The Jack Off Sessions Ch. 06

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She was middle aged but pretty, the man on her arm was a bit older but likewise attractive. The second man looked like a construction worker or some sort of laborer. In any other circumstance it would have been odd that they would have such camaraderie, but here in Wonderland, anything seemed possible.

They chatted as they left the store.

"Wanna check out the booths?" James said after the doors closed.

"Sure." Brent placed the magazine back on the shelf and together they disappeared into the dark hallway.

---

Jennie pulled the door open to the small building after several moments of hesitation and watching three customers leave. Two bicycles were secured to the bike rack, and a single car in the parking lot was all that was left. Jennie figured that the car must belong to an employee, leaving Brent and James the only two customers.

Bells jingled overhead announced her entrance. She stepped inside and the door closed behind her.

Everywhere her eyes landed was sexual in nature. Movie covers featured graphic acts between multiple partners. Magazines had titles she could never say out loud without blushing. Toys lined the shelves that confused and aroused her in equal measures.

She was embarrassed. She wanted to turn around and walk out. She wanted to laugh. She wanted to call out for Brent to save her, take her away from this place and fuck her hard on her soft comfortable bed and confess his undying love for her.

She did none of these things.

Quietly, she stepped into the closest aisle and looked around. Aside from the single employee behind the counter reading a magazine, the place was empty.

Brent and James have to be in here somewhere.

She saw the dark hallway with the purple neon sign along one wall. If they weren't in the main part of the store, they must be somewhere deeper inside. Past that sign, somewhere in the darkness perhaps?

Stop.

Turn around.

Just leave before someone sees you in that ridiculous fucking outfit. Just go!

NOW!

She suppressed her thoughts and stepped through the doorway .

Her eyes adjusted as the layout became clear. The hallway had a series of doors on either side. As she made her way deeper, she saw that many of the doors were open. A small booth, a single chair, a TV mounted to the wall comprised the interiors.

Private viewing booths, she thought

Further back was the familiar sound of sex. It seemed to be coming from one of the open booths near the back. She peeked around the corner of the doorframe and saw it was empty. On the screen, a video was playing.

A woman straddled a man who sucked her breasts. An image from the night before flashed in her mind.

Virginia fucking her brother.

His cock sliding deep in her wet pussy.

His hands squeezing her ass.

Their mouths locked in an incestuous kiss.

Jennie stepped into the booth and closed the door. A simple latch secured it shut. She sat down and proceeded to watch the movie.

His cock slipped in and out of her. Jennie lowered her hands between her legs and began to rub herself through her shorts. He alternated his mouth from one nipple to the next then back up to her lips. Jennie pulled up her shirt over her chest and squeezed her breasts as she moaned.

As she relaxed, she saw a hole in the wall from the corner of her eye. Through that hole, light flickered on the other side. She leaned in and looked through. Just like in her booth, the television mounted on the wall was on. It was a different movie. Just as graphic.

Brent?

Suddenly, the hole went dark.

She stood up.

Looking down, she saw a thick, hard appendage slide through. By the time his balls dropped over the lip, over nine inches of throbbing cock twitched in anticipation of her warm touch.

Brent.

---

She looked passed the wall in her mind and imagined him pressed against it. She leaned into it, picturing him inches away. She took him in her small hands and gently squeezed. She could almost feel him groan with pleasure on the other side.

She slid her hand from the tip to the base, feeling just how hard he was.

Like carved wood.

Impulsively, she knelt on the cold concrete floor, directly in front of it. Her lips inches away.

She turned it from side to side, imprinting it to memory. She licked her lips and slid the head in her mouth.

Oh my God, what are you doing?

Remembering what she learned the night before, she relaxed her jaw and used her tongue to distribute her saliva. She eased it inside more and more with every bob of her head. Her hand pumped the base of the shaft as he slid deeper past her lips.

With that, she gave herself completely to her desires. The voice in her head stopped. It was just her and Brent alone in this den of sex and perversion. She was very aroused.

He started pumping his hips, pulling from her mouth before sliding back in. She moved closer to the hole, her lips almost pressed against it as he proceeded to fuck her mouth.

