The Jack Off Sessions Ch. 08

"So, James right?" She asked. Her voice was melodic and playful. James wondered what it would sound like when she was moaning.

"That's me." He confirmed.

"Sam says you have a big cock." Christine asked bluntly. He eyes were focused on the bulge between his legs. He wished he wore loose shorts instead of jeans.

"Uh." James looked at Sam. Sam smiled and hitched his shoulders.

"Don't be shy. We're all consenting adults here, right?" She said.

"Yeah, I guess."

"Well? Let's see it."

The room had become increasingly warm from the moment James stepped into it, and at this point it felt practically hot. James quickly took stock of his situation. Here he was, standing in front of incredibly attractive older woman asking him to show her his penis. To his side was a classmate, with whom he masturbated with the day before. The whole situation was incredibly surreal, but not too far off from the kinds of fantasies he daydreamed about while working under the hot sun mowing lawns of homes not unlike the one he currently stood.

He often glimpsed the trophy wives of his clients as he worked. From time to time, they caught his eye because of their silken hair, bare shoulders, or modest beauty surrounded by a mundane environment. Stood before him was the pinnacle of every attractive housewife he had filed away in his spank bank up to this point. Christine was heads and tails more stunning, sexy, and notably confident. Her clear blue eyes pierced him. The cinched waist of her sundress promised a masterpiece beneath. He could make out her unburdened breasts by the way her stiff nipples pressed against the thin material. Her long tanned legs were golden and gleamed with promises he could only imagine.

James was hard, very hard. He wanted to show her his manhood. He wanted her to see his thick eight inches. He wanted to see her eyes grow, her lips get wet, her skin pressed against him as he sunk deep inside of her. James unbuckled his belt, unzipped his jeans, and freed his throbbing erection. He was shaved smooth and throbbed with anticipation. Her eyes did get wide, her lips did get wet. She gasped.

"Damn, you weren't kidding Sam."

***

Brent and Nick continued their conversation as they whittled down their food to respectable smears on the plates before them. They remained on topic as the elevator brought them up to the seventh floor. The continued the conversation as they entered Nick's room.

"I gotta remember which one of 'em has it, but it's definitely here somewhere." Nick headed for his desk as Brent closed the door behind them.

Nick's room was a mirror image Brent's, but stretched twice as wide. Brent wondered how Nick managed to acquire a two-resident room without needing a roommate. An oversized beanbag chair and entertainment center filled the spot where there should have been second bed and desk. The white painted cinder block walls were decorated with superhero movie posters. The place was a mess, but not offensively so. It was a typical college guy's dorm room.

"Found it." Nick held up a Ferrari red usb flash drive. He plugged it into the back of his tv, picked up the remote and turned it on. He navigated through menus until he reached a folder with several videos in it. Brent's eyes scanned to see the flesh-tones in the little thumbnails and found plenty. Nick selected one in particular and a video began to play.

They took seats on either side of Nick's small twin bed and watched the scene begin.

The brunette wearing a matching set of white bra and panties and sitting in front of a mirrored vanity. She lightly applied makeup to her already flawless face and looked suspiciously at the reflection of the man holding the camera. She was exotically beautiful, with an olive complexion and a thick mane of straight dark brown hair that stopped at the midpoint of her narrow back.

"Seriously Jake, turn that fucking camera off." She looked over her shoulder at him with a smirk on her face. He looked up from the viewfinder at his reflection and wiggled his brow.

"You're beautiful, Sarah. The camera loves you." He placed a gentle hand on her bare, sun-kissed shoulder.

"Yeah, right. You just wanna make another video of me sucking your dick." She said defiantly, pouting as she applied lipstick.

"I gotta complete the collection, babe." He joked, and dodged a playful elbow to the stomach.

"You better fucking not. If find out you showed these to any of your little friends I'm gonna cut your dick off." She joked.

"This is just for us, babe. Don't worry. It'll be locked up safe and sound." He said.

She looked at him suspiciously.

"It's my birthday." Jake continued, pleading, almost pouting. He nuzzled her from behind. She leaned back into him and exhaled. A smile spread across her face as he whispered something into her ear before nibbling on her lobe.

