His Little Masochist

"I'm going to cum in your ass soon Jayden, I hope you're prepared."

"Please don't do that Richard... please?"

"I'm-cumming! Nnnnhhh" With one final thrust into Jayden, Richard closed his eyes and shot his thick ropes of hot cum into Jayden's ass.

"It's so hot..." Richard slowly pulled his cum-covered dick out of Jayden's ass and grabbed a water bottle off the floor and put it up to Jayden's ass to catch the cum dripping out. When most of the cum was in the bottle Richard grinned, capping the bottle and putting it aside. Richard rolled Jayden onto his back and moved to Jayden's face. He pried Jayden's mouth open and started to push his dick into Jayden's mouth.

"If you bite me you will regret it."

"Mmm mmmmmm mMm."

"Haha, you shouldn't talk when there's something in your mouth." Richard started to push his dick further into Jayden's throat until his balls were resting on Jayden's nose and he started to pull back out, slowly. He rammed his way back into Jayden's tight throat, grunting as he did so. He started rhythmically pumping in and out of Jayden's throat and he reached out, grabbing Jayden's dick and starting to slowly move his hand along the shaft, causing it to twitch and throb.

"Somebody's excited." Jayden just coughed a little, tightening his throat around the head of Richard's dick, eliciting a moan from him. Richard flicked the head of Jayden's dick, causing Jayden's hips to spasm and he coughed again. Richard fell forward and started to gently run his teeth along the edge of the head of Jayden's dick.

Richard's dick started to swell and his breathing lost rhythm. Richard started to groan a little as he straightened up, his cock was twitching as he thrusted in and out of Jayden's throat. Right before Richard came he pulled out and shot his thick cum on Jayden's neck and chest.

Jayden gasped and coughed as Richard's shoulders relaxed and the last bit of cum dribbled from his cock to Jayden's chin. Richard moved so he could easily access Jayden's throbbing dick as it stressed against the fishing line. Richard ran his finger along the underside of Jayden's dick. Jayden's eyes rolled back as his mouth opened a little and his head went back.

Richard grinned and started to massage the head of Jayden's cock. Jayden's tongue lolled out of his mouth and he moaned as his hips bucked, his dick swelling against the line. Richard chuckled and he gripped Jayden's dick firmly. Jayden's dick was already a third again it's original size and the fishing line was making lines in Jayden's dick. Jayden's eyes rolled back and he started to drool as Richard started to slide his hand up and down the shaft of Jayden's cock. As Jayden's whole body started to convulse Richard let go and walked over to Jayden's dresser and started looking through drawers.

"Ha, I figured you'd have something like this," Richard pulled a box out of the dresser and opened it, peering inside he found a bunch of things but two of them caught his eye, a vibrator and what appeared to be a vibrating leather strap.

"What could these be used for I wonder?" Richard walked over to Jayden and grabbed the bottle of cum. He dripped some along the vibrator and started to push the vibrator against Jayden's ass hole. Jayden was still too dazed from his cumless orgasm to struggle as Richard rammed the vibrator into Jayden's ass. Richard turned the vibrator up to its maximum setting and grinned as Jayden's hips bucked a little. Richard undid the leather strap and held Jayden's balls as far away from his dick as possible and tightened the leather strap around his scrotum. He turned the vibrator on and Jayden's hips started constantly bucking.

"Somebody's quite happy I see." Richard looked around some more and found the dagger from last time that Jayden had visited Richard's house. Richard went back over to Jayden and pulled Jayden's shirt off of him as much as he could and then started to drag the tip of the dagger along Jayden's chest. Jayden gasped and bucked while Richard just smirked and started applying pressure with the dagger at the base of Jayden's dick. Jayden tried to stop his hips from bucking but only succeeded in reducing it, and every time they bucked the pressure from the dagger increased.

"If you buck too much more you might start to bleed a little."

"Then... m-make it.. s-stop."

"Hmmm... no, I think I'm good," Richard removed the dagger. He turned it and slapped Jayden's thigh with the flat of the dagger, Jayden screamed as a red mark in the shape of the dagger formed. Richard smirked and he slapped the other thigh, eliciting another scream from Jayden. Richard slapped Jayden's dick with the flat of the dagger a few times, each time it throbbed and got a little more purple.

"You appear to be losing circulation Jayden, is it sensitive?" Richard flicked the head of Jayden's dick and he winced as his hips bucked violently. "I guess so." Richard started to gently run his hand along the shaft of Jayden's dick. While he massaged the shaft of Jayden's dick, Richard pressed the tip of the dagger against Jayden's ball sack, right in between his balls.

"Be careful you idiot, that thing's pointy!"

"I know exactly how pointy it is Jayden," Richard started applying more pressure and started squeezing Jayden's dick a little tighter. Jayden inhaled sharply and his hips twitched a little. Richard started to speed up, his hand just barely touching the head of Jayden's dick, causing a spasm every time.

