Step Mother's Advice Rebound
Chapter 1
Sharon
Sharon felt Ben's body stiffen as they hugged. Pulling back, she saw him staring at something behind her, instinctively, she pulled a cover up over her chest as she turned around. In the doorway of Ben's room was Cynthia, Brittany's best friend since kindergarten. Cynthia stood in the dark room completely naked as she smirked confidently at the pair of them caught in such a compromising position.
"Cynthia!" Sharon tried to exclaim while scrambling to grab her white robe tossed on the floor and tie the sash closed around her naked body. "What are you doing down here?! You're not- we agreed... where are your clothes?" Sharon was off kilter in this very complicated, very messy situation, and wasn't sure if she should act like a mother, her son's lover, or friend.
"They're around the corner," Cynthia simply said, with her hands on her hips. "I thought maybe I could help."
"Help with what?" Ben asked, pulling the covers over his body higher than Sharon had.
"With you, silly," Cynthia said, stepping into the room.
Sharon could see and hear the uncomfortableness in Ben's movement and voice. The poor boy was so introverted that having two naked women in his bedroom was probably too much socializing for him. Sharon wasn't pleased that Cynthia had ruined her plans for this evening. The control she had and the dynamic she created with Ben was changed completely by Cynthia's presence.
Sharon had known Cynthia since she was a child which made this moment even stranger for her. Not that jacking off her 18 year old stepson didn't push her to her limits of comforts, but she had only known him a couple years and had always seen the way he stared at her when he thought she wasn't looking. He had also grown into being quite the attractive man. Though still more than a decade younger than him, she saw no long lasting harm in sharing her body and sexual wisdom with him if it meant boosting his confidence.
Cynthia on the other hand was a 20 year old woman- a gorgeous woman at that. Blond hair that reached down to the small of her back, beautiful big green eyes, and a curvy but fit hourglass figure.
Ben was probably throbbing again already underneath the covers just from looking at her.
Sharon wasn't sure what Cynthia had a specific change to their plan in mind but her coming downstairs definitely wasn't in the original. She thought about leaving and even moved for the door a step or two but was halted, first by Cynthia's gaze. It was a leering look filled with tease and seductiveness. She was very familiar with the look. Sharon, who was an avid dresser in skimpy, low cut tops, had collected her fair share of admirers in her life- though, all from a distance. Something Sharon had difficulty with was selecting the trusted one to go to the next step with her. A set back that had been detrimental to her love life over the last years.
One thing she was not used to was seeing the familiar look of seduction aimed at her from a woman. A naked woman who was half her age and naked, too.
"I'll give you guys some-" Sharon started but was beckoned over to the bed by Cynthia swiftly with a nod of her head telling Sharon to stay and not to go.
Sharon followed Cynthia over to the bed. "Hey, Ben, how's it going?" Cynthia asked.
Ben looked up at her with shifty eyes, "good... you're um... naked..." Cynthia tore the covers free Ben's lap revealing his while thighs and limp cock between his legs.
"So are you," Cynthia said with a hooked smirk. Ben scrambled to cover himself but with a slap of his hand, Cynthia knocked his hands away. "Nuh uh, you don't get to touch," she said, lowering to her knees and patting the front of the bed, signaling for him to scoot forward towards her.
With an unsure look on his face, almost humiliated, Ben moved to the edge of the bed with his shoulders sunken and eyes averted from Cynthia's swaying breasts. Sharon moved behind the young woman, crossing her arms. She wasn't sure what Cynthia had planned but she didn't like how emasculated Ben appeared. This wasn't the plan.
"Hey- don't look away, don't you like the looks of my boobs?" Cynthia asked. "Here, go ahead and feel them." She guided his hands down to her chest where his warm palms cupped her breasts like he had just done with Sharon's. Mashing them together and rubbing on her nipple, Cynthia closed her eyes and hummed a note of approval as she giggled to herself. "Mmm... you're having quite the night, huh?"
For the first time that evening, Ben's eyes lit up and widened with recognition as he looked between Sharon and Cynthia. He was beginning to understand this was a coordinated act and not just some scene out of a porno. Cynthia short circuited the series of questions Ben looked like he wanted to ask by reaching between his thighs and beginning to stroke his limp cock. Gently pulling and pushing on his shaft, she awoke his 18 year old cock as her free hand rubbed up and down his thigh.
"Did you know I always had a thing for you?" Cynthia smiled beneath squinted eyes up at him. Ben's cock grew and thickened. Her palm with every stroke. His head swelled and pointed at her lips. "I mean, you're cute, trustworthy..." her pumps became more purposeful now that his shaft throbbed before her. She used her whole arm to work his erection. She bit her lip with eagerness as she watched the drip of precum escape the tip of his shaft. "Athletic body... you're gentlemanly... but none of that matters though, you know that right?"
Cynthia's lips hovered inches above his cock. Her tongue neared his shaft but she smiled and separated before touch each time. Either her words or her teasing focused his concentration on this erotic scene happening to him. "You can be the sexiest guy or the richest or the nicest guy, and no woman who isn't looking to get paid for her time will notice you without this one thing..."
Cynthia stuck out her surprisingly long tongue and, while holding his now flexing hard shaft, up to his belly, made a long and soft lick up the base of his shaft all the way to the tip. Her tongue snaked around the head of his shaft and Ben shuddered as she made a long tender lick across his urethra that culminated in a long drip of precum dangling and stretching between her tongue and his cock as she pulled away. Slurping his cum to her mouth, she licked her lips looking up at the starry-eyed boy. "If you don't have confidence in yourself, no girl can see you," she said.
Ben internalized her words and realized he was slouching because he quickly straightened his back. Almost immediately he was rewarded by Cynthia's thick red lips pressing down around the head of his cock. Her head bobbed slowly as her lips worked tight, wet circles on his shaft. Lowering and raising she blew his dick. When Ben, in his astonished moment of pleasure, scooted forward and spread his legs to give Cynthia a better angle, she must have liked that as well, because her eyes locked with Ben's as her stretched lips slid all the way down his shaft and held, deep throating him. The sight of her stepson's eyes rolling backwards in pleasure as he groaned did make Sharon wet, she had to admit.
Sharon felt fingers close around her ankle, beckoning her to move forward and lower herself beside Cynthia. Cynthia's playful fingers brushed and tickled up and down Sharon's ankle as she pulled free from his shaft gasping for air as she stroked his shaft. More to be polite than any other reason, Sharon complied, swiping the robe cloth she wore away from her legs as she knelt beside the much younger lady.
Despite her comfortability with sex and her wealth of experience she had gained over the years, Sharon had never been around another woman in a sexual way. Her college years never involved any experimentation. She never kissed a woman or specifically found a woman arousing per se. So when Cynthia retreated from Ben's shaft and, in a pumping motion, angled his cock towards her as if she was passing her something to try at a buffet dinner, Sharon had a few hesitations.
Letting the moment take her away, Sharon dove in. Wrapping her lips around the tip of his cock, Sharon was greeted with the swirl of tastes of Ben salty shaft and Cynthia residual saliva. Sharon's lips quickly worked her way up and down the length of her stepson and his moans filled her ears and wetted her pussy lips.
"Confidence, Ben, that's what that feels like," Cynthia said. She took Ben's hand and guided it down to Sharon's cheek. Cupping Sharon's cheek, Sharon felt Ben's hand slide back pulling Sharon's black hair out of her face and making a ponytail out of her natural curls. Sharon was so focused on the throbbing hard cock before she didn't think much about it. She felt the strength of his grip as he tightly held her hair back in a ponytail and guided her lips up and down his shaft.
