Mom and son take a wild trip to Las Vegas. Plans, ulterior motives.
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.
Former Playmates Pt. 03: Diane and Son
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 big black 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.
“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.
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.
Elliot nodded and smiled, sipping occasionally from his glass.
“Did you know,” Diane said, placing her empty glass on the coffee table, “I used to be a stripper?”
“Sandee mentioned something about it a long time ago,” Elliott replied, referring to his older sister, who left home at 18 to be a stripper in Los Angeles.
“I kept it a secret as best I could. But I really loved doing it. I met a wonderful older man who I became great friends with. I figured we could visit him on our way to Las Vegas. He’s in Atlanta, so we’ll drive there and stay a night or two there before we fly out. Is that ok?”
“Yeah that’d be ok.”
“We can visit your Aunt Tiffanie while we’re there too. Though to be honest, my friend, Bob, will probably want to take me out. Like I said we’re great friends,” Diane explained.
“I see, well then that’s fine,” Elliot downed the rest of his wine. “I can hang out with Tiffanie. She has big – ” Elliot stopped himself.
“Boobs like me?” Diane asked, assuming that’s what he was going to say. Elliot chuckled and nodded his head.
“It’s settled then. I’m looking forward to this!” Diane hugged Elliot pressing herself hard into him. Afterward she rested her hand on his thigh, just like she did that one night earlier in the summer. “You know what happens in Vegas, stays in Vegas,” She winked at him, standing to head to the kitchen.
Elliot’s heart rate increased again. Glancing over his shoulder, watching his mother in her tight red dress, stand on her tip toes in the kitchen; reaching to put the wine away in a top cabinet, he noticed her shapely backside too.
“What is going on here?” He asked himself. Suddenly his mother turned to face him, still in her tip toe position.
“You going to help me or keep checking me out?” She asked with a devilish smile.
Elliot gasped, “I, uh, I was just. Yeah, let me help.” Diane slapped his butt playfully when he put the wine back where it belonged.
“Ok, boyfriend, tell your wife I said hello,” Diane joked, hugging Elliot good night. He nodded, only to be met by a kiss on the lips. “Goodnight.”
When he got home he took a cold shower, feeling idiotic, and shame for checking her out. He decided to call Valerie in the morning and relay a bit of what’s been happening, careful to leave out certain parts that he felt might make him look creepy.
Elliot listened to Cassie sleeping next to him. His cell phone buzzed alerting him to a text. It was his mother saying she enjoyed the evening with him and would see him again soon - he smiled and texted her back, saying goodnight. A few moments later she did the same, adding an “I love you.”
Back at Diane’s house, she sat on her bed naked, talking on her cell phone. “Yes it was great. I think, I think it’ll work out. I’ll actually be able to go through with it. Yes, yes, I know I’ve sort of done something similar, but it was different with you. He will, it’ll take a little time. But I think once it does happen, oh wow.”
Stepping out into her moonlit backyard, still naked, she sat in a lounge chair still talking on her phone, ”Mmhmm, next year? I think those houses will be done by then, yes. I can’t wait to move into my new one. That neighborhood isn’t far from here. Yes. I’m sure he’ll come with me!”
Diane ended the call a few moments later with a smile on her face. She trailed her hands over her large breasts, gently tweaking a nipple. Her phone buzzed alerting her to a text. It was Ronnie.
“Hey baby, want some of this big dick tonight?” the text read. Diane chuckled, sitting her phone down, not bothering to answer.
“Yes, I want some big dick, Ronnie,” she said out loud, “but not yours.”
A collection of several dildos lay before Valerie on her bed. They started small in size, working their way up to a gargantuan toy. The nude Valerie stood at her bed, deciding to start small and work her way up. This would be her second workout for the day. The first one was at the gym that morning, which left her butt and thighs sore and wobbly.
Her phone rang, “Hey, what is it? I’m in the middle of something,” Valerie told her younger brother.
“Hey Val, listen this thing with mom is a little weird. We’ve hung out more, but, she’s just, I don’t know. Is she ok?” Elliot asked.
“What do you mean is she ok? Yes, she’s fine,” Valerie barked at him.
“She just seems different, like she’s trying to be younger. Plus we’ve never been real close anyway so – ” Elliot said.
“Don’t give me that! I know she’s been acting a little odd lately, but she’s fine.”
“I know but, it’s like she flirting with me,” Elliot said.
“She’s always been flirty and somewhat sexual. She even suggested I get into stripping at one point. It’s no big deal. You’re just going to have to let it go. You and her are getting closer and you are discovering this stuff on your own. She’s fine, I promise,” Valerie assured Elliot.
“Alright, it’s just that she wants to see me again, maybe even every day,” Elliot said.
“I don’t want to hear it,” Valerie said, picking up and throwing down a large dildo after briefly inspecting it. “You are going to wake up one day after she’s long gone and wished that you and your mother were closer. She wants to be closer, so let it happen!”
“Yeah, I guess,” Elliot said.
“Good, keep it up. This is really helping her move on from that guy she was seeing,” Valerie replied.
“Alright, I’ll let you go then. Talk to you later,” Elliot ended their call.
The tall, dirty blonde, Valerie tossed her phone on the mattress, “I think I’ll start with you!” She grabbed a decent sized dildo which could be mounted on the wall and headed to the shower.
Elliot followed Valerie’s advice. He and his mother spent more time together in the next month than he recalled they ever had. He saw less and less of his wife. Cassie didn’t seem to notice. The only mention of her was when Diane asked how she was doing or she had a problem with her husband spending so much time with his mother.
“Are you sure she doesn’t mind?” Diane asked, later in August. She was wearing her pajamas and Elliot was over at her house to take her out to breakfast, followed by another trip to the beach. She was straddling him on the couch.
“Yeah she doesn’t mind.”
“She might though. You should double check. She may have a problem with you hanging out with a woman with these!” Diane quickly threw her tank top off, revealing her large, bra-covered breasts to Elliot.
Elliot looked away, “Wow, um, well I think she knows you have those.”
Diane laughed, getting off her son, heading toward the hallway to change into her clothes for breakfast. Her flirtatious ways hadn’t changed. The kisses and affection had increased though. Later that day she was peppering his face with kisses while she straddled him in the water at the beach. She ended the encounter with a long kiss on the mouth, taking Elliot off guard, and drawing the looks from a couple of nearby girls.
“Yes this is my boyfriend,” Diane jokingly glared at the girls, embarrassing Elliot in the process.
“Have you and Cassie come out here much? It’s a nice place to visit at night, no one is around, if you know what I mean,” Diane whispered in his ear.
“No, we haven’t been out here. She’s not a fan of hot weather and sand,” Elliot said.
“Sounds like she’s pretty boring. Sorry,” Diane noted.
“She is,” Elliot said flatly. He silently blamed her job, but deep down he felt that was no longer a valid excuse for her low libido and lack of interest in anything.
Later that night near midnight Elliot arrived home. To his surprise his wife was still awake. She was angry, “Why are you over there all the time? Are you really over there or somewhere else?”
“What are you trying to say? Yes I’ve been hanging out with her. No I haven’t been screwing around! Do you want her to call you to let you know I’m actually there?” Elliot asked, starting to get angry.
