The Jack Off Sessions Ch. 03

Part 1. James in Wonderland

James sat in the dark booth. It was just as Brent had described it. Small, but with enough room for a single person to sit comfortably. The television was set into the wall, a series of buttons were arranged to the right, below the slot for dollar bills. The distinct smell of semen lingered in the air.

He fed it a few dollars and watched as the screen blinked awake. The redhead arched her back as a man slid his cock deep in her wet pussy. She cooed with pleasure with every pump.

Earlier that morning James woke up before sunrise. He laid in bed awake after a quick stop to the restroom. Brent was sound asleep on the carpet. He was wrapped in his sleeping bag, head on his pillow, breathing silently. James casually stroked his growing erection through the thin fabric of his boxers. He sighed and tried to fall back asleep.

Before long, his dick was rock hard. His shirt was off, his boxers were tangled in the lump of blankets kicked to the foot of his bed. James looked down at his engorged penis and groaned quietly as he squeezed it. He turned his head toward Brent to see if he was still sleeping. He was.

James had been thinking about what took place at the adult bookstore the day prior. Brent had told him about how he received an amazing blowjob through a gloryhole while shopping for lube. James imagined Brent standing in that dark room, looking down as he fed his thick cock through the mysterious hole where a wet mouth was patiently waiting.

He pictured the satisfaction of the person on the other side as Brent's massive engorged penis squeezed through the hole. His mind wandered back into Brent's perspective as he felt the stranger's soft lips slide over his erection. His hand slid over his own throbbing cock as his imagination played out the scene in his head.

Within moments, James's curiosity about this bookstore, and the potential of their gloryholes, got the best of him. He stuffed his dick into a pair of shorts, pulled on a tee shirt, and grabbed a sweater. He closed the door softly behind him as he snuck out of the house and onto his bike.

The ride there was tinged with the erotic promise of finding unknown sexual ecstasy. The cool morning air rushed past his face, caressing his body through the fabric of his clothes. Before long, he was inside the store, walking under the "arcade" sign and into a booth with a glory hole.

James sat in the dark booth alternating his attention from the movie to the hole in the wall. He wondered if this was the one that Brent used. After a while he looked through it and saw a dark void.

He got up, opened the door, and peered into the hallway. It was empty. He walked around and looked through the other doors only to find identical arrangements in each one. Chair in corner, tv in wall. Some had glory holes, but most did not. All of them empty like the first.

Disappointed but somewhat relieved, He wandered back into the main area of the store. He was looking at a shelf of magazines near the register when the cashier spoke up.

"Pretty dead in there right now."

"Yeah." James mumbled.

"You should check the theater." The man said.

"Huh?"

The man nodded his head to another door along the wall. 'Theater' in purple neon hung over a black door. He did not take his eyes off his magazine for even a moment.

"It's usually $10 to get in. But I'll let you check it out for free." He offered.

"Oh. Okay, thanks." Brent replied.

The man was again lost in the magazine he was reading. It was if no words were exchanged at all. James walked through the doorway.

He quickly found a seat. As his eyes adjusted to the low light, he realized that he was not alone in the dark theater. Toward the front, two men in separate rows sat fixated on the screen. To his right, several seats down, a middle aged man claimed the spot at the end. Behind him, in the back row, two figures were side by side, hidden in the shadows.

James looked over to the man on his right. He was moving his hand in a familiar motion. James quickly realized that he was openly jacking off.

Taking this as a positive sign, James pulled down his shorts, releasing his own erection. His cock was a little over 7 ½ inches long, thick, and smooth. He preferred shaving off all his pubic hair. Nothing beat the feeling of skin on skin, he felt.

The man to his right leaned over and said something to James, but he could not hear it over the audio from the movie. James shrugged his shoulders and pointed at his ear, indicating that he could not hear him. The man moved down the aisle and took the seat next to him. He repeated his sentence.

"Nice cock."

"Thanks." James mumbled, not sure what the normal course of action is in these kinds of situations. His best friend Brent was the only other guy he had ever done anything even remotely sexual with. Even then, they had known each other since childhood. Their current situation of meeting up to watch porn and jack off together had been a strictly hands off affair.

