Step Mother’s Advice Rebound

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.

None of the kids had left their bedrooms yet, but Sharon could hear them stirring in their rooms. She had a twinge of anxiety chomping at her from the inside. She hadn’t spoken to Cynthia since she had fingered Sharon to orgasm- nor had she spoken to Brittany since she allowed her best friend to finger her to orgasm. And Sharon hadn’t spoken to Ben either since he came in and on her mouth last night. After the shockingly delightful experience, Cynthia left the room, gathering her clothes at the foot of the stairs, and Sharon left soon behind her, wiping her chin.

It was a strange experience. The vulnerability mixed with the control she felt. It was a surge of arousal after years of no sexual contact with another man. Sharon wasn’t sure what to think or how to feel. Her stepson’s feet jogging up from the downstairs made Sharon’s anxiety spike. Her hands went cold and she felt a sting of sweat on the back of her neck as the nervousness set in.

What do I say to him? Do I act normal? I made breakfast as normal so I have to act normal. What is he asks- or apologizes… What if he wants to talk about last night? Just act in control. Like it’s all part of the plan.

Ben topped the stairs at the entryway to the kitchen and opened the door. His eyes met Sharon’s and immediately darted to the ground and back up to her, “hey,” he said.

“Hey hun, how’d you sleep?” Sharon asked brightly with false confidence.

“Er- um fine… good, yeah, good. How about you?” Ben asked, sitting at the kitchen island.

“Good! Oh yeah, I slept great,” Sharon said, retrieving plates from a cabinet and setting it down in front of him. Sharon’s cheeks blushed when she noticed Ben’s eyes dart down to her ample cleavage revealed from her black top. In an instant her mind was a blur of pornographic scenes involving her stepson swiping the counter clean of plates and him ravaging her body right then and there in the kitchen.

Sharon turned and made eye contact with Ben for a long moment. They shared the silence as their eyes met. The longer the moment held the faster Sharon’s heart thudded like it could happen any second. She was ready to jump her stepson right then and there. But the accompanying sound of feet clattering down the upstairs stairs dampened her heart rate immediately.

“Smells good, mom,” Angela said, stretching in her comfy hoodie as she snatched a piece of bacon to eat as she helped set the table.

“Get that last pancake, would you?” Sharon said as she pretended to look in the fridge for something. Allowing the refrigerator door to cover her red cheeks and hot face while it was cooled.

“Uugh… how can you two drink so much and not feel like death???” Brittany grumbled as she was the last one to stumble down the stairs. While Sharon’s daughters wore sweatpants and baggy hoody’s, Sharon couldn’t help but notice Cynthia’s skimpy form fitting top that revealed her belly button. A look that was complete with her bright pink short shorts that revealed her round bubble butt.

“We didn’t drink as much as you,” Cynthia said as she gave a smile to Sharon. Reaching for the orange juice, Sharon stepped back and noticed her stepson glancing at Cynthia’s protruding ass.

“Wow, look at you,” Angela said, dropping the last pancake onto a tall stake that she placed at the center of the island countertop. “Got a hot date today, Cyn?”

“Hmm? No, I just didn’t drink a whole bottle of wine by myself so I could wake up on time,” Cynthia said, smirking at Brittany. Brittany, who barely had her eyes open, replied by giving her friend the middle finger.

Sharon took a deep breath and having felt sufficiently cooled down, sat down on her stool with everyone else and ate breakfast. Aside from a few stray glances and smirks from Ben and Cynthia, the meal was free of awkwardness. Everyone ate their pancakes and laughed at Brittany’s hangover including Brittany.

It was strange being caught in the erotic circle with Ben and Cynthia. Sharon cared about both of them very much. She wanted the best for them in life and would do anything for them, but she didn’t have any special attraction to either one of them. Sharon didn’t lie awake last night imagining a life with either of them. She laid awake all night and fantasized about Ben fucking her until her legs shook. She imagined Cynthia finger fucking her until Sharon’s knees gave out. It was a strange primal addiction. Sharon wasn’t a lesbian or bisexual but just the thought of being sexually fondled by another woman while a man also had his way with her made her wet.

It was all too messy and complicated. Sharon decided she needed to clear her head after breakfast. While her kids lounged around the house and packed things for the move to college, Sharon went to the gym and tried to sweat out her frustrations. Afterwards, she showered at the gym and went out window shopping alone for the afternoon. The distance and small purchases felt as though they put a forgetful memory between her and the erotic complications she had left at home.

They would all be gone at school come Monday anyways, Sharon thought on the drive home. They’ll have the time of their lives- Ben with his freshmen year and Brittany and Cynthia in their sophomore year… who knows? Maybe Ben and Cynthia will find an interest in another.

