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The Jack Off Sessions 8

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By stiffpoles [Ignore] 21,Aug,21 06:04   Pageviews: 402

Part 1

Brent took the cool air of the early morning into his lungs as he reflected on the current state of his college life. His grades were holding steady with a little wiggle room here and there. The extra credit projects that he treated as required assignments made his packed schedule bearable. All in all, everything had been going positively, without a hiccup: nice and boring. He was keeping his head down and as winter arrived it was looking like he would continue along this trajectory until spring. Unfortunately, a surprise visit from a dorm mate from down the hall introduced some potentially complicated obstacles.

In his small dorm room the previous night, Lucy pulled up a popular porn site on his laptop and played an amateur movie in which Brent partook in group sex. There was no denying it was it him. He couldn't deny it. His best friend's sister and her college roommate took turns using every trick they knew in order to coax him to orgasm using nothing but their hands and mouths. After about ten minutes of well lit video and in front of the lens of a steady camera man, they succeeded. Now, it was available for the world to see and Lucy knew about it.

Brent was expecting the worst, but Lucy had other ideas. As if it was a story he might have read in an issue of a Penthouse magazine in his dad's ancient collection, she wanted nothing more than to satisfy her uncontrollable sexual desires with him as her instrument. It was quick but enjoyable. Afterwords, she insinuated that this arrangement would need to be available in perpetuity in order for her to keep his secret.

He supposed a number of obvious factors would have made this a punishment. Luckily, the only real downside was timing. Brent found Lucy incredibly sexy and couldn't risk his secret to become public, and he had no objections to either point. She was just down the hall, so there was a convenience factor. However, she was practically a stranger to him and he wasn't sure she would be able to keep this secret, or any secret in general. For all he knew, she was telling every person that crossed her path that she personally knew the star of a leaked amateur porno movie.

A vibration in his pocket snapped him back to reality. He pulled out his phone and read the awaiting text message which indicated that the class he was currently headed to was cancelled. His morning had suddenly become free. He turned on the spot and headed back to his dorm. He hoped Lucy would be there. He needed to talk to her. He thought about every scenario as he made his way across campus under a honey colored canopy of trees, almost oblivious to everything around him.

While lost in thought, Brent climbed the concrete steps and pushed though the front doors of his dorm. He took the elevator up to his floor and found it quiet, everyone seemingly away at class or running errands elsewhere. He walked down the hall and debated knocking on Lucy's door, but he would be at a loss for words if her roommate answered. He heard nothing on the other side, so he went back to his room. He sat for a bit and turned on the television in a futile attempt to let daytime programming distract him. Before long, the grumbling in his stomach became too hard to ignore so he headed down to the cafeteria to find something to eat.

The large cafeteria was filled with the scent of every possible variation of breakfast items all at the same time. Depending on one's level of hunger, it could smell quite good. In Bren't current state, it smelled intoxicating. He loaded his tray with as much as he could fit and stepped out of the serving area to see Nick flagging him down.

In that moment, Brent remembered Nick catching him the night prior as he dried off post-shower masturbation session. The following event with Lucy almost completely erased the memory of their brief encounter. At the moment, Nick didn't appear as if he was very embarrassed by it, maybe a bit shocked but not quite embarrassed. Brent's natural inclination would be to quickly find an exit but thought back to his conversation with James and decided to stick around. If he was lucky, he might find out if Nick was in fact Lucy's source for the leaked video.

"Hey man, sorry for last night." Nick apologized after Brent sat down at an empty chair across from him.

"It's cool, man. No biggie." Brent replied as he settled in.

"It was late, I had my headphones in, I didn't even think anyone else was in there." Nick awkwardly explained.

"Yeah, I thought I was alone too. I usually come back after midnight and have the place to myself."

They each took sips from their drinks. The clinks of metal utensils on porcelain, hushed conversations, and inoffensive pop music from the speakers filled the air.

"So, what's your major?" Nick finally asked. His attempt to break the ice to relieve some of the tension was welcome.

"I dunno. I was thinking business, but I'm not sure." Brent explained. He wished he had more to contribute to conversations about his major, but he really had no clue. At this point, he was just happy to have the chance to explore his options. Whether it be Business, History, or something he didn't even realize he enjoyed yet: he was open to all possibilities. Hopefully, it would become clear to him sooner than later.

"I'm undeclared, too. I figure I'll have to decide by the end of next semester maybe." Nick said.

"Yeah, I hear you. So, how long have you been here?" Brent asked, referring to the off campus dorm in which they both resided.

