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Author’s Note: This is a prequel of sorts. It covers Bob’s history and background. After the first few chapters, time starts whizzing by, as decades were covered. I recommend reading the first three Challenge stories as there are Easter Eggs, character cameos, and call backs to them in this story. The characters of Tiffanie and Diane will each have two stories — the first being an interracial one, the second being incest. Keep a lookout for those as Diane’s first story as it may be published by the time this one is — it’ll be under the Former Playboy Playmates series on my story listings page.
Editing thanks go to Todger65.
The Challenge 4: Origins and Revelations
He was going to take her. After weeks of watching her, studying her, memorizing her daily routine, Robby was going to hunt her down and take her. He didn’t want to do it, deep down, but his animal urges of being stranded with her, had become too much to resist. He hated the island, he hated how long they’ve been stuck there, he hated himself for even entertaining the idea of doing what he was about to do.
Robby watched her undress from his vantage point behind a cluster of palm trees. It was a full moon. The pale light was bouncing off her sweaty skin. She placed what was left of her clothing in a small pile. They were all but tattered rags now, her panties full of holes, her top shredded by a knife to use scraps of it as strings and ties. Robby watched her slowly enter the small pool of water at the base of a small waterfall.
He chastised himself for being turned on; he hated himself when he’d watch her work on the beach during the day, her tanned skin accentuating her musculature that was now visible due to massive weight loss. He would stare at the underside of her breasts and bare tummy while she carried coconuts. He would watch her hips sway when she surfaced from the ocean water with a fresh haul of clams, her light-brown hair slicked back, remnants of her shirt sticking to her skin. After weeks, Robby watched her, each day bringing him closer to taking her.
Masturbation only worked for so long. Robby would sneak off away from camp at night, jerking his cock behind a tree, or in the same pool area he just now watched her wade into. He felt more shame for cumming to thoughts of her. Over time, that shame faded, the desire for a real pussy milking his shaft instead of a hand coming to the forefront of his mind.
Robby’s desires multiplied tenfold when he caught her pleasuring herself one night. She had wandered off from camp and was gone for quite a while. There were no animals on the island that could hunt, kill, and eat a human but Robby thought there might be snakes or, in his most paranoid thoughts, a rat could bite her and infection could follow. He didn’t know for sure. He was concerned and told Cori he’d be back in a little bit.
Robby stopped dead in his tracks when he saw her, naked, in the pool, the small waterfall behind her, furiously rubbing her clit, moaning into the night. She was beautiful. Robby nearly came in his own tattered shorts, when he watched her turn around, thrust her hips forward, allowing the surging water to crash down on her pussy. It was nature’s own high-powered shower nozzle. He watched her shake and buck her hips, while holding on to vines on each side of the waterfall as the flowing water lapped at her pussy, causing her to scream out in orgasmic bliss, becoming one with nature.
The instant his hand grabbed his throbbing bulge, he ejaculated. After seeing that beautiful display, he started watching, planning and deciding when to take her. Robby considered the risks, thinking that maybe she’d understand given their situation on the island.
Watching her bathe, running the water through her hair, over her medium-sized breasts, and over her hips, he began getting aroused. Robby watched her turn to the waterfall, her lover, and smile, extending her hand to it, considering on making love to it once more. So many nights on their three months on the island, the flowing water of that little waterfall, unknowingly brought her so many orgasms. Tonight though, she decided not to treat it to her body. Slinking out of the water, as clean as a soap-free bath could get a person, he made his move.
It was his 18th birthday and this would be his present to himself.
Robby looked back toward camp and then around him to make sure Cori wasn’t near. He pulled off his tattered shirt and shorts and rushed to her, grabbing her tightly from behind, and as gently as possible guided her to the sandy ground.
She cried out, startled by him, “Robby!”
The side of her face in the sand, she tried pushing herself up and him off her, but he was too strong. He flipped her over on her back, “Robby! What are you doing?!?” Her were arms flailing, attempting to push him away, his face wrought with hunger and desperation.
As soon as she figured out what he was doing, feeling a hard cock against her tummy, as he etlik escort struggled to move downward to enter her, she relaxed slightly. “Robby, no. No. Don’t do this,” she pleaded in a stern manner, her legs attempting to push him off at his hips.