“No, but – ” Cassie started to say.
“But nothing! Besides it’s not like there’s anything to do here. You sleep a lot and we hardly ever have sex. I might as well hang out with a woman that loves me,” He said, immediately regretting it.
“Are you saying I don’t? I told you, I’m on my feet all day; I have to deal with those patients too. You would be tired if you had to deal with what I have to!” Cassie yelled.
“I get that, but you still can’t make a little time for me? Come on, really? Maybe YOU’RE the one screwing around and you’re too tired to do anything with me when you’re done!” Elliot said.
Cassie slapped him as hard as she could, “I would NEVER do something like that. I’m not a whore like your mother!”
Elliot froze, unable to respond as a result of the anger coursing through him. “Yeah, that’s right,” Cassie added, “I’m basing it off what you’ve told me about her! You’ve said you suspected she slept around on your stepdad. So,” She paused, tapping her chin with her index finger obnoxiously, “doesn’t that make her a whore?”
Elliot said nothing. Grabbing his wallet and keys he left the house and headed back to his mother’s. He fell asleep in her arms, his head resting on one of her giant breasts while she watched TV.
On the other side of town, Valerie collapsed onto her bed. She pulled out a large, but not the largest, dildo from her gaping pussy. She was out of breath and smiling. “Almost there,” she said, looking over to the biggest one of her collection - a monstrous dildo on her bed side table.
Elliot barely spoke to Cassie in the last week of August. He instead, stayed with his mother. He only saw Cassie when he went to collect some clothes, including enough for the Las Vegas trip that was on the horizon. Cassie apologized profusely, begging him to stay. Elliot apologized in return, but told her he just needed some time away for a bit. After this trip with his mother, he assured her they would fix things and work out any issues they had. Cassie’s car was repaired so she didn’t need to rely on him for rides.
He loved the feeling of an older, sexy, woman running her hands up and down his torso, lying in bed with him each night. Diane was in Elliot’s arms every night he was in her bed. Cassie would always sleep on the other side of the bed, never cuddling much at all.
Elliot came home to his mother from work, ate a wonderful meal, and spent the evening with Diane on the couch talking, flirting, watching TV. They would hold each other until they fell asleep. He loved it, but just assumed this was her way, this was how she showed love and affection. Elliot was fine with that.
“You going to go to a strip club with me out in Vegas?” Diane asked Elliot the night before their drive to Atlanta the next morning.
“I’m not too sure about that!” He replied.
“Alright, suit yourself. You have nothing to be embarrassed about. I have a few contacts out in that area and maybe we could stop by and see how their clubs are doing. I danced there a few times in my younger years,” Diane said, standing against Elliot in the kitchen, his arms resting at her waist.
“Maybe. You’d probably get up on stage and try to embarrass me,” He joked.
“I don’t think I’d have to do that to embarrass you,” Diane said, slowly guiding his hands from the small of her back down to her butt and holding them there with a sneaky grin on her face. Elliot was indeed embarrassed, his eyes shooting open, he tried to let go of her pajama covered ass, but his mother was holding his hands tightly there.
Finally she let go, “See what I mean?”
“Come to bed, we have an early morning start tomorrow,” Diane said, walking down the hallway to her bedroom with a smile on her face.
Elliot held her against him, smelling her hair, running his hand up and down her back. “That feels nice,” Diane said. “Does Cassie ever lay like this with you?”
“I’m sorry,” She replied. “Hey maybe, just maybe, if you really play the part of my hot, young boyfriend, I’ll do a nice dance for you. I’d show just how amazing I was.”
“No, no, you don’t have to do that,” Elliot said.
“Aw come on. Have you ever had a lap dance?” Diane asked, sliding up on top of him in straddling position, slowly gyrating her hips onto his crotch.
“No, I haven’t.”
“You think I’m too old to give one?” Diane pouted.
“No, not at all. I don’t think you’re old!”
“Good,” Diane said, slowly pulling her tank top up and off, revealing a large pink bra, while continually to gyrate her hips onto Elliot.
“Whoa, whoa, what are you doing?” Elliot asked.
“Just playing,” his mother said, tossing her tank top to the floor. She smiled, running her hands up under Elliot’s t-shirt.
Slowly grinding on him, never looking away from his eyes, Diane continued. She grabbed his hands and placed them on her waist to hold her in place. Elliot’s eyes shot open. He was hard as a rock. His cock was pointed up toward his stomach and throbbing with the warm weight of this woman’s gorgeous body on it. His mother surely knew. He thought her heard a slight sigh, a moan, come from her mouth – the only sound either of them made in this quiet intimate moment on the bed.
Diane stopped moving her hips a few minutes later, bending down to slowly kiss Elliot’s lips, “What happens in Vegas…” she whispered, jabbing him in the side when she got off him to grab her shirt and use the bathroom.
Elliot was left with a throbbing erection, scared out of his mind, scared something would indeed happen in Vegas that would be wrong and inappropriate; and scared that he wanted it to.
“Ah yes, I’m cumming, I’m cumming,” Diane whispered into her phone, outside in her moon lit backyard. She was naked again, a few hours later, Elliot was finally asleep. She had been furiously rubbing her clit while on the phone.
“Yes I thought of him,” She told the person on the other end. “Mmmm. I think it’ll happen in Vegas. I can’t rush it though. Oh I know, it will be amazing. Mmhmm, yes. I can’t wait to see you tomorrow either. I can’t wait to make love to you. It’s been a few months I think. When I was there last, right. Yes. Ok, I better go, I’m sweaty and tired now. I love you too dad. Good night!”
“Mmmm,” Diane moaned, gathering up vaginal fluid with her index and middle fingers, licking them clean, smiling at her plan coming together.
Across town, Valerie screamed out in pleasure, shaking and moaning on her bed. She pulled out the biggest, widest, dildo in her collection that she owned, tossing it aside. “I did it, I did it,” she whispered, out of breath. She had been riding it for an hour, her strong legs and butt aiding her.
“I’m ready. I can do it,” she caught her breath, smiling at her plan coming together.
There was something odd about Bob that Elliot couldn’t immediately place. He was a very wealthy, friendly, and entertaining man nearing 70. He looked much younger than that, besides a large belly. He did have white hair and a trim white beard. While he had wrinkles, he could easily pass for someone 10 years younger.
Elliot was taken aback by Bob’s friendliness. He kissed Diane on the cheek, hugging her tightly, proving to Elliot that the two must indeed go way back. He showed Elliot around his huge home and gave Elliot the keys to one of his sports cars to go pick up his Aunt Tiffanie for dinner while Bob entertained Diane.
Bob smiled when he handed Elliot a crisp $100 dollar bill as he left. There was something about his smile, something familiar that caused Elliot to do a double take. He thanked him and made his way to visit his Aunt. She was expecting him, since Diane coordinated everything.
At 39 Tiffanie looked like a younger version of Diane, except her mouth was shaped differently. She had far toothier grin. It was very cute, Elliot though. Her body, her breasts, her hair was all very similar to Diane’s. She was, however, 5’4” about 4 inches shorter than her older sister.