"About three semesters so far. Thinking about maybe getting my own apartment in the summer, but I dunno." Nick replied while pushing food around his plate.

"Cool. Did you know the guy that had my room before me?" Brent asked. This wasn't a topic he ever thought about too much really, but figured Nick might be able to fill in some lingering questions considering his time here.

During his first week in the room, he discovered the air conditioning vent cover by his desk was removable and inside was a couple of relatively current porno magazines hidden inside, which he gladly added to the small collection of explicit contraband that he himself stashed away in the unused luggage deep in his closet.

"Yeah, actually. A guy named Jeff. He transferred last semester." Nick replied.

"Cool, you knew him?"

"Yeah... Jeff and I... kinda had a thing for a while." Nick said timidly.

Brent raised his eyebrows at this. Homosexuality wasn't a big issue for him and he anticipated that he'd eventually meet some gay people in college, he was just caught off guard at how casual Nick was about it. From external appearances, Nick appeared to be straight or at least nothing stood out about his appearance to indicate he might lean one way or the other. There was nothing obvious about his sexuality, but Brent supposed that was the case for most people. He felt a twinge of curiosity at meeting and possibly becoming friends with someone completely out of the closet.

"We kinda dated when I got here. It didn't last, obviously" Nick explained.

"Ah." Brent said, not really sure how to respond.

"I hope that doesn't bother you?" Nick asked.

"What? The gay thing?"

"Yeah."

"Nah. It's cool with me. You liking guys doesn't change me liking girls, so go for it. More power to you. If you're happy, I'm happy for you." Brent answered honestly. In his limited sexual experience, Brent and his best friend James experimented a bit, but he still considered himself heterosexual. Looking back on it all, he framed it as being opened minded. He wanted to maintain a nonjudgemental perspective and let things fall where they may. He understood, out of context, some of the things he had done in his own past might be considered sexually questionable, but that didn't weigh too heavily on his mind. His friendship with James was as strong as ever and their sexual escapades did not diminish it one bit. If anything, it brought them closer together. From his perspective, life was a series of experiences and he was just living.

"Okay... cool. It's all pretty new for me, really. I figure this is college, right? I might as well experiment while I have the chance. Maybe I'm bi, maybe I'll decide I'm straight after all, maybe... who knows? I dunno..." Nick trailed off. He looked at Brent, his plate, around the room, and back at Brent.

"My friend back home said that to me too." Brent said.

"Says what?"

"College experimenting stuff."

"He said you should experiment?" Nick asked.

"Well, he was saying how college is the perfect time to try new things since we'll have opportunities during this time in our lives that we might not have later in life. Yadda yadda yadda, stay open minded. Stuff like that." Brent paraphrased James, thinking about the conversation they had the night before. He couldn't help but to see Nick physically relax before his eyes.

"I'm gonna have to agree with that" Nick chuckled.

A gaggle of girls walked past their table, smiling friendly greetings to both. Brent and Nick returned their smiles and watched them walk by, appreciating the view.

"Right?" Nick laughed. "I swear, being here is gonna give me blue balls."

"Yeah, hotties everywhere. I'm not really sure how I've avoided constantly walking into walls or fallen down a staircase yet."

"No kidding. See that girl over there? The brunette with the pink top?" Nick gestured to a pretty brunette sitting with a gaggle of similarly dressed girls. He continued, "That's Sarah. She went to my high school. Cheerleader, popular, probably one of the prettiest girls in my town. Here, she's just another hot girl. One of, I dunno, a half dozen sitting in in this cafeteria right now."

"If I were a playboy scout, I know where I'd come first." Brent laughed.

"Seriously." Nick agreed.

Brent noticed the way Sarah's tee shirt hugged her chest, her thin waist, the way her lips moved when she talked. She twirled her hair in her fingers as she spoke. She briefly made eye contact with Brent before quickly looking away.

Nick saw Brent appreciating her and smiled.

"She looks as good as you're imagining." Nick said.

"Hey man, I thought you played for the other team?" Brent asked.

"I'm still into girls, too. Maybe I'm just bi. I dunno. She's hot. You can't deny that. Even I can see that."

"She is pretty fucking hot."

"Yeah, no doubt..." They both snuck looks as they ate their food in comfortable silence.

"So, there was a little scandal back at my school with her, actually..." Nick said after a few moments, trailing off.

"Yeah, what kind of scandal?" Brent asked as he leaned in conspiratorially.

