Ben's hands trembled with nervousness and excitement. A pair of emotions he'd rarely felt together at this extreme. He kept them pressed tightly against his chest, his sweaty palms drying on his camp counselor Boy Scout T-shirt he wore to bed most nights. The smell of his stepmother's lavender hair conditioner had permeated beyond his covers and pillows. It now soothed the air he breathed as he stared at the slender neckline of the older woman laying in front of him. Over the past hour, she had inched her butt backwards towards him until his back was now flush against the cool wall.
I have nowhere to go; he thought.
It was a strange thought, he knew, especially since from the outside looking in, any other 18-year-old boy would kill to be in his position. After all, the middle-aged woman who had boxed him in this position in his own bed was a beautiful woman on top of being his stepmother. He felt the tip of his raw penis brush through the fabric of his stained boxers, Sharon's butt cheek. She was tucked under his covers with him, so Ben couldn't see her bare ass cheeks inching back into him, but he could imagine it.
Without even looking, he noticed Sharon's white and red polka-dot panties on when she entered his room that night. Her thick, creamy thighs nearly choked the panties from sight, but her tight tank top formed around her slender waist did little to conceal it. The moonlight caught the spaghetti straps of her white top draped over her shoulder. There was no tension in them where she laid. He imagined pulling them off her shoulders and seeing her top peal free from her full, thick breasts. They were the breasts of a middle-aged mother, no doubt. Wide, thick, and heavy. When he masturbated in the bathroom, Ben would imagine how they would feel. He'd fantasize about them bouncing free as she pulled her shirt off.
Ben's cheeks reddened as he felt the warmth flare in his face, contrasting with the icy wall that froze his back. The house's heater wouldn't turn on this Wisconsin evening in January. Or at least that's what Sharon said to him just before midnight when she popped her head into his room.
Her words started him as he laid in bed. Truth be told, he was lucky she didn't walk in on him in a more compromising state. Ben's bedroom was in the basement of their two-story house. An area that received little foot traffic during the day and at night there was nearly none, so he usually forgot to lock his door even when he should. So when Sharon stood in his open doorway and spoke, Ben nearly threw his E-reader across the room in shock.
"Oh, teehee sorry," Sharon giggled. At the time she came into his room, she wore a tightly sashed white robe that hugged her body warmly. "I didn't mean to scare you."
"Oh no, sorry. I'm sor- I mean I'm not- it's okay," Ben stuttered as he sat up in his bed.
"Umm... well, you probably didn't notice, but the heater's broken it seems. I can't get it to kick on."
"Oh really? Yeah no, it's always freezing down here, I didn't even- is there a guy coming to fix it?"
Sharon shook her head, pursing her lips, "not till morning." Usually Ben's father would spend three hours tinkering around with the furnace before admitting defeat and calling a guy to get him the job done. But, of course, his dad would have to be here to tinker around. Ben Sr. was in the middle of his three-month stint of a business trip to Taiwan at the moment. One of three he does every year, spending 9 months or sometimes more away from his family and home. Ben Jr. swore if his father wasn't wealthy his stepmom, Sharon, would have divorced him by now. They didn't have an open marriage, but his father didn't try very hard to hide the fact that various young and attractive women's names and pictures find their way into his phone.
Ben figured his father and mother viewed their marriage more like a business deal than a marriage. For an allotted expenditure every month, Ben's father had someone to watch the house, "care" for his son, and prepare his meals while he's home. In exchange, Sharon and her two adopted daughters lived a first class life. Angela and Brittany both were older than Ben by a couple of years or so, but still lived at home for obvious reasons. They had bedrooms upstairs, which Ben never resented. Ben was a nice guy, and he liked the feeling he got from seeing his step sisters smile when he could do or give nice things to them.
"You wouldn't believe how fast the temperature is dropping up stairs," Sharon said, holding herself and rubbing her arms up and down and pinching the neck of her robe closer together. "I gave Angela, Brittany, and her friend, Cynthia, all the extra blankets to sleep under tonight, but my bed is quickly turning into a popsicle. You think I can share your space heater?" Sharon asked lightly.
"Um- yeah, of course, go ahead," Ben said. He wasn't sure what she meant by sharing, but figured Sharon would take the space heater he kept running in his basement bedroom all winter upstairs to her bedroom. He did not expect Sharon untying her sash and slipping her robe off her shoulders in his bedroom. To be polite, he averted his eyes to the ceiling to prevent noticing her bouncing breasts as she walked or her panties buried in the crevasse of her crotch barely covering her sex.
