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The Jack Off Sessions 4: The Aftermath

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By stiffpoles [Ignore] 15,Apr,21 06:33   Pageviews: 201

PART 1.

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 elegantly 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 other’s 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. They 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 reveled 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 have to tell you something. It is 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 other’s homes, they were all friends, and often spent hours in each other’s company almost daily. 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 placed 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. 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 wank sanctuary.

What she did not 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, its 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 like 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 wank 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 hometown, 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 like 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 countertop. 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 he is 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 extremely 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.

"So, we were thinking about renting a movie or something while we're out. Any requests?" Now leaning forward, Claire looked at the guys and smiled. Her breasts were large C-cups, not as big as Allison's, but they were still looked very full and juicy on her thin frame. Obviously uncomfortable, the guys tried their hardest to look natural.

"Uh, whatever you think looks good." James managed to say.

"Okay, then. We are off. We'll be back in a little while." Claire said getting up, Allison following her lead.

"Bye guys." Allison said, looking over her shoulder. The guys studiously watched as they walked away, looked at each other, then back at the girls.

PART 5: MALE BONDING

Peeking over the edge of the fence, Brent and James watched as Claire and Allison backed down the driveway. As the red VW Golf disappeared down the tree lined street, they dropped down onto the lawn and made a bee line toward the sliding glass back doors of the house. Neither said a word, it was just not necessary.

They weaved through the maze of boxes in the basement toward the clearing. Once inside, in the area between the small couch and television, they dropped their swimming trunks. Their eyes slowly adjusted to the poorly lit basement as they stood before each in the nude. Since their first stroke session, they had preferred doing so sans clothing. It made sense considering their affinity for lubrication and often explosive orgasms. Clothes would only get in the way.

Though the small basement windows high along the walls allowed some dim light to enter, the stacked boxes provided privacy and sacrificed illumination. After a moment, James reached into a box next to the couch and retrieved a beach towel and laid it over the cushions. He then pulled out a bottle of lube and dropped it on the towel.

Though Brent could barely see in the darkness, James's bare skin seemed to glow in the gloom as he went through the motions. He figured since James was the one that cleared out this area of the basement, he was probably familiar with the set up. Still, it was impressive how he knew exactly where everything was despite the lack of light. With a push of a button, James turned on the television. The clearing was immediately lit up with the static on the screen. James pressed play on the DVD player and movie began. James looked over his shoulder at Brent and smiled.

The two took their seats side by side on the small couch, James reached between them and retrieved the bottle of lube. In a single motion, he popped the top open with a flick of his thumb and squirted a long line of the clear liquid from the tip to the base of his shaft then passed the bottle to Brent. Already stroking his long, thick erection, he followed suit and squeezed a substantial amount on it just as James did. As they jacked off together, the tell-tale sounds of wet cocks being stroked was mingled with the sound of sex coming from the speakers of the television.

The brunette looked up at the two men as she took turns taking them into her mouth. As one cock slid out, it was replaced by another. Brent and James often watched this video and talked about being in the places of the men. As the scene played out, Brent finally broke the silence.

"Your sister is so fucking hot." Brent finally said.

"I know right? That little white bikini...mmm-mmm."

"How big do you think her tits are?"

"C cups for sure. They got bigger since the last time she visited."

"How about Allison in her bikini!? Her tits are fucking huge."

"I'm thinking she has D cups, maybe even double D's."

"Fucking hot. Both of them. Oh man, I got so hard when they came out."

"Me too." James slid his hand down to the base of his cock and squeezed. Every vein bulged. Brent did the same. Together they wagged their dicks in the air in mutual admiration.

Since they started jacking off together months prior, they often checked each other out. It seemed only natural to show off a little.

"Hey man, you think my dick got bigger?" Brent asked.

James looked up at him, then back down. Brent stopped stroking and held his dick out with the thumb and forefinger of his stroking hand. He flexed it, engorging it to capacity. The film of lubrication gave it a wet sheen. Every bulge and valley, vein and ridge seemed to be enhanced by the slick coating.

"Yeah man, it looks huge."

"Yours does too. Looks hard as hell."

"It is."

"When was the last time we measured, like two months ago?"

"Yeah, two, three months, something like that." James seemed mesmerized by Brent's cock. He sensed that turning the conversation to their erections would allow James to check him out in comfort, making him hornier. He spread his legs and pushed his hips out a bit. His thigh was now touching James's thigh, his smooth balls hung low, unrestricted. He slowly stoked, feeling his length slide beneath his grip.

"You got a ruler?" Brent finally asked.

