Drawn by the marvelous, Castiel-0! :3

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I feel ridiculous. Sam thought as he pulled on the gloves that matched his dress.

The dress barely reached his knees and his chest was exposed so much, that he thought if he actually had boobs, they would pop out of it.

And then, there was what Cas had made him wear underneath.

A pair of silk, red, panties.

Sam sighed and hung his head. If I trip... My ass is gonna be exposed... Dean will see what's underneath. Then I'll have to kill myself. Death is better than dealing with Dean's jokes.

He sighed again and put on the red shoes- correction, red heels, before he walked out his room.

"SAMMY!! COME ON MAN!! WE GOTTA GO!! CHARLIE'S GONNA BE PISSED IF WE'RE LATE!!"

Sam groaned quietly as he met his brother and boyfriend in the living room. He stumbled a bit and glared down at the heels. "How can women walk- HEY!!"

Cas and Dean smiled innocently at Sam, who was glaring at them.

"Why aren't you two dressed?!"

Dean fake pouted at his little brother. "Our dresses couldn't fit, Sammy." He started laughing after he gave his brother a once over.

Sam was about to yell at Dean, but the flash of a camera startled him. He looked over at Cas and his jaw dropped when he saw the camera. "Did you just-"

"Yes, I did, Sam." Cas smiled and looked at the picture.

"Delete it."

Cas looked up and gave Sam puppy dog eyes. "Please let me keep it."

Sam huffed and turned away. "Whatever... I'm going change."

"No, Sammy! We gotta go!" Dean grabbed Sam's arm and pulled him out the bunker, Cas following behind like an innocent puppy.

Well, not innocent, seeing as he was staring at Sam's ass, trying to get a peek under the dress.

The three got into the impala and drove to Charlie's house, Sam grumbling about the situation the whole time.

They got out the impala and went up to Charlie's front door. Dean knocked and an already tipsy Charlie opened the door.

"Hey guys! WAH! SAM YOU LOOK BEAUTIFUL!!"

Sam blushed deeply. "Thanks Charlie..."

Charlie smiled and ushered them all in. "Alcohol is in the kitchen!" She sang before whispering to Cas, "And there's a special room upstairs just for you and Sam." She winked, then disappeared into the sea of people dressed as different characters.

Cas just smirked at the thought. He knew they would use the room, but just had to wait for the right time.

About half an hour later, Sam was still on his first cup of alcohol. He was currently be flirted with by some guy and he was actually enjoying it.

Cas wasn't. He really wasn't.

He watched as Sam walked away from the guy and started walking to the kitchen.

He also watched as one of Sam's heels broke and he fell, the dressing flying up, revealing his red panties.

He wore them! He wore the panties! Cas thought with a small smirk as he took in the scene.

There were quiet gasps as everything got quiet and the attention shifted to Sam.

Dean and Charlie pushed through the people and stopped when they saw Sam.

Charlie held out her hand to Dean, her eyes never leaving Sam.

Dean pulled a 100 dollar bill out his wallet and placed it in Charlie's hand. He then started to quietly laugh at his brother, then he started gagging, then he threw up on the floor, then he laughed again.

Sam's face was as red as his dress. He felt the eyes of everyone on his ass and his blush got deeper, if that was possible.

He suddenly felt his ass being covered with the dress, then felt a hand wrap around his bicep. He was suddenly being lifted up from the floor. He turned his head and saw Cas.

Cas gave him a small smile, then looked down at Sam's shoes.

Sam looked down as well, then took them both off.

Cas pulled Sam away from everyone who had started to disperse. He pulled the still blushing boy upstairs to the room that Charlie mentioned.

Sam walked into the room and threw the shoes on the floor. He sat down on the bed and immediately put his head in his hands.

Cas quietly closed the door and locked it. He went over to Sam and sat next to him. "Sam, it'll be alright."

"Cas, everyone saw! They'll never forget! It'll be like high school all over again... I'm nothing but the freak kid..."

"Sam, don't say that. You're not a freak." Cas kissed his cheek and wrapped his arm around him. "I know what can cheer you up."

"What?" Sam asked pitifully as he raised his head.

Cas just smiled and let him go. He stood and was gone and back in a matter of seconds. He had something behind his back.

"Cas, what is it?"

"I brought your favorite toy."

Sam's heart stopped for a second as he watched Cas pull the vibrator out from behind his back. "Y-You brought it with you?"

"Mhm. I wanted to surprise you. Now, stand up and bend over for daddy."

Sam stood up and turned to where he was facing the bed. He bent over and felt his dress start riding up.

Cas pushed Sam's dress higher and bit his lip at the sight. He took out his phone and snapped a picture of Sam bent over in his undies. He put his phone away and slowly pulled down the panties.

Sam wiggled and shivered a bit a the coldness in the room. His cock throbbed at the thought of Cas pushing the toy inside of him.

Cas smiled onceand went over to the nightstand. He opened it and picked up a tube of lube. He looked closer in the drawer and saw a not that said:

Don't hurt him too much, Cas. ;)
~Charlie

He quietly chuckled before closing the drawer and going back over to Sam. He lubed up Sam's hole, then the toy, then slowly pushed it into him.

Sam let out a quiet gasp once he felt it. He gripped the sheets in his fists and his lips parted in a silent scream.

Cas pushed it all the way in, making sure to press it against Sam's prostate. "You good, Sammy?"

"Y-Yeah... Turn it on... Please."

Cas flipped the switch at the base of the toy and Sam howled with pleasure.

Sam used one hand a started to stroke his cock, already feeling as if he was gonna cum.

"Why not come put the pretty little mouth to use, baby?"

Sam looked up and saw Cas standing at the foot of the bed with his pants unzipped and cock out. Sam crawled on to the bed and went over to him on all fours.

Using only his mouth, he started to lick around the head of his cock. He took all of Cas in his mouth in one swift motion.

Cas moaned and started to pet Sam's hair. "Good boy." He threw his head back and moaned again.

Not long after, Sam started to tremble. He started to stroke his cock faster and harder, then worked his mouth around Cas' cock faster.

"Sam... You're close... Cum, Sammy."

Sam pulled away from Cas and cried out as he came on to his hand and the sheets below him.

At the sight of Sam coming, Cas came on Sam's face with his own growl.

They both stayed how they were for a moment until Cas remembered the toy. He turned it off and gently pulled it out of Sam, who whimpered lightly.

Cas picked up a tissue from the nightstand and cleaned off Sam's face. He then snapped his fingers and they were both fully dressed again and the bed was clean. He gently kissed Sam on the lips. "Do you feel better?" He asked as he pulled away.

"Yes... Thank you Cas."

"You are welcome, Sam."

"I got a question though." Sam said as he moved from his position and sat on the bed.

Cas sat next to him. "What is it?"

"Why did you have the toy in the first place?"

"Well, I planned to tease you with it during the party. And then not let you cum."

"Oh you kinky son of a bitch."

"But, you love me."

"Yeah... Yeah. I love you."