Former Playboy Playmates Part 5: Stephanie and Son - Sex Stories

Former Playboy Playmates Part 5: Stephanie and Son

... looked incredible, always thought about flirting playfully with him, but taking inspiration of sorts from Diane, Stephanie couldn’t help but think of him as a grown man with sexual needs. Then the fantasies started. She pretended Dan would join her in a bubble bath, the shower, her bed, holding her from behind, feeling an erection against her back. Then Stephanie rubbed her clit to her fantasies for the first time two months after seeing Diane and Elliot. She never came so hard in her life. The taboo, naughty fantasy sent her over the edge quicker than sex with any man. She started flirting more and more with her son, purposely trying to make him feel awkward and uncomfortable, pushing boundaries each time. She would sit on his lap, tickle him, when her daughters weren’t looking, grab his ass. Christmas at her house was quite entertaining – for her. Dan, on the other hand, seemed visibly annoyed and confused by her behavior. Stephanie told herself she’d never cross the line that Diane and Elliot did. That changed when she masturbated a week ago with a new Christmas present she bought herself. It was a six inch dildo, fairly modest in girth, nowhere near as insane as her other dildos. Stephanie bought it for the sole purpose of pretending the flesh-colored toy was Dan’s penis. It was much smaller than cocks she had taken in real life, much smaller than her other toys, but that was the point. She didn’t care about Dan’s size – he was her honey. Christmas Day night, when her ...

... son and daughters left her home, pretending Dan stayed behind, she sat the dildo on a pillow, climbed on top, guiding it inside her, nearly climaxing immediately. Moments later, feeling the orgasm building, she thought about Dan lying under her, smiling up at her. “I’m going to do it! I’m going to cum,” she thought. “It’s going to happen.” She let herself climax, pretending Dan was inside her, no fingers stimulating her. It felt real, it felt wrong, and it felt amazing. After Stephanie’s shaking and convulsing body calmed down, she rolled off the pillow, thinking about her actions. “Would I really do this? Would I really do what Diane did with her son?” Stephanie had no idea, settling on using the toy to help realize her most naughty of fantasies instead of Dan’s real penis. On this night, before she and Dan left the next morning to spend a few days in their North Dakota cabin for New Year’s, Stephanie found herself again, sliding a dildo in and out of her. She was pretending she and Dan were having fun before the rest of the family arrived tomorrow night. She orgasmed again, just before Carrie got back with groceries. She greeted her daughter, helping her put them away, going over plans for the next day of travel. Dan was picking his mother up in the morning, driving a few hours north to the cabin; Stephanie’s daughters would drive up that evening after work. Stephanie figured she and Dan would have about six hours alone, including time alone in the car. She thought about ...