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"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."
