The Jack Off Sessions Ch. 06

JOS Chapter 6: Fun and Games

Thank you all for taking the time to read this entry of The Jack Off Sessions. This being the sixth chapter, it might be a good idea to skim through the previous installments, read the cliffs-notes versions, or have a loved family member read them to you. I kid, I kid.

I'm really not much of a writer in my everyday life, so work on this when I can. Unfortunately, finding the time to sit down and write is hard to come by nowadays. I hope this one was worth the wait.

Thanks again for all of you who stuck with me this far on this project.

Enjoy...

Part 1.

This is so depraved, Claire thought. I can't believe I'm doing this.

She knelt on the soft carpet between her brother's legs. James stroked his throbbing erection inches from her face. She looked up at him with her clear blue eyes.

Do you want your pretty sister to suck your big hard cock?

She slid her hands up his thighs as she bit her bottom lip. She arched her back and wiggled her ass just a little as she leaned in. She knew how good this looked from his angle. She wanted him to see her as more than a sister and appreciate what a perfect heart shaped ass she had. She wanted him to know what he could have if he was only willing to just take it.

Heat radiate off of him. She could feel her cheeks blush with anticipation. She had thought about this moment many times since she caught him jacking off in the basement with Brent. She imagined herself in this very spot between his legs, about to do what she was about to do.

He slowed his stroke and brushed the engorged tip over her soft wet lips. She tasted his precum as she slid her tongue back into her mouth. She hoped that when all was said and done, she would have a lot more than just a mere taste.

The rigid thickness of his hard cock, veins snaking up the side, shaved smooth, was a masterpiece, she thought.

Over the years she had seen her share; Some big, some small, hard, soft, thick, thin, and everything in between. But this, beautiful example of male libido, this powerfully rigid appendage between her sweet brother's legs, made her mind swim.

After a moment of hesitation, she gave in to temptation.

She ran her fingers up his length, pressed her face against his hot velvet skin. He caught his breath and instinctively pumped his hips. She tilted her head to the side, parted her lips and slowly tongue kissed the side of his shaft while keeping her big blue eyes on his.

She worked all the way up with soft wet kisses until she reached the tip. She spread the lubrication of her saliva in a stroking, pumping motion with her small hands until he was slick. She opened her mouth and placed him on her tongue. He groaned as waves of pleasure pulsed from his core.

"Mmmm." She moaned as she closed her mouth around the engorged head. Her glistening lips enveloping, then sliding off. Again and again; enveloping and sliding back off. She continued to pump her hand up and down his shaft and and play with his balls as she teased.

Suddenly, she slipped him past her lips and into her mouth. Her tongue swirled around, slippery and hot. It was like a vortex of pleasure. She slid her fingers down to the base and held it like a tight ring. Expertly, she pushed further downward. Inch by inch he disappeared inside of her. Her mouth never stopped, her eyes never looked away.

At the end of that single motion, her face was firmly pressed down to his base.

James was balls deep in his sister's throat.

As tight a fit as it was, she managed to slide out her tongue and lick his balls as her throat clenched and relaxed, miking him, coaxing his sweet release.

She slid him back out, every inch slippery and wet. In a piston-like motion, she pushed her head all the way down again, then all the way back up. She continued this in intervals, taking a short break every so often to catch her breath. In these moments, she continued to gently massage and tug his balls with her delicate fingers.

It was like a hot wet embrace that urged his climax and never subsided. As erotic as her mouth was at giving him pleasure, the look in her eyes brought him to the edge.

She felt his hands grip the sides of her head and begin to guide her ascent and decent. He pulled her up, the head of his cock held tightly between her lips as he paused, her tongue exploring, begging him to stay inside. Obediently, he slid her back down slowly, enjoying the look of his sister's face as her lips stretched to accommodate his thickness.

Her wet pussy throbbed as he grinded her face firmly against his pubic bone, the entirety of his fully erect penis down her throat once again. Her nipples tightened. She squeezed out a moan of pleasure. He leaned back and spread his legs further.

He loosened his grip and let her slide off. Once free, she lowered her hungry mouth to his balls as she pumped his shaft with her slippery hands. Saliva cascaded down his length and glistened around her mouth. Her tongue gently sucked and massaged him while she continued to explore him with her hands. Her technique was very wet and sloppy but expertly performed.

