Former Playmates Pt. 03: Diane and Son

"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.

"Yes!"

"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.

Chapter 8

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.

Chapter 9

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.

"It's ok, mom, really. Let's eat," Elliot assured her.

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.

Chapter 10

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.