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.


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.


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.


“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.


“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 cumallover… 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.

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?


Turn around.

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


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.


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.


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.


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.


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.

Eventually someone suggested truth or dare.

Over the course of the night, Brent and James listened on as they confessed the most private of secrets, believing that nothing they said would leave the room. First attempts at oral sex, handjobs in the back of cars, crushes on other girl’s boyfriends, and just about everything that could possibly come up when truth was chosen.

Before long, truths turned into dares and half the girls ended up skinny dipping in the pool by the end of the night. Brent and James quietly watched it all.

“Since you’re the guest, you can go first.” Claire smiled.

“What about Brent? He’s a guest too!” Allison argued.

“He’s next. First you.” Clare took a sip.

Fine.” Allison agreed.

“To make it interesting, lets let the guys ask.” She continued.

“Truth or Dare?” Brent and James asked in unison before she could change her mind.

Allison shared a look with Claire. “Dare.”

They stood facing the sliding glass doors leading to the back yard. The four of them stared at the glassy surface of the pool as James flicked on the patio lights.

“Can I pick truth instead?” Allison begged, already knowing what the answer would be.

“Rules are rules.” Claire smiled.

“This is only the first round!” Allison whined.

Rules are rules.” James mimicked Claire.

“Fine. Just wait until my turn.” She gave him an amused look.

Allison hitched her shoulders, letting the straps of her dress fall down her bare arms. She wiggled her hips, allowing the thin fabric pool on around her feet. She stood before them in nothing more than a lacy white bra and matching panties.

She paused a moment allowing them to take it all in.

Her skin was sun kissed, likely due to the afternoon by the pool. The looks on Brent and James’s faces spoke volumes. Claire held in a laugh.

“What about just the top?” Allison asked cupping her breasts as she looked from Brent to James with puppy dog eyes. It was intended to evoke sympathy, but considering her state of undress, it was more sexy than anything.

Rules are rules.” They answered in unison and laughed.

She released the clasp between the cups and let it drop to the floor.

Full and firm, her breasts were amazing. On her tiny frame they looked very large, but somehow fitting. Her nipples were a shade darker than the skin around them and obviously very hard. After a moment, she hooked her thumbs into her panties and shimmied out of them. By the time they were at her feet, she was bent at the waist, her ass high, her breasts jiggling with every movement. She straightened up, closed her eyes, and shook the tension from her hands. “Here goes nothing.”

In a flash, she was out of the door. They watched as she brought her legs up in mid air, clear the lip of the pool, and break the smooth surface. She was underwater for a fraction of a moment before she began to pull herself back out.

The image of her emerging seared into the memory of James and Brent instantly.

Her body glistened as she ascended the steps. Rivulets of water slid over and between her breasts. Between her legs a small heart was carefully shaved into her shortly cropped pubic hair. Her strong thighs flexed, her eyes twinkled with a mischievous gleam.

She trotted back to the house leaving a trail of small wet footprints. With teeth chattering, she snatched the towel Claire held out to her and immediately disappeared into the bathroom.

The guys were speechless, mouths open, salivating.

Best summer ever.


Claire looked disappointed. She was expecting Brent to choose dare. Considering the instant nudity during the first round of this little game, she was hoping to keep the momentum going. With the constraints she was given, she finally asked, “Who was the last girl you had sex with?”

Brent and James shared a brief look. Claire saw it… but said nothing.

Their escapade in the booth earlier that day was a secret they understood they would take to the grave together. Moreover, even if it was something they agreed to share with the world, they had no name or identity of the girl on the other side of that wall.

Claire wanted a name.

He was pretty sure she was not asking him to out her as giving him head through the glory hole a few days before, or the makeout session she had with him the following morning ending with Allison going down on him. Regarding Allison, he and James promised not to bring up their late night basement rendezvous if Claire asked, so that was out of the question.

“Well…” Claire urged him. He realized that replaying all of the recent events in his head had resulted in a temporary lapse of time.

Allison sat quietly squeezing the moisture from her hair with a towel. She wore an oversized bathrobe that Claire loaned her. Her dress and underwear were now neatly folded on the arm of the couch by her side. She looked at him with an expression that he understood as a reminder of his promise.

