The Challenge 5: Lisa’s Family by tw_holt

Editing thanks go to Todger65.

The Challenge 5: Lisa’s Family

Chapter 1

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?”

Chapter 2

“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 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.”

Chapter 3

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 for me the other night. Here’s your share. Wash your hands! They were in my thong!

xoxo
-Torrie

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.

Chapter 4

“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, 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.

“Not today.”

“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.”

“What’s that?”

“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.

After Lisa left, Torrie stripped out of her bikini, re-entered the hot tub, guided Fat Rob’s fat cock back inside her and smiled at him. “So what was Jules’ mom doing here?”

“Jules’ mom?” Fat Rob asked, a sneaky grin appearing on his face.

Chapter 5

Lisa borrowed Devin’s perfume that night. She used Devin’s shampoo instead of her own. She also used some of Devin’s makeup products, deodorant, and moisturizer. She didn’t use anything she owned. She didn’t want any trace of her scent to fill Jules’ nostrils. She had her hair in a ponytail, hoping to avoid her hair coming into contact with Jules’ skin or hands, fearful Jules may recognize the thickness.

Lisa nearly started crying when she saw her daughter, blindfolded, smiling, and waiting in the hotel room. Lisa took a deep breath, careful not to exhale audibly enough to where Jules would recognize it. Lisa was going to be silent.

“Hi, are you there?” Jules asked.

“Shhh,” Lisa attempted to disguise her voice making the shush as high pitched as possible.

“Ah, no talking, I understand. I’ll be quiet and enjoy this,” Jules replied.
Lisa set the camera on the entertainment center the TV resided in. Turning it on, like Bob instructed her, she waved at the little red light. Bob said he may not be at his computer to watch in real time, but the software would save the footage and notify him of it when he opened the program.

Jules felt someone standing next to her; she smiled, waiting for this mystery woman to begin. “I love women just as much as men. I’ve never been blindfolded by one, but this’ll be great. Do you want me to – ”

Lisa brought her index finger to Jules mouth to quiet her daughter.

Lisa froze once again, looking at her daughter’s lips, her short black hair, her cleavage. She was wearing a white bathrobe, presumably nude underneath. Lisa shook her head, closing her eyes, “Think of the money. $10 million for this. An extra ten on top of that if Alice joins me.”

Lisa slowly started to remove the robe from Jules’ shoulder. Lisa looked on in shock at the elaborate shoulder tattoo she had. It was a floral pattern and it trailed down to her elbow. Lisa figured she got the money for it from stripping. She cringed thinking that prostitution was a source of income for her daughter as well. Here Lisa was, contributing to it.

Moving the robe further down, exposing Jules’ perky breasts, Lisa stared at them. They were nice, not too big or small. “Keep going,” she told herself.

She helped Jules slide her other arm out of the robe next. Sliding it down her back, Lisa sat behind her daughter, discovering more tattoos. Lisa shook her head looking downward. Closing her eyes, she kissed Jules’ back, between her shoulder blades. Next she kissed her shoulder, then the back of her neck. Jules moaned, the kisses sending tingles down her spine.

Lisa reached around, lightly cupping Jules’ medium-sized, perky breasts. “Do it,” Lisa told herself.

She tweaked the nipples, rolling them between her index finger and thumb. Jules had a sharp intake of air followed by a soft moan. Lisa kept teasing, kissing the back of her neck in the process. “Yes,” Jules whispered.

Lisa closed her eyes, “Just let go,” she told herself. “Think of the money.”

Lisa released one breast, the fingers of the other hand still rolling and teasing a nipple. Her free hand slid down Jules’ tight body, over her belly button ring, pausing when a finger grazed Jules’ trimmed bush.

Lisa pictured a check, written to her by Bob. She pictured giving Jules enough money to stop working for Fat Rob, to get her out of that lifestyle. Pushing any further guilt out of her thoughts, Lisa slid her hand down further, arriving at and rubbing Jules’ clit.

Jules moaned and shook, laying her head back on her mother’s shoulder, her mouth hanging open. Lisa turned, looking to it, listening to the moans. She opened her own mouth, inching toward Jules’. When the bottoms of their lips touched, causing Jules to moan once more, Lisa’s mouth covered her daughters. Lisa was careful not to make a sound; not wanting her voice to give her away.

Their mouths were connected for several minutes, while Lisa worked Jules’ clit and nipple, before sliding her fingers into Jules’ soaking wet pussy.

Lisa broke the kiss, her other hand going to Jules’ clit, rubbing it while she fingered her with her other hand. A moment later, Lisa felt her daughter shake harder, tensing up, climaxing in her arms. When the moaning stopped, the orgasm subsiding, Lisa was overcome with taboo lust.

She quickly stood and stripped naked, taking Jules hand, bringing it to her breasts. Lisa watched Jules smile while she felt the large tit in her hand.

Lisa’s hand went to the back of her blindfolded daughter’s head, pulling her forward. Lisa’s other hand held her own breasts, offering it to Jules’ incoming open mouth. Jules flicked her tongue at the nipple several times, before devouring it, sucking hungrily at it.

Lisa couldn’t take anymore. She pushed her daughter on her back and climbed on top of her, turning around, lowering her own soaking pussy to Jules’ face.

She tasted so good. So wrong, but so good. Lisa nearly climaxed within ten seconds of experiencing Jules’ oral skills. She wondered how many pussies her daughter had licked. Lisa wondered if it was more than she had. She wondered about how many cocks Jules had serviced. Lisa thought about Fat Rob grimacing with pleasure before blowing his load into Jules, like he had done to Lisa during his LA business trips.

Lisa’s tongue swirled around the most forbidden of places – lapping up the juices, drinking the nectar of her youngest daughter. “Such wickedness, such unnatural pleasure, all for money,” was Lisa’s last thought before her orgasm erupted in her. Jules’ tongue slithered out of her mother’s pussy and she bellowed out into the hotel room. Lisa covered her own mouth, hoping to quiet her own cries of pleasure.

Feeling her daughter’s body shake under her own, Lisa collapsed on top it, shaking with her. “Was this enough to satisfy Bob?” She asked herself. She shook her head – it wasn’t.

She pushed Jules further back on the bed, spread her legs, and guided her own to entwine with Jules’. “I want that pussy against mine,” Lisa thought. Right as her clit met Jules, right as her drenched pussy lips kissed her daughter’s, she nearly came again.

Grinding and sliding their pussies against each other, Lisa thought how much better Jules’ felt than Devin’s, or any of the other women she’d been with. As they bounced up and down, facing one another, Lisa watched Jules lick her lips clean, her long tongue lapping at the saliva and vaginal fluids. It was so erotic; Lisa had to pull Jules in for another kiss while continuing to grind their pussies together.

Lisa felt Jules tense up once again, another orgasm approaching. Lisa couldn’t help but have one of her own. They climaxed together, Lisa biting her bottom lip to keep from screaming. “I love you! I love you darling!” Lisa screamed in her head instead.

It was done. Lisa, still out of breath, quickly unwrapped her legs from around her daughter’s. She put on a t-shirt she had in a bag followed by some shorts. She closed the door a little harder so Jules would know she was alone in the room.

Jules was left moaning, writhing around on the bed, her hand gathering up as much of her and her mother’s juices as she could. When the orgasm subsided, she removed the blindfold and let out a euphoric induced laugh.

She called Fat Rob a moment later, “I don’t know who that was, but that was the best sex I have ever had.”

“Mmm, good girl. Why don’t you come down to my office at the club and give me more details in person,” Fat Rob replied.

“I’ll be right there,” Jules grinned, ending the call, gathering her things, her body still numb.

Chapter 6

After leaving her daughter in orgasmic bliss, Lisa headed back to Bob’s crying tears of guilt on the way.
Bob comforted her, watching the footage, writing her a check of $10 million. He suggested Lisa could help Jules with her troubles, perhaps lead her out of stripping and prostitution, and provide her a new life with this money. He reminded her that she was going to Miami soon and to think of a way to include Alice in this challenge. Lisa also had to figure out how to seduce Alice’s twin, Angela.

They were non-identical or fraternal twins. Angela was 5’9” had similar long dark hair; however, her breasts were slightly larger than Alice’s. She also seemed to get most of her curves in her hips, butt, and thighs. Having posed in Elite Magazine, a magazine marketed toward African-American males ages 18-35, she knew of her assets and used them to her advantage and fun.

Angela was sleeping with the human version of Rodney. She had been for a couple years now. She was part of his entourage. Angela repeatedly tried to get Alice to join, to go clubbing with them or to parties, and then back to Rodney’s for sex, however, Alice always refused. One time, Alice lashed out at Angela, calling her trash, an idiot, and other fairly hurtful names. It hurt Angela’s feelings, but deep down, she agreed. Lifestyle habits were hard to break.

Angela woke up early Saturday morning to the sound of her coworkers, Elite Mag models Taylor and Claudia, sucking on Rodney’s cock. The blonde and Puerto Rican sucked and slurped along his dick, as Angela yawned, stretched, and made her way to the bathroom – Rodney’s dried semen trailing down her thigh.

Her mother, Lisa, had called her earlier in the week letting her know she was visiting for a few days. Angela called Alice, receiving a typical cold reception of “uh huhs,” “yeahs,” and “oks” with no other conversation. She wished things were different between her and her sister, but she blamed herself.

Angela was looking forward to seeing her mother. She hadn’t seen Lisa since Thanksgiving. They weren’t extremely close, but got along well enough.

“Hi there,” Taylor told Angela when she reentered Rodney’s bedroom. She was sitting on his face, while Claudia was sitting on his cock.

“I have to leave. Take my place?” Claudia asked.

Angela didn’t feel like it. She wanted to leave too. But, like in so many situations before, she wanted to appease her friends, kicking herself later, she decided take Claudia’s place upon Rodney’s cock. She smiled into Taylor’s face while she rode it. Claudia got dressed, kissing them both goodbye, and left.

Angela’s orgasm was mild if anything. Like most have been lately. Ever since Alice told Angela off, her hurtful words stirred something in her.

She got dressed, smiled goodbye, and went home. Angela cleaned her apartment for her mother’s arrival. Lisa, however, was stopping by Alice’s first.

*****

“I think I’m going to be sick. Are you joking?” Alice, feeling rage and disgust building, asked her mother. Lisa had arrived earlier, sitting her daughter down to have a serious discussion. The discussion was everything Bob had challenged her to do and all the monetary amounts as the reward.

“I’m not joking, Alice,” Lisa placed her hand on Alice’s. Alice quickly withdrew it. “Alice, please. This is a lot of money involved. With your help, it’d be even more.”

Alice remained quiet, trying to make sense of this. “I just, I mean, this is wrong.”

“Yes. But that is a lot of money.”

“I’m not into girls. There is no way I’m seducing her,” Alice said, referring to Angela.

“You don’t have to. You can take someone else.”

“Jules? I’m hardly close with her, less than I am Angela. I have nothing in common with either of them,” Alice said.

“Well, then,” Lisa said in a soft voice. “What about your brother?”

Alice’s face turned even whiter than it did upon hearing of the challenge.

“Lenny is a sweet kid. From what I know, I don’t think he has much experience. You never know, he might even have a crush on you.”

“Ew,” Alice said, shuddering at the thought.

“Please? There are ways we can get around this. There are things we can do to make them not know it’s us. Trust me, I know.”

“What do you mean?” Alice asked.

Lisa sighed, reaching into her purse, finding the check Bob wrote her, holding it up in front of Alice’s shocked face.

“I already, um, took out, so-to-speak, Jules,” Lisa said.

Alice slowly looked away, her mouth agape. “I can’t believe this.”

“Ten million dollars. I’m going to deposit it when I return to LA. I’m hoping to have more checks to deposit.”

