A Destiel Mafia Au

Regret

Dean's mood dimmed, but he kept a hollow smile, "whatever you say boss." He tried to stand but was hindered by his restraints. Was this his life now? Why did he ever thought this was a good idea?

Castiel then held up his finger as if pointing to the ceiling as two men gripped onto Deans arms to yank him to his feet and keep a gun behind his head. As Dean began to be walk out Castiel smirked, "Oh and I forgot to mention— A friend of yours stopped by today... And let's just say she didn't like her welcoming gift..." Castiel chuckled as Dean was dragged away.

Dean chewed his lip to stop himself from screaming obscenities at Castiel. Lisa was a good person and a dear friend. How dare he? Dean felt tears run down his face. Why was he doing this to him? Dean made up his mind to do whatever he could to make this man kill him.

The men pushed the man into the empty cell that Dean had been inside the night before. They untied him and threw him clothes to then slam the door shut, "Knock when you're dressed!" Balthazar growled. What they have given Dean was a looser black lace male thong, thigh high thin black stockings, a white ruffled 'Japanese' maid apron, a cute small collar with a gold bell and white ruffles, and finally two black wrist—and ankle—cuffs with white ruffles on the sides like the collar with a metal butt plug to add to the outfit.

Dean flushed when he saw the butt plug. Was he supposed to... put it in? He was too scared to ask so he just put the rest of the outfit on. He was still shivering when he had all the parts on. What was he supposed to do now? He tapped lightly on the door.

Balthazar heard a faint knock and opened the door to see Dean. The two men smirked and chuckled a little, "Boss sure likes men in little girls clothing huh?" They then gripped Deans arms and lead him back to the 'throne-room'.

Castiel waited and waited. Peering up to see Dean in the outfit holding something— his butt plug? Castiel narrowed his eyes as they let Dean go to keep at gunpoint as one went to guard the door and the other to stand beside Castiel. He smirked and stood up to take the plug out of the pale man's hands and twisted it between his fingers, "You don't like it?"

Dean smirked uneasily, "I didn't know what you wanted me to do with it, 'Master,'" he said obediently. He had to obey, right? Let him obey until it drives his captor crazy.

Castiel chuckled and sat down, "Be d over my lap," he patted his thighs encouragingly, "Let me show you what to do with it..." Castiel kept his gaze on Dean.

Dean shivered. He had hoped Castiel would let it slide but- he walked over to Castiel shakily, stomach running in somersaults, "D-Do we really have to do this?" He couldn't maintain his smile as he bent over Castiel's lap.

Castiel chuckled and playfully smacked Deans ass lightly, "Of course~". Castiel then carefully lifted the man's dress/skirt and slowly pulled down his thongs. He took the plug and placed it against Deans lips, "Why don't you wet it before it enters your virgin ass~" Castiel smirked.

Dean felt involuntary tears run down his face as he opened his mouth and put his saliva onto the plug. This man was mad. Why did he ever think this was a good idea? What was he now? This man's sex slave? His toy? He gritted his teeth after Castiel took out the toy. Closing his eyes shut.

Castiel glanced at the plug once it was lathered in saliva and grinned. He then spread the man's cheeks and placed the rounded point in the surface of the man's anus. He slowly began to push until it 'popped' inside all the way in. He licked his lips and playfully smacked the man's asscheek again before pulling the man's thongs up and patted his back, "Stand up. You see? It wasn't so bad~"

Dean flushed dark when he felt something push into his hole, he sobbed biting his lip to keep it in as Castiel pushed the plug all the way inside. Dean tried to stand but felt the strange object move inside him, he groaned, keeling over and falling to his knees. It felt so strange, so foreign. He flushed dark, trying to stand through the strange sensation. He looked away from Castiel, seething.

Castiel gently patted Deans head, "Take your time, I realize it is the first having anything in there..." he then looked at his men as if nothing had happened. He glared at Bartholomew as his face was flushed from witnessing the very moment, "Is something wrong?" Bartholomew swallowed hard and shook his head as he stood back up straight and focused on his duty, "N-no sir..."

Dean flushed dark. He had been... soiled in front of a crowd. He closed his eyes, trying to will the panic, the fear, the embarrassment away. It had been his first... time with anything going in there... he hugged himself as he tried to stand, gasping and panting as he felt the plug moving inside. He bit his lip.