Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/ works/10551748. Rating: Explicit Archive Warning: Underage Category: M/M Fandom: Supernatural Relationship: Castiel/Dean_Winchester, Benny_Lafitte/Dean_Winchester Character: Dean_Winchester, Benny_Lafitte, Castiel Additional Tags: Dubious_Consent, Humiliation, small_cock, Anal_Fingering, Anal_Sex, Feminization, Cock_Slut_Dean, Bottom_Dean, Coming_Untouched Stats: Published: 2017-04-06 Words: 1338 ****** Deans Little Secret ****** by orphan_account Summary Deans embarrassing little secret is no longer secret... Fourteen year old Dean waited until the last of the boys left the showers before hurrying over to the furthest stall and stripping off his towel and turning the shower on. He washed and rinsed as quickly as he could, not wanting to risk exposure any longer than absolutely necessary. He wasn't the most popular kid in school but he knew that if anyone found out his secret that he would instantly become a target for all the bullies. His parents told him over and over that it was nothing to be ashamed of, it was completely natural. He was still perfect to them, but Dean knew that in the real world, if people found out, it would be social suicide. Turning off the shower he haphazardly rubbed himself dry with the towel and turned to exit the stall. To his utter horror he realized he was no longer alone in the shower room, before him stood two of the most popular guys in the entire school. Both were staring at him wide eyed as they took in his naked body. They both smirked as their eyes landed on his tiny one and a half inch cocklet. "Where the fuck is your dick Winchester?" Benny sneered. "I don't think Deanna has a dick Benny, looks to me like she's got a little clit." Castiel laughed in reply. Benny turned to wink at his friend and said, "I think you're right Cas, that tiny little thing can't be called a cock." Dean bowed his head as a blush covered his pale freckled cheeks, praying to whoever would listen that this was only a nightmare and that he would wake up safe in his bed at any moment. Cas snickered as Benny crowded Dean into a corner and knelt down to stare at his pathetic cocklet. He took the tiny protrusion between his thumb and forefinger and began to rub it until it hardened. "Damn, would you look at that, it's hard and it's still not even two inches! Man that's just fucking embarrassing!" Benny chuckled as he continued to fondle the humiliated boy. "Maybe you should check to see if he had a pussy under that clit." Cas suggested with a leer. "Mmmm, I think you're right pal. Well Deanna, you got a pussy under there or what??" Dean shook his head rapidly, tears forming in his eyes as the elder of the two boys flipped him around and bent him over, exposing his plump ass to them. Cas moved to stand beside the trembling boy and slid his hand along his buttocks until he encountered his furled hole. "Yep, looks to me like she has a real tight little puss right here Ben." Cas replied as his finger circled the fluttering rim. Benny sucked a finger into his mouth, getting it nice and wet before inserting it into the 14 year olds twitching rim. Dean whimpered as his virgin ass was invaded by a thick finger sliding into him. He clenched tightly around the appendage as if somehow that could stop it from entering him. Benny chuckled at his resistance and began to thrust his finger in and out of the boy to get him used to the feeling of being penetrated. After several moments he added a second finger, curling around, searching for that little bump inside him. Dean yelped as the larger boy suddenly rubbed something inside him that had his cock leaking and his toes curling in pleasure. He moaned wantonly as two fingers turned into three and three into four, all the while massaging that delightful place inside him. Cas lowered his shorts until his rigid cock bounced free as he watched the show. He stroked his thick meat as he murmured, "Looks like you found the little girls g-spot there Benny, look how she's trying to fuck herself onto your fingers." Benny licked his lips and stood up. "He's obviously never going to get a girlfriend with a puny thing like that, he couldn't fuck anyone with it, that just means baby girl here was only meant to be fucked, so why don't we show her what a real cock looks and fucks like?" Cas' reply was flip the boy over and lay him down on the cold floor of the shower room. He moved between the boys slim thighs and slid his slick, 8 inch cock along his tiny cocklet. "You see Deanna, this is what a proper dick looks like, you see how big and thick it is? See this fat head and this huge nut- sack? That's what a real man's cock looks like, not like your tiny little baby cock." Deans lips quivered as he tried to hold back the tears of humiliation at the 17 year olds words. He hated the boys for their cruel words and yet he found he couldn't stop himself from thrusting his ass towards the prick sliding against his finger-fucked hole. Cas pulled the boys hips upward and in one quick thrust, slammed his cock inside. Dean shrieked as he was impaled by that long hard cock. He was given little time to adjust as Cas quickly began to hammer into him. Cas angled his cock until he was rewarded with the mewls of the boy beneath him. "Aahhhhnnn... Mmmnnnn... O-oohhhh..." Dean moaned as his prostate was repeatedly battered. His cocklet jerked once as he came, untouched, over his heaving belly. Cas groaned as the boys hole tightened with his orgasm. A few more deep thrusts and he was coming, filling the tiny teens ass with his thick seed. Pulling out he slumped to the side as his best friend took his place, slamming his massive 9 inch cock into his fucked out boy-pussy. Benny, horny as hell after watching the pretty boy take his first cock, wasted little time before jack-hammering into his used hole. His friends cum made the slide much smoother as he raped his tight fuck-hole. "Fuck, fuck, so fucking tight! Mnnn, you love it don't you baby girl, love having a big thick cock inside you, fucking your tight little pussy, ramming your g-spot. You gonna cum baby, come on, cum around my cock like a good little girl." Benny grunted as he picked up his pace, fucking harder, deeper than ever. Dean was mewling like a kitten as the older boy rammed his huge prick into his tight pussy. His little clitty throbbed, hard once more as his g-spot was repeatedly assaulted. "Come on baby girl, tell me how much you like it." Benny coaxed the trembling boy. Deans long, lash covered green eyes peered into his as he begged, "Mmnnnn... P- pleasee... F-fuck my p-pussy... need to cum! please!! aahhhhmmm...." Bennys cock, if possible, became even harder at the words falling from the fourteen year olds pouty pink lips. Who knew that such a sex kitten was hiding under that innocent pretty boy facade. Dean moaned as he felt his body tense up, and he came a second time while impaled on a thick hard cock. His tiny balls drew up and spilled all over his twitching cocklet. He whimpered as the buff boy above him continued to slam his turgid cock into him. Several minutes later he felt a torrent of thick cum unleashed inside him, filling his fucked out boy pussy with copious amounts of his hot cream. "Fuck. That was the best fuck of my life. I will definitely be cumming back for a repeat performance baby girl." Benny praised as he let his softening cock slip from the boys now gaping hole. "I agree Benny, his pussy is tighter than any girl I've ever fucked. And I don't think baby girl would mind one bit if we used her pussy again." Cas smirked as he eyed the blissed out boy laying between them, legs spread wide, giving them a glimpse of his well fucked pussy leaking their combined cum. Yes, they definitely couldn't let such a rare find continue to be so neglected...   End. Please drop_by_the_archive_and_comment to let the author know if you enjoyed their work!