“Remember Jennie?” Brent asked. Of course. Though the last few days had been packed with new sexual experiences involving everyone in the room, there was someone else he could safely talk about without breaking a promise or prematurely revealing a secret.

“Little Jennie Connor?” Claire asked.

“She is 18 now… not really a kid anymore.” Brent explained.

“Who’s Jennie?” Allison asked as she pushed her glasses back on her face.

“Brent’s neighbor.” Claire explained. “She used to follow him around everywhere when we were kids. She was so in love with him.”

“I… don’t know about that…” Brent looked away.

“Suuure, anyway, you were saying? The last girl you fucked?” Claire smiled taking a sip. James looked at her wide eyed with a smile on his face. He rarely heard his sister use such vulgar language before. He liked it

“Well… the other day we kinda hooked up.” Brent explained.

“What do you mean, kinda?”

“I was over at her place and we… kinda made out.” Brent clarified.

“You just saw me butt ass naked. I’d like to hear details please.” Allison folded the towel she used on her hair on her lap. Though it was understood that she changed into some of Claire’s clothes after her dare, the robe wrapped around her body left some doubts.

“Okay… I was mowing the lawn and she was washing her mom’s car. After I finished, we got to talking. She offered me something to drink. I was thirsty so I took her up on the offer. Anyway, I ended up in her house.”

“Go on…” The girls giggled.

“Anyway… one thing leads to another and we’re making out on her bed. Before I know it, I’m completely naked and she’s topless, little panties on, grinding me.”

“Who was on top?” Claire asked.

“Yeah, and slow down. Details, remember?” Allison said.

“Okay… so, we’re kissing. She’s on top. I’m super horny and she’s grinding against me…”

“More details.” Allison reminds him.

“Okay… she’s grinding her pussy on my… cock. She’s so wet. Her tits are in my face and I’m sucking on her hard nipples. She’s moaning and starts going faster, and I think she starting to… you know…”




“Yeah… she start to cum… and it’s so fucking hot I couldn’t help myself.”

“Mmm Hmm.” Allison bites her lip.

“I couldn’t help it and I came too.”

“Hot.” Allison whispers.

“Then what?” Claire asks.

“Nothing. I came, we kissed a little. She gets up, goes to the bathroom and doesn’t come out. I waited for like fifteen minutes but she didn’t ever come out. So I left and came here.”

“So that’s it?”


“You grinded, came, and that was it?”

“It was pretty hot.”

“Yeah, but…” Allison hems.

“That doesn’t really count.” Claire states.

“What do you mean? She was completely covered in my cum.”

The image of Allison writhing on the floor as he and James stood over her flashed in his mind. He imagined Jennie in her place as they stroke their cocks and cum on her pretty face.

“Still doesn’t count!” Claire said.

“What does count then?” James asked.

“Vaginal penetration.” Claire states. “Everything else is just… playing. Off the books. Doesn’t count.”

Really…?” James smiled.

“Really.” Claire said matter-of-factly.

“So handjobs don’t count?” James asked.



“Nope. Vaginal penetration only.”

“Hmm…” Brent smirked.

“Dare.” Claire said.

Brent and James turn their backs on the girls and whisper quietly. Finally, they return their attention to the girls.

“Now that we know what you consider sex… I dare you… to titty fuck James.” Brent said.

Whoa…” Claire laughed.

“It won’t even be… on the books. Doesn’t count. No penetration.” Brent smiled.

“I don’t… think that it’s… okay to…” Claire stammered.

Rules are rules.” Brent chuckled. He didn’t actually expect her to do it. He just wanted catch her off guard, even for a moment, to see where she drew the line. The look on her face was worth the effort.

Seriously. You want to take it there? It hasn’t even been a full round yet.” Claire crossed her arms.

Brent smiled.

Claire sighed. “Dare’s are one-on-one. James has to agree to it too.”

“I’m game.”

James! Claire gasped

“When my turn comes up, I was gonna choose dare anyway. This can be my dare too.” James said.


What? You two have been walking around… wearing tight little bikinis… looking all good… Seriously, a guy can only take so much!”

“I’m your sister James!” She did her best impression of an sister appalled at the idea of being sexually involved with her own brother. Allison saw right through it but said nothing.