“Why? Why is he doing this? This is wrong. He’s the owner of this huge corporation, someone should tell – ” Alice said, before Lisa cut her off.

“He can. He does it because he can. And no, we aren’t telling the authorities or anyone about this. You will either join me and we’ll bring in even more money, or you won’t. I will go it alone and bring in 10 million for each.”

Alice closed her eyes, trying to shake the thoughts of what she’s been told out of her mind.

“Alice, please, think of the money and all we could do with it. We could retire early. We could buy new vehicles. It’d be amazing,” Lisa said, gently patting her daughter’s shoulder.

“You said they wouldn’t have to know it’s us? What did you mean?” Alice asked, seriously considering the possibility of being a millionaire from doing one, taboo, disgusting act.

“She was blindfolded. She didn’t know it was me doing that stuff to her. Jules is in a bad state. She’s working at a strip club, she’s doing prostitution,” Lisa said, eyes watering, choking up. “I’ve failed her. I even contributed to it. But maybe, we can get her away from all that with this money.”

“Mom,” Alice looked on pleadingly. “Please don’t ask me to do this.”

“Just think of her, think of others even. You could help people. You’re such a beautiful person, please, suspend your conscience just a little bit and help me.”

“How would you,” Alice sighed, “seduce Angela?”

“I have no idea.”

Chapter 7

“Rodney,” Alice spoke up after an hour of quiet thinking about the situation while her mother unpacked.

“Who?”

“He’s this guy that Angela hangs around. She’s tried to get me to go out with her and her group of friends, including him, but I can’t stand him. I’m wondering if we go out with him and her tonight, we could look for opportunities. Maybe he could get Angela really drunk and you offer to take her home or something,” Alice said.

“Yes, maybe you could distract Rodney and – ”

“No. I’m not sleeping with him if that’s what you’re suggesting. He’s the type of garbage that would take a woman to the bathroom of the club and, well, you know.”

“Have sex with her there?”

“Right,” Alice answered. “If I go out with you two tonight, maybe we could observe, watch, maybe even see an opportunity for you to, uh, take her to bed.” Alice struggled to say.

“So are you willing to help me then?” Lisa asked.

“I still don’t know. I’m still thinking about Lenny.”

“Well IF you don’t help me, I guess I can try to get 30 million. Unless you and I were to – ”

“No! No way. Sorry mom,” Alice cut her off.

“Alright, that’s fine,” Lisa smiled, slightly hurt, but also relieved that she wouldn’t have to worry about trying to seduce another child.

Lisa frowned a little later when she heard the phone call between Alice and Angela. Alice was short with her, didn’t seem cheerful at all, and wanted to get off the phone as quickly as possible. She arranged to meet Angela, much to Angela’s delight, that evening at 9 pm. Lisa would be joining them.

*****

Rodney was a pig, as usual, that evening at least in Alice’s eyes. He flirted shamelessly with the three brunettes. So much so that Alice pulled her mother aside, asking her what she was doing. Lisa assured her she’s getting close to him to see and learn what she can.

Alice and Angela sat at the booth, sipping their drinks, watching Rodney run his hands all over their mother on the dance floor. Angela tried to initiate conversation, but failed, often being met with quick replies from Alice.

Lisa felt Rodney’s erection against her back as they danced. Thinking that Angela was a lucky girl, she remembered her plan. She turned around, pulling Rodney’s face to her own, whispering in his ear.

*****

The men’s room of the club they went to was disgusting. Some lights worked, some didn’t, and some flickered. One of the sinks had a leaky faucet. All the urinals were either cracked, dripping, or needed a thorough cleaning. The floor was horrible. It had cigarette butts, ashes, and a few spots where men spit. Small urine puddles were around each urinal and toilet caused by drunken patrons that “missed.” A couple of the toilets were clogged. Several of the bathroom stall doors didn’t close all the way. Each stall had graffiti or obscene messages written in permanent markers covering its walls.

The very last of several stalls had an un-flushed, nasty, toilet. It dripped water behind it, which gathered on the floor, creating a small puddle. The top of the toilet had ashes from cigarettes, and a blunt of marijuana resting on it. It hadn’t been cleaned in, what looked like, weeks. The seat was up; there were pee stains and pubic hair. Typical of a poorly run, rarely cleaned, bar or club.

“FUCK ME!” Lisa commanded as Rodney threw the stall door open and roughly sat her down on top of the toilet.
“Oh yeah? You want this dick?” he asked as he was pulling his tucked shirt out of his pants.

“Mmmhmm,” Lisa moaned as she grabbed his face and stuck her tongue into his mouth.

Her head bobbed back and forth and she sucked his tongue. “Mmm your tongue is bigger than my ex-husbands cock.”

“Uh huh,” Rodney said as he unzipped his pants and pulled out his massive member, “Now give me that pussy, girl. We ain’t got much time.”

“Be patient, this momma wants to play,” Lisa sliding to the toilet seat, grabbing Rodney’s cock and sucked away at it. “Angela enjoys this too?”

“Yeah.” Lisa continued sucking his cock, “Alice doesn’t?”

“She doesn’t like me,” Rodney answered.

“Aww too bad,” Lisa replied, licking the shaft, coating his cock in saliva. Her overwhelming horniness overtaking her, she nearly forgot why she was there.

“Maybe if you get Alice drunk enough, you could have all three of us tonight. Would you like that?”

“I’d love it!”

Lisa kept sucking, thinking, “I’ll get Angela drunk, and take her to another room alone.” Lisa ran her hands over Rodney’s thighs. She felt something in his pocket, a small cylindrical shaped object. Rodney, looking to the ceiling, moaning, didn’t feel Lisa remove it from his pocket.

“What’s this?” Lisa asked.

“Huh? Oh, that,” Rodney looked flustered.

Lisa opened it, “is this what I think it is?”

“Here, I’ll take that,” Rodney reached for the plastic container. Lisa moved her hand, the tiny white pills jiggling inside it.

“Rodney, are these some sort of sedative pills?”

“Yeah, I just have them – ”

“To put in someone’s drink?”

“Well, I uh – ”

“Put one in Alice’s drink,” Lisa said flatly.

“What?”

“You heard me. She doesn’t like you at all. If you want to sedate her so you can have sex with her, go right ahead,” Lisa looked at his cock. “If she remembers it, she’ll thank you in the morning,” Lisa couldn’t believe the words coming out of her mouth. She couldn’t believe what she was sinking to for money.

“That’s a little messed up,” Rodney admitted.

Lisa shrugged, “I don’t mind.”

“I’ll give her half one, she’ll be out of it, but not knocked out,” Rodney said.

“Do it,” Lisa nodded.

They left the bathroom together. Lisa told Rodney she’ll distract her daughters for him, while he put half a pill in Alice’s drink.

Lisa waved her daughters over, saying she wanted to dance with both of them. Angela smiled and agreed, pulling Alice along. Lisa looked over to Rodney through the crowded dance floor. He nodded at her when their eyes met. The song ended and the three headed back to their seat.

Lisa pulled Alice in for a whisper, “Switch your drink with Angela. Trust me.” Alice’s eyes widened and she nodded.

“Rodney, one more dance? Then we should probably get going. It’s late,” Lisa said. Rodney smiled and followed her, once again basically dry humping her on the dance floor.

“Can I try your drink?” Alice asked Angela.

“Sure,” She smiled. Alice sipped the martini.

“That’s good. Trade you?” Alice asked.

“Oh sure. Yeah that martini is too strong for me,” Angela said, taking Alice’s cranberry and vodka drink. Lisa watched Angela take several sips.

“I’m a horrible person. Please forgive me Angela. We’ll be millionaires together,” She thought to herself.

Chapter 8

Angela got drowsier and drowsier with each passing minute. Alice was slightly confused. But was able to deduce her drink was drugged.

“Alice why don’t you and Rodney dance?” Lisa suggested. “Then we’ll all leave.”

Alice shot her mom a look and agreed, not looking forward to touching or being touched by Rodney. “When the song is over, come outside to my car, we’ll leave,” She whispered in Alice’s ear.

As soon as they left the table, Lisa pulled Angela up, her arm around her waist and walked with her outside. Angela became heavier with each step, by the time she got to the car, she could barely stand. Lisa guided her as best she could into the back seat of the rental car, working to pull the taller, heavier woman into it. When she was done, she got in the driver’s side and started up the car.

“You going to let me get that ass tonight?” Rodney asked Alice, his hands sliding down to that which he desired.

“Maybe,” Alice said, glancing over to the empty booth where they all had been sitting. She wondered if Rodney was as big as the dildo she owned. She thought about how much she preferred that inanimate object to the actual Rodney.

“Let me go to the bathroom first,” Alice said. “I’ll meet you in the men’s room.”

“I’ll be waiting, baby,” Rodney grinned. They both headed to the bathroom, Alice going inside hers, waiting a couple seconds then rushing out of it. She hurriedly walked across the club, making her way to the exit.

When she was outside she found her mother’s rental car in the parking lot. Climbing into the passenger side, her mother sped off. Rodney was still in the bathroom waiting for Alice. Fifteen minutes later, he emerged, Alice, Angela, and Lisa were nowhere in sight. Rodney went home alone.

*****

“I’m going for a walk, while you and her,” Alice shuddered. “You know.”

“Earn $10 million dollars? Ok sweetie, come back a little later,” Lisa said, closing her bedroom at Alice’s apartment.

Angela was barely awake, she was moving some, but certainly sedated. She was moaning lightly, while Lisa set the camera up to record.

“Here, let’s get these off,” Lisa whispered, helping her daughter remove her dress. Next was her bra and thong. Lisa slid it off, letting it land at her feet. Lisa stood back, unzipping her own dress, sliding it down and stepping out of it. She watched her daughter’s nude body before her, Angela’s hands lightly moving across her skin.

Lisa removed her own bra and thong, and then climbed on top of Angela, kissing her mouth, cheek and neck. Lisa kissed Angela’s erect nipples, pausing when she heard her daughter moan. She wondered just how aware Angela was. After lightly sucking a nipple, Lisa sat up, admiring Angela’s hourglass curves.

“You’re beautiful baby,” Lisa whispered, bending down to kiss at Angela’s breasts, her own tits dragging across Angela’s tummy.

Lisa kissed her way down to Angela’s pussy. She was trimmed in a similar fashion to Jules – a very light bush. Lisa sucked at Angela’s clit, guilt slowly melting away, listening to Angela whimper.

“Mmmm,” Angela moaned loudly, one hand going to her own breast. Lisa paused her oral service to watch her daughter seemingly enjoy this. Lisa brought her own hand to massage Angela’s other large breast.

Angela moaned again, louder this time. “You are enjoying this,” Lisa whispered. She stopped licking at Angela’s slit and climbed on top of her.

“Mommy will be gentle,” She whispered, straddling Angela in such a way that her thigh landed on top of Angela’s pussy. Angela’s thigh was against Lisa’s own dripping sex.

Lisa began humping her, grinding against her, thigh against pussy. For a second Lisa thought Angela’s eyes opened, but if so they closed immediately. Her mouth hung open as she moaned, Lisa bending down to kiss Angela’s bottom lip, nibbling lightly.

Lisa kept working, thinking about the money and thinking about how gorgeous her daughter looked below her. Suddenly, Lisa felt it. She felt Angela grind back against her mother.

“Yes, please, please do it back,” Lisa thought. It felt so good.

As their mutual pleasure increased, Lisa wondered if Angela would remember this or if it was all a dream. It didn’t matter, she guessed.

Lisa thought Angela could quit modeling. With the money Lisa was bringing in, Angela could go to college or move away somewhere, away from Rodney and her other friends.