James continued to stroke with the man's eyes glued to his cock. He tried to ignore him and watch the movie, but he could not help but feel the intangible warmth of the mans gaze. His erection was rock hard and precum leaked from the tip. He worked it into the shaft as he pumped.

James looked over to the man's own rhythmic motion. In comparison, James looked huge. Not to say the man was small, his dick was roughly an inch shorter than James's. However, the girth of James's erection made it look much much bigger. Thick and hard, James stroked his engorged cock.

"Mmmm, it's so big." The man moaned.

James remained silent. He focused on the screen. He was afraid of what he might see if he made eye contact with the man. He found it funny that this is what it must like for Brent when jacking off with James.

"Can I touch it?" The man suddenly asked.

James looked back at him. The man's eyes never left his crotch. The look on his face was one of hunger, his own cock leaking precum. James imagined that maybe this was what he had ultimately wanted the whole time.

All those jack off sessions watching Brent stroke, fantasizing about it, wondering if it would ever go further. Now, here in this place, a stranger wants to cross that line, touch his cock, feel it's hardness and warmth. James moved his hand away and flexed. His cock stood at full attention.

The man reached over and slid his palm over the underside. James closed his eyes and leaned his head back. The man's hands were warm and soft. Not as soft as a girl's hand, James thought, but soft enough. He opened his eyes and looked to the scene on the theater screen. The soft ass of a curvacious woman slid down to the base of a gleaming cock. Her juices coated the whole region leaving it shiny and wet looking. His balls bounced as she rode him.

The man gently wrapped his fingers around James's shaft and began stoking. His grip increased and so did his speed. James looked down and saw an good amount of precum leaking like never before. The clear sticky liquid rolled over the man's knuckles.

"Can I suck it?" He asked.

"I don't know..." James mumbled

"I'm really good." The man pleaded

"I've never... really... done this before." James explained.

"Really?" He asked.

"Yeah."

"That's so hot." He moaned.

James did not reply.

The man stopped. James looked at him. The man smiled.

"You want me to continue." He asked.

"Yeah."

"Tell me."

"What?" James asked.

"Tell me what you want me to do." He said. James looked at the man confused. He realized that what he was about to ask was harder to get out than he thought.

"I want you to jack me off." He whispered.

The man looked at him silently, smiling softly.

"Jack me off, make me cum." James finally said.

The man resumed jacking him off slowly. James watched the man intently work his erection. Masterfully, the man applied just the right amount of pressure in the right places. He seemed to know exactly what James liked.

"Faster." James whispered.

The man quickened his pace. James felt the familiar sensation in his core. The warmth and tingling in his crotch increased.

"Unh..." James groaned as he came hard on the back of the seat in front of him. Powerful bursts of thick cum splashed the black plastic, dripping into the floor into a puddle. Several ropes landed on his thigh. The man slowed his pace, squeezing on the upstroke, working it all out. James panted and melted into the seat. He was spent.

He looked over to the man. He watched him lick the cum off his hand. He scooped up what landed on James's thigh, lubricated his own erection and began masturbating with it. James was amazed at the overt kinkiness of the man's actions. As he greased his hard cock with cum and brought himself to orgasm, James became aroused again.

Part 2. Voyeurs.

The hot spray of water washed over Brent's naked body. He wiped the steam from the small window and looked down at the pool. Only moments after stepping into the shower, he noticed the girls sunbathing in the backyard. Claire and Allison, James's sister and her college roommate took turns spreading suntan lotion on each others shoulders.

Earlier that morning he woke up to a surprise blowjob from Allison while Claire made out with him. The two apparently teamed up to ensure that they could take advantage of him as efficiently as possible with the least amount of struggle. Not that he would have put of a fight. In fact, he would have gladly participated in their little game if he only knew he was going to be a participant.

Claire, out of the picture while away in college, arrived back in town the day before. James, nor Brent, had any idea that she would be spending her vacation back home. It was a nice surprise, at least to Brent, to see her again. His memory of the mousy sister to his best friend was replaced with the very sexy woman in the tiny black bikini that now dangled her feet into the pool.

