Step Mother's Advice-Rebound

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.

Hands rubbed down Sharon's chest, warm in her robed shoulders then her neck. It wasn't until a hand slipped inside of her robe did Sharon realize it was Cynthia's hand. She stood behind Sharon and was hunched over as Ben fed his throbbing shaft to Sharon's lips. When Cynthia's hand caressed Sharon's breast gently like only a woman could, Sharon's eyes rolled backwards. Cynthia's fingers tenderly touched and played with her sensitive nipple which felt like a pulsating vibrator was pressed on her clit. Sharon felt her heart race the roller coaster of pleasure fill and fall from her belly.

Sharon wasn't far from orgasm when Cynthia's hands slid down to the sash of her robe. Undoing it, she peeled the robe from her shoulders. Sharon thought to protest- to pull away, and she might have if her stepson's hands weren't clasped around the back of Sharon head so firmly as his hips began to rise and fall as his cock fucked Sharon's mouth.

Naked and kneeling between her stepson's legs, Sharon felt Cynthia kneel behind her as the young woman's hands wrapped her hips exploring between her pale tender thighs. This was supposed to be an orchestrated plan executed against her stepson. If Sharon didn't know better, she would have thought that Cynthia and Ben were executing a plan on her.

Cynthia's hand pushed between Sharon's thighs to find her dripping wet pussy lips. Cynthia's finger slipped between her pussy lips causing Sharon to tense. Her fingers sliding along her wet flesh up and down, in and out.

It was more than Sharon could take. She wanted to scream. To cry out in moan but couldn't with her stepson's cock so deep in her mouth. Instead only a growl of a moan came out. The humming noise vibrates on Ben's shaft making him grunt. Cynthia's hot breath bathed her neck and ear as she felt the girl panting. Cynthia's free hand suddenly groped Sharon's breast, squeezing it and making a flood drip from between Sharon's legs. Cynthia circled Sharon's clit over and over again making Sharon's body to rock and writhe as the pleasure felt like a continuous bolt of lightning traversing her body.

The orgasm struck her so quickly and ignited her limbs she could do little else than kneel there and be face fucked by her stepson while the hands of her daughter's best friend molested her breasts and pussy, bringing to orgasm again and again. Twice Sharon's body went taut as she squirted on the floor in front of the bed as if she was a dog pissing in the house.

When the final orgasm finally relented she relaxed just in time to hear Ben's groans turn to strained grunts. His engorged cock spurted warm loads of cum on the back of his stepmother's tongue as he continued to fuck his shaft into her mouth until he began to go limp.

It was when Cynthia's hands fell away from her body and Ben's cock fell from her lips leaving a drip of semen on Sharon's chin did Sharon admire how exhausted and used she felt... and questioned why she loved it so much?

Chapter 2

Sharon

...2 Hours earlier...

"I mean, it was just open there on his desk," Sharon said, nearly spilling wine from the glass in her hand. "I felt bad for finding it. I felt sorry, but he left it clear as day out there..."

The girls were near death in laughter. Cynthia and Brittany were falling over another on Brittany's bed. Angela sat Indian styled on the carpet, clutching a bottle of wine in one hand and covering her teary eyes with the other.

"And his door was open! It's like he wanted me to find it!" Sharon exclaimed.

"Ohh god, oh my god..." Brittany said, trying to control her laughter. "Did you talk to him about it?"

"No, of course not," Sharon said. "I left his laundry on his bed and got out of there. I'm not going to tell him, 'hey, stepson, just so you know I saw your laptop open to stepmom porn in your room. Let's chat,' it's just odd."

Angela wiped the tears from her eyes. She wore an oversized t-shirt and underwear only which highlighted her thick thighs. Angela was Sharon's eldest daughter at 29 years old while Brittany was 19. Both were home for the summer from college and still pursuing their degrees.

"Maybe he was," Angela added as she took a drink of wine from the bottle.

"Was, what?" Sharon asked, standing in the doorway. She hadn't planned on staying, she just stopped into Brittany's bedroom to say 'hi' to Cynthia who was sleeping over for the weekend.

"Maybe he was trying to have you find it, maybe he wanted to get caught," Angela shrugged.

"What like a porn scene?" Sharon laughed. "I walk in on my stepson masturbating to milf porn and then have sex with him? Is that how men think it works?"

"That's how men 'hope' it works," Angela corrected. "Trust me men will try and find a way to make any scenario end with them getting sex." Sharon had raised her daughter to be very open and free spirited with their sexuality. She credits them for being on birth control early and using protection with sex with unfamiliar people. Sharon always talked sex with them, or in the instance of her current husband, the lack of sex.

