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Lovely Lilly

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Author's note: If you aren't a fan of stories where a majority of the characters have little to no morals, please don't read this. You've been warned. Move along if this concept doesn't intrigue you. There are some evil and screwed up people in this story. The sexually active son may be the lesser of the evils.

This isn't a lighthearted love story. Its companion piece "Juicy J" is far more upbeat and lighthearted. Feel free to read that story (about Lilly's sister) if you prefer that style.

This one is also layered tale with several characters. One minor character may say something that another major character draws from later one. Things are connected. If you want a simpler tale with only two characters then please don't read this.

Editing thanks go to Todger65.

*****

Chapter 1

Lilly was crying. The slap her mother gave her caused the 36 year old to break down. Though the pain from the slap wasn't the main cause of her tears - her world was falling apart. She suspected her husband, Judd, was having an affair. Lilly also did something she vowed to her twin sister she would never do - go to their mother for help.

"Get a hold yourself Lilly!" Her mother, Darla, scolded her. "You brought this on yourself!"

Lilly wiped away her tears and nodded, sniffing, she was able to muster a quiet reply, "I just don't know what to do."

"You don't know what to do? I'll tell you what to do," Darla said, pointing her index finger in her daughter's face, "you get out there and you do what is necessary to make that man jealous and realize his errors."

"I don't have proof that he's - " Lilly countered.

"Yes you do. Your intuition. You know it's true," Darla interrupted her.

Lilly nodded once more, looking to the floor. Her and Judd's sex life had gone down the toilet, he was working later hours at the law firm, his body had improved, becoming sexier than it already was, often causing Lilly to have masturbatory fantasies as she lay in bed alone late at night. She even saw pieces of pubic hair in the bathroom, on the floor around the toilet or trash can. She guessed he was grooming himself and must've missed the picking up a few hairs.

The tears welling up again, Lilly asked, "What do I do?"

"You find a man, take him to bed, and sleep with him. Judd will smell his cologne, he will notice it, he will figure things out and he will come crawling back to you. Men like him disgust me," Darla said, causing her daughter to wince at her harsh words.

"They marry someone, but have a whole stable of women on the side. The second their lonely wife at home catches on and sleeps around, he feels threatened; he doesn't want to lose that little wife and his house and his toys in a divorce. So he will change. Just like your father," Darla said, speaking from personal experience.

Lilly sat at the kitchen table, rubbing her throbbing temples, "I just don't know," said through the tears.

"Look for opportunities. Call your cousin, Marie, she's been sleeping around on her husband since they've been together," Darla explained, pouring herself more coffee in the kitchen behind Lilly.

A million thoughts were running through Lilly's head. She questioned her logic for going to her mother for help. However, she had no friends, no social life, no one to turn to. She didn't want to go talk to a psychiatrist or a counselor about her problems, so she gave in and talked to the one person she promised her sister she wouldn't. Lilly then thought about her twin, Jessica, having fled Florida shortly after turning 18, and now living in Los Angeles. They hadn't spoken in quite some time; Lilly didn't want to burden Jessica with her troubles.

The thought of sex with another man made Lilly cry even more. She was incredibly shy and introverted. She assumed meeting someone on her own would be near impossible.

"I'll call Marie and tell her to call you, since I know you probably don't have the courage to do it yourself," Darla rolled her eyes from the kitchen. "You two can go shopping, hang out, Marie can set you up with one of her friends. I'll do all the work for you, this time."

"If that idiot husband of yours doesn't catch on that you, too, are sleeping around, then you are on your own. It'll serve you right for marrying a scumbag like him," Darla said setting her coffee on the table.

"Do you understand?" Darla asked a smug grin on her face.

Lilly nodded once more, sighing to herself. "Good, now leave, I'm expecting company."

Lilly did as she was told and headed home. A few minutes later she arrived, heading straight to her bedroom, closing the door and cried while sitting on the bed. She composed herself and finally let her mother's advice sink in. "Maybe it would work, like it did with dad," She thought.

Getting up, standing in front of bathroom mirror, she noticed her red roots were showing. She decided to put on a fresh coat of black dye if she and Marie did go out. Lilly shook her head, looking at her face, unhappy with her pale, white skin. She smiled, observing her corrected snaggletooth grin. Her overbite wasn't as severe as it was in her teen years, her husband complimenting her pearly white smile, slightly prominent incisors, and "pretty little mouth" as he called it early on in their relationship. Now, Lilly couldn't remember the last time Judd complimented her.