Angela let out a louder moan, her body starting to shake. She suddenly gripped her mother’s forearm next to her head. Lisa, fearful of causing her to come out of her sedation, if that was possible, again attempted to be as quiet, grinding her way against Angela to her own orgasm.

Lisa collapsed on top of her, catching her breath. “Thank you, my sweet darling, thank you,” Lisa thought, kissing and licking at Angela’s open mouth. “I love you.”

Lisa climbed off Angela, grabbed the camera and her clothes, and left her daughter whimpering, alone in the bed.

“Mom,” Angela whispered. “Come back, please,” was the last thing she said before going to sleep minutes later.

Chapter 9

Lisa was sitting on the couch, hands to her face, crying, when Alice returned from her walk.

“Hey mom. So did you do it? Did you have sex with my sister?” Alice asked with a condescending tone.

Lisa nodded, wiped her tears, and gathered herself. “It’s done.”

“Well I hope you feel good about yourself,” Alice said, sitting next to her on the couch. “Is she even awake?”

“She was groggy but not fully asleep during it. I peeped in on her a few minutes ago and she’s asleep now.”

“So I guess that’s another ten million for you,” Alice said.

“For us,” Lisa corrected her. “This money is all of ours.”

Alice shook her head.

“Yes. Please,” Lisa turned to her, “please forgive me. But please consider helping me. If you and your brother have sex, we’ll get paid double for what I’ve already done, plus double for what you do.”

“I’m going to bed,” Alice said, getting up to leave.

A few minutes later, Alice had changed into her t-shirt and pajama shorts. Reaching under her pillow she pulled out Rodney, her dildo mockingly named after the person. “Maybe you can have me tonight. Make me forget about this,” She whispered, kissing the tip of the dildo. She turned around, mounting it to the wooden headboard of her bed, and like so many nights before, she pulled her shorts down, and backed into it, gripping the sheets as the tip entered her. “Mmm, like that,” she moaned inwardly, biting her bottom lip.

“Sweetie, can we talk some?” Lisa barged into Alice’s room, startling her, quickly looking away. “I’m sorry!”

“Mom!” Alice pulled up her shorts, grabbing the dildo, throwing it to the other side of the bed, away from the door.

“Sorry!” Lisa closed the door, standing on the other side.

“What do you want?”

“I just want to talk some,” Lisa replied.

“Knock next time. Come in,” Alice groaned.

Lisa slowly entered, wearing her pink nightie, sitting next to Alice on the bed. “I just want to chat about everything. I really want you to consider helping me with this.”

“Mom, it’s all I’ve thought about since you’ve told me. I still don’t know.”

“I understand. I’ve been thinking too. But about something different. I’ve been thinking that all of us, you, your siblings, me and maybe even some of your aunts, could all live in one house together. It’d be amazing,” Lisa said.

“Mom,” Alice shook her head.

Lisa tipped Alice’s chin, their eyes meeting, “With all that money, one happy family.”

Alice shrugged.

“We wouldn’t have to have sex with each other,” Lisa said, thinking about how wonderful it felt to feel Angela orgasm in her arms earlier. “Unless you wanted to,” she added, caressing Alice’s cheek.

“It’s just,” Alice paused, taking her mother’s hand, slowly moving it away from her face, “I don’t get why Bob is doing this. Why he’s issuing this challenge.”

“Would you like to talk to him? You could ask him anything,” Lisa suggested.

“I might want to, yes.”

“Better yet, how about you come back to Atlanta with me in a couple days? We can meet with Bob and talk it out, you can get to know him better.”

“I have to work.”

“I’m sure Bob will arrange everything. He’ll pay for plane fare as well,” Lisa said.

Alice nodded, “Alright.”

Lisa hugged her daughter, kissing her cheek slowly. “Can I sleep in here with you?”

“You don’t want to sleep in there with Angela?”

“She’s naked. She may wake up like that with me in there and feel weird.”

“Are you going to confess to her and Jules what you did?”

“I will. Eventually,” Lisa said, lying down next to Alice. “I will after I, or we, get through this. I’d want them to know the truth when it’s all over and ask for their forgiveness.”

“Maybe they’ll understand. Who knows?” Alice said.

There was a pause, Lisa propped herself up on her elbows, “Can I see it?”

“See what?”

“Your toy.”

“Ugh, mom,” Alice rolled her eyes.

“There’s nothing to be embarrassed about. I have several toys myself.”

“Fine. It’s over there,” Alice pointed to the floor on the other side of the bed. Lisa rolled over, reached and took it.

“Nice. It’s pretty large. Not as big as mine, but still very impressive.”

“Geez, mom.”

Lisa suddenly engulfed the tip, moaning, tasting Alice’s fluids. Alice’s eyes shot open and she looked away embarrassed, hoping her mother didn’t realize the dildo was inside her body when she barged into her room. She hoped, what Lisa did see, wasn’t much.

“Ok, well goodnight,” Alice said, quickly rolling over to her side, facing away from her mother. She heard the heavy dildo drop on the carpet, and then felt her short mother’s warm body snuggle up to her back. Alice smiled softly, enjoying the warmth, and went to sleep.

Chapter 10

A few days later Alice and Lisa were on their way to Bob’s in Atlanta on an early morning flight. They spoke about Angela. The next day after her and Lisa’s sexual encounter with her she seemed groggy, as predicted, but also distracted, like she was in a hurry to leave. The only time Lisa saw Angela again in Miami was for lunch the day before she and Alice left. Angela, again, seemed like something was on her mind, but was otherwise polite and friendly as usual.

When they arrived at Bob’s he, too, seemed distracted. He had just returned from his doctor and the visit wasn’t very pleasant. He shook the cob webs from his thoughts and invited them to his office.

“Bob, Alice was hoping to talk with you about this challenge,” Lisa told him.

“That’s a great idea! Alice, I was thinking you could go shopping, buy a nice dress, buy some earrings if you like; maybe get your hair done as well. Not that you need to. You are stunning, but it’s an option. Then tonight, I will take you to a lovely dinner, afterward, we’ll come back here and a have a nice chit chat about everything.”

“Oh uh, well,” Alice stammered.

“You can use my credit card. I’ll pay for everything. You’ll discover I’m great at arranging things. I’ve arranged with your direct supervisors for you to be here for a few extra days. I told them there was a special project that I want you to work on.”

Alice glanced to her mother. “Lisa, as for you,” Bob said. “I’ve arranged for you to spend the day at a spa followed by an evening at the theater.”

“Oh, thanks, but I don’t have a – ”

“Date? I’ve arranged that as well,” Bob winked. “Your new gown will be delivered to the spa. The lucky gentleman will pick you up from there and you’ll have a wonderful night.”

Before either of them could reply, Bob handed Alice a credit card and keys to one of his Corvettes and ushered them off. His driver picked Lisa up and Alice sped off in the other direction toward the upscale shopping area Bob directed her to – with assistance from the GPS device in the car.

Bob watched them leave. He then clutched his chest, attempting to breathe slowly; hoping whatever was happening would pass like it did last time.

*****

A few hours later, Alice turned around, looking at herself in the full body mirror in Bob’s master bedroom. He welcomed her back and directed her to his room to get ready for the evening. She saw his huge king size bed, fireplace, bathroom with huge shower and tub.

The dress was dark blue, short, and sexy, but not inappropriate for dinner. She purchased pearl earrings to go with the ensemble. Her hair was curled into long, wavy locks flowing down her back.

At that same moment, Lisa stood outside of the luxury spa waiting to be picked up by her date. She was wearing long black dress, Bob had gotten her. An Escalade pulled up, lowering the windows. Lisa chuckled and got in.

“So you’re my date tonight?” She asked.

“Yes Miss Lisa. Bob requested I show you a good time,” Fat Rob replied.

Lisa figured out Bob’s plan. He wanted her gone all night. “Well,” Lisa said, bending over to the driver’s side, unbuttoning and unzipping Fat Rob’s pants, fishing out his cock. “We can go to the theater, or straight back to your place.”

Fat Rob moaned as Lisa worked on the tip of his cock, “I think you know my answer. When do you need to be back at Bob’s?”

Lisa removed his cock from her mouth with a loud pop. “This mommy doesn’t have a curfew. So, tomorrow morning,” the millionaire winked at Fat Rob before engulfing his cock again.

“You are a naughty mommy,” Fat Rob said, driving away while his cock was being sucked.

“Very,” Lisa replied. Fat Rob considered for a second, knowing how naughty Lisa was, inviting Jules to join them, but decided against it. He wanted to savor Lisa all for himself that night.

*****

Alice nearly forgot all about why she was spending time with Bob. He had her laughing most of the time in the car and at the restaurant.

“You look incredible, Alice,” Bob said, taking her hand, slow dancing with her as the orchestral arrangement played in the background.

“Thank you,” She smiled.

“So tall too. You don’t have a boyfriend?”

“No, I haven’t had much luck in that department.”

“That’s a pity. I have a theory that sometimes, women as beautiful as you might have trouble dating. I think some men are intimidated by someone as lovely as you, so they don’t even bother asking you out.”

“I don’t know about that,” Alice blushed.

“It’s just a theory. But who knows?” Bob chuckled. They continued dancing.

“Are you a grandfather?” Alice asked.

“I am. I’ve recently met a few of my grown grandchildren.”

“You’ve never met them until recently?”

“That’s right.”

“I’m sorry,” Alice frowned.

“Oh no, please, it’s fine. It’s all very good situations,” Bob said. He pulled her I closer, his hand on the small of her back.

“I’m having a wonderful time, Bob,” Alice said.

“It’s going to be a wonderful night, darling,” Bob said. Their eyes met for a moment, and then Bob led her back to their table.

Alice downed her wine, not caring that Bob’s hand was on her exposed thigh. The waiter poured her another glass; she sipped it, glancing at Bob. She placed her hand on his.

Chapter 11

An hour later, Bob, his hand around Alice’s waist, led her to his office. She needed help due to the wine. Bob retrieved some champagne from the small refrigerator in the corner, pouring her a glass. She giggled and took it.

“Will you sit on my lap?” Bob asked.

“Huh?”

Bob chuckled, taking a seat, grabbing her by her waist and guiding her to his lap. As Bob’s computer was booting up he breathed in Alice’s scent, her arm around his shoulder, a hand occasionally playing with his white hair, the other bringing the champagne to her lips.

She watched him open up various files on his computer, images of houses, undeveloped land, and blue prints.

“What are you showing me?” Alice asked, sitting the empty glass on his desk.

“My little special project. I have built a neighborhood. Almost done actually. In this neighborhood are houses. In the houses will be families. The families,” Bob paused, kissing Alice’s exposed arm, “are very, very special.”

“How so?”

“They all love each other in very unique ways. I have been looking for people to fill these houses with their families. I have been issuing challenges to those people to see if they have what it takes to live in this special neighborhood.”

“So there’s other people you’ve challenged?”

“Yes. You are the first to know of my plan. I’ve issued several challenges already. I’m hoping I’ll hear from some of them soon. Your mother was the first that met part of hers. She did it in record time too. My first challenge was three months ago, in January, to a woman to seduce her son. I haven’t heard back from her yet.”

Perhaps the alcohol prohibited Alice from being disgusted by this, perhaps it was what her mother said the other night in Miami – everyone in her family living together, loving each other.

“Bob, I don’t know,”

“What to say? I hear that a lot,” he laughed.
“Why my mom? Why me?” Alice asked.

“Well I’ve known your mother for many years. I’ve been sleeping with her for that long too – when we see each other, a couple times a year. She’s earned and saved my company massive amounts of money. I figured I’d issue a challenge to her to see if she has what it takes to move into this incestuous haven I’m building and as a creative way of thanking her for making me more money.”

“Why couldn’t you just give her a bunch of money to thank her?”

