him. He didn't have much time.

He knew how Stiles liked his blowjobs and he used every trick he knew. With one hand Derek was gently rolling his balls and with the other he was pumping at the base of the shaft while he tried to take him deep. Derek had never mastered deep-throating but he took Stiles deep enough to hit the back of his throat and when he came back up, he sealed his lips around the shaft and sucked.

"You're not wasting time, are you?" Stiles tried to sound unaffected but he didn't fool anybody. Derek didn't answer and focused on the head instead. He suckled and licked, dipping his tongue in the slit, before he went back to bobbing up and down the shaft.

Stiles didn't last long and Derek grinned around the pulsing shaft when Stiles' release hit the back of his throat. He coughed with come and saliva dripping down his chin but it was worth it.

When Derek finally looked up he found Stiles with his head resting on the back of the seat and his eyes closed. The wrapper from the burger lay balled up on the dashboard but there were some fries left.

"Close one," Stiles said once he could speak again. "Congrats, you're actually going to come tonight."

"Thank you." Derek sat back up but had to shift a little until he found a position that didn't press the plug into uncomfortable places.

"You can eat now." Stiles put the last fries in his mouth and settled back in his seat.

Since they were already in a remote area they used the chance to walk Jack again. Meaning Derek had to walk Jack while Stiles stayed in the car and played with the cat. By now Derek seriously wondered whose cat it really was.

Eventually, they got a motel room and by now Derek was more than ready to get the plug out. His rim felt raw, same for his prostate and the constant arousal was driving him crazy. He just wanted to rip the cage off and get his hand on his dick. But he doubted that that would happen any time soon.

Stiles had locked the pets in the bathroom but now he turned to Derek. Finally.

"Get naked but leave the diaper on," he ordered and then he just watched while Derek shed one piece of clothing after the other until he stood there in his diaper. His cheeks burned, this was worse than being naked.

"Have you been a good boy?" Stiles asked and came closer. "Or did you wet yourself?"

"I was good." Derek had no idea where this was going but he played along.

"We'll see." Stiles opened the diaper and let the front flap down. "Hmm." He ran his fingertips over the wet spot and raised them for Derek to see. "How would you call this?"

"It's wet."

"So you did wet yourself."

"Yes." Derek swallowed thickly. This shouldn't be so hot. He felt his cock twitch in the cage and a fat drop of pre-come oozed out of the slit. "I'm sorry."

"You wet yourself like a little boy." Stiles smeared the thick liquid over the tip of the cage with his thumb. "Do you think you deserve to come like a big boy?"

"No." His voice sounded hoarse in his own ears. Now he did have an idea where this was going but coming like that wouldn't be easy. If he could come like that at all. His prostate already felt swollen and sore.

"We'll keep your useless dicklet locked up, that's for big boy orgasms." Stiles let go of his dick and reached farther down between his legs until he could grab the base of the plug. "You're going to come from this, like a good little boy, won't you?"

"Yes," Derek said, trembling when Stiles started to tap the base of the plug. "Please make me come like that."

"Like a good little boy?" Stiles prompted.

"Please." Derek licked his lips, this part never became easier but on the other hand, it let warmth spread deep in his belly every time Stiles made him say things like this. "Please make me come like a good little boy."

"On the bed, then." Stiles moved out of the way with an inviting gesture at the bed. "Face down, ass up."

Getting the plug out wasn't easy, his rim had closed around the base and after hours it had become dry and sore. Stiles added more lube and twisted and moved the plug a little before he even tried to pull it out. He went slow and Derek felt his hole open up around the bulb.

However, Stiles didn't just pull it out. Once the thickest part was breaching the rim, he pushed it back in.

Derek groaned and buried his face deeper in the pillow. He was already fisting the sheets but he knew that this was merely the beginning.

Stiles fucked him with the plug until it went in and out with barely any resistance at all.

"Nice and open, you should be able to take my fist now." Stiles decided and put the plug away.

"What?" Derek raised his head and tried to look at him over his shoulder but Stiles just swatted his ass to get him back in position.

"My fist isn't that much bigger than the plug," Stiles assured him. "Besides, I have the big plug here for later. I told you that I want to start to train you on that."

Derek remembered that and it had sounded hot but now that it was really happening to his ass and he wasn't so sure any longer.

"Just breathe," Stiles told him and reached for more lube. "I'll go slow. But you are going to come with my fist up there."

Derek wasn't so sure if he would even be able to take Stiles' whole hand but the thought alone filled him with want so he let out a deep breath and relaxed as good as he could.

