The Jack Off Sessions Ch. 08

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Ass

Hello readers and potential readers.

This is an off and on project I’ve been working on for some time. To summarize, it’s the story of two best friends named Brent and James that discover masturbation together in high-school. Over the course of several stories, we are introduced to a handful of other characters that make their way into their journey of sexual exploration. At this point in the story, Brent and James are apart in their respective colleges and find themselves pushing their sexual limitations and indulging in their curiosity. If that kind of thing appeals to you, I hope you enjoy this entry.

***

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 erotik hikaye 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 porno hikayeleri 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 sex hikaye 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.

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