"Well, check this out." Nick leaned in. "Sarah's been a 'good girl' for most of her life. I've been going to school with her since second grade and she's always been pretty drama free for as long as I can remember. Well, I guess you could say she cut loose her senior year. She went from clean cut and predictable to... I dunno, unpredictable, wild girl I guess. She started dressing different, sexier, hanging out with a different group of people, and started seeing this notorious dickhead that happened to be one of my brother's best friends."

"No kidding?" Brent asked, getting a good eye full of her and putting his imagination to work.

"Yeah. He used to make videos..."

"Videos?" Brent asked. He imagined what she would look with her clothes off, on her back and her knees pulled up by her head. He tried to shake the thought before he started to drool.

"Oh yeah, I saw them. There were a bunch."

"She looks... so innocent." Brent mumbled. He imagined her on her knees with her mouth open. Her wet tongue presented to him as he pressed the head of his cock into her mouth.

"She was for most of the time I went to school with her. She just went crazy during her senior year of high school, I guess. When I got here, I saw she's back to her 'good girl' persona. As far as I'm aware, I'm the only one around here who knows."

"Coulda' fooled me. I knew a girl back in high school that kinda had that dual persona thing going on. You'd never guess what she got into unless you were part of it." Brent's focus started to shift to a half a year prior to his senior year in High School.

In a flash, Jennie Connor filled his mind. He remembered how annoyed she made him feel when they were very young as she insisted on following him everywhere like an unwanted sidekick. A decade later and he could not stop thinking about her in ways that made him blush. Moving across the country for college was a little known attempt at separating from her with enough distance between them to get his mind right. He paused on the smile she gave him after they simultaneously orgasmed for the first time, then he pushed it all out of his head as best he could.

He wondered if Nick would bring up the porno that Lucy showed him.

"I some saved onto a flash drive, actually." Nick leaned in toward Brent conspiratorially.

"One of the videos? Of her?" Brent gestured with a nod of his head in her direction. A flash drive, he said. Brent wondered if his video was on that same flash drive.

"Yeah man. If you can keep a secret, I can show you." Nick offered.

"No shit? Hell yeah. I'm a steel vault, man." Brent imagined Nick having a whoopsidaisies and accidentally playing his video instead of Sarah's, suddenly realizing Brent is the actor on the screen. What a coinkydink that would be. 'Is that you, Brent?!? Oh my.'

"Yeah? Okay, cool." Nick said.

***

James weaved his bike through the maze of treelined suburban streets on autopilot. Having spent most of his life navigating
these roads, he could safely point his way toward almost any destination within the city limits and spend the ride lost in thought until he arrived. This morning his mind was on sex. Specifically, he was thinking about the evening he spent at his classmate Sam's apartment the night prior indulging in porno movies and masturbation.

He was surprised at how events so easily unfolded the way they did. The night began innocently enough as they worked on a school project together. An unpredictable discovery of Sam's porn collection in addition to a couple of beers and a little marijuana lowered inhibitions enough that they soon found themselves sharing a bottle of lube and jacking off together. The memory excited James enough to make pedaling uncomfortable due to his growing erection. His ringing phone broke his train of thought.

"Hey Sam, what's up?" James answered the phone. He expected Sam to call, just not so soon.

"Hey bro, what are you up to?" Sam asked.

"Nothing much man. Picked up my paycheck, just headed home now."

"Cool, cool. So check it out, man. Remember what we talked about yesterday?"

"Uh, we talked about a lot of stuff."

"Yeah, I mean about the group stuff. Gangbangs."

"Ah, yeah. What about it?"

"Well, when we talked about it, you said you might be down."

"Yeah, man. I'm totally down."

"Yeah?"

"Yeah man. Just let me know."

"What are you doing today?"

"I'll be home in like five minutes. I have nothing planned."

"Alright cool. You think you could be ready in maybe thirty minutes?"

"For sure, man. I'll take a quick shower and get ready."

"Awesome. Gimme your address, I'll pick you up in thirty."

Part 2

As promised, James took a quick but thorough shower. The whole while, he could not help but to think about what Sam had planned for him. Was he really arranging a gangbang? If so, with whom? How many people will be there? The thoughts filled his head as he dried off and got dressed. He looked down at his erection and fought the urge to 'clear the pipes.' Luckily Sam arrived in time to prevent James from giving in as he usually did.

James made his way out of his house into Sam's obnoxiously souped up sports car. They pulled out onto the road as soon as the door was closed. James had a dozen questions, but couldn't think of the first one to ask.

"So, check it out. This lady we're gonna see today is my friend's wife." Sam said casually, keeping his eyes on the road.

"Really?"

"Yeah. They have this... open relationship deal. Well, he likes to watch her get banged out."