“Because that’s boring,” Bob smiled. “Not only that, but if she wins all this money by completing my challenge she will, in turn, win something far more precious than millions of dollars.”

“What?”

Bob didn’t answer for a moment, reaching to caress Alice’s cheek, “Think about it.”

It took Alice a moment before she realized Bob meant a loving, sexual, perfect relationship with her family.

“Well why me? Why did you suggest me to help her?”

“Due to the buyout you also happen to work for me.”

“Yeah but Angela is a model for Elite Magazine, you own the publishing company, so she sort of works for you too, right?”

“Watch this,” Bob nodded to his laptop, bringing up folders and files. “Ready?” he asked before opening a video file. Alice nodded.

The video footage was of Angela having sex in a bathroom stall with one of the male models for the magazine. He was behind her, slamming into her, shaking the stall. Alice winced and looked away; Bob closed the file and opened another one. It was of Angela on all fours, on the desk of a photographer. He was behind her slamming into her, her ass rippling from the impact. He pulled out and tapped his cock on her ass cheeks a few times.

“Do I need to open another one?” Bob asked.

“No! Please, no, I get the idea. She sleeps around.”

Bob opened another file. This was video footage of Alice in the new office building she had to move to. She was alone, adjusting her makeup. The next file showed her sitting alone, in a cafeteria, eating her salad. Another showed her alone, walking down the hall to a copy machine.

“Notice a difference?” Bob asked.

“I’m alone.”

“I could’ve easily suggested Angela to help, but when I look at you there, I see a quiet sadness. I see someone who’s lonely, I see a woman who may have higher standards than Angela, but is missing out on so much fun. This challenge could introduce you to a love that’s greater to any sort of romantic or lust-filled love.”

“Bob, I – ” she said, tears welling up. He had a point, she didn’t like the men Angela hung out with, but deep down there were jealousy issues toward Angela’s social life.

Bob clicked a few times and brought up a window with a live feed video playing. The footage was of her, sitting on Bob’s lap. “There you are. Gorgeous,” Bob moaned.

“Here I am asking you to help out your mother and experience the most amazing love imaginable. There you are sitting on my lap, not alone. Will you help her?” Bob asked.

“I don’t know,” She fought to keep tears from flowing. “It’s wrong.”

Bob opened another file. It was of Lisa, slowly riding and grinding Bob’s cock in that very same chair he and Alice now sat in. Alice stared at Lisa’s breasts moving, her head thrown back, “So much money,” Bob whispered. “She needs your help.”

*****

Bob’s double master bedroom door swung open. Bob and Alice entered, kissing passionately, moving backward toward his huge bed.

He was undoing and removing his tie, she was unbuttoning his shirt. Alice, constantly kissing him, managed to slide her dress over her shoulders, while Bob unbuttoned and unzipped his pants. He guided her to his bed, she fell onto her back, Bob slid his boxers down, stepping out of them, Alice finished removing her dress, throwing it to the side of the bed.

Bob dove down on top of her, resuming their kisses, her hands messing up his white hair, his hands pulling at her thong. When he removed it, he sat up, smelled it and tossed it to the side. She removed her bra and lunged toward him, guiding him to his back.

“Careful, darling. It’s been awhile since I’ve been with a woman as young as you,” Bob said. Alice replied with more kisses, her hand guiding his cock to her pussy. She settled down on him, Bob sat up, holding her, his hands going up and down her back. They broke their kiss, staring into each other eyes, Bob thrusting and Alice grinding against him in sync with each other.

Not looking away from each other as they fucked; Bob grit his teeth, Alice’s mouth hung open.

“Come on, yes! That’s it!” Bob grunted, only to be met with primal grunts from Alice in return.

“All that money! All yours!” Bob continued thrusting, Alice’s breasts jiggling from each impact.

“Cum for me! Cum! Are you going to help your mother?” He asked.

“Ahhh, ahh! Yes! Yes!” Alice cried out, climaxing. “Ohhhh yes!”

“Mmmm,” Bob moaned, his cock erupting, filling Alice.

He held her for a moment, before falling back on the bed. “Good girl,” He whispered. “Good girl.”

Alice slid off him, out of breath, semen oozing from her pussy.

Chapter 12

Lisa greeted Bob the next day when Fat Rob dropped her off. She limped inside, joking about being sore. Alice rolled her eyes, greeting her mother wearing only one of Bob’s large t-shirts.

“How was your night?” Lisa asked.

“I think I need to go to Los Angeles,” Alice replied.

“Alice?”

“Bob will pay the airfare for my ticket; he’ll even handle the shipping of my work computer and everything. I can work from home and try, I repeat TRY, to seduce Lenny.”

Alice began gathering her clothes and luggage, her mother looking on. “Bob and I had some discussions last night,” Alice removed the t-shirt, revealing her naked body to her mother, while she kept packing. “In short, he convinced me to help you.”

Lisa eyed Alice’s frame, her eyes drinking in her daughter’s long legs and large breasts, “Well, that’s great!”

“Yes. I’ll figure something out.”

“Maybe we can – ”

“No, we aren’t blindfolding Lenny, drug him, or getting him drunk. It has to be 100% mutual if I’m going to do it,” Alice insisted.

“Fair enough,” Lisa agreed. “We’ll think of something.”

Alice finished packing, put on some clothes, and waited for her mother to gather her things. Alice watched Lisa undress, taking in her curves, admiring her mother’s body. “You look nice, by the way,” Alice said.

“Well thank you, sweetie.”

“Maybe you and Lenny should do it instead. You are certainly attractive. Any 18-year-old would love to get a piece of you I’m sure.”

“That has crossed my mind,” Lisa said, picking out some clothes. “He’s got a nice size down there.”

“Oh you saw it?”

“Mmhmm, by accident. It happens.”

“Well then, I suppose I might actually enjoy this.”

“I know I would,” Lisa muttered.

*****

Lenny had been home alone for a couple weeks. To an 18-year-old horny teenager, this was a dream come true. The only time he saw any people was when he was at school. Upon arriving home, he stripped naked, masturbating until he fell asleep, resuming in the morning before class.

The number one woman he jacked off to was one whose pictures he downloaded and saved to his computer. He looked at them every day. They were picture galleries for various photo shoots. He even managed to download a behind-the-scenes video of one of the shoots.

Lenny was sad this day, because he knew his mother would be home by the time school let out. He hoped the house was clean enough so the short, sassy, little woman wouldn’t scold him. When she did, by sticking her finger up at him, he almost couldn’t help but laugh. Lisa would get angrier, demanding he stop laughing at her, sometimes even laughing at herself. The image of a 5’2”, busty, brunette scolding a tall, lanky 6’2” teen was admittedly comical – even to her.

Since he was the only one living at home, he and his mother bonded, becoming closer, almost like friends. Lenny wondered if it was because she was dating a younger guy or if it was because she accidently walked in on him getting out of the shower. Lenny never forgot the look of shock mixed with admiration for that split second on his mother’s face. Lisa apologized profusely afterward.

That morning when Lenny shot his load one last time before his mother got home, he wondered why he never thought of her. He’d always shake his head when thoughts of her large breasts popped into his head when he was jacking off. He told himself he wasn’t like that. No, he had another main girl in his fantasies. For some reason lusting after this particular woman didn’t feel as weird.

When Lenny arrived home from school he was surprised by Alice. He didn’t know she was visiting. Lisa jumped up from the couch, giving him a huge hug, ushering Alice to join her. Alice gave him an awkward hug, trying to press her breasts again him, but not following through. Lisa told her to take it slow if she wanted it to be mutual.

At dinner they talked about Alice staying for awhile. Taking her mother’s suggestion, she flirted with Lenny, asking if she could share his room with him, giving him a kiss on the cheek when she got up for seconds. It didn’t seem to have an effect on him.

Later that night, they watched TV, Lenny sitting in between his mother and sister. Alice leaned against him, feeling awkward as she did.

When Lenny got up to go to bed, Alice said she was too, followed by Lisa. Alice jokingly suggested Lenny sleep in his mother’s bedroom with her and Lisa. He politely declined.

Alice and Lisa feigned disappointment, “What 18-year-old wouldn’t want to share a bed with two women?” Lisa asked. Lenny rolled his eyes and went to bed.

“I’ll share a bed with you,” Alice told Lisa, hoping Lenny would hear.

Alice headed down the hallway, Lisa right behind her, playfully slapping her ass. They undressed again, changing into pajamas, trading glances at each other’s bodies. Lisa curled into Alice’s arms, using a breast for a pillow.

“Are you still going on your single’s cruise in July?” Lisa asked.

“Yep, might as well. Even if things work out with this challenge.”

“Well there’s no pressure on you. If you are able to seduce him, then so be it. If not, we’ve already won a lot of money.”

“I know mom, but Bob really opened my eyes to things.”

“He is pretty good in bed, isn’t he?” Lisa grinned.

“Yes he is,” Alice replied, holding her mother close, smiling.

Lisa rose up, kissing Alice goodnight on the cheek, both falling asleep in minutes after a long day of travel.

Chapter 13

It was an absolute failure. Alice felt nothing but foolishness every time she flirted with her brother. She even jokingly suggested he dump his prom date and take her instead. He gave a fake laugh, shaking his head against that idea.

“It’s ok, sweetie. Spend time with me instead,” Lisa comforted her daughter; snuggling up to Alice on the couch after Lenny went to the prom. Alice held her mother close, feeling disappointment in her attempts to get closer to Lenny fading.

Lisa didn’t have it much better. She often wore scantily clad clothing, including yoga shorts and sports bras for exercising. Lenny only gave a glance here and there. Lisa even tried changing in front of him, as if he wasn’t there, only to be met by a “geez mom” or a “don’t you have a bedroom to change in?”

Lisa thought it was somewhat amusing, but seeing Alice get down on herself made her feel bad. Lenny seemed immune to Alice and Lisa’s flirts.

At Lenny’s high school graduation, Alice felt even more foolish clinging onto Lenny’s arm like she was a love sick girlfriend. Lenny even politely had to withdraw his arm from Alice’s grasp. Nothing was working.

That night when Lenny was at a graduation party at a friend’s house, saying “no thanks” to Alice’s offer to accompany him, Alice found herself once again holding her little mother on the couch. She was like a teddy bear to cuddle with. Alice felt better each moment she held her. Lisa would kiss her cheek when she left the couch for something and kiss it again when she returned.

Mother’s Day arrived. Alice spent the day with her mother, after Lenny presented her with a card that morning. They went shopping, Alice buying her mother some jewelry, Lisa buying her daughter some lingerie. “Gosh, you are one sexy woman, Alice,” Lisa complimented her daughter when Alice tried on the lingerie for her in the changing room.

“Well, it takes one to know one, mom,” Alice smiled, giving her mother a peck on the lips.
That evening after dinner with Lenny, Alice all but giving up on flirting with him, mother and daughter found themselves in Lisa’s bathtub. It wasn’t as spacious as Bob’s, but they both fit in there.

“You know we have $20 million dollars. I cashed the checks after I made copies of them. We don’t need to keep going,” Lisa suggested, her foot resting on the side of the tub.

Alice grabbed it, massaging it, one final gift for mother’s day. “I want one more shot before we throw in the towel.”

“It’s up to you, but I’m happy, slightly regretful, but overall happy of what’s happened so far,” her mother said.

“I thought about telling him, honestly, what was going on. But I chickened out,” Alice said, lowering her head, releasing her mother’s foot.

“Alice, please,” Lisa sat up in the tub, leaned over to Alice, bringing her lips to hers, kissing her softly. “It’s fine, really it is. We’re millionaires already.”

“I know, but I could’ve,”

“Shhh,” Lisa kissed Alice’s face again. “If you are able to go through with it, fine, if not, that’s fine too.”

