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Author’s note: I’m taking an extended beak from writing. I need to recharge, relax, refocus, and at some point later, revisit this hobby. I will finish this 8 part series after a break.
This story contains mom/daughter sex, sister/sister sex, sister/brother sex, and mom/son sex. Pretty much everyone has sex with everyone. If you’ve read the first three Challenge stories then you know how this will end. Be aware there is a very small portion of the story where one daughter is sedated by the mother, so she can easily have sex with her.
This story begins in April of the same year as the first three Challenge stories. The mom, Lisa, is based off Lisa Ann if you’re curious.
Editing thanks go to Todger65.
The Challenge 5: Lisa’s Family
Lisa put her long, dark brown hair in a ponytail, grabbed and lit a cigar, and slowly slid herself into a nice, hot bath. Smiling as the hot water enveloped her small, 5’2″ body, she sucked on the cigar, savoring the taste.
“My doctor would tell me not to smoke these,” Bob said, sitting at the opposite end of the tub with his own cigar.
“Well don’t,” one of Bob’s longest tenured employees joked. Lisa was based out of Los Angeles, but was in Atlanta for various meetings. Technology improvements allowed face time via the internet, but sometimes a good old-fashion in person meeting was far better for team building. The fact that Lisa and Bob have been occasionally sleeping together since her early 30’s was another reason she flew to the east coast from time-to-time.
Now, at 43, having secured and saved millions for Bob over the years, she was relaxing in his huge tub after an evening of fine dining and sex with the old man.
Bob ignored her suggestion, continuing to suck away on the cigar. He paused, watching Lisa do the same. “You like sucking on that don’t you?”
“I like sucking on other things too, Bob,” Lisa replied, blowing a smoke ring.
“I believe it. How old did you say your boyfriend is?”
“Well, he’s not my boyfriend anymore. We broke up when he left for college,” Lisa winked from across the tub.
“Mmm, you wild woman. You love sex don’t you,” Bob stated.
“I do. With all shapes and sizes.”
“Do you love sex more than your own children?” Bob asked, knowing the answer.
“Ha! Not quite that much, Bob.”
“Why don’t you combine the two? Sex with your children?” Bob suggested.
Lisa laughed, “Sure!”
“I’m serious. Put that cigar down and come here.”
Lisa did as she was told, moving across the tub to straddle Bob. She smiled, feeling his erection, and slowly guided it in her.
“There, much better,” Bob said. “Now let’s talk. I was serious. Sex with your kids.”
“Bob,” Lisa grunted, feeling him thrust upward. “That’s a little odd, don’t you think?”
Bob thrust once again, “I’ll pay you.”
“Uhnn,” Lisa moaned. “How much?”
Bob kept thrusting, water splashing over the side of the tub. “$10 million for each.”
“Ahh! Bob,” Lisa moaned.
“You have four children, so that’s $40 million, unless,” Bob kept thrusting, grabbing her large breasts.
“Uh-uh-unless what?” Lisa said with each impact.
Bob went still, releasing her breasts, “Unless you get one of them to help you. Then I’ll pay you double. Then an extra bonus, since you’ve been such a great employee.”
“You’re serious about this?” Lisa asked.
“Very. So that’s $40 million for sex with all four of your kids if you do this alone. If one of them joins in and helps you by seducing at least one of your other children, then I pay you double for everything. It’d be retroactively too. So if you seduce two that’s 10 million for each. Get one of them to seduce the other, and then I’ll pay you double for that kid, plus an extra 10 million for each one you slept with on your own.”
Lisa thought about it for all of three seconds. A smile formed on the sex loving, single mother’s mouth, “I’ll do it.”
“Good girl,” Bob said, thrusting upward into her again, spilling more water.
“I only have one question,” Lisa said. “Which of my kids should I recruit to help?”
“Done!” Alice made a final click of her mouse to book her tickets for a singles cruise in July – three months away.
“Well that does it. I hope it’s worth it,” Said the 26-year-old to no one in her apartment.
Alice’s love life was fairly dismal. She ended a long-term relationship four months prior in December. It was now April and the guy she had been sleeping with the last four months was about nine inches long, jet-black, and was usually mounted to her shower wall or bed’s headboard. She called the dildo “Rodney” in honor of the absolute pig of a man her sister, Angela, had tried to set her up with. Alice much preferred the sex toy Rodney instead of the human being Rodney; the sex toy was far more intelligent, kind, and attractive.
Alice looked at her long, nearly black hair in the mirror, full lips and dark green eyes. She grabbed her nice sized breasts, covered by etlik escort her t-shirt. “Maybe, I’ll meet a nice guy,” She thought about the singles cruise.