She was gorgeous. Her naturally blonde hair hung just past her shoulders. Her blue eyes sparkled with a constant playfulness that drove men wild. She had the body of a playmate. Tall, athletic, and toned. She was the definition of a hard-body.

Next to her, laying on a towel was Allison in an even smaller white bikini. Unlike Claire, she was very petite. At least a half a foot shorter, she would seem tiny if not for her large breasts. It was almost distracting how voluptuous she was. Her hourglass shape seemed almost constructed by the imagination of a teenage boy. Her dark hair, dark eyes, and mysterious history made her even more attractive.

Together they could stop a stop a room full of men in their tracks without uttering a single word. Between these two beautiful women with amazingly fit bodies, was the ideal sexual partner, fulfilling the desires of most heterosexual men. Brent could hardly believe that he was lucky enough not only to be around them, but to have had an increasingly kinky, sudden, and secret sexual relationship with both.

Stranding under the hot shower, looking out of the window, Brent stroked his engorged 8 ½ inch penis. He slid his hand from the head down to the base fantasizing about being with both of them. He pictured Claire laying before him, legs spread, pussy wet, nipples hard, begging to be filled by his massive cock.

He imagined Allison, sucking on his lips, her breasts pressing hard against him, her hands exploring his body. He pictured her bending over, arching her back and lifting her perfect ass in the air. He massaged his balls while filling his head with every dirty thought he could with these two goddesses as the inspiration.

He groaned with pleasure. His eyes were closed. He felt like he was getting close to cumming. He was suddenly interrupted by a knock on the door. He was jolted back into reality.

"Hey, don't use all the hot water, k?" A girl's voice called out from behind the locked door. He looked out of the window and saw Allison laying there alone. It must Claire out there, he thought to himself.

He quickly turned the knob, shutting off the water. He grabbed the towel hanging from the rack and wrapped it around his waist. Looking down, it was obvious he was hard. If Claire was indeed still standing in the doorway, she would get a show.

He pulled the door open expecting Claire to be standing there in her little black bikini, a naughty smile on her face. He was disappointed to find an empty hallway. He looked left, right, he was indeed alone. He stepped into James's room and closed the door behind him.

James pulled his bike into the driveway, leaned it against the wall by the front door, and quietly inserted his key into the lock. The smell of cooking bacon and scrambled eggs greeted him. He gently closed the door behind him and silently worked his way upstairs trying to remain unnoticed.

He pushed his bedroom door open to find Brent standing at the window, back to the door, seemingly fixated on something outside. Having grown up with him, James could spot him in a crowd within seconds. At this moment however, Brent stood completely nude.

A thin layer of moisture coated his body in some parts more than others. His hair was wet, droplets of water landed on his broad shoulders, a damp towel hung on the arm of James's bed frame. The scent of shampoo and body wash was thick in the air. James deducted that Brent must have just gotten out of the shower. Apparently, something outside distracted him before he could finish drying.

Though James had seen Brent in all states of undress over the years, especially lately now that their jack off sessions had become an almost daily event, never had he seemed so on display this morning. His strong legs, a result of a passion with track and field since freshman year, were planted firmly on the soft carpeted floor. His muscular ass tightened with every small thrust of his hips. His thin waist tapered up slightly to broad shoulders. Although he was faced away, James imagined the look of ecstasy that he was so familiar with seeing.

He recognized the familiar rhythmic motion of his right arm, the soft, almost inaudible, grunts and moans escaping his lips. No doubt, Brent was masturbating. Whatever had his attention allowed James to enter the room completely undetected. He would have laughed if he was not so turned on by it.

After studying Brent's physique for a few more moments, he snapped back into reality. He shut the door with enough force to announce his arrival but still seem natural. Startled, Brent spun around, his thick penis stood at full attention, his hand still wrapped around it. The look on Brent's face was priceless and James could not help but to laugh.

"What's up?" James smiled as he tossed his sweater on the bed. He casually made his way next to Brent to the to see the attraction out of the window.

