Sammy Teased In the Impala
As they raced down the road headed to their next hunt Dean glanced over at Sammy with an evil smirk.
About an hour before he teased and tickled his little brother without mercy, bringing him to the edge without climax.
Sam internally was actually thrilled at the thought of being at his brother's complete mercy.
Dean grinned mischievously as he slipped behind the wheel, seeing Sammy's baggy jeans tenting.
Reaching over he asked playfully, "How you doin here Sammy boy? Don't tell me you're beggin already."
Watching as Sam's cock deflated for a moment, he reached over glancing evilly at Sam and passed a hand over his jeans rubbing at Sam's sensitive cock causing it to swell up again.
Getting ready just an hour before he told him he was not to wear underwear for the long drive, just the jeans until they got in the car.
So when Dean began teasing Sam's cock to inflate it again before starting the car, he had unbuttoned Sammy's jeans, pulling them down to his ankles telling him he was to remain like that the whole drive.
He also pulled Sammy's shirt up so he could tease and tickle his chest.
On the road Dean leaned over whispering to Sammy " I want you to touch yourself."
Glancing over slightly he watched as Sam touched his hand to his tummy, watching Dean watch him.
Dean hardened at the sight of his younger brother looking for his approval.
He smiled at Sam's continuous innocent touches.
Dean began with one hand with the other hand on the wheel moving it around his little brother's cock beginning to stroke him.
"Dean?" Sam questioned.
"Keep touching yourself." Dean commanded to Sam.
"Tell me how it feels to have my hand around your cock."
Sam's hands were now clenching the sides tightly as he murmured weakly, "G-good. Dee p-please."
"Tell me more." Dean continued.
"God…. Dee… So close… P-please…" Sam begged.
Sam tried to clench his legs together to protect his sensitive cock as he tried to hump the hand around his penis, but then the hand stopped.
"No, today for the next few hours you are going to keep your legs wide open for me. So I get to do whatever I want to you and you get to just take it."
Sam re-opened his legs and Dean rewarded him by lightly cupping his balls, sliding a finger between the two pieces of flesh, and softly tugging one and then the other.
Very slowly Dean began to pump his shaft teasing watching with a smirk as Sam threw his head back against the rest moaning helplessly.
Hearing Sam begging him weakly not to tease, Dean loving Sam's responsiveness to his touch taunted, "What are you gonna do about it huh with your pants pulled down around your ankles your legs wide open for me? Can't do anything but lay there and take it baby boy."
Dean just slid a hand over Sam's tummy gently tickling it in circles.
He watches as Sam moans helplessly trying to press up against the touch, and is cock hardening against his stomach leaking pre-cum, before Dean pulls away.
Lightly he touches the underside of Sam's cock making him hiss before he pulls away again.
He then slides his hand up and down Sam's ticklish side, and let a cold finger brush Sammy's nipple on the side closest to him, teasing it toying with it to make it hard.
Torturously slow, he presses a finger with his free hand to the spot just above Sam's dick close enough to feel the heat pouring off of it.
Dean grins as Sam bites his lip hard trying to force himself to look away while Dean plays with him.
He traces a path up his little brother's torso with that finger tickling him lightly along his side mercilessly.
Whisper soft he runs his fingers down the rigid length of Sam's cock pausing to cup the heavy weight of his sac before slipping further back.
Dean rubs his fingers against the slit of Sam's dick over and over, teasing it upward along his squirming side back to his nipple.
He pinched it lightly and then a bit harder, then soothing him by lightly tickling his chest, watching him shudder.
Tracing excruciatingly soft light circles around that nipple for a while he watched Sam shiver and shake sensitively as it tickled, and he heard Sam groan, making him grin.
For a moment he decided he just wanted to make Sam laugh, so he glanced quickly back at the road, while the other hand dug their fingers lightly into his side, wiggling them in a merciless tickle.
Sam squirmed desperately as he grew hard even more as he felt Dean's fingers scribbling up and down his side without mercy as he began twisting and squirming forced to take it as long as Dean chose to make him.