Sharon wouldn't exactly be called depraved. In today's day and age there was, and she had, so many options of sex toys that with her husband's income she could handle her needs on her own. However, she did miss the touch of a man. With her estranged husband spending 9 months overseas on business trips, he and her were all but divorced at this point. While he has been quite the philanderer, Sharon chose celibacy for financial reasons. Mainly, if she got caught cheating, upon her divorce she would receive nothing.

Just another few months and Sharon would be married to Ben's father long enough to begin receiving alimony. But the notion of Ben, her husband's son, being interested in her sexually never truly occurred to her. Sure, she had seen the boy stealing glances at her low cut tops but all men did. Sharon looked at butts of cute guys on the street, that didn't mean she actually would go fuck them. But what if Ben actually was trying to create a circumstance to sleep with her? Sharon took a long drink of her wine as she stared at the back wall of Brittany's room.

"Look at her," Brittany smiled. "She's actually thinking about it!"

"Why not?" Cynthia chimed in. "Ben's cute, nice, funny- if I needed to get a Dick fix, he'd be the one I went to."

Brittany made a shocked expression but couldn't hide the smirk as she slapped her best friend's arm. "Cynthia! I forbid you from hooking up with my brother!"

"What? It's not like he's your actual brother and it sounds like your mom's divorcing his father soon anyways so-"

"Man, listen to her," Angela giggled. "She really thought this through."

"Are you actually interested in Ben?" Brittany asked, with the playfulness in her voice straightening.

Cynthia's eyes darted about before her face broke into a smile, "I'm just fucking with you- Sharon should be getting asked that question."

"No, don't be gross," Sharon swiped her hand at the seated girls.

"It's not gross," Cynthia said. "It's not like he's your actual son."

Angela nodded, "plus, he's leaving for college next week and you'll be divorced from his dad, who he hates too, before the school years are done. So you don't have to see him if you don't want. Like if it's weird."

"Plus he's super sweet," Brittany said with a pouty lip. "I always feel bad for him that he's going to college without ever having a girlfriend. He's so shy."

"Well..." Sharon hesitated.

"What?" Angela asked.

"Yesterday, Ben did ask me... he asked for my advice on how to get girls or get girls interested in him..."

Angela, Brittany, and Cynthia all smiled goofily as they looked at one another in silence for a moment before bursting into laughter.

"What?" Sharon yelled. "Don't laugh at him- that's mean!"

"We're not laughing at him, mom," Angela said. "He's trying to hook up with you."

"What?"

"Asking you the questions out of the blue, then leaving stepmom porn on his computer with the door open for you to see..." Brittany said. "He wants you."

Sharon felt her cheeks growing flush as she finished the wine. What started as a joke of a thought became increasingly more possible and erotic.

I can't be thinking about this? I have to stop this. I can't...

"Just go down there and talk to him about it," Angela offered.

"No, tell him the heaters broke and you need to cuddle for warmth!" Brittany giggled as she was obviously tipsy from the wine. Cynthia laughed at that idea.

"Okay, that's enough of this for now," Sharon decided, throwing up her hands. "Goodnight ladies, I'm going to sleep-"

"In who's bedroom?" Angela mused.

"Good night," Sharon patted her oldest daughter on her head as she laughed.

It was 10 minutes later or so when Cynthia came to Sharon's bedroom quietly. She glanced down the dark hallway as if to make sure she was spotted visiting Sharon's room and whispered with a smile.

"I told you guys, you can have as much of my wine as you like just no leaving the house ton-" Sharon said as she unmade her bed.

"No, not here for that- Brittany is already on the verge of passing out," Cynthia said. "I just wanted to say, I happen to have it on good authority that both Angela and Brittany wouldn't care if you fucked Ben and Ben would totally bang you- trust me... and its win-win. You clear your head and get to have sex with a man who's hot and not a douche and Ben gets a little experience and confidence before he goes to college."

Sharon felt the pull of possibility tug at her as everything Cynthia said made sense.

"It'd probably be the hottest night of Ben's life," Cynthia added. "Boys love this whole stepsister stepmother thing. All you have to do is say stepmom and they cum- trust me."

Sharon was shocked by Cynthia's bluntness. They had always talked about sex but this was the first time she presumed to give Sharon advice. Before Sharon could speak Cynthia dipped out of the room, whispering before she left. "Be a good stepmom and give your stepson what he needs."

And just like that. Sharon was left alone in her bedroom with the choice of either going to bed alone in her bed, or she could go downstairs to see her stepson...

Chapter 3

Sharon

Flipping the pancake over, Sharon shut the stove burners off as the bacon in the smaller pan to the side peaked in its sizzle and began to quiet. Sharon scraped the pan with the spatula and dumped the batch of bacon into the paper towel sheets she had on the table as the last pancake finished cooking. It was Saturday morning and a weekly tradition since getting married that Sharon cooked breakfast for her kids and stepson. A tradition that began to bring everyone together and get the family comfortable with another, now she wondered if they were too comfortable with another.