Sam's Study Time
Dean climbed into bed sitting beside his vulnerable little brother.
He had Sam sitting down mostly naked but his boxers, blindfolded, and vulnerable for Dean to tease him as long as he pleased.
Reaching down he stroked a hand over Sam's shoulders and down along one arm, and then ran the back of his hand lightly over Sam's chest.
Feeling the light touch of Dean's hands Sam shivered and closed his eyes.
Laying back Dean ran his hand so slowly over Sam's back and sides lightly tickling him.
Noticing Sam's obvious shiver, he whispered, "You okay Sammy?"
Sam swallowed, "Yeah."
"You like this? Enjoying it?"
Dean ran his hand over Sam's vulnerable, naked skin.
"Yeah you always did like this didn't you Sammy? Being stroked teased and tickled just like this."
Gently then Dean placed his fingers under Sam's chin tilting his face up.
"Look at me Sammy."
Sam met Dean's eyes asking, "What?"
Dean smiled distracting him and then reached down with one hand brushing Sam's cock and heard Sam's breath catch.
His fingers continued to lightly stroke and tease the length of Sam's cock.
Sam was shivering and shuddering uncontrollably under the sensation, as Dean felt his cock grow harder.
He tugged lightly on Sam's cock making him gasp.
"Stay still."
Dean continued to lightly pull on Sam's cock, "How's this feel Sammy? Feel good?"
"Hands up and behind your head Sammy and keep them there."
Reaching above, Dean slowly dragged the tips of his fingers down from his wrists to his elbows, down to his armpits and just tickled and scratched there lightly.
Lying with Sam on the bed he lightly teased his sides with feather like tickling touches.
Having fucked Sam over and over a few times earlier, he was aware of how sensitive Sammy would be.
He glanced down and saw the rapid rise and fall of Sam's chest as his brother tried to ride out the feelings he was forcing him to endure.
Then without a moment's notice Sam felt Dean's light tickling fingers against his sides dig in just between his ribs.
Dean scraped his blunt nails against his brother's sensitive skin.
The older brother watched as Sam's eyelids fluttered shut, as he heard him laugh breathlessly, before he moaned and released helplessly.
"You like this Sammy?" Dean whispered in his ear with a wicked grin as Sam shivers.
Dean could tell in that moment that Sam's head was in the clouds with the intensity of his orgasm, and was unable to respond.
The cum all over his tummy and still dripping from his slit said it all
Seeing Sam blush made Dean smirk knowing Sam got off on him tickling him.
"Yeah you like it a lot."
I'm gonna tease the hell out of you Sammy" as he glides his fingers slowly upwards dancing his fingers across Sam's sides a little lighter than before.
He gives just a ghostly touch that makes Sam shiver.
"And watch you writhe for me, tickle you lightly like this until you're begging me to cum, shaking, trembling with need but I won't let you, you're gonna be beggin me Sammy," Dean whispers.
"D-Dean ppplllleeeaaasee hahaha."
"Beg me for it Sammy baby come on laugh for me that's it let me hear ya."
Dean starts to tickle all over just a ghostly light touch enough to make Sam giggle but not laugh too hysterical as they had all day and night.
Sam breaks out into giggles, crying from laughing too hard, trying to protect himself, but he was restrained.
He glanced down to see Sammy's cock bright red almost purple, hard against his flat tummy, leaking pre-cum and Dean tickles over his sensitive belly until he's panting.
Tears streamed down Sammy's face from the tingling all over, as Dean teased softly.
"Come on harder for me baby harder, laugh it out come on you know you want it, tickle tickle tickle tickle tickle Sammy cootchie cootchie cootchie coo."
"Dean, Dean" Sam gasps afraid of cumming too soon as Dean continues to tickle torture him softly.
"Please, please please."
However Dean shows no mercy.
Sam feels Dean's fingertips lightly dance over his nipples, up and down his sides, stroking under his armpits, around his chest, up to his neck and around his shoulders.
Laughing uncontrollably Sam throws his head back pleading for mercy he knew that would not come.
They continue like this for about another twenty to thirty minutes before Dean stops, allowing him to breath for just a second before going at it again.
