The Jack Off Sessions Ch. 06

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.

---

"Truth."

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..."

"Climax?"

"Orgasm?"

"Cum?"

"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?"

"Yeah."

"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."

"Blowjobs?"

"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.

"Seriously?"

"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.

---

"Dare."

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.

"Fine."

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.

Silence.

---

"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.