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  • Former Playmates Pt. 03: Diane and Son

Former Playmates Pt. 03: Diane and Son

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Author's note: This is part of series involving fictional former Playboy Playmates. They are all sisters and will each have two stories -- the first one will be interracial, the second will be incest.

Diane is introduced in my other story: The Challenge 4. It's not necessary to read that story but you may think it's neat to learn a few things about her from it. Her first story (part 2) in this series is a short interracial one where she has some naughty fun.

The events of this story take place a couple months after part 2 in this series. This story also takes place the year before The Challenge series of stories. As a warning, there is quite a bit of dramatic irony in this one. The reader will know things some of the characters do not.

Finally, this story takes place right before Rachael's Year begins. To learn more of Ronnie's exploits feel free to read her interracial story next.

Editing thanks go to Todger65.

*

Chapter 1

Elliot rolled his eyes, listening to his older sister Valerie, drone on and on about their mother. She was begging Elliot to spend more time with Diane, complaining about the man, Ronnie, she was seeing, explaining how she didn't like her mother's dating situation.

"Please? Look, the only reason she's seeing Ronnie is because he's younger and it makes her feel younger. But he's just using her, for uh, well - " Valerie paused.

"It's not my problem. It's her life, she can date who she wants. She always has," Elliot sighed, not wanting to hear so much personal information about his mother's sex life. He recounted several instances where he knew his mother was unfaithful to her now, ex-husband - Elliot's stepfather. She would go out on dates, attended events, and go out of town on short trips. During Elliot's 20s he was able to put two and two together. Now at 30 he shrugged off his mother, Diane's, dating life, realizing that she can do what she wants and if she was as unfaithful as he suspected, he turned out just fine.

"I just don't like this guy. He's smug, he's arrogant, he tries to be funny, he's -- " Valerie was interrupted by an annoyed Elliot.

"You just don't like the dude because he's black," He suggested, not totally sure if that was the case.

"No! I don't care about that," Valerie replied. "I just think he's bad news. It doesn't matter what his skin color is."

"Whatever," Elliot said. He checked the time on his phone. He had to pick up his wife, Cassie, from the nursing home she was a nurse at. Her car was in the shop getting repair work done.

"I have to go soon. I don't know what you want me to do. I can take her to dinner I guess," Elliot rolled his eyes.

Sensing that Elliot was becoming increasingly annoyed, Valerie decided to play another card, "Look she's been talking about you a lot the past few months. She wouldn't want me to say this, but she really wants to be closer to you."

"What do you mean?" Elliot asked. His mother had been acting different around him. She would call him more often, she would invite him over for dinner more, she would text him, send him cute emails and since she apparently confided in his sister that she wanted to have a closer relationship with him -- it made sense now.

"Yeah. She has mentioned to me several times about how you and her weren't super close and she wants to change that, so you need to go over to her house and spend more time with her. I want her to forget about this sleaze ball she's seeing!"

"Why would she dump some guy just because her son is around more often?" Elliot asked.

"Well they aren't boyfriend/girlfriend, so there would be no dumping. Trust me, if you spend more time with her, like taking her to the beach, or to dinner or whatever -- based on how she's talked about you, she'll forget all about Ronnie," Valerie explained.

"I don't know," Elliot trailed off. There was something else about his mother that made him feel uncomfortable. The silly texts, emails, and phone calls were fine, but when they did see each other every once in awhile, Diane seemed different. She was more affectionate, giving longer, stronger hugs, lingering kisses on the cheek, occasional pecks on the lips. It wasn't horrible, by any means, just not something Elliot was used to.

Stopping by her home a few weeks ago, Elliot was visibly uncomfortable sitting next to Diane on the couch. When Cassie was in the bathroom, Diane would chat with him about his weekend, rubbing his thigh slowly, almost seductively, abruptly stopping with Cassie entered the living room from the hallway. Little things like that caused him to feel weird. It didn't help matters that his mother, a 52 year old, blonde bombshell and former playboy playmate, still looked incredible. Yes she dyed her hair, constantly watched what she ate, exercised almost daily, but still looked amazing with only slight wrinkles around her mouth, eyes, and forehead. Elliot couldn't deny, if asked, that she was a beautiful older woman.

When he and his wife left her house that day to head home, Diane slapped Elliot's butt as he walking out her front door, causing him to smile awkwardly back at her beaming face. Getting into his car, he waved at her, glancing briefly at her huge breasts when he drove by, noticing the large amount of cleavage on display from her pink pajama tank top.

