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The Challenge Ch. 08: To The Haven

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Author’s Note: This is the final chapter of my Challenge series – another one where everyone has sex with everyone. Many of the characters are already in secret taboo relationships with close family members. Below is a list of stories you may want to check out before or after reading this one. I explain which characters are established etc.

1. “The Long Absence: Allen’s Story” – introduces Robin, her daughter, Krista, and her grandson, Allen. Bob appears there too.

2. “Denise’s Year” – Introduces Robin’s other daughter, Denise. Reading that will explain how Denise ended up with her son.

3. “The Long Absence: Ted’s Story” – involves Robin’s youngest sister, Nikki, explaining how she ended up with her son, Ted. It takes place during the same time as this Challenge story.

4. Other related reading (though not as important) is: “Dahlia and Darren,” “Former Playmates Pt 3: Diane and Son,” and “Juicy J.”

Finally, cameos of the other families from the previous Challenge stories appear in this one too.

This piece also explores the relationship dynamic between a mother and son with the theme of unconditional love. Most of it is my opinion, of how I imagine things would be in reality. As a result, this story contains a parent and child having sex with other people for various reasons, after their incestuous relationship was established.


The Challenge 8: To The Haven

Chapter 1 – What About Bob

Bob pulled his fiancée, Robin, closer against him on the couch with one arm, his other pulling in Robin’s younger sister Joanne. “Why don’t you two young ladies go ahead and suck my dick right now,” he joked on the last evening of his week-long visit with Robin.

“Bob!” Robin cried, swatting at his arm. “You’ve had a bit too much to drink for tonight.”

“Yes, and we aren’t exactly young,” Joanne said.

“Well you certainly look it,” The 70-year-old Bob smiled appreciatively at his 62-year-old wife-to-be. Robin looked far younger with dark brown dyed hair, amazing body, large breasts, and very few wrinkles.

“You too,” Bob glanced at Joanne. She was 52, had equally thick, luxurious dyed brown hair, few wrinkles, and like Robin, a body some women in their 30s would love to have.

“At my age, an erection should never be wasted,” Bob pulled them in closer, their large breasts smashing into him, his hand traveling down Robin’s back, cupping her toned butt.

“I think that’s a great idea,” Joanne said, catching Bob and Robin by surprise.

Robin coughed, “Uh, you aren’t actually thinking about – “

“Going to see Krista while you two have some alone time? Yes,” Joanne said, removing Bob’s hand from her hip, bending down to put her shoes on. She hadn’t had any wine and could easily drive the few miles to visit her niece, Robin’s daughter Krista, for a little while.

Joanne shook her head, backing out of Robin’s driveway, thinking about how silly Bob was sometimes. There was something off-putting about him though. She couldn’t put her finger on it, assuming she didn’t know him well enough.

Joanne arrived at Robin’s seven months earlier, in January, seeking asylum after her marriage fell apart. Joanne has thoroughly enjoyed living and reconnecting with her older sister. Joanne’s niece, Krista and her son Allen, had recently moved back to town after a brief tenure living in another city due to work. Joanne always thought of Krista as her favorite niece and was glad to live closer to her now.


“AH!! Yes!!” Krista screamed and bellowed her answer to her son, Allen, simultaneously cumming again on his cock.

“Who?” he grunted back, on top of her, slamming into her, their bed banging against the wall. They were playing a game. Allen would ask his mother about her sexual past during sex and “punish” her either through royally fucking her, or a far more torturous method he sometimes used.

Krista was too busy climaxing to answer right away, her eyes rolling in the back of her head. Allen stopped his powerful thrusts, giving her time to calm down. “Who? What family member, other than me, have you fantasized about having sex with?” he calmly asked, catching his breath.

Krista panted heavily, smiling up at him, caressing his face. “Joanne,” she quietly whispered.

“Really? Your aunt, huh?”

“Mmhmm. I always thought she was gorgeous. Her breasts were, and possibly still are, very impressive. Nothing ever happened of course, but in my teen years I’d pretend that she would be my first lesbian encounter during a few of my masturbation sessions. That’s all that ever became of it,” Krista explained.

Allen smiled down at his lover, kissing her forehead, “That’s kind of cute, I guess.”

“Aren’t you going to punish me?” his mother asked.

“Oh, right, yeah,” Allen replied, his mouth going to her neck, pretending he was taking a bite out of it. Suddenly the doorbell rang. Krista’s eye shot open.

“Quick, go to the shower!” she told her son. Krista hopped off the bed, grabbed a bathrobe, güvenilir bahis and closed the bathroom door, hiding Allen in there as he started up the shower.