"Umm... could you scoot over, honey?" Sharon giggled as she tiptoed back and forth in the cold air beside Ben's bed. Ben quickly retreated under the covers and back into the recesses of his queen bed in the corner of his room. Sharon flipped the light off and slid into the bed, backing her hips up some.
That was nearly an hour ago. It had taken her that long to trap him. Part of him, a big part of him, thought it was best just to stand up and go upstairs to fall asleep on the couch. That would be the gentlemanly thing to do, he figured. And that's what he strived to be. Ben enjoyed being a trustworthy guy. He knew he was the nice guy who 'finished last' in life, but that was the cost of being a good guy. His stepsister and I trusted him as well. Even though he had only known them for a couple years and 'family members,' he prided himself on not being a 'creeper,' who leered when they walked about the house in various states of dress. Ben valued they didn't keep secrets from him and could talk freely in front of him.
Sharon's slow moving ass cheeks lolled back against his hard-on, pressing his erection up as it flexed on its own into her butt. Ben clenched his teeth as the moment overwhelmed him. At first he thought his stepmother was coming onto him, but as time passed and he heard Sharon's deep, slow breaths, he questioned if she was even awake.
This is wrong. I should wake her up. I should leave or- she doesn't know what she's doing.
Just as Ben was on the verge of sitting up and putting an end to this, he saw Sharon's flush cheek turn slightly towards him, looking over her shoulder. About the time her round ass lifted and maneuvered so the tip of his cock pressed against the lower portion of the crack of her ass did her hand slowly reach behind her. Her ass tuck in some to make room as her small hand rubbed the side of his thigh and palpated down to his hard shaft that poked her. When her tender fingers wrapped around his shaft through his boxers, Ben's heart raced. No woman had ever touched him there before.
Ben's mind raced. He was an 18-year-old virgin caught in a position he never thought would happen.
What do I do? What's the right thing to do?
Sharon's fingertips caressed the tip of his penis gently. Coaxing it to grow and harden under her touch. When Sharon turned around in the bed, Ben was sure she could see the panic in his eyes through the dark, dimly lit room. Just as Ben could see the gentle curves of her breasts as they protruded out towards him and the flowing black hair that framed her face.
"You're poking me," Sharon whispered in a voice so soft it barely made a sound. He almost apologized, but Sharon didn't give him a chance. "It's okay, my sweet boy. I know you didn't mean to." Sharon said as her hands pressed on his hands against his chest, petting down to the belly of his shirt. "It's my fault, I know. You're just a typical teenaged 18-year-old boy with raging hormones and I just invite myself into your bed- what do I think would happen..."
"You know how you asked me earlier today for advice on how to get women now that you're heading off to college?" Sharon's fingertips slipped beneath the waistband of his boxers and slid back and forth along his waist, weaseling her hand inside. "You're such a good boy for letting your mother in bed with you," her hand slipped inside his boxers and lightly petted the base of his shaft. Her fingers brushed from the base of his shaft to the tip, her touch growing lighter as it neared his head. "Niceness is good, baby. Reliability... being a good boy... this will all help with women trusting you," she said as her grip firmed around his shaft. "Mmm... But girls don't desire a good guy. They desire a sexy man... a dominant man..." she whispered.
Sharon's fingers softly gripped his shaft, making deliberate pumps up and down repeatedly. Ben squirmed as he hummed a small groan as he felt a spit of pre-cum form at the tip of his cock.
"Oh, don't close your eyes, sweetie," Sharon said apologetically. Her breathing showed signs of labor as her hand worked Ben's shaft up and down faster. "Is this okay, baby? Does this feel good?"
Ben nodded without thinking. Looking through squinted eyes, he saw his stepmother's piercing gaze as she licked her lips. "You've never been with a woman, have you, honey? It's okay, you can tell me- mmmm... god you're so hard, baby. Are you a virgin, honey?"
Ben looked around nervously. Flush faced and being handled by his stepmother, he felt emasculated and vulnerable. He feared that a chorus of laughter would erupt from some corner of the room as the punch line of a bad practical joke would be revealed to be him.