At dinner they talked about work, about Elliot’s somewhat boring job as an accountant, about Tiffanie’s exciting job in a marketing department of a smaller company than the large corporation she used to work for. They talked about her son, Tom, how he had just entered the 11th grade in high school, and how much he liked soccer.
Elliot caught glances at her large breasts throughout dinner, unbeknownst to her. “Yeah, I’d still spank to her I guess,” Elliot thought, a slight grin coming over his face.
“What?” Tiffanie smiled, noticing it.
“Oh nothing, I was just thinking about this Playboy event Mom is dragging me to,” Elliot lied.
“Yes, she really into all that, I suppose. I haven’t kept up with anything. I felt a little shame after I posed. I wanted to distance myself as much as possible. Now, I feel ok about it, but my late 20’s and early 30’s I wanted to get away from that image as much as I could,” Tiffanie explained.
“Did you know my Mom used to be a stripper?” Elliot asked.
“Mmhmm,” Tiffanie chuckled. “Hey if she enjoyed it and it provided some extra income to support a family, well, good for her!”
“Yeah,” Elliot smiled, sipping his tea. “Her and I weren’t all that close, we got along just fine, but we weren’t close friends. We have become friends recently and it’s taking a little getting used to.”
“I’m sure it is! She is a handful!” Tiffanie laughed, immediately causing Elliot to thinks of both his Aunt’s and mother’s giant breasts.
“But I think it’s great though. I think you could be a best friend for her and I think you could see that in her as well. So just go with it and let it happen,” Tiffanie smiled, reaching across the table to pat his hand.
After dinner they headed back to Tiffanie’s house. Elliot played a few video games, very poorly, with his younger cousin Tom. He also wasn’t used to today’s video game systems.
Tiffanie suggested Elliot linger around awhile, after he hinted his mother was with a “friend” that evening. She knew exactly what she meant, pouring him some wine. They headed out onto her back deck on the humid night.
Watching her look up to the moon, glancing at her breasts budging out of her pink tank top, Elliot spoke up, “So you seeing anyone?”
“Ha! No,” She answered, gulping her wine. “I went on a date a few years ago, it was bad. Before that was my former boss.”
“Shaking up with the boss eh? Nice.” Elliot joked.
“Well it was! Bob was a great man and employer, but I had to calm down and focus on Tom,” She said.
“Mmhmm, that was his name. He owned one of the companies I worked for. We got very close,” She said. Elliot’s jaw dropped inside his head, wondering if this was the same Bob.
“I see, well it’s good to be around for Tom more,” Elliot smiled.
Tiffanie returned the smile, “It’s good you’re around for your mom more. I think she really needs you in her life. This is great that you are going to Las Vegas with her.”
Elliot nodded, finishing his wine. The two finalized their morning plans. Diane and he would return, they would have breakfast, and Tiffanie would take them to the airport afterward.
On the way back to Bob’s Elliot wondered about this possible name coincidence.
“Come on! Come on girl!” Bob grunted as he bounced his daughter up and down. Diane was cumming again. She was slick with sweat in his master bedroom, straddling him on his huge king-size bed.
“Yes!” she cried out, throwing her head back, Bob diving into kiss and lick in between her breasts.
“Yes,” Diane moaned, her body eventually calming down, resting in Bob’s arms.
“Good girl,” Bob said, rubbing her back.
“Have you, have you seen or told Tiffanie you’re our father?” Diane asked, still panting.
“I haven’t. Not yet. If she wasn’t an employee that I slept with and just a woman I met and slept with like with you, it might be easier. Makes me a bit nervous that she would lash out at me because we worked together for a few years,” Bob said.
“One of these days she’ll know,” Diane said.
“She will, perhaps when I die,” Bob chuckled. “How are things going with your plan for Elliot?”
“Great. Like I told you on the phone, it’s going to happen in Vegas!” Diane smiled, kissing the older man once more, initiating another round of sex.
Elliot arrived back at Bob’s shortly after midnight, regretting staying so late at his Aunt’s. When he entered the home, hoping to head right to bed, he heard it – grunts, moans, and yells. He rolled his eyes, “Must be mom.”
He started to head to bed when curiosity got the best of him. He pictured enormous breasts bouncing. He wondered if he could get a peak. “A quick peak is all. I bet she looks great. Then I’ll go right to bed, because this is pretty stupid for me to do,” he thought.
As he snuck down the hallway, Elliot no longer heard as many animalistic grunts and moans; he heard talking mixed in. It caused him to pause and listen just outside the double doors leading to Bob’s bedroom.
“Yeah? Then once that house is built for you, you’ll move in?” Bob grunted, still gripping Diane’s waist as she bounced.
“Yes!” She cried out.
“You’ll get him to move in with you?”
“Yes!” she answered and cried out in pleasure at the same time, her eyes closed and her head still thrown back, facing the ceiling.
“Mmm yeah, good girl. Your sisters too?” Bob asked, slapping Diane’s ass, causing Elliot to nearly chuckle out in the hallway.
“All of you, together in that new, big house!” Bob clenched his teeth.
“Ahhh YES!” Diane screamed again, her body shaking in his grip.
“I gotta tie you up. Get off me honey,” Bob said, getting off his bed. Elliot heard his foot falls on the hardwood floor and tip toed away in case Bob opened the door and saw.
Bob grinned after retrieving two belts from his closet. “Ready? I was never around to discipline you as a girl, so we’ll have to pretend you’ve been bad.”
“Oh, believe me, dad. I have been VERY bad in my lifetime,” Diane smiled, moving to all fours, extending her hands to the one of the bed posts. She was in for a long night.
Back in Elliot’s room down the hall, his door was closed and his mother and Bob’s noises could hardly be heard. He lay wide awake in bed, thinking about what he just heard.
“A new house? My Aunts moving in? When? Where? Was Bob referring to me moving in too?” He asked himself. Sleep didn’t come easily for him. He thought about sneaking down the hall once more to get a peak, but was tired, didn’t want to get caught, and deep down thought it was stupid to spy on her like that. He figured if his mother picked on him any during this trip, he could pick on her back about her and that old man.
They said goodbye to Bob the next morning, Elliot still noticing something odd about his appearance. He handed him another $100 bill. Elliot tried to return it, but Bob would have none of it.
Breakfast was pleasant with Aunt Tiffanie. Tom joined, much to Diane’s delight. She relished in flirting with the young man, embarrassing him, and slightly embarrassing Elliot. Tiffanie shot him a knowing smile, telling him to keep an on her in Vegas when she dropped them off at the airport.
It was a nonstop flight to Las Vegas that took around four and a half hours. Diane was fairly well behaved, not flirting or attempting to embarrass her son too much. She couldn’t make it the whole flight though. As soon as the flight attendant announced they would be landing soon, she casually closed her book, took off her reading glasses, and turned to Elliot.
“I suppose we should join the mile high club before we land,” Diane said, loud enough for passengers nearby to hear. Elliot turned red and looked out the window.
“What? I thought you were my boyfriend,” Diane said, chuckling softly. She behaved the rest of the flight.
Elliot had almost forgotten about the pretend boyfriend component to their trip. He sighed when they landed, hoping that nothing regrettable would happen, hoping that no line would be crossed, then looking at his mother’s fit and curvaceous body from the side when she picked up her bag at baggage claim, hoping that something would happen.