“Oh hi!” Krista said to her aunt, Joanne, greeting her at the door. Her face was slightly flushed and her hair disheveled due to the hours of sex with Allen.

“Hi!” Joanne replied, stepping in and giving Krista a hug. “Hope it’s ok that I dropped in.”

“Oh sure, it’s no problem at all, come in, have a seat.”

“Are you sure? Looks like you are getting ready to go somewhere,” Joanne noticed, sitting on the couch across from Krista.

“Oh yeah, no, I’m not. I’m waiting for Allen to get out of the shower. He has a date tonight,” Krista said. This was a true statement and a girl Krista handpicked for Allen to date, in order to throw people off the scent of their secret taboo relationship. The girl was nice, but it was all a sham, orchestrated by mom and son.

Joanne and Krista chatted briefly about mundane things, Krista occasionally glancing at her aunt’s cleavage, giggling inwardly at herself over what she admitted to her son during sex.

“Have you noticed anything unusual about Bob?” Joanne asked after a moment of random chit chat.

“Hmm, no, I don’t think so,” Krista replied, gulping, looking to her side. “What about him?”

“I don’t know. He seems very sexual and flirtatious. It just makes me wonder if he’s completely faithful. He’s got all that money you know. Maybe I’m just paranoid after what happened with my ex-husband,” Joanne shrugged.

“Bob is quite a character, but I think he’s just having fun with his jokes and flirts. But as a randy old man, who knows? He may be having fun on the side. My mom might even be ok with it,” Krista said.

Just then Allen appeared, dressed and ready for his date. He nodded at Joanne and feigned nervousness, asking his mother how he looked, if the shoes were ok, if the shirt was right. Krista played along, acting motherly, saying her son looked great.

Allen waved goodbye to Joanne, Krista walking him to the front door. Hugging her son, she whispered in his ear, “Try to save some cum for me to suck out of that big dick of yours later tonight, sweetie.”

“Ha, ok mom, I’ll try,” He kissed her on the lips and left.

Returning to the living room, Krista smiled at her aunt, “I’m going to grab that shower and I’ll be right back.”

“Oh, I can come back later if you want, I didn’t mean to barge in,” Joanne said.

“No, please stay. He’s going out on a date, so maybe you and I can have our own date,” Krista smiled, thinking about her teenage crush on her aunt.

Joanne chuckled, “Ok sure, that sounds great. It’ll be the first date I’ve had since leaving Tony!”

Krista turned, making her way up the stairs, disrobing as she was half way up. “Two secret relationships to maintain? No thanks! She’s probably not even bi-sexual anyway,” Krista thought to herself.

When her hand brought about her own orgasm in the shower minutes later, aided by thoughts of her aunt, she couldn’t help by laugh at her silliness. “I haven’t thought of her like that since before college!” she said to herself.

Chapter 2 – His Final Challenge

“Uh! Ahh! Yes!” Robin was grunting every time she bounced up and down on Bob. She was straddling him on the couch, riding his cock like a teenager.

Bob gritted his teeth, squeezing one of her massive melons, “Yes! Ride it baby!”

“I’m cumming!” Robin cried out. Bob grabbed her ass, squeezing it as his own orgasm approached.

Bob moaned, filling her womb with semen, Robin shaking with pleasure, “That’s it, yes, baby.” He kissed her lovingly as their orgasms subsided.

“We really need to get your sister in on this,” Bob said, he wasn’t joking.

“No, I don’t think so,” Robin rolled her eyes, getting off him, cum dripping out of her pussy. She stood in the kitchen, pouring more wine.

“What if I paid you?”

“Paid me for what? And why?” Robin asked.

“What if I paid you,” Bob said, turning around to face her from the couch, “a large sum of money to seduce your sister which would, in theory, lead to the three of us having many incestuous sexual romps.”

Robin burst into laughter, “Ok, Bob, sure!”

“I’m not joking. Do you know how erotic it would be to see you and your sister having sex in front of me? The three-way aspect would be nice, I suppose, but just to witness you and her together. Wow.”

Robin shook her head, taking her seat next to Bob on the couch, both still nude. “I think you’re losing your mind.”

“Robin, what if I gave you $45 million dollars to have sex with Joanne. This would be in addition to the $30 million dollars I have in my will for you, amongst other things,” Bob said, gently caressing her hand.

“Bob, no, that’s silly.”

Bob nodded and stood, walking to his duffle bag in the bedroom, pulling out a device that looked like a web camera.