"No, no- shh shhhh, come here sweetheart," Sharon whispered, cupping Ben's cheek with her other hand as her face neared his and she spoke even softer between panted hums. "Mmm... it's just you and me here baby, I'll take care of you for right now... We'll take it nice and- mmmm... slow, okay? Here. Do you want to feel my breasts? I see you staring at them-" Sharon giggled some as she looked down at her large breast beneath her white tank top. "I always see you staring at- ah ahmmm... oh, god..."
With his stepmother's coaxing, Ben reached out with both his hands and cupped her full breasts through her shirt and instantly felt her hard nipples on his palm. His thumbs instinctually rubbed out and circled her nipples, dragging up and down on them.
"Yess, baby, ohhh..." Sharon squealed through squinted eyes. "Careful baby, mommy's breasts are super sensitive. My nip- oh my- my- mmmmgod..." Ben's thumbs and forefingers pinched her nipples lightly, rolling them back and forth as her grip tightened on his shaft and her pumps became more focused and slow. Ben hadn't realized it, but his hips were moving now as he fucked his stepmother's hand, pushing his cock in and pulling out of her hand. "Oh, god baby, you're so big baby, I can't believe you're still a virgin, honey."
Pulling on the neck of her shirt, Sharon slid one of shoulders out of the spaghetti strap and pulled her breast from her shirt. The large, heavy boob fell to the bed to her side. The hard nipple pointing at Ben. "Here, do you want to feel mommy's bare breast? Careful, you've- mmm, you've already got mommy drip- ahhh ha! Dripping wet oh fuck..." Sharon panted as Ben squeezed her breast before feeding the bare, hard nipple into his mouth. His warm lips engulfed her nipple as his tongue made long wet laps on her.
"Oh, my god!" Sharon moaned so unexpectedly she clapped a hand over her mouth. "Oh god, Ben- suck on it- Ahh! Ahhmmm suck on my nipple baby, yes!" Ben's stepmother panted. Ben felt her pressing the head of his cock into her drenched panties that clung to her crotch. His humping hips ground the head of his cock up and down her panties as he leaked pre-cum on her. "Oh god- good boy, good ahhhoohh god!"
Sharon's silent whispers and kind, gentle words had slipped away the moment Ben's lips mashed against her thick breast. Her mind had clearly shifted from a guiding hand to a controlling force that yearned for orgasm. His stepmother grabbed at his outside hand desperately and pulled it up and around to her ass. The way she pressed his hand on her cheek, he thought she wanted him to squeeze her cheek, which he did. His fingers dug into the meat of her ass as his lips sucked harder on her nipple.
"Ahhh! Fuck! Baby... baby, mommy's nipples are so sensiti- ahhh oh god.... oh godd... push- push. Oh fuck, baby. Push your- push your finger in my ass, baby!" Sharon cried.
On autopilot, Ben spread his stepmother's ass cheeks and pressed his middle finger against her anus. Immediately, her moans turned to screams. Ben felt her hand clamp on the back of his neck as he bit down on her nipple just as his finger pushed inside her asshole.
"Ohhh godddd!! Ahh Ahh ahhhhh!" Sharon cried in a wreck of moans. Her body went rigid as her sex flooded her panties. Ben pulsed his finger in and out of her anus as his lips went blue, sucking on her nipple. Sharon went silent as the breath left her body and the silent orgasm nearly made her pass out. In a rush of air, Sharon sucked breath inside her and quickly pulled Ben's lips off her breast as if she was afraid the process was about to start again.
"God- baby, I... I'm...mmm..." Sharon mumbled as she held her head as if she had just woken up from a deep sleep and she was trying to gain her bearings. Her hand worked his shaft again, that was still throbbing in her palm. "Oh my god, honey, you weren't supposed to do that... I was supposed to make you cum, honey."
Ben's stepmother's hand pumped more quickly as her panted breaths neared Ben's lips. He felt her lift the absolutely soaked panties she wore and tuck the head of his cock beneath them. Ben felt the warm, thick, wet juices coating her pussy and hugging on the tip of his cock as she stroked him.
He groaned as he felt how warm she was. How slippery...
"Oh, god baby, your hard, young cock feels so good between mommy's thighs... I... ohmmm you're getting your mother horny again, baby... just... oh god..."
Sharon's hot breath bathed Ben's neck as she leaned into the crook of his neck, moaning. She pressed the tip of his shaft between her lips, dragging it up and down on her juicy clit as she stroked him.
