Sam's Days of Sexual Pleasure

Dean and John had started torturing Sam with pleasure at the age of ten as they teased him with their fingers relentlessly fucking him, vibrators and dildos for hours a day with cock rings, and cock cages.

Then Dean had discovered something, and that was that Sam had a tickle fetish, he was turned on by being restrained and tickled agonizingly for hours.

So one morning Dean had a wicked idea for his little brother.

He woke Sam up in the bed by moving his hand that's draped over Sam up his brother's back making the shirt ride up and began dancing and ghosting his fingers lightly across his abdomen.

Back and forth he slowly dragged his fingers, and teased them slowly up Sam's chest and back down across his sides.

Hearing Sam moan he grinned up at his father as he pushed Sam's legs apart, and with teasing fingers slipped a cock cage on him, so no matter how aroused he became, he would not be able to orgasm until they gave him permission.

And it was about to be a very long few torturous days for Sam.

Lifting Sam's arm up slightly Dean could hear Sam waking more to their touches, as he slowly removed Sam's shirt and boxers, softly teasing with a stroking finger under Sam's armpit.

Sam moaned again and his eyes began flickering and Dean whispered in his ear with a grin, "Wake up little Sammy daddy and I've got a surprise for you. Come on Sammy."

Watching Sam's eyes open a bit he gently began tying Sam's wrists to the headboard, and his ankles outward so he was spread eagle on the bed.

Dean sits on the side of the bed and takes in the sight before him.

Once making sure the boy was thoroughly restrained that he couldn't get away, they admired the naked restrained young boy before them, so the thought that they were fully dressed made it further arousing.

John lightly began stroking the soles of Sam's ticklish feet.

Dean came around and slowly teasingly brushed Sam's ticklish neck at the same time.

Sam moaned and giggled slightly making both men grin at the young man's helplessness.

John wiggles all his fingers on Sam's feet slowly and agonizingly as Sam squirms trying to break away but there's no hope.

"Does this tickle Sammy?" Dean taunted.

All Sam could do was lay there and take it, laughing uncontrollably, and feeling himself getting hard at their soft touches.

"Oh Sammy Sammy Sammy." Dean comes to the side and lightly begins tickling both sides of his throat at the same time, dragging out the sensation, then down and back up his sides.

Sam can't help the huffing laughs that are being forced out of him.

He's so screwed.

His body has to struggle, has to try and get away and he alternates between jerking his legs up and down and then, as the panic escalates and the laughing threatens to bubble over completely, lifting his hips and straining right up off the chair.

Dean's fingers wiggle stroke and scratch softly all around his tummy, sides, and even his nipples beginning to grow hard, and it makes Sam a little crazy.

Sam's poor body is so confused.

Fighting his ropes is making it very clear that he's helplessly at his father and brother's mercy.

He doesn't want to have a hard on for being systematically taken apart by his big brother and father but there's not a damn thing he can do about it and God, that's only making him harder.

He thrashes and strains but the laughter is getting louder and his struggles weaker.

He's never seen Dean or his father looking so pleased.

"No! Stop! Dean! Naaghahahahaha!"

There's no way either of them are stopping because this is way too good.

Sam's laughter was barking, almost painful at first, but now it's coming easy and constant, rolling out like he can't stop, and he can't because they're not letting him.

Sam feels his smile, huge and dimpled.

His face is hot with exertion and John's looking at him as though he's a cute puppy.

John concentrates on one foot and then the other.

Sam pumps his hips with that big tent in his shorts and he knows it's lewd but he's not in control.

Sam can't take the torture anymore.

He keeps thinking this and it keeps coming anyway.

Dean has moved up to tickle over, around and behind his knees, up his thighs, above the line of his shorts, pausing to look pointedly between Sam's straining hard on and his face.

A spurt of precum escapes when he does this and Sam wildly hopes that Dean won't notice the wetness in the stupid heart patterned material.

Of course Dean remembers all Sam's ticklish spots from when they were kids and he pokes, wriggles and scrubs his fingertips in Sam's ribs making Sam howl.

And the panic is coming back now because the most ticklish place on Sam's body is under his arms.

Dean knows it and he's tormenting and taunting Sam, taking his time getting up there.

Sam struggles harder, trying so hard to pull his arms down against the ropes, pushing the rest of his body up as far as he can.

It's no use because there's very little room for movement and when Dean gets his fingers right into Sam's armpits Sam tries to scream but it just comes out as loud deep laughter, spilling right up from his belly, and he humps his body around as hard as he can to try and escape it.

There are tears in Sam's eyes and the two let him breathe.