Lisa kissed her a third time, backing away, standing in the tub, “Now, I’m going to bed. I’ve had a wonderful Mother’s day, and I’d love it if you joined me.”

Alice watched her mother step out of the tub, dry off and pick out some pajamas. “I’ll try once more and that’ll be it,” Alice thought to herself. Minutes later she was drying off too. She put on some panties and a t-shirt and joined her mother in her bed. Alice hadn’t set foot in the guest room in the couple weeks she had been there.

*****

Alice took Lenny to dinner the next night. She, again, flirted, complimented him, hung on to his arm and so on. Nothing seemed to faze him. He was polite as always, but the look on his face was a mixture of confusion and annoyance.

Back home, snuggling with him on the couch, Alice figured she’d introduce wine into the equation. He protested at first. Alice asked her mother if it was fine. Lisa said she was thinking of having a glass too. Alice poured some for herself and Lenny, resuming her position on the couch next to him.

Lenny watched his mother leave the kitchen, making her way back to her bedroom, before he took a sip. Alice watched and nodded, taking her own sip.

One glass, two glasses, another and a fourth, Lenny consumed. He had no experience with alcohol so by the fourth glass he was pretty drunk. Alice listened to him slur about nonsensical things, regretting that she got her little brother drunk in a last desperate effort to seduce him weighing on her mind.

Lenny rested his head on Alice’s shoulder. “You, you know Angela?”

“Yes, she’s our sister, I know her.”

“I think she’s great,” Lenny slurred. “I mean, if we weren’t related, wow.”

Alice felt worse. “I think she’s so pretty. Does she have a boyfriend?” an intoxicated Lenny asked.

Alice cleared her throat, “Uh no, I don’t think so.”

“Ok good. Maybe one day I’ll see if she wants to be my girlfriend,” Lenny added, chuckling at his joke.

“Yeah,” Alice sighed.

“I’ve always had a crush on her, but please don’t tell her!” Lenny burped.

Alice said nothing. She was done. There was no point in continuing. “Ok Lenny, I think you should head to bed. Let me help you.”

Alice pulled him up with her, his arm around her waist and she walked him to his bed room, “Goodnight Lenny.”

Lisa was watching TV in her bedroom. “How’d it go?”

Alice plopped on the bed, saying nothing. “That bad? Listen, it’s fine. Don’t beat yourself up over it,” her mother said.

Alice shook her head and sighed. “I’m sorry.”

“No. Don’t apologize. I’m the one that should apologize to Jules and Angela. We are done with this and I’ll be confessing what I’ve done to them in the near future. It’s over, we can relax now, you can go on your singles cruise and I’ll confess what I’ve done. Whatever happens will happen.”

“Ok, mom,” Alice rolled over, resting her head on Lisa’s lap.

She ran her fingers through her hair for a few minutes, “Maybe you should go check on Lenny, make sure he’s ok.”

“I will,” Alice replied, sitting up, leaving her mother’s bedroom.

Lenny’s door was cracked open; he was in his room alone, mumbling about something in a drunken stupor.

Alice stopped outside and listened. She couldn’t make out what he was saying so she opened the door a little wider and peeped in. Her eyes shot open with shock. She saw her brother furiously stroking his cock to pictures on his computer. They were pictures of Angela.

Alice watched him close out the image and then open a video file. The video was her doing an interview, then showing shots of her posing in bikinis. Alice saw enough, quickly making her way back to her mother’s room.

In her mother’s arms, a mixture of anger and jealousy overtook her. Lisa kissed her head, holding her tightly, whispering that it was ok, that it didn’t matter. Angela had a social life, a sex life, and now the lust of a brother that Alice attempted, but failed, to capture.

The next couple weeks Alice and Lisa were inseparable. They spent time visiting with family members, they did some shopping and site seeing, and every night they would either take a hot, relaxing bath together, or a shower discussing their plans for the next day. Alice would always hold her mother in bed, her warm little body providing comfort.

Alice headed back to Miami in June, signaling the end of their challenge. She awkwardly hugged her brother goodbye, hug and kissed her mom a few times on the lips, and left. She returned to a different, but similar life. Alice and Lisa would still work despite being millionaires. The only difference was a possibly occasional luxury vacation each year with the entire family, provided Jules and Angela could forgive Lisa once she confessed.

Alice waited for July to approach, only talking to Angela sporadically, politely declining her requests to hang out. The fact her brother had a crush on Angela still stung, almost serving as a reminder, as further proof that Angela was more likeable than she.

Chapter 14

Alice’s single cruise was a disaster. She had a horrible time. Nothing seemed to work out for her. On the way home from the airport, she cried, the thoughts of millions of dollars not making her feel better. She wanted her mother, she wanted to call Lisa, she wanted to hold and be held by her.

When Alice returned home, she found her. The one woman that could make things feel better. Her mother was in her apartment, waiting for her daughter.

“Mom!” Alice cried, running into her arms. “It was horrible.”

“It’s ok, I’m here, I’m here,” Lisa comforted Alice, on her tip toes, her neck arching back as Alice hugged her.

“I don’t think anyone likes me,” Alice sighed.

“No that’s not true. I like you,” Lisa joked. “That’s why I came to surprise you.”

“When did you get here?”

“Yesterday. I used my spare key and let myself in.”

“Why?

“Because I love you and I wanted to visit you,” Lisa smiled, taking Alice hand leading her to the bedroom.

They sat on the edge of the bed, Alice wiping her tears, “How’s Lenny?”

“He’s fine. Everything is fine. He and I are just normal mom and son. Things are getting back to normal,” Lisa pulled in Alice for a long embrace.

“Have you told Jules and Angela about everything?”

“Not yet, darling, I will soon though,” Lisa held Alice, kissing her head while she continued sniffing.

“I hope I can get back to normal too,” Alice said.

Lisa ended the embrace, taking her daughters face, brining it in for a sweet kiss on the lips, “You are normal, you’re perfect.” Lisa kissed her again.

“Thank you,” Alice said

Lisa rested her forehead against Alice’s, “Don’t worry about that trip or about anything. I’m here now.” Lisa kissed Alice once again.

“I’m glad you are,” Alice whispered.

“Me too,” Lisa smiled, kissing Alice once more, slower this time.

They traded several more soft kisses. “You’re so beautiful,” Lisa said, in between kisses.

“So are you,” Alice replied, kissing Lisa, playfully nibbling her bottom lip.

“I love you,” Lisa said breathlessly, kissing Alice again, quickly removing her t-shirt.

“Mom, should we – ”

“Shhh, it’s fine. Let’s just enjoy this,” Lisa said, helping Alice remove her shirt as well.

They kissed once more for several seconds, moaning when their tongues touched. “Mom.”

“Mm, yes, my darling?” Lisa whispered, in between kisses.

“Make love to me,” Alice answered.

“I’ve wanted to for a long time,” Lisa smiled, kissing her again, guiding them both to lay on their sides.

The shorter Lisa rolled on top of Alice, removing her bra, arching her breasts to Alice. Alice took one, squeezing it, kissing the nipple, licking it, then sucking it. Lisa moaned, running her hands through her daughter’s long hair.

“Oh Alice,” Lisa said. Alice switched to the other breast, giving it equal attention. Afterward, Alice rolled Lisa onto her back, kissing at her neck, breasts, and stomach. Alice slid off the bed, hooking her thumbs in her mother’s shorts, pulling them and her underwear off.

Alice stood, removing her own bottoms, then went to her knees before her mother. Lisa was lying on the mattress, legs spread wide, and running her own hands over her body as Alice’s mouth devoured her. Alice sucked her clit, lapped at her labia lips, swirled her tongue all around inside her. Alice moaned, loving the taste.

Lisa couldn’t hold out for long, within minutes she was convulsing and writhing about in ecstasy. It was the first pussy Alice had ever tasted and in that moment, considering everything that had happened, her horrible and uneventful trip, her failures with Lenny, her dismal social and sex life, it was the best thing she had ever tasted in her life. Alice wanted more.

She collapsed next to her mother, “I’m not done. I want to eat you more.”

Lisa nodded, turned around, and lowered her pussy to Alice’s face in a 69 position. Alice nearly came when she felt Lisa’s tongue enter her.

The next 30 minutes were filled with moans, cries, climaxes and pussy juice covered faces. When their jaws and tongues grew tired, mother and daughter held one another, kissing and licking at each other’s faces.

“One more time,” Lisa said, guiding Alice’s pussy to meet her own. “Do you know what to do?”

“I think I can figure it out. Grind them together?”

“Yes, darling, it’ll be wonderful,” Lisa said, sitting back, looking into Alice’s eyes as the two women began their pussy grinding ritual.

The bed was bouncing with them, the mattresses squeaking. They came several times as their pussies kissed and licked at the other with a small clitoral tongue.

Bob’s camera was on, mounted on a drawer, recording the entire event, unbeknownst to Alice.

Chapter 15

Lisa sat on the edge of Bob’s desk. Jules, Angela, and Alice sat in chairs facing her, a few feet away. Bob was behind them, leaning in the back left corner of his office, watching. It was a few days after Alice and Lisa made love. They had decided to come clean with everything, Bob, again paying for all travel fees.

“I want to tell you two something, and I’d like you to not interrupt me. You may want to, but please just let me finish,” Lisa spoke to Angela and Jules. “I want to tell you why we’re all here today.”

Lisa held up two pieces of paper. Each had a photo copy of $10 million dollar checks written to her by Bob. Her two daughters looked confused, staring at the amount, looking to each other as if the other had an answer. Their answers would come.

Lisa did her best to keep from crying, her words were shaky, but she continued. “Jules. I know what you are doing in your spare time. I know where you work. I know what goes on at your work.”

Jules’ eyes darted to her right, to her sister Angela.

“I bought you for an hour,” Lisa said, wiping her eyes. “I made sure you were blindfolded so you wouldn’t see that it was me.”

Lisa paused, taking a deep breath, “We had sex and that’s how I earned this first check.”

Jules’ head hung low as she nodded, taking Lisa by surprise. She figured her daughter would be furious. She continued on to Angela.

“Angela,” Lisa’s eyes filled with tears. “That Rodney guy had pills on him. He had a container of them in his pocket. He admitted they were to sedate girls. I have no idea if or when he’s used them before or if he just carries them around in case he feels the need to use them. In the bathroom of that club, I told him to put something in Alice’s drink. He obliged. I told Alice to switch her drink with you.”

Lisa wiped her eyes again, “Then I took you home and,” she shook her head, struggling to get the words out. “I’m so sorry. I took you to Alice’s and we had sex. You were barely awake. Please, please forgive me,” Lisa bawled, struggling to wipe away tears before more fell from her eyes.

“I earned this second check from that. Bob challenged me to have sex with my children. I accepted the challenge. He paid me 10 million per child.”

Bob cleared his throat, making his way to Lisa, pulling out a check from his wallet, “Here’s 10 more for Alice.”

Alice’s eyes widened, “Mom?”

“I’m sorry. Please, don’t hate me. You and I, it was just happening so fast. I figured I’d turn on the camera and record it. I never planned on you and I doing it. But once we started, the greed took over. Please believe me, I enjoyed it so much, I loved every second of it because I love you. Please don’t hate me,” Lisa cried.

Alice shook her head, “I, I don’t mom. It’s fine.” Alice glanced at Bob, he offering an encouraging smile.

“I just thought about the money and about what we could do with it,” Lisa said through more tears.

Jules cleared her throat, “Fat Rob told me it was you. The next day he said you came by to buy some time with me and wanted me blindfolded for it. I didn’t recognize your smell. I didn’t recognize your touch either. You never touched me like that before. You never kissed me like that before.”

