The Challenge Ch. 05: Lisa's Family

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.