Dean makes a few false starts towards Sam's armpits just to see Sam's body spasm and hear him beg.

The thrashing around has made Sam's hair all sweaty and Dean gently brushes the strands away from Sam's eyes.

Sam moves into the touch without meaning to and Dean's eyes flicker with interest.

John reaches out his index finger, stopping just short of touching the wet spot, leaving no doubt about what he's pointing to.

Sam's dick twitches up towards his hand.

"Tickling make you all horny baby boy? Tickling and kinky bondage and your big brother's and daddy's hands all over you?"

He feels all loose and sensitive from the tickling and he really really wants his father to touch his dick.

Sam at least wants to be able to keep still and quiet but he can't anymore.

He whimpers and rolls his hips, squirms and twists his head far to the side in shame.

The feeling of his boxer shorts being removed takes Sam completely by surprise.

He lifts his head to watch because this is different and John is crossing the line, just like that.

It's not only Sam's shame anymore if his father does this.

"Dad, what are you doing?"

His voice sounds deeper in his own ears, heavy with arousal.

John looks up, heavy lidded, eyes dark chewing on half of his bottom lip and Sam lets himself think, now, about wanting those lips wrapped around him.

"Want me to stop Sammy?" John keeps still, holding the elastic of the shorts but not touching otherwise. Sam allows his head to fall back his heart hammering at rabbit pace and dick throbbing so close to John's hands.

"No. Don't stop."

"S'what I thought." His shorts slide off and Sam anticipates a hand on his dick, prays for it, strains towards it, but Dean is back at the dressing table and Sam is completely exposed, ridiculous erection wagging around in the air.

Dean has a small red silky scarf, he ties it in a bow around the base of Sam's dick and Sam shivers at the feel of the soft material and groans at the humiliation.

Circling his little brother Dean smirked at his father and said, "Now if I remember correctly you have three main sweet spots."

Meanwhile lifting his hands up slightly to torment his brother.

John slowly raked his fingernails up and down his youngest son's inner thigh stimulating all the exposed nerves.

"Dean, please don't." Sam whimpered.

But Dean ignored his brother's protests as he lightly delicately teased his fingers up and down his brother's sides, and moved up to his lower ribs.

Sam lost it.

"Dean! N-no! Plehehehehehease!"

"Oh yeah, the lower ribs. Sweet spot number one." Giving an evil grin he continued to softly drag out that spot knowing slow torture turned him on.

"Deeheeheeheean! Don't! Stahahahahahahap!"

"What was that Sammy? Don't stop? Don't worry we weren't planning to at least for the rest of the day."

He slowly dragged his fingers up to his upper ribs before slowly reaching up into Sam's ticklish underarms, and stroking the hollows.

Sam gasped as Dean grinned.

"Not thehehehehere!" Sam begged.

He threw his head back slightly struggling less now as the tickling left him weak.

"Sweet spot number two!" Dean announced.

John meanwhile picked up a piece of string and slowly began teasing it between Sam's toes.

"Nohohohohoho! Deeheheheean! I-I c-can't t-take i-it! Hahahahahaha!"

Dean taunted, "Come on Sammy we're just getting warmed up here, you can take it, besides we've still got an entire few days of tickling and pleasure ahead planned for you."

"Now, where's sweet spot number three?"

He trailed his fingers back down Sam's ribs laughing at him as Sam shrieked and giggled insanely.

Dean was playing his ribs like a piano, with just enough pressure to make Sam go crazy.

He kept switching from his ribs to his underarms over and over again just to tease him.

Not remembering the spot without stopping his relentless torture he asked his father, "Where was spot number three?"

John replied, "I believe his spine and the back and sides of his neck."

Dean's fingers teased and stroked back up his chest, to his nipples, up to his neck as his fingers brushed softly at it.

They watched as Sam helplessly scrunched his shoulders up shaking his head from side to side.

Both men laughing at him and grinning at the torture presented on Sam's face.

Dean pointed to the table where there was a small paintbrush laying there, and his father reached over picking it up and handed it to him.

He watched as his eldest son dragged the bristles up and down Sam's sides torturously slow.

Then he began twirling it in Sam's bellybutton watching his reaction as he tried to hold in his laughter.

Their father grabs another brush and grabs Sam's left ankle in a headlock and slowly strokes his arch with the brush and feels his leg jerk as he tries to pull away.

"Sst-stop." Sam begged and pleaded.

John just shrugs and begins trailing over the tops of his feet as he squeaks.

He begins brushing over every ticklish nerve around his heels and toes.

"P-Please." Sam whimpered.

