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“Dean! No way am I gonna let you do that!” Seventeen year old Sam whined unhappily as he paced up and down in their motel room.
They had just returned from a training session that revolved around trust. Dean had bet that Sam wouldn’t trust them, Sam agreed to the bet and lost. Now his part of the bargain was to trust them in something very intimate.
“Dude you lost the bet! You agreed to do anything I wanted if you lost, I want you to let me finger you, while dad watches.” Dean said smugly.
Sam gave him a look. “I said no Dean! I can’t!”
Sam sat on the edge of his bed and huddled in on himself. Sam had never bottomed for his dad or brother, not trusting them to be gentle; especially since he’d seen them with each other. Dean sighed and sat next to him, he slung a comforting arm around him.
“Come on Sammy….it’s not that bad man, I’ll make it good for you; I promise.” Dean said in a persuading tone.
Sam looked up at John. “Dad you can’t think this is a good idea! It’s not fair! Make him pick something else for me to do!”
“Sorry Sam, it’s not fair if you get to do something you like after losing a bet.” John said with a knowing smile and shake of the head. “Lay back and let your brother work his magic.”
“But-!” Sam started desperately.
John interrupted with a soft kiss to his youngest’s lips. When he drew back he gently unbuttoned Sam’s shirt, and pushed him to lie on his back on the bed. Sam looked up at him worriedly. John stroked his hair soothingly and lay beside him with a hand on his belly.
Dean crawled up to sit between his legs and he made quick work of removing Sam’s jeans. He pushed Sam’s legs wider apart and reached to gently fondle his sack. Sam grunted and rocked his hips up as Dean’s hand moved to his dick, stroking the flesh to full hardness. Dean smiled when he saw how relaxed Sam was becoming. He took the chance to move his hand down to try at Sam’s entrance.
Sam balked and grabbed at Dean’s wrist. “No! Wait!”
“It’s alright Sammy...just breath.” John took Sam’s hands in his own and kept them away so that Dean could work.
Dean smiled at Sam comfortingly and covered his fingers in lube. “Going in Sammy. Just one finger.”
Sam squirmed up the bed as Dean pressed a finger into his entrance. Dean shushed him and stilled his finger once he was a knuckle in.
“Doing good Sammy...” He leaned up to kiss his brother’s cheek.
John smiled and released Sam’s hands so that he could rub his son’s sides. “See? It ain’t so bad kiddo, just relax.”
“Feels strange.” Sam said in a choked voice.
“I know, don’t worry, it’ll start feeling good soon Sammy; trust me.” John said gently.
Sam squirmed and Dean began moving his finger in and out of his brother, applying extra lube as he went. Sam panted softly and gripped his father’s arm and the sheets beneath himself. Dean kissed his belly softly and licked the soft skin of his navel.
Sam keened weakly at the attention to such a sensitive spot. Dean took his chance to press a second finger into Sam, Sam groaned in pain and looked down at him wearily.
“Easy Sammy...”John pressed himself against his son’s side and reached out to stroke Dean’s hair. “Gentle Dean, don’t want to scare him off.”
“Yea, want him to like this….” Dean murmured against Sam’s navel.
He gently scissored his fingers in Sam and smiled when Sam moaned and held still for him. Dean pushed a bit deeper and crooked his fingers, looking for Sam’s prostate. Sam suddenly cried out and a squirt of precum escaped the tip of his cock.
John smiled and kissed his cheek. “Atta boy Sam…. it can feel good.”
“Uhgn...Dean...st-stop!” Sam pleaded.
Dean and John exchanged surprised looks. “What do you mean? You’re enjoying this Sammy?”
“Please I can’t! Dad please, I can’t-” Sam struggled to explain himself.
“Shhh Sammy, I know it’s hard to relax and trust us Sam but please try; we won’t hurt you.” John soothed his son, nodding for Dean to continue.
Dean carefully inserted a third finger and Sam clenched tightly around his fingers. Sam moaned and kicked lightly at Dean’s thigh. Dean pushed Sam’s leg away and exposed him further. He began moving his fingers in and out a little faster, crooking his fingers each time to hit Sam’s prostate.
Sam cried out and clung harder to John. The oldest Winchester smiled and nuzzled his ear.
“Look Sammy, you’re doing it, you’re almost bottoming to us. You’re doing good kiddo….you’ll be used to it in no time...I bet he’s real deep in you, can you feel? Talented isn’t he? When you’re more relaxed about this we’ll show you Dean’s other talents.” John whispered in Sam’s ear, trying to turn him on.
For Sam it was arousing to be told about all this, and he felt more precum drip from his cock as his father told him how good he was being. Dean was at full pace and the stimulation was intense, John slid a hand down to rub at his perineum and fondle his sack. It became too much for Sam and he gasped on a sob.
“Dad, I..can’t-” Sam pleaded as he held back.
“Let it go Sammy, trust us.” John growled back in his youngest’s ear.
Sam keened as he came on his stomach, thrusting his hips up at the air and then rutting down onto Dean’s fingers. He lay spent and panting as Dean and John lavished him with kisses and kind words.
“Did so good Sammy-”
“So hot-”
“Not so bad was it? Gonna love bottoming proper...”
“Mmmm so tight around my fingers, can’t wait to bottom you all the way..”
Sam sighed and relaxed as he took in their murmurs and whispers of admiration and affection. He couldn’t believe he’d been able to do it but he was kind of glad. Now he had them feeling good about themselves and he had broken through a barrier.
“I know that was hard for you Sam, and I’m proud you did it. It showed a lot of trust in us, especially since you’re always so anxious about being weaker.” John told him later, after he and Dean had sex, when Dean was asleep. “It’s not a show of weakness, you were brave to get through that. In the morning we can talk about doing more if you want?”
Sam nodded quietly and cuddled against his father with Dean at his back.