The Jack Off Sessions Ch. 02

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Brent and James continue the fun.
6.7k words
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Part 2 of the 8 part series

Updated 06/09/2023
Created 02/10/2006
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dlake
dlake
123 Followers

The Jack Off Sessions 2: More Adventures of Brent and James

Part 1.

Brent rolled to a stop at the side of the white stucco building. He unwrapped the chain from the frame of his bike and secured it to the empty bike rack. Looking around, he noted how innocuous it all seemed. A partially empty parking lot surrounded by a high fence and a single building sitting in the center. Trees shaded the borders. He concluded that the fence hid the parking lot from the street, giving the patrons of the building a sense of much needed privacy.

He made his way to the side of the building toward the entrance. Black tinted glass hid the interior from prying eyes. A single sign above the door announced the name of the establishment: "Wonderland Adult Books, Videos, Novelties." He pushed the door open and stepped through.

Brent felt the cool air of air conditioning once inside. This was a clear contrast to the hot afternoon he just escaped. His eyes adjusted to the interior lighting and he continued inside.

Passing the bearded employee at the register, he made his way to the video section of the store. Peering over the top of the shelves he got a better look at the patrons. The single employee at the front of the store was flipping through a magazine at the front counter seemingly oblivious to the presence of everyone. A balding man was browsing the large shelves displaying a dozen different varieties of magazines. Two attractive middle aged women giggled as they loitered in the novelties section eyeing a row of different sized dildos and vibrators.

Brent returned his eyes to the video covers, keeping a mental inventory of the explicit images. Asian Sensation 3, Titty Fuckers 7, Anal Adventures 18, Brent's eyes glazed over as he discovered more and more videos he had never seen. Though his experience with porno movies and magazines had grown in the past few months, this was the first time he ever saw such a massive collection in one place. Before long a bulge strained the crotch of his denim jeans.

He casually moved from aisle to aisle taking in all of the images, allowing his arousal to grow. He turned the corner to yet another section of videos before arriving in the novelties section. He met the two women he had seen before head on.

They simultaneously looked down at the growing erection in his jeans and giggled to each other. He felt himself blush, averted his eyes in embarrassment, quickly turned into an aisle of videos and headed for the register.

The register area was set a few feet higher than ground level of the rest of the shop. The counter itself had a glass front displaying a variety of lubes and other small sex novelties on a number of shelves. As Brent approached the man behind the counter the employee put down his magazine and greeted him with a polite smile.

"One of those, please." Brent said in a hushed voice as he pointed to a large bottle of lube on the top shelf of the display case.

The employee bagged the bottle and rung the total up as Brent fumbled money out of his wallet. He could hear the giggling women somewhere behind him. With the transaction completed, the employee slid an anonymous brown paper bag with the bottle of lube inside across the counter toward Brent.

"If you want, you can take care of that in the arcade." The employee said as he gestured to a hallway off to the side of the store near the magazine rack. The doorway had a purple frame with a pink neon "Arcade" sign above it. Beyond the black curtain looked like a dark hallway. Brent was confused, and met the man's eyes.

"What?" Brent mumbled.

The employee gestured to Brent's obvious hard on with a nod then pointed at the doorway.

"There, in the booths."

"Oh, okay. Thanks." Brent replied and headed toward the doorway. He was not quite sure what had just taken place. This was his first experience at an adult bookstore and was not prepared for sensory overload. Porn everywhere, women shopping for dildos, strangers browsing a variety of items for their personal fantasies. His mind raced as he walked under the Arcade sign, passed the curtain and into the darkness.

His eyes slowly adjusted to a dim light as he made several turns down a maze of hallways. He realized that the walls were lined with doors. Some closed, others opened. As he walked deeper inside he peeked behind one to see a small booth with a video screen secured to a wall. A single chair was set in the corner of the booth across from the screen. He quickly realized that these booths were for customers to relieve themselves. He instantly understood what the employee was obliquely referring to.

Brent walked to the end of the hallway and entered a booth in the back corner. He closed and latched the door behind him. Facing the video screen he noted a slot for dollar bills. He fed a five dollar bill into the machine and sat down in the chair as the screen blinked on.