She squeezed her breasts with her free hand, the other between her legs. After a moment, she realized a different cock was in her mouth. She moved back a bit as it slid past her lips and confirmed her suspicion.

James?

She didn't stop.

She didn't even pause.

She continued to suck, lick, and enjoy the sensation of being their tool for pleasure. She completely surrendered herself to her desires.

---

Brent watched as James fed his cock through the hole. Even in the dim light, he could see it glistening with her saliva. Every vein bulged, he was engorged to capacity.

"Dude..." He smiled at Brent.

"Fuck yeah." Brent nodded, stroking his own hard cock inches away, patiently waiting for his turn.

James slid all the way through and pressed hard against the wall. He tilted his head back enjoying the sensation. He moaned with pleasure.

Finally, he slid slowly out. His cock dripping with her spit. He paused before pulling completely out as her lips appeared just beyond the ridge, wet, full, and hungry.

James stepped aside as Brent positioned himself in front of it and slid through.

"Oh God, this feels so good." He groaned.

"Go all the way though, see how much she can take." James said staring intently at the hole as Brent fed his cock through.

After a moment, "Oh fuck man, I think she's fucking me." He gasped, looking down. He pulled a few inches away as James bent down to look through.

Her wet pussy gripped Brent's shaft. She was pressed firmly against the wall, welcoming him inside her.

"Yeah, dude, that's her pussy."

Brent slid back through, deeper inside. They could hear her whimper beyond the wall. He pistoned in and out, his full length sliding back and forth. James was tempted to reach down and feel how hard he was, scoop some of her juices onto his own cock and use it as lube.

"I'm gonna cum man, seriously this is too good."

"Do it man, fill her up." James instructed.

Brent pressed firmly against the hole and grunted. James watched his face wash with ecstasy. His lips parted as he took in uneven breaths. The pressure increased then released as he pumped his cum inside of her warm depths. He moaned and shuddered as his balls drained in her tight wet pussy.

He finally relaxed and slid out. Just as he did, James slid in, their cocks brushing against each other for the briefest of moments.

James could immediately feel her wet embrace. He imagined his hard cock filling the space that Brent was just in. He imagined Brent's cum lubricating his shaft and he pushed deeper inside.

"Oh my God."

Beyond the wall, their unknown partner rose and fell on his cock, fucking James in a quickening pace. Her pussy tightened around him, gripping him, almost pulling him deeper inside of her.

"Oh fuck, i'm gonna cum."

"Yeah, fuck that pussy. Shoot that hot load." Brent's eyes were glued on the base of James's cock as it swelled with the impending climax. James watched his face, filled with lust, drunk with arousal. From his core he felt the pressure rise just before his muscles involuntary pulsed, releasing torrents of his seed.

As he throbbed inside her, he could feel the slurry of their cum around his cock. It spilled out over the lip of the hole as he added to it, again and again until he was completely drained.

---

Jennie felt him finally slide out of her. She remained with her arms outstretched against the opposite wall, pressing her rear firmly against the hole. Cum dripped down the back of her legs. The tremors of pleasure slowly subsided and she began to worry that if she pulled away, they might look through see who she was. She remained in this position until she heard the door to their booth close.

After a moment, she stood up and slowly bent forward to look through the hole.

The booth was empty.

The television was off.

She was alone once again.

Their hot cum warmed her her thighs as it slid down her legs and soaked into her socks. She dropped into the chair and caught her breath. With the illumination of her screen, she looked down at herself. Nude except for her shoes and socks, her pussy throbbed as the final waves of pleasure washed over her.

What did you just do?

She heard booth door next to her open then close.

The television flickered back on.

They're back!

Her nipples instantly hardened.

She peeked through the hole.

A hard cock slid through.

It wasn't either of them.

She bit her lip and dropped to her knees.

Part 4.

Brent and James returned home and made their way into the kitchen, led by the scent of food.

Claire pushed sizzling meat around a hot pan as Allison sliced up tomatoes on the chopping block.

"Hey guys. Hungry?" Claire smiled back at them over her shoulder. Brent approached from behind to see what she was cooking. As he looked over her shoulder she leaned into him. It was surprisingly intimate and caught him off guard.

"I am so hungry, you have no idea." He said.

"Great. Why don't you guys wash up and we'll make you plates."