Lilly studied her mouth, it was slightly small, but had nice full lips. She remembered to her teen years, sucking Judd's cock, listening to him smugly urging her to "suck that horse dick." Her mouth hurt afterward, but she loved every second, and inch of it.

Judd was who she lost her virginity to. They started dating in high school. Lilly would watch him play football from the bleachers, thinking how lucky she was to have him, not the cheerleaders. She recalled Judd telling her long ago that when she first started showing up to his games in 10th grade to watch him, he wondered if he ever have sex with her. By the time she was 17, Lilly was pregnant with their only child, Jake.

Lilly stared into her light green eyes in the mirror, smiling slightly, pleased that her face still looked fairly young - hardly any wrinkles, and somewhat child-like in appearance. She still got regularly carded at the grocery store when buying wine. She was even mistaken as a college student at the nearby library during one of her book hunting sessions a few months ago. That smile quickly faded when she thought of Judd again.

She asked why she married him. She wondered if it was because of his big, "horse dick" as he called it. Lilly thought of his personality. Judd was arrogant, cocky, a go-getter, and a power hungry leader. He was the total opposite of Lilly. She was quiet, reserved, meek, and a follower, not a leader. She felt safe with him, like he was in control, like he was taking care of her. She stayed with him. She followed Judd to the same college, sleeping with him, all along the way, and then marrying him shortly after graduation.

His parents happily help raise their son, Jake, while Lilly and Judd finished school. Judd went onto law school; Lilly raised Jake, working part time jobs here and there while Judd's parents continued to chip in. It didn't take Judd long to rise in ranks at a business law firm in Miami, moving his family into a upscale neighborhood, paying for Lilly to get her tubes tied, paying for some corrective dental work, and paying for the luxurious life they now live.

Lilly shook her head once more. It was time for her to inspect her body. Undressing herself, standing nude in front of her bathroom mirror, she looked over her pale body. She was a lean 5'8" hourglass. She wasn't too curvy, somewhat petite, and had round, perky, medium sized breasts with small nipples. She combed her fingers through her dyed black hair, letting her locks fall over her breasts, before pushing the hair back over her shoulder.

Turning to the side, she observed her butt and thighs. They weren't too muscular or toned; however, she was proud of her bubble butt.

"Why couldn't I just offer sex more often?" She asked herself, putting her clothing back on. She knew the answer - she didn't want to bother Judd, she didn't want to disturb him in case he was too busy or had too much on his mind. Lilly wanted him to make the first moves so she would know without doubt that he wanted sex.

Later that night, before she slept, Lilly thought of Judd and her nine years ago on the beach one night celebrating their five year anniversary.

"Shh, shh, you have to be quiet baby," Judd said, rolling on top of her in the sand, as the moonlight shone down on them.

Going to his knees, he pulled her up, standing and walking to the water. Lilly moaned as quietly as she could, running her hands over Judd's massive biceps and shoulders, while he bounced her in the water. He had convinced her to come to this secluded beach that night. She was nervous about getting caught, but trusted his leadership, and submitted to him.

"Wh-wh-what about sharks?" Lilly managed to ask in between breathes.

"I'll just scare it off with my horse dick, baby," Judd joked.

"Ahh! Yes!" she cried out in the humid summer night.

Lilly shook the memory from her head, crying herself to sleep.

Chapter 2

Lilly spent more time with her cousin, Marie, the following week than she had in years. Marie took her shopping, buying her sexy short dresses, new makeup products, and shoes. The tall, big breasted blonde, knew exactly what to buy and look for.

Lilly didn't feel sexy, but Marie assured her she was. "Wow, I do great work," Marie smiled, putting the final touches on Lilly's eye makeup. Bright red lipstick, smoky styled eye shadow, and her hair combed out long and parted in the middle was quite a departure from Lilly's usual more homey appearance.

"We're going to have a great night," Marie said, hopping into her car. Marie's Aunt Darla had informed her of Lilly's situation. Marie was happy to help her cousin.

"We're meeting two friends tonight. They are brothers. I'll be Ronnie's date and you'll be Rodney's," Marie explained while driving.

"Mmm, he is going to love you!" She said, patting Lilly's bare thigh, her short hot pink dress riding up.

