Side Bets

Rising Panic

"Stiles. Look at me." Derek looked at Stiles with a serious face. "Listen to me." The boy nervously met his eyes and nodded, indicating he was listening and Derek's scary thinking expression softened to something a little kinder, more understanding.

"You can relax, okay? I'm not going to hurt you or touch you anywhere without telling you first. If you really need to put it on by yourself I'll let you but I want to make sure it's on correctly and comfortably before you go practice for an hour. Speaking of," Derek checked his watch, missing how Stiles's eyes widened, surprised at Derek's considerate words. "We have about 13 minutes left so make up your mind. We still have to get your gear on too."

Stiles's face visibly relaxed at his words, no longer worried about Derek touching him without his say so. It took him a second to think over his options before relaxing his body.

"Okay... y-you can do it for me..." Albeit still nervous, he gave Derek permission with a mumble.

"What was that?" Derek asked, a smile forming on his face and Stiles rolled his eyes.

"Oh shut up! We both know you heard me just fine with your stupid werewolf ears! You're just trying to embarrass me now!" Derek's smile turned to a wolfish grin.

"You're right, I am" He laughed, gingerly moving Stiles's foot from his chest back to resting slightly bent on the seat so Derek was able to stand between his thighs.

Stiles did his best to ignore how his heart swelled seeing such a rare sight. He'd wear a diaper everyday if it meant he got to see sourwolf smile and laugh like that again. Well... actually he's not sure about that, he hasn't even worn one once yet so maybe he's being a bit hasty with this sudden diaper loyalty.

"Alright, trying again... can I take your pants and boxers off?" Derek looked at Stiles patiently waiting for permission while curling his fingers around the edge of his jeans.

"Yes..." Stiles wanted to squeeze his thighs together out of nerves but Derek's own body prevented that. So instead he chewed on his nail as he shucked his shoes off without untying them and Derek started to remove his pants and underwear.

"You shouldn't chew your nails, it's not good for your teeth." Derek commented and he quickly pulled everything off his legs.

"What are you, my dentist?" Stiles said sarcastically, drawing his knees back up to hide himself again. 

Derek rolled his eyes, Stiles is lucky he didn't give him that teether he also impulsively bought, but they were quickly running out of time so he didn't bother for now. Instead he unfolded the diaper and put his hand under Stiles's knees.

"I'm going to lift up your butt so I can put the diaper under you. Sound good?" He asked looking up at Stiles who was watching, unintentionally almost hiding behind the hand he was chewing on.

"Yeah... 's fine..." Stiles responded quietly, while he was still nervous about being so exposed he was starting to relax now that Derek was explaining things before hand.

It's not so scary when I know what's going on... he thought to himself, letting Derek manhandle his body so he could slip the fluffy diaper underneath him.

It was cushy under his butt which he didn't mind but the crinkly noises seemed way too loud and noticeable, although Derek tried to assured him no one would hear it over Coach's constant yelling and whistle blowing.

Grabbing the powder, Derek continued to explain what he was going to do before he did it. However, Stiles accidentally started to tuned out most of his explanation about why the powder was needed when Derek's warm hands started gently— shockingly gently— rubbing the baby powder in.