“See that?” he placed it gently on the couch cushion in between him and Robin. “It would türkçe bahis record it. Set it up. Then you can record it with this, or this option here,” Bob pointed to a button on the side “would allow you to live stream it to my computer. In the event I’m in Atlanta if it happens. This way I would have proof of it happening.”

“Bob, I don’t know what to say,” Robin replied skeptically. “You’re serious about this?”

“I am.”

Robin chuckled again, “You’re weird. No thanks.”

“Suit yourself, I’ll leave this here,” Bob said, a sneaky smile appearing on his face as he grabbed the remote control. “I’ll also provide you with any resources you may need to accomplish this. Clothes, gifts, vacations with her. Whatever you need. When you and Joanne go to the Bahamas next month, you could become intimate there.”

“Great idea. Joanne and I going to the Bahamas. But your ‘challenge’ is pretty ridiculous,” Robin said.

Robin couldn’t believe she had just been challenged that. He was actually serious. She thought about why, wanting to ask him, but was too embarrassed for both of them. They sat in silence watching TV for the rest of the evening. Her mind was racing as one show ended and another began. Incest was something she had no experience with, though watching her hunky grandson, Allen, grow and mature, occasionally having inappropriate thoughts that were quickly vanquished was all she had ever done. She wasn’t a lesbian or bi-sexual, actually having sex with Joanne seemed so wrong.

As the night progressed, she wondered more about Bob. Was he a sexual deviant? Did he have a secret life? Was he visiting hookers? Robin felt very uneasy at bedtime.

Chapter 3 – Telling Joanne

Joanne and Krista were asleep on the couch, the movie they were watching was almost over. Krista was lying against her aunt’s shoulder. Joanne had her arm around her niece. Both women stirred when they heard Allen get home, stretching, smiling at one another.

Allen didn’t bother coming to say goodnight. Instead he went straight to his and his mother’s bedroom, stripped naked, and waited for her.

Krista chuckled, listening to Allen climb the stairs, “Must’ve been a bad date.”

“Yeah, poor guy,” Joanne chuckled back, grabbing her purse and keys.

“Our date was fun, even if we did fall asleep,” Krista joked.

“Yes it was! Walk me out?” Joanne asked. Krista giggled, bending and extending her arm, her taller aunt sliding her hand through it.

Standing at Joanne’s car, Krista hugged her aunt. “I had a wonderful time tonight. I think we should do this again sometime.”

“You know, I think that’s a great idea!” Joanne said, pulling Krista in for another hug.

“I know I haven’t mentioned this before, but I’m so sorry about what happened with your marriage,” Krista said, brushing a lock of brown hair behind her aunt’s ear.

“Oh sweetie, thank you,” Joanne smiled.

“I’ve always thought you were so gorgeous. You really are so very beautiful,” Krista smiled softly at her.

“So are you,” Joanne smiled, touched by her kind words, pulling her niece in for another embrace, ending it with a slow kiss on the cheek. “I’ll see you later.”

Krista waved goodbye as Joanne backed out of her driveway . Turning to go inside, she giggled at herself once again, blaming Allen for asking that question during their sex game. She closed the front door, locking it, then headed upstairs. She was naked by the time she reached the top step.

“You know I ought to punish YOU tonight. You asked me about family members other than you, that I fantasized about. Well Joanne happened to show up and I luckily didn’t do anything stupid. Having to have two secret loves would be really difficult,” Krista explained.

“Yes it would. For now you’re stuck with just one, me,” Allen said.

“What about you? What other family members have you fantasized about?” Krista asked, climbing on the bed, grabbing his erection.

“Someone I spent most of my childhood and teen years with while you were working or out with friends,” he answered immediately.

“I figured as much,” she chuckled. “Your grandmother is quite a knockout for someone her age.” Engulfing his cock, slobbering all over it, they began their marathon nightly sex session.


“HE WHAT?!?” Joanne whisper yelled at Robin after she was told of Bob’s insane challenge.

“Shhh, yes, he’s serious,” Robin replied. She was sitting on the edge of the bed in the guest bedroom Joanne had been staying in. Bob was asleep in Robin’s bed.

“You told him no, right?”

“I did,” Robin confirmed.

“That’s a lot of money, but that’s still very strange.”

“I know it is. It makes me wonder about him too.”

“How so?” Joanne asked.

“He is rich, he challenged me to do this, I don’t see him everyday, and he could be up to other perverse activities in Atlanta. Who knows,” Robin replied. “He’s always been flirtatious, but it’s always been in good fun. Challenging me to commit, um, incest, that’s a little extreme.”