Jules extended her hand and patted her mom’s knee, “Mom, it was amazing. I felt sick after Fat Rob told me. But then I thought about it. It was so beautiful. I’ve never been blindfolded during sex before. Not only was it amazing, but so was your touch, your kisses, your licks, everything.”

Jules closed her eyes, thinking fondly, “Mom, please don’t feel bad. I don’t any more once I thought about how wonderful it was.”

Angela cleared her throat to speak next, “I knew it was you mom. I was out of it. I wasn’t coherent. But I could see. My vision was very blurry. But the light from the lamp made you appear angelic. Like Jules said, the way you touched, it was,” Angela paused.

“I didn’t want it to end. The only time I was angry was when I saw your blurry figure move away. I was angry because I wanted you to hold me all night. I wanted you to stay with me,” Angela patted Lisa’s knee too. “I felt odd the next couple days, thinking maybe it was a dream, but if it was it was the best one I ever had.”

“There was more to my challenge, remember?” Bob asked Lisa.

Lisa wiped her eyes again, “Yes. I would be paid extra money if I got one of my children to seduce at least one of their siblings.”

“How much?” Jules asked.

“Everything would be doubled. If one of you seduced your sibling, we’d get $20 million for it instead of ten. Plus I’d get paid retroactively for any of you I already slept with.”

“A grand total of $80 million could be earned,” Bob added.

Alice spoke up, “I was going to help. I was going to be the one to seduce Lenny. But I couldn’t do it. I didn’t want to drug him or deceive him; I wanted it to be mutual, consensual. But I couldn’t do it. No matter how much I tried.”

Alice turned to her left, “Angela. He admitted to me he’s always had a crush on you. I found pictures of your photo shoots on his computer. He’s head over heels for you. I couldn’t go through with it.”

Alice started tearing up next, “I was hurt, but didn’t understand why. Then I realized I was jealous. Not because my little brother had a crush on you, but it was one more thing on top of everything else.”

“What do you mean?” Angela asked.

“You’re always having fun. You have a great social life. You have a great dating life. And, well, a great sex life. I have none of that. I don’t like some of the people you hang with, but I don’t have anyone to hang out with at all!”

“Alice, it’s ok,” Angela, reaching over, holding her crying sister.

“Now I’ve failed you mom,” Alice looked to Lisa.

“No, you haven’t, you haven’t at all. If anything, out of you and me, you are the one with the morals. I was the one that jumped right into this challenge without thinking,” Lisa said, holding Alice’s hand.

“I still want to help, I still want to help you, I mean, us earn as much of the $80 million as we can.”

“Oh sweetie. Alice are you sure you want to try again with Lenny?”

“No, I don’t want to, but Angela could,” Alice turned her gaze back to her sister. “Think about it. Please? He has all your photo shoots downloaded from the internet, even some video from the Elite Magazine website. I caught the poor kid jacking off to them!” Alice smiled weakly.

Bob spoke up once more, “I know of a wonderful resort in the Bahamas a brother and sister could go to for a nice vacation. I’ll be glad to send you and your brother there, Angela.”

Angela looked to her smiling mother and siblings, “$80 million dollars if I have sex with him?” They all nodded their answer.

Angela paused, taking a deep breath, “I’ll do it.”

Chapter 16

Bob let the four women stay in his home that evening. They each had their own bedroom and bathroom. Lisa couldn’t sleep; none of her daughters could either. She got up, adjusted her bath robe and walked toward Bob’s bedroom.

Lisa’s eyes shot open when she entered Bob’s master bedroom. He was sitting on the edge of his bed. Jules was naked, on her knees in front of Bob, her head bobbing and weaving to and fro on his cock.

“Lisa!” Bob gasped when he saw her.

“Oh hey mom. I was horny, so, you know,” Jules giggled.

“Yes, you came to visit Bob,” Lisa observed.

Jules stood, making her way to her mother, grabbing her, bringing her face up to her own, kissing her. Lisa tasted Bob’s cock on Jules’ slithering tongue.

Jules broke the kiss. Lisa moaned, taking a step back, removing her robe to reveal her naked body. Mother and daughter held hands as they made their way to Bob.

Alice couldn’t sleep either. She was wandering around the first floor after a long bath, admiring the various works of art that lined the hallways. In the distance she saw someone standing at a balcony that over looked the swimming pool. As Alice got closer to the figure, she could see it was Angela, wearing a similar bathrobe as Alice.

“Hi,” Alice said, standing next to her sister.

“Hey.”

“Couldn’t sleep either?”

“No,” Angela chuckled.

“Yeah, you have a lot on your mind I’m guessing.”

“I do,” Angela said. “I’m trying to think how to go about this.”

“Mom told me to flirt with him, but I was so awkward. When Lenny admitted he always had a crush on you I figured I wasn’t the one to help with this challenge. You’d be better for it than me.”

“I’m sorry Alice.”

“For what?”

“Everything. I tried to help you. I tried to push you to hang out with me and my friends. I should’ve backed off; I know they aren’t your cup of tea. I shouldn’t have assumed we’re the same.”

“No, I’m sorry too. I should’ve been nice about it. I just look at you and I see someone so gorgeous and happy. It was wrong of me to look down at you. If you are happy and not hurting anyone, who am I to judge? The whole incest challenge thing has opened my eyes a little I guess.”

“Yeah we’ve made love to our mother,” Angela chuckled.

“Mmhmm. Have you ever been with a woman before her?” Alice asked.

“No, you?”

“Nope. I’m not a lesbian, but it was – ”

“Amazing,” Angela finished Alice’s sentence.

“It was. She’s the only woman I’d ever do something like that with again.”

“The only one?” Angela turned to Alice.

“Well, maybe not the only one,” Alice replied shyly.

“Alice you are so perfect. You’re tall, you have a beautiful face, a great figure. You really are one of the most beautiful women I’ve ever seen,” Angela hugged Alice, holding her tightly.

“You are too, Angela. I should’ve given you more compliments. You have a great figure too. Nice breasts, and um, well, this,” Alice said, reaching behind her sister, patting Angela’s butt.

Angela ended the embrace, looking in Alice’s eyes. “Lenny will no doubt enjoy playing with this,” Alice said, still patting Angela’s butt.

“You think?” Angela pulled up her robe, revealing her bare ass. Alice squeezed and massaged it, nodding her head. Alice gave Angela a sly grin, nodding her head.

Alice released Angela’s ass, brought her hands to her face, kissing her tenderly. The two sisters took a step back, disrobed, held hands and made their way to the pool below.

In Bob’s room, Lisa and her youngest daughter were busy servicing his cock. Leaning back on his bed, watching the mother and her child go to work, thinking how beautiful a sight it was.

Jules’ and Lisa’s eyes were locked on one another as their tongues went up and down Bob’s shaft. It wasn’t long before he was ready to explode. Bob stood, guiding the women to their knees in front of him, jacked his cock several times, grabbed Lisa’s head, forcing her mouth over it and filled it with semen.

Lisa moaned at the taste, grabbing Jules’ head, and bringing her mouth to her own. Jules opened wide, accepting Bob’s cum from her mother’s mouth, moaning at the combined taste of it and Lisa’s saliva. Jules sloshed it around her mouth a moment and did the same to her mother. Lisa swished the semen around, and then pulled Jules in for a kiss, their cum-covered tongues dancing with each other.

“No blindfolds this time,” Jules said, pushing her shorter mother to the carpeted floor, kissing her neck, breasts, stomach, and finally driving her tongue into Lisa’s pussy.

Lisa gripped Jules’ short hair, holding her head in place, while Jules’ tongue swirled around inside her. Bob spent from earlier, watched nearby, soaking in the sight before him, while Lisa’s pussy was simply soaking.

Jules’ hands roamed over Lisa’s body as she worked, licking, and sucking at her clit, occasionally dipping her tongue back into Lisa’s depths to recoat it in vaginal fluids.

Out at the swimming pool that very moment, Alice was licking something else. Angela was on all fours in the shallow end while her sister was behind her, licking away at her anus. Their intense make-out session upon entry into the pool ended when Alice turned Angela around, guided her to her hands and knees, spread her cheeks apart and dove in, showing her admiration of her sister’s ass much like Lenny only dreamed of.

When Angela could take it no more, she rose up and tackled Alice into the water, kissing her passionately. Alice sat up; returning the kisses, pushing Angela off her, their legs becoming entwined.

Slowly they guided their pussies to meet, their eyes not looking away from each other. Grabbing each other’s face one last time, giving each other a powerful kiss, they began. Clit against clit, grinding and bouncing, water splashing out of the pool, the two sisters made love. Moaning and crying with ecstasy, they cut any hard feelings they had had away with their pussy grinding scissoring.

In Bob’s room, after Lisa climaxed from Jules’ tongue assault, mother and daughter found themselves in a similar position. Arching their backs, the two women climaxed at the same time. They collapsed on their backs, their legs still tangled together. Jules ran her hand up and down her mother’s thigh, Lisa doing the same.

After Alice and Angela had their mutual orgasm in the pool, they untangled their weak legs, crawling to the edge of the pool, kissing each other tenderly. After they regained their strength, they went inside, arms around each other. Alice guided Angela down to her bed, telling her to wait a moment.

She went searching for her mother. Alice found Lisa and Jules curled up in bed with Bob. Pulling Lisa out of the bed, a moment later, Alice presented Lisa to Angela. Lisa climbed in bed, still naked, and held her daughter, kissing her head, squeezing her breasts, sliding her hand down Angela’s stomach.

“This time, after you cum for me, I will be here all night, to hold you, kiss you, and make love to you,” Lisa told Angela.

“Thank you,” Angela whispered, eyes watering. They kissed, Lisa’s fingers finding Angela’s engorged clit.

Lisa broke the kiss, staring into Angela’s eyes as she masturbated her. Alice stood at the door watching the beautiful act transpire before her.

“I love you!” Angela cried out as the orgasm approached.

“Oh, my sweet Angela, I love you so much. Cum for me my girl. Let mommy feel you cum,” Lisa said, her fingers curling deep inside Angela. “Look in my eyes, don’t look away.”

“Ahhh!!” Angela climaxed, looking into her mother’s loving face.

“That’s it, that’s it baby. The first of many tonight,” Lisa said. She held her shaking daughter in her arms as the orgasm washed over her.

Alice smiled, seeing all was well, and took her leave. She found Bob and Jules asleep in a loving embrace.

Alice tugged at Jules’ arm. She stirred, looking over to a sleeping Bob, and stood. Taking Alice’s hand, Jules followed her to another bedroom. Kissing when they entered, tasting each other mixed with the pussy juices of their mother, the two sisters made their way to the bed for their own night long love-making session.

Chapter 17

The next morning, Alice and Angela slept on their flight home to Miami, leaving Jules and Lisa with Bob. The mother-daughter team constantly serviced Bob, ensuring his balls were never filled with cum, while staying up most of the night making love to one another.

Jules quit working for Fat Rob, Lisa turned in her notice to Bob. They all talked about what to do with $30 million dollars, Bob teasingly reminding Lisa of a special bonus he had for her, should her family meet this challenge 100 percent.

Alice and Angela spent the next couple days in Miami in bed. After one particular pussy grinding session, Alice kissed her sister, wiping sweat from her face. “Are you sure you don’t want to go out with your friends?”

“Not anymore,” Angela replied. “I’d rather spend my time making love to you.”

“You don’t want to visit Rodney?” Alice asked.

“Nope.”

“Well,” Alice smiled, unwrapping her legs from Angela’s, moving to her top drawer. “How about this? Its name is Rodney too.”

Alice’s mouth dropped, looking at the large dildo, “You named it after Rodney?”

“Yes. Not because I want him, but because this is the only Rodney that will ever get inside me. A sex toy.”