Ben grunted and groaned and squirmed. Looking down, he saw his stepmother's breasts bouncing free as she writhed on him. Felt her hand pumping his shaft. The head of the cock was buried beneath her panties, swimming in her cum.
"Oh god yes, baby boy, cum for me. Cum for mommy," Sharon groaned in Ben's ear. He grunted back as his hands squeezed on his stepmother's back and ass tightly as he came hard. Flexing his shaft in her tight grip, Ben shot strings of hot cum across the lips of his own stepmother's pussy.
"Oh my god, good boy... shhhh it's okay, just lie still for mommy now," Sharon panted.
Ben breathed heavily as the world was a blur from the hardest orgasm he had ever felt. Slowly, he blinked away the blur as he regained control of his breathing. His dark bedroom came into focus as a lone figure appeared in his doorway that was open again. He saw the unblemished skin of the young, nubile woman. Her perky tits pointed towards him as the familiar face smiled at the sight of Ben holding his half naked stepmother tightly. 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. Cynthia was euphoric for many reasons as she knelt on the carpet. Her ring and middle finger were drenched in her pussy juices as she circled the lips of her sex repeatedly, a jolt of pleasure flooded her mind with every pass.
I'm so glad Ben's bedroom is in the basement, she thought. He gets so few intruders like me that he is willing to jack off in his room with the door cracked open.
Cynthia was hidden in the darkness just outside Ben's bedroom cracked door. A familiar enough spot she had been in over the years. The stairs were right beside his door as well, Cynthia would sometimes sneak away from her best friend, Brittany just to quietly go down stairs and sit there listening to Ben play video games or talk on the phone. She wasn't exactly sure when she began her infatuation with Brittany's little brother, but she knew now it was more than just a phase. She was in love.
Ben wasn't Brittany's real little brother, of course, their parents married a few years back so it was more like a new guy friend had found their way into their group of friends. He was awkward at first, but as the years went on Cynthia began to find herself yearning for Ben's calming presence when she was away from him. At first she thought it was a sign to hangout with Brittany more but Cynthia was already at her house everyday to avoid her own broken and unstable home. Her father used to beat her and her older brother until he died of a heart attack. Cynthia's older brother had been locked up for dealing drugs for years now, and her mom spent more time than not drunk and passed out on the couch of their apartment. Brittany's rich stepfather's house was an oasis of normality, but Ben, more than that, was one of the few men that was respectful in her life and treated her like a lady.
It was partially her fault, Cynthia knew, but the rest was men's doing. So many of them were dogs. And not cute, fluffy, lovable dogs, but wild untamed strays that trot around looking for something to hump or fight and that's all. She rewarded the behavior, though. Encouraged even. Ever since her body had developed into the luscious curvy yet trim body she had now, all the men flocked to her. Sexually, she quickly found her attraction, in some sick twisted-Freudian mishap, that she was attracted to the bad treatment.
In bed, Cynthia loved the hair pulling, ass slapping, choking, and dirty talk.she could explain it, all she knew was the treatment made her cum faster and harder than anything. The only problem was, of course, the same men would of course be a piece of shit in everyday life, as well. Brittany would often ask why Cynthia dated such assholes and why she didn't find a nice guy...
Maybe I have...
Cynthia plunged her two fingers into her pussy that slurped wet sounds with every fuck of her fingers. A sound that made her freeze, concerned he might hear it. But the headphone he had on and the porn he watched must've drowned out the sound she made. Ben was now 18 years old which meant he finally was legally looking at porn, not that Cynthia was much older at 19 years old. She couldn't see the video he watched but she saw the shadow on the monitor of a large breasted woman riding a large man.
Cynthia chewed on her lip as her eyes darted between Ben's face and his long cock. She tried to match her fingers fucking her pussy to the strokes of his shaft. As if every stroke of his shaft was him pumping it inside her pussy. She had longed to be fucked by Ben for some time now. It was an off the wall fantasy at one point but now it was a desire she needed. She must have him. The thought of his cock exploding inside her pussy. Shooting his sticky cum deep inside her.
Cynthia's fingers vibrated on her clit over and over as her eyes rolled back into her skull and the pleasure overcame her. She orgasmed three times before Ben finally shot his load into a clump of tissues in his palm. Cynthia heard the moans explode from the porno when Ben accidentally disconnected his headset. The big breasted woman cried out fakely, "Oh, yes, son! Fuck your stepmommy right in her pussy!"
