Movie Night
After their father had left for the next hunt Dean allowed Sam to decide on a movie he wanted to watch.
Heating up some popcorn Dean came to sit on the couch with Sam, but tonight he was gonna torture his little brother.
"C'mere Sammy."
Dean pulls Sam onto his lap when the movie starts and he smiles down at his little brother.
Slowly he begins stripping Sam of his clothing leaving only his boxers and then he reaches for his handcuffs and lifts Sammy's arms above his head locking them in place.
Sam whines as he recognizes the mood his big brother was in and that he had every intention of dragging this out on him.
Dean gave an evil smirk that gave Sam a nervous chill.
"You still as ticklish now as you were as a kid Sammy boy?"
"What? No!" Sam answered quickly.
"You sure?" Dean taunted "Cause I think you are."
Dean used a hand to poke his little brother's naked sides.
Sam struggled futilely in his brother's lap who had him vulnerable, naked restrained.
With Sam's wrists handcuffed above his head, Dean's fingers danced lightly over his brother's tummy and sides causing Sam to gasp and grunt, while the other hand teased his spine.
"Dean! Please don't!" Sam pleaded through weak laughter as Dean dragged it out.
"Sorry Sammy but ya lied to me, and now you're gonna get punished."
Dean chuckled evilly and started to wiggle his fingers into the deeper tissue and muscle of Sammy's tummy.
Sam's begging turned to a sound of pleading laughter, "Nononononono!"
Dissolving into cackling laughter, Dean relished in the sound and scribbled his nails across Sam's midsection.
Lifting his fingers further up a bit, Dean waited for Sam to realize what was coming, and gave him a moment.
When Sam saw his evil grin and the position his hands were in his eyes widened, "W-wait Dean, no don't! Not that! Please!"
"Sammy boy you must be insanely ticklish I've never heard you beg that hard before."
Dean started to spider his fingers in the hollows under Sam's arms.
"NO DEAN PLEHEHEASE!" Sam shrieked his face red with laughter, his cock now extremely hard.
"You sure you want me to stop? It kinda sounds like you like this."
Dean teased as Sam gasped at his soft touches.
He wiggled his fingers towards Sam's middle and Sam sucked in a breath.
"Dean don't!"
"You really mean that? I don't think so."
Dean teased as his fingers descended to skim over Sam's tummy.
He dove both fingers under Sam's arms and Sam tried to bring his arms down uselessly trapping his brother's wiggling fingers under his arms.
"HAHAHAHAHAHAHA NOOOOOOO"
"Man this is kinda fun torturing you like this I could do this all night into tomorrow!"
Dean slowly teasingly walked his fingers over Sam's sides making Sam squirm and let out a slight giggle.
He grinned and said, "Besides it's fun to make you squirm and beg."
Leaning into his ear he whispered, "This is gonna be so fun you know knowing how much you like this now I can tickle and tease you naked on my lap like crazy all the time…"
Dean ground his hips slightly against him and made Sam gasp.
His mischievous fingers started to knead softly into Sam's sides making Sam whine with urgency as Dean pressed harder against Sam's crotch.
Tickling up and down his back with one hand, he moved the other hand to Sam's crotch to rub against him.
Sam moaned eagerly and began to desperately thrust upward at Dean's playful touch.
Continuing to tease his cock, his other hand came up to trace patterns on Sammy's tummy.
Sam gasped into the ticklish sensation.
Dean grinned rocking his hips against Sam in steady thrusts all the while tickling Sam lightly enough not to cause hysterics but enough to make him squirm slowly and enjoy it.
He immediately went to one of his brother's worst spots his neck.
The older Winchester's fingers danced unbearably lightly against the soft skin of Sam's overly sensitive neck.
Dean just chuckled wiggling his fingers over a few more areas that made Sam jump his armpits, against his ribs, his collarbone, all over his sides and tummy.
Slowing down a bit he slowly trailed a finger up and down over Sam's soft skin.
Sam twitched and giggled lightly and he started to gently spider his fingertips over his brother's tummy.
He then attacked his mid section with much more vigor getting a jolt out of the naked boy.
Dean wiggled his fingers into the taut muscles under his little brother's ticklish arms.
Keeping Sam held against him he poked, scribbled scratched and tickled with his other hand all over Sammy's tummy.
His fingers danced all across his tummy and circled his belly button and occasionally wiggling inside.
Dean laughed at his brother's helplessness and started to squeeze Sam's sides as Sam squeaked and shook with laughter, squirming.
His fingers traveled upwards and began to press into the spaces between Sam's ribs as Sam cackled helplessly.
The upper parts of Sam's ribs were especially sensitive and Dean's fingers scratched against those spots making Sam lose most coherence to beg.
Dean's other hand scribbled all over Sam's underarm making Sam scream.
Deciding to be kind for a moment he snapped down to Sammy's side trapping Dean's hand in his armpit.
Dean chuckled and wiggled his fingers under Sam's arm.
Then again relaxing Dean ran a finger gently down Sam's back from the top of his neck down his bare back.
He then ran a finger up and down Sam's sides.
Dean then starts to slowly drag his nails over Sam's kneecaps pausing to scribble his fingers over Sam's lower inner thighs.
"NO! Nononononohohohonoo."
Dean lightly tickles behind his little brother's knees laughing at him.
Then he lightly tickles along his tummy and sides again.
He runs his fingers slowly all across Sam's sensitive tummy, digging into the skin above his pant line, and just under his bellybutton occasionally dipping a finger in making him gasp.
Dean wiggles his fingers in the spaces between and squeeze and pinch them.