“Robby, no!” She said again sternly. Robby managed to push her legs apart and slam himself down. “Robby, you don’t need to do this,” she said, almost calmly.
His head was resting on her shoulder, his hips thrusting away, trying to find a way in to her, “Robby please.”
She was struggling, moving from side to side, her legs unable to push his weight off her. Robby found his way in; finally, he pushed in all the way, listening to her groan. “No!” she cried out.
Robby pinned her hands down, and was thrusting away manically with no order or pattern. He peered into her eyes, his own eyes apologizing for doing this, for taking her. She looked at his eyes, her face wincing from discomfort, her eyes not showing anger but sadness and empathy.
When it was done, Robby filled her with semen, collapsing on top of her. They began crying. He was crying because they were still stuck on the island with no idea of when, or if, rescue would arrive. He was also crying because of the overwhelming guilt that now flooded him.
“I’m sorry, I’m so sorry,” He pleaded in between sobs.
She sniffed, her body relaxing, her hands running through his blonde hair. “Shhh, it’s ok,” she sighed. She let him do this; she could’ve resisted more, but chose to allow it to happen.
Robby sobbed uncontrollably at his actions, he did not suspect the guilt would be this bad, “Please forgive me.”
“Robby, just stop, it’s ok. Alright, just relax,” She comforted him, her hands trailing down his back.
Robby sniffed a few more times, propping himself up on his elbows, looking down into her loving eyes, “It just came over me, and we’ve been here so long, and I — “
“Robby, enough, it’s fine,” She said, caressing his face. “It’s over and done with.”
“I’m sorry mom,” Robby said, calming down, his breathing returning to normal.
Robby’s Aunt Cori greeted them when they returned to camp, “Where’d you two go?”
“Went for a walk,” Robby’s mother, Karen, answered before Robby could say anything.
“Ok, well there’s some of that fish left if you two want to split it,” Cori nodded in the direction of the large fish they had captured. It was rare, but a beautiful thing. In the three months they’ve been there, they’ve managed to catch maybe five good sized fish to cook up. Coconuts, clams, oysters, and an occasional trapped lizard usually consisted of their meals.
Karen sat next to Robby on the log by the fire, her arms entwined in his. He took a couple bites and offered it to her. Opening her mouth, he slid a piece in, her lips tracing his finger. Sitting by the fire, stoking it, putting more wood on it, Robby calmed down. He shook his head at their situation.
“Mom, I’m — ” he whispered before being interrupted. Cori had fallen asleep.
“Robby, I said forget it. It happened, it’s done. Alright?” Karen whispered back, leaning her head on his shoulder.
“I’m sorry if I hurt you,” Robby sighed.
“It was a little uncomfortable,” Karen said, patting his forearm. “Don’t worry about it.”
Robby’s risk paid off, his mother wasn’t too angry, she understood, knowing his teenage hormones pushed him over the edge.
A couple hours later, Robby began getting sleepy, his eyes heavy. He felt his mother slip out from under his arm. He lowered his head to his knee, resting it on his forearm. He a few moments later, just before sleep began to take him, he heard his mother clear her throat from somewhere behind him.
Robby turned to the direction of the sound behind to see his mother nude, the light from the fire illuminating her skin. “Robby, let’s go back to the pool.”
They became one with the water, one with each other, mother and son giving everything to each other. Robby stood in the shallow pool, his mother’s legs wrapped around his waist, the waterfall behind them. He pumped upward, slamming into her, grunting as he worked. Karen moaned, her mouth hanging open, her hands clasped behind Robby’s neck. Peering into each other’s eyes, they climaxed together this time.
Karen slowly turned to her former lover, the waterfall; as if to tell it she had a new lover, a human this time. Her orgasm built up, surging through her spine, her arms wrapping around Robby, pulling herself against him.
Night after night, they met after Cori went to sleep. Night after night, in the pool, making love, the jealous pussy-licking waterfall, watching on silently. After a week, their love making sessions included a morning bath, another week, and Robby mounted her from behind while she held on tightly to a coconut tree, both shaded from the burning noon sun.
It was only a matter of time on that little deserted island that Aunt Cori would discover etlik escort bayan them.