“Good, so you two are there at the hotel now?” Valerie asked her brother on the phone while she was taking a break from one of the leg machines at the gym.
“Yeah here now, pretty tired, we didn’t sleep to well,” Elliot shot is mother a smile as she was putting clothes away.
“Well rest up and later go out and have a lot of fun!” Valerie suggested. They said their goodbyes, ending the call. Valerie ran her hand across her toned tummy, flinging sweat onto the floor. She got back to her intense workout routine with a smug grin on her face. Today was the day she would enact her plan.
After a long nap in each other’s arms, they headed off for some sightseeing, holding hands just like a real couple would. Elliot looked over to her and couldn’t help but smile.
They had dinner at a nice restaurant, Diane wearing another sexy dress. They arrived back at their hotel room, holding hands, and Diane began to unbutton and untuck her son’s shirt. “What are you doing?” he asked.
“Get on the bed, lay on your stomach,” his mother said, sliding his shirt off his shoulders.
“What? Why?” Elliot asked.
“Just do it,” Diane replied, running her hands up and down his bare chest. Elliot shrugged and did as requested.
A moment later he felt his mother take a seat on his butt. She began slowly running her hands up and down his spine, eventually rubbing the muscles with her thumb, causing slight enjoyable pain as the tension was relieved.
“Feel good?” Diane asked.
“It does,” He replied.
“I agree,” Diane said, moaning slightly. “I’m guessing your wife doesn’t do this.”
“Nope,” Elliot answered.
“That’s another pity,” Diane whispered, bending down, allowing her large breasts to rest on his back while she began rubbing his shoulders. “So tense. Just let it exit your body,” She whispered again, placing a small kiss on his neck, sending shivers down his spine. Elliot started breathing faster, but tried to remain calm.
Diane kept peppering his neck and back with kisses, “Close your eyes, breath slowly, relax.”
Elliot took a deep breath, thinking that this was ok, this was fine, and it’s just a massage. After several minutes he noticed his shoulders weren’t being massaged anymore, neither was his back. Instead the soft sound of kisses was heard. His mother had stopped rubbing his back and was only kissing it now. Dragging her breasts down his spine, she kissed all the way to the small of his back, her fingers gently scratching at his skin. Elliot was fully erect now, but tried to maintain his slow breathing. He didn’t want to turn on his back for fear she would see and feel his throbbing cock.
“Mmmm,” Diane moaned, sitting back onto Elliot’s butt. “I think I’ll grab a shower,” She said, ending their massage session, not wanting to push things with him too fast.
“Ok, great,” he said, trying to remain calm. When she closed the bathroom door, he sat up on the bed, running his fingers through his short blonde hair, “This is insane,” he thought.
He slept as far away from her on the bed as possible; hoping she caught on that he was very tired from traveling and still adjusting from jet lag.
As he lay there finally drifting off to sleep, he pictured his Aunt Tiffanie on her back deck. Elliot was holding her up against the wood railing, her arms outstretched to the side, her legs clasped around his body, and he was fucking her brains out.
“Ah yes! Yes! Harder!” His Aunt cried out in this dream. “Let it happen!” She said, just like she had done the previous evening.
Her tits bounced with each thrust, the moonlight illuminated her body, and she kept crying out in pleasure, “Let it happen!”
Elliot moaned in his dream, watching his Aunt throw her head back over the railing. When she lifted it back up to face him, her head was replaced with his mother’s. “Let it happen,” Diane said, gritting her teeth.
Elliot did just that, not letting up, slamming into her over and over again until he ejaculated into her womb.
He stirred from his dream, briefly waking, shaking his head and rolling over. The light peeped through the closed drapes in the center. The city lights would surely keep them awake if they left the drapes wide open. He rolled over once more and drifted off to sleep again.
Diane sat in the corner of the room, naked, out of sight in the darkness watching Elliot sleep, seeing him toss and turn from his little dream. She had been casually rubbing her clit. She stood and headed toward the window, opening the sliding door stepping out onto the balcony, still nude, not caring. She made a phone call to one of her contacts that owned a strip club in the area. She decided it was time to get extra naughty later in the week.
The next day they hit a few casinos, playing it safe, not gambling too much. Diane was on his arm always as they walked around and played a few games. He loved it. He kept replaying the dream in his mind and decided to let whatever happened in Vegas, happen. He also decided that he would not initiate anything, if they were going to cross a line and regret things afterward, he didn’t want it on his conscious that he caused it.
At dinner, the wine flowed. They didn’t have far to travel since this restaurant was on the ground floor of the hotel. Elliot was very drunk by the time they left. Perhaps he drank so much to calm whatever nerves he had. In his drunken stupor he asked his mother if he could be the one to give her a massage.
“Wait right here,” she slurred, slightly drunk as well. A few moments later, she appeared from the bathroom wearing one of the long white robes the hotel provided. “Ready.”
She sauntered over to where Elliot was standing at the window overlooking the city. She turned around, rubbing her butt against his crotch, playfully sliding the robe off each shoulder, pulling it down far enough to reveal she was braless underneath.
“Follow me,” she said, walking over to the bed, Elliot following her, stumbling slightly. His vision was blurry be he could tell she was laying on her tummy, breasts pressed against the mattress, overflowing to her sides, and the white robe was pulled down over her butt.
Elliot giggled, clumsily crawling onto her back, immediately bending down to massage her shoulders and kiss along her neck and back like she did the previous night. However, he did so in a far more clumsily and non-seductive way, due to the alcohol.
After several minutes of giggling and kissing on her back, he rolled over her, his vision blurry and his head pounding. “I gotta take a break,” he mumbled.
“Ok baby,” Diane mumbled back. She rolled over, and fell into his arms, resting her head on his shoulder. Her bare breasts pressed into his side, he was too drunk to notice.
“Head hurts,” He mumbled again, barely above a whisper. He started to drift off to sleep, hoping not to vomit, the room spinning in the dark.
Diane moaned, her own intoxication taking effect, “I want to suck your dick.” She nuzzled her forehead against Elliot’s shoulder. She sighed once more and fell asleep in his arms. Elliot thought he heard her speak but wasn’t sure.
“Hi sweety. You feeling ok?” Diane asked, meeting Elliot for breakfast a few minutes after he arrived in the lobby.
“Yeah, head is pounding though.”
“We’ll take it easy today. I’m sorry about last night.”
“Don’t be, we just drank too much,” He replied.
“Well, yes, but I just wanted us to have fun and I think the alcohol could’ve ruined that. I would never force you to drink or do anything you don’t want to do,” She said.
The next two days were fairly tame. Diane was sweet as usual; holding hands, giving him pecks, but didn’t push anything. Elliot spoke to Valerie, letting her know they were having fun. Diane called her sister, Stephanie, confirming their plans to meet up that evening after she arrived.
Stephanie was Diane’s 48 year old, equally bombshell-like sister, who posed in Playboy a few years after Diane. She was always a joy to be around. She was fairly mild mannered, so Diane was a bit surprised she decided to attend this event. Her son-in-law, Patrick, was equally pleasant and entertaining. Diane and Elliot were caught off guard a bit when they saw her on Patrick’s arm at the airport.