Sharon dropped her shopping bags in the kitchen as she tossed her car keys on the counter. He black hair was still partially wet from her gym shower earlier. She went upstairs to her bedroom to change into something she could relax in around the house for the evening.

Ben doesn’t need anymore of a confidence boost from me. He’s a cute guy with a very nice cock… Sharon allowed her memory and imagination intertwine as she had a blitz of erotic images fill her mind. She shook the thoughts free at the top of the stairs.

He’ll be fine without any encouragement from me. I’ll just avoid being alone with him for the next two days.

Sharon opened her door and turned on the lights to see Ben laying on her bed naked with a massive erection and a pair of Sharon’s black panties strewed across the head of his cock.

Chapter 4

Ben

Ben’s engorged shaft throbbed as he looked wide eyed and dumb faced at his stepmother standing in her own door returning the same look at his naked body. He knew he should be less shocked to have been caught by his stepmother when he was laying in her bed naked, but he still was.

The sting of sweat pierced the back of his neck as heat flushed his cheeks and panic sent his heart into a rapid thump in his chest. His eyes darted down to his member that still wore a pair of his stepmother’s black panties strewed across his head. Ben quickly threw the panties on the floor and went to cover his shaft with the comforter.

“Hey! Not so fast mister!” Sharon yelped, stepping into the room. The door swinging and latching shut behind her. “You don’t get to Jack off to my panties AND ruin my good comforter with your junk- I just washed them.”

From the foot of the bed Sharon scooped the covers from Ben’s hands and tossed them to the opposite side of the mattress. Now, with nothing to even shield himself, he was completely exposed. His throbbing hard cock bobbed with each involuntary flex. There was a moment when Sharon seemed unsure of herself. Like she questioned if she should just leave the room or if she should stay.

The moment slipped away almost as quickly as her fingers slipped around his shaft. Stroking Ben’s cock, he admired his stepmother’s thick breasts beneath her black form fitting top. She had been at the gym, Ben knew because her long black hair was slightly damp as it hung over her shoulder and he could tell by the size of her breasts beneath her top that they were restrained by a sports bra.

He watched his stepmother stroke his shaft a few times while she licked her lips. Stealing a final glance up at Ben while wearing her wicked smile, Sharon flicked all of her hair over one side of her shoulder before lowering her lips to his shaft. Her full lips pushed softly on the tip of his cock keeping constant soft pressure on his sensitive skin. When her tongue snaked around the head of his shaft, Ben squirmed and grunted as his stepmother tongued his cock like a pro.

Sharon swiped her hair neatly over her shoulder as her head bobbed up and down again as she tongued and sucked his cock. Unbuttoning her shirt, Sharon popped her lips off of his cock, licking her lips as she panted while leering at Ben with a seductive smile on her wet lips.

“You’ve got such a wonderful cock, baby…” Sharon giggled as she crawled towards Ben on the bed. Through her dangling open shirt Ben could see the long line of cleavage. “I can see you’ve got that confidence Cynthia was talking about…” Sharon teased, her hand reverse gripped and stroked his shaft slowly. “How about advice… you still looking for advice from mommy?”

Ben’s heart fluttered in his chest at his stepmother’s soothing voice and familiar touch. All he could do was nod as he looked up at his mother who hovered over him. Peeling her shorts from her legs, Ben saw for the first time his stepmother’s tight trimmed bush as she swung her leg over Ben’s hips. The tip of his cock brushed against her ass cheeks as she tossed her shirt to the side leaving only her black sports bra restricting her heavy breasts.

Sitting back down as she fed the tip of his throbbing cock into her pussy lips. Like slicing into a cake, Ben’s cock pierced Sharon’s pussy slowly. “Aahhooohhhh… god…” Sharon groaned as the head of his cock pushed inside her. Arching her back, she slid down further his shaft until he was all the way inside his stepmother. The wide eye, high eye brow, and open mouthed look of shock on her face was a sight he wanted to remember. An image he never wanted to forget. It was the sexiest look he had ever seen.

“Oh god, baby, you know how naughty this is… you fucking your mommy like this, huh? Your stepmom fucking her son. You know how- ahhh… you know how naughty mommy is?” Sharon gasped as she slowly raised and fell on his hard cock. “Oooo, baby, you’re so hard for mommy. How long were you in her stroking that fucking dock and thinking about mommy? You were stroking your fucking dick in your mother’s bed? Ohhh Jesus… when did you get so fucking big, baby?”