Dean pushes against the skin of his sides viciously until Sam is breathless, teasing, "Poor wittle ticklish baby tickle tickle tickle tickle god you can't stand it."
Slowing down, he reached behind and began to walk his fingers up and down his brother's back gliding around the back shoulder blades, near the armpits so softly and slowly.
He grinned enjoying how goose bumps rose on Sammy's arms and how he shivered.
"Does your back tickle Sammy? Just a bit huh?"
Watching Sam as he tried to scrunch up helplessly he smirked teasing the back of his neck and back down making Sam squirm.
Then he just teasingly dragged one finger up and into his armpit and back down.
He dragged the finger relentlessly up and down his spine in various places, around his shoulder blades, near the armpits just scratching and back down circling slowly.
Whispering taunting, as he tortured, "Tickle tickle tickle Sammy cootchie cootchie cootchie coo tickle tickle tickle tickle."
Dean loved just keeping Sam on edge like this, tickling him so softly and teasingly, giving him a ghost of a touch for hours making him take it like this.
"Good boy Sammy such a good boy for me baby yeah I know it tickles just take it for me yeah tickle tickle tickle coochie coochie coo god I could do this to you all day."
Dean knew it was more than just the soft touch but the verbal teasing got Sam off.
Again he ghosted his fingers softly up and down Sammy's spine trying to find the most ticklish spot.
Eyeing Sam out of the corner he watched him squirm desperately trying to get away.
Laughing but ignoring Sam's weak attempt to escape his tickling touch he circled and drew soft lines up and down his back to his sides and back.
Smirking he taunted, "Oooooh there's the spot yeahhhh oooooh tickle tickle tickle Sammy I know it tickles baby let me hear you beg for it. Come on laugh and beg for me baby you know you want to. Cootchie cootchie coo tickle tickle tickle tickle tickle."
Dean laughed at his brother's helplessness, and let his hand slip and slide his nails teasing his bare skin.
He pinched the backbones teasingly, nails scratching behind his neck or ears making Sam giggle before digging into his side making his back arch.
Part of Dean wanted to flip him over onto all fours, and fuck the daylights out of him, get all up into his virgin butt, split him open, fill him with cum until he messes himself all up begging sobbing needing more.
On the other hand he could enjoy taking things excruciatingly slow drag it out and tease the laughter out of Sam until he begs to cum over and over.
Leaning in Dean taunted, "I wanna see you cum untouched."
Sam shudders hard his cock jerking as it hardens some more.
"I'm gonna touch everywhere but that sweet cock and you get all wet and hard for me and cum in your underwear so hard."
Dean shook his head as Sam begged already and said, "If you don't you can't cum at all today."
With that he presses his fingers into Sam's sides then delicately teases, watching his hips uselessly thrust upward suddenly at the sensation.
Reaching down he tickled Sammy's tummy as he slid those wet boxers down and dragged a single finger from the base of Sam's cock, letting it meander slowly up to the tip and back down again.
Hearing Sam moan he grinned and asked teasingly, "What do you want Sammy?"
Dean went back for another pass up his brother's stiffness, "Can you tell me?"
His gliding fingers demanded a response as he pulled sounds from Sammy's moaning throat by his mean and playful strokes.
The eldest did not let up questioning him over and over teasing him with his hands one on his cock, the other softly tickling his lower back and up, until he received an answer.
Dean slowly rubbed his hand up and down the length while teasing his side with very light excruciating tickles.
Tickling his belly for a moment he made his way up and around Sam's nipples until they hardened.
One finger began to trail the throbbing shaft so feather-light and ticklish making Sam moan and thrust weakly.
The finger traveled the length of him again before dropping back down again teasing his balls before stroking the thin, sensitive skin just behind his sac.
Sam's moans picked up intensity as Dean playfully ghosted his hand over his brother's shaft not tight enough to do anything more than add to his arousal.
Hearing Sam whimper he smirked whispering, "Ooooooh yeah you like that not gonna stop baby boy I could do this to ya all night and make you take it."