Shaking the memory from his head, Elliot drifted back to the present, where his sister was still going on and on about Ronnie. He hadn't been paying attention and when he tuned back into the conversation he immediately felt uncomfortable again.

"Her house was a mess. A total mess. Her bedroom was in shambles. There's no telling how long and hard her and Ronnie were going at it and I -- " Valerie was saying.

"Ok! Ok! I get the picture. Too much info!" Elliot said; he'd had enough of this. "Alright, I'll stop by and see her and we'll figure this out, ok? Satisfied?"

"Yes, I think this'll be great. For both of you," Valerie answered.

"I'll stop by later tonight. Cassie will no doubt go to bed early, so instead of being bored, I'll just go over there I suppose," Elliot told Valerie.

"Good! Spend a nice Friday evening with her. Maybe check in first to make sure she cancels any plans she may have with Ronnie, alright?" Valerie suggested.

"Ok I will," Elliot said. They ended their phone call, Elliot grabbed his keys and left to pick up Cassie from her work. She yawned on the way home, tired as usual, quiet as usual.

Elliot rolled his eyes at Cassie. He had been working out more, eating healthier, losing 20 pound and slimming down a bit. It seemed to have no effect on his wife. He doubted she even noticed. He recounted the last six years with her. She was never a sex fiend, but he wasn't either. She never gave many compliments early on in their relationship, other than that she liked his blue eyes and dirty blonde short hair. He almost started exploring questions about why they married when she coughed a few times shaking him from his trance.

At a stop light he remembered he needed to check with his mother before heading over there. He took out his phone and texted her a quick message to ask if she wanted to hang out that night.

********

"Yeah! Get that dick!" Ronnie yelled, slapping one of Diane's tits as she squatted up and down on his cock in her bed.

"Ah!" She cried out, another orgasm building up. She was nearing exhaustion. "Oh fuck!" she yelled, collapsing on the hugely, muscular Ronnie, shaking in pleasure.

"Mmmm, yeah," he moaned, pushing her off him, grabbing a tit to suckle. Diane smiled, looking down at him when her phone next to her bed jingled the tone she assigned to Elliot. Her eyes shot open, reaching to grab it, to read his text. Ronnie continued sucking away on her left breast, while texted her son back, in all caps, "YES!"

Putting her phone back on her bedside table, she looked to Ronnie, "You're going to have to leave soon I'm afraid."

"What? You can't take care of your big Ronnie tonight?" He asked.

"Sorry, not tonight! I have another man coming over," Diane smiled.

"How many men are you shacking up with?" Ronnie asked.

"Well, just you, this is my son that's coming over and sorry, but he's far more important than this," Diane said, sliding off Ronnie, squeezing his still erect rod with her hand.

"Aww," Ronnie playfully sulked.

"When my baby boy wants to spend time with his momma, I'm going to be available for him," She explained wiping sweat off her face with a t-shirt from the floor.

"Now off you go! I have to clean up our mess, I need to shower, and start some dinner," Diane said. Ronnie nodded, gathered his things and said goodbye.

In the shower Diane couldn't help but smile in anticipation for Elliot's arrival.

Chapter 2

"Mmmmwuah!" Diane said, giving Elliot a long kiss on the cheek when she sat next to him on the couch, curling into his side, grabbing and swinging his arm around her.

Elliot smiled softly. She had been like this all evening, affectionate and sweet. They watched a movie after dinner, her hand holding his, bringing it to rest on her hip, her head against his shoulder.

Elliot couldn't help but be somewhat amused by his mother's reaction when he suggested they hang out more often during dinner. She practically screamed "yes" in agreement. Diane went on to suggest dinner at some of the new restaurants, shopping for both of them, and he could accompany her to Atlanta should she decide to visit. Elliot simply nodded and politely agreed.

"Maybe tomorrow we could head down to the beach," Elliot said after a few minutes of cuddling on the couch, thinking to his sister's suggestion.

"Yes! I'd love that! I have a new bikini I haven't worn yet," Diane kissed his cheek once more, snuggling in close to him.

"Oh crap," He thought. "What if she starts acting flirty at the beach? I bet her bikini is pretty revealing. She has been acting strange lately, like she's trying to be younger."