Sharon’s fingers pressed into Ben’s chest and the tips of her hair brushed his cheeks as she panted slowly. Looking down into her stepson’s eyes she bit her lip, “mmmm… you want some advice on how to get a girl and keep her? Aahhmm…” she cooed as her tight pussy slid back down his shaft. Her fingernails dug into Ben’s bare chest as she whispered. “Fuck mommy’s naughty pussy and I’ll tell you,” Sharon said.

Not needing anymore coaxing, Ben bucked his hips slowly and clumsily, pushing his shaft inside his stepmother. She instantly moaned and closed her eyes. His chaotic hips pulled out and raised backup making high pitched yelps escape her lips.

“Fffuckk…” Sharon gasped as she focused down on her stepson. “Like- Ahh like this, baby.”

Sharon guided his large hands to her hips and Ben’s fingers brushed and squeezed her thick ass and thighs. “Slowly… slowly at first… yess baby, just like that…”

Ben slowed his pace and watched his mother rock up and down on his cock. Heard her coo and squeak with every slow firm thrust. Felt her soft skin as he slid his hands around her hips and squeezed her ass cheeks. “Oh, god ba- yes, yes- fuck me just ahhmmm.”

“Just like that!” Sharon cried out as she grinded her pussy on his shaft over and over again. “Oh god- yes… harder now- fuck mommy harder now, baby!”

Keeping the rhythm he had Ben began to flex his thighs as he fucked up into his stepmom faster. He watched as her large breasts bounced together up and down in her sports bra with every thrust. Her black sports bra nearly smacked her chin as she bounced on him. “Jesus- god! Ah Ahh… yes, fuck mommy ahmmm! Fuck mommy like a man, not like a boy- you’re a ahhh!”

Ben felt the surge of energy and aggression from the sound of his tender begging mother. Her sweet voice demanded sternness. His fingers dug into her bare ass as he gritted his feet thrusting hard up inside her. Sharon’s fingers fumbled at her sports bra trying and failing to pull it off her body. Without thought, Ben aggressively groped at the tight elastic band of the fabric. His stepmother collapsed against his chest as he pulled at the hands from her back. Her limp body folded on top of him. Kissing his neck. Panting her hot breath on his shoulder. When he peeled her clinging sports bra free from her chest, Ben felt his stepmother’s heavy breasts fall loosely against his chest.

Looking up at his stepmother as she clamored up right, pressing on his chest was the most glorious sight Ben had ever seen. Sharon’s pale white breasts, heavy, round, and perfect jiggling between her arms where she recovered, but Ben gave her no rest. Immediately, Ben bucked into her pussy. Thudding his cock deep inside of her, he felt her hot pussy juices flow around his shaft as he squished inside her.

“Ahhhagghh! Oh fuck, oh fuck- yes yes yes!” Sharon cried out. “Fuck me baby, fuck mommy- yes yes! Oooh god!”

Sharon’s fat tits bounced wildly between her arms. Her thick ass slammed down just as hard as Ben thrusted up into her. The sound of their bodies colliding was a loud thud of skin and meat pounding each other as Sharon’s grunts became primal and animalistic.

The sight of his naked mother riding his cock, the feel of her desperate fingers clinging to his arms, and the sound of her dirty words brought a surge of excitement to his head and the head of his cock. Ben reached up with one hand and groped his stepmother’s right bouncing breast. Pinning it to her chest and squeezing it as he thumbed her nipple, Sharon broke down into a mess of screams.

“Oh my god you’re gunna make- you’re gunna make mommy c- ughhh… I’m cumming I’m cumming!” Sharon screamed as her thighs went tight to his hips and her body trembled. His cock filled her up and went numb as he jabbed it inside his stepmother. Flexing hard, he shot long spurts of cum inside her soft warm pussy.

Sharon spasmed and seized on Ben’s chest as he grunted and groaned as the orgasm and his hard on refused to stop. Ben felt his cock twitch and flex inside his stepmother as he stared at the attached bathroom door and realized his stepmom just took his virginity.

Chapter 5

Ben

Ben stumbled down stairs to his bedroom exhausted. First, dealing with Cynthia and then his stepmother had put his system into overdrive. He felt like after getting his license, instead of getting a Toyota Camry, like he had, he was immediately shoved into a race car and forced to drive at top speed. I need a break. I need to think this through. I haven’t even packed for college yet and I’m leaving in days.

Ben walked over to his desk and grabbed at his limp cock through his pants, adjusting himself.

“Whatchya got there?” Angela’s voice started Ben and made him jump.

