The Jack Off Sessions Ch. 04

Part 1. The Aftermath.

Jennie looked at her cum covered body in the reflection of the bathroom mirror. She studied the way thick globs of the white fluid slid between her breasts and down her bare torso. Standing in nothing but her white cotton panties, she could not believe her appearance. "I look wild," she thought.

Her normally neatly styled brunette hair was now tousled, her cheeks were flush, her nipples were hard and she had the wet sheen not unlike being covered in an excess of tanning oil. Except, this was not oil. The slippery lubrication that coated her body was the hot cum of her longtime crush.

Though she had made out with guys before on a handful of occasions, never had she gone this far. She recalled the boyfriends that she allowed to suck on her breasts, finger her pussy, or grind their crotch between her legs through a barrier of clothes. The only orgasms during these rare events were all one sided, never hers.

She was never allowed the satisfaction of grinding with a guy until she came herself. Never had a guy slide his hot rigid shaft between her legs with nothing more than the thin fabric of her flimsy panties preventing penetration. Never had she felt a guy shoot cum all over her, the thick, hot liquid lubricating their bodies as they slid past each other, tongues intertwined, moaning into each others mouths with lust.

"Oh God," she thought, "Brent's cock is so big, hard and thick." Knowing him all these years, she had no idea what it would be like to be with him. Though she often fantasized about it, masturbated to the image of them together, watched him in the hallways at school from a distance, and talked about him to her friends often, she never thought anything would happen between them.

She thought about the way he looked under her, the look in his eyes as she grinded him with her throbbing pussy, feeling his hard dick between her thighs. It felt so good to cum. So, so good to feel the pressure build, and build, then finally release like a tidal wave through her body.

Feeling the heat between her legs intensify at the thought of what happened between them, she hooked her thumbs into her panties and quickly wiggled out of them. "You are such a nympho!" She giggled to herself.

She slid her hands over her breasts, spreading the hot cum into her flesh. Her hard nipples were sensitive under the pressure of her palms as a moan escaped her lips. More than a handful, her ex boyfriends all loved them. On more than one occasion, several suggested showing them off more. The would say things like, "Wear a tight top," "Show some of that awesome cleavage," "Let them breath sometime, babe." She was too self conscious to do any of these things.

Her sudden growth spurt not too long back brought about a lot of changes to her body, specifically a physique that looked more mature than she was comfortable with. This included breasts that seemed to be getting bigger as the weeks went on, often to the surprise of the handful of boys she made the mistake of getting involved with.

Normally she would do her best to hide her body. Stuffing her breasts in a sports bra, wearing baggy shorts, keeping her hair neat and manageable. Her look reflected practicality over the overt attempt to look desirable, unlike most girls her age. But, in this light, in this empty bathroom, cum coating her naked body, her hands squeezing her swollen chest, her shaved pussy moist with arousal, she revelled in her sexiness. She looked good, she thought.

"You are one hot bitch." She moaned as her hands lowered to her throbbing pussy.

Part 2. Poolside.

Brent floated on the surface of the pool in the inflatable plastic chair, his hands and feet dangled into the cool water. Behind his closed eyes he replayed the confusing events that took place earlier that day.

He had made out with his neighbor Jennie. He pictured the dreamy look on her face as they kissed, the taste of her lips, the feel of her hips rhythmically pressing against him. The curve of her ass under his hands, her soft breasts against his bare chest, the whole surprising afternoon stirred arousal in him as every moment played and replayed in his head.

"Dude, what's on your mind?" James asked, smirking. He was looking over the rim of his sunglasses gesturing towards Brent's swimming shorts. Lowering his eyes, Brent saw the obvious tent his erection made. He laughed.

"Man, I gotta tell you something. It's a secret though. So, you gotta promise to keep it that way." Brent said rearranging his shorts to hide his erection. This did not embarrass him in the least. Given the nature of their friendship, Brent felt fully comfortable around James, no matter what the circumstance.

"Lips sealed." James said making a motion as if to zip his mouth shut. He pushed his sunglasses up his forehead and focused his attention on Brent. He was floating nearby on an identical inflatable plastic chair.