To both of them Sam was still begging and pleading, but they wanted to break him down to the least amount of syllables possible, so him talking now was unacceptable.

John moved to the ball of his foot and he jerks his leg again, a quiet gasp of ticklishness slipping.

Moving up to twirl the paintbrush beneath his toes, John smirked at his youngest, pulling them back and lightly dusting around each area making sure no skin is left untouched.

They hear him gasping and feel him tensing and just smile wickedly.

Swapping legs, John repeated the process on his right foot.

Dean meanwhile again begins to use his nails to spider over his ticklish underarms.

Seeing Sam's mouth twist he knows he won't be responsive any time soon, as his nails continue to spider relentlessly over his sensitive hollows.

His big brother began mocking his facial expressions as he dragged his wiggling fingers from his elbows, all the way down slowly to his hips, watching him try to twist and turn.

Smirking Dean continued to torture those soft underarms.

Then Dean changed tactics and moved to his neck, which caused Sam's head to jerk down.

He lightly brushed his fingertips over every inch of skin and behind his ears.

Sam's head jerks back in defense when he felt Dean's fingers on the back of his neck, as Dean lightly tickles just below the spot where he can't protect himself.

Dean's other hand brushes down Sam's ticklish throat and he jerks back forward.

Changing direction again, he worked his way up and down Sam's back finding a sensitive spot at the small of his back.

Sam squirms trying to fight the feeling of Dean's nails traveling slowly back up his spine to his neck, but feel them trailing down his chest.

He begins biting his lip as he watches Dean moving over his chest either a moan or giggle getting caught when he moves over his nipples.

Dean continues to tease him for a while there, and Sam tries to concentrate as he tries to keep quiet.

Picking up the brush again Dean twirled it over his right nipple, making Sam yelp.

He slowly trailed down to Sam's sides again tickling and digging into the curves to make him squirm.

He's clearly sensitive there but his hips are more attractive and they begin moving side to side he presses his fingers into them and rubs.

Sam's breath hitches as he tries to fight his body's need to move and assist the tickling torture, but he knows he can't resist.

Dean tells him this in his ear playfully licking the shell of it making Sam shiver, and squirm more.

Again he presses his fingers into his ribs and watches Sam squirm which only amplifies the tickling.

Then he takes the paintbrush and drags it across Sam's tummy back and forth agonizingly slowly.

His breath hitches again as Dean trails his waist but knowing it would be too easy there, he began trailing his abs instead.

He trailed down the middle of his abs to his navel and swirled inside the shallow part a bit.

Sam jerks back as the bristles toy with his nerves and Dean waits for him to crack, but this kid is stubborn.

John smiles and says "We knew your waist was ticklish so we figured we would move somewhere you're a little more sensitive."

Dean teases the paintbrush slowly across his waist and Sam jerks back.

Now he can only shake his hips side to side or thrust neither working to his advantage as they flutter below his happy trail.

Sam's lips quiver as Dean begins slowly painting from his chest to his hips and back down, repeating the short strokes up and down all the way across his waist.

John presses his lips below Sam's happy trail and blows, watching Sam yelp and jerk back.

Their father then reaches around his legs and runs his fingertips down the backs of his thighs, and hears Sam giggle.

He slid his fingers around the backs of his knees asking teasingly, "Ticklish here Sammy boy? Can't take it? You can take it a while more I think."

Snickering at his young boy's torture he moved between his legs and lightly scribbled his nails dangerously close to his crotch, knowing Sam could not orgasm for hours yet because of the cock cage.

Picking up the brush and drags the bristles over sensitive skin making Sam yelp and giggle, but then John begins moving to his weak spot.

John lets his fingers rest against the backs of Sam's knees, which are now coated in a thin sheen of sweat.

He squeezes the pressure points above his kneecaps to make his son yelp but he stops before he can laugh.

Dean taunts in his ear whispering, "Are you ready for this to end?"

Watching Sam nod eagerly Dean continues softly, "Then all you have to do is laugh" as he begins gliding his fingertips up and down his sides, and hips, across his tummy and down his thighs and settling on the backs of his knees, where they speed into a torturous dance over his sensitive skin.

Sam yelps as his head falls back and thunderous laughter shakes his exhausted body.

John moves a hand to his thigh and continues to softly tickle him there, moving his lips to blow a raspberry against his untouched knee.

A shriek shoots out of Sam as he laughs and pulls at the restraints. They begin blowing and blowing again until they finally stopped and Sam becomes silent.

Taking a slight break they allowed Sam a little water before Dean continued on with the next part, which would be more sexual than just tickle torture, maybe play with the cock cage a bit to tease Sam.