She removed her shirt, then her shorts and thong, turning around in the mirror, glancing at her long legs. At 5’11” she wondered if her height, gotten from her father’s side, was an issue. Maybe men didn’t like really tall women, she often wondered.
“Rodney! Come shower with me. I need that cock!” She called playfully out into the hallway. Changing her voice to imitate a male’s as best she could, “I’m already in here, baby.”
Alice pulled back the shower curtain, seeing the dildo already mounted, “Ah, so you are. Well then, let’s get to work.”
Just as Alice was about to turn the water on, she heard her cell phone ring. It was the tone she assigned to her mother, Lisa. She always answered her calls in the event of an emergency and just to be respectful.
“Hey mom, can I call you back? I was getting ready to shower,” Alice said, biting her bottom lip, looking at the massive mounted dildo in her shower.
“Sure, but I just wanted to tell you I’ll be flying down to Miami to visit you in a week or so,” Lisa said, lying naked against Bob.
“Is this part of that buyout deal? You’re not going to be my boss are you?” Alice asked.
“No! No, sweetie. I’m actually visiting just to visit,” Lisa said. Bob’s company had recently bought out the company Alice worked for. Lisa told Bob that her daughter worked for the smaller company, prompting Bob to suggest Alice when Lisa wondered out loud which of her children she could recruit to help with her challenge.
“Oh, uh sure, that’d be nice to see you. Are you staying with me?”
“Yes if that’s ok. I’d like to spent time with Angela as well,” Lisa said.
“Ok great. Well let me know when to pick you up from the airport.”
“I’ll have a rental car, but thank you.”
After they ended their call, Alice went to her knees in the shower, lovingly sucking on her favorite toy for several minutes. “Well, Rodney, my mother is coming to visit me soon,” Alice said, standing, turning around, and presenting her butt to the dildo. “Please don’t take offense if I don’t introduce you two.”
Back at Bob’s, Lisa smiled, thinking about this challenge. “You know Bob, I’ve heard rumors over the years that you were quite a pervert,” Lisa said, turning around, her hand going to his limp cock, bringing it back to life.
“It’s a good thing if you are,” Lisa said, sliding down his body, bringing his cock to her mouth. “Because I am too; get your checkbook ready, I’m going to seduce one of my kids before I leave for Miami.”
Bob and Lisa discussed more of the challenge the next morning. He gave her a camera device to record her actions, explaining the imagery would be downloaded with software on his computer.
Her youngest daughter, Jules, lived in the Atlanta area. Lisa already had lunch and dinner with her a few days earlier, right after she arrived. Jules relationship was often strained with her mother. Lisa knew it was because Jules and she were so similar. The two often argued about focusing on college and not partying so much – something Lisa had indulged upon way too much in her younger years. Jules was 21 and almost done with her junior year. She was barely passing.
Lisa recalled her memories from a few days earlier at her daughter’s apartment. She remembered seeing unusual, yet familiar, outfits strewn about, in poor attempts to be hidden at Jules’ apartment earlier in the week. There were bikini bottoms here and there, partly obscured by a pillow or couch, Jules obviously hurriedly hid them. It wasn’t summer yet, so Lisa found it odd. She also saw a sequined thong, tucked behind the couch from snooping when Jules was in the other room. There are black knee-high boots in the corner. She also saw a purple wig hidden in the bathroom closet. In the kitchen there was a schedule scribbled on some paper. The times 11 am to 3 am for the upcoming weekend were written on it.
Heading back to Jules’ apartment the day she left Bob’s mansion, she strategized, thinking about how to meet his challenge, pushing any thoughts that didn’t pertain to getting paid aside.
It was 1 pm when she knocked on Jules’ door. A taller, blonde woman, possibly late 30’s answered. “Hi!” She said.
“Hello, I’m Jules’ mother. Um,” Lisa confused, looked to the woman’s face. Her long hair was disheveled, she was wearing a shiny, blue sequined dress – it was as though she never changed out of it from the night before.
“I’m Torrie, Jules’ coworker, please come in! She’s just waking up and I have to leave. But it was nice meeting you,” Torrie replied, giving Lisa a hug. Her hair smelled like cigarettes and perfume.
“Bye,” Lisa smiled weakly, waving at the woman.
Lisa sat on the couch, listening to Jules brush her teeth in the bathroom. She saw a wad of money, several 20’s on the coffee table in front of her. There was a note under them.
“Thanks for covering etlik escort bayan for me the other night. Here’s your share. Wash your hands! They were in my thong!
PS: thanks for the hot night too!”
Lisa brought a hand to her mouth and stood. Pacing in front of the door, putting two and two together. “Mom?” Jules appeared, running her hands through her short black hair.
“Oh hi! Hello,” Lisa said.
