The Jack Off Sessions Ch. 05

The Jack Off Sessions Ch. 05: Brent and James have a guest.

Brent and James sat side by side on the small couch in the dark basement. The blush of light from the television illuminated their nude bodies. The image on the screen was graphic. Sweating bodies gyrated, lips sucked, tongues licked, breasts bounced, hard cocks slipped in and out of wet pussies and open mouths. The two, in the privacy of their secret clearing, stroked their well lubricated erections at a steady pace, completely ignoring the television, watching as the girl disrobed in front of them.

Part 1.

Earlier.

The hot summer sun was reason enough for the girls to wear their bikinis throughout the afternoon. At the grill, Brent flipped burger patties with Claire at his side, sitting on the tabletop a foot away. She explained what classes she was taking in college and what life was like in the dorms as he listened intently. In the water, James and Allison floated on the surface, chatting about television.

It was a nice day.

"Well, I liked it." Allison said, slowly paddling her hands in the cool water. She wore a small white bikini that barely fit. With such a petite frame, her body seemed almost exaggerated. Her large natural breasts jiggled with every movement. Her thin waist flared out to very feminine hips. Her bare feet dangled in the water. Like James, she lounged in a floating pool chair wearing sunglasses, enjoying the warm sun.

"Yeah. I mean, it was good, but I was expecting a little more. They left a 'lotta loose ends." James replied. Through his tinted lenses he studied Allison's body. He found it hard to maintain his concentration on the conversation with his erection throbbing beneath the thin material of his swimming trunks. It was all he could do from reaching down and squeezing his aching cock to relieve some of the pressure.

"That's what I liked about it. Those loose ends... I dunno, it give it some life after the end. Ya know?" Allison answered, adjusting the strap of her bikini top. She watched James as he struggled to ignore the tent in his shorts. She stifled a smile and brushed imaginary lint from her breasts, her nipples stiffening with contact. She almost laughed as James's mouth fell open. It was almost cartoonish, in a cute way.

"Food's ready." Claire announced, hopping to her feet. Standing next to Brent, she found herself incredibly attracted to him. Aside from the obvious physical chemistry, she found him incredibly charming and sweet. He genuinely seemed interested in her, which was a change of pace from the guys she normally found herself paired up with. However, his almost platonic attention to her, despite their recent short but intense sexual history, made her want him even more. She figured the obliviousness he displayed must be an act. But, that was fine. She can play along if he likes, she thought.

With her back to him, overlooking the pool, she brushed the seat of her black bikini bottoms then rested her hands on her hips as her brother and her roommate climbed out. She wanted Brent to notice. Her long legs lead to a perfectly formed ass that she worked hard at keeping in shape. Hours at the gym ensured that wearing anything form fitting or skin exposing, drew attention, and she knew it.

As Allison and James made their way out of the pool, Claire turned her head back to Brent. He was watching her. His eyes looked over her slowly, taking in every inch. From her bare feet, up her calves to her thighs, pausing on her ass, up following her smooth back to the strap of her bikini top, her slender arm, sun-kissed shoulder, the curve of her breast as she turned to him. Her beautiful face, her blue eyes, a smile growing on her lips. She was watching him watch her. He froze. She closed the gap, snatched the tongs from him hands, and raised her eyebrows. "Checking me out, huh?" She whispered while making her way back to the grill.

Brent stood embarrassed, excited, horny. She caught him looking, plain and simple. Considering the things they did together in the past two days, this was innocent. Still, it was difficult for him to accept the speed and intensity of everything happening, and he was still not quite comfortable with how everything was unfolding.

His mind swam with the memory of her anonymously giving him oral through the glory hole at the adult bookstore the day before, waking him from sleep the next morning, kissing him, feeding him her breasts, all while Allison took her turn between his legs. Later, inexplicably, making out with his neighbor Jennie and cumming all over her. The image of her nude body glistening with his seed, the sleepy satisfied look in her eyes brought his erection to fullness. Now, here he was back in the company of these two bikini clad girls, poolside. The last few days had been crazy, unexpected, and otherwise unbelievable. His penis throbbed between his legs.