"I can't believe I'm going through with this," Lilly thought to herself, looking out the passenger side window. She hardly saw Judd in the past week, when she did, there was hardly any words exchanged. She wanted him to rip her clothes off and take her, but he showed zero interest in even interacting with her. Most nights were spent crying herself to sleep, after Judd got home late. All this led her to believe her deranged mother's deranged plan might actually have some merit, and might actually get Judd to take more notice.

***

Rodney slammed into Lilly from behind, his hand pinning her down by her neck, the other gripping her waist. She cried out from pleasure and pain - but mostly pain.

"Ahh!" She cried out once more, her hands gripping her bed sheets, her knuckles turning white. He was huge, he was forceful, he was a pure brute.

One more powerful thrust into her, and he groaned, leaving her cervix in pain. Lilly couldn't believe she was going through with it, but Rodney's scent filled her bedroom.

Another hour passed and Rodney was dripping sweat on to Lilly's back, holding her by her wrists, repeatedly slamming into her, shaking the bed violently. Lilly's eyes rolled into the back of her head, her dangling breasts jiggling from each hard impact. "Please work, please work, please notice this," she said to herself, feeling her body tense up, wishing with all her might Rodney was Judd.

The large brute groaned again, sliding his cock out, stroking it a few times and spraying semen all over Lilly's back. He was done, finally.

"See you later," Rodney, said gathering his clothes, finding his keys.

Lilly lay there, catching her breath, semen drying on her back. She was so close to cumming, thinking about Judd, and this plan, but was never able to achieve it.

A little later she slid out of bed, wiped the cum off her back with some of her dirty clothes, and got back into bed, still nude. She was wide awake, in the dark bedroom, when Judd finally arrived home, saying nothing, not noticing she was naked.

***

Rodney was there every other day for the next month. He'd leave the gym and go to Lilly's, banging her up against the shower wall. He'd come over sometimes after midnight, when Judd was home, Lilly meeting him outside, bouncing up and down on him in his car, hoping her husband would hear or see it. Nothing worked.

Lilly found herself enjoying it, feeling better about things, thinking that maybe if Judd is sleeping around, she was too, and they were now even.

Rodney left over gym shorts, boxer shorts, Lilly slept nude usually, not bothering to wash the semen off her face or back - but nothing worked. There was no change to Judd's behavior at all.

Lilly found herself at her mother's once more. "You know deep down you are a whore. Start acting like it!" Darla scolded her again.

"I'm not a whore!" Lilly cried.

"Oh don't give me that. Yes you are. You just haven't realized it yet. Get out there and sleep with someone close to Judd, like a client, or business partner. He will surely catch on," Darla explained, taking a sip of wine.

Lilly started crying, she had no idea who to go after. She knew none of Judd's business contacts. Luckily for her, opportunity presented itself.

Chapter 3

There were rare occasions, maybe once a year, where Judd would invite Lilly to an event with him. Usually one of his clients was opening a new office building, a new business, or had recently closed on some property and so on. Judd was one of the lawyers that oversaw some of these business transactions. He was invited to grand openings from time to time. Lilly, now distrusting Judd assumed he only invited her to make himself appear like a nice, family oriented man to a particular client.

Lilly picked out one of the sexy dresses Marie bought her, not receiving a single compliment from Judd, and went with him.

Adjusting her dress in the bathroom mirror at the hotel where the dinner and party event was held, her lips curled into a small smile, "I'm going to find someone closer to Judd tonight. I'll take him to bed."

What little confidence she gained was lost when she re-entered the convention hall, seeing its attendants having doubled in size, her introversion kicked in. This was going to be a challenge for Lilly to strike up a conversion with someone, much less a stranger, in hopes it leads to sex.

She watched the extroverted Judd, chat and laugh with Don. He lived in the same neighborhood and was a partner at the law firm. Lilly thought about talking to him, but was too nervous. Looking around the room she saw three people she knew.

She saw Wayne and Denise, the couple that lived next door, and she saw Ronnie. She was surprised to see him there, not sure how he was connected to this event. She cleared her throat and tapped that large black man's arm from behind.

"Oh hey! Lilly right?" Ronnie said. Lilly smiled and nodded politely.

"How are you?" he asked.

"I'm good. You? How are you associated with this?" Lilly asked.

