The Jack Off Sessions Ch. 08

"So who came more? You or your friend?" Nick asked.

"I guess it depended on the day, but I usually came more in volume I guess, but he could cum again and again and again. One time I watched him cum nine times over the course of a day. Nine freaking times! It was crazy." Brent laughed.

"That's fucking hot. How many times did you cum?" Nick asked.

"That day? Just seven." Brent said.

"Just seven? Sheesh man, that's a lot. I think I hit five once, but I was dry cumming by that point."

"You gotta stay hydrated man. As long as you have fluids in your system, you're gonna shoot loads."

"Fucking hot, man. I love watching cumshots. I have so many cumshot compilations bookmarked. I could watch them for hours."

"Yeah, me too." Brent agreed.

"Nothing better than a big hard cock a big load, right?" Nick asked as he watched Brent stroke his manhood.

"Yeah, add a sexy girl like Sarah here and I'm all over it." Brent said.

"Shit man, I wanna see you cum. I bet it's impressive."

"I haven't done it since last night. I'm probably gonna make a mess."

"I definitely wanna see that."

"Yeah?"

"Definitely."

Sarah moaned rhythmically as Jake penetrated her. The POV angle looked down at her arched back and down to the flare of her hips as he slid his cock into her pussy from behind. His shaft was slick with her juices and he seemed to make it a focus in the camera lens as he pulled out and zoomed in at the glistening organ as he slapped it between her cheeks. He slowly inserted the head, her lips gripped his girth as if she was pulling him inside of her. His hands slid over her perfectly sculpted ass before he pushing back inside of her and grinding her ass once he bottomed out.

"Fuck, I feel you in my belly." She purred.

"You like this dick?" Jake grunted.

"You're gonna make me cum." She groaned as he picked up the pace and began to fuck her with a purpose.

Brent was getting close. One of his big turn ons was watching a woman genuinely enjoy themselves and Sarah clearly did. The way she backed into him as he thrust into her, along with the sounds of her moans, his grunts, the slap of flesh on flesh, and his ability to keep everything in frame sent Brent to the edge.

"Wanna watch me cum, dude?" Brent asked, keeping his eye on the scene. Considering the speed at which Jake fucked Sarah and the increasing enthusiasm of her movements, he felt like they were getting close. He could feel his own pressure begging to be relieved.

"Fuck yeah, man." Nick replied.

Brent spread his legs a bit, stretching the muscles of his inner thighs as he pushed his pelvis out. He looked down at his engorged cock, then at Nick as he watched with a glazed expression. Brent tightened his grip and pumped the thick veiny appendage with conviction. As he felt the familiar sensation right before the storm, he pressed the fingers of his left hand down to grip the base and pulled up on the shaft in a series of milking motions with his right hand.

He grunted. The head expanded to the size of a small apple and a torrent of thick semen shot through the air. A second load followed before the first could land with a splat on a distant bundle of wrinkled clothes on the other side of the room. Nick watched with amazement as the third and forth ropes of cum bisected the floor in front of them, splashing the dresser and a pile of books leaning against the closet door. The next few shots were just as intense and carried just as much volume, but Brent adjusted the angle and aimed toward his chest creating a small river of cum that pooled between his pecs and spilled down his abs. Nick watched with awe as Brent slowly drained himself.

"Holy fuck! You painted my room!" Nick laughed in astonishment. Though Nick was not unfamiliar with big cumshots, this was something else. He watched with amazement as Brent continued to stroke his massive appendage, glazing his torso with a thick later of seed. If Brent hadn't told him he came the night before, he would've believed this was the result of weeks of edging without a drop lost until now.

"Goddamn. I love me a good cumshot and that was the most impressive one I've ever seen." Nick stated as he stroked his own erection.

Brent smiled sleepily. His movements eventually slowed and the eruption of cum dwindled to a steady pulse of sticky fluid that he casually emptied onto his torso. Despite just having an orgasm, his erection remain rigid. He lowered his hands to his balls and gently massaged any residual semen he had yet to evacuate. As the uncontrollable quivers of pleasure continued to vibrate through his body, he allowed Nick a clear view of the spasming muscles behind his balls. He closed his eyes and exhaled, enjoying the bliss, knowing full well Nick was taking in every moment.