Ben scrambled to close his laptop before the moans rang through the house. Cynthia retreated and hid before she could be spotted by a now paranoid Ben. Sneaking back upstairs, Cynthia couldn't help but toy with an idea. If Ben desires his stepmom... maybe he should get her...
Chapter 2
Cynthia
"Hey," Cynthia said, startling Ben from his phone on his bed.
"Oh, sorry, hey," Ben said sitting up right. "What's up?"
Cynthia giggled at how quickly and easily Ben always apologized. You know, all he really needs is a spine and he might be the perfect man. "Your mother wants you to bring up any laundry you need done. She's putting in a load."
"Right, thanks," Ben said, scooping a few items of dirty clothes off the ground and tossing them into a laundry bag he had at the foot of his bed.
"You should enjoy it while it lasts," Cynthia smirked. "Once you're off at college you're going to be all on your own."
"What? You will be there," Ben said. "I thought you'd take over doing my laundry."
"In your dreams." Cynthia laughed. "What are you up to today?" Cynthia asked.
"Oh, I just was going to meet up with some friends. You know, last time I'd see them for a bit after I leave next week. but I'd be back later tonight."
"Anyone else you have to say bye to?"
"Not really," Ben shrugged. "Short list."
"So, no new girlfriends then?" Cynthia asked with a twist in her hips. Her pencil skirt lifted some as she moved.
Ben retreated, stepping back as his face cheeks reddened, "What? Um. Uh no, nothing- no girlfriends."
Cynthia smiled and leaned back against the door frame to his bedroom. The girlish smile drawn across her lips, her shirt raised up above her belly button, and her skirt inched up her thigh as her foot leaned back against the door frame. Cynthia caught Ben's eyes dipping below her eye line as he drank in her body. Ben was such a polite boy, him even having inappropriate thoughts about her caused Ben to feel ashamed. He looked down and fumbled with his stack of old high school papers on his desk.
"You know, you're a good looking boy," Cynthia said. "You don't need to be single for the rest of your life."
"I'm not- I mean, I won't," Ben said defiantly.
"You know, your stepmom has been talking about you. She even said she couldn't believe you were still single. She said how good looking you are, and how she'd like to give you some advice, you know, some like, pointers about relationships, but she didn't want to be too forward about it." Cynthia shrugged. "Maybe you should ask her about some advice at some point..." Cynthia turned to leave the room as she saw Ben pondering her words. With a final smirk she said, "just a thought..." before disappearing up the stairs.
Cynthia hung out up stairs with Brittany for some time just watching TV in her room. She listened to Sharon loading the washer downstairs. Time passed before she heard Ben's car start and leave the driveway. About the time Sharon was switching the load of laundry into the dryer, Cynthia snuck back down stairs into the basement. Opening Ben's laptop she looked up the website history on his browser. She found a slew of video all filled with curvy stepmom's being fucked hard by strong, muscle bound men. Men Ben wishes he could be like...
Cynthia found a particularly sexy video that was rather long and positioned the laptop so that it faced the open bedroom door. Pressing play, she looked at her phone and thought she timed it out right. The dryer should finish any minute, giving Sharon enough time to fold the clothes and come down here to drop off Ben's clean clothes as she normally does.
The video was 39 minutes long. She turned the video volume up so that it was definitely noticeable when Sharon came into the room. Cynthia found herself hesitating as she thought about leaving the bedroom. Was this a good idea? What if it didn't turn out as I thought? Is this what I really want?
The buzzer on the dryer went off indicating it was done. Leaving Ben's door open, Cynthia quickly snuck back up the stairs before Sharon came to finish folding the laundry. She was committed now.
Chapter 3
Cynthia
Breakfast was filling and exactly what Cynthia needed. The orange juice took the edge off of the slight hangover she had from the night before. It still was as surreal as any dream or fantasy she ever had. Glancing at Ben and Sharon when they weren't looking, Cynthia saw the awkward looks they gave another and their strange demeanor. Last night really happened...
The thought that she successfully orchestrated a mini threesome of sorts between her, Sharon, and Ben while Brittany and Angela passed out drunk was surreal. Almost as surreal as Cynthia having fingered Sharon last night.