“You ok?” Jules replied, quickly snatching the money, pretending she was cleaning off the table.
“Yes. I just wanted to take you to lunch. Looks like you’ve just woken up, so breakfast?” Lisa awkwardly attempted humor.
“Heh, yeah,” Jules moved to the kitchen, straightening up, putting dishes away. “I’ll change. Give me a few minutes.”
At lunch Lisa barely talked, thinking and planning instead. “She’s a stripper. She’s dancing somewhere. I gotta find out. I need to follow her, but what if she spots me? What if she gets mad? I need someone to help me. Alice can’t, she’s in Miami. Someone close.”
Jules talked about school a little. She didn’t want to drone on about how much she hated it, for fear her mother would come down on her, reminding Jules to be more responsible – unlike Lisa at that age.
“Wow that was a great lunch, mom. Thanks,” Jules hugged her at her apartment door.
“Mmhmm,” Lisa paused. “Um, sweetie, do you have plans tonight?”
“Oh, yeah, I have a bunch of studying to do,” Jules lied.
“Ah. I understand. I was thinking we could hang out again before I fly to Miami.”
“Yeah maybe. We’ll see.”
Lisa nodded, the door slowly closing on her. She had to find out where Jules danced.
“So you’re saying you’ll pay for everything, Bob?” Lisa asked on her cell phone. She was on the way to a coworker’s house to ask for assistance.
“Yes! I’ll pay for any travel fees, flights, any clothing you want to buy, and services you want to employ,” Bob said.
“So what if I want to give a friend $1000 to follow someone for me? To follow my daughter?”
“Sure, I will reimburse you. Anything you’ll need to accomplish your goals, to meet the challenge, I will purchase – including a nice vacation trip. Should you want to go somewhere,” Bob explained.
“Great! Gotta go, Bob, we’ll talk later!” Lisa ended the call, pulling into Devin’s driveway. She was a coworker and friend. She knew Devin would gladly help her.
Lisa was met with a flurry of kisses when the 5’10” 40-year-old blonde pulled her into her home. “Mmmph, I didn’t think you’d stop by on your visit,” Devin said in between kisses.
“There’s something I have to ask you,” Lisa said, removing her top, following Devin to her bedroom.
“Sure ask me anything,” Devin said, removing her own top, pushing Lisa back on to her bed. Ulysses, Devin’s former stepson, was already there and already naked, waiting for the two women.
“Mmmm,” Lisa said, kissing down his muscular body. She didn’t know Ulysses was Devin’s stepson, she thought he was her younger boyfriend.
Devin climbed into bed on the other side of Ulysses, kissing her way down his chest and abs, meeting Lisa at his cock. Devin took it in her mouth, looking at a hungry Lisa, coating the tip in saliva. She popped his cock out her mouth, handing it to Lisa. “So what did you want to ask me?”
Lisa took Ulysses in her mouth, moaning and slurping all over his dick. “I need you to follow someone for me. I need you to follow my daughter. She doesn’t know you. If she spots a gorgeous blonde woman following her, she may not think too much of it. I can’t have her catch me,” Lisa explained, sucking on Ulysses’ cockhead a few times before handing it back to Devin.
Lisa sucked and kissed on Ulysses testicles, while Devin thought. “I’ll pay you,” Lisa added then resumed sucking on a cum-filled testicle.
“I’ll do it!” Devin said, taking Ulysses’ cock out of her mouth with another loud pop. “I’ll need you to take care of Ulysses while I’m gone though,” Devin winked at Lisa.
Lisa glanced to Ulysses’ smiling face. “Hi, I’m Ulysses, nice to meet you,” He extended his hand to shake Lisa’s.
“Likewise,” She shook it and smiled back. Lisa grabbed his cock, sucking on the tip again, looking to Devin, “I’ll be glad to take care of him tonight.”
“Good, then give me all the information I need,” Devin replied. The two women licked each side of Ulysses’ long shaft, their tongues meeting at the tip, then parting with a string of saliva connecting them. They smiled at each other, Ulysses moaning in the background.
“I have some interesting news for you, my friend,” Devin told Lisa on the phone, sitting in her car in a parking lot. “Your little girl works for none other than Fat Rob.”
“What!?!” Lisa said.
“Yep. I followed her from her apartment to one of his clubs. I even went inside and watched her strip. I also spoke to Fat Rob afterward. And you know what he asked me?” Devin said.
“What?” Lisa was straddling Ulysses, escort etlik pausing her cock riding to answer Devin’s call.
“He asked me if I want to buy her for the night.”
“You mean, she’s also hooking?” Lisa said, slowly getting off Ulysses, his cock sliding out of her. She went to the bedroom window, staring out into the moonlit back yard.
“Apparently. I said no thanks.”
