[Fic] Dean/Castiel/Benny - Sam's Dad
Title: Sam's Dad
Pairing: Castiel/Dean, Castiel/Benny/Dean
Summary: Seventeen years old Castiel and Benny double team their best friend's Dad.
Warning(s): Alternate Universe, Bottom!Dean, Boypussy, Underage, Threesome
A/N: Also on my AO3
They've been wanting to get Mr. Winchester alone for a while now. Right now they were spending the night at Sam's house in celebration of them graduating. Castiel had slipped Sam a 'special graduation drink' so that he'd knockout early into the night.
See, Castiel and Benny had planned it all out. They were going to get Sam out of their way first, then they would sneak downstairs where Mr. Winchester would be cleaning up the mess they made earlier, from there they would proceed to talk with Mr. Winchester and insinuate certain actions and hope Sam's Dad would take the hint.
If it backfired and Dean told Sam what happened. Well it was nice knowing them.
Castiel's attraction to the thirty-five year old had come after Sam had invited him and Benny over to swim. They had been thirteen at the time and were doing what teenagers do most, having fun. They were playing a game in the pool when Dean had stepped outside to join them.
"Hello boys," Dean had said in his gruff voice. "Hey Mr. Winchester," "Hi dad," "Uh - um - hello Mr. Winchester," they chorused back.
It wasn't his voice that attracted Castiel at first, but his physique. Dean was broad shouldered, had bowlegs, and a muscular form. What struck Castiel was the fact that Dean was wearing a bikini bottom and nothing else. He vaguely remembers Sam telling him that his Dad was a breeder, so instead of being born with a penis he had a vagina. Rare, but not unheard of. The clothing showed off his well toned thighs and hipbones while his black tank top hid the muscle underneath. Castiel thought he would faint. From that moment on Castiel popped a boner whenever he'd catch sight of a biking bottom.
Benny was a different story altogether. He had never thought of Mr. Winchester as a hot piece of ass until he caught a glimpse of what he was missing out on. He was the last football player in the school's locker room when he heard the moans. Ever the curious guy he decided to see who or what it was. When he made it to the other side of the room the moans got louder.
Catching movement inside his Coach's office, Benny looked in. The sight before him had the young man frozen on the spot. Kneeling on the floor was Coach Hendricksen with his face in-between Mr. Winchester's legs who was laying back on the desk with his legs spread wide. Coach Hendricksen was eating out Sam's Dad. Benny got out of their before they could catch him watching and left with a hard on. Once he got to the outside of the school he saw Sam who asked him if he'd seen his dad because his car is in the parking lot. Benny lied and said he needed to get home to avoid any awkward chat if Sam saw his erection.
Which brings them to now.
Sam is successfully knocked out and snoring in his bed and the two other boys are ready to set phase two in motion.
_________________________________________
Dean was sitting on the couch in the living room, nursing a beer and watching a Dr. Sexy marathon. He wondered if he should check up on the boys upstairs. His Sammy had graduated. God, he feels old, but damn proud at the same time.
He doesn't hear any noises coming from upstairs, checking the time it is ten o'clock at night. Though Sam may not have many friends he thought his son might have been invited to a party. He's grateful his son has two amazing best friends.
Checking for any noises from upstairs he decides to have some himself. Lifting his hips off the couch he pulls down his jeans and underwear, kicking them off to the side he sits back down. He hasn't had some time to himself since preparing for Sam's graduation date which was a month ago. He spreads his legs and plants them on the edge of the couch cushion giving him easier access to his pussy. He brings a hand down and brushes the pads of his fingers over his pussy lips. Fuck. He's so wet.
He doesn't hear the footsteps coming down the stairs.
_______________________________________________
Holy shit. This is better than they could have imagined, Castiel thinks. He turns his head to see Benny gaping at the sight before them. What a sight it is. From their view on the stairs they can see Mr. Winchester playing with himself on the couch placed diagonally on the floor.
They're so screwed. Hopefully in more ways than one.
Nodding his head toward the older man they descend the last steps. They round the couch and stand in front of the man who currently has his eyes closed and a finger tracing his second pair of lips. They stand there, waiting for the man to notice.
________________________________________________
Dean is moaning low in his throat as he remembers the last time he got fucked. His finger circles his pussy's entrance, slipping in just a little with his juices as lubricant. Thoughts of his afternoon spent with an eager coach come to mind. He remembers how the dark skinned man had tounged his cunt and the way the man had fucked him on his chair. Making him ride his big cock.
He hears a moan above him and his eyes fly open.
In front of him are his son's friends, staring at him with lust blown eyes and parted lips. He quicly pulls his hand away and uses both hands to pull down his shirt and cover himself.
A hand on his shoulder stops him and he looks up. Castiel is looking down at him. His cheeks flush red at being caught.