---

The next hour consisted of dinner, desert, and polite conversation.

"That was good." Brent sighed and leaned back into his chair looking down at his empty plate. He hadn't realized just how hungry he was.

"Great even. Seriously Claire, when did you learn how to cook?" James asked.

"A single girl on her own has to fend for herself, you know." She explained.

"Claire and I cook all the time." Allison added.

"I don't think I ever saw you pick up a single spatula when you still lived here." James joked.

A smile spread on Claire's face.

"Remember the time I threw a frying pan at you?"

James laughed.

"Yeah, right here." He traced an indentation on the wall with his finger.

When they were kids Claire and James sometimes reenacted scenes from the cartoons they watched together.

One Saturday morning, Claire lost control of a frying pan she was chasing him around with while trying to flatten his head. Instead, she slipped on the tile floor and the pan went flying. It ended up missing James by inches, leaving a hole in the wall.

They spent the rest of the afternoon together trying to patch it before their parents got home. They did a pretty decent job too. It took over a week before their mom finally noticed it.

"Well, don't worry. I've outgrown all of that."

"Obviously." He said, quickly assessing her body.

She looked at him sideways but let it slide.

As the girls washed the dishes, the guys started the movie they picked up on their way home. Of course like gentlemen they offered to reverse the roles, but the girls insisted.

---

"She is so hot." James commented as the leather clad vampire backflipped over a speeding car, firing guns akimbo. The girls joined them on the couch holding pink drinks in tall glasses.

"She's okay." Claire sighed taking a sip.

"Okay? Look at her, she's smoking hot!" James said.

"Yeah, she's pretty..." Claire yawned.

"Pretty? She's fine as hell!" James stated.

"You boys... She's probably wearing a padded push up bra, you know. Hollywood movie magic." Allison said.

"What are you saying?" Brent asked.

"Well, I've seen her in a few other things. She was in this Victorian period drama and she goes topless. She was no way as stacked as she looks in this movie." Claire explained.

"I dunno, she looks pretty good."

"Don't get me wrong, she looks good, but she's definitely been enhanced for this role."

They watched the action scene play out. It was over the top, but entertaining. As a dialog heavy scene commenced, James broke the silence.

"So, can I ask you a question?" James asked Allison.

"Sure." Allison replied.

"Since we're on the subject..."

"Okay..." Allison replied suspiciously.

"How big are your boobs anyway?" He asked as his eyes drifted down to her chest.

She laughed.

"Seriously James?" Claire moaned.

"I mean, you're so tiny but your boobs are so big." James persisted.

Not an ounce of shame, Brent thought.

"Well, how big do they look to you?" She said as she arched her back slightly, testing the the integrity of the buttons on her dress.

"I dunno... pretty big."

"If you had to guess?" She asked looking down at her chest.

"D?"

She poked her index finger toward the ceiling.

"Double D?"

She continued the gesture.

"I dunno, E?"

"G or FF, depending on the bra."

"Wow, I didn't even know they went that high." James said. His eyes shamelessly stayed focused to her chest. Brent saw the telltale signs of a raging hard on beneath his cargo shorts. Allison cupped her breasts in her small hands and squeezed.

"It sounds way more impressive than it really is. I'm really small, so it seems a lot bigger." She could have told him that she was an alien princess from the planet Barsoom. He wouldn't have noticed. The way she casually squeezed her breasts together enhanced their volume to such a degree that it left him practically mesmerized.

"No... they are impressive.... no doubt..." James mumbled as he nodded involuntarily.

She almost had the cartoon quality of the feminine ideal as imagined by a hormone fueled teenager. Petite but stacked. Her large breasts, thin waist, and hips that allowed an ass that stopped happily married men in the tracks, made her impossible not to fantasize about in all manner of sexual scenarios. Adding delicate, almost angelic features and she was a woman that in old black and white movies, with the right colored red lipstick, could have easily made a private detective unravel his life for just a moment of her attention

"It's really hard trying to find a bra that fits, to be honest." Allison continued, as she brushed a lock of mahogany hair from her brow and looked up at him with dark lustrous eyes. She realized that her idea of restrained flirting left James in a trance.

"I look like a little boy next to her." Claire quipped knowing that it wasn't true.

