“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.