Coming back over to Sam, Dean has a riding crop in his hand, as John is on the sidelines watching.

The big brother grins at his brother's helpless exhausted body and lets the crop trail down his brother's body until he can gently tap against the cock cage.

Squatting down Dean cups Sam's balls rolling them playfully in his hand, making Sam hiss.

Dean remarks, "You're really full while we're at it I might as well milk you now considering we've been going for a while, and we are going to make you orgasm repeatedly non stop all day for another few days and there's nothing you can do about it."

Sam's whole body tenses on the bed when he feels Dean lean behind him slightly, and feels a cold, wet finger press against his hole, teasing the muscle.

He feels the whole finger inside of him, gently moving around.

Dean makes an approving sound and Sam is sure his face must be a beet red by now, but there's nothing he can do about it.

A second finger soon joins the first and feels Dean scissoring inside of him.

It lasts only several seconds until Dean hits his sweet spot inside of him that makes Sam see stars and lets an involuntary moan escape him.

"Like that huh? Just take it for me Sammy." Dean teased softly and starts rubbing his prostate relentlessly quickly reducing Sam to a whimpering shaking mess.

Dean grinned at the thought of power he had over Sam's naked body right now because his little brother was tied to the bed helpless, so all he could do was lie there and take it.

Sam looks down between his legs in time to see the first drop of milky white cum falling from his still bound cock.

He turns away and tries to ignore the waves of pleasure running through him.

Dean does not stop until his balls are nearly empty and Sam barely manages to stay put.

He hisses when Dean adds a third finger and teases, "You are doing so well Sammy, almost can't believe you're a virgin, you open up so nicely for me. I bet that annoying pressure in your balls is gone now."

His big brother continues to relentlessly tease and fuck him with his fingers, though Dean avoids touching his prostate, which drives him crazy.

Grabbing a brush while relentlessly teasing his little brother with his fingers in his ass, he reaches forward with the other hand and tickles Sam's balls knowing they are so full that it hurts Sam.

He just keeps stroking though ignoring Sam's pain or pleasure and reaches down with his hand to cup them in his palm and roll them again.

Dean remembered a night when Sam had the cock cage on and vibrating plug in his ass as they were all sitting watching TV with their dad on the couch with Sam in the center leaning back against Dean's chest.

And Dean and John would spend hours just softly tickle torturing him in different positions knowing he couldn't get away.

Then one would wrap one hand around the cock cage holding it still while ordering him to spread his legs wider, and one of them would pull and push the plug in and out of Sam.

They would test the remote control on different levels bringing Sam to the edge many times, but not enough to let him orgasm.

They would then playfully push two fingers in and Sam would let his head fall back resting on Dean's shoulder.

One of them would play with him for close to an hour just gently fucking him with their fingers relentlessly.

Dean thought maybe today they could do that to him again, he felt like Sam could take it, so he would bring up the idea to his father once they were done here.

Feeling Sam desperately trying to fuck himself back on his fingers he continues to tease his prostate slowly and his moans are like music to Dean's ears.

Keeping an eye on the strips of cum from Sam's soft cock he tries to coax even the last drops out of them.

Stopping for a moment, Dean leans in and says, "We will limit you to orgasms as we say today and tonight and I can't promise I won't tease and edge you for a few hours before each one."

Sam lets out a sob as Dean slowly pulls the cock cage off his cock and torments, "Don't worry, Sammy, I'll make you feel so good. Look at that, barely out and you're already almost completely hard. Someone seems to be really desperate, huh?"

Dean kneels between his brother's legs watching him squirm, and Dean isn't sure if he tries to get closer to him or away, and he smirks.

There are tears on Sam's cheeks and Dean gently traces the length of his cock with his fingertips.

"You really want to cum, don't you? Say it." Dean teases.

Sam looks at him with pleading eyes and he sounds like he's begging.

"I want to cum. Please, Dean. Need."

Dean continues to play with him just like this stroking his cock slowly up and down, and normally Dean preferred to play with his baby brother for quite a while more, to make him break down to monosyllables but not now.

So he just wraps his hands around Sam's dick, using the precum collected at the tip to properly jack him off.

As expected, it doesn't last long.

Sam is a moaning mess in seconds, and when Dean reaches up to give one of his nipples a gentle tug he's gone.

Dean removes the cock cage as Sam begins shooting his load all over Dean's hand and his own chest.

Dean laughs at him through his orgasm, enjoying the sight of a heavily breathing but completely blissed out Sammy.

When he's done, Dean cleans him off.