Stiles rubbed soothing circles on his lower back while he pressed the fingers of his other hand in. Derek was loose enough to take them without a problem but then came the wide part with the tucked in thumb and that did get caught at the rim.

But Stiles was patient. He took his time, easing back and pushing forward, and when finally the widest part slipped past the rim, Derek cried in relief.

Sweat and tears burned in his eyes and dry sobs fell from his lips while his body just trembled in need. This was beyond the need to come. Distantly Derek was aware of his caged cock but his need had narrowed down to a place deeper in his body.

Stiles curled his fingers into a fist and for a second he just left it there to give Derek time to adjust the feeling

"How does it feel?" Stiles asked, his other hand still stroking his lower back.

"Full." Derek breathed out. "So full. Please, Stiles please." He didn't even know what he was begging for but then Stiles rubbed his knuckles over his prostate.

Derek howled.

He was writhing on Stiles' fist, frantically searching for something to hold on to and Stiles just rubbed his knuckles over his sweet spot.

Again and again without mercy.

Derek came.

His come dribbled out of his cock, his whole body shook with the intensity of his orgasm while Stiles kept firm pressure on his prostate, milking him even more.

And he didn't stop coming. Endless waves rippled through him, pleasure mixed with pain, and it wouldn't stop.

Derek wasn't sure when it ended but eventually, it did. His throat felt raw and he was crying but it was over. He couldn't uncramp his fingers just yet, and he might have ripped the sheets, and the rest of his body was just a trembling mess.

"Wow." Stiles stroke his back but his other hand was still in Derek. "That was intense."

Carefully Stiles eased his hand out but Derek still winced when it got caught on the rim. But then it was out and Derek just collapsed.

He smiled into the pillow but he was too tired for anything else.

Stiles cleaned him up and Derek was already drifting off to sleep when suddenly once again something nudged at his abused hole.

"Hmm?" He made but his body was too heavy to even lift his head.

"Just relax, you're doing good," Stiles said and then something big breached his rim. "You might be even loose enough to take it completely."

Derek wasn't conscious enough to really understand what Stiles was doing but he was content with just lying here at the brink of sleep and if Stiles wanted to do something down there Derek wouldn't stop him.

However, what was going up his ass was big.

At first, Stiles was just playing with the tip, testing the give, before he eased back. But with every push, he inched farther just a little bit and after a few minutes, Derek was there enough to realize what he was doing down there.

The biggest plug, the one that made a coke can look small, and Stiles was currently working it into his hole.

Derek doubted that outside of porn anybody was able to take a monster like this but Stiles seemed determined to find out.

"Tell me if it hurts." Stiles had noticed that Derek was back among the living and was now pushing with a little more force.

It did hurt, it was so big, there was no way it would fit without hurting him, but by now Derek wanted this. He felt the widest part just outside his rim and he wanted to feel it stretch his hole in an impossible way.

"Keep going." Derek keened but forced his body to stay relaxed and open.

It felt like an eternity, endless back and forth with next to no progress and Derek was close to calling it off, when Stiles gave the plug another push and it slipped in.

For a second Derek couldn't process what had just happened. But there was something big and hard in him and he felt his hole clench around the base of the plug. At least his muscles tried to clench, they managed some twitching but the plug held him open too much for more.

"Beautiful." Stiles spread his cheeks to have a better look at the base. "How does it feel?"

"Huge," Derek said after a moment. He still hadn't comprehended that the giant plug was now inside him. His whole lower region was sending signals of too much, too full and he felt like he would split open if he just breathed wrong.

"Can you turn around?"

"Dunno." He slurred the words. His body was still not really cooperating and every little move sent jolts of pain through his stretched insides.

Stiles helped him to roll over to his back and the new position changed the angle of the plug inside him. Derek whimpered, not sure what to do with the overload of sensation. So he just lay there with his arm over his eyes and waited for the world to make sense again. The plug felt amazing and Derek wanted it to last forever but at the same time, his mind was screaming to get it out. It was a mix he wasn't ready to deal with.

Suddenly Stiles' hand closed around his bare dick. Derek's eyes snapped open and he let out a strangled nose when Stiles licked over the head of his cock. Since the cage was gone it was filling rapidly and only seconds later Stiles was bobbing up and down his fully erect cock.

Derek came a second time with Stiles' mouth hot on him and the monster plug torturing his insides.

He might have blacked out a bit after that but when he came to, the plug was gone and he was lying cleaned up and warm under the blanket with Stiles. Derek snuggled closer and Stiles welcomed him with open arms.

"You did good, sleep now." Stiles kissed the top of his head.

With a content sigh, Derek drifted off to sleep.