Stephanie explained she didn’t want to come alone, her children weren’t interested, and so Patrick came along. He had a huge, silly grin on his face. Diane chuckled; knowing that based on conversations with Stephanie, Patrick probably had a crush on her, so he was very happy to be there.
The four of them had dinner together, followed by walking a little along the Strip downtown. Stephanie posed in front of various landmarks while Patrick took her picture. The short, balding, late 20’s man seemed genuinely enamored with her. Both Elliot and Diane picked up on it and were amused.
The four ended up at Diane and Elliot’s hotel room, watching TV, and chatting a bit. Later on Diane closed the door behind them, telling them they’ll see them tomorrow, and hopped in the bed with Elliot, not bothering to change out of her dress. They again fell asleep in each other’s arms.
The next day the four of them spent together. They decided to go hiking at a nearby National park. At their picnic lunch, Patrick spoke up.
“Why don’t you two ladies go skinny dipping over there in that pond,” He joked.
“I’m sure you’d love that, wouldn’t you Patrick?” Stephanie laughed, leaning her head on his shoulder. Elliot and Diane shared an amused look.
That evening after dinner, Diane was exhausted from the hike. “You’re going out tonight,” She told her son.
“What? Where?” he asked.
“A strip club,” She answered matter-of-factly.
“Uh, excuse me?”
“You heard me. Go to this one,” Diane handed him a card with an address on it. “I want you to have some fun, unwind, and just enjoy yourself. I’m too tired to go with you, I need to sleep.”
“Mom, I’m not sure about this.”
“Oh please! Go! Have fun, alright? Just sit and watch the ladies,” Diane said.
Elliot thought for a moment and sighed. “Alright, sure why not?” he shrugged. “Might be kind of fun.”
“It will, now off you go,” Diane smiled.
When he left she called her contact at the club, “So what is the girl’s name? Crystal? I see, ok great. So she’s pretty good? Alright. Yes. Sounds wonderful, I’m glad I called if she’s only in town this weekend. Yes Elliot is on the way, I gave you all the info I have, you should see him. I will be there a little later on.”
Diane ended the call and got dressed. She was going to have a bit of fun tonight.
“Oh momma! Oh momma!” Patrick cried, his body shaking underneath Stephanie’s.
“Give it to me big boy!” She ordered. Patrick squeezed her big breasts, looking up to her. “Right there!” she moaned.
“Here it comes, here it comes!” Patrick exclaimed.
“Mmmm give your mother-in-law what she needs young man!” Stephanie played along.
“Ahhhh!” Patrick shook and convulsed squirting semen deep into Stephanie’s womb.
“There it is! Thank you,” Stephanie leaned down and kissed his face, rolling off him.
“Ahh yes, yes,” he moaned, catching his breath, his skinny body going limp.
Stephanie used the bathroom, checked her hair in the mirror, and picked out a sexy dress to wear. She peeped back into the bedroom, seeing Patrick asleep, as she predicted.
“Good, momma’s got an itch to scratch. A secret itch,” She said to herself, getting ready to head to a strip club.
Just as Elliot was feeling stupid for sitting alone at a strip club; a buxom, big breasted, brunette named Crystal approached him.
She had a thick southern accent and offered to give him not one, but two, lap dances back in the private rooms. Elliot sighed, shaking his head and smiling, “Sure. Why not? Crystal you said?”
“I sure did. Follow me!” She said, taking his hand, leading him through the crowd to the private area.
As she danced through the first song, he couldn’t help but notice how huge her breasts were. They were no doubt fake, but looked amazing. She slid and gyrated all around his lap. As the first song ended, she sat on his lap, and began to whisper in his ear.
“I’m only here for this weekend. So I’m going all out. My next dance will be a bit different. Are you ok with being blindfolded baby?” Crystal asked.
“Uh, well, ok?” Elliot asked himself allow. “Yeah sure,” he shrugged. Not once did he think of Cassie.
“Cool. Now relax, I’m not gonna hurt you,” She smiled placing the blindfold around his head. She stood up and smiled down at the blind folded Elliot. Just then Diane entered the private room, whispering for Crystal to wait outside. Van Halen’s “Hot For Teacher” started blaring through the speakers, a song Diane specifically requested of the DJ, who she has known for years.
Elliot felt a pair of large breasts on his face. He breathed in their scent. Diane squeezed them against his face, holding them there. She was wearing the same perfume as Crystal. They coordinated this quite well. She moved and gyrated her body against his erection, careful not to moan, her voice giving her away. Elliot sat there oblivious with his blindfold as this woman, went to her knees, dragging her tits across his crotch.
He gasped when he felt her start to unzip his pants, panic setting in, but quickly going away when he felt a hand resting gently on his chest, calming him. He started breathing easier when the woman’s hand patted his chest, while the other pulled his zipper down.
He was so hard and so horny. Elliot was going to take the advice he’s received lately and let it happen, even it was with a strange stripper – or so he thought.
Diane slid her hand down to Elliot’s crotch, pulling his pants further apart. She fished into his pants and pulled out his cock. Her eyes shot open as she looked onto his impressive member with astonishment. “Wow,” she mouthed.
“And back here is where you can give a private dance if you like. I really appreciate this, I’m short staffed tonight,” The manager told Stephanie, as he led her around the strip club, showing her the place.
“Well, like I said, I have some experience and would love to help,” She said. The manager moaned looking over her figure.
“Yes ma’am,” he grinned, grabbing his crotch. “Dressing room is down the hall that way.”
Stephanie nodded. “Ooh one more thing,” she tapped the manager’s shoulder. “What if, the customer wants a little more than a lap dance? I’m not saying it would happen, but what if, you know?” She asked, biting her bottom lip.
The manager nodded, smiling, leading her with his hand on her hip, “Peep in there baby,” he whispered.
Stephanie slowly pulled the curtain back a few inches and her eyes shot open in shock.
Her nephew, Elliot was blindfolded, and a blonde woman was on her knees in front of him, slathering his surprisingly large cock with salvia. Stephanie gasped, realizing the woman was her sister, Diane, when she turned her head to the side to lick along the tall shaft. She could barely hear Elliot but could tell, by his open mouth he was moaning.
Diane was enjoying every second and inch of this; unbeknownst she was discovered by her sister.
“Oh hi,” Crystal said, returning to her post outside their room. “Yeah that room is taken right now. She wanted to play a trick on her boyfriend,” Crystal explained.
“Mmhmm,” Stephanie nodded. “Where the dressing room again?” she asked the manager.
“Right through there,” he pointed.
Stephanie headed in that direction, with her mouth open, and waited a few minutes for the manager to move out of sight. She bolted toward the exit. Stopping once more at the private stall Elliot was in on her way out. Crystal was there, watching and smiling. Stephanie slid up next to her to peep one last time.
She saw Diane deep-throating, bobbing her head up and down on Elliot’s cock. “Oh wow, oh wow, that’s hot. Stop it Steph!” She chastised herself and scurried away, leaving the club.