Jayden's dick was now half again its original size and Richard was amazed the fishing line hadn't broken or cut Jayden yet. Jayden was bucking uncontrollably so Richard removed the dagger and started to lick and suck on Jayden's balls. Richard started to massage the head of Jayden's dick as he nibbled on his balls. Jayden's hips bucked uncontrollably and His balls started to swell and turn a little purple. Richard pulled back and grinned.

"Did you just orgasm again?"

"No- I... idiot!"

"You did!"

"No-I," He was cut off by Richard tugging on Jayden's balls and licking along the underside of his cock. Richard's swirled his tongue around on the underside of the head of Jayden's dick. Jayden twitched again, his eyes rolling back.

"You are just loving this aren't you Jayden?"

"No... I... Nnnhh."

"Finding it difficult to speak?" Richard grinned and teasingly licked the tip of Jayden's dick.

"No... I... I can speak... just fine..."

"Obviously not." Richard straightened up. He started to remove the fishing line and leather strap around Jayden's swollen genitals.

"Ahhh..."

"Feel better?"

"Much..."

"Well I'm sorry to inform you that you probably won't like what follows either," Richard finished untying the fishing line and a small amount of cum dribbled from the tip of Jayden's dick.

"That's it? From two orgasms? Just that measly little drop?" Richard grinned and grabbed the vibrator in Jayden's ass and started to twist it.

"No stop, what are you doing?!"

"What does it feel like I'm doing?"

"Stop this now!"

"Hmmm... No, you're clearly liking it, I mean your dick is back to twitching again." Jayden's dick was back to a normal size a color but was indeed twitching. Richard twisted and turned the vibrator and Jayden's dick twitched with more and more vehemence each time. Jayden's breathing started to become staggered and Richard grinned.

"Look at you, almost cumming from a vibrator in your ass." Jayden just blushed and his eyes closed. When Jayden's dick started to throb and grow Richard quickly pulled the vibrator out of Jayden's ass. Jayden relaxed and his face drooped. Richard grinned at Jayden's exhausted state.

"I'm not done with you you know," Richard started to tie Jayden's wrists to the bed posts, then his ankles. Jayden looked up and before he had time to figure out what was happening Richard tied the last limb to the bed.

"What now?! I can only take so much you know!"

"I know that, I'm going to put you at your limit, then I might stop."

"I don't think I can take much more..."

Richard pulled a coiled whip out of his pants pocket, grinning and turning to look at Jayden. Jayden groaned as Richard uncoiled the black leather whip and cracked it in the air next to Jayden. Jayden yelped and tried to squirm away unsuccessfully.

Richard laughed and whipped Jayden across the chest. Jayden screamed as a red line appeared on his chest. Richard trailed the whip down Jayden's torso and to his crotch, Jayden tensed up. Richard whipped Jayden's stomach, Jayden's scream muffling the crack of the whip. Richard whipped Jayden again, hitting his leg dangerously close to his twitching dick.

"Look what we have here Jayden, You look like you're having a little too much fun." Richard let the tassels on the end of the whip tease the tip of Jayden's dick.

"Nnnn no. I'm not liking this a-a-at all," his speech was broken by his hips' twitching. Richard grinned and moved the whip, watching Jayden's dick as a drop of precum oozed out of the tip.

"You clearly are Jayden, you're dripping precum," Richard bent over and licked the tip of Jayden's dick. Jayden moaned but that quickly turned to a scream as Richard whipped his chest again. Richard moved to the other side of the bed and started to choke Jayden with one hand while he whipped Jayden's chest with the other. Jayden's eyes rolled back and his hips twitched, unable to scream. Jayden's eyes closed and Richard whipped across Jaden's hips, almost touching the base of Jayden's cock. Jayden had stopped moving and Richard released his throat. He started untying Jayden quickly and flipped him over. Jayden opened his eyes a moment after Richard finished tying the last bit of rope.

"How did I get like this?" Jayden's voice was raspy and his vision was blurred.

"You passed out and then I flipped you over." Richard ended his sentence with a crack of the whip and a line of pain down Jayden's back. Jayden's scream was scratchy and his throat hurt. Richard whipped him again across his upper back, then again across his ass. Jayden's chest and stomach seared in pain, but this pain was bright and new. Richard grinned and whipped him again across the middle of his back. Jayden tried to get away but he couldn't do anything about the ropes. Jayden whimpered as Richard whipped him again and another line of pain seared across his ass. Richard flipped the whip around and started to press the base of it against Jayden's asshole.

"Noo, please not there," Jayden wriggled, trying to get away but Richard just slapped his ass and pressed a little harder.

"Why not? I know you love it," Richard pressed harder and Jayden's dick twitched and started to swell. Richard pressed a little harder and the handle of the whip popped into Jayden's ass.