Dean lightly began squeezing Sam's hipbone and then he trailed a finger up Sam's side and ribs ever so slowly and stopped just below his armpit.
He then just hovered his wiggling finger above Sam's underarm threateningly.
By this time Sam was squirming and desperately trying to escape, but knowing there was no way out.
Dean teased and taunted, "Poor Sammy so ticklish and nowhere to go, can't get away completely at my mercy."
Moving his hands down he relentlessly softly started tickling the back of Sam's leg, squeezing the sides he lightly spider like crawled his fingers along the back and squeezed all around them.
He lightly gave a tickle and a stroke on the insides of Sammy's thigh just dragging his fingers up and down relentlessly smirking at Sam's helplessness.
Taking his fingers he lightly let them flutter into the curls on either side of Sam's oversensitive dick moving back and forth inside and outside of his inner thigh area to either side of his balls.
His fingers played around Sam's hipbone that was closest to him and again tickling the tops of his muscular thighs.
Lightly and delicately Dean scrubbed playfully Sam's torso again up to his nipples in a slow back and forth motion.
He alternated rapid spider crawling strokes with light, shallow jabs quickly moving squeezes and scampering, skittering taps with his dragging fingers.
Slowly he again worked up and down the insides of his thigh, paying close attention to his desperately leaking cock that was now like a deep red color almost purple.
Dean began to slow his tickling to a more erotic, leisurely pace for the continued drive.
Sam's laughter soon alternated to moans of lust and pleasure.
In response Dean began to brush his hand slowly across Sam's stiffened dick.
His body jolted weakly as he tried to take the stimulation, too aroused to speak, as he just continued to writhe, and thrash and squirm and moan, then giggle and gasp.
As Dean moved his hand faster across Sam's dick, Sam began to almost hyperventilate.
Reaching across a bit more he took the opportunity to circle his wiggling fingers around his tender belly, feeling it twitch and tense at his slightest touch.
Sam gasped with ticklish pleasure each time Dean stroked and tickled his heaving tummy.
Dean stiffened the index finger of his hand and slowly continued as he started tickling all around the edges of Sam's belly button and Sam panted with uncontrollable laughter.
Trailing his hand down his fingers began lightly tickling Sam's balls as Sam shuddered and groaned.
Leaning in Dean taunted, "You're real horny now aren't you Sammy boy? I know you want to cum so badly it hurts but guess what? I'm gonna tease the hell out of you before I ever allow you to cum just take it Sammy."
After an hour of stroking, teasing and tickling his balls Sam was crying and trying to beg to let him cum, but Dean ignored his pleas, dragging it out to calm Sam before beginning again.
The entire time while physically torturing the boy, he kept up a running commentary about the state of Sammy's helplessness and horniness.
Continuing to whisper dirty words in Sam's ear about what he was gonna do to him as he got him into their next motel room, he began to jack Sam off still teasing a little, before he once again backed off, making Sam thrust in the air desperately.
Dean continued slowly stroking his cock up and down hearing Sam whimper he ignored it and went on.
He purposefully took slow strokes up and down his cum covered shaft thrashing as much as he could in the car desperate.
Sam just grunted and tried to squirm free, as Dean stroked him ever so slowly.
Once in a while Dean would use his thumb and run it around his cockhead driving Sam crazy.
About an hour later Sam was begging to cum, noticing his heavier breathing and his clenched fists, Dean slowed to a stop for a moment.
"Oh I'm sorry Sammy boy were you gonna cum?" Dean teased softly.
He wrapped his cum covered hand around Sam's still hard dick and continued teasing and stroking his cock.
Sam moaned helplessly again and Dean noticed he was close again so as he continued stroking him, he slowed down even more.
Sam's body started to bounce a little and Dean warned him to stop, watching Sam's body tense and his fists clench again, Dean stopped.
Hearing Sam's angry grunt Dean said, "I will let you cum when I want you to you understand? Your dick is mine for the entire ride, just relax."
Again he started to slowly stroke his cock watching him bounce up and down.