"Fuck man! You scared the hell outta me." Brent let go of his erection allowing it to slap his abs with some force. He wiped his face with his hands, feeling the moisture from the recent shower still fresh on his skin. He brushed the wet hair from his forehead and looked at James. "I didn't even hear you come in."

"Sorry bro. You didn't lock the door, I didn't think I'd walk in on you beating your meat the first thing in the morning." James laughed.

"Dude, look out there. You'll see..." Brent said motioning out of the window. Noting the hardness that seemed to petrify the magnificent specimen of manhood jutting from Brent's crotch, James knew he was in for a treat. Indeed he was.

James's mother always prided herself on her house. Most importantly, her yard. Immaculately groomed, perfectly planned, every leaf, every blade of grass seemed placed by hand. The backyard was no exception. The crown jewel was the pool. At this moment, all of the effort seemed worth it in order to frame the perfect figures of Claire and Allison laying by the cool blue water.

Growing up, Brent was used to being around Claire. James was his best friend and naturally Claire found her way in the picture every so often. She was older than them, but always had a good sense of humor about things. He actually liked her, unlike most of the sisters of his other friends.

Though they never hung out exclusively, they shared a love for books and often found themselves in deep conversations about the plight of one protagonist or another when he came over. As he grew up, he realized that she was actually very pretty behind the glasses and frumpy clothes. However, as his best friend's sister, he dismissed her as nothing more.

Now however, she had blossomed into a knockout. The glasses were gone, replaced by contacts. The frumpy outfits tossed in favor of more flattering attire. Her skinny frame was now complimented by curvy hips, bubble butt, and full breasts. Apparently college provided her with the right atmosphere to loosen up. It seemed that she was now well aware of how attractive she was and found nothing wrong with a little advertising.

Allison, on the other hand was still a bit of a question mark. He knew that she was Claire's roommate from college. They had become close over their time together and considered each other best friends. She grew up not far from them and actually knew some of the same people. Other than that, she was a blank slate.

Claire and Allison sunbathed by the pool. The girls compared tan lines, seemingly oblivious to their secret audience. Before long, they both had their tops off, and spread suntan lotion over the previously unexposed parts of their body.

"Seriously?" James gasped.

"I know, right?" Brent added.

Side by side the guys stood at the window and looked down at them. James wore shorts and a tee shirt, Brent was completely nude. He intently stroked his cock.

"So where'd you go this morning? You weren't here when I got up." Brent asked without looking away from the window.

"Oh man, I woke up to use the bathroom and couldn't fall back asleep." James replied.

"And?"

"So I was laying in bed and I started thinking about what you told me yesterday. You know, about the adult bookstore?"

"Yeah?"

"Yeah."

Brent paused.

"You went there huh?" Brent laughed. "Dude, you are so predictable." He playfully punched James in the arm with his free hand.

"Dude, I was horny! I had to see it for myself." James laughed.

"So, how did it go?" Brent asked.

"I went there pretty early. It was dead. Nobody in the store part, nobody in the arcade."

"Oh man, that sucks. What did you do then, leave?"

"Nope. The guy at the register let me check out the theater for free."

"I didn't know they even had a theater."

"Yeah. It was small, but the movie was good."

"Awesome. God, look at her. So perfect." Brent said. Claire had turned over. His rhythm had sped up in direct correlation to his level of arousal.

"She has a perfect fucking body." James added.

Brent was not sure if he was talking about his sister or Allison. Either way, it turned him on sharing this moment with his best friend.

They silently watched for a while. Brent continued jacking off while James observed. His attention shifted between Brent's large cock and the girls by the pool.

"Dude, so in the theater..." James continued.

"Yeah?"

"I was jacking off when this guy sat next to me."

"And?"

"He was just, like, watching me." James was studying Brent's dick at that moment. He looked up and caught Brent looking at him. He could just barely see a smirk on his face.

"So, a guy watched you jack off. We jack off together all the time. Big deal."

"Well, he asked me if he could touch it."

"You let him?"

"Yeah." James was embarrassed. He was afraid that Brent might see James in a different light if he knew the truth.

"He jacked you off?" Brent asked.

"Yeah." He admitted.