Former Playmates Pt. 03: Diane and Son

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."

Chapter 4

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.

Chapter 5

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?"

"Nope."

"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.

Chapter 6

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.

"Bob?"

"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.

Chapter 7

"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.