Noticing Sam was trying to speed things up by fucking his hand he grabbed the base of his cock and continued teasing gripping it harder, taking very slow agonizing strokes up and down his quivering shaft.
Now that he was holding the base of his cock he could not bounce anymore which drove Sam crazy.
Sam continued to thrust and moan.
Dean knew he was close again but since he was stroking him off so slowly it would be a while before he would shoot.
After about twenty minutes Sam began to tense up again, wanting that urge to build up keep him there at the edge he continued pumping his cock slowly backing off until he stopped again.
He continued to work Sam's bouncing cock for another solid hour while focusing on the road.
Dean took slow strokes from the base to his cockhead relentlessly
as Sam sat there motionless and grunting every so often, making Dean smirk.
As he continued teasing that cock he looked over at Sam's face from time to time is eyes squeezing shut trying to block it out and Dean grinned wickedly.
Working his cockhead for about another ten minutes he went back to slow strokes up and down his hard shaft, noticing he was close to cumming again because his fists were clenched, he slowed down even more.
Sam's tummy hardened as Dean continued teasing and pumping his cock, he stroked him for about another five minutes before stopping at the edge again.
Then suddenly Dean changed it up again as he ran his hand up and down Sam's ticklish side again slowly making Sam go from moaning to laughing.
Again he alternated his motions as he began playing with Sam's hard cock.
He began again slowly stroking Sam's cock up and down from the base to the cockhead.
Then dragging his cum covered hand upward tickling his side for a moment, he made his way to Sam's nipple circling it, before running his hand slowly up and down his squirming side again.
Sam started bouncing up and down helplessly in the car seat trying to get away from Dean's wiggling fingers unsuccessfully.
This time Dean made his way down and took very long slow agonizing strokes up and down the shaft.
Hearing Sam moan, Dean teased, "Good boy Sammy, I'm gonna keep pumping your cock just like this until you cum. It may seem like torture but it's pleasure for me watching you shiver and shake and moan as I stroke you off slowly. You will eventually cum but it will just take a while and we have a good few hours, lay back and take it."
He then began massaging and tickling the cockhead firmly holding the base and fondling the head with his fingers, stroking him off again.
Sam moaned his eyes fluttering shot as Dean murmured dark with lust, "God you look so hot right now Sammy your cock is so hard and firm, looks like it is ready to explode, you probably want me to speed it up a little huh?"
Watching Sam nod Dean answered playfully taunting, "Well, I like to take things very slow, I want to keep you on this sexual high for a long time. Or at least until I let you cum which will not be for another good few hours."
Dean chuckled when Sam moaned at his words.
"Want me to stop Sammy?"
Sam was weak and tired as Dean said, "Well all you gotta do is cum."
Knowing he could not though was sexual torture for Sam but pleasurable teasing for Dean.
Dean just kept stroking his dick up and down each time slowing down more until he again pulled off, making Sam grunt in frustration, and Dean just laughed.
Once again he started by taking long slow strokes up and down the hard shaft teasingly.
He warned Sam to try not to move and to just take it or he would make the torture longer, and just stroke his cock all day and night whenever he had the opportunity.
Slowly dragging his fingers up to Sam's side again he slowly tickled it and up around to his chest and played with his nipple.
Noticing that Sam was on the edge again he backed off again, waiting until he got soft and then again began jacking him off slowly telling him he would let him cum in an hour or so.
Dean kept him on the brink of cumming for that hour, telling him to relax and take it how hot he looked all desperate and begging, unable to go anywhere, just lie there in the seat and take it.
Sam started moaning again reaching the edge, and Dean stopped again, watching the torment on Sammy's face.
Reaching around he teased Sam's nipple again and tickled his way back down to his cock jacking him off again slowly.
He took long slow strokes from the base of his cock to the head over and over smirking at Sammy's face.
Sam moaned and begged thrusting his hips weakly into the air desperate for friction as Dean kept him on the edge once again working him slowly.