"You know Jennie, my neighbor?" Brent asked, already knowing the answer.

"Jennie Connor, cute, brunette, lives right next door to you. What about her?" James replied in one breath.

Years prior, when they were kids and puberty was far in the horizon, James, Brent, Jennie, and a handful of other neighborhood children often played together. Whether it was riding their bikes in the streets of their suburban hamlet, exploring the woods on the outskirts of town, or playing video games in each others homes, they were all friends, and often spent hours in each others company almost on a daily basis. As the years passed however, some moved away, others found new friends, a few became preoccupied with personal interests. The large group became several small groups, in some cases just individuals trying to find their own way. Brent and James became closer, and hung out almost exclusively. Jennie, always a tomboy, found an interest in sports and friends in her teammates.

"Right. Well... we made out earlier today." Brent said quickly, almost blurting it out. He almost gave into changing the subject completely, thinking that maybe this was something he needed to figure out on his own before telling anyone else. But, this was James after all. His best friend since childhood. They knew each other better than anyone else. If he had not told him, James would have figured out something was up sooner or later. So, he decided to be up front and tell James everything. Maybe this way, they could make sense of the situation together.

Before James could reply, he looked up to see his sister Claire and her roommate from college, Allison, shutting the fence gate behind them. They walked across the backyard from the side of the house toward the pool. Holding shopping bags in each hand, they had obviously come back from a shopping trip.

"I'm glad you're home, I forgot my key." Claire announced as she approached the edge of the pool.

"Hey guys." Allison greeted them with a smile.

"Hey Brent." Claire said, giggling. The way she was looking at him made him feel self conscious. He brushed sweat from his brow.

"Shopping?" He managed to ask, gesturing toward their bags with a nod.

"Yeah, some supplies for the dorm, some clothes. Stuff like that." Claire smiled as she placing the bags on the pebbled surface bordering the pool. She bent her knees and leaned over, dragging her fingertips over the cool surface of the water.

She wore black shorts and a tight pink cotton tee shirt with a faded white crest of some sort across the front. Her blonde hair was pushed away from her forehead by white framed sunglasses that acted as a makeshift headband. Though her outfit was relatively tame, she made it very sexy. She was athletic and very fit, but had curves in all the right places.

Her blue eyes seemed to shimmer as she looked down at Brent. Her lips looked wet and juicy. The way she leaned over at the edge of the pool seemed to Brent as an offering, presenting herself to him. If only he had the guts to reach out to her. She almost pushed Jennie from his mind completely. Almost.

"You guys gonna be out here much longer?" She asked looking deep in his eyes, a slight grin on her face.

Brent nervously broke eye contact, looked at James, who looked back at him.

"Yeah, probably. What's up?" James answered looking back toward the girls.

"We were thinking about having a barbecue later on. You guys getting hungry?" Allison asked. She wore a form fitting short-sleeved plaid button up shirt and khaki shorts. The top buttons of her shirt were undone, revealing a white low cut tank top which sadly hid what would have been considerable cleavage.

Her body seemed barely contained by the fabric of her clothes. Her curves were almost extreme on her tiny frame. Shorter than Claire, she was very petite and very voluptuous. The delicate features of her face were betrayed by the overt sexiness of her body. The buttons of her shirt visibly strained to stay closed.

Standing next to Claire, the two, with their toned bare legs, thin waists, full breasts, and gorgeous faces, seemed like every teenage boy's fantasy, which, to Brent and James, was exactly what it was.

"Yeah, that sounds awesome." James finally replied, stretching on the floating chair. Though Brent was self conscious, James had no shame. He arched his back as he stretched, tensing and releasing the muscles of his body before settling back into the chair. He was noticeably hard and made no attempt to hide it.

"You need any help?" Brent asked the girls, trying to detract from James's obvious display of arousal.

"I think we got it. We'll get things set up." Claire said, as if not recognizing James's obvious hard on. She straightened up and picked up her bags. The two girls made their way to the back of the house in silence. Stunned silence, Brent imagined.