“Ahh,” Elliot moaned, his semen filling who he thought was Crystal’s mouth. Diane hungrily devoured and sucked as much of seed as she could, keeping it in her mouth, rolling it around her tongue. She stood, throwing back the drape to signal Crystal to enter. Diane grabbed her and kissed her as hard as she could, letting Elliot’s sperm flow into her hungry mouth. Diane ended the kiss, holding Crystal’s head, letting semen flow out of her mouth onto Crystal’s, dripping some on her chin. Diane smiled, and nodded goodbye.
Crystal took the blindfold off Elliot, sitting in his lap. He smiled weakly, watching her wipe his semen off her chin. “Wow,” he managed to say. Crystal chatted with him a little while about basic information, where he was from, was he enjoying Vegas, and so on to buy Diane time to get back to her room.
When Elliot arrived, she was pretending to be asleep, the taste of his cum still on her tongue.
An hour after Stephanie arrived back at her room on the floor below Diane’s, an orgasm coursed through her body in the bathroom. Stephanie chastised herself again for being turned on by that naughty imagery, especially for briefly picturing herself and her own son, Dan, in that position. Patrick was still asleep thankfully.
“How do we look?” Diane asked Elliot and Patrick, her and Stephanie slowly spinning around in a circle for them.
“Yeah! You look awesome!” Patrick chimed in, a little too excitedly.
“You look great, both of you,” Elliot calmly said and smiled. His whole day had been great. He relaxed with his mother by the pool, feeling at ease, feeling happy, as though he received a secret blowjob the previous night far better than any he had received from his wife.
Stephanie kept her distance as best she could. Elliot didn’t notice her awkward behavior; Diane assumed she didn’t feel well.
“Come on, let’s get in the hot tub,” Diane led Elliot. He didn’t mind one bit.
Diane immediately straddled him, her breasts pressing on his chest. She began slowly kissing his neck. “Why are you being so nice to me?” Elliot asked.
“You’re my boyfriend for this event, remember?” She replied.
“Ah I see,” he smiled at her.
“I may just keep you as my boyfriend forever,” She said, kissing his lips.
“What about Cassie?”
“Would you ever cheat on her with another woman?” Diane asked, pretending she didn’t know Elliot received a blow job the previous night, much less one from her.
Elliot thought a moment, recalling the event from the previous night, assuming his mother meant a long-term, romantic relationship with another woman, not a quick blow job. “Maybe. It’d have to be the right one I guess.”
“I see,” Diane smiled, kissing his lips once more.
A few hours later, Elliot and Patrick were complimenting their dates on their short, solid lime-green, matching cocktail dresses. Stephanie glanced at Elliot a few times; he smiled back at her, not knowing what she witnessed the previous night.
The event was actually a little boring. Hugh Hefner gave a small speech and afterward did a meet and greet with the attendees, then he was off to his room. There was lively dance music. Elliot didn’t dance much at all, but watched his mother dance with photographers she hadn’t seen in years along with a few fellow models. Stephanie and Patrick danced a lot, Elliot chuckling when he saw Patrick discreetly attempt to grab her ass.
After a few hours, Diane was ready to leave, “Let’s go,” she took Elliot by the arm and said goodnight to sister. Stephanie watched them leave together, holding hands.
Diane slapped Elliot’s butt just as they walked out the door, “You were very nice tonight, thank you.”
Stephanie witnessed the exchanged and her mouth dropped.
Elliot stood looking out his hotel balcony window at the city lights below. No other lights were on in the room, but it was practically fully illuminated from the lights of the signs on the Strip. His mother was showering. Elliot smiled, thinking nothing had happened on their trip, they’d be home tomorrow night. He took a sip of wine and sighed.
A few minutes later he felt his mother slide her arm around his at his side. She was wearing the same large, white, bathrobe from the other night, her damp hair slicked back.
“So gorgeous isn’t it?” Diane asked.
“So are you,” Elliot replied, Diane squeezed his arm. Elliot placed his empty cup on the table next to him and turned to hold her. They both smiled in each other’s arms.
“Elliot, there’s something I want to tell you,” Diane said, ending their embrace.
“Sure, what’s up?”
“I was 37 years old when I met Bob. It was shortly after we moved to Charleston. I was secretly dancing at a seedy club and he came in. He was in town on business,” Diane explained.
“I gave him a private dance, it was normally like $10 or so back then. Well,” she paused, snickering, “he had me reach into his pocket when I was done and pull out what was in there. It was a roll of cash. $10,000.”
“Whoa. Must’ve been a great dance,” Elliot teased.
“Well, he wasn’t paying for just the dance. He was paying to spend the night with me. So I went back to his hotel room and I spent the night with him,” Diane said.
“Ah, I see,” Elliot nodded, slightly surprised.
“There was something about Bob that I found odd. I couldn’t place at the time,” Diane said.
“Really?” Elliot asked, he too, feeling the same about him.
“Yes. Over time, things became clearer and clearer. I would see him every once in awhile, a couple times a year, maybe once a year if things were busy. But as I aged, I could put pieces together. Wrinkles formed on my face, my lips were no longer as full, my hair was turning white,” she said, running her hand through her dyed blonde locks.
“When I visited Bob in February this year, we had sex in the shower. When I looked at him I saw something familiar. I saw myself. As I aged, I began to look more and more like my biological father. Him.”
“He’s your dad? Are you serious?” Elliot asked in shock.
“But grandpa – ” Elliot said.
“Will always be your grandpa. He will always be my daddy. Bob is a grandfather, yes, there is a difference. I sometimes call him ‘dad’, but he’s not my daddy, like your grandpa was.”
“I don’t know what to say,” Elliot replied.
“Bob is building a neighborhood on some land not too far from my house. He’s building several houses there. These houses in this neighborhood are for special families. Families that are very close,” Diane said, caressing Elliot’s face.
“I’m moving into that neighborhood once it’s complete. I’d like you to join me,” She said.
“Special? How? What do you mean?” Elliot asked.
“When I found out Bob was my father, we still slept together. We did it the night before we flew out here,” Diane said.
“Yeah, I know,” Elliot smiled.
“Anyway, after I found out who he really was, the sex became so much better than anything I’d ever experienced. It was like magic,” Diane chuckled.
“Why are you telling me this?”
“Because, Elliot,” Diane, stepping away from him a couple feet, bringing her hand to the tie around the waist of the robe, untying it, sliding the robe off her shoulders, letting it fall to the floor. “I want you to experience that magic too.”
Elliot’s mouth dropped. His mother was standing a couple feet away from him, naked, her enormous, perfect breasts on display, her body illuminated by the city lights outside.
Elliot was frozen with shock, his mouth hanging open. “Um, I, I, uh,” he said, staring at her breasts.
Diane smiled softly at him, slowly reaching for his hand, guiding it to one of her breasts. This was it. This the moment where Elliot realized he could let things happen.
Leaving his hand on her breast, he caressed the erect nipple with his thumb, and then gently squeezed the massive orb. “Wow,” he mouthed.
Diane took a step closer, running her hands up and down his chest, smiling as she began to unbutton his shirt. He watched her slowly work, each button coming undone, followed by her pulling out his tucked shirt. She caressed his face and slid his shirt over his shoulders, gently massaging them before pushing the shirt down further, letting it fall to the floor.
“Do you want to go through with this, Elliot?” Diane asked, pressing her erect nipples against his bare chest.