Angela crawled off the bed, taking the dildo, sucking and licking the tip, “Well then, this is the only Rodney that will ever get inside me again. Fuck me with it,” She grinned at Alice.

“As you wish,” Alice grinned back, taking the dildo, kissing her sister, and guiding her back to bed.

Bob arranged everything, like always. He bought plane tickets for Angela and Lenny. Lisa called and instructed Lenny on when to go to the LAX airport. He was confused at first, Lisa essentially telling him to do it without question. Lenny shrugged at his computer, closing pictures of Angela in a bikini, closing the behind the scenes video of a photo shoot, opened up his email and printed off the flight itinerary.

Lisa wired several thousand dollars to his bank account and reminded him to save all receipts – should they spend any money. She did not tell him it would be him and Angela alone on this surprise and sudden vacation.

*****

“Hi Lenny!” Angela ran to him in the airport in Miami. She threw her arm around him, taking him by surprise, causing him to blush. He always did when she hugged him.

“Are you looking forward to this?” Angela beamed.

“Yeah, it’ll be cool.”

“I’ll say! It’ll be just you and me,” Angela told him.

“Uh, what? Just us?” Lenny asked.

“That’s right!” Angela took his arm, leading him to baggage check in.

“No way,” Lenny thought, attempting to conceal a grin.

Angela led him to check his luggage. When he was done they got their boarding passes and made their way to the long security line. “Did you already check your luggage?” Lenny asked Angela, whose arm was still wrapped around his.

“Nope, I have everything I need in my carry-on bag,” Angela replied. All she packed was some makeup, various toiletries, two small dresses, two bikinis, and nothing else – no underwear or other clothing. Angela assumed they would be naked most of the time anyway, earning every cent of Bob’s challenge.

She talked on and on and on, the entire plane ride. She asked Lenny about college, his goals and plans, assuring him it were ok if he didn’t know yet. Angela flirted too, complimenting him on how cute he was, tousling his hair, asking about his love life. She was legitimately saddened to learn he didn’t have a girlfriend, genuinely telling him that she thought for sure he would, again complimenting his appearance, his smile, his height. He reminded her of a male version of Alice.

Once they arrived, they grabbed Lenny’s luggage and got a cab; the driver made small talk with the Americans. When he asked if they were married, Angela said they were not yet married, causing Lenny to blush. Angela jabbed his side, resting her hand on his thigh.

Since Angela wasn’t wearing a bra, the cool air-conditioned taxi made her nipples hard. She saw the cab driver glance back at her through the rear view mirror. Knowing why she was there with Lenny, coupled with the sneaky driver and the fact she wasn’t wearing a bra or underwear, made her even hornier than she already was.

At a stop light, Lenny was looking off to his left at the surroundings. Angela’s eyes were locked on the driver’s. She smiled, pulling down her tank top, revealing an erect nipple to him. He smiled and nodded back, the light turning green, and drove closer to the resort.

“Free ride, no charge,” the taxi driver said, arriving at the resort. Lenny was behind the vehicle getting their bags.

“Thank you, sir,” Angela smiled, bending down, offering the driver a better view of her tits.

“That boyfriend of yours going to have a good vacation isn’t he?” The driver asked.

Angela grinned, reaching down to grab and squeeze the driver’s erection. “He sure will. Lots of sex. But he’s not my boyfriend, he’s my brother.”

The driver’s mouth dropped, watching Angela and Lenny walk away, holding hands.

“We’re going to have so much fun. I can’t wait to get in a hot tub or lay on the beach. Mom’s boss was so kind to send us on vacation here. It’s a shame she’s too busy to join us!” Angela said, holding Lenny’s hand as they walked to their room. He had no idea what was going on with his sister, she was always nice to him, but never this nice. He didn’t care, soaking up the attention as best he could.

*****

The resort was an immaculate, newly renovated, vacation spot. It had its own staff and the rooms were basically villas – each having their own back courtyard with a bubbling hot tub.

“Oh wow, this is amazing, Lenny!” Angela placed her bag on the bed, and checked out the bathroom. The shower was huge. Her first thought was that it could easily fit her and her brother in there.

“Look out here! Oh my…” Angela looked into the small courtyard, noticing the hot tub. Lenny stood next to her. Angela moved in front of him, grabbing his arms, wrapping them around her, placing his hands on her tummy. She arched her back slightly, jutting her butt into Lenny’s crotch.

“I am so glad to be here. I’m glad to be able to spend some time with my little brother,” Angela said. She flexed her glute muscles a few times against, what she thought was, an erection, smiled and made her way back into the bedroom.

Angela went back to her bag, leaving Lenny behind to blush. “I’m changing into my bikini and then we’ll hit the beach.”

A few moments later, Angela emerged from the bathroom wearing a black, tiny, thong bikini. It was one she wore on an Elite Magazine photo shoot. Lenny instantly blushed, recognizing the bikini in several of the pictures of his sister that he jacked off to.
“Well do you like it?” She asked her brother, laughing as his mouth dropped open. She approached him, grabbing his hands and placing them on her waist.

“Do you think it’s sexy?” Angela asked. He nodded, glancing down at her cleavage.

“Do you think I’m sexy?”

“I do,” Lenny answered, looking away, embarrassed.

“Good,” Angela caressed his face, bringing his gaze to meet hers. Lenny stood, looking into her eyes, paralyzed.

“Let’s have a relaxing day. We better, because we have a busy night ahead of us,” Angela kissed his cheek and walked away, her hourglass figure and nearly bare ass hypnotizing Lenny. His heart was thumping, his mind racing, thinking maybe his wildest fantasy would come true.

Chapter 18

Angela had it all planned out. There would be no ongoing games of seduction. She would spend the day with Lenny, sunning by the pool, maybe playing in the water some, they would go to dinner, go back to the room and have sex.

She didn’t ask him about sex, she didn’t ask her brother about what experience he did have, she didn’t care. When dinner was over, Angela quickly led him by the hand back to their room, ignoring his questions about why she was walking so fast. She had $20 million to earn that night – and even more on top what her mother earned.

Lenny’s gasped when Angela slammed him up against the door to their room after closing it. She stepped away from, easily pulling her light sundress over her head, revealing her naked body.

“Uh, um, Angela?” Lenny asked, unable to believe what he was seeing.

“Shh,” She pressed against him, bringing his face to hers for a passionate kiss.

“Wh-what are you doing? What’s going on?” He asked.

“I said be quiet. No talking. Just sex,” Angela kissed him again.

“But, but why? What would mom – ”

“Lenny I said no talking,” Angela stepped away from him, walking to the bed, turning around, offering herself to him.

Lenny looked on in disbelief, watching his sister sway her hips from side to side, mesmerizing him with her ass. He approached her, not taking his eyes off it. “Do you want it or not?” Angela asked, sliding her ass across his crotch.

“Oh I want it. I want it more than anything,” Lenny said, watching his sister slide her ass cheeks up and down his erection.

“Then take it. It’s yours,” Angela said, looking over her shoulder.

Lenny gulped, paused, and stripped naked as fast as he could, kicking his pants to the side, tossing his shirt.

“I want this so bad,” He said, a hand on her hip, the other guiding his cock into her oozing pussy.

Angela moaned when he entered, “Take it Lenny!”

“Ah! Ah! You feel so good,” Lenny moaned with each thrust from behind.

“Yes! Fuck me Lenny!”

“Oh Angela! Yes!”

“Keep going brother, don’t stop until you cum in me,” Angela gripped the sheets of the bed in front of her.

“I’m not!” Lenny slammed into her, her ass rippling from each impact. “Oh yes, this is unreal!”

“No it’s very real! Alice told me she caught you jacking that cock of yours off to my photos.”

“She what? She did?” Lenny stopped.

“Don’t stop! Keep going!” Angela ordered, Lenny complying. “I’ll explain everything. Cum in me first!”

“Angela, ahhh,” He moaned. “Almost there!”

Angela’s eyes rolled in the back of her head, thinking about the money, thinking about how surprisingly good Lenny felt. The thought of her family’s new life together sent her over the edge; she was cumming hard, while Lenny kept slamming into her from behind.

“Ahh yes! Yes!” Lenny’s orgasm coursed through him, his cock erupting inside Angela. She moaned again, her own climax subsiding. Lenny kept going and going until his cock felt as though it would fall off.

Angela collapsed on the bed, taking him, cock still in her, with her. She rolled over, wrapping her legs around her brother. “I have something wonderful to talk to you about. But first we need to rest. After a break, I have a camera I want to film us with.”

“Film us? Why?” Lenny said, catching his breath. Angela kissed him hard, “Yes, filming you and I doing this. Rest up; we have a long night ahead of us.”

*****

The next morning, Bob sat at his desk, while Lisa and Jules serviced his cock. He was watching footage of Angela and Lenny the software downloaded from the video stream. They were in a variety of positions. Each time after they cummed, Angela would stop the video, resuming after a break. She was on top, he was sucking her tits, or she was on her back, Lenny pummeling her as hard as he could. She set up the camera in the bathroom to film them in the shower making sweet and sensual love, Bob chuckling as the camera lens got gradually steamier from the hot water.

When the last video stream file played, Lisa stopped sucking Bob’s cock, gave him a mischievous smile, stood and made her way to the bedroom to pack.

“It’s just you and me now Bob,” Jules said. “Can I be your sex slave until she gets back?”

“I think that’s a wonderful idea. Mind if I tie you up?

“I’d love it,” Jules said, taking the man that changed her life by the hand, leading him to his bedroom.

Chapter 19

That evening Lenny was in the shower. Angela had just stepped out and began getting ready for a dinner date, celebrating their completion of the challenge. She slid on another dress she had brought and was doing her makeup when there was a knock at the door.

When she answered she saw an employee of the resort. “Hello ma’am there’s been a noise complaint against this room. We both know the cause.”

“Oh, uh, yeah, we’ll keep it down,” Angela looked away.

When her gaze returned to the employee she saw a small arm reach around him. The little dainty hand found the employee’s belt. The other mystery hand joined in and assisted the other with unbuckling the belt, unbuttoning the pants, and unzipping them. The two small hands fished out the employee’s cock, slowly stroking it. The employee closed his eyes, moaning, while Angela thought those little hands looked familiar.

Lisa peeped around the taller employee smiling at Angela. “I thought that was you!” her daughter laughed.

“Mmhmm. Mommy is making a surprise visit. But not to you, to my son. Do you think you and this nice employee, who just got off duty, can spend a little time together?” Lisa asked.

“Well,” Angela looked back toward the bathroom where Lenny was still showering. “How long do you need with him?”

“All night,” her mother answered.

“I have a key for an unoccupied room in the villa next door, ma’am,” The lucky employee said.

Lisa said nothing, moving to the front of the employee, still stroking his cock.

“Let’s go then,” Angela winked at her mother. “You filming it? You and Lenny?”

“No. This is mommy’s special time with him. Not filming it, not for money – just love,” Lisa said, stepping into the room.

“Well, then, I’ll see you tomorrow mom,” Angela walked past Lisa, taking the employee’s arm, his cock still dangling out.

“We’ll be next door, ma’am,” He said, closing Lisa in.

She looked around the room, thanking Bob for sending her here on short notice. Lisa sighed a sigh of happiness. She undressed and waiting for her son to exit the shower.

*****

“Mom! What are you doing?” Lenny said, shocked to see his nude mother in the bedroom.

“I’m making a surprise visit.”

“I, uh, I can see that,” He looked away.

“I’m sure Angela told you everything, yes?”

“Yep,” He quickly replied.

“Hey, don’t be nervous, look at me,” Lisa said.

Lenny glanced at her naked body.

She approached him slowly, but quickly removed the towel from around his waist.

“Hey! What are you doing?” Lenny asked, backing away from her.

“You and mommy are going to have some fun.”