"No shit?"

"That's how I met them actually. They were looking for a third. I was a good fit. We hit it off and here we are."

"He's gonna be there?"

"Ah, well... no. This is kind of a side thing for her."

"He doesn't know were going there today?"

"No way. It's one thing if he's there to watch. It's another thing if he finds out what she's up to when he's not around. So, you know... discretion is key here. You good with that?"

"Yeah, no prob. My lips are sealed."

"It's funny. I'm able to afford my apartment because my buddy splits it with me. They live together, right? A nice quiet suburban couple living in a nice little suburban house in a nice anonymous suburban neighborhood. Well, turns out they aren't exactly as wholesome as they seem. He's a pussy hound like me and she's a complete nympho. Anyway, he hits me up on the side one day saying he wanted a place on the down low to bang out his side chicks. So, we get this place together. It's in my name, he just gives me cash every month to keep a room ready for him.

"Nice."

"Yeah. It works out for everyone. He has a place to bring the girls he meets and she gets dick on demand from me. As long as I keep my mouth shut, everyone wins."

"Sounds like a good deal."

"Yeah, I don't feel too bad about it. She's hot as fuck too. You'll see."

"Nice, man. So, it's gonna be us two and her?"

"Yeah, bro. We're gonna tag team her."

The information was coming hard and fast. James felt his head swim with every piece of new information presented . He wasn't a complete stranger to group sex, but his only experiences involved his sister, her roommate, and his best friend. This would be the first time he'd be engaging in a threesome with someone he barely knew, let alone a stranger. The prospect made him nervous, anxious, but mostly excited.

Sam pulled his car into the driveway of an upscale McMansion. The landscaping was manicured just so. A Range Rover was parked in the driveway. In the front entrance stood a pretty blonde. She looked to be in her late 20's to early 30's. She wore a simple sundress that hugged her curves enough to erase all doubt that she was anything but a frumpy housewife.

She casually took a bite of avocado toast as she lead them inside. Sam smirked at James and raised his eyebrows as they followed her toward the living room. James could make out her plump but firm ass beneath the sheer material of the dress. Her hips were narrow and her bare arms were toned and well tanned. The look she gave him over her shoulder instantly gave him stand at attention.

The ceilings were high. The décor was tasteful, if not borderline extravagant. James noted the large flatscreen television hanging over the fireplace was much larger than he had ever seen. When his eyes made their way back to Christine, she was half sitting on the back of an overstuffed white leather couch looking him up and down. He suddenly felt like she was a predator and he was her prey. He audibly gulped.

"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.

"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.

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Comments:
By #339203 [Ignore] 21,Aug,21 16:13
Mate.. your stories keep getting hotter & hotter.. I'm so hard right now
Reply
By stiffpoles [Ignore] 21,Aug,21 17:40
Good...knowing I made some other dicks hard makes me feel amazing!
By #339203 [Ignore] 21,Aug,21 20:48
So much so bud.. after reading your story, i woke my GF sleeping next to me. (she asked what time it was.. i told her it's Sex AM) We had slow hard sex resulting in an almost euphoric amaze-balls orgasm.. was hard for so long afterwards and we both dozed off to sleep again, me deep inside her.. Thanks again hey
By stiffpoles [Ignore] 22,Aug,21 05:40
That's fucking hot! You need to write that down or record it I wanna see
By #339203 [Ignore] 22,Aug,21 05:58
Hahaha Nah man.. (i keep my partner's bits private, male or female - if that's what they want.. you follow?) On the plus + She's brought me home, out of the blue, two cases of beer and four bottles of red wine, and she doesn't even drink!!.. (i must've done a fairly decent job in her eyes) Love your stories bud, will be waiting for the next installment


By rikki [Ignore] 21,Aug,21 22:00
wow... your episodes are getting more lascivious...
Reply
By stiffpoles [Ignore] 22,Aug,21 05:44
Hopefully, it was steadily progressive from beginning to now, as intended And BTW awesome opportunity to use the word of the day: "Lascivious" I haven't heard that used in quite some time. Anyway,


By furluvr [Ignore] 21,Aug,21 11:34
Aw, hell yeah, man!
Reply
By stiffpoles [Ignore] 21,Aug,21 17:40
Glad ya like it!


By #552884 [Ignore] 21,Aug,21 17:32
Hell yeah these are just so freaking awesome Josh, Great work as always mate
Reply
By stiffpoles [Ignore] 21,Aug,21 17:39
Thanks Scoob! I always looking forward to your comments on my blog!


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