James looked up at him, smiled, then reached over the arm of the couch and into the bag where their porn stash was located and returned with a 12-inch wooden ruler. Placing the ruler over his own shaft, James pressed the base against his pubic bone and flexed his dick.

"Just over 8 inches. Check that out. Half an inch bigger since the last time." James said. Holding his thumb, a little over the 8-inch mark. The thickness of his penis clearly showed the head passing the line.

"Dude, seriously? Nice."

"Hormone’s man. It has been a while since we measured. You were 8 and a half before. I bet you're over the 9-inch mark by now."

Brent took the ruler and placed it over the length of his shaft. He felt the warmth of James's cock on the wood. It made him rock hard.

"Damn." James said. "9 and a quarter." His eyes seemed focused on Brent's cock.

"Seriously, I wonder if I'm gonna get any bigger."

"For real. They say the average is like 6 inches."

"Shit, that just means we are hung as hell."

"Fuck yeah."

Brent passed the ruler back to James, who dropped it back in the bag. They continued stroking.

"I am hard as fuck dude." James said.

"I bet I'm harder." Brent replied.

Suddenly, James reached over and squeezed Brent's cock. Shocked, Brent froze. His hand stopped stroking as James wrapped his fingers around Brent's thick shaft with a firm grip.

"Damn dude, it's like it's made of wood. Check out how hard I am." James said jutting his hips out. His engorged member rested on his abs, balls hanging low.

Without thinking, Brent reached over and took it in his hand and squeezed.

"Hard as hell man." Instinctively his hand slid down the shaft and back up before releasing. He realized that James still had a hold of his. James reciprocated by pumping his hand up and down a couple of times before returning to his own.

The two refocused on the scene playing on the television.
The brunette was sandwiched between the men. Below her, one man pumped his dick in her pussy. Above her, the other man fucked her ass. She gasped and groaned as they slid rhythmically inside her.

Jacking off in relative silence, they quickened their pace.

"I wanna fuck your sister so bad."

"I wanna fuck Allison and cum all over her tits."

"We should fuck them together."

"Yeah man. Take turns." James grunted.

"Pass them back and forth. That would be hot."

"I know right. Claire's my sister, but damn. I have to admit, she does look good."

"It was almost like they were trying to make us horny."
"Maybe they were."

"I mean, jeez. Claire in that white bikini, Allison and her juicy tits in that little black bikini. I would do anything to see them naked."

"Both of them together would be a little hard to handle."

"I think we can handle it."

On the screen the brunette kneeled in front of the men as they stroked their cocks in front of her face. She begged them to cum as she fondled her breasts.

As if thinking the same thing, Brent and James speed up their pace and after a moment aimed toward their chests. Simultaneously, they released a torrent of cum all over themselves. Pulsing blasts of the sticky white fluid shot through the air, landing on their torsos, coating their bodies. They moaned as the hot aromatic seed shot out with an intensity they had never experienced before. Again, and again, thick ropes shot through the air, landing on themselves, dripping down their bodies and onto the couch.

As their balls emptied, they finally slowed their pace, panting, and finally relaxed. Their heads tipped back as their rigid erections softened while the cum drooled out and onto their thighs. They were sitting in a mixture of their own cum as the credits began to roll.

"Holy shit, that was intense." Brent groaned.

"I came so fucking hard, dude." James sighed.

They got off the couch before their hot cum completely cooled onto their bodies. James handed a slightly used towel to Brent to wipe off his bare torso, then used that same towel to wipe himself down. He dropped it onto the soaked beach towel that laid across the cushions of the couch and brought the whole thing up with them to put in the washing machine.

As he shut the basement door behind him, the only clue to what had just occurred lingered in the air with the thick scent of cum, sweat, and testosterone. The television was off, and the porn stash was safely hidden away. After the small puddles of cum on the floor dried and the scent dissipated, their tracks would be covered.

Between a couple of cardboard boxes next to the television, the strategically placed digital video camera hummed in the darkness.

... to be continued.

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Comments:
By #642923 [Ignore] 26,May,21 06:05
I'm oozing precum
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By Casius [Ignore] 17,Apr,21 15:02
Had my cock throbbing the whole time...got really wet too... just from reading... no manual stimulation.HOT
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By #339203 [Ignore] 15,Apr,21 17:59
So hot mate..
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By #552884 [Ignore] 15,Apr,21 13:01
Hell yeah good job Josh There really is no end to your talents You're breathtakingly hot, an absolute pro at getting the best out of that hot dick of yours and you write the steamiest hottest blogs on Syd!!
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By #570308 [Ignore] 15,Apr,21 08:55
How hot, good job...
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