"Smooooth." Brent laughed splashing James with water.

"Dude, Allison is so fucking hot. It would be rude not to show my appreciation." He joked.

"You have no self control, man. Did you even realize your sister was standing right there next to her?" Brent asked.

Not responding, James pushed his sunglasses back down over his eyes and floated in silence.

"So, tell me about what happened between you and Jennie." James finally said after a moment.

Part 3. The Secret Lives of Claire and Allison

As Claire pulled items out of the refrigerator and placed them on the counter, Allison stood at the sliding glass door looking at the boys by the pool.

"Your brother..." Allison breathed, almost to herself.

"I know right?" Claire replied

"I have a thought." Allison turned from the glass toward Claire.

"Oh yeah?" Claire was bent at the waist into the fridge.

"It's so bad,.. but hear me out."

"Alright."

"So,.. you know how you said you watched them jacking off in the basement?"

"Mmm Hmm." Now smiling, Claire closed the refrigerator doors and leaned back on them crossing her arms.

The night Claire watched Brent and James jack off together, she found the clearing in the basement while looking for her High School yearbook. She was not sure what she had found at first, but the stack of porno magazines and DVD cases in the box next to the couch made it all too clear. She realized that this was the area her brother used to jack off in privacy.

It was isolated, out of the way, and relatively secluded. Her parents rarely went down to the basement. If they did, it was usually to add more boxes to storage rather than to dig anything out. If they did need anything, they usually sent James down to get it. If, for some reason, they did make a trip to the basement, odds are they would not have tried to explore the labyrinth of stacked boxes that eventually lead to the clearing with the couch and television: James's jackoff sanctuary.

What she didn't anticipate was that James shared this activity with anyone. Though, if he did, it would only make sense that he would do so with his best friend, Brent. Still, most of the guys she had been involved with treated masturbation as a private act. Only in the rarest of cases had she been involved with a guy that liked company while doing it, which usually involved her participation.

Until that point, she had not thought of her brother as a sexual creature. She had always thought of him as just her little brother, the kid that grew up alongside her; dorky and awkward. Now, however, she saw him in a whole new light. He was a young man, with lean muscles where there were none before, a handsomeness that reminded her of a younger version of her father. He had grown several inches since she last saw him, his baby fat burned off leaving chiseled features, and a quirky appeal that, on anyone else, she might be attracted to.

Of course, the most impressive feature that she had never noticed on her baby brother before was his nude body. Watching him from behind a wall of boxes, she saw him in the nude for the first time since they were toddlers. To her surprise, he was smooth shaven. This youthful hairless appearance was betrayed by his engorged cock. Thick and long, it's size was enhanced by the smooth surroundings. This was not the first time she had seen a guy shave his pubic hair. On the contrary, many of the guys she dated tended to groom down there. Several of which approached things just as her brother did by taking it all off. Though, never would she have imagined that James would have such an impressive unit. The lack of pubic hair gave her a clear view of it all.

Then of course there was Brent. James's partner in crime since childhood, she had known him for years. In their youth, she had always liked him. He was smart, funny, and seemed to have at least a few interests similar to hers. On more than one occasion, they had extended conversations about books and even loaned each other some volumes from time to time. She even found him attractive, in a young and cute way. This was, after all, her brother's best friend, and he was still a few years her junior.

However, in the basement clearing illuminated by the porno movie on the television, she could see Brent was no longer just the sweet kid she had grown up with. Like her brother, he was now a young man. Athletic and toned, he obviously worked out. Her eyes were immediately drawn to his sizable cock as he stood there in the nude. It was huge. At least an inch longer than her brothers, it was also thicker. Though he did not shave off all his pubic hair, he did groom it short. It then dawned on her that she had seen this impressive unit before. In the porno shop, earlier that day, she had sucked him off with Allison through a glory hole.

In college, she had immediately clicked with her Roommate Allison. They often joked they were "two peas in a pod." Within weeks they found that their friendship was special and unique. Allison, the more experimental and outgoing of the two, brought Claire along on her "adventures." There were many of them. Within weeks they had casually made out with each other one drunken night. Following that, they included one of their male friends into the fold. It soon became common to dare each other to participate in increasingly sexual acts that eventually brought them to a local adult bookstore. It was there that they found a thrilling outlet for sexual experimentation without strings, in relative anonymity, with the patrons of the establishments.