The Oscar goes to…

“As far as I’m concerned… right now, you are a smoking hot blonde that I’m about to titty fuck.”

“Oh my God James. Seriously?” She groaned.

Rules are rules. Top: off.” Allison instructed.

“Oh, you’re gonna pay.” Claire almost laughed but maintained the facade.

Allison chuckled. “You’re the stickler for following rules.”

Claire hunched her shoulders in defeat and sighed.

She looked at James, snapped her fingers and pointed to the recliner.

James was genuinely surprised.

It was no secret that James was pretty shameless. In fact, he and Brent actually talked about titty fucking Claire in detail, as well as Allison, Jennie, and just about every girl in town with large enough breasts, but actually going through with it was not really in their realm of reality. James was even more surprised that Claire was not putting up much of a fight. It seemed to him, knowing her, that she gave in pretty quick. Then again, she was a stickler for rules…

Claire unbuttoned her blouse and tossed it onto the couch. Her breasts stretched the fabric of her white tank top. The blouse, as sheer as it was, was obviously necessary as her nipples were clearly visible without it. She quickly pulled it over her head in one motion and dropped it onto the soft carpeted floor.

Like James, Claire was lean with blonde hair and blue eyes. Unlike James, Claire was very much the embodiment of female sexuality. Her breasts were full, firm, and tipped with small pink nipples that, at the moment, were very hard.

“Don’t even think about blowing your load.” Claire instructed and she knelt between her brother’s legs. She hoped he couldn’t see the lust on her face. She wanted to maintain of doing this against her best wishes. She had an idea that this game could spiral way out of control if she let it, so a little restraint at this stage might be for the best.

She took a breath, exhaled, and leaned into him.

He couldn’t believe his beautiful sister was kneeling topless between his legs unzipping his fly.

He imagined what this would look like many times before. He pictured her big clear blue eyes looking up at him with his cock between her lips, feeling the vibration of her moan as her tongue slid along his length. He had thought about it, but never really believed it would actually happen.

Yet, here they were.

She pulled his shorts down his thighs freeing his rock hard cock.

Claire settled on her calves and took it all in.

Her brother looked down on her without a stitch of clothing on. His hard throbbing erection was inches from her face, twitching as he flexed it. She could feel the heat radiating off of him. She was actually doing this.

Brent and Allison sat in silence as this highly erotic scene between brother and sister unfolded before them. This is unreal, Brent thought to himself.

When summer started, he and James had pretty reasonable expectations. They planned to play some video games, watch some movies, swim, relax, and partake in their increasingly frequent jack off sessions whenever the desire arose. They hoped, but did not expect, to possibly find a willing sexual partner to experiment with. Never had they thought they would have two college girls within their reach, more than willing, one of which was James’s sister.

“Damn James. You have a big fucking dick.” Claire grinned and shook her head as she slid her fingers up his length. He shuddered with pleasure. She locked her eyes on his as she squeezed her breasts together around his throbbing cock. She slowly began to build momentum by flexing her thighs, rising and falling in his lap.

The sound of skin sliding on skin seemed amplified.

“We need some lube.” She said backing off. Claire took him in her hands and brought her lips directly over his cock and spit. She working in her saliva in a stroking, pumping motion. He could feel her breath on him. He pictured her full wet lips wrapped around him. Her eyes meeting his as her tongue explored.

“Fuuuck.” He grunted.

“There.” She resumed, squeezing her breasts around his now slippery cock.

“You are so fucking hot Claire.” He whispered. She smiled. In her eyes he saw a hunger he had never seen before.

He began to pump his hips, matching her rhythm. With each thrust, the tip bumped her chin. To her, it was as almost as if he was urging her to take him in her mouth. She knew that this was likely just her desires consuming the logical side of her brain, then again…

Her inhibition free, sexually hungry little brother just might want to fuck his sister’s mouth.

Maybe the taboo of incest was something he was willing to consider experimenting with. Maybe the idea of fucking his sister something that turned him on.

Maybe, like her, his sexual hunger allowed him the flexibility to do just about anything to bring him pleasure.

She licked her lips and was about to let him slip inside the warmth of her mouth when she remembered she had an attentive audience.