A good six inches taller than Allison, Claire had the proportions of a playmate. Allison often joked that if money ever became tight, Claire always had a the option to become a lingerie model.

"Hey, small boobs are cool too." Brent played along. He smiled and shrugged, letting his eyes fall on her chest for the briefest of moments.

"My boobs are not small!" Claire gasped, bringing her hands to her breasts.

"There's nothing wrong with small boobs. Yours are cute!" Brent said holding up his hands in surrender. He was piling it on now. The look on her face; shocked but amused, added a dimension of vulnerability that contrasted with her otherwise confident sexuality that put him at ease. It made him feel less like a kid in the company of a woman, and more like the man he actually was.

"Oh my god! Cute? My boobs are cute!? You are really making me feel like I'm 13 again!" She pouted.

"Hey, I like girls with small boobs." He grinned and squeezed her knee condescendingly. On the outside, he gave her the look of an understanding father figure or close platonic friend. Inside, he wanted to slide his hands up her thigh, pin her down with his body, taste her lips, feel the heat between her legs...

"You are such an asshole!" She slapped his hand away and laughed.

"Come on, I'm just kidding. You have great boobs." Brent confessed.

He was surprised how comfortable he was. Days before, he would have been at a loss for words in front of someone as beautiful as Claire. At no point would he have even been able to bring up the topic of another girl's breasts in front of her, let alone joke about it.

"Jerk!" She crossed her arms over her chest.

"Seriously, you're... very sexy." He trailed off.

"Really? You think so?" She lowered her arms and looked into his eyes.

"Yeah... I mean..." Brent looked over to James.

"Forget my brother, he's not even paying attention." She said.

Allison was fondling her breasts as James watched with pure joy on his face. She looked at Brent and Claire with a stupefied expression. "I think all the blood left his head." She laughed.

Claire brought her hand to Brent's face and focused his attention back on her. This close, he noticed the light freckles on the bridge of her nose. He recalled that when she was younger, those freckles were much more pronounced. Seeing her again after the year or so she had been in college, he hadn't noticed them at all. He reasoned that the time in the sun by the pool might have brought them out. Then again, everything else about her seemed to have changed so much, it was possible that he could have been focusing on other things.

Seeing him flustered stirred something inside her. She bit her lip and steadied her gaze. "You think I'm sexy." She whispered.

The look on her face, the shimmer in her eyes, and the close proximity to him stirred the boyhood crush he had secretly harbored for her since he was very young. It took all the strength he had not to lean in and kiss her. He wanted to feel those soft slips pressed against his, feel her tongue in his mouth, know that she she wanted him as much as he wanted her...

She knew with a little effort, she could get him to just about anything.

---

"This is good." Brent said after taking a sip.

"It's this pineapple-rum concoction we perfected in the dorm. You can't even taste the alcohol really." Allison explained as she handed a glass to James.

"It's like juice." Brent took a big swig.

"Whoa there. Pace yourself. It might not taste alcoholic, but it is. We don't want you passing out now. You'll miss all the fun." Claire winked.

"What kind of fun?" James asked, swallowing a gulp.

---

"I have a game..." Claire suggested as she plopped down on the recliner with a drink in her hand.

"Oh no." Allison groaned.

"Come on, it's fun!" Claire whined.

"What is it?" Brent asked.

"Childish." Allison mumbled.

"Shut up, you always have fun." Claire nudged her shoulder.

"Well, what is it?" James asked as he set his drink on the coffee table.

"Have you guys ever played Truth or Dare?"

Part 5.

During Claire's senior year of high school, Brent and James spent almost an entire night snooping on her and her friends during a sleepover.

Earlier that evening, Claire made a deal with them that if she and her girl friends got exclusive access to the first floor of the house, she would let them go unsupervised for the whole night upstairs. This agreement was, of course, made without much foresight. Once hunger set in, Brent and James snuck downstairs for supplies.

As they filled their arms with leftovers from the fridge, they overheard the girls laughing. Naturally, they eavesdropped.

The gaggle of girls lounged in sleepwear that left little to the imagination. Skimpy tops, tight bottoms, bare skin. The smell of scented lotion and the sound of girls giggling filled the house.