“Absolutely,” He answered, pulling her closer, smashing her tits against him, and kissing her with all his might. He bent down and picked her up, holding her by her ass, while she locked her legs around him. She was holding his face, kissing him madly, moaning as they tasted each other.
“I know I’m old, but don’t hold back,” Diane said, breaking the kiss.
“You aren’t old, and I won’t,” Elliot said, slamming her down on the bed. Quickly fidgeting with his belt and pants, he pulled them down, followed by his boxers, and climbed on top of her.
“Oh my,” She said, once again admiring his cock. “Take me,” she said.
Elliot went in between her legs, guided his cock in as quickly as he could, Diane locking him in place. He thrusted one, hard, impaling thrust, causing them both to moan. “I will,” he said, diving down to kiss her once more. Their tongues slathered around each other as Elliot rolled his hips into her, taking her over and over again.
She rolled him over, straddling him, moaning as he sucked a breast, “Oh yes, yes, I love you,” she cried out.
“I love you too,” Elliot said, releasing a nipple, rolling her once more onto her back.
“Ah! Harder!” She cried out; the bed banging against the wall, her fingers griping his back as he worked. A few minutes later she was approaching her climax. “Elliot! Yes!”
He didn’t stop. He kept going, rolling and slamming his hips into her over and over again as her body tensed up below him, shaking, her pussy spasming on his shaft. “Ohh! Ohh!” Diane cried out.
When her first orgasm subsided, she rolled over again, except this time they rolled off the bed onto the floor, laughing and rolling a few more times. Elliot went to his knees, guiding her up to straddle him, and lifted them both off the floor.
He gritted his teeth as he bounced his mother. Her wailing cries of pleasure echoing in the hotel room. Supporting her by her butt, he slammed her against a nearby wall, continuing his assault.
“I’ll be right back,” Stephanie told Patrick in the hotel room below Diane’s. She quickly made her way to their floor, hoping to confirm her suspicions. When she approached their room, she heard them.
Placing her ear on their hotel room door she heard her sister and nephew in throes of passion. “Yes! Yes! Don’t stop! Ahh!” Diane cried. Stephanie heard Elliot’s grunts of hard work. That’s when she heard a loud slam, startling her, causing her to gasp as their door shook. Elliot had slammed Diane against the door now.
Stephanie gasped and took a step back, she heard her sister cry out once more, “I love you! I love you! Yes!”
“Ah! I love you too!” Elliot grunted. Stephanie brought her hand to her mouth and ran away.
Eliot was tiring. He rolled her against the wall, eventually making their way to their bathroom. Sitting down on the toilet, he grabbed her face, kissing her hard, out of breath.
Breaking the kiss, his mother spoke, “Oh I want you every day, all day,” she said, rolling her hips, slowly squatting up and down on him as he sat on the toilet, holding her, kissing along her neck and breasts.
Diane grabbed his face, kissing him once more, while squatting up and down on his cock, “I want you to cum in me. I can’t get pregnant, too old. Cum in me.”
Elliot nodded, picking her up, walking with her to the bed, sitting on the side. She began bouncing on him, meeting his upward thrusts. “Ahh! Yes!” She grabbed his face, holding it in place.
“Ahhh yeah!” he grunted, letting go of her waist, grabbing her face in return. They held each other’s heads, their foreheads touching, as they thrust and bounced their way to a mutual orgasm.
“Oh wow, oh wow, wow!” Stephanie frantically said, rushing down the hall from the stair case. She opened her door, slamming it shut behind her. “Oh wow!”
“Hey there, sexy momma, you ok?” Patrick asked, with a goofy smile on his face.
“Shut up Patrick!” Stephanie said, moving toward him, grabbing his face, sticking her tongue in his mouth, guiding him to the bed. She had never been so horny in her life.
“Oh yes, yes, baby, yes,” Diane said, in between each breath. She was laying on top of Elliot, his cock still spurting semen into her. “So good, so good,” she said.
“Uh huh, it was,” he said, out of breath too. “Yes,” he added, running his hands up and down her back.
“What happens in Vegas,” He said, looking to his mother, she stopped panting, a concerned look on her face, “won’t be staying in Vegas.”
The smiled at each other and shared another kiss - a long, slow, passionate, kiss.
They kept going all night, missing a call from Valerie, not caring. The next morning they had breakfast with Stephanie and Patrick before their flight. She looked very tired and somewhat flustered. Patrick was in a great mood as usual.
“Shhh, quiet!” Diane snapped.
“Ok, ok!” Elliot said, he was trying to be as quiet as possible in the small airplane bathroom.
“I can’t wait to get home!” his mother said, her arms wrapped around him, his cock embedded deep while she sat on the small sink. They were joining the mile high club.
Later that day, Tiffanie picked them up from the airport, taking them back to her home so they could spend the night before driving back to Charleston.
They tried their best to be quiet; they tried their best to be discreet. Elliot and his mother couldn’t hold out until the next day.
At 1am, Tiffanie was startled awake by a loud bang. “Tom?” she asked creeping down the hallway with a baseball bat. She peeped in on her son’s room, seeing he was out cold. She peeped in on the guest room, but didn’t see her sister or nephew in there at all.
She made her to the kitchen, and saw the back sliding door; leading out to the deck was slightly cracked. She heard muffled voices. As she approached the door, she peeped out and was shocked at what she saw.
Out on her deck, in the moonlit night, her sister was moaning and lying on the wooden railing, her arms outstretched on both sides, holding herself there for leverage. Tiffanie’s nephew was holding Diane at the waist, slamming his cock into as hard as he could, grunting as he worked.
“I didn’t just see that, I didn’t just see that, nope, it was a dream,” Tiffanie told herself , heading back to her bed, closing the door behind her. “Nope, just a dream, going back to sleep now!”
The next morning Tiffanie saw them off, not making much eye contact. She realized it wasn’t a dream, and decided to pretend she didn’t see it.
“We have about 5 hours?” Diane asked her son from the passenger seat.
“Yep, unless we stop,” He answered.
“Sweety we’ll probably have to. I’ll need some of this,” She said, grabbing his growing bulge.
“In the meantime, you focus on driving, while I focus on this,” Diane smiled, lowering her head into Elliot’s lap, to enjoy one of her favorite car riding activities.
“We’re here,” Elliot said to his mother, pulling into her driveway. She sat up, releasing the cock that had been in her mouth the entire drive. Elliot didn’t stop, he wanted to get home and take her as much as possible and without having to worry about people being around.
Elliot was relentlessly fucking her in every single way in every single room of her house. Books were knocked off the shelf, the mail and magazines were flung off the counter, a lamp was knocked over, her house was a total mess. Her bedroom was in shambles. Everywhere Elliot and Diane went in a hurricane of sex; that part of the house was left in a mess.
Finally, after screaming, cumming, slamming the bed against the wall so hard the 52 year old Diane thought it would break; she collapsed on top of her son, sweaty and exhausted. It was evening, near supper-time.
Rolling off Elliot, catching her breath, she thought about her father, Bob, who she planned on calling to let him know she and Elliot had done it.
Later that night, Elliot called Cassie. Diane was on all fours before him, his cock slowly being serviced by her moving back and forth on it. Cassie answered and they chatted a little bit about the trip. Then Elliot told her he was staying another night.