"We're gonna have dinner with your family in an hour. Maybe when we get back, hon." She weakly protested, straightening up and continuing with he makeup routine.

"How about a preview? Gimme something to think about while we're mingling with the fams" He begged, pulling down his basketball shorts and revealing his already erect penis. He playfully parted her hair behind her ear with it and slid it down the side of her face. She gave him a look and turned around.

"If you fuck up my mascara, you're dead." She smiled at him mischievously and placed her brush on the vanity top before turning to face him.

She slid his shorts down to his feet and he stepped out of them. She ran her hands up the side of his calves, behind his knees, and up the back of his bare thighs. She reached between her breasts and unclasped her bra, freeing her them for his groping hands to explore.

He shuddered as she ran her silken hair up the length of his throbbing shaft. Every cappuccino strand gently brushed his rigid member as she arched her back and leaned into him. She parted her wet lips and caught the head of his penis with her tongue. Using it as a guide, she slid him into her warm mouth and began to gently suck, using a liberal amount of saliva as lubrication.

Jake seemed to have little self control as he began rocking his hips in time with her bobbing head, sliding more of his cock inside her mouth every time.

After a few strokes, he was down her throat and holding the back of her head steady. He ground his pelvis into her face, feeling every inch of his engorged manhood tightly wrapped in a wet embrace. She gently pushed her hands against his hips and he loosened his grip. His spit coated erection slid back out of her mouth. She turned her head to the side and slid her lips down his shaft as she caught her breath. She smiled with satisfaction seeing the ecstasy on his face. She gently massaged his balls with one hand and pumped his cock with the other as she worked her way back up with her mouth. She locked eyes with him as she slipped the head of his penis into her mouth, past her lips until he was back down her throat.

Despite the mascara running down her cheeks, she seemed to be a ready and willing partner.

"Damn." Brent gasped.

"Yeah. You ever get head, like that? Balls deep?" Nick asked.

"A couple times, yeah." Brent answered honestly. Though he could count all of his sexual partners on one hand, the amount of sex with those few partners was well above average at this point in his young life.

"Dude, I saw how big you were last night, remember? I can't imagine many people being able to handle that beast when you're fully hard." Nick laughed.

"Well, where there's a will there's a way." Brent joked.

Brent noticed Nick was sitting kind of skewed. He imagined it was because he was probably horny and trying to hide it. Brent internally heard James warning him that letting the awkwardness take over now would probably end things prematurely. 'Lean into it and see where it goes,' James said to Brent in a Yoda like voice.

Brent shifted the pillow behind him to support his head and shoulders. He reclined into a more relaxed position, casually parted his legs a little to allow space for his manhood to grow. It was obvious now that he was very well endowed and was more than semi erect. He could feel Nick's eyes on him as the bulge increased in size and became more defined in shape.

The video continued to feature Sarah's enthusiastic blowjob technique. Jake made no attempt at pretending this would be just a quick "preview" of things to come. The wet sucking sounds rhythmically played through the speakers.

"Hey, Brent... can I ask you something? Nick finally asked.

"Sure." Brent replied.

"So, you're straight, right?"

"Well... yeah. Why?" Brent answered, a little hesitant. Here it comes, he thought. How far can I 'go with the flow' before I can't go any further?

"Well, here we are... watching porn together. We're both obviously getting pretty horny. I rarely get like fifteen minutes into this scene before I whip it out and start beating it." Nick said, conspicuously squeezing his erection though the fabric of his cargo shorts.

"I don't wanna weird you out or anything, but either we cut this short soon so I can take care of my needs, or we can stay here and chill..." Nick continued, trailing off.

"Go ahead, man. I'm no prude." Brent answered, committing to see where things would lead. James would be proud, he thought to himself. He'd probably be slow clapping right now. He wondered if Nick would ask him to leave at this point so he could take care of business or if the sexual tension Brent felt would result in a different outcome.

"Really, you okay with that?" Nick asked.

"Yeah, man. It's cool. It wouldn't be the first time for me." Brent confirmed.

Part 3

With that approval, Nick stood up and closed the window blinds, casting his room in darkness. Brent kept his eyes on the screen as Sarah's mascara-tinted tears ran down her face with Jake's ever more energetic movements. The blowjob had turned into a full on face fucking. Her perfectly styled hair was now just a handle that Jake used to help guide her mouth. Brent had a hard time picturing her in the cafeteria earlier, perfectly civilized. A pretty little innocent co-ed, with nobody the wiser.