"You should continue" Castiel says, licking his lips.
"What d- do yo- you kids think you're doing?" Dean tells them with a stern face, failing to shrug off Castiel's hand on his shoulder. Benny notices his movements and pins Dean's other hand to the couch's back. This causes the older man's shirt to ride up, exposing his tan, toned stomach and wet pussy.
"Hey, let go!" Dean demands with an embarrassed flush. "Samm-!"
"Sammy won't be waking up 'til tomorrow, Mr. Winchester", Benny says, cutting him off. He kisses their interlocked hands, making Dean flush even harder. Castiel's grip on his shoulder makes him turn back to the teen towering over him. "We just want to have some fun too."
The blue-eyed teen pins his other hand to the back of the couch. Then both teens use their free hands to reach down between Dean's spread legs. They use their fingers to stimulate the nerves on the outside of the man's clit, eliciting a strangled moan from the man. The two teens kneel on each side of the man on the couch, continuing their ministrations. Benny lays kisses on the man's neck, rubbing his impressive stubble on him. Castiel licks a stripe up Dean's chin, pecking the man on the lips. Dean is stuck on wether he should fight to stop them or let them have their way. He hasn't gotten laid in some time.
Castiel's lips on his, as brief as it was, brings him out of his stupor and he tries bucking them off. This is wrong, he thinks, they're young and you're their friends father. His actions cause two of their fingers to breach his cunt and he howls in pleasure. "See what you did?", Castiel tells him, "There can be more of that if you want."
"You're Sam's friends. I can't do this with you," Dean pants.
"'S okay Mr. Winchester, we'll be real gentle," Benny reassures him with a kiss to his cheek. Dean gives a nod of finality at that and resigns himself to the two teens.
Castiel gets off the couch and kneels in front of the man, pulling his hips to the edge, startling Dean at how swift he moved. He didn't notice he had left his side. With his freed hand he lays it on top of the teens head, pulling him forward. Benny is busy licking and nipping Dean's neck to notice, but drawing out little moans from Dean, his finger still inside the man. Castiel had removed his finger as he got off the man and is now currently hovering his face over the man's pussy with the man's encouragment he shoves his face in. He licks around Benny's finger nipping the pink folds. He hears the man let out a whimper and he smirks.
Benny can't believe he's getting to taste the man he saw in the locker room and fantasized about in bed. He takes his finger out of the man and knows its dripping with pussy juice. He turns his face to the man and brings his finger up to the front of the older man's face. He seems to catch on because he latches his sinful lips around his finger, sucking it into his mouth. Benny can hear Castiel's slurps from his position on the ccouch and remembers about his hard dick is trapped in his jeans. Pulling his finger out of the man's mouth he stands up on the couch and unzips his pants, pushing them down to his ankles.
Dean is surprised at the teenagers well endowed body. He hasnt' seen a cock that thick since Sam's other father knocked him up. He can't wait to have it in his mouth, drooling over it. He plls Castiel's face further into his pussy, moaning as the chapped lips brush his lips. The teen is eating him out like he eats pie and its's damn good.
Something wet nudges his cheek and he turns his head to find a cock in his face and Benny smiling cheekily at him from above. Benny shakes his cock up and down, Dean's eyes tracking the movement, mouth parted in hunger. Dean eyes the weeping head and licks his lips, mouth opening to let the head in and proceeds to suckle on it. He puts his legs on Castiel's shoulders and tightens them to pull him even further into eating out his dripping cunt. He moans around the cock in his mouth as Benny thrusts hard into his mouth. He can feel himself getting close to the edge of release.
Castiel has pulled his pants down to his thighs and is fisting his cock with one hand while using the other to steady Dean's hips as he licks over his wet lips, mouthing the flesh before him. He's close to coming and he knows Mr. Winchester is too by the way his pussy flutters around his penetrating tounge. His face is covered in pussy juice and he can't wait for the man to come all over his face.
Benny's close to coming as well, and Dean knows this all too well if the stutter of his hips is any indication. His cock is huge and Dean loves how it fills his mouth and leaves it feeling full. He's caught by surprise as he feels a salty, sticky substance fill his mouth, eagerly swallowing it down. Dean's orgasm is triggered by Castiel's mouth and finger rubbing the top of his clit. He squirts on the teens face, moaning around the softening cock in his mouth. He know's Castiel came too by the way he's panting on his cunt.
Castiel pulls off the man as Benny settles on the couch cushion having pulled out his cock from the man, not bothering to pull his pants up. The blue-eyed teen wipes himself on his shirt and watches as Mr. Winchester pulls off his shirt to wipe the mess between his thighs and surprising the teen by wiping his face too. He looks over to Benny, who just gives him a thumbs up in return. He shakes his head with a smile and looks back to the older man.
Dean looks between the two and decides to relax against the couch, nude, and deciding on worrying about what just happened in the morning.
