He really should've fucking obeyed, should've just listened. But that would ruin the fun.

The shackles rattled as Stiles shifted to make himself more comfortable on Derek's lap. The cuffs on his wrist were almost too tight and he was sure to have bruises later on. He secretly loved when Derek left bruises on him, especially when he pressed on them later on. They weren't anything a sweater couldn't hide for a few days. His balance on Derek's lap slipped and almost fell backwards but Derek caught him

"Stop moving Stiles" Derek demanded.

"You fucking love this don't you?"

Whap.

Stiles yelped and hung his head over Derek's shoulder, grinding into Derek's thigh again.

"Derek…fuck"

Whap. Stiles hissed between clenched teeth.

"Sir…"

"That's better" Derek purred

When Stiles felt a warm hand massage his tender ass he jumped a bit, he was so sore that the slightest touch sent shockwaves of feeling up his spine. His eyes widened and he pushed up into Derek's lap to move away when he felt a wet slick feeling push at his hole. He flinched as soon as the words left his mouth.

"No Derek don't-."

Wahp.

"Fuck!" Stiles grinded into Derek's lap again, his throbbing erection straining against the front of the tight red and black briefs Derek made him wear. The back of the briefs were pulled down exposing his bare ass but the front was still pulled up against his straining erection that was leaking insane amounts of precum.

Both of his wrists were cuffed with a linked chain dangling between them. Derek had him sitting atop his lap cowboy style, both of them facing each other.

"Are you telling me what to do?"

"No…I jus-."

Wahp.

"Fucking shit...I'm gonna come if you do that again, I can't hold it anymore D-Sir…" Stiles said exhaling a shivery breath.

Derek rubbed his ass again with both hands this time pulling his cheeks slightly apart as he pushed a finger in. Stiles groaned and pushed back into the finger.

"You don't come until I say so, if you do I'll leave these cuff on you for the rest of the night", Derek's words caused Stiles to buck into him again.

"You like that?"

"Shit…I'm gonna…"

"Stiles don't"

Stiles took a deep breath and nodded. His legs were shaking and his body was flushing pink in random areas, his cheeks were pink as well. He and Derek had been going at it for about an hour now, they were both slick with sweat and he was exhausted. Derek had kept him on edge for the last thirty minutes and it would be stupid to ruin it now. But seriously? He was going to come at any moment. The fact that he was a bit of a masochist, ok, very much of a masochist, didn't help much either.

Every time Derek spanked him it sent him that much closer to the edge. His heavy breathing and thinking was interrupted by Derek's rough voice.

"Just ask me", Stiles looked up and over at Derek.

"Hunh?"

"Stiles…I know what you want; but you need to ask", Stiles rolled his eyes.

"You just want me to talk dirty…Sir" Stiles said smugly.

"Either I spank you again or you ask", Stiles literally whimpered when he felt Derek's hand pat lightly against his ass. It was so tender, he gave in.

"Put your dick in me" he grumbled into the crook of Derek's neck

"Wow…Stiles, I know you can do better than that" Derek said lifting Stiles' leg and spreading it so that he was straddling over both of his legs.

"Sir, please…put your dick in me" he moaned and rubbing his erection against Derek's stomach.

"Fuck…you're getting there…" Derek growled rutting his hard length between the cleft of Stiles' cheeks. Stiles' groaned in frustration and grabbed each side of Derek's face looking into his eyes.

"I want you to fuck me until I forget my name and come all over my face while I -."

That was all Derek needed, he hoisted Stiles up and pushed in entire length in with one long jab, he growled at the feeling of Stiles' walls loosening and then clenching tightly around him. He knew Stiles wasn't going to last long, but little did Stiles know, he wouldn't either. He had also been edging himself; Stiles had been facing away the entire time so he had no clue.

"Fuck, Derek…I'm-so fucking full." Stiles moaned, his voice hiccupping with how hard Derek was stabbing into him.

"Full of what?" Derek growled

"Full of your dick…full of you" Stiles choked out when Derek jammed into his prostate "Derek, I'm about to come right now, right fucking now! Please say I can, please…oh fuck!"

Stiles came inside his briefs, his entire body shaking and trembling, he trapped Derek's head in between his arms and the cuffs and pulled him closer as his orgasm forced itself from him. Unexpectedly he felt Derek's spasms inside of him and another filling sensation.

"Fuck Stiles!" Derek growled as his own orgasm tore through him and deep into Stiles. Stiles went limp against his chest, panting heavily. He chuckled and caressed his hand over the boys buzzed hair. Stiles stirred under him.

"That felt so good it hurt..." he said, his voice raw and raspy into Derek's throat

"You like when it hurts"

"Yeah but my fucking dick is aching"

Derek smiled and reached between them and jerked Stiles dick. Causing him to hiss and stumble backwards off Derek's lap. Derek caught him before he could hit the floor and pulled him back up laughing.

"Derek that not funny! It's sore…my ass too!"

"Be careful speaking like that, I can go another round." Derek warned.

Stiles whined sarcastically, "Oh no, please sir, don't fuck me into submission"

Derek rolled his eyes.

"Can you take these off now?" Stiles asked shoving his wrist at Derek. Derek shook his head. "No"

"What? Why?" Stiles asked, a small frown working its way onto his face

"You came without my permission." Derek said bluntly, Stiles gaped and exhaled

"Derek, you can't be serious", Derek frowned and cocked his head

"I'm very serious Stiles, oh and you're wearing those for the rest of the day" he said pointing to the soiled briefs.

"Derek please! Come on...I'll suck your dick again if you let me out" Stiles bargained, poking his lip out and giving Derek 'the eyes'.

Derek raised both brows in shock.

"Really?"