***

Christine dropped to her knees and made her way to James while slipping out her dress. By the time he was within reach, she was stark naked. Not a stitch on. Shaved, waxed, tanned and prepared for this moment. She hoped this young man appreciated his view from up there. She spent countless hours in yoga class, on the treadmill, and at the salon making sure she had what it took to still make men drool. Though she was a good ten years older than James, she was confident that she was in better shape than most of the girls he might have been with. Regardless, she had the experience under her belt to ensure that his time with her would be unforgettable.

She leaned into him, sliding her hands up his length. He was bigger than her husband, that's for sure. In fact, he would easily make it into her limited experience with monster cocks. With his length and girth, she was surprised at just how hard he was. There have been well endowed men in her past, but she found the bigger they were, the more it took for them to become completely engorged. His specimen, on the other hand, was hard as a rock. It stood proud, angled toward her vaulted ceilings. She could barely wrap her fingers around the thick base of his shaft. At the midpoint, it was wider still, likely requiring two hands. The head barely fit in her mouth, but she knew what she was doing and used enough saliva to make it work.

She could feel his heartbeat inside her mouth. She used her tongue to work her spit around, easing more inside of her. She felt Sams spread her legs, kneel behind her and slide inside of her wet pussy. She loved the sensation of being spit-roasted and she had been looking forward to this moment ever since Sam texted her about his new friend.

She pumped, fondled, squeezed, and sucked James with a focus and intensity that took years to master. She was working on autopilot as the sensations she was feeling made the world disappear. Sam slammed into her from behind, digging deep inside her most sensitive parts. She began to shudder and became light headed. The orgasm was so intense that involuntary cursed before blacking out.

The waves of pleasure that washed over her had color, sound, and the kind of emotional resonance that it seemed every moment of happiness during her thirty two years of life here on earth was focused into this one moment. She broke through the haze and found her body convulsing as her orgasms continued, her moans escaping her lips without any conscious effort on her part. She was in complete bliss.

As she opened her eyes, she saw that the two men were now kneeling over her writhing body, pumping their cocks over her, slapping her manhood on her face, breasts, her trembling body. She watched as one, then the other began to cum. As their combined seed splashed over her, coating her, sliding down her cleavage, between her legs, all over her face, she continued to finger her sensitive clit until one more wave crashed over her. Her eyes rolled back into her head and she suddenly couldn't see or hear. She was in a warm limbo where nothing existed but pure, intense pleasure.

Part 4.

As the video continued to play, he could hear the audio increasing in intensity. Jake was getting close to cumming and Sarah was encouraging him to get there. Brent opened his eyes to find Nick sitting closer beside him than before. He was intensely stroking his cock, biting his lip and looking down at Brent's cum covered body.

"Can I use some of your cum as lube? I'm getting close." Nick finally asked. Brent looked over to him with a content expression on his face. The powerful orgasm he just experienced had released enough endorphins that left him agreeable to just about anything. He wiped his hands on his thighs then folded them behind his head. This wouldn't be the first time he let another guy use his cum as lube.

"Okay." Brent agreed. He watched as Nick scooted to him within inches. He could feel his body heat. Without slowing his pace, Nick reached his free hand over to Brent and scooped a handful of his seed off his chest. He slid the hand over his erection and groaned as he lubed up. He visibly became harder and more aroused as he worked Brent's seed over his shaft and balls. His groin glistened obscenely as his fingers masterfully explored every inch.

"Fuck man, you're still hard?" Nick asked as he looked over Brent's cum covered body.

"Yeah man, I'm pretty fucking horny." He replied while flexing his oversized erection as if to illustrate that he was as ready as ever for more.

"Can I see?" Nick asked.

Brent shrugged his shoulders.

Nick leaned over Brent's lap and wrapped his fingers around the thick shaft and squeezed.