Pairing: Castiel/Dean, Castiel/Benny/Dean
Summary: Seventeen years old Castiel and Benny double team their best friend's Dad.
Warning(s): Alternate Universe, Bottom!Dean, Boypussy, Underage, Threesome
A/N: Also on my AO3
They've been wanting to get Mr. Winchester alone for a while now. Right now they were spending the night at Sam's house in celebration of them graduating. Castiel had slipped Sam a 'special graduation drink' so that he'd knockout early into the night.
See, Castiel and Benny had planned it all out. They were going to get Sam out of their way first, then they would sneak downstairs where Mr. Winchester would be cleaning up the mess they made earlier, from there they would proceed to talk with Mr. Winchester and insinuate certain actions and hope Sam's Dad would take the hint.
If it backfired and Dean told Sam what happened. Well it was nice knowing them.
Castiel's attraction to the thirty-five year old had come after Sam had invited him and Benny over to swim. They had been thirteen at the time and were doing what teenagers do most, having fun. They were playing a game in the pool when Dean had stepped outside to join them.
"Hello boys," Dean had said in his gruff voice. "Hey Mr. Winchester," "Hi dad," "Uh - um - hello Mr. Winchester," they chorused back.
It wasn't his voice that attracted Castiel at first, but his physique. Dean was broad shouldered, had bowlegs, and a muscular form. What struck Castiel was the fact that Dean was wearing a bikini bottom and nothing else. He vaguely remembers Sam telling him that his Dad was a breeder, so instead of being born with a penis he had a vagina. Rare, but not unheard of. The clothing showed off his well toned thighs and hipbones while his black tank top hid the muscle underneath. Castiel thought he would faint. From that moment on Castiel popped a boner whenever he'd catch sight of a biking bottom.
Benny was a different story altogether. He had never thought of Mr. Winchester as a hot piece of ass until he caught a glimpse of what he was missing out on. He was the last football player in the school's locker room when he heard the moans. Ever the curious guy he decided to see who or what it was. When he made it to the other side of the room the moans got louder.
Catching movement inside his Coach's office, Benny looked in. The sight before him had the young man frozen on the spot. Kneeling on the floor was Coach Hendricksen with his face in-between Mr. Winchester's legs who was laying back on the desk with his legs spread wide. Coach Hendricksen was eating out Sam's Dad. Benny got out of their before they could catch him watching and left with a hard on. Once he got to the outside of the school he saw Sam who asked him if he'd seen his dad because his car is in the parking lot. Benny lied and said he needed to get home to avoid any awkward chat if Sam saw his erection.
Which brings them to now.
Sam is successfully knocked out and snoring in his bed and the two other boys are ready to set phase two in motion.
_________________________________________
Dean was sitting on the couch in the living room, nursing a beer and watching a Dr. Sexy marathon. He wondered if he should check up on the boys upstairs. His Sammy had graduated. God, he feels old, but damn proud at the same time.
He doesn't hear any noises coming from upstairs, checking the time it is ten o'clock at night. Though Sam may not have many friends he thought his son might have been invited to a party. He's grateful his son has two amazing best friends.
Checking for any noises from upstairs he decides to have some himself. Lifting his hips off the couch he pulls down his jeans and underwear, kicking them off to the side he sits back down. He hasn't had some time to himself since preparing for Sam's graduation date which was a month ago. He spreads his legs and plants them on the edge of the couch cushion giving him easier access to his pussy. He brings a hand down and brushes the pads of his fingers over his pussy lips. Fuck. He's so wet.
He doesn't hear the footsteps coming down the stairs.
_______________________________________________
Holy shit. This is better than they could have imagined, Castiel thinks. He turns his head to see Benny gaping at the sight before them. What a sight it is. From their view on the stairs they can see Mr. Winchester playing with himself on the couch placed diagonally on the floor.
They're so screwed. Hopefully in more ways than one.
Nodding his head toward the older man they descend the last steps. They round the couch and stand in front of the man who currently has his eyes closed and a finger tracing his second pair of lips. They stand there, waiting for the man to notice.
________________________________________________
Dean is moaning low in his throat as he remembers the last time he got fucked. His finger circles his pussy's entrance, slipping in just a little with his juices as lubricant. Thoughts of his afternoon spent with an eager coach come to mind. He remembers how the dark skinned man had tounged his cunt and the way the man had fucked him on his chair. Making him ride his big cock.
He hears a moan above him and his eyes fly open.
In front of him are his son's friends, staring at him with lust blown eyes and parted lips. He quicly pulls his hand away and uses both hands to pull down his shirt and cover himself.
A hand on his shoulder stops him and he looks up. Castiel is looking down at him. His cheeks flush red at being caught.
"You should continue" Castiel says, licking his lips.