Nick returned to his spot on the bed next to Brent without anything but a shirt and holding his erection in his hand. Brent looked over and estimated Nick was a little bigger than average. Maybe seven inches or so. He also had a slight sideways curve in the shaft and adopted the popular trend of shaving everything bald just like James. The head was distinctly pinker and larger than the shaft and the thickest part of the whole package.

Nick seemed to completely at ease being nude around Brent. Definitely an exhibitionist, Brent thought. He accepted at this point that he himself had exhibitionist tendencies, but often wondered how far that would extend. Most of his sexual exploration involved James to some degree. Brent suppressed any self doubt that began to form and tried to relax. James would say, go with it. So, fucking go with it, he thought to himself

"Kinda weird with just me doing it, to be honest." Nick said after giving Brent sufficient time to acclimate to the sexually charged atmosphere. It was obvious that both men were comfortable with a little manual stimulation out of complete privacy, but exactly how comfortable hinged on Brent's next move.

"You ever jack it with another guy in the room?" Brent asked, anticipating where this would go. He thought about how James would react when he told him he found a new jack off buddy, just a day after they spoke about the subject. He thought about all the times he and James spent masturbating together and exploring their sexual desires in each other's non-judgmental company.

"I have three brothers around the same age. By the time we all hit puberty, we'd have jack off sessions most nights. One of us would be up trying to fight the urge, another one wakes up, we start looking at spank mags, and the next thing you know, it's a party."

Brent laughed.

"I'm no stranger to being around other guys if that's what you're asking. I'm discreet. If you want to join in, the more the merrier. What happens in this room, stays in this room." Nick grinned at Brent.

Brent followed Nick's gaze as it wandered between his legs. Brent looked down at his groin and saw the obvious lump that had developed while they were talking. He could feel the pressure and wanted to give it some room to grow. Nick obviously seemed willing, encouraging, and excited for Brent to join him, so he stood.

Brent recalled the handful of times he stripped down to an unsuspecting audience for the first time. He had performed this act in front of his best friend James more times that he could count, and almost each time James appreciated it as if it was his first. He often commented and complimented Brent's size to the point it was as comfortable for him as hearing a morning greeting, but much more charged. James's sister also often enjoyed this show of manhood, as well as her roommate Allison. Their first time seeing how well endowed he was triggered a summer of debauchery that remained a highlight in his young life. His neighbor Jennie's reaction was more complicated. Her obvious crush turned into a borderline obsession that almost spiraled out of control. From the strangers on the other side of the glory hole in his hometown adult bookstore, he encountered laughs, gasps, curses, silence and everything in between. It always excited him to have new eyes take in his most private part, and he couldn't wait to see Sam's reaction.

"Okay..." Brent unbuckled his belt and pulled down his jeans and underwear. He kicked them into a pile and nudged it next to his backpack leaning against the wall. He laid back on the Nick's bed using a pillow to prop himself up. He parted his legs, letting his manhood spring up and slap his flat belly. At well over nine inches in length, he dwarfed Nick. At almost twice his thickness, Brent's erection was almost comically large.

He pressed his fingertips to the base of his base of his shaft and flexed as he slid the tight grip of his other hand up the length until he palmed the head and squeezed.

"Damn." Nick gasped. "That's a big fucking cock." Nick's mouth was agape, his eyes glued to the spectacle.

"Thanks, man." Brent said. Brent worked his hands over every inch of his erection. His is fingertips masterfully massaging every sensitive nerve ending. He tugged it while massaging his balls, angling his body to give Nick a better look. The time he spent masturbating with his best friend gave him a lot of experience giving his audience a good view.

"I mean, I thought it looked pretty big yesterday, but you weren't fully hard like this. That's really damn impressive, Brent." Nick gushed.