Dean's hand tightened for a moment around the shaft giving a one hard slow pull before gentling back into his slow taunting strokes.
Then suddenly Dean pulled away chuckling as Sam's hips lifted in attempt to gain further friction.
"Sam stop don't move." Dean laughed at him.
He used his hand to softly touch and tease Sam's vulnerable cock trailing a finger lightly up and down the length.
Very delicately he just ghosted his hand over the desperate flesh knowing there was nowhere near enough pressure to satisfy Sam.
"Dean! Please…"
"Hm? Please what, Sammy?"
Dean was careful to lean the bulk of his weight to the side of Sam's vulnerable sex, while making sure his jeans teased the hard flesh gently.
"Gonna make you beg for it Sammy."
Suddenly as Sam began humping the bed Dean smacked his ass.
Dean placed his hand over the pink spot rubbing it gently smirking, as Sam's cock grew even larger.
"Got a little kink there too Sammy?"
He stroked his cock firm and steady once, twice, and then pulled away with a grin.
First trailing a finger down the now throbbing erection between and over Sam's sac and balls, and then lightly oh so lightly teased a path to his hole before pulling away entirely.
Bringing his hand down on the other cheek he smacked it.
Dean began placing several smacks to the now pink ass in front of him, some hard and some barely hitting the skin.
Reaching down to his brother's heavy erection, he could tell he was close, as he ghosted his hand over the pulsing shaft teasingly.
Sam groaned as he pulled his hand up and just used his index finger trailing down the shaft and back up again.
He continued this slow agonizing teasing motion until Sam started trying to hump into it again, making Dean smack his ass again.
Dean gave a teasing flick of a nail over one nipple making Sam jerk and moan.
"Thwack thwack thwack!"
Smacking his brother's ass a few more times in succession he gently rubbed the bright red exposed cheeks.
Then again Dean reached between Sammy's thighs and teasingly stroked his cock, smiling at the helpless whine that was produced.
Watching Sam's weak attempt to hump again he smacked his ass and said, "No pleasure yet for you baby."
Lightly stroking and teasing his brother's tummy again for a moment wiggling and torturing, Dean had to grin at the feeling of Sam's upper body shaking against his hands from laughing so hard.
Dean dug his fingertips right above his knees into Sam's sensitive hips, pressing his thumbs into the softer parts on the back, boring his other fingers deep into the taut skin next to Sam's hipbone.
Sam tried to grab at his hands but he was firmly restrained, as Dean settled higher so his hands were nailed to the sheets, unable to defend his super ticklish sides, ribs, or underarms making Dean laugh at his helplessness.
Dean was scratching and teasing the bone right above the little spot under Sam's first rib nonstop with just one finger making Sam go crazy.
Then he scribbled his fingers over the little stretched skin under the ribcage.
The older brother started to let his hands walk under Sam's stomach, the fingertips circulating over the muscles.
"NOHOHOHOHOHAHAHAHAHA"
"Tickle tickle tickle Sammy cootchie cootchie coo."
Dean dug his hands under Sam's arms before lightening his stroke to just feather light teasing, wiggling his fingers as much as he could, before just stroking them.
"hahahahaha."
"Yeaaahh coochie coochie Sammy tickle tickle tickle."
All ten fingers of Dean's ran up and down his sides ever so slowly dragging it out, teasing him.
Smirking as Sam giggled lightly when Dean scratched between each individual rib.
Then Dean reached up and wiggled his finger so slowly up and down his chest further up until he tickled his neck.
He trailed his fingers right under Sammy's ears making the boy shiver.
"Like that Sammy? Yeah you love this cootchie cootchie coo tickle tickle tickle tickle tickle tickle."
Dean gave Sam a grin before unexpectedly reaching down and traced a finger so slowly up and down his vulnerable right foot, then the left.
"Nohohohohohoho!"
"Awwwww someone has ticklish footsies? Cootchie cootchie cootchie coo Sammy tickle tickle tickle does this tickle?"
Pulling Sam's legs into a headlock, he glided his fingertips up and down relentlessly slowly, teasing him.
Reaching in between Dean teased and stroked between the toes, rubbing back and forth.