“She’s not feeling well; I just want to make sure she’s ok. Tomorrow, I’ll come home and we’ll fix things, alright?” He asked, looking down at Diane’s ass, as it gently landed on his thighs.
“Alright, I missed you. I’ll see you tomorrow,” Cassie said.
“Yep!” Elliot replied, hanging up on her, tossing the phone on the mattress. He grabbed Diane’s hips and began stabbing her repeatedly from behind with his cock.
Like animals, they mated for the rest of the evening, never stopping, cumming continually, until they were raw.
Elliot collapsed on top of her, exhausted. Diane trailed her fingers through his hair, smiling, they were closer; they had experienced that magic she loved so much. Her plan had worked out.
The next day was horrible for Cassie. She reluctantly agreed to let Elliot have a divorce from her. She watched him drive away, back to his mother’s house, while crying.
Later that night, Diane was sitting on Elliot, bouncing up and down on his cock. Elliot had fixed things with Cassie, just like promised.
That night after Elliot had moved his things in and got settled at his mother’s; she took him to the neighborhood Bob was building.
“This is it. This is where our new house will be,” Diane said, shining a flashlight on the foundation and some piles of lumber.
“Do you think your sisters would really move in?” Elliot asked.
“I’m not sure. They’d have to have a unique relationship like us first. Those are kinda the rules,” Diane shrugged. Elliot nodded.
A few minutes later, unable to control their urges, they were naked once more on the construction site; rolling around on the ground, in the sawdust, in the dirt - screaming, moaning, and cumming; their sounds of passion echoing off unfinished structures.
Diane lunged at Elliot, after he went to his feet, pulling her up with him, causing him stumble backward into a dirt-filled wheelbarrow. Diane jumped on top him, causing the wheelbarrow to move. She began slamming and grinding her hips into him, further causing the wheelbarrow to inch closer and closer to a small embankment that led to the nearby marsh.
Elliot gripped her waist, egging his mother on. Her feet rest on the two handles as she straddled him, grinding them closer the small slope. Suddenly, Diane’s eyes shot open. The wheelbarrow was moving fast, with them in it, carrying them to the marsh.
“Oh no!” She cried out, attempting to contain her laughter. They rolled down the slope toward the marsh, Elliot holding his mother tightly. When they reached the muddy surface, the wheelbarrow sunk in to the thick, mud, buckling under their weight, tipping over and dumping them into the mud with a loud plop.
They were on their sides in the mud, laughing, Elliot’s cock still embedded into her, connecting them. “We should go. I’m pretty sure this is illegal,” Elliot said, standing up, helping his mother.
“Yes, I’d hate to get arrested here if a cop saw us,” taking his hand, shaking her head at all the mud on their naked bodies.
“I should stick to bedrooms. Maybe I’m too old for this,” Diane said.
“Yeah,” Elliot agreed.
“What do you mean yeah?” Diane glared at him, pretending to be angry. “You weren’t supposed to agree with me!”
“No I meant – ” Elliot didn’t have time to finish. His mother tackled him, taking them both back down into the mud.
They rolled around several times, finally coming to a stop with Diane the victor perched on top of Elliot, pinning his hands down, “Give me that cock, boy,” she demanded gritting her teeth.
Elliot snarled at her, pushing her off him onto her back, wet mud splashing from the impact. Diane gathered a handful and slathered it on his face. Elliot bent down, rubbing his face against her neck. They paused, glaring at each other, Diane slowly nodding her head.
Covered in mud, they fucked, not caring, grunting like animals in the marsh as they did. Elliot was behind her, pulling her hands back behind her, slamming into her as hard as he could - pieces of mud dripping off her jiggling tits. They both cried out into the humid night sky, collapsing into one another, as Elliot fell backward, laughing as he made a mud angel.
“I can’t wait to move here with you,” Diane said, lying in his chest, wiping mud away from his face.
Elliot smile faded when a large rain drop landed on his forehead, then another, then another. Within seconds the two adventurous lovers were caught in a down pour, laughing as they stood, the rain washing away some of the mud.
They made their way up the embankment, quickly grabbed their clothes, and rushed to the car. Still naked, Elliot stopped his mother, pulling her close to him just before they reached the car. In the pouring rain, he kissed her. It was a long, passionate, loving kiss, lingering for half a minute, his lips pressed firmly against hers.
“Oh Elliot,” Diane said, out of breath when the kiss ended.
“I think I’ve found my new wife,” Elliot said, smiling warmly at his mother.
They cleaned each other thoroughly in the shower afterward, taking their time licking and kissing every inch of each other’s bodies, before falling asleep in each other’s arms.
Across town, Valerie was screaming in pleasure.
“Yeah! Get that dick!” Ronnie yelled, slapping one of Valerie’s tits as she squatted up and down on his big black 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.
“I got a good pussy for you baby?” She asked.
“Yeah you do! It was made for big dick like mine,” Ronnie answered.
“Is it better than my mom’s? Am I better than her?” Valerie asked, out of breath.
“Yes you are!” Ronnie said, his black cock, now white with Valerie’s creamy vaginal fluids.
She smiled, grabbing his face, kissing him hard. She worked so hard for this, stretching her pussy out, exercise more and more. Her plan had worked out.
Valerie had no idea that at that very moment, her brother and mother were becoming one, making love, giving themselves to each other over and over. Diane had indeed forgotten about Ronnie.
In Minnesota, Stephanie was an absolute mess. Several times she thought about calling one of her sisters and spreading the news, but decided against it. She sunk into her bubble bath and sighed. “I can’t tell anyone, that’s just not right. Who knows what sort of damage that could do.”
She shook her head, piling up bubbles on her large breasts. She thought of her son, Dan, her hand casually landing on her thigh near her outer labial lips. A slight smile came across her face when she pictured him hugging her. Her finger involuntarily, under the water, grazed her clitoral hood, sending shivers through her. Stephanie shook her head of the image before it progressed.
“Maybe I’ll call him tomorrow and say hello,” She smiled, leaning back in her bath, closing her eyes.
“Hey Tiff, did I leave a brush at your house?” Diane asked her sister on the phone, lying on her stomach, as Elliot kissed her butt cheeks gingerly.
“Uh, nope, don’t think so,” She quickly answered. “How are you? Good?” She asked just as quick.
Diane looked over her shoulder at Elliot, licking her in between her cheeks, “Mmhmm, I’m good. You?”
“Great! Listen I gotta go, but I talk to you later!” Tiffanie replied overly enthusiastically, still denying what she witnessed that night in her home.
The truth was, Diane couldn’t talk long either. She led Elliot to the living room, sitting down on a chair.
“Time for a nice dance all for you!” She said. She pressed play on the CD player. Van Halen’s “Hot For Teacher” started playing, causing Elliot to give his mother a funny look.
“I love sucking cock to this song,” She said, sliding her butt across his erection before going to her knees. Elliot started smiling, putting two and two together.
She sucked his cock, followed by another marathon lovemaking session.
Diane felt wilder, younger, and sexier than she ever had before.
***End note: How the did Stephanie end up sleeping with her son-in-law? The first part in this series answers that if you are curious!***