The pleasant evening ended with a peck on the lips and a sweet smile. Elliot drove home feeling slightly nervous about the following day. He saw Cassie asleep in the bed when arrived. He tried not to feel anger toward her, realizing that she was on her feet most of the day at a demanding job. Still, he wished she had more energy or try to change shifts, hoping it could improve their sparse sex life.

Lying in bed wide awake, he thought about broaching the subject with Cassie, but decided not to. He worked eight hours a day, where she was usually there for 12. Elliot couldn't help but empathize with her. He rolled over, listening to her snore lightly, wishing that he could be having sex right now, and wishing she was awake for him.

His phone next to the bed vibrated, indicating he had a text message. Picking up the phone, he saw it was his mother saying she was awake, but was heading to bed soon, and that she had a wonderful night with him. He replied, saying he'll pick her up at noon for the beach tomorrow. "She's still awake," He thought, looking over his shoulder at his sleeping wife, "maybe spending more time with her will be good for me."

********

Elliot was right; the bikini was like something a 20 year old would wear. It was fairly small, pink with white strips, and he had to admit she looked great in it. He watched his mother saunter into the water, the small waves crashing against her toned thighs, looking away when she playfully bounced to avoid water splashing onto her face. He felt uncomfortable once more, seeing her sizable breasts bounce with her.

When she straddled him in the deeper water Elliot was standing in, her legs locking tightly around his waist, he felt even more uncomfortable.

"Hi," she smiled, kissing his cheek. "This was a great idea," Diane said, resting her arms around his shoulders.

"Yeah, it's nice out," He said, looking away from face.

"Hey. You don't think I look too old to be wearing this do you?" Diane asked.

"What? No, not at all," Elliot replied, glancing at her face briefly.

"Good. I feel old sometimes. Old and ugly," Diane said.

"Huh? No, that's silly. You look great mom," Elliot said.

"You think so?"

"Of course! You look really good," Elliot smiled.

"Thank you," Diane kissed his lips briefly again, causing Elliott to blush and look away.

"Gosh, I think this top is too small," Diane said. When Elliot looked to her, she was adjusting her top, moving her massive breasts from side to side, inches away from his chest. "My boobs are too big!"

"Heh, yeah," Elliot gulped looking away.

Satisfied with her adjustment of her top, Diane spoke up, "So are we going on another date tonight?"

"A date?" Elliot asked.

"Yes! I had a great time last night. Maybe we can go to dinner tonight. Unless of course, Cassie has plans for you," Diane said, running her fingers through Elliot's hair as he stood in the deeper water.

"No, she doesn't have plans," he shrugged.

"Good, then you and me will go to dinner. It'll be someplace nice. I think I have a dress that can contain these!" Diane said, grabbing her own breasts, squeezing them playfully, eliciting another blush from Elliot.

"Unless of course, you like big boobs," Diane winked.

"I, um, well, I -- " Elliot stammered.

"Ha! You do like big ones don't you!" Diane laughed. "Well good, because all my dresses are pretty revealing."

"Yeah," He sighed, looking to his side again, watching the water gently crash into the shore. He thought back to his younger days, recalling all the various dresses he'd seen her wear when she went out with who knows who.

"I love you. You know that right?" Diane asked, shaking Elliot out of his trance.

"Hmm? Yeah, I know. I love you too, mom," He smiled softly.

"Good. I'm really hoping you and I can be closer. Certain things have taken place in my life recently and it made realize I want to spend more time with you. I feel regret for us not being as close in your younger years. Anyway, I 'm just really happy we're spending more time together."

Elliot nodded, "Yeah, it's nice." He glanced down to her cleavage then back to her smiling face. They shared a brief gaze into each other's eyes, broken only by Elliot's blushing. He glanced once more at her cleavage, then away to his side.

"Yep, you like big ones," Diane whispered into his ear, pressing her breasts against his bare chest.

Elliot chuckled, "Ok well let's head back, I think a shark swam past my leg," he joked, trying to break the tension he couldn't help but notice. They held hands, walking back to their spot on the beach.

Back at his mother's house a few miles away, they discussed their evening plans, before Elliot left. He'd be back in a few hours to pick her up for dinner. His heart raced once more when Diane turned around, her back toward him, removed her bikini top and headed back to her bedroom to shower. He could see the sides of her large breasts from behind.

"Whoa," He thought on the way home. "This has got to be some sort of phase or something. She really seemed flirtatious and sexual today. Weird."