"Dude, how about that burger?" James asked breaking the spell, snapping Brent out of his daze. James smiled, looked over at the girls helping themselves, and returned his eyes to Brent. "Dude." He whispered. He shook his head and they joined the girls at the grill.

The rest of the afternoon went on without a hitch. The four enjoyed burgers poolside along with cold drinks. The conversation never strayed from safe topics. Aside from a handful of lingering looks, it was as if they were just a group of friends hanging out. Completely innocent.

Part 2.

"Great view." Virginia said. Standing at her bedroom window wearing a black tank top and tight gray leggings. She looked as if ready for yoga class. Her naturally fire red hair was pulled into a ponytail, accentuating her high cheekbones, full lips, and bright green eyes.

Like Jennie, she was lean, but well proportioned. Unlike Jennie, she was much more comfortable with her maturing physique. This resulted in a sexuality that contrasted directly with Jennie's appearance of youthful innocence. With every developing curve, Virginia experimented with increasingly sexy outfits. It seemed as if now almost every article of clothing she wore enhanced her figure in some way. Today was no exception.

"I just wish I could hear what they're saying." Jennie mumbled, cupping her hands at the window and leaning into them. She smelled freshly scrubbed. Her long auburn hair was still somewhat damp from a recent shower and she still retained the scent of shampoo.

Down below, by the pool of Virginia's back yard neighbor, Brent and James mingled with two gorgeous girls. After an in depth dissection of what they observed, Jennie and Virginia deduced that the blonde was James's sister Claire. The brunette, however was still a mystery to them. Jennie did not know what to think.

Despite practically growing up together, the bond Brent and Jennie once shared in youth had dissolved over time. Still, he remained her neighbor, classmate, and until this morning, a platonic friend in public, and an impossible crush in private. Until this morning... she would have only daydreamed about luring him into her room, stripping down to her panties, and making out with him to climax on her bed.

The scene playing in her head made her skin tingle. His breath on her mouth. Their tongues intertwining. His naked body pressed against hers. His arms holding her close. The desire to pull the fabric of her thin panties aside to let him inside her. Again and again, her engorged clit feeling the pressure and friction of his movements. The growing warmth of her body intensified with the thought of her nipples in his mouth, spreading her legs for him, wet, throbbing...

She caught herself moan audibly and snapped to the present. Her left hand was kneading a breast under her shirt. Her right hand was rubbing her pussy through her shorts. Virginia was watching her, mouth ajar.

"Oh my god Jennie. Seriously?" Virginia chuckled, obviously amused.

"Sorry." Jennie blushed as she attempted to compose herself. She fell back onto Virginia's bed. Her blue cotton running shorts were tight on her crotch, a hint of moisture in the crease. Virginia watched as Jennie's breasts jiggled under the thin fabric of her gray tee shirt as she rubbed her eyes. Her nipples were very hard.

Part 3.

Claire stepped away from the others to take a phone call. The table was littered with plates, crumbled napkins, and melted ice in empty glasses. Allison, Brent, and James shared stories of their youthful indiscretions. They laughed and joked, not knowing they were being watched. Claire finally returned, phone in hand.

"Well, it looks like Allison and I are going to be heading out for a little bit." She said, setting the phone on the table and taking a seat next to her.

"Where to?" Brent asked.

"We ran into some friends from high school at the supermarket. Remember Ashley and Lindsey?" She asked.

Ashley, Lindsey, and Claire were a trio in high school. "BFF's" they liked to say. Once they graduated, Ashley left for a stint in Europe, Lindsey to college on the East coast, and Claire began her life at the local university. As time passed, they moved on to other endeavors, but running into each other, it was only natural that they would want to at least hang out and catch up.

"They wanna take us out for drinks. You guys gonna be okay for a couple of hours?" She asked.

"Yeah, sure." James said.

"You two coming back?" Brent asked. He locked eyes with Claire, then looked away. By the time the words left his lips, he realized how lame it sounded.

"Yeah, it should only be a couple of hours or so. Why? You gonna miss me?" She joked.

He blushed.

"It's gonna be couple hours tops, maybe. You guys okay to clean up?" Claire giggled. She liked that Brent wanted her around. She wanted to be around him.