A blonde woman with ample cleavage teased a man's dick to attention. Her tongue ran up his shaft and began to suck the head.

Brent relaxed and looked around the booth. It was no more than 5 feet by 5 feet wide. Small, but comfortable for a single person. The video screen was a 20 inch television set into the wall. To the right of it were a series of well worn buttons.

Brent pressed the buttons and another movie in progress began to play. A brunette with a bob haircut was riding a thick cock with her perfectly formed ass toward the camera. Again and again she lifted herself off the thick erection until only the tip was inserted and lowered herself until it disappeared inside her. She moaned and panted with every pump.

Brent leaned back into the chair and adjusted himself through his jeans. He sat watching the video in a trance for a few moments, tracing the outline of his own cock with his fingers

"Why not?" He thought to himself. He stood up, unzipped his pants and let them drop along with his boxers down to his ankles. He looked down at his throbbing 8 and ½ inch erection and tugged it to it's full length. He sat back down and began slowly stroking to the video on the screen.

As he slid his hand down to the base he reflected on the past few months. He and his best friend James had made a routine of meeting up and watching porn together. Not a single time did they go without stripping down and jacking off in front of each other to completion. The thought of getting off and watching his friend do the same made him rock hard.

He pumped his engorged cock slowly taking in the sex scene occurring on screen. A gasp on his left distracted him. It was then that he finally noticed the circular hole cut into the wall. He was at an angle that did not allow him to see through it but he knew someone was watching him. A length of blonde hair swept past the hole as light from the television screen illuminated the darkness next door.

Brent continued stroking his cock at a measured pace as he stared at the hole. He heard a moan and the sounds of movement but the hole remained unobstructed. The light from the television in the booth revealed that the person who gasped through the hole was no longer looking through it.

He slowly leaned forward and peered inside.

He saw the bodies of a couple pressed tightly together. The woman wore a black skirt and the other figure wore jeans. The second figure's hands slid up the thighs of the girl wearing the skirt hiking up the hem. Fingers curled under the thin fabric of her white cotton panties and pulled them down.

Brent let go of his throbbing cock and leaned further toward the hole to get a better look inside the neighboring booth. Though he could not see far up enough to see the faces of the couple, he got a clear view of the woman's breasts. She wore a tight pink tank top without a bra underneath. Brent noted how big they looked on her thin frame as she played with her nipples through the stretchy fabric. The second figure squeezed her ass under the skirt and Brent caught a scent of wet pussy.

Brent quickly leaned back in his chair as the couple shifted in their small booth. He guessed that they were passionately kissing from the smacking of lips and grunts. With his eyes alternating between the scene taking place on the video screen in front of him and the hole in the wall, he spread his legs and began playing with his smooth balls.

Before long Brent registered two fingers sliding around the edge of the hole. Looking through it he saw the red lips of the woman as she opened her mouth exposing the moist interior. Instinctively Brent stood up, faced the wall and fed his hard cock through. Inch by inch his thick shaft disappeared through the hole. A moment of panic filled his head as he realized just what he was doing before a wet mouth engulfed the engorged member.

He felt the length of his cock slide into the wetness of a mouth, the lips creating a seal around the throbbing shaft. A sucking sensation paired with a slippery tongue relaxed him instantly. Brent looked down at the base of his dick disappearing through the hole in the wall and fed the rest through until he was pressed tightly against it.

The lips broke contact and a hand pumped the slippery shaft. He felt fingers explore every inch. The wet mouth returned and took the length whole. Brent's eyes rolled back and he groaned.

This was his first experience having someone deep throat his entire 8 inches. He was in heaven. Fingers tugged on his heavy balls hanging on the other side of the wall and the sucking mouth slid from the base to the tip and back again. Pressed tightly against the hole he allowed his rod to be serviced by the expert cock sucker.

He imagined that the cocksucker was being fucked by her man. He envisioned her breasts being squeezed, her wet pussy stretching from his hard manhood sliding in and out of her. His thighs slapping her perfect ass with every thrust. With the image in his mind of this horny woman being serviced from behind while deepthroating his hard cock, Brent could delay it no longer.

He grunted and exploded into her mouth. She slid down to the base once again and pressed her lips against his groin. He felt the head of his cock pass down her flexing throat as she drained every drop of cum from his balls. He grunted and groaned until there was nothing left.