Cynthia wasn't a lesbian. At least she didn't think she was a lesbian. She's never been attracted to women before in her life. Sure, to make the boys freakout before she and Brittany have kissed and touched each other. It never meant anything. It was just for shock value. Brittany and Angela were Cynthia's best friends. She didn't want to do anything to jeopardize their relationship, but at the same time she saw something in Ben. Something that was real and true. She saw a man she didn't just want to fuck, but a man she could see dating, living with... maybe even spending my life with...
Cynthia was risking much for this chance, she knew that, but what she didn't anticipate was her urges overtaking her like they did the night before. Having successfully manipulated Ben and Sharon into the same room for sex last night. Cynthia could help her horny curiousness. Huddled in her familiar spot outside Ben's door crouched at the foot of the stairs, she teased and tortured her own pussy for what felt like hours while Sharon and Ben navigated a real life episode of an online stepmom porn scene. The soft moans that escaped Sharon's lips made Cynthia swoon almost as much as the deep growls of Ben as he entered his stepmother.
To be true, Cynthia couldn't believe the two of them didn't hear her through the door. Her face was flushed to a sweaty temperature and the erotic moment had surged to a level she didn't plan for. Any reason or logic she possessed was gone. Drunk on horniness, Cynthia entered the sexual swarray in Ben's room without a thought. She fingered Sharon's pussy without hesitation. Cynthia nearly came watching Ben's long hard cock devoured by his stepmother, then only for him to cum on her face. God, Ben must've been in heaven last night.
The uncomfortableness between the three of them were equally matched, which was a good thing. It meant neither one of them were horrified or upset about what happened, but all of them knew the ramifications of what it could mean. Of what could happen if Brittany found out about Cynthia and Ben. If Angela or Brittany found out about Sharon and stepson. How would they react? How would anyone react? Why does doing something that felt so right, feel so wrong, too?
Sharon left to go about her day, hurrying off to the gym and the store to put distance between her and the house and those who lounged about the house. Brittany and Cynthia spent most of the morning and afternoon laying around the couch watching trash TV. Angela had to go see her man which she seemed especially annoyed about so she disappeared for several hours. It was sexually infuriating and frustrating laying on the couch and imagining Ben down stairs all by himself. He was alone. He was hiding like the nice, shy boy he was. Maybe he was even stroking his shaft right now? Thinking of me coming down there and finding him, just like in one of the porn vids he watches. I was so close to his cock and yet I didn't taste it last night. I didn't feel it inside me. He could be fucking me right now. I could be downstairs wrapping my legs around his hips and force him to cum inside me.
Cynthia rubbed her thighs together under her sweatpants and hoody she wore. She had to think about something else. She had to focus on something else because she was starting to pant. Sooner or later Brittany is going to ask why she was constantly flush and sweaty and acting like a bitch in heat every time she was within 10 yards of her little step brother. Eventually, she would have to admit her intoxicating lust and love for Ben.
Cynthia didn't know how Brittany would take the news. She thought she would support Cynthia in most of her healthy relationships. Brittany was a good friend like that. And she liked her stepbrother almost like a gay best friend. Ben was a nice trusting guy who she felt like they could be roommates. In fact, that was even discussed since all three of them would be going to Boston University starting next week when Ben started college and Cynthia and Brittany returned for their sophomore year. Angela lived with her boy toy so she was out as a roommate, but the three of them could still live together.
It was Ben who turned down living with Angela and Brittany. He was too shy and reserved. He probably was afraid of the boisterous and loud girls cramping his style. Over shadowing him. Cock blocked him from getting his first girlfriend.
Brittany stood up and stretched, "I've got to go."
"Where?" Cynthia asked.
"I told you. I've got to pick up those clothes Sarah wants to get rid of. She wanted to get lunch and give them to me before I leave for school. You want to come with?"
Cynthia rolled her eyes, "you know better."
"Come on, you two need to make up," Brittany whined. "I can't be the ref between you two for the rest of my life. She's not that bad."
"No, I'm secretly hoping she just magically drops dead or disappears..." Cynthia rolled her eyes. "I thought you'd stop hanging out with her after high school."
"Well, she hasn't dropped dead yet," Brittany shrugged. "So you're just going to chill here all day instead?"
"I'll be okay, I'll find something to do," Cynthia shrugged.
