Pain Snippet: Torture most Pleasant
One shot, 1 hour speedwriting experiment. 
(Start: 1:00am)

Greg was in hell… or was it heaven?  

The young wolf, a 24-year old college wrestler, had certainly written a hell of a check with his big yap that his body was now paying for dearly.  His captor, Drake, a 19-year-old freshman, had bet him 24 hours of servitude that he could beat the burly jock to a fall.  If Greg had won, the mouthy youngster would have quit the wrestling team for good, but in just under 12 seconds, even with Greg starting from the dominant position, Drake had him shoulders down on the mat.  So Greg had called his roommates, told them he wouldn’t be home until the next evening (Saturday), and had driven the younger Dragon to his apartment.  

Greg had sworn, on video, that he would not ‘punk out’ and that he would do anything Drake said, no matter how degrading, as long as it wouldn’t get him in legal trouble, a small concession Drake had agreed to for the sake of team harmony.  Greg had not, however, expected what Drake told him to do first. 
“Strip naked, right now.”
The wolf’s jaw had about hit the floor, but he had showered in the lockers since high school, so he did, without hesitation.  Drake collected his clothes, and put them safely away, then marched Greg into the bathroom.  
“Shower, and get yourself as clean as possible.  Do it with the curtains open.  I’ll be watching.  Like I have been since practice started.”  
Greg was flabbergasted, but he didn’t argue.  He tried not to look at Drake as he showered, but the masculine scent coming from the younger male was pretty damn strong, and as Greg looked, he saw Drake caressing his dick, a thick, deep red thing with a heavy pair of matching balls under the 8 inch rod.  He wasn’t straight up jerking it, though, and Greg had ideas as to why.  Ideas which, to his chagrin, made his own knotted tool slip free of his sheath, not quite as long or thick overall as Drake’s, but more than average for his species.  Drake had a slick smile on his face, the green dragon watching his teammate showering, both of them hard as rocks, and knowing that something was going to happen soon, one way or another.  Drake surprised Greg with his speed and stealth, as Greg was trying to turn the water off, the younger male stepped up behind him and roughly grabbed a strong, scaly pawful of wolf nuts, causing the bigger male to yelp in surprise.  

“I bet you’ve bred a lot of bitches with these big, furry nuts, haven’t you Greg?”  Drake squeezed his hand around the orbs in his grasp, causing Greg to pant and clench his fists in a mix of anxious fear and anticipation.  “I’m sure you’ve also had your fair share of nut shots, it happens in wrestling.  So all I want to know Greg… is are you ticklish?”

“Uh…” Greg started, slightly thrown.  “K-kinda, yeah, not very easy to tickle me though, fur’s pretty thick…”

“We’ll see about that.”  Drake let his hand go, seemingly to let the wolf be for the moment… but then he brought his open palm back quickly, and slapped the older male in the gonads, hard enough to send him to his knees, coughing and gasping in sudden crippling anguish.  “Once you’re done down there, put your singlet back on, and come to the bedroom.  Make it quick.”  Drake left the wolf in the shower chamber on his knees, one hand clutching his lightly throbbing nuts, and the other a fist on the floor in front of him.  
He wished like hell that would have been the worst of it.  

After dressing and heading to the bedroom, his boner very visible and prominent in the belly of his singlet, he was gagged and handcuffed, behind his back, and laid on a pallet of pillows and towels.  Then his feet were strapped into a stockade of sorts, and strung to the ceiling, leaving his feet hovering in mid-air, roughly eye level with Drake, and the majority of his body utterly exposed and helpless.  Greg would never openly admit it, but just being in such a situation turned him on immensely.  The younger dragon still being rock hard and butt naked helped too.  

Drake said nothing, merely rubbing Greg’s feet at first, a not at all unpleasant sensation, and followed this with rubbing the top of his foot against Greg’s twitching hardon through the singlet.  Drake had procured a stool somewhere and was sitting on it now, and was now teasing the wolf at his leisure.  The tease, however, soon turned into the most heinous torture Greg could have imagined.  First, the dragon had brought his foot up, and stomped roughly on Greg’s defenseless balls, causing him to groan piteously, but immediately after, he started tracing soft, slow lines over Greg’s footpads with his claws… which tickled like MAD.  So, despite the pain in his nuts, Greg laughed and giggled like a child, continuing to giggle and squirm as Drake went back to rubbing his dick with his foot, all the while the tickling continuing without mercy or relent. 