"Really?" James asked, looking around at the mess they made.

"I know, I know. We just gotta be there soon and we gotta get ready. I'll... We'll make it up to you guys, I promise."

Part 4.

"So I think I'm gonna see my guy later." Virginia mumbled as her thumbs sped across the screen of her cell phone, composing a text.

"Oh yeah? Am I actually gonna finally meet him?" Jennie asked, turning her back to the window. This was a well needed reprieve from the unending torture of watching other girls flirt with the guy she crushed on. Virginia sat propped up with a stack of pillows at her headboard. The room was growing dark from the setting sun.

"I don't think that's in the cards tonight." Virginia answered, looking up. She dropped her phone on the bed and joined Claire by the window.

"You tell me every last detail about what you two do together, but you won't even tell me who he is?" Jennie asked.

"Oh look, I think they're going inside." Virginia gestured back to the four below.

Brent and James finished gathered the napkins, glasses, plates, and the rest of the things left over from lunch. The girls lead them inside. Within moments, the serene silence returned to the backyard.

It's just not fair, Jennie thought to herself. I finally make my move... then freak out and lock myself in the bathroom. Now Brent's hanging out with these girls? Not fair!

Maybe it's totally innocent, but the way these girls were looking at Brent all afternoon, I seriously doubt it. I really need to talk to him... shit! She sighed, closed her eyes and tried desperately to think of what she could possibly do before her window of opportunity was gone forever.

"I'm gonna go over there." Jennie finally said. "I can jump the fence and... I dunno, try and get close enough to see inside. Then... what do you think..." She backed away from the window and turned to Virginia. The room was empty.

She's probably in her brother's room. She thought as she stepped away from the window. It was strange to Jennie how Virginia and her brother had suddenly become so close. The change in the dynamic of their relationship over the past year made her wonder what it was like when nobody was around. Jennie even entertained the idea that maybe it was him that she was regularly fucking. She laughed at the thought.

As she padded down the hallway, she heard voices from Virginia's brother's room. As usual, the door was open just a crack. She peeked inside and found Virginia laying on his bed, John was at his desk turned away from her on his computer likely working on homework. As much potential he had attracting girls with his broad shoulders and easy smile, he preferred to focused on school. While honorable, Jennie thought, it was a shame.

He was tall and handsome, but looked nothing like Virginia. She was two years younger than him and had an athletic, outgoing personality that contrasted with his quiet, studious manner. He was smart, but not socially awkward. His subdued observant manner almost gave him an air of mystery.

According to Virginia, girls were often attracted to him because of this. Jennie thought maybe it was because of his looks. Perhaps it was a little bit of both.

"Hey." Jennie announced, pushing the door open.

"Hey Jennie." John greeted her with a smile as he spun to face her in his chair. Jennie knew that he had always a thing for her, but with Virginia being one of her best friends, he was strictly off limits. Still, she didn't mind the attention.

"Hey John." She looked down at herself and realized that she really should have worn a bra. Crossing her arms as casually as she could, she turned to Virginia.

"So, I think I'm gonna go over there." She said as she sat on John's bed.

Virginia was laying laying on her front, propped up on her elbows with an open issue of Cosmo in her hands. She looked up at Jennie who sat at the foot of the bed, leaning back on her hands. Her hard nipples were visible only to Virginia beneath the thin fabric of her shirt.

"Seriously?" Virginia asked. She closed the magazine.

"I was thinking about jumping the fence and getting a closer look."

"What are you guys talking about?" James interjected.

"Look over at James's house." Virginia instructed.

John stood up and pulled the blinds open."What am I looking for?"

The girls joined him at either side. The sun was setting and the sky was getting dark. The interior lights of James's house illuminated the figures inside. Though behind glass and a good distance away, they were clearly on display. Allison stood closest to the sliding glass doors. Her white bikini left little to the imagination.

"Wow, great view." John mumbled.

As he stood at the window trying to get a good view inside the house, Jennie pulled Virginia out of the room and lowered her voice to a whisper.

"You're brother won't say anything will he?" Jennie asked.

"Nah, he's good at keeping secrets." Virginia answered, looking back into his room.

"Okay, good."