One of their special "adventures" involved a trip to an adult bookstore together with a small digital video camera. Finding a jackoff booth in the arcade section with a glory hole, they would record each other sucking the dicks of strangers. Having done this several times, they would watch the video later and make out to it. A quickly growing collection of digital video tapes was collected, documenting these acts, in a locked piece of luggage in the back of a closet in their dorm room.

The previous day, after immediately entering the city limits her Claire's home town, she suggested stopping off at a little isolated building called Wonderland, instead of heading directly home. Growing up, she knew about this bookstore located at the edge of town, but never had the guts to go there. With Allison by her side, she wanted to finally satisfy her curiosity. Inside she found a setup similar to the half dozen or so adult bookstores she had been in while away at school. However, it was in the booths that she experienced something different.

The length and girth of the penis that squeezed through the glory hole was impressive. Hard as carved wood, she and Allison took turns licking, sucking, and stroking it, passing the camera back and forth while the other serviced the engorged member. Using the skills she learned in college, Claire quickly brought it to orgasm, experiencing a flood of hot, sticky, sweet cum that filled her mouth. Swallowing almost every drop, she had not experienced such a powerful release before. This was indeed special. After draining it, she and Allison shared a deep, cum flavored, kiss in the darkness of the tiny booth, then promptly left. It was not until later that night in the basement clearing that she discovered that the well endowed stranger was none other than Brent, her kid brother's best friend.

"I can't stop thinking about it." Allison said in a dreamy voice, again facing the sliding glass door so close that her breath fogged the glass.

"It's so hot right? My brother and Brent, in the basement, completely nude, jacking off their lubed cocks together" Claire was looking up from the inventory on the counter top. She had stopped pulling items from the refrigerator and now shared the view of her brother and Brent out of the window. With one hand she kneaded her breasts, stimulating her hard nipples.

"I would never have thought that they would be into anything like that."

"When we were growing up, James wouldn't even take off his shirt when we went swimming. Now hes jacking off, butt ass naked, with Brent? It's crazy."

"Hot is more like it." Allison paused, then turned to Claire and continued, "I wanna see them do it."

"Of course you do." She laughed. "What did you have in mind?"

Part 4. A Plan Unfolds.

Brent and James looked up as the sliding glass door closed with a thud. Walking towards them over the lawn, the girls had altered their outfits. Though they still wore shorts, they both now wore bikini tops. Claire's was small and black, Allison's was white and even smaller. The guys watched them approach in stunned silence.

"Hey, so it turns out we're missing some things for the barbecue. We're gonna have to make a trip to the store in a little bit." Claire said. The girls lowered themselves to the edge of the pool. Together, they dangled their bare legs into the cool water as they sat on the pebbled concrete. Claire leaned back on her hands and arched her back. Her breasts heaved as she took a long slow breath, her head tilted to the sky. Allison looked down at her chest and fiddled with her bikini top .

"This is way too small." She mumbled as she adjusted the small pieces of fabric covering her obviously hard nipples.

Brent could feel his erection growing. Looking from Claire to Allison, and back to Claire, he shifted in the floating chair and tried to hide his arousal. James seemed to be mesmerized by the girls, particularly Allison. His eyes traced the curve of her breasts, watching intently as she struggled with the top. Looking at him, Brent could see that James was very hard as his shorts clung to his shaft.

"All of my bikinis are gonna look small on you. Your tits are huge, honey." Claire laughed turning her head toward Allison.

"Are my boobs too big?" Allison asked the guys. Leaning over, she squeezed her arms together, making her substantial cleavage much more prominent. The guys shook their heads and managed to mumble, "Nu-uh," "No way." She laughed and relaxed, her breasts bouncing back into their natural resting state. Though they were large D-cups, they still had a youthful firmness. Perfect, James thought to himself. Absolutely perfect.