"So fucking hard." He groaned while continuing to stroke his own erection with Brent's cum. Instead of letting go as Brent anticipated, he loosened his grip but began to explore Brent. From the bulbous head, down the shaft, to his low hanging balls, Nick took advantage of the opportunity to etch this moment to his memory permanently. Nick resumed his pace, stroking both Brent's erection and his own.

"Fuck," was all Nick could get out before he began ejaculating uncontrollably. A steady moan escaped his lips as semen erupted from his penis. Based on what Nick was doing to Brent, his matching movements milked his shaft, draining his balls in the process. Brent was no stranger to handjobs, but that didn't take away from his enjoyment of them. Anything that involved his penis and someone else's attention was sure to be a recipe for success.

Nick eventually slowed his pace, but kept his hand wrapped around Brent's throbbing erection. Brent kept his hands folded behind his head and closed his eyes, sharing in the euphoria they were both experiencing. A gentle undulating squeeze came from Nick's hand, which turned into a steady stroke.

"I can't believe you're still hard after cumming that much." Nick said to Brent, leaning a little bit closer than before.

"Feels good, man." Brent was all he managed to say. He liked the sensation he was feeling. This whole experience excited him. In his experience with James, rarely did they formally intend to get each other off. It was common for them to touch, squeeze, and stroke each other. However, when it came to finish the job, they almost always let the owner take things over the finish line. Other than a handful of extended intense edging sessions, this was always the case.

Reclined back on an unfamiliar bed, Brent enjoyed the sensation of freedom he was experiencing. He could feel Nick's hands explore his length and girth under the thin pretense of seeing how hard he was. It didn't bother Brent one bit. As long as things continued to feel as good as they did, he would continue to let events unfold.

"You mind if I get down on the floor between your legs? Kinda uncomfortable leaned over like this, all twisted over." Nick said, straightening out his back, keeping his fingers firmly wrapped around Brent's cock.

"Yeah, ok." Brent answered, subliminally adding, 'as long as you keep what you're doing.'

Without letting go, Nick lifted himself from the couch and lowered himself onto his knees on the floor between Brent's legs. Brent watched as the combination of their seed slide down Nick's bare torso and onto his lap. He took advantage of the position by using his other hand to explore Brent's balls as he continued stroking his cock.

Nick's fingers drifted lower, behind Brent's balls and under, toward his ass. Brent recalled his week in the cabin and how Allison and Claire made a game of finding all of his pleasure points. Brent spread his legs a little more giving Nick more access.

"Sensitive back here?" Nick asked as he brushed his fingers against Brent's taint while playing with his balls.

"Yeah."

"Feel good, though? Right?"

"Yeah."

"I'm getting fucking tempted here, Brent. You ever get oral from a guy?" Nick asked licking his lips.

"No. Well, maybe. Probably, I guess." Brent stuttered.

"You're gonna have to give me more than that." Nick chuckled.

"Me and my friend used to go to this adult bookstore in town. They had a gloryhole." He explained.

"A gloryhole? You... use gloryholes?"

"Well, yeah. Not since I got here. But, back home... sometimes, yeah."

"That's pretty hot." Nick almost whispered to himself

"It's convenient. Easy way to get off." Brent justified.

"I bet." Nick slapped Brent's cock on his cheek. Brent looked down and watched him.

"Sorry. Habit. You know, probably ninety percent of the time, you're getting a blowjob from a guy when you use a gloryhole." Nick said.

"You're probably right."

"That doesn't bother you?" Nick asked.

"Not really. I mean, a mouth is a mouth, right?" Brent quoted James.

"How many times have you been to a gloryhole?"

"Shit, I dunno... a couple dozen times, maybe"

"That's a lot."

"Yeah. When I found out I could get free head anytime I wanted it, I couldn't help myself."

"You like head, huh?"

"Yeah?"

Sarah arched her back as Jake slid in and out of her steadily. Her thighs were wet with her dripping juices. Jake ground down into her making her groan uncontrollably.