As soon as he arrived home, Cassie handed him a list of things to do. He had a few hours, but he figured he could get them done and shower in time to pick up his mother. He told Cassie of his plans and she didn't seem to have an issue with it. Elliot figured she'd be asleep by 9pm anyway. He watched her petite, small frame walk away from him down the hallway, leaving him with his list of chores, mainly moving furniture, taking stuff to the dump, and so on. The image of his mother's nearly nude body walking away from him, with her hourglass figure and large breasts visible from behind popped into his head in the place of Cassie. He cleared his throat and shook the image from his head, going about his chores.

Chapter 3

At dinner Elliot was a nervous wreck. He clumsily complemented his mother on her dress, a tight, dark red number, with breasts nearly spilling out of it. He gulped and eked out a "hair too" nervously glancing away. Her shoulder length blonde locks looked professionally styled. He felt embarrassed that he wasn't wearing a suit, looking to his shoes past his khaki pants and tucked in shirt.

Diane hugged her son, kissing his check, wiping away lipstick. "I'm glad to be having dinner with such a nice looking man."

Elliot couldn't believe he felt this way, this nervousness, and this awkwardness around her. He couldn't explain it. Yes she was attractive, yes she was acting differently around him, but the butterflies in his stomach couldn't yet be explained. As they chatted at dinner, he felt even more foolish when she started playing footsy with him.

"I'm a grown man, why is this affecting me so much?" He asked himself.

When his mother reached across the table, placing her hand on his and began to speak, he found his heart rate slowing a bit. "I wasn't always the best mother. I was out a lot, your step father and I had problems, but things are better now. The past few months I've been hoping you and I would become closer. We're both adults now, so I figured we could enjoy each other's company more often."

"Yes," Elliot agreed. "I'd like that."

"Good. I want you to come to Las Vegas with me in a few weeks. There's a Playboy reunion of sorts, for the girls that posed within a five year period that I did, and I'd love to go," Diane said.

"Um, well I have work, and -- " Elliot answered.

"I know, it's during Labor Day weekend. That's over a month away. Do you think you could ask off for a week and come out there with me? I'd really love it," Diane said, smiling sweetly at Elliot, her hand caressing his.

"Well, I suppose, I could ask off of work. That's not too short of notice for a week off request," He said.

"Great! We'll go out there for a week. We'll have so much fun! I can tell all the ladies that you are my boyfriend!" Diane laughed.

Elliot's mouth dropped causing more laughter. "It's ok! None of them know you, and plus, I'll feel young and sexy to have such a nice looking younger man there with me."

"Heh, yeah, I guess," Elliot chuckled. They once again shared a brief gaze to one another, before Elliot glanced at her generous cleavage, and then to his nearly finished meal.

"Your Aunt Stephanie may attend too. She mentioned that she'd like to go. I haven't seen her since before she moved back to Minnesota," Diane added, while sipping some wine. "She posed a few years after I did. I know you always had a crush on her."

"Mom, I -- " Elliot tried to say. He did have a crush on her in his younger years; he had a crush on all his Aunts.

"You probably had a crush on all your Aunts," Diane said, knowing him too well. "I know you wanted Alyssa to be your girlfriend when you were a kid," Diane laughed, referring to her youngest sister who was 7 years older than Elliot.

"Mom please," Elliot pleaded, blushing again.

"She had a pair of boobs. Big, round, areolas," Diane said.

Elliot shook his head, mortified.

"I miss her. I hope she's well, wherever she is," Diane said. She hadn't seen her youngest sister in several years.

They concluded their meal without too much more embarrassment.

********

She insisted he come inside when he took her home. Pouring a glass of wine, sitting next to him on the couch, Diane put her arm around her son, smiling warmly as she sipped from her glass.

"So your wife doesn't mind that you're out with another woman tonight?" She jokingly asked.

"Nah, she's probably asleep by now. She doesn't mind or care," Elliot pointed out.

"Awww. How is your sex life with her?" Diane asked.

"Mom!" Elliot cried.

"What? I'm just curious if that girl is properly taking care of her man," Diane said.

Elliot sighed, "It's, well, it could be better." He took another sip of his wine.

"That's a pity," Diane said, leaning over to kiss his cheek, "she should be making love to you every night. I would." Diane stroked her index finger across his chin, "If I were your wife I mean," she added, sensing that she may have made him feel even more uncomfortable than he already did.

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