Tilting her head to the side, she kissed the smooth sensitive spot behind his balls. Not just a peck, she kissed it with the the sucking, tongue massaging wet intensity she learned to perfect over the years. He pumped his pelvis involuntarily and groaned with pleasure, his spit-lubricated cock slipping in and out of her tight grip.

Watching his face, she saw the hunger and uncontrollable lust that she had only dreamed of seeing.

She moved back up and slid him just past her lips then paused. She looked up at him pleading, begging with her eyes. He took hold of her head and pushed her down. Every inch of his rock hard cock slid down her tight throat slowly. He pulled her up until he was almost completely out then slid her back down again.

He continued to fuck her mouth and she loved it every moment of it.

As his hands guided her speed, his pace quickened. She saw a look of perverse desperation flash across his face and she knew he was close.

He let out a long groan.

Time stopped.

She felt the muscles at the base of his cock flex.

At the first taste of his sweet release, he pushed her all the way back down.

She felt him pulsate and throb in her throat as he drained his seed inside of her. He held her tightly and moaned.

"I love you."

She could feel every powerful jet of his cum shoot deep inside her as she swallowed, and swallowed, and swallowed...

---

Claire's eyes fluttered open. They met with darkness.

Her vision slowly adjusted and she recognized the familiar arrangement of her old bedroom. She was back at home.

Alone.

A sliver of moonlight fell across her bed though the curtains. She was tangled in her sheets, sweat coated her half naked body.

She lowered her hands between her legs and replayed the dream.

---

Jennie walked along the shadow of the fence quietly. She reached the far end of the yard, pulled herself up the fence and dropped over the other side. Her knees buckled more out of mental exhaustion than physical strain. She took a seat in the grass and exhaled.

Brent and James came all over that girl.

The images replayed in her head, pausing, fast forwarding, rewinding, replaying again and again. Though she brought herself to orgasm more times than any moment in her brief sexual history there in that basement, her body still begged for more. She pushed herself up, ignoring the temptation and made her way inside Virginia's house.

She immediately kicked off her shoes and climbed the stairs letting muscle memory guide her. Once she reached the landing, a moan brought her back to reality.

"Uuhhhhh... Uuuhhmm..." Another, and another, and another.

It continued rhythmically again and again as she followed it to it's source: John's room.

For a moment she thought if she caught Virginia's brother watching porn, she wouldn't be able to resist herself. She knew he liked her, he aways had.

Maybe what I need is a good hard fucking.

She pushed the door open and stopped in her tracks.

Virginia faced away from the door. Her toned back was bare and tapered down to her perfect ass. She was straddling John's hips. Her knees dug into the mattress as she raised and lowered herself rhythmically on her brothers thick erection, a moan escaping her lips as he bottomed out inside of her.

Jennie gasped when she realized what she was seeing.

John's eyes parted slightly as his sister's tongue explored his mouth. He tilted his head, allowing him to see past her bare shoulder.

His eyes met Jennie's.

They went wide.

He froze.

After a moment, Virginia realized something was wrong. John had stopped moving. She pulled back and registered the look of shock on his face and turned her head to see what spooked him.

Jennie stood motionless in the open doorway, her eyes coasting over their glistening bodies.

Virginia's wet pussy tightly gripped John's hard cock, her juices ran down his length. John's strong hands still gripped his sister's ass. Her bare breasts were wet with his saliva.

A moment passed... and another. Jennie could smell the sex in the air. It was electric. Her skin tingled.

She pulled her shirt off and dropped it on the floor.

Virginia smiled as Jennie pushed the door closed.

Part 2.

Jennie's thighs flexed. Her arms pumped. Her muscles burned as sweat rolled down her temples.

"Slow down Flash. What's the rush?" Virginia called from almost half a block behind her. She was breathing hard.

Jennie slowed to a trot. "Sorry." She called back between deep breaths.