In response, Brent continued to stroke his manhood, coaxing it to almost unbelievable proportions before Nick's disbelieving eyes. It throbbed with his racing heartbeat. The unshaven triangular portion above the groin was kept short and neat, the rest was shaved smooth and bald. Every inch was clear and visible. Each vein, valley, and thick bulging muscles were well defined. His scrotum was relaxed and his heavy balls bounced with every stroke. He worked it slowly, giving Nick an opportunity to take it all in visually.

"You've obviously done this before. You sure you're straight?" Nick chuckled.

"Yeah. I mean, I used to jack off with my best friend back home all the time. I don't think it's really a big deal." Brent said, surprisingly casually. He impressed himself at how relaxed he seemed. Inside he was a ball of excitement and electrified nerves.

"I dunno, Brent. For some guys it's a pretty big deal." Nick was in no way paying attention to the porno playing on the television. He was solely focused on Brent, almost drooling.

"The guy I did it with is my best friend. We grew up together, hit puberty together and... well, did everything together."

"Including jacking off together."

"Yeah."

"You ever jack each other off?" Nick asked.

"A couple of times."

"Hot. Tell me more."

"Well, sometimes we'd have contests, you know. Like, we'd see who was harder, who could cum more, shoot further, stuff like that." Brent realized how it sounded as soon as he said it. 'Like a contest... to see who was harder.' So, we'd grab each other's dicks and jack each other off for while, nonverbally understanding that this brief moment was meant to bring each other the most pleasure possible, before time ran out, of which there was no agreed upon time limit. Brent started to blush, but continued to fight any uncomfortable feelings away. "Grabbing and squeezing led to stroking and cumming... you know how it goes."

"He must have worshiped that thing. I mean, straight, gay, bi, whatever, you've gotta admit, your dick is pretty fucking epic. Everyone likes big dicks. I don't know a single person that wouldn't appreciate a big fat hard cock like yours there." Nick said.

"Thanks, man. James is pretty big too, to be honest. Last time we measured, he was over eight inches."

"Shit, that makes you nine-ten inches or so?"

"Something like that."

"I'd have liked to see you and your friend together. That would have been something else. I mean, other than in pornos, you're never gonna see two two super hung guys together doing stuff like this."

Sarah gasped for air as Jake repositioned her facing away from him, on all fours, ass in the air. He braced himself, gripping her hips as slowly slid inside of her.

"You guys make each other cum?" Nick asked. Brent half expected him to comment on Sarah's fluid position change from oral to doggy style, but understood that maybe Nick was really into the moment and had probably seen this video a hundred times before. Brent looked away from the television and caught Nick shamelessly ogling his engorged penis.

"A couple times, I guess." Brent said feeling the heat rise. He imagined Nick's eyes on him. He adjusted his body slightly, giving him an even better view.

"You mind if I take off my shirt? It's kinda getting hot in here." Brent asked.

"Hey man, get butt ass naked if you want. Me casa..."

Brent pulled off his shirt and socks. Nick followed suit. In that moment, Brent realized what he was committed to. Here he was, completely nude with another completely nude guy, of whom he barely knew, watching porn and jacking off together, in a dorm room he had never set foot in before. At that moment it dawned on him that all of his experiences in the last year prepared him for this moment.

He thought back to the first time he and James jacked off together. There was the initial awkwardness that quickly fell away to reveal a world filled with much more rewarding delights. He thought about the first time he watched with awe as James shamelessly spread his legs to show Brent how the muscle behind his balls; his perineum, or taint, pulsed when he came. They spent the night together showing each other how their bodies responded to orgasms and other stimulation. By morning, James' basement smelled like an adult movie theater.

"No oral or anything then?" Nick asked, pulling Brent back to the present.

"Huh?"

"You and your best friend never did oral with each other?"

"Nah." Brent lied. There were certain things he wouldn't freely admit to, he and James trading blowjobs was one of them.

"Man. Sorry if I'm gushing, I'm just really impressed over here and it's been a while."

"It's cool, man. I don't mind. I kinda like showing it off."

"Must be a real ego boost though, huh? Knowing you're the biggest dick in the room." Nick asked.

"I guess. I'm sure I'm not always gonna be the biggest." Brent chuckled. His fingers were wrapped around the base of his thick penis, wagging it obscenely in the air. The veined monstrosity looked like it was heavy. He used his free hand to squeeze up it's length in increments, fully aware that Nick was getting off on the show.