“Wow, I can’t believe it. This is horrible,” Lisa was genuinely upset. Yes, she herself was a wild, sexual woman; the thought of stripping wasn’t too bad. She had visited many strip clubs in her years. However, prostitution was dangerous and irresponsible. Lisa felt genuine concern and fear for her daughter’s safety.
Lisa gathered her composure and thanked Devin. She ended the call and climbed back in bed with Ulysses. Snuggling against his hard body, she thought about Fat Rob. He was a coworker, responsible for “talent relations and acquisitions.” Most people that had worked with him for years knew that he slept with most of the female models he hired. Lisa was even aware that he managed a couple clubs in LA and Florida. She had no idea he dabbled in prostitution.
Lying against Ulysses body, she sighed heavily, thinking about her next step. “You ok?” Ulysses asked.
“Yeah, I’m just thinking about things,” Lisa replied. “You sure are a sweet guy. I’m glad Devin is willing to share her boyfriend for the night.”
“Uh, yeah,” Ulysses coughed, not wanting to reveal that Devin was his former stepmother to someone he just met. “We have a special kind of love.”
The next morning, the three of them had sex in the shower. Ulysses was in the middle; Lisa was in front of him, kissing his body, servicing his cock. The much taller Devin was behind him, kissing his back, neck, shoulders, and face.
Lisa wrote Devin a check for $1000. She wrote a little receipt of sorts on a piece of paper, Devin initialed it, Bob would reimburse her.
She had come up with a plan. Lisa called Bob to get Fat Rob’s address. She was on her way to have a talk with her daughter’s employer.
At Fat Rob’s large apartment, she knocked on the door. To Lisa’s surprise, Torrie answered, wearing a thong bikini, “Oh Hi! I remember you, come in!”
Lisa smiled politely, assuming Torrie worked for Fat Rob too. “So, Torrie, right? What are you doing here?”
“Oh, I live here,” She answered.
“You work for Fat Rob?”
“Yep,” Torrie led Lisa inside. “He’s my boss!” she cheerily said, leading Lisa to the hot tub Fat Rob was sitting in out on the balcony of his luxurious apartment.
“Miss Lisa! What are you doing here?” Fat Rob, smiled, putting his cigar down.
“I’m here to ask you about some business.” Lisa glanced to the two younger women on each side of him, “In private.”
Torrie backed into the apartment, followed by the two other women, after Fat Rob motioned for them to leave.
“Well, then please have a seat, or join me,” Fat Rob grinned.
“Suit yourself. What can I do for you?”
“You are employing someone I want to spent time with,” Lisa replied, relaying the conversation she practiced over and over in her head on the way to Fat Rob’s. “I want to,” Lisa paused, clearing her throat, “buy them for the night,” she struggled to say.
“I see. So you like ladies as well as men?”
“Yes. Are you willing to help me and sell me some time with this special person?” Lisa asked, ignoring the sadness she felt for Jules.
“Of course, Miss Lisa. We’ve worked together for a several years. I’ll throw in a discount. I’ll throw in an even bigger discount if you get in this hot tub with me and ride my dick awhile,” Fat Rob winked, puffing on his cigar.
Lisa sighed. “Sorry, not today. How much for time with a girl named Jules?” Lisa asked, hoping her brown eyes and short stature was enough to hide any resemblance from the taller, green-eyed, Jules.
“Ooh, Miss Jules. She’s pretty pricy. She’s VERY high in demand. If you want all night, that’s five grand, normally eight.”
“Wow. What about an hour or so?”
“Well,” Fat Rob paused, thinking of an arbitrary figure to give his co-worker. “How about $800 an hour. Normally I charge $1200 per hour. But you and I go way back.”
“Does Bob know about your little side job?” Lisa asked.
“Of course! He’s the one that built and developed the land the strip club is on. He’s the one I pay rent to. He even came to me with the idea of charging clients extra for sex,” Fat Rob explained.
“Figures,” Lisa said. “Anyway, yes, $800 for an hour with Jules. There’s one other thing.”
“I want her blindfolded.”
“Ooh, kinky,” Fat Rob grinned, finishing his cigar.
“Is this doable?”
“Sure. I’ll have her waiting for you in a hotel room of your choice. She’ll be blindfolded and ready.”
They ironed out the details, the times, and the place, shook hands and closed the deal. Fat Rob stood in the hot tub as Lisa was leaving. “Miss Lisa.”
She turned around, seeing his naked body. “Are you sure you don’t want any of this?” Fat Rob asked.
Looking at his dangling cock, “Thanks for reminding me why they call you Fat Rob, but again, no thanks. Maybe when you’re in LA again.” Lisa smiled and took her leave, Torrie hugging her on her way out.
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