They had made this run dozens, if not hundreds of times before. Since they met in Jr High, the two often found the time for a jog around the neighborhood. This gave them the time to talk and reflect on their lives. Until recently their topics were pretty tame: homework, boys they liked, TV they watched, music they listened to. Only recently did their conversations begin to almost solely focus on boys.

It was usually a pretty one sided. Virginia was much more outgoing and less of a tomboy than Jennie. By the time they were 18, Virginia had left a trail of heartbroken guys all across their small town. Jennie, on the other hand, had only a handful of boyfriends, every one almost always ending prematurely. Her biggest obstacle for making it work, Virginia often stated, was that she was helplessly in love with her neighbor Brent.

Virginia often encouraged Jennie to date the guys who were obviously into her. This usually led to Jennie going on dates, sometimes several. Ultimately, she always ended up single and wondering if Brent would ever make a move on her.

It wasn't until the day prior did Jennie finally take it upon herself to make a move on him. Of course, having thought about, dreamt about, fantasized about being with him for years, when she did finally did make a move, she couldn't control herself. She all but dry humped him until they both came, then locked herself in the bathroom out of embarrassment until he left.

Stupid, stupid, stupid. She cursed herself.

"Mind somewhere else?" Virginia asked as she caught up.

"Yeah..." Jennie mumbled.

A moment of silence.

"Is it weird now?" Virginia finally asked. She slowed a bit and faced Jennie.

"What? Because of last night?" Jennie returned to reality.

"Yeah, I mean... are you freaking out because of what we did?" Virginia asked, looking down at her feet.

"No! No, it's not that. I'm actually... pretty okay with it I guess."

Jennie really did mean it. To her, it was as if a door opened and the world was suddenly a little bigger. Good, bad, whatever. It was new and exciting and it took her mind off of Brent for once. She needed it and she was glad it happened with people she trusted.

Like with most things, she wanted to keep an open mind and see where it went. At some point, she realized, she'd have to really step back and think about it. Later, she decided.

Later.

"So? What is it then?" Virginia slowed to a walk, matching Jennie's speed.

"I was thinking about Brent." Jennie caught Virginia's eyes and blushed.

"Of course." Virginia laughed. She was relieved.

Though she didn't show it, she was worried how Jennie was processing what happened the night before.

The threesome between Jennie, Virginia, and her brother John just happened. It was completely spontaneous. She wasn't expecting it. She wasn't planning it. John was definitely caught off guard. She was afraid it would ruin everything. Hearing that Brent still topped Jennie's list of things to worry about was a good sign.

"Brent and James and that girl... It was... I dunno... crazy... " She trailed off as her mind wandered.

Virginia was tempted to say something, anything, but she just had no words.

They jogged in silence for a block.

"Why the hell did I let you pick out my outfit anyway?" Jennie suddenly laughed, looking down at herself.

Her top was white with bright green trim around the neck and sleeves. To say it was tight would have been an understatement. Jennie imagined that any healthy male that caught a glimpse of her jogging, would instantly know her bra size and could probably pick her out of a lineup without ever seeing her face.

Her bright green shorts matched the accents on her shirt. They were also very tight and very short. Her long tanned legs ended in matching running shoes, which were her own. Thankfully, she thought, at least something about her outfit was actually hers.

"What do you mean?" Virginia played dumb, a grin on her lips.

That morning they discovered that Jennie's clothes needed thorough washing along with John's sheets and a few other things. In the unique position to find something for her to wear in the meantime, Virginia thought she'd find something that would properly show off her body for once. She didn't realize just how heavy handed she was until this very moment.

"Look at you... and look at me..." Allison wore a baby blue tee shirt, black shorts, and matching running shoes. She looked practically modest next to Jennie.

Jennie's breasts visibly jiggled with every step. Virginia started to feel a little bad. Still, it was kind of funny to see Jennie dressed this way. Of all the girls in the town, nobody would have ever pictured Jennie Connor wearing anything quite this revealing.

"I look like I'm out to fuck the paper boy." She laughed.

"You look fucking hot Jennie! I just wanted you to enjoy your body for once. Seriously, look at you. Smoking fucking hot." Virginia said.

"Look." Jennie slowing to a stop. Her attention was no longer on what she wore. Rather, she was focused ahead in the direction of Virginia's house.

