"Welcome back, you good for nothing!"

Castiel watched Dean walk up to a prisoner with broad shoulders and hug him as he stayed a little back. They were in the hallway of the cafeteria and Dean's brother, Sam, had just ended his solitary confinement. "It's good to see you again, big brother" Sam replied, pulling back from the tight embrace. Despite being the younger brother, he was much taller than Dean. "What did I miss? What's new here?"

"Actually, who's new here... Sam this is Castiel. Castiel this is Sam"

"H-hi"

It took Sam a while to understand but once he had, he grinned and gave his brother a light nudge. Dean blushed, giggling, and his that astonished Castiel who had never seen him like that before. He seemed like... gone soft. All of a sudden, he was brought back to reality by Sam, standing right in front of him, with his hand out. Hesitantly, he extended his arm to shake his hand but the other inmate pulled him into a hug. "Nice to meet you, Castiel" Sam said as he quickly let go of him and fixed his hair. Well, he was definitely a hugger in addition to being handsome. The same eyes as Dean's. "Let's go find somewhere and sit down so we can talk, shall we?"

"How was the solitary confinement?"

"You know, you've been there yourself. Quiet. Boring. Never-Ending"

As the three of 'em found an empty table, Dean crossed in front of Castiel and pulled his chair out before he could just sit. The gesture took the prisoner by surprise and cause him clumsily sit down, not knowing how to behave, unlike the other two who took their seats without making such a fuss. "Cas, got here the day after you were sent to solitary. Bobby already had his eye on him" Dean explained, a touch of pride in his voice. Sam rolled his eyes in response and Castiel felt as he did when he had met his high school girlfriend's parents for the first time: embarrassed. He didn't like to be in the spotlight and was a bit uncomfortable, something Dean must have sensed since he stood up with a start. "Guess, we could use a bottle of red wine to loosen up and celebrate the return of my little brother. Just wait for me here"

"I-I don't think they will give you some wine, even if Sam had come back from confinement"

"Oh, but Dean gets a special treatment here since he-"

Dean promptly shoved his hand over his brother's mouth, interrupting him. "We don't want to give away all of our secrets yet, right Sammy?" Dean asked, kind of rhetorically. Sam shook his head and his brother removed his hand. Castiel was pretty confused. What were they talking about? Were they hiding something from him? A soft pat on his shoulder snapped him out of his thoughts. He looked up to see Dean sweetly smiling at him and forgot about the thing. "Sammy, I leave you on top of this"

"Got it, bro. I'll keep an eye on Castiel. No one is getting near him"

"Thanks"

Dean then headed for the kitchen counter and the other two inmates remained alone. Castiel was staring down at the table, ill at ease, as Sam observed him scrupulously. He was a nice guy, his brother had always had good taste in men. Still, there was something different in him. He was like the opposite of his exes. "You get on with Dean? Does he treat you right?" Sam inquired, trying to break the ice and make conversation. Castiel just nodded, almost afraid to reply. He had always been a shy person but now the cat had bitten his tongue. "Dean is a hothead sometimes, but he's a good brother. If he loves you, he's ready to die for you. I don't know whether he told you about our childhood but he has really stepped up to raise me since we were left alone"

"H-he did mention something. He... he can be very protective. He has saved my ass a few times"

"Bet he had also wrecked that ass of yours!"

Castiel turned red as a beet at that joke and Sam realized immediately how rude he had sounded. There was an awkward silence for what seemed like an eternity, not a pin dropped. Sam opened his mouth to apologize but the other prisoner went first. "W-we haven't had sex yet" Castiel uttered, not knowing exactly why he had spoken. Usually he didn't talk about these things but now he felt somehow obliged to clarify that his butt was still virgin. The look of incredulity upon Sam's face, though, bewildered him. "W-what?"

"You and Dean haven't fucked? Seriously?"