Cori and Karen slammed Robby against the waterfall, attacking him with kisses, licks, and sucks. It had been three days since Cori found her sister and nephew in the throes of passion. Getting back to camp before they did, she waited. When they finally arrived, Cori stood, removed her ragged clothing and presented herself to them, silently asking them to be part of their new relationship. Karen and Robby stood, not saying a word, and removed their own clothes. The three of them had been naked ever since.
Robby was exhausted, pleasuring both women every chance he got. Gathering wood, coconuts, and clams took longer due to having to stop to tend to one of the women’s needs. He loved it.
A few weeks passed, Robbie sat at the camp one night, watching his mother and aunt. They stood facing each other, holding hands, their bodies nearly silhouettes due to the fire behind them.
Robbie watched them become one that night. He moaned as their first kiss ended, their tongues recoiling slowly back into their mouths, leaving a string of sparkling, fire lit saliva between them.
The two sisters went at it for hours, exploring each other’s bodies, grinding their pussies together, ending their session by swallowing Robby’s seed after a lengthy blow job. Robby smiled, looking to the starry sky, while his mother and aunt, kissed once more, sharing his semen.
Robby was the king of that island, his mother and aunt, his queens. He hoped they would never get rescued.
Six months since the pilot in one of Robby’s father’s private planes had a heart attack during flight, his arm banging the control wheel, changing its course during his death throes, inadvertently guiding them into a south Pacific storm. Robbie, recalling flight lessons his wealthy father purchased for him was able to crash the plane on a nearby island, without causing any injuries or death.
The three lone survivors walked along the beach, watching the sun set in the distance. They were naked as usual, holding hands, and chatting about old times before the crash. The feeling of euphoria Robbie was feeling by holding his mother’s hand to his right, and his aunt’s to his left, was brought to a deep low when his mother spoke next after a pause in the conversation.
“You know Robby,” She sighed, turning to face him, “If we ever leave this place, we can’t continue what we’ve been doing.”
“What?” Robby asked.
“I think you know what I’m talking about. The three of us, here, alone, this relationship we’ve had. It can’t continue if we are found. I’m married. Your father, he could never know about this.”
“I thought we liked it,” Robby said, turning to his aunt, “right?” Cori smiled and nodded politely.
“We do like it. But it’s wrong, it’s not natural. We’re just scratching an itch by doing this,” his mother explained.
“Well can’t we keep it a secret? We don’t have to stop, let’s just keep it a secret you know?” Robby pleaded, his voice trembling.
“No, Robby,” his mother sternly said. Cori slowly nodded in agreement.
“But — “
“Don’t make this difficult. I know you know it’s wrong. We all do. It’s fun for here, but it can’t continue back home,” Karen said.
“Robby, we may not ever get off this island, so who knows. It could be years. You might be sick of us by then,” Cori laughed, Karen’s younger sister attempting to dispel the tension.
“Yeah, I guess,” Robby sighed once more. His mother took his hand, his aunt never letting the other go, and they continued their walk.
A week later, Robby’s worst nightmare came to fruition. He had been ferociously feasting upon their pussies, when, after their climaxes, they pushed him down on the beach, mutually jacking off his cock, while their tongues entered his mouth. Karen heard the plane first. She ended her kiss, her saliva hanging off her chin into Robby’s mouth, Cori sucking it off her sister’s chin.
“What is it?” Robby asked, sitting up, his aunt kissing her way down his body.
Karen said nothing, immediately standing, sprinting back to camp, searching through the salvaged survivor kit. “What is it?” Robby yelled.
Cori was moaning, slobbering all over his cock, Robby watching his mother sprint back to him, handing him a flare.
“Get off him!” She yelled at Cori, pushing her away, her drool covered chin dripping saliva onto her breasts.
Karen pointing to the distance, “Go!”
Robby hesitated, knowing what was happening, but not wanting to follow their plans. He wanted it to fail. Shaking his head he listened to his mother and sprinted off to the other direction, 50 yards away at the end of their section of beach. Karen sprinted back to camp and shot off her flare, waiting for Robby to do this same for his.
“Do it!” She yelled, waving her arms at her son. “Now!”
Cori was with Karen now. She escort etlik didn’t want their time to end either. Robby looked to the flare, shaking his head, he wanted to stay a king forever. He couldn’t do it.