It had been at least a good three hours now that Dean teased, tickled, tortured, and taunted his sweet baby brother, keeping him on the edge sobbing, begging to cum only to be denied.
Dean began focusing on the cock head with his fingers he traced Sam's cock all around and then he started rubbing the tip of it over and over so slowly.
He gripped Sam's dick firmly starting to jerk up and down as more cum oozed out.
Sam began panting desperately and Dean looked over whispering as he continued with one hand, "You're doin fine Sammy boy, just stay still while I work your cock. Remember, don't cum until I say you can."
Dean's fist just kept riding up his cock and down from the base to the cock head relentlessly.
Knowing Sam was on the edge again he backed off but lightly brought his hand up to tickle torture Sammy's lower tummy close to his cock to tease the boy.
Then once again he began stroking him this time his fist was a little tighter than before, making Sam desperate and Dean stopped.
Sam panted, "Please let me cum."
"Not yet. Just relax, I'll let you cum eventually get ready baby boy, I'm gonna start again."
Dean started stroking again and Sam closed his eyes in pleasure, once again brought to the edge only for Dean to stop again.
Sam begged weakly, "Please."
Shaking his head Dean responded, "Not yet baby I'll tell you when just be a good boy for me and take it."
He started stroking him again slowly, then up to tickle his lower tummy and back down.
This time when he continued his fist was very tight rubbing up and down his cock but this time even slower than before.
Dean ignored Sam as his talented hand just continued to torturously slowly glide up and down his hard dick.
"Lie still and relax. You're gonna be here for quite a while longer, and when we get to the next motel, I'll tease you and tease you until you're a sobbing mess."
Tickling the boy's left thigh the one closer to him he taunted as Sam sobbed with need, "Poor horny boy can't take it can you? God so hot all open and exposed to me like this forced to take it, yeah I know feels good doesn't it baby boy?"
He ran his index finger of his right hand down Sammy's ticklish side from his rib to where the elastic of his underwear normally hugged his hips.
Sammy jumped shrieking slightly making Dean smile in amusement.
Dean taunted and teased wiggling his fingers mercilessly against the tender flesh at his side knowing he could not escape because the seatbelt kept him in place.
He slowed down a bit just lightly stroking his fingertips up and down Sam's squirming side.
Trailing his fingers upward ever so slowly he made his way up to the side of Sammy's neck, around to the back, and very slowly down his spine, softly tickling the lower back.
Sam grunted as he squirmed and arched his back slightly.
Bringing his hand all the way back around Sam's side, tickling it on the way down back to his inner thigh he grazed his thumbnail along the boy's tender, swollen scrotum.
Dean started running his finger around in torturous circles right under his balls for a while.
His right forefinger was moving relentlessly up and down his shaft excruciatingly slow, then up to tickle his tummy.
Making his way up and around again he began touching his upper and lower back with slow running fingers back and forth, up and down as Sam gasped and arched his back.
"Hahahahahaha p-p-ppleaaasseee sssttooppp."
Sam begged as he felt Dean's fingers lightly tickling the backs of his shoulders, down to his upper back and following down to his lower back.
Then he moved around back gently running his fingers up Sam's rib to his armpit, watching him squirm.
Gliding his hand back down he let his fingers softly scurry along Sam's side for a few agonizing minutes.
Dean taunted him as Sam gasped for breath, as he could not do anything to stop it.
"Tickle tickle tickle! Who is the ticklish little boy hhhmm? Kootchie kootchie koo."
Feeling Sam shiver at his touch he dragged his hand around back and softly tickled up his back lightly around the shoulder blades, and back down dragging out the sensation, watching him take it.
Dean's hand started to slowly trail upwards to Sammy's neck.
"Hahahaahahahahaha ssstttooopppp."
Sam cried, begged and pleaded but Dean was relentless.
He slid his hand down Sammy's chest lightly circling and tickling his nipples down to his tummy tracing wide agonizing circles with light wiggling fingers.
Then letting his hand glide up he tickled from his tummy up his chest torturing those poor nipples until they were hard pinching them lightly and back down over and over.