Greg lost track of how long Drake held him in this helpless position, tickling him nonstop, and doing everything imaginable to cause his helpless nuts great pain; squeezing with his toes, stomping, kicking, ramming them with his knee, slapping them, and even delivering a surprise punch not once, but twice, both of which made Greg want to puke… but through it all, Greg stayed hard as tree bark.  Now, after an undeterminable time of suffering like he had, he was close, oh so close, to his blissful release, a fact that didn’t escape his captor.  Drake sped up the rubbing of his foot, focusing on rubbing more firmly against Greg’s tender knot, and as Greg moaned and squirmed hardest yet, the wolf released a few thick, heady spurts of jizz into his singlet and all over his belly.  
Then Drake stomped on his balls again, causing him to yelp and bellow into his gag, and renewed his force of tickling the wolf’s sensitive feet. 
“What, you expected me to stop just because you came like the pervert you are?  You’ve still got twenty-three and a half hours of being my slave, wolf boy.  Don’t expect a single one of them to be spent sleeping.”
Greg started to panic, trying like hell to free himself for a moment, but stilling when Drake reached down and grabbed his slowly deflating knot, and spoke very sternly. 
“You gave your word, Greg.  You said you wouldn’t punk.  You lost fair and square, and you’re gonna take your punishment like a man…” He moved his grip to Greg’s aching nuts, and squeezed them hard enough to steal Greg’s breath and make him see white for a moment.  “… or you won’t be much of one anymore. Capisce?”  Greg could only nod as tears rolled down his face; the pain was getting to be too much to bear.  He wanted nothing more than to curl up around his aching nuts, shield them from the damage they were receiving, hold them and stroke them, put a glacier on them to ease the pain, something, ANYTHING!  This wasn’t just pain, this was the most pain he’d ever been in, worse than the broken collarbone, worse than whooping cough… his balls were made of lightning and fire, and every nudge or bump they took ached like dying… but Drake kept right on stomping and kicking them, which made Greg want to die. 
To top all this off, Greg couldn’t contain his laughter from the tickling.  It was hell.  It tickled worse than feathers and Drake simply would *not* stop.  A fit of giggling and moaning in horrid pain, and for a long time (longer feeling for the jock in bondage anyway) it was relentless… then finally the tickling subsided, the foot moved away, and his feet were lowered to the floor.  

“Before you get the idea that I’m simply done with you, Greg, know this: My record for orgasms in 24 hours is currently 9, with my previous girlfriend.  I plan to break that record, and every last one will be going in your tight little ass.  Starting with the big one I’ve been working on since we got home…”  He moved and pulled Greg’s singlet down off his shoulders, over his body, and down around his bound ankles.  A cold, moist finger fought its way under Greg’s tail, but when the clawed fingertip softly started massaging Greg’s prostate, he moaned whorishly and couldn’t find any more strength to fight. 

What came up under his tail next was MUCH bigger than a finger.  It tapered though, a small mercy, and without much trouble, Drake was fucking away merrily at the helpless wolf.  Greg would, again, never admit it, but he had always wanted to feel the heat and pressure of another real man in his tailhole, and now that he was here, bound, helpless, and being fucked silly by this new kid, he had to silently admit to himself that he was enjoying it, pain and pleasure both.  Just the knowledge of this spurred new life into his hidden shaft, and within a few moments, his slick, red cock had pushed all the way back out into the open air again, knot slowly inflating.  

No sooner had his cock gotten hard again than was it grabbed by Drake, and squeezed again, making Greg whimper, but do nothing more.  

“So, you’re enjoying yourself now, huh?”  Greg simply nodded a little, his ears pressed back tight against his head as Drake spoke.  “Good, then I had you pegged right.”  Drake buried himself to the hilt in Greg’s ass, eliciting a low groan, and moved his hand from the wolf’s dick to his muzzle… which he removed the gag from.  “So you let me beat you, didn’t you?  You were curious as to what I’d do right?”

“Y-…yeah.”  Greg said softly.

“You even liked me abusing your fucking balls didn’t you, you perverted bitch?”  This brought Drake’s hand slapping down from Greg’s muzzle to his crotch, the hardest slap Greg’s nuts had received that night, and Greg whined and cringed and whimpered for a few moments, more so as Drake’s hand grabbed his balls again and squeezed. 

“Oh OH GOD YES!”  Greg answered half in pained panic, half in lustful desire at the fire roiling in his swollen nuts from the latest abuse.  “OH FUCK, MY *BALLS*!” Greg was once more in hell, but he felt another mind-blowing orgasm coming on soon. 

“Good!”  Drake said with a smile, letting Greg’s balls go, and starting to stroke him off, going back to fucking him as well, the tapered point of his dragon cock thumping Greg’s prostate on every stroke inward, and driving them both toward the climax quicker.  “Then after this… I’ll just tie you to my bed… naked and helpless… beat on your sexy fuckin’ nuts s’more… ugh fuck, gonna cum… and fffffuckin’ fuck you silly… until tomorrow night… s-sound good, bitch?”  Drake held himself in check as long as he could, his orgasm fighting to be released.

“Y-yes Drake… oh fuck, YES MASTER!”  Greg had wanted to say those words to someone for so long, and just letting them go brought his climax on immediately.  His innards clenched around the Dragon’s dick hard and tight, and his swollen balls drew up tight to his pelvis, and his hard, throbbing dick sprayed jet after hot, pained jet of canine cum all over himself and the towels below him.

“Gods yes, YES!”  Drake impaled himself into Greg’s ass as far as he could, rocking his hips lightly as his cock twitched and coated Greg’s inner walls with his thick, viscous dragon seed, over and over and over for a good half minute, leaving Drake limp-limbed and satisfied, and Greg with a warm, pleasant full feeling he had never had before.  

“So uh, drake…” 
“Yeah Greg?”
“This doesn’t change anything between us on the team, okay?”
“I never wanted it to, dude.  I just wanted to know if we could fuck and be cool with that.”  Drake sounded a little younger, slightly more hopeful than his previous dominant tone.  
“You gonna ride me once in a while too?”  Greg asked, smirking a little.
“Y-yeah… hell yeah.” Drake sounded like he was blushing now. 
“Then yeah.  We’re cool.”

~~~~~~~~~~~~~
Approx. Word count at 2AM: ~1300
Finished word count: ~2090
Complete time: 5AM (after editing and proofreading)