She pulled Virginia onto the nearest well manicured lawn, next to a high hedge wall. She peeked around the side.

She pointed to the driveway of the house next to Virginia's.

James's house.

This is where she witnessed the unexpected scene between James, Brent and the unknown brunette the night before. This is where her hidden primal sexual hunger was triggered, leading to an all night, no boundary, sexual experiment with Virginia and her brother John. Now, here she was dressed like a teenage boy's fantasy hiding behind a bush, heart pounding in her chest, wondering what was going to happen next.

The brunette stepped into the driveway first. She wore a dark blue sundress with white polka dots and sandals. Her hair was pulled back into a ponytail and glasses framed her face. Despite her voluptuous body, her appearance was relatively conservative.

She looked cute.

Cute as a fucking button, Jennie rolled her eyes.

She recalled seeing the girl, naked and on her knees on front of James and Brent as they stroked their gushing erections over her, their cum spilling on her tits, her fingers slipping into her pussy, rubbing her clit, moaning with pleasure. Jennie resisted collapsing onto the grass at that moment and submitting to the warm throbbing sensation between her legs.

Get a hold of yourself!

The blonde that followed close behind was James' sister Claire. She wore a sheer blouse over a white tank top, tight blue jeans, and knee high boots. Unlike the brunette, her outfit really accentuated her body. Her jeans hugged her perfect ass, her sheer top hinted at ample breasts beneath.

They climbed into the red VW Golf, backed out of the driveway, and disappeared down the tree lined street within moments.

"That was the girl?" Virginia asked.

"Yeah." Jennie confirmed.

"Didn't look like much." Virginia yawned.

Jennie appreciated how Virginia always sided with her. Even in a situation like this, she made the effort to lessen the sting.

BFFs.

"You didn't see her yesterday. She has the body of a freaking porn star." Jennie shook her head.

"Oh, so she subscribes to the Jennie Connor school of conservative fashion?" Virginia joked.

Jennie smiled, "I don't like dresses. Besides..." She gestured down at herself, "...this definitely is not conservative."

"You're welcome." Virginia smiled. She motioned toward the house and empty driveway. "The coast is clear. Now's your chance to make your move." She said stepping back onto the sidewalk.

"I don't think so..." Jennie hemmed.

"Come on, don't be a wuss. It's just Brent and James in there, right?" Virginia nudged her.

"Last night I watched Brent and James cum... all... over... that girl. Why would I even..."

"Fast forward half an hour and you're fucking my brother." Allison interrupted.

Jennie blushed.

"Well, that's my cue. I'm gonna go inside and see if John's up." Allison winked. "Now, take your time Jennie dear."

"Wait." Jennie pleaded.

"Seriously, at least an hour."

"Come on..."

"Seriously." Though Virginia smiled, Jennie saw in her eyes that she was indeed serious. The reality that she interrupted Virginia and John the night before was not lost on her. She didn't protest as Virginia left her alone on the sidewalk.

As Virginia's door closed, James' door opened. Jennie dropped into a squat back behind the hedge and peeked around side. Brent came out first then James. A moment later they were on their bikes and down the street headed in the opposite direction where the girls drove.

She watched as they peddled away, shrinking in the distance. Impulsively, she jumped to her feet and began following them. She knew that this was probably a very bad idea.

I should just go home and change out of these ridiculous clothes before someone sees me. Someone's going to see you and that'll cause all kinds of trouble.

She pushed the thoughts down and kept her pace.

Though they were far in the distance, they never left her sight.

Part 3

Their cocks stretched her tight pussy. Her juices lubricated them as they slid past each other deeper inside.

James passed the magazine to Brent.

"Hot." Brent grinned.

They stood side by side in front of the wall of magazines. From one to the next, they browsed the various titles, passing them back and forth when something especially interesting caught their eye. The single employee behind the register didn't seem to mind them grazing his merchandise. He himself alternated looking though a magazine of his own and watching a bank of televisions playing porno movies on the counter behind him.

Through the doorway with the purple neon sign over it that read Arcade, a woman and two men appeared. Brent was surprised to see anyone else in the store. Though there were a few cars in the parking lot, they were alone the whole time they looked though the magazines.