Just as quickly as it started, it was over. He heard the neighboring booth door open and close as he was still pressed against the hole. He slid himself out and sat back down. He breathed heavily reflecting on what just happened. The video on the screen blinked off and he was back in darkness. He pulled on his jeans, picked up the brown paper bag, it was time to go.

Part 2.

The red VW Golf was parked in the middle of the driveway. Brent rolled to a stop beside it. A quick look inside revealed nothing significant to give him an idea of who the owner was. A binder of CD's, some receipts stuffed into a cubby hole, a pack of gum on the passenger seat.

Brent leaned his bike against the porch and rang the bell. He looked back at the car thinking to himself who it might belong to. Before he could come up with an answer James answered the door and let Brent though.

"What's up man?" James greeted him wearing a tee shirt and cargo shorts.

"Same old. Who's car?" Brent asked as he stepped out of the summer heat into the air conditioned house.

"Claire's back from school. She's gonna spend the break here at home."

The two walked into the kitchen where James returned to his half finished bowl of cereal. Brent hopped on a bar stool next to him.

"No kidding. Where is she? I haven't seen her in years." Brent asked as he set down the small paper bag he was carrying onto the kitchen counter. The image of a mousy girl entered his mind. He remembered her being cute with short tussled blonde hair. Though they got along during Brent's youth, he never thought of her as anything but the sister to his best friend. She was a bit of a bookworm and always seemed a little too interested in schoolwork than socializing, which suited Brent just fine.

"Speak of the devil." James said gesturing to the hallway leading to the bedrooms. Brent turned his head to say hello to James' sister.

Long tanned legs lead to a short black skirt. A tight pink tank top stretched across full firm breasts. Her short tussled hair had grown out past shoulder length and framed a face fit for modeling. Her blue eyes lit and a smile spread across her face as she saw Brent sitting there in the kitchen watching her with his mouth ajar.

"Oh my God" Brent mumbled as he recognized that this girl, this woman, sister to his best friend, this was the woman behind the glory hole.

Part 3.

"Gonna give me a hug or what?" Claire asked as she trotted toward Brent with her arms stretched. Brent got up and returned her embrace. He could feel her warm breasts pressing against him. He noted that she was wearing a bra, which the woman at the bookstore was not. She must have put it back on after she left the store, in the car, or maybe here in her old bedroom he thought to himself.

"Wow Claire, gone two years and you come back a supermodel." Brent said as they hugged.

"Yeah right. I just filled out a little."

Brent could smell the clean scent of her hair. Her warm body felt good in his, a perfect fit. Brent realized that he might be holding on too tight, so he quickly loosened his embrace and stepped back a bit.

"It's good to see you again."

"You too. By the look of it, you've grown up a lot yourself." She commented with her hands on Brent's shoulders, looking him up and down. "You're practically a man now." She joked.

"Oh funny. At least you haven't lost your sense of humor." He laughed as he sat back down. She sat beside him at the counter.

"So is that your car in the driveway?" He asked while wondering if in fact it was her who he received a blow job from through the glory hole earlier that morning. Same skirt, same tank top. Her build seemed similar, though it was pretty dark in there. He tried to remember if he saw a red Golf in the parking lot. His eyes drifted along her body finally meeting her eyes which responded with a playful look. "Shit, she saw me checking her out." he thought to himself. He looked away.

"Nah, it's my roommate's. I dropped her off at her Aunt's house. I'm supposed to pick her up later." She leaned back on the counter on her elbows, arching her spine as she stretched. A small yawn escaped her lips. Brent's eyes shot back to her breasts which were stretching out her tank top to a dangerous degree, then over to James who was watching him shaking his head with a smirk. "Shit!" He thought to himself again as he refocused to a random spot on a wall across the room.

"Cool." He managed to get out as he got up. He snatched the brown paper bag from the counter and stood with his hands behind his back.

"Well, we'll probably be seeing a lot of each other then. With your parents gone on that cruise, I'll probably be hanging out over here." He watched Claire as she finished her stretch and hopped off the stool.