"Y-yes. We jerk off together... and sometimes he rubs against me but nothing more"

Sam looked really dumbfounded and that sort of bothered Castiel. Was it so hard to believe that nothing had happened between 'em? "Wow, I would have never expected it from my brother. You know, he generally does the deed before introducing himself. Sex is what has always carried on his past relationships. I imagine that- Oh, no. Speaking of exes..." Sam said, changing the subject as he glimpsed something he would have rather not see. Castiel followed the direction of his gaze and turned his head. There, several steps away, Dean was standing with a bottle of red wine in hand, talking with another prisoner. Just... It wasn't a regular person. It was Jack, the inmate working at the library. "That is... Dean's ex, Jack. A real sociopath. Better to stay away from him"

"A-a sociopath?"

"Yup. They only got along... under the sheets. Jeez, you could hear 'em throughout the facility-"

Sam kept talking but Castiel wasn't paying attention to him anymore. He watched the other two prisoners chatting and gradually connected the dots. Was that the reason why Dean had made him quit his job in the library? Due to his sociopath ex, Jack? The angelic inmate was explicitly hitting on his cellmate and it bugged him more than he would have ever admitted. Why did he felt that way? Was he... Was he jealous? No, it couldn't be. That didn't make any sense. He was with Dean only for protection, he had no kind of feelings towards him. Yet, as Jack reached out and grabbed his cellmate's biceps with a leer, Castiel's fists clenched reflexively.


"Lights out, dogs"

Dean looked at Castiel's body with lust as the lights went off and they were illuminated just by the pale moonlight. The two inmates were lying on the bottom bunk, one next to the other, wearing nothing but their underwear. Nighttime was when Castiel let go and allowed his cellmate to touch him. Now, after a bottle of wine, both men were kinda tipsy. "You're so sexy..." Dean commented, leaning out and nibbling at the other prisoner's lower lip. His hands moved all over his body and Castiel took courage, maybe because of the alcohol. He rolled Dean onto his back and then straddled his hips to kiss him. He tried to be in control as he smashed their lips together and his cellmate let him. Never had he ever taken the initiative before. They made out, their slick tongues pressing and tangling and rolling together. Against all odds, it was Dean to break the kiss and gasp for air. "Get off of me, so we can wank"

"What if I had something else in mind?"

"Well, in that case... bring it on"

Castiel winked, striving to flaunt his assertiveness. The truth was... he didn't know what he was doing. He was a little tipsy but it wasn't just that. Nervously, he slid down the other prisoner's body to his crotch, the big bulge right in front of him. And now? "Y-you ready?" Castiel asked both Dean and himself. Swallowing down, he shook his insecurities away and moved forward to mouth the outline of his cellmate's cock through his underpants. A soft moan escaped from Dean, hands squeezing the sheets as the other inmate nuzzled him. The warmth of his mouth on his erection... How much he had missed it. As Castiel kept bashfully kissing and sucking him through the thin fabric, his prick strained hard in his underwear, by now drenched in spit and precum. He was eager to grab his cellmate by his black hair and shove him onto his cock, but held back and let him lead the way. Castiel was riffing, proving himself in some way. Then, when he noticed the head of Dean's cock peeking out from the band of his boxers, glistening and wet, he felt somewhat reassured and made up his mind. So he drew back. "T-take off your underwear. I wanna suck you"

"You serious, Cas?"

"Try me"

Castiel didn't breathe as he held the other inmate's stare. Dean bit his lips, aroused, quickly yanking his underwear down and off of his feet. He sat up on his knees with his 9 inches stiff length failing around and threw his underpants to the far side of the cell. He really wanted to see what his cellmate was going to do now. Castiel just repositioned himself and lowered his face to his throbbing cock with nonchalance. He had never been so close to another man's junk before. Its strong, musky smell overwhelmed him and filled his nostrils, making him want to stop. No, he couldn't give up at this point. Tentatively, he stuck out the tip of his tongue and let it bump into the glans, withdrawing right after with his face screwing up in dislike. Dean couldn't hold back a chuckle.