“Mom, I don’t know, I mean, I uh,”

“You did it with Angela so you can do it with me,” Lisa said.

“Yeah, but – ” Lenny said.

“I’m your mother, Lenny. Do as I say and give me that fucking cock.”

Lenny paused, his eyes trailing down his mother’s hourglass frame, taking in her body that she’s spent so much time perfecting with diet and exercise. He took a deep breath, nodded, picked her up and took his mother to bed.

“That’s it,” Lisa said, landing gently on her back, opening her legs for Lenny. “Angela is hanging out with a new friend tonight. So I’ll be taking care of this,” Lisa said reaching for Lenny’s erection, slowly stroking it.

“Are you ready? Are you ready for me to guide that lovely cock of yours all the way in me?” Lisa asked.

Lenny gulped and nodded. Lisa clamped her legs around his waist harder, trapping him in. She guided his cock inside her, Lenny moaning as it descended into her vaginal depths.

“That’s it baby, mmm, mommy loves this. We’re going to go through some changes in the near future. After this Bahamas trip, we’ll head to Atlanta for a wonderful gift,” Lisa said, slowly rolling her hips upward.

“B-Bob’s?” Lenny asked.

“Yes. Now kiss me.”

Lenny did as he was told, kissing Lisa hard on the mouth. She kept rolling her hips, grinding against him as they kissed. Eventually Lenny thrust downward into her, meeting her own pelvic thrusts. “Yes, Lenny, keep going. You are going to be the luckiest guy in the world.”

“Ahh, how, how so?” Lenny asked, thrusting faster and faster.

Lisa pushed him off her, rolling on top of him, straddling him, “You’ll find out in due time,” Lisa said kissing him again. “Suck my tits baby.”

Lenny did as he was told; they were large, but not quite as large as Angela’s. They weren’t as perky either, but he didn’t care. Sucking away at her beautiful orbs, enjoying her moans of pleasure, any weirdness slipping further and further away.

“Lenny! Yes!” Lisa said moments later, grinding herself against him, her nipples sending shockwaves of pleasure through her body as Lenny sucked them.

“Mommy loves you!” she cried out; the first of countless orgasms for years to come spreading through her body. All regret fading away, only love and euphoria remained.

Lenny guided her to her back, mounting her on top once more. “Your turn my love,” his mother said.

Lenny then began slamming into her, banging the bed against the wall, “Ahh, I love you mom!”

“I love you too! We all do!”

He looked in her brown eyes, thinking of the challenge his mother accepted, thanking her silently for doing so.

“Cum for me!” Lisa cried; another orgasm building.

“Yes!” Lenny grit his teeth and worked faster. “Ahhh, mom!”

“Yes! Yes! Keep going! Don’t stop!” Lisa was climaxing again.

“Ughhnn, so good! Yes!” Lenny impaled her one last time, holding still while his cock injected semen deep into her quivering pussy.

He collapsed on top of his mother. She smiled, holding him close. Lenny had no idea what to expect in the next few days of their vacation. But when Angela returned the next morning, she stripped, joining her naked mother and brother in bed, signaling the start of their marathon three-ways.

Chapter 20

It was the last weekend of July. Bob had written more checks to Lisa; $20 million for Angela sleeping with Lenny, $30 million to double what Lisa had already done, plus an additional $20 million, bringing their grand total to $100 million.

“What’s this for?” Lisa asked Bob.

“My security cameras caught a very beautiful display of sisterly love in my pool area,” Bob said, winking to Alice and Angela.

The sisters looked at one another smiling; having no idea their impromptu session was filmed. Lisa’s family laughed with Bob, richer than they ever imagined they would be.

“There’s more. A bonus,” Bob said. He pulled out a folder from his desk which contained photos of completed houses. “One of these houses is yours. Just pick which one you want. All of you will move into this neighborhood, this haven, and live together under one, gigantic roof. Hopefully, in time, the entire neighborhood will be filled with families just like yours.”

Lisa couldn’t believe it. She looked to Alice, tears welling up in her eyes. She looked to her other children, they all nodded in agreement. She was speechless, hugging Bob tightly, whispering in his ear, “Thank you. Find me before we leave. It’ll be you and me, one last time.”

Bob kissed her lips and smiled.

Dinner that night was enjoyable. Lisa’s family sat at the large table, drinking, laughing, and enjoying everyone’s company.

As dinner drew to a close, Angela and her mother were flirting, laughing, and eventually sneaking off together. Jules’ hand was down Lenny’s pants, jacking him off under the table. When they finished their meal, she kissed him several times, urging him to come to her bed.

Alice was alone with Bob. She couldn’t help but feel dejected, wondering if her relatives were either drinking too much or simply forgot she was there.

“Alice,” Bob whispered, standing behind her. “Come to bed with me.”

Alice couldn’t say no the man who had given her family $100 million dollars and a new home. She followed him to his bedroom, kissing, undressing, cumming over and over.

Bob held her against his body, letting her orgasm subside. “Thank you Bob. For everything,” Alice whispered.

They kissed once more, Bob sitting up, holding Alice, resuming his upward thrusts into her.

*****

A few hours later, Lenny was awake in bed. Jules was sound asleep, her naked body lying against his.

Climbing out of bed, he put on some boxer shorts, and went for a walk. Lenny walked around on the first floor admiring the various works of art that lined the hallways. In the distance he saw someone standing at the balcony that over looked the swimming pool. As Lenny got closer to the figure, he could see it was Alice, wearing a bath robe, enjoying the summer night air.

“Hey,” Lenny said, slightly startling Alice.

She turned around, “Oh, hi, Lenny.”

“Can’t sleep either?” Lenny asked.

“Not really. A lot of amazing things have happened lately,” Alice admitted.

“Yeah I know. It’s pretty crazy,” Lenny said, standing next to his sister, looking out onto the pool with her.

“Hey, um, Angela and mom told me everything. They told me you were going to try to uh, seduce me first.”

“Oh, heh, yeah, I had trouble doing it,” Alice shrugged.

Lenny cleared his throat, “Well, I didn’t realize it at the time. I guess now I’m able to put the pieces together.”

Alice said nothing, nodding her head. “If I had known back then,” Lenny said.

“Then what?” Alice asked, turning to face him.

“Well, it’s just they said you had trouble flirting and everything. I guess if I had known why you were doing it, maybe I could’ve, you know, gone through with it better.”

“Well Lenny, you told me you had a huge crush on Angela.”

“I know. But you, you are gorgeous too,” Lenny said, taking a step closer to Alice, caressing her face. “The only real reason I had a crush on Angela, was because we hung out more, she seemed interested in being friendly and getting to know me over the years.”

Alice lowered her eyes, “I’m sorry.”

He tipped her chin with his finger, “Alice.” He smiled warmly at her, “I’ve always thought you were beautiful.”

“Lenny, it’s ok, I – ” Alice was interrupted with a soft kiss on the lips.

Lenny caressed her face again, without saying another word, his hands lowered to her robe, slowly pulling it part. Alice brought her hands to his, stopping their movement. Looking into his eyes, she completed the task of removing her robe, letting it fall to the floor, standing naked before her brother.

Lenny pulled his boxers off, grabbed her hand, “Let’s go for a swim.”

“I’d love that,” Alice followed him into the pool. The played, they splashed, they kissed, and then made their way to the shallow end. Alice rode his cock hard, splashing water out of the pool, just like with Angela. After she came, he stood, taking her with him, holding her hand. He dried her off with her robe, took her inside, found an empty bedroom, and took her to bed.

They made sweet, slow, love for hours. Lenny licked and kissed every inch of her body. When he was ready to cum, he took his time, bringing her another orgasm, telling her he loved her, how beautiful she was, before blasting her insides with semen.

At breakfast the next morning, Bob joked that he wasn’t paying them anymore money for their little show in the pool; he had already given the family enough.

Chapter 21

“Hi Devin,” Lisa said on the phone before lunch. “You busy tonight?”

“Oh hey. No, want me to spy on someone again?” Devin giggled.

“No, actually I want you to have sex with my son all night. Can he come over?”

“Uh, what?”

“It’s hard to explain, but we’re at Bob’s house and I need my son to have something to do tonight. We’ve gotten closer since he graduated high school,” Lisa leaned down, kissing Lenny’s cock a few times.

“Would you believe the poor boy is a virgin?” Lisa asked Devin.

“Ah, I see. You want me to show him a few things?” Devin asked.

Lisa’s tongue licked Lenny’s testicles, him watching with a goofy smile on his face, “If you wouldn’t mind. I’ll pay you.”

“No need to pay me. I’ll enjoy teaching him a thing or two.”

“Good. Now then, he’ll show up later tonight after dinner. Pretend you’re a babysitter or a sexy mom or something like that. He’ll like it. Trust me.”

Devin agreed. Lisa had sex with Lenny for the rest of the afternoon, explaining to him that if his mother or sisters couldn’t drain his balls, a substitute would be found. She gave him directions to Devin’s. Lisa and her daughters got to work properly thanking Bob all night for $100 million dollars.

It was a long night in Bob’s bedroom, filled with sex and debauchery.

*****

The next night 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.

“I know. You’ve told me,” one of Bob’s favorite former employees reminded him. Lisa glanced out into Bob’s master bedroom, watching her four children roll around in a sweaty pile of orgasmic bliss on his king sized bed.

Lisa rose up, sitting the cigar to the side, lowering herself on Bob’s erect cock. He took one of her breasts to his mouth, sucking it tenderly.

“You going to come visit us?” Lisa asked.

Bob gave Lisa a hard thrust, “Maybe. One of my daughters has moved in with her son. I may visit them.”

“You have a daughter?” Lisa asked.

“I have several actually,” Bob answered with another thrust causing Lisa to moan.

“Have you slept with them?”

“Three of them, yes. I share a mother with two of them. On the third, I impregnated my Aunt,” Bob explained thrusting again into Lisa.

“Mmmm, naughty Bob. I suppose we’ll use Lenny, should any of us want to get pregnant.”

Bob grabbed her waist, picking up his pace, her tits bouncing with her. “Yes. More families will join you there. You’ll all live in harmony, taking care of each other in every way.”

“Ahh, Bob!”

“Cum for me Lisa, one last time!”

“Yes! Yes!” She cried out.

Bob grunted, his cock erupting in Lisa, her body flailing in the tub. After their orgasms ended, she kissed him hard, “I’m going to go join my children now.”

“Please do,” Bob whispered.

Lisa climbed out of the tub, dripping wet, made her way to Bob’s bed. The moaning, sweating, slithering bodies of her children, parted, letting her crawl into their fold. She was met with kisses, licks, sucks, and a nice hard cock.

*****

Lisa stepped out of the moving truck. She was flanked by her four children; all had their arms around each other, standing in a line, towering above their mother in the middle. Lisa looked around as they walked toward their new home in Charleston, South Carolina. Other families were moving in, just like Bob said.

After their first meal in their new home together, Angela and Jules went to an adult store to buy sex toys, joking that only one person in the house had a penis, and they needed some toys to offset the imbalance.

When they returned home, they dumped a box of strap-ons, dildos, vibrators, and a prostrate stimulator to scare Lenny with onto the floor, and then turned to the bed. The sisters smiled, seeing Alice resting in Lenny’s arm, making out with him tenderly, while their mother was on his other side, laying her head on his chest.

Angela and Jules stripped naked, climbing in bed, next to their mother. Lisa stirred, rolling to her back, smiling warmly, surrounded by her family in their new home.

The end.

************
If you’d like to know how Alice’s single cruise went, feel free to read: “The Long Absence: Ted’s Story.” She has a minor role there. Perhaps all of this challenge business was on her mind. Maybe seeing certain things transpire on that trip made her more inclined to have sex with Lisa.
************