“Yeah güvenilir bahis siteleri really,” Joanne rolled her eyes. “When does he go back?”

“Tomorrow. I can’t help but wonder though,” Robin looked away, shaking her head. “It’s just so bizarre. It’s like I thought I knew him. Some screws would have to be loose for him to challenge me to do this.”

“How much money did he offer?” Joanne asked.

“$45 million.”

“Wow. That’s a nice chunk. But still you’ll get money when he dies, right?”

“$30 million.”

“So a total of $75 million if we did this. Hmm.”

Robin looked at her sister skeptically, “You aren’t thinking about going through with it are you?”

“No, it’s just, that’s a lot.”

“I wonder if he’s giving money away to other people too. He seemed like he had it figured out, even providing a camera of sorts. He said I could keep it and film us doing it so he’d have proof.”

“Ok that is odd. If he’s that prepared, then something is definitely going on that you don’t know about,” Joanne said.

“How do I find out though?”

“If you had a spy of sorts that can relay information to you about what he’s up to, that would be ideal,” Joanne suggested.

“Yes it would,” Robin smiled. “They could go to Atlanta and maybe snoop on him. Who knows? If someone worked for him they could keep an eye on him. If they got close enough, they could really gather some great intel!”

“Who though?”

Robin answered immediately, “Krista.”

Chapter 4 – Asking Krista

Krista and Allen’s bedroom was dimly lit with candles. Allen was sitting in a large chair in the corner. His beautiful mother was straddling him, his cock embedded in her all the way. The silk, black tie of her robe was loosely tied around her neck. The robe discarded, lying on the carpet next to the chair.

Allen gently tugged on the tie, pulling her head back, arching her neck to him. He slowly kissed and licked along it, sending shivers down her spine, causing her to moan, torturing her. He was playfully interrogating her about her past sex life again a few nights later.

“You’ve been with eight women, huh? That’s a lot, I guess,” He shrugged, resuming his kisses, his mother’s eyes to the ceiling, fluttering shut when his lips made contact to her neck. He released his pull on the silk.

“I suppose,” Krista smiled at him. Running her hands over his muscled arms, she kissed his lips, savoring his taste.

Allen broke the kiss, “What’s the youngest guy you’ve been with?”

“It was over 10 years ago. He was 19. He was home from college for the summer. I worked with his stepmother. She admitted to me that he and she had been having a sexual relationship for a few years. She invited me over. I knew why. The night was spent with the three of us in bed. Then next morning it was just me and him. His name was Ulysses,” Krista explained.

“Very bad,” Allen teased, pulling the silk tie back once more, his mother arching her neck for him. He licked and kissed all the way from her nipples up to her jaw line. She shivered as the tingles went down her spine to her ass. The upward thrust of his cock nearly caused her to climax once more.

“Anyone else worth confessing?” He asked, ending his pleasurable torture for a moment.

Krista paused, glancing to a burning candle next to the bedside table. She thought about her younger years, she thought about the company she used to work for, she thought about the man she used to work for. Brief images flashed in her mind of his huge master bedroom, a roaring fire in the fireplace, his king sized bed, the silk sheets she gripped while her pussy was eaten out, lowering herself on his cock, crying out with ecstasy.

“Bob,” she said.

“Huh? What about him?” Allen asked of the man his grandmother was engaged to.

“Bob,” His mother said once more, a slight smile appearing on her face.

“You mean, you and him? You worked for him and – “

“Yes. When I was in Atlanta on business, we’d have meetings, afterward he took me to bed,” Krista explained, caressing her son’s face, moving her hands over his neck, and arms.

“Does grandma know?” he asked.

“No. Bob and I played it off like we never did anything. He’d flirt with me and I’d flirt back. It made things come across as though we never did anything – like it was all just playful fun,” Krista explained.


“Yeah, I was a very different person back then. But you are all I ever need and want now. You feed my addiction,” she said, kissing his lips.

Allen smiled, “Thanks for telling me.”

“You aren’t upset?”

“No. It was in the past. Like you said, you were a different person back then. I’m still going to punish you though,” Allen grinned. He untied the silk cloth from around her neck and stood, guiding his mother to the bed, her legs wrapped around him.

“But not for sleeping with Bob. I’m going to punish you for making us move back here, closer to grandma. Because now,” Allen said, grinding his cock deep into Krista, “it’s more difficult to keep our lifestyle a secret.”

“I know, I feel bad about that,” Krista moaned. “But you have another date tomorrow night. While you’re on it, I’ll be spending time with your grandmother.”

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