Castiel felt self-conscious, realizing to act like a child. He kept his gaze down and enclosed his hand firmly around the base of Dean's cock only to bend over so that the head was pressed against his closed lips. Then, he opened his mouth just enough to slip the glans in and... almost gagged. The feeling was new. The shaft was hot and turgid but the taste was the sore point. It was... weird. Salty and rank at times as if Dean had just taken a piss and hadn't shaken it. Castiel didn't let it put him off, though. He engulfed more of the other prisoner's length, lips stretching around the thickness of his cock, and started to slurp. Up and down. Up and down. He bobbed his head, reaching up his cellmate's buttocks to pull him even closer. "Fuck, Cas... Continue and I'm gonna lose it" Dean warned as his hands shot out and grabbed the other inmate's head. He looked down at Castiel as tears sparkled in the corner of his eyes and ruthlessly pushed him further down on his prick. The result was obvious. Castiel choked, his gullet squirming around his cellmate's manhood, and tried to pull back. Strong hands held him there, though, only for an endless moment, and then let him up. He coughed and spluttered, panting heavily as saliva dribbled down his chin. Dean politely wiped the spit off with his thumb and pulled him up for a quick kiss. "Too rough? Want to give it another try?"

"I want you to stop saving my ass and start wrecking it"

"Wh- Are you for real, man? You sure?"

Castiel nodded, regretting it instantly. It was the alcohol talking, right? With anticipation, Dean spun him around before he could take it back and slipped one hand into his underwear. Soon his middle finger was tapping against the puckered hole, feeling it twitch at every touch. He had been dreaming about pounding that virgin ass for a long time. Castiel endeavored to relax as the other prisoner kept teasing him playfully, fondling and groping his butt. That wasn't easy for him. In no time his underpants were torn and his opening was exposed in plain sight. Dean's mouth watered. He expertly spread the round cheeks apart and dropped a large glob of saliva right onto his hole. He would have gotten 'em some lubricant if only he had known Castiel's intention to have sex. Well, maybe next time. Impatient, Dean placed the dripping head of his cock at the narrow opening and stopped to enjoy the view. It looked so small compared to his swollen glans... He couldn't look forward to popping that cherry. So he held his cock at the base with one hand and with the other gripped his cellmate's hips to have some leverage as he thrust forward.

Castiel felt a great pressure on his rear. He tried to breathe, to take off his mind from what was happening, still his body tensed up even more. Unfortunately for him, that didn't make Dean give in either. He just pressed harder, tougher, and eventually, the resisting ring of muscle surrendered to the intrusion. "Aaargh" Castiel shouted at the sudden pain. He felt split in two as the head plunged through and sank a few inches in. Dean didn't shove it further. He gave Castiel some time to adjust while gently stroking his back. God if he was tight... His glans was being clasped and pumped so good... Such torture not to move. After about a minute, the situation hadn't changed that much. Castiel was still a bundle of nerves, clearly suffering, but Dean couldn't wait any longer. He started out, progressively rocking his hips. He hoped that could help the other inmate somehow, perhaps by stimulating his sweet spots, but it only made things worse. "S-stop, please... T-take it out, Dean"

"Sssh, I know it hurts at first but soon it will feel better. Just, loosen up. You need to-"

"No, take it out! Take it out! I don't want to! I don't want to!"

Castiel broke down crying, loud and out of control. How could he be jealous of this? It was painful and he didn't like it. Why did he agree to all of this? Jack could have Dean, he didn't care. All he wanted right now was it to stop. "Hey, it's okay. It's okay, Cas. Calm down" Dean whispered as he cautiously pulled out his cock. He was a little worried since his cellmate looked so banged up. The moment their bodies parted ways, Castiel jumped up and rushed to the bars of the cell to be as far as possible from the other prisoner. Dean watched him sob and sniff, in silence, until he was a little bit quieter. "We don't have to do it if you're not ready. Come back here. Let me-"

"I want to go to my bed now. Alone. Please"

"Cas..."

Dean observed him wipe the tears from his eyes before turning around and stepping to the ladder. He didn't say a word as he climbed up and got on his bunk. He had pushed Castiel, hadn't he? He had been too hasty. Dean punched the mattress of his bed with all his might and felt somehow better. Meanwhile, as he lay on the side, tears had started falling down Castiel's cheeks again.