Former Playboy Playmates Part 3: Diane and Son by tw_holt

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.

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