"Awesome. Well, I have the car so if you need a ride anywhere just give me a holler. I'm gonna take a nap though, I'm beat. You kids stay out of trouble." She joked as she disappeared down the hallway. Brent made a mental note of the way her skirt swayed with every step. He wondered if she was wearing panties.

"Dude." James said.

"What?"

"That's my sister." James clarified.

"I know man, it's just.... Damn! What do they feed them at her school." Brent said as he recalled the morning's adventure and the possibility of having received oral sex from James' sister.

"I know right? Still, she's my sister." He replied, and left it at that.

Part 4.

As the sun set, Brent and James set down the controllers of their game console and leaned back on the couch. James reached into the bowl of chips on the coffee table and ate a few. Brent yawned and switched the TV back to cable with the remote.

"When's your sister coming back?" Brent asked as he flipped through the channels.

"Why?"

"Just wondering. I got that new bottle of lube. So..."

"Shes could be home any second. We'd better wait till later."

"Yeah. So... your sister. Man..."

"I know right? When she came to the door I was like, 'Whoa, who is this?' Of course this was before I realized it was her."

"Don't take this the wrong way, but your sister is fucking hot!"

"Yeah, yeah... she's still my sister."

"Smokin' hot."

"Dude."

"Great ass, thin waist, sexy ass lips. Man, she's superfine!"

"Dude!"

"Just saying, good genes."

"Anyway... where did you get the lube?" James asked.

"Remember that porn store we passed the other day?"

"Yeah, that one in the middle of nowhere?"

"That's the one."

"What's it like?"

"Wall to wall porn videos. There's a section for magazines, a section for toys and stuff. But check this out though, after I bought the lube, the guy at the counter told me I could try it out in this booth section."

"Booth section? What do you mean?"

"Well, there's this doorway marked 'Arcade.' Inside is this maze of hallways with doors on either side. Behind the doors are these small rooms with tv's in them. You put a couple of bucks in a slot and the it plays porn."

"You just stand there and watch it?"

"No, there a chair to sit on. Here's the thing though. I was in there watching a porno when I noticed a hole in the wall."

"Someone was watching you?"

"Yeah!"

"Dude."

"I know right? So I look though and it's this girl in there making out with someone else. I couldn't really see much, but I could tell she had a nice body."

"Awesome. What did you do?"

"I was hard as hell from the movie, now there's this hot piece of ass on the other side of the wall watching me jack off and making out with her boyfriend or whatever. I took off my pants and gave her a show."

"Naturally. Then what?"

"So after a while, she puts her mouth up to the hole and starts licking her lips."

"Hot. Then what?" James asked.

"I stuck my dick through."

"No shit!"

"Yeah dude. It was like... impulse. I had no control over what I was doing."

"What happened?"

"What do you think? She sucked me off."

"Any idea who it was?"

"No clue." Brent lied.

"So did you cum?"

"Yeah. She deepthroated me dude. I was balls deep."

"Whoa."

"I came down her throat. It was awesome. It was like she was milking my cock. My balls were completely drained when she was done. She swallowed every drop"

"Damn dude, that's hot."

"Yeah, you gotta check this place out." Brent said.

A key entered the deadbolt and turned. Claire opened the front door and walked through. Following her was a petite brunette wearing a loose gray hoodie and tight black leggings. Her glasses slid from her face as she struggled to pull her suitcase through the entrance.

James and Brent hopped off the couch to help with the luggage.

"What gentlemen." Claire said smiling in the doorway.

"Looks like you could use some help." Brent said taking the dufflebag from her arms. He was surprised at the eye contact she was making at him. It almost seemed that she was flirting. He blushed.

"I'm James, this is Brent." James said, introducing them to the new girl.

"This is Allison, my roommate from school." Claire said as she walked to the kitchen.

"Hey." Allison said.

James took her luggage and backpack and brought them inside.

"Claire told me so much about you guys. I feel like I already know you." Allison smiled as she stepped in the foyer. She brushed her bangs from her face and adjusted her glasses. Her clear green eyes looked from James to Brent. She was shorter than Claire and though her sweater was loose, it was obvious that her breasts were much larger.

"Can you take those up to my room?" Claire shouted from the kitchen.

dlake
dlake
123 Followers
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