He lightly runs his fingers from the bend of Sam's elbow slowly down toward his armpits.
The movement is agonizingly slow and torturous as Dean purposefully drags out the sensation as long as he can.
He wanted to build Sam up to the point that he would lose his mind the moment Dean's hand connected with his underarms again.
Sam screams through his laughter as Dean starts to scratch and wiggle his fingers in the hollows of Sam's underarms.
"Aaaaawwww does this tickle Sammy? Bet you wish you could move right now don't, you?"
Dean chuckles evilly as he runs his nails all over Sam's upper body.
He rakes his fingers up and down his ribs, poking and squeezing his sides skittering his nails all over his tummy.
Dean then begins digging into the muscle and skin tweaking and pinching his hips and wiggling his fingers under Sam's arms.
Then he digs into the space just under his ribs.
Dean's fingers scribble up and down Sam's ribs and down to his sides.
He hits one particularly sensitive spot on his lower ribs that drives Sam crazy and he hones in on that spot and teases Sam until he is red from laughing and yelling.
Dean slides his fingers under one of Sam's arms attacking the spot and teasing, "Still so ticklish Sammy."
He suddenly wiggles his fingers against Sam's neck down his back watching Sam helplessly scrunch as best as he can.
All that does is trap Dean's hand there and he wiggles his fingers there over and over.
Dean casually lightly wiggles his fingers there.
He scribbles his fingers against Sam's neck and collarbone and then so slowly around his shoulder blades down the dip of his spine.
When Dean's fingers slow Sam reluctantly stretches his neck out only for Dean to take advantage of his brother's helplessly exposed neck.
Dean scratches his nails against it making Sam jump with surprise and try to scrunch up again.
He finally squeezes his fingers out from under Sam's neck and dives them down to tickle Sammy's tummy skittering his fingers all around.
Dean digs into one really ticklish spot on his tummy making Sam slightly buck his hips with his hands cuffed above his head.
Then Dean's fingers are at the tops of Sam's ribs again and Sam begins cackling helplessly.
He digs his fingers into his brother's ribs hard.
Sam throws his head back squeezing his eyes shut laughing.
Then he digs his fingers into Sam's ribs even harder and laughs when Sam bucks.
Dean shoots his hands up under his brother's armpits Sam jerking as Dean hits a particularly sensitive spot.
As he lightens up Sam raises his arms a little, only for Dean to smirk evilly and give another tickle assault on his underarms.
Reaching forward he rubbed the palm of his hand teasingly up and down Sam's trapped cock in his boxers taunting, "This getting you really excited Sammy boy? Yeah I can feel it."
Sam let out a gasp as Dean's other hand made its way down his naked chest fingers teasing his nipples to complete hard and erect.
Dean licked his thumb and forefinger and started lightly stroking, pinching, teasing and tickling his nipples slowly.
"Man you love that don't you Sammy?"
Then he started lightly running his fingers up and down over his bare ribs from his hips to his pits and back down.
"Yeah that's right Sammy squirm and laugh for me love to watch you squirm as I torture you."
"No! Stop! Can't take it!"
"Yeah that's it beg for me my beautiful boy beg."
He continued his relentless assault on his ticklish sides moving faster and more furious with each stroke.
Sam suddenly felt Dean's fingers slowly trace a path up and down the length of his naked soles.
Dean's fingers lightly grazing, his bare soles, slowly, torturously, tracing a path from heel to toe over and over.
He felt Dean play with his nipples again with his other hand as he ran his fingers up and down Sam's sides.
Feverishly, he ran his fingers all over Sammy's ribs, armpits, tummy up and down and then over to his back lightly stroking and teasing.
Sam could feel his fingers dancing over his nipple while his other fingers playfully glided up and down his spine.
Dean felt Sam shiver in his lap as he stroked his spine teasingly slow up and around his shoulder blades, up to the back of his neck and all the way back down again.
Bringing his hand down to his crack he glides his fingers there softly tickling and then circling his hole.
Feeling Sam trying to block his hole he shook his head and teased, "Uh-uh sweetheart. Be a good boy and let daddy see you."
Dean's thumbs press against his rim lightly making Sam gasp and moan.
"What do you want sweetheart?" Dean asks softly tickling him again.
"Want you to fuck me."
Dean's fingers brush his prostate teasingly and he arches slightly and gasps as Dean gives a jab at the sensitive bundle of nerves.
He then decides to kick the teasing up a notch and leans in saying to Sam, "Now Sammy five minutes I want to test you to keep quiet and if you can't we drag this out."
Smirking he watches as Sam closes his eyes preparing himself but probably thinking it could not be that difficult.
"Okay starting now."
Sam suddenly feels a slow teasing hand on his cock stroking and can't help but moan at the sensation.
Dean laughs at the sound low and breathy against his ear making Sam groan.
Sam doesn't make any other sounds for a moment but then Dean presses the tip of a finger against the slit and he wails.
Dean does this same motion again and again and after about the fifth time Sam started to plead and beg.
After a few more teasing minutes Dean pulls away but not before letting his fingers tickle slowly across Sam's abs and up to playfully twist his nipples.
Lightly teasing Sam's cock again with ghosting strokes he went about five seconds before stopping and starting again laughing at his brother's frustration.
Dean blows gently on Sam's cock watching it twitch with amusement.
He lightly dug his fingers into the soft flesh above Sam's belly button and then just stroked across back and forth until Sam began to just giggle.
The other hand now having both hands out and free he teased it all across Sam's body making Sam shudder and shake uncontrollably.
Bringing it down he brought Sam to climax by stroking and teasing his cock and worked him over laughing at him until he passed out.