“Holy shit,” Ben turned, startled to see Angela lurking at his bed. “Angela, you- you scared me.” Ben said letting go of his crotch. Angela stood and walked over to him. Without notice she reached out and massaged his crotch gently through his pants.

“Awww… is maybe baby brother’s cock all tired?” Angela said in child speak as she reached into his pants and reverse gripped his limp cock. Her pink cheeks and glassy eyes were evident with how drunk she must have been.

Angela by no means was overweight or unattractive- quite the opposite, actually. Unlike Brittany and Cynthia who obsessively went to the gym everyday to take selfies of their butts and semi-sexual videos of their workouts, Angela led a much more leisurely life which gave her a very sexy hourglass body type. Thick hips, slender waist, and ample, natural, curvy breasts.

It was common knowledge that Angela’s longterm boyfriend was a pushover. A soft spoken man like Ben, but unlike Ben he had the sex drive of a kitten. It was a common enough complaint between Angela and her mom and sister that even Ben knew of it. She often debated the pros and cons of breaking up with him since her physical needs hadn’t been met in years.

“Aww… you so soft baby brother… your cock is like a thick piece of rope,” Angela giggled as she half stroked, half whipped his limp cock from side to side as it arched down. “What? Do you not think I’m attractive?” Angela asked as she pulled one of her large breasts from the V neck of her shirt. The fat breast was white, luscious, with the smallest stretch marks on the bottom side of it. Angela groped her own breast and pinched her own nipple pulling it out as she bit her lip. “Mmm… or is it because you just fucked my mother upstairs? Hmm? Is that why my baby brother is so soft right now?”

Angela must have saw the shock in Ben’s eyes because she giggled and smiled seductively as she bit her lip. Her grip on his shaft tightened as she stroked his shaft faster with more purpose. Ben grunted as he felt a jolt filled his shaft as it began to harden.

“That’s right, oh you didn’t think I heard you making her moan upstairs?” Angela asked. “You think I’m just okay with you- you fucking my mother?”

Ben recalled the advice from his stepmother- the advice from Cynthia as he looked down at his stepsister stroking his shaft. His eyes staring at her bare breast between them.

“Angela, are you drunk?” Ben asked, already knowing the answer. Her cheeks were red as kool aid and her breath smelled of the fruitiness of whatever she had been drinking mixed with the cut of vodka. It surprised him since it wasn’t much past 6pm and Angela wasn’t a big drinker. Which meant her drunkenness was deliberate.

“Just a little bit, why?” Angela giggled. “You want a taste?” Angela said as she leaned in and kissed him quickly. Ben tasted his older sister’s cold fruity lips and as her tongue pressed into his mouth and they swirled together he found the bite of vodka still on her taste buds.

Angela’s eyebrows danced higher as she felt his erection strengthen and his girth fill her slender palm. “Mmmmm…” she moaned into him as she kissed them harder.

The absurdity of the moment came and went in Ben’s mind. How could this be happening? First my stepmom Sharon, then Cynthia, now Angela? All in the same weekend…

A very small part of Ben wanted to stop kissing and ask Angela, and every other woman in the house in fact, what the hell was going on and why this was happening. But he also didn’t want to be an idiot and look a gift horse in the mouth, as they say.

Almost as fast as Ben grabbed Angela’s body to pull her deeper into the kiss did Angela get to work tearing off her clothes. Her shirt was tossed on the floor beside his bed revealing her pink bra and her ample breasts exploding over top of the bra. Ben gripped and squeezed her left breast as the bra was freed and fell to the floor. Ben’s cock stirred in Angela’s grip as she pumped his shaft at the sight and feel of her curvy plump breasts. He remembered Cynthia’s word of advice: confidence.

It was a struggle to be something he was not. Nothing about Ben proliferated confidence. He was a timid boy who was a people pleaser. But he knew the best way to please Angela was through Cynthia’s advice. Confidence. Ben’s thoughts turned to the porn videos he’d seen over the years. Videos of loud, annoying male porn actors were near abusive to their costar. But he found the few memories of actors he admired and was jealous of. Good looking men who were confident but not arrogant. In control but not harsh.

Angela slid her panties and gray yoga pants down and had one of her legs free from the waistband when Ben abruptly turned her around and pushed her over his desk. Angela yelped as she caught herself with her hands on the edge of the desk and giggled some as she stumbled to stay on her feet. Her giggles worried Ben. Was she laughing at me? Am I being ridiculous?

Ben pushed through. Fake it till you make it. He guided his shaft to Angela’s pussy and pierced her dripping wet lips with his swollen head. “Ahhohhh…” Angela moaned as she hung her head low. Ben was about to slam his cock inside her- this being the first time he had ever fucked a woman doggy style, but then he remembered what Sharon had said. Slow at first. Steady and gentle.