"Nnnnnhhh," Jayden moaned into a pillow as his ass was penetrated by the whip. Richard left it in Jayden's ass and straightened up, stroking his cock a little as he looked at Jayden, his back crisscrossed with red and a whip sticking out of his ass. Richard looked around the room and saw a candle and a lighter on Jayden's dresser. He walked over and lit the candle, he carried it back over to the bed and tipped it over the middle of Jayden's back. A drop of molten wax fell on Jayden's back and cooled instantly, Jayden screamed and wriggled, trying to escape. Richard grabbed the whip and twisted it a little. Jayden's eyes rolled back and a couple more drops of wax fell on his back. Richard set down the candle and lifted Jayden's pelvis a little so he could position Jayden's dick so that the bottom was facing up. Richard started gently stroking it and picked the candle back up. It had built up a decent amount of wax and he dripped it onto the base of Jayden's spine. Jayden squirmed and whimpered as Richard twisted the whip some more. Richard let a drop of molten wax fall onto the underside of Jayden's dick, he whimpered as another drop fell, this one on the edge of the head of his cock.

"I'm going to set this candle on your back, if you move too much it'll tip over, so stay very still." Richard set the candle on Jayden's back and started to tease Jayden's dick with the tassel on the whip.

"Stop, Richard please stop, or take the candle off... please..." Richard laughed a little, then Jayden's hips bucked a little and the candle tipped over. Richard quickly grabbed it, but Jayden had felt the heat from it and wax had spilled onto his back, he screamed and Richard pushed his head into the pillow.

Richard pushed the whip a little deeper into Jayden's ass and twisted it a little. Jayden's hips twitched and Richard chuckled. Richard moved down to the end of the bed and started stroking Jayden's cock as well as his own. Jayden started twitching, his eyes glazing over. Richard grinned and sped up on both of their cocks. Richard looked around a little, looking for the bottle he had used earlier and upon finding it, he got up and brought it back with him. He went back to jerking the both of them off. He was moving much quicker on himself than on Jayden. He was moving his hand such that he barely rubbed against the head of their dicks, Jayden bucked every time that Richard's hand moved along the head of his cock. When Richard felt Jayden's dick start to swell he held the bottle against the tip of Jayden's dick and collected all of his cum. He capped the bottle, and went back to jerking both of them off. When he was about to cum he stood and came on the small of Jayden's back. He also dumped the contents of the bottle on his back.

Jayden squirmed a little and made a little noise of disgust. Richard sat back down and started to jerk Jayden off again.

"Nnnh no I'm too sensitive now please..." Richard just chuckled and then stood, a look in his eye like he had just had an amazing idea. He pulled the whip out of Jayden's ass and picked up the vibrator and he pushed it into Jayden's ass in one smooth motion. Jayden moaned as Richard turned on the vibration. Richard grabbed the leather strap and put it around the head of Jayden's dick and some of the shaft. Jayden's hips bucked uncontrollably and Richard grinned. Richard looked at the alarm clock on Jayden's dresser, it read 4:24.

"Damn. I have to go soon."

"Nnnnhhhhhnnnhh," Jayden couldn't say anything, he just moaned.

"Hmm... Oh! Neat; those ropes are nylon, you know what that means?"

"Nnnnhh"

"It means that they will melt." Richard looked around and grabbed some books, making a stack of them under one of the ropes restraining Jayden's arms. Richard started looking around the room and found all his clothes and got dressed. He made sure the vibrators were on their highest setting and looked out the window. Not seeing his ride coming down the road he whipped Jayden's ass a couple times. Jayden arched his back as he came another time, moaning loudly and squirting ropes of cum onto the bed.

"How much cum do you have Jayden? Jeez," Richard grinned, but then he heard a honk and looked out the window, seeing his ride he said "Oh, time to go." He placed the candle right under the rope and stood there a moment, the rope started to get a little shiny and he knew it would melt eventually.

"Bye, see you later."

"Nnnnnhhnn"

Richard made sure he had everything he came in with and got in the car. Jayden was still tied to the bed, the vibrators were still running. His whole body convulsed rhythmically and he could smell burning plastic. He pulled at the rope and it stretched a little. He started pulling on it harder and harder. He threw all his weight back, trying to break the now thin rope, but the candle tipped over and splashed his face with molten wax. He screamed and the extra stimulus from his cock rubbing against the sheet made his whole body convulse and he came again, his body trying to curl up, sucking as much out of him as it could. The flame went out as soon as it touched the sheet and Jayden just layed there.

After he had recovered from his post-orgasm haze Jayden realized the rope had stretched enough to where he could reach the other rope and untie it. He untied his wrists and was fighting his hips' twitching as he peeled the wax off his face. He tried to get at the vibrators but the angles were all wrong and he knew he'd have to untie his ankles first. He wriggled around to reach his ankles and the vibrator in his ass felt like it was pushing against his organs. He was finally able to roll over and turn off the vibrators. He undid the leather strap and tossed it on the floor, then he slowly pulled the vibrator out of his ass, his hips still bucking occasionally. He laid there for a minute then swung his legs over the side of his bed and tried to stand but his knees buckled and he fell back onto his bed. He tried again and walked to the bathroom, still naked. He ran a hot bath and let himself sink into the bubbles.