“Robby! Now!” Karen screamed at him from the camp. Cori looked on, tears filling her eyes.
The plane got closer, Robby wasn’t sure it saw the original flare; hence their back up plan to shoot them off in two different locations not far from each other, in hopes it would cover more visual ground. He thought about his 35 year old island queen, his mother, his time with her ending. He looked at his 30 year old, younger queen, his aunt. She was on her knees, crying, not wanting this to end either, but knew it had too.
“Do it!” Karen screamed, starting to sprint toward him. Robby looked to the sky, the plan much closer now, and decided to the right thing.
Cori rested her head on her nephew’s shoulder, sitting across from Karen. They were in their tattered clothes once more. Karen and Robby stared at each other from across the loud plane, angry at each other, but each for different reasons; Robby, because their erotic lifestyle was over, and his mother because Robby nearly failed to follow through with their flare plan. In Karen’s eagerness, she fired her flare too early; Robbie fired his just in time. If he had hesitated the plane might’ve flown by, leaving them both as failures.
In the decades that followed, he knew that if he did fail to act and they were stranded longer, their sexual escapades might’ve ended due to resentment on his mother’s part. On the plane ride back home, young Robby, accepted his fate, but it didn’t mean he wouldn’t try to take her again.
She slapped him hard. Robby was shocked. It was two weeks upon their return, Robby tried to hug her from behind, placing his hands on her stomach, over her dress.
“Mom, I — “
“Don’t touch me!” she sneered.
“I was just going — “
“I’m pregnant,” Karen started tearing up. “You piece of shit,” She pushed by him, disgusted at herself and by him. She was very angry; perhaps assuming her age and malnutrition on the island would prevent her from becoming pregnant. Those few fish they ate must have provided enough protein to sustain her monthly cycles.
Later that night Robby heard his mother and father making love. Shaking his head, he realized it was so she could trick his father into thinking the child was his.
Due to some bribery by his father, Robby was able to go to college on time. He excelled at Harvard Business School, several hundred miles away. When he came home for Christmas Break, he found a very pregnant mother.
He avoided his parents as best he could, his heart hurting from desire, obsessing over his mother’s pregnant belly. They hardly spoke.
The night before Robby was to return to school, he stood at the side of his parent’s bed, watching his mother sleep. Thinking about their time together on the island, wishing he could feel her, caress her, make love to her once more. He slowly slid her bed sheet down her body. Her pajama top was too small and her large belly was revealed. Robby gritted his teeth in anger, knowing that was his child in there, not his father’s. He reached into his pants, fished out his cock, and slowly began pumping it, angrily slamming his fist to the base of shaft. He thought about how good she felt, how sweet she was to let him have her on the island, but at the same time, how cold she’s been since their return. Decades later he realized she felt guilt and pushing Robby away was how she dealt with it.
“Ahhh,” Robby moaned in his parent’s bedroom, spraying her pregnant tummy with semen. He shook his head, buttoned his pants, and went to bed.
Karen sat up, her fingers touching Robby’s cum on her belly. She took her fingers to her mouth, licking them clean. She cried herself to sleep that night.
During his spring break of his freshman year, the 19 year old Robby arrived to another cold reception at home. His father didn’t notice or care. Robby tried to be pleasant around his mother, hoping that maybe she would snap out of this funk she was in.
The begging and pleading began a couple days before class was starting back up.
“Robby, I said no,” Karen was trying to be nice, having felt guilt for her harsh words shortly after their return from the island.
“Please? Dad won’t be home till later,” Robby pleaded.
“No!” Karen firmly said, pushing Robby off her and waddling away. Before she waddled to her bedroom, Robby grabbed her, spinning her around and slamming her against the wall. He kissed her hard, taking her by surprise.
“No Robby,” She pushed him away, he grabbed her face, staring into her eyes.
“Please, I need you,” He begged.
“No! Get away!” Karen was able to push him and waddle a few steps, her huge belly slowing her down.
Robby lunged at her, picking her up, and slamming her on the bed, not caring that it could disturb her huge pregnant mass.
Karen slapped him again, angrily looking into his face. Robby pulled her dress up, pinning her down as best he could with one arm. She remained still, slapping him once more, when he slid off her panties and began to guide himself in.
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