"What d- do yo- you kids think you're doing?" Dean tells them with a stern face, failing to shrug off Castiel's hand on his shoulder. Benny notices his movements and pins Dean's other hand to the couch's back. This causes the older man's shirt to ride up, exposing his tan, toned stomach and wet pussy.
"Hey, let go!" Dean demands with an embarrassed flush. "Samm-!"
"Sammy won't be waking up 'til tomorrow, Mr. Winchester", Benny says, cutting him off. He kisses their interlocked hands, making Dean flush even harder. Castiel's grip on his shoulder makes him turn back to the teen towering over him. "We just want to have some fun too."
The blue-eyed teen pins his other hand to the back of the couch. Then both teens use their free hands to reach down between Dean's spread legs. They use their fingers to stimulate the nerves on the outside of the man's clit, eliciting a strangled moan from the man. The two teens kneel on each side of the man on the couch, continuing their ministrations. Benny lays kisses on the man's neck, rubbing his impressive stubble on him. Castiel licks a stripe up Dean's chin, pecking the man on the lips. Dean is stuck on wether he should fight to stop them or let them have their way. He hasn't gotten laid in some time.
Castiel's lips on his, as brief as it was, brings him out of his stupor and he tries bucking them off. This is wrong, he thinks, they're young and you're their friends father. His actions cause two of their fingers to breach his cunt and he howls in pleasure. "See what you did?", Castiel tells him, "There can be more of that if you want."
"You're Sam's friends. I can't do this with you," Dean pants.
"'S okay Mr. Winchester, we'll be real gentle," Benny reassures him with a kiss to his cheek. Dean gives a nod of finality at that and resigns himself to the two teens.
Castiel gets off the couch and kneels in front of the man, pulling his hips to the edge, startling Dean at how swift he moved. He didn't notice he had left his side. With his freed hand he lays it on top of the teens head, pulling him forward. Benny is busy licking and nipping Dean's neck to notice, but drawing out little moans from Dean, his finger still inside the man. Castiel had removed his finger as he got off the man and is now currently hovering his face over the man's pussy with the man's encouragment he shoves his face in. He licks around Benny's finger nipping the pink folds. He hears the man let out a whimper and he smirks.
Benny can't believe he's getting to taste the man he saw in the locker room and fantasized about in bed. He takes his finger out of the man and knows its dripping with pussy juice. He turns his face to the man and brings his finger up to the front of the older man's face. He seems to catch on because he latches his sinful lips around his finger, sucking it into his mouth. Benny can hear Castiel's slurps from his position on the ccouch and remembers about his hard dick is trapped in his jeans. Pulling his finger out of the man's mouth he stands up on the couch and unzips his pants, pushing them down to his ankles.
Dean is surprised at the teenagers well endowed body. He hasnt' seen a cock that thick since Sam's other father knocked him up. He can't wait to have it in his mouth, drooling over it. He plls Castiel's face further into his pussy, moaning as the chapped lips brush his lips. The teen is eating him out like he eats pie and its's damn good.
Something wet nudges his cheek and he turns his head to find a cock in his face and Benny smiling cheekily at him from above. Benny shakes his cock up and down, Dean's eyes tracking the movement, mouth parted in hunger. Dean eyes the weeping head and licks his lips, mouth opening to let the head in and proceeds to suckle on it. He puts his legs on Castiel's shoulders and tightens them to pull him even further into eating out his dripping cunt. He moans around the cock in his mouth as Benny thrusts hard into his mouth. He can feel himself getting close to the edge of release.
Castiel has pulled his pants down to his thighs and is fisting his cock with one hand while using the other to steady Dean's hips as he licks over his wet lips, mouthing the flesh before him. He's close to coming and he knows Mr. Winchester is too by the way his pussy flutters around his penetrating tounge. His face is covered in pussy juice and he can't wait for the man to come all over his face.
Benny's close to coming as well, and Dean knows this all too well if the stutter of his hips is any indication. His cock is huge and Dean loves how it fills his mouth and leaves it feeling full. He's caught by surprise as he feels a salty, sticky substance fill his mouth, eagerly swallowing it down. Dean's orgasm is triggered by Castiel's mouth and finger rubbing the top of his clit. He squirts on the teens face, moaning around the softening cock in his mouth. He know's Castiel came too by the way he's panting on his cunt.
Castiel pulls off the man as Benny settles on the couch cushion having pulled out his cock from the man, not bothering to pull his pants up. The blue-eyed teen wipes himself on his shirt and watches as Mr. Winchester pulls off his shirt to wipe the mess between his thighs and surprising the teen by wiping his face too. He looks over to Benny, who just gives him a thumbs up in return. He shakes his head with a smile and looks back to the older man.
Dean looks between the two and decides to relax against the couch, nude, and deciding on worrying about what just happened in the morning.