The girls made their way downstairs and out of the back door. As the night crept in, the air chilled slightly. Jennie wished she wore more than a tee shirt and shorts. Even a bra would have been a welcome layer.

"I dunno about this. What are you gonna do when you get there? What if you get caught?" Virginia hesitated.

"I'll be careful." Jennie replied as they reached the fence. Despite her lack of confidence when it came to guys, she had it in spades when it came to herself. Sizing it up, she saw that horizontal support beams would provide easy access to the other side. As long as nobody was paying close attention, she should be able to make it up to the house undetected. She was almost positive nobody would notice her.

After a moment, Virginia gave in. "Okay. Just... be careful, okay?"

"Roger that." Jennie quipped. She hopped over the fence almost too easily. Virginia waited quietly and listened for any movement on the other side. Crickets. Wind rustling through the leaves overhead. Nothing out of the ordinary. After a moment, she turned back to her house and up. Her brother still stood at his window, looking out.

Part 5.

James's slippery hands slid across the smooth hard surface. He passed the clean plate to Brent who set it on the rack next to the sink to dry.

"Dude." James looked at Brent with his eyebrows raised. A lifetime of friendship allowed a certain level of communication using an economy of words. In this case, James was referring to their afternoon with the girls poolside. In particular, James's subtle variation of the syllable was emphasizing Allison's amazing body and possibly his own sister's radiance.

"Dude." Brent agreed, subtly adding how hot Claire's ass looked in her little black number. He also hinted at the hypothetical possibility of getting lucky, if they played their cards right.

The following silence they shared was spent recalling their favorite moments. The images they burned to memory were reviewed for close inspection. Together they washed and dried the dishes deep in thought.

..................

Outside.

Jennie, with her back to the wall of the house, quietly crept to the side door of the garage. The idea of simply watching through the window was scrapped as James and Brent seemed to be quietly studying the layout of the backyard. It took only a moment of hesitation before she checked the door, found it unlocked, and closed it behind her once inside.

It was dark, warm, and the air sat heavy with staleness. It was immediately obvious that the garage door itself had not been opened that day, possibly several days. She pulled the small flashlight from the pocket of her shorts and clicked it on. The garage was empty. No car in sight.

Years ago, when the neighborhood kids used to play hide and seek, it sometimes took place here. Jennie recalled the layout of the garage and noted the absence of the SUV that James's parent's drove. She deduced that meant that they were not home.

James, Brent, and these two girls were all alone inside the house. There was nobody there to keep an eye on them. Nobody to stop one of them from pulling Brent inside an empty room and having her way with him.

She walked to the door connecting the garage to the laundry room, which lead into the kitchen. She pressed her ear against it and listened. The sound of her heart beating drowned out almost everything.

..................

"So, what are you gonna do about Jennie?" James asked.

"I dunno, I'm kinda thinking that she probably doesn't want to see me for a while... too embarrassed to talk to me after what happened." Bren't replied.

"You don't really do what she did on a whim. She's had it bad for you since we were kids, dude. Good for her for finally getting the nerve to do something about it."

"It just... happened so suddenly, you know? I wasn't expecting it."

"Yeah, well... so... boobs?" James asked, naturally.

"Dude, you would not believe the body she has. I'm talking boobs, ass... she's pretty fine, dude."

"Yeah?"

"I mean, obviously she's an athlete, so she's gonna be in shape. But, she never really wears anything to show off her body, you know? If she did, I might have made a move a long time ago."

"Yeah right. As long as i've known you, you have never made a move. Girls make moves on you."

"I'm a gentleman." Brent joked.

"Sure you are. With that thing, you'd think you would have a little more game." James gestured to Brent's crotch.

Brent laughed.

"So, how does Jennie compare to Allison... or my sister, for that matter? Yeah, I know you've been checking her out. I don't blame you, she's one hot piece of ass."

"She's right up there, man. All three in my bed? I wouldn't know where to start."

"Now, that's something to think about."

The voices trailed off and disappeared into the living room. Jennie cracked open the door and peeked inside. The kitchen was empty. Though the conversation was muffled, she distinctly heard her name several times. She closed the door behind her and worked her way in deeper.