Slowly, he pushed every inch of his shaft inside her. Feeling her warmth and heat engulf him bit by bit. Ben’s naked stepsister flipped her head along with her hair back with a moan and whined, “oh god, don’t tease me. Fuck me harder!”

“No,” the word came out of him as if someone said it. “I’ll fuck you the way I say.”

“Mmmmmugh,” Angela whined a moan of protest as combed her long brown hair over her shoulder with her hand. Ben grabbed her shoulder with one hand and smacked her thick, fat ass cheek with one hand as he pressed his shaft completely inside her. “Ohhh yeah…”

Pulling out he slowly pushed back inside, seeing and feeling the eagerness of her ass pressing back against him. Twice more he smacked her ass cheek. “Ohhh ya, baby brother, smack that fucking ass!”

With slow forceful thrusts, Ben bucked his hips penetrating her pussy several times with his flexing shaft as she growled and whined for more. It was when her begging moans peaked and became near unbearable sounding that Ben’s hand clasped tightly on her shoulder and her hips as he began to fuck his older stepsister harder.

“Oh god yes, yes, yes! Ohhh fuck me,” Angela demanded. Ben’s cock pounded inside her pussy at a hard, steady pace. The clapping of their bodies filled the basement room as Angela struggled to grip the desk. “Ahh Ahh Ahh Ahh oh god- don’t stop!” Angela moaned.

Ben was so focused on keeping them upright and gripping her body he could truly appreciate how hot the moment was. His curvy sister’s body- her thick thighs, fat ass, and plump breasts bouncing and jiggling with every hard thrust.

“Ohm meh gawdyes!” Angela suddenly gasped in a desperate cry. Her head tucked down in concentration. “Oh godimcumming!” Her words came out together in a guttural groan. When Ben kept on fucking her at the same hard steady pace Angela went silent as her upper body collapsed against his desk. Her breasts flat against the table top, her back arched so her ass pointed back at him.

“Ohmygod! Yes! Yes! Jesus Christ!” Angela grunted through grinded teeth. What surprised Ben more than Angela, he thought, was that he didn’t cum. After rebounding so quickly after having sex with Sharon it seemed his stamina had improved.

A thin layer of sweat formed on Ben’s brow and chest as he pounded Angela’s pussy raw. His flexing shaft was stiff and filled her up with each thrust. His breaths and moans were ragged and animalistic. Angela’s legs were feeble and weary. Ben’s hand gripped a fist full of Angela’s hair as he pulled back slowly craning her neck back and arching her back for him.

“Ah ah ah ah Ahh oh fuck yes, baby brother- fuck your ohh Ahh fuck your fucking sister like the whore she is!” Angela cried. Ben slapped her ass again twice more. “Yes, oh… my… god…”

Ben tightened on her hair and her sweaty hips as he pelted his shaft inside her hard. The pace was furious as he gritted his teeth and flexed his abs pounding her. Angela’s luscious breasts bounced haphazardly, smacking into another and the desktop as she gasped for air. Ben held his sister’s hips up with one hand when her thighs went limp as he felt her pulsating pussy tighten on his cock.

“Oohhgodddd!” Angela exploded as Ben’s cock fell from her pussy and her juices squirted down her legs and his. She shrunk down to her hands and knees, collapsing in front of the desk as she panted. “Ohfuu- it it won’t stop. I I can’t- mmmmmnahh,” Angela mouthed as she writhed on the floor through the continuous orgasm.

It wasn’t until Angela’s orgasm finally passed and she began taking deep breaths to calm herself did Ben hear a whimper from his doorway. Without thinking, he walked over there. His hard cock still swinging between his legs.

“Oooomm,” the high pitched whimper came again and he saw even Angela had sat up from her place on the carpet to see what that sound was.

Ben opened the bedroom door and saw the young woman wearing a white top with no bra that exposed her hard nipples piercing through her shirt. She had a cornflower blue short skirt that was flipped up to her belly with her knees spread eagle. Cynthia’s slender fingers were fast at work on her clit, rubbing viciously on it. Ben saw her beautiful eyes pinched shut and her free hand clasped over her open mouth trying and failing desperately to muffle her escaping moans.

“Is someone there?” Angela’s exhausted voice sounded concerned.

Ben looked back at his naked stepsister then back at Cynthia who was still riding her orgasm. Ben smirked and thought of one word. Confidence.

And With that he reached down and startled Cynthia into a gasp as he grabbed her arm to bring her in his room.

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