Allison was watching.

Brent was watching.

Oh fuck, what am I doing?

“Okay. Who’s next?” Claire said suddenly, rolling on her knees to a sitting position. Her back was to the couch, facing away from James. She slid her fingers between her breasts and spread her saliva until her chest was shiny.

She didn’t bother putting her shirt back on.

James didn’t pull his shorts back up.

The blush on Claire’s face said more than she wanted.


Claire smile broadly. “I dare you to play the rest of the game nude.”

“Um… wait, isn’t it Allison’s turn?” Brent stammered. Brent looked at James with his cock in his hand, Claire topless, and Allison with a robe wrapped around her staring into his eyes with a particular look on her face.

“Whip it out stud. Show us what you’ve got. If you’re anywhere as big as James, I wan’t to see it.” Claire instructed, gesturing to his crotch.

“How about Allison loses the towel? That way, it’ll be fair.” James offered.

My best friend, ladies and gentlemen.

“Hey! Those aren’t the rules.”

Claire gave her a look.


Allison pulled the tie around her waist free and dropped the robe onto the soft carpet. She stood before the three completely nude.

“Happy?” She asked with her hands on her waist.

The boys nodded in unison.

“Okay, your turn.” She said to Brent.

Brent pulled the button free on the front of his shorts and pulled the zipper down. He hooked his thumbs into the waistband of both his shorts and underwear and pulled them down together.

His thick erection angled upwards, long and hard like a totem to the gods of fertility.


“Wow.” Claire gasped looking from Brent to James and back again.

Amazing, Allison thought. Claire was well aware just how big they were. Yet, her reaction seemed like genuine giddy disbelief.

Allison on the other hand, was not the caliber of actress that Claire was. Instead, she stayed quiet and spoke with her eyes.

“Seriously, I don’t don’t think I’ve ever seen guys as big as you two before… definitely not at the same time.” Claire smiled. Allison nodded in agreement.

“You think?” Brent tensed his abdomen, flexing his engorged cock to full capacity. Every vein bulged, every ridge and valley were clearly defined.

James had seen this show many times before and never got tired of it. Over the course of the past year, he and Brent had met up to jack off together many times. This often took place in the small sliver of time after school and before his parent’s came home. Together, they shared technique, compared sizes, and often had contests to see who could cum the furthest, the most, the soonest, and so on. Seeing Brent when he was very horny was always impressive.

“Yeah, do doubt. You guys are big.” Allison almost whispered. Her eyes were glazed over.

“I dare you two to make out.” James suggested with a grin.

At this point, it was obvious that their little game of truth or dare was just an excuse to delve into increasingly sexual territory with little personal responsibility. Though they all understood this to be true, they continued to play along.

“Okay… If you two jack each other off while we watch.” Claire suggested.

“That would be so hot.” Allison said leaning into Claire and kissing her neck softly. She kept her eyes on the guys to gauge their reaction. If her instincts were right, all they would need was a little push.

They were speechless.

“I just titty-fucked my own brother on a dare, the least you two can do is give each other a hand.” Claire said before pressing her lips into Allison’s.

James and Brent looked down at each other. It would not have been the first time they felt each other’s cocks. However, this would be the first time they would do it with the intent of giving each other pleasure.

“Have you ever seen two girls make out?” Claire asked. She unbuttoned her jeans, pulled down the zipper and turned her back to them. She tugged the waist down past her perfect ass and paused. Looking over her shoulder, she delighted in their lustful expressions as their eyes molested her body.

“Well?” She said suggestively, pausing in this position.

James and Brent shared a look.

“It’ll be our little secret.” Claire whispered and she pulled her jeans the rest of the way down her long legs. She bent at the waist and arched her back. Her feet were far enough apart that when Allison slid her hands up her thighs, there was enough room for her to slip her palm between her legs and press her fingers into her soft mound. Claire let out a soft moan before Allison silenced her with a kiss.

James slid his hand to Brent’s cock and squeezed the firm head. Brent submitted and released his grip, allowing James to slide his hand down his length. He lowered his gaze and watched as James begin to jack him off. His fingers wrapped around his thick shaft and expertly stroked him with the right amount of pressure, at the perfect speed.

September 2018
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