The Challenge Ch. 05: Lisa's Family

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."