"Great!" Ronnie replied, far more friendlier and upbeat than his younger brother, Rodney. "Oh well, I do some marketing and sales for the owner of the company that bought this property and developed the shopping center. So I got invited to the event too. You?"

"My, uh," Lilly paused, thinking she didn't want Ronnie to know she was married, but figured it didn't matter, "husband is part of the law firm that did the due diligence. Stuff like that," Lilly answered.

"Oh great, great," Ronnie said, glancing at Lilly's cleavage. "Would you like some punch?"

Lilly glanced over to Judd, seeing him laughing, still talking to one of his partners. "Sure," she smiled.

Lilly felt awkward in the midst of the crowded convention room. Everyone was talking, interacting with others, and she simply stood there, waiting for the punch that was taking a long time to arrive. She looked over at the table and saw Ronnie talking and laughing with Denise - her neighbor.

Lilly had always been slightly envious of Denise. She was a gorgeous brunette with a curvy figure, large breasts and long, thick hair. Her personality was something to be admired too. Outgoing, personable, funny, charming, extroverted, everything Lilly was not. Denise hardly wore makeup, she didn't have to, a little eye shadow was it. Lilly, following Marie's makeup tutelage, felt hers was caked on. Denise was also very nice to Lilly's son, Jake, maybe even a little too nice. Lilly often found Jake standing by the fence that separated their back yards, talking and laughing with Denise. Sometimes he'd go swimming over there. Lilly assumed Jake, who was a couple years younger that Denise's son was simply filling a void for her.

Several minutes passed, no punch, no Ronnie. She looked over at where she last saw him, he was gone. Lilly left the large room, disappointed, feeling silly, wanting some fresh air for a few minutes. Heading down the hallway, the loud noise of the crowd getting quieter and quieter as she made her way toward an exit, Lilly heard a new sound.

It was coming from storage closest. Lilly put her ear against it, listening to moans, grunts, and slaps. She gasped, and slowly cracked the door of the closet to peek inside. Her eyes widened when she saw Denise, completely naked, squatting up and down on Ronnie's cock, her hands propping herself up just below his chest. His hands were behind his head, he was smiling watching Denise bounce up and down on him, her mouth open, her face contorted with pleasure.

Lilly quietly closed the crack door and quickly made her way back to the large banquet hall. She immediately went up to Wayne, Denise's husband, and said hello.

***

Wayne smiled, gently laying Lilly onto her back in his bed, "I've been wanting you since I moved into this bitch's house," he said, referring to his wife. He kissed her mouth, then licked along her neck, down to her breasts.

"I'm going to enjoy this," said the smug looking, late 40s, bloodsucking lawyer. After Lilly said hello, an hour later they were back at Wayne's house, at his insistence, naked, and in bed. Lilly wanted it to happen in her bed, but figured this was fine, since it was right next door to her home.

"What about Denise?" Lilly asked.

"I texted her, letting her know I didn't feel well and was heading home. I'm sure she'll get a ride from someone," Wayne said, pinning Lilly's hands down. Reaching over to the other side of his bed, he found his belt.

"Ready?" Wayne asked. Lilly gulped and nodded her head. Wayne tied her wrists to one of the headboard rail.

It went on for hours, well after midnight. He dominated her, slapped her, ate her, and fucked her royally. Lilly thought if only it were Judd doing this, how amazing it'd be. But it wasn't Judd, it was some jerk he worked with next door that she hoped Judd would come looking for her and find her there. In some distorted, psychotic way, Lilly thought getting caught would bring her and Judd closer together.

She was sore when she left. Lilly limped out of Wayne's front door, seeing a strange car parked in his driveway. The car was shaking and rocking back and forth. Lilly heard the muffled cries of a woman climaxing. She assumed it was Denise and Ronnie but wasn't sure. She headed home, showered, climbed into an empty bed. She started crying once more. 30 minutes later, Judd finally showed up.

Chapter 4

"Ahh!" Lilly cried out in pain. She was on fours on Wayne's bed, tied up, being spanked with a belt. Her butt and back had large, red, whelps on it.

"Take it! Whore!" Wayne shouted, whipping her again.

"I'm not a whore," Lilly thought. Her affair with Wayne had been going on for month. It was early March. Wayne whipped her again. She was used to it. She had been tied, gagged, slapped, sodomized, urinated on - Wayne was disgusting.

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