"So, you're okay with letting me jack you off, right? Doing a pretty good job, you'd say? Feels good?" Nick asked, while continuing to fondle Brent.

"Yeah, really good."

"Would it bother you if I put it in my mouth?" Nick asked.

"You wanna suck me off?"

"Just pretend you're at a gloryhole." Nick said as he suddenly took Brent into his mouth. Any resistance Brent had dissipated almost instantly. Nick's masterful tongue work and tenaciousness had Brent's cock at attention.

Nick eased Brent back into a reclined position and lifted his legs slightly. He spread his thighs and enveloped his balls with his mouth. Brent's head lolled as the sensations of pleasure guided him. He could feel hands expertly milk his shaft as a hungry mouth explored his balls. He felt very exposed in this position, but it felt too good to stop.

As if on queue, Nick's saliva lubricated fingers slid past Brent's balls and further back toward the crack of his ass. Brent looked between his legs to see Nick tug on his leaking manhood with one hand, his mouth hungrily finding new areas to gently suck, and feel fingertips of his other hand gently massage his taint and the entrance to his ass.

His breath hitched. He was in ecstasy. James called this area on Brent his 'g-spot.' They had discovered over the course of their time together that Brent was particularly sensitive here. Stimulating this area while masturbating often resulted in Brent's inability to fight or even slow the impending orgasm. Many an edging session was cut short once they discovered this weakness of Brent.

Nick released Brent's balls from his mouth and began to focus on his shaft. He timed his hands with his mouth to create a vortex of tight, twisting, sucking sensations that started with the base and ended the tip. He managed to coordinate his other hand to explore Brent's balls and more sensitive areas, creating a perfect storm of pleasure that was building to a plateau.

"Big fucking dick." Nick growled.

Brent looked from Nick between his legs to Sara on the screen. She was bent over her vanity, being pounded by Jake from behind, verbally preparing to receive his seed. Brent looked down at his saliva covered cock and the guy so desperately trying to bring him pleasure. Brent looked back up at Sarah as she spun around and got on her knees. Getting ready for Jake's big release, Brent let the pressure build and build...

He felt almost disconnected with his penis, watching it be masterfully worked by an artist of the oral skill set. He almost had an out of body, third person perspective, seeing himself laying back, propped on that bed, with a willing mouth and hands probing for and successfully finding his pleasure points. He willed himself back into his body in order to better experience these new sensations. He could feel the gentle squeeze and tug of a hand, a wet mouth suck and lick, fingers exploring. He allowed himself the freedom to enjoy it all.

His muscles tensed, and began to rhythmically spasm between his legs. Brent groaned. Nick began sucking the area behind Brent's balls as he stroked his massive cock with both hands as the convulsions continued. Nick opened his eyes to see a thick rope of cum shoot far into the air and landed on the pillow next to Brent's head. Nick snapped out of the trance and aimed Brent's penis at his chest.

He could feel the powerful blasts of the thick seed crashing against his pecs as he continued to milk Brent's throbbing appendage. He expected the onslaught to diminish on several occasions, only for it to gain in strength, pulling from an almost supernatural power source. By the time Brent's orgasmic trembles died down, Nick was almost completely covered in Brent's cum. Textbooks were splashed with it, his carpet was soaked in it, and a significant percentage of his laundry was stained by it. He imagined he'd have to open the windows to air out his room to prevent it from smelling like an orgy party took place.

If Nick wasn't so aroused by it, he'd have been laughing at the excessiveness of it all.

***

By the time Brent made it back to his room, he didn't know what time it was. He barely knew who he was, as a matter of fact. His skin felt sticky underneath his clothes so he took them off. He sat in his desk chair and looked at his naked reflection in the closet door mirror. Though he wiped most of the cum off his body in Nick's room, there were still moist valleys between his pecs and in the crease of his abs. He needed a shower desperately, but the throbbing erection between his legs would need to be dealt with unless he dared to walk down the long hallway to the bathroom while struggling to hide it. His ringing phone broke his trance. James was calling. He quickly answered it.

"You won't believe what just happened," the both simultaneously said.