Hearing Sammy moan and giggle he whispered tauntingly in his ear.
"What's the matter baby boy? Can't take this can ya? You're just so sensitive so ticklish aren't you? Yeaaahhh cootchie cootchie cootchie cootchie cootchie coo tickle tickle tickle Sammy."
"Man Sammy boy you remember that morning when dad had you pinned against his chest facing me, and he played with that cute little cock through your boxers all day and night making you cum over and over?"
Dean slowly dragged his index nail along the wiggling feet, lightly scratching his fingers along the base of his sweet baby brother's toes.
Slowing down he took a single finger and started slowly agonizingly trailing the tip of it down the smooth pink sole of Sammy's left foot.
Sam squeezed his eyes shut, throwing his head back and forth helplessly, and let loose with light giggles.
As his relentless finger continued to stroke, and tease up and down along the bottom of his wiggling foot, Sam laughed breathlessly.
Now Dean's finger slowly traced the edges of his feet, and every time he approached the ball of the foot he lingered for a moment, and used all four fingers and thumb to tickle the base of his toes.
Going back to the sole, now Dean scraped his nails along the tender flesh, watching Sam squirm trying to get away but Dean held him firmly.
Dean's left hand moved up to attack his helpless right foot watching the laughter explode from him again before slowing down again.
"Yeah baby you moaned and begged daddy for more and all I wanted was to tickle and tickle and tickle my sweet squirming baby brother in dad's lap make you laugh and beg some more, and spank that cute little ass."
Making his way back up to Sammy's upper body, Dean wiggled his finger just a tiny bit to tease Sam, not covering more than a fraction of an inch, and Sam jerked.
"Don't! Hahahahahaha plleeeaaassee I-I cccaaannn'ttttt hahahaha sssstttoooppp oh god hahahahahahaha!"
Now Dean's fingers were sliding around covering more and more ground, moving in slow lazy circles to get at all of his tummy.
Dean's sliding finger approached his belly button and slowly started to tickle all around the edges, and taunted, "Yeahhhh does this tickle Sammy? Tickle tickle tickle tickle my tickwish wittle baby."
He took his finger and inserted it into the smooth hollow there in the center of his beautifully muscled tummy, and wiggled it around with excruciating thoroughness.
"Come on baby take it for me just take it laugh for me baby let it out that's it cootchie cootchie cootchie cootchie cootchie cootchie coo."
Changing tactics, Dean teased the tips of his fingers from where Sam's right leg met his groin over and over dragging his fingers up and down never making contact, but again enough to arouse.
Dean made long slow lazy swipes up Sam's throbbing length just ghosting his fingers over his cock but not hard enough.
"Not allowed to cum yet baby boy take it for me."
Dean let his fingers envelop Sam's cock head making Sammy moan.
He rested his hands on Sammy's firm thighs and slowly made his way up Sammy's dick again feeling his trembling increase.
"You're not gonna let yourself cum as long as I'm touching you are you Sammy boy? You feeling so out of control of your body that you could have an orgasm while I'm touching you just like this?"
Dean let his fingers slowly trail up to the wet cockhead and tease over and over the sensitive area directly under his piss-slit and Sam jumped violently.
He formed his fingers into a loose fist and stroked slowly but expertly up and down Sam's shaft.
Every time he hand got to the cockhead he caressed the fleshy tip making Sam groan again.
"So tell me Sammy boy how close are you to shooting?"
"Ooooooooh gggoooodd sssoooo ccllllooosseee!"
The head of Sammy's cock was now very wet, covered with pre-cum and Dean went back to concentrating on it.
Dean slid his fingers up and down over the swollen red-purple flesh in a rhythm slow enough to create multiple sensations of sexual agony, as Sam squirmed madly.
Now he stepped up the pace of his teasing just a fraction.
One last time Dean teased around the twitching cock and unleashed the light tickling motion, dragging Sam to the edge and over.
"Good boy cum for me Sammy boy let it go you know you want to come on that's it!"
Sam unloaded in a series of violent spasms making grunting noises as Dean finally drew back allowing Sam to catch his breath and pass out.