For about another hour, he tickled his nipples excruciatingly lightly so Sam would be unable to take it, and teased a finger over Sam's side in light circles over and over just very agonizingly slowly, smirking as Sam moaned and whined.
Recognizing that they would be approaching the motel shortly, he slid his hand back down lightly tickling between his thighs beginning to lightly tease the swollen head of Sam's cock with his fingers.
Knowing Sam could not control his body right now, Dean glanced over whispering,
"Oh yeah baby boy look at you all hot and desperate, moaning and begging for me, don't even think about cumming until I give you permission. You will be spanked and teased at the motel as punishment if you don't listen."
Dean made a very loose fist on Sam's cock and began to stroke its full length from the thick base to the tip of his leaking cock.
As his hand descended back to the base, it would brush up against his sac and he watched Sam out of the corner of his eye as he jerked and begged, making that same motion again.
He leisurely continued teasing and stroking Sam's cock, eventually speeding up the motion slightly as Sam's cock continued to grow.
Sam's body tensed and he bit his lip.
"Oooooh ggoooood."
Sam moaned and begged to let him cum.
Dean slowed down and stopped stroking watching as the boy began fucking the air gaining no relief.
Sensing Sam's sexual distress, he slowly massaged his chest tickling his nipples and tummy slowly.
Grasping his cock again he began to play with the head.
He would purposely brush his hand against the ball sac over and over hearing Sam protest and moan.
As he sensed he was getting closer to cumming he sped up again.
"Ready to cum Sammy?" Dean taunted.
"Yyyeeess pppllleeaassee."
When he felt Sam begin slowly fucking his hand he stopped again making Sam almost scream.
Dean began teasing his cock again Sam softly begged, "Please let me cum."
The more Sam begged and sobbed the slower Dean stroked him.
Bringing his hand up he watched Sam out of the corner of his eye as he tortured his nipples, circling one and then to the other just pinching them playfully.
Approaching the motel Dean thought about it and decided he wanted to get Sam off by tickling him to orgasm.
Continuing the nipple teasing for a few minutes, he pulled into the parking lot.
Unbuckling slightly, Dean leaned in toward Sam now having both hands accessible he twisted and pinched the boy's nipples back and forth tauntingly.
Dean slid his fingers on Sammy's flat tummy and abs, gently at first circling closer and closer to his belly button.
He began to tickle Sammy's tummy with both hands moving to his sides, continuing slowly with both hands lightly fingering Sam's abs and bellybutton and lower sides.
Reaching he slid his hand under Sam's shirt that was slightly lifted up from the drive, and began scraping and teasing his upper and lower back with slow agonizing running fingers, back and forth, up and down.
Whispering darkly, "Tickle tickle tickle Sammy. You wanna cum Sammy? You're gonna cum for me Sammy, come on I know you want to tickle tickle tickle."
He watched as Sam gasped and arched his back trying to get away but Dean was relentless knowing Sam also got off on being tickled.
So he did not let up as he ever so lightly tickled Sam's shoulders and behind, down his upper back and down to his lower back excruciatingly slow with one finger.
Dean brought his finger up and down the middle of his brother's back knowing he couldn't take that, until he just barely approached the crack of his ass and just teased a finger there before sliding up again.
Continuing to lightly tickle Sammy everywhere on his exposed trapped body, Sam began panting out of breath as Dean continued taunting in his ear, "Come on Sammy cum for me come on let me see it."
That was it for Sam as he cried his way to orgasm as cum exploded from his balls about twelve times as Dean worked him through it.
One last time he slowly tickled Sam up and down his sides, before letting go, allowing him to unbuckle and step out, smirking as Sam remained unbalanced.
Grabbing their stuff from the car Dean walked with him while lightly tickling his upper back again he said, "Oh just think of the night ahead Sammy, maybe a bit of spanking for you, tying you to the bed, edging you over and over, tickling you, make you sob and beg for me for hours."
At that Sam moaned making Dean grin wickedly preparing for another few hours of torture on Sammy.