Chapter 4
Ben
Ben packed his handfuls of luggage with clothes and electronics... to be honest he was only half paying attention to what he packed inside the bags. The various levels of distraction he had going on was insurmountable. Should I distract myself by thinking about my stepmom fucking me then me cumming on her face? Or how about my stepsister's best friend coming into my room naked and fingering my stepmother while she sucked my dick?
Ben didn't have a clue how things could happen and change so drastically over the past day. He had discussed leaving for Boston University early next week but now he was considering leaving first thing Monday. Hell, maybe even tomorrow. My apartment is ready. I can leave now before things get weirder between me and my stepfamily.
The cellphone vibrated in his jeans pocket and Ben looked at the screen.
Cynthia
Wyd?
Ben
Nothing. Y?
Cynthia
Brit wants you to get your clothes you left in your stepmom's room.
Ben
I didn't leave any clothes
Cynthia
She said they mixed up in laundry
Ben
Ok
Going upstairs, Ben was intent on avoiding Cynthia and Sharon as much as possible. Sharon should still be at the store or gym, wherever she went, and as long as Brittany was around Cynthia should not make things weird. Or any weirder than they already are.
Ben's plan was simple. Avoidance. If he could avoid them for the next 48 hours, this could all be another distant awkward memory. He didn't really care about what it meant for his father and stepmother. Frankly, he was convinced they'd be separated by the end of the year the way they were going at it usually. Of course he wanted to have sex with his stepmother, again. Of course, he wanted to see Cynthia naked, again. But at what cost? Ben had spent the entire afternoon weighing the pros and cons of trying to recreate what happened last night to happen again, and sure, it would be great if it happened and everyone stayed quiet and then his dad and stepmom separated. But what if they stayed together?
What if they were together for the rest of Ben's life and every Christmas for the next 50 years he would have to feel awkward and ashamed for this weekend? What if Brittany finds out and is filled with hate and anger towards Cynthia and Ben? Brittany, pathetically, was his best friend. Ben couldn't imagine his best friend hating him forever- and then having to see her every visit home for the rest of his life. He'd be risking potentially, permanent displeasure for a brief fleeting pleasure. No, I already know what the right thing to do is. I'm going to get my clothes. Go to my room. Close my door. And I'm going to hide for the next 24 hours. Then, I'll leave first thing Monday morning for college. I just need to make it through the next 24 hours...
Ben made it to the second story of the house having tiptoed around the living room where the TV played and, he assumed, Cynthia and Brittany still sat. Creeping into Sharon's bedroom, Ben saw a pile of his clothes on the corner of the large King size bed. He walked into the room to grab the pile and heard the door close behind him.
Startled, he turned around and saw Cynthia standing behind him with a devious smile on his lips. "Holy shit, you scared me," Ben half laughed.
"Stop, talking..." Cynthia said without explanation and Ben complied. He stood in a daze as he realized how much her appearance had changed since this morning. Cynthia's hair was taken from the pony tail it was in and was washed. The hoodie and sweatpants she once wore had been exchanged for a pink pair of booty shorts that barely covered the lower curve of her thick butt. Her white top was scrunched around her full breasts that bounced freely beneath her clothes without a bra. But the low cut V of her shirt left plenty to stare at as she approached.
Cynthia took the clothes from Ben's hands and tossed them on the floor. Leading him by the fingertips, she brought him around the foot of the bed, passed the master bathroom attached to the room, and sat him on the far side of the bed. Ben couldn't help but think, this was my dad's side of the bed. The thought gave him an uneasy pause as he followed along.
"You've been avoiding me," Cynthia said as she loomed over him. "Did you not want to talk about last night? Did you not like last night?"
"I... I... no, I liked it I just-"
"You just... Do you not think I'm attractive now?" Cynthia asked as she entered his personal space.
"No, I just- it's complicated, you know. And-"
Cynthia took Ben's hand and lifted it to her breast. Through her shirt, Cynthia held Ben's palm to her breast and he instinctively groped and mashed the breast into Cynthia's chest. He watched her eyes close and her mouth pant as her nipples hardened and protruded from her shirt. "It's complicated? Mmm... Is that your cock I see hardening against your jeans right now? Do you think I'm attractive?" Cynthia asked as she turned around and placed her butt against Ben's lap. Twerking to the left and the right, she held Ben's hand around her body on her chest as Ben felt her hair brush his cheek as she panted.