Step Mother's Advice-Undermine

"Yes," Ben said simply as his cock throbbed against the fabric that separated Cynthia's ass and him. Turning back around Cynthia removed Ben's shirt, then unbuckled his belt, and unbuttoned his jeans.

Cynthia's hands grabbed at Ben's waistband as she bent over. Her breasts bounced before Ben's eyes as she smirked. "Do you want to fuck me?" Cynthia asked in a raspy whisper.

Stuck in a tense stare, Ben replied, "I do..."

With a pull of her arms, Cynthia pulled Ben's pants and boxers off of Ben, leaving him naked before her with his throbbing cock pointing up at her. Ben felt exposed and realized he was completely naked while Cynthia was fully clothed. He wanted to reach down and put on his clothes but then remember Cynthia just took them all off. I don't want to be rude. She took them off for a reason.

"Lay back," Cynthia said with a smirk on her face. Ben did with his arms at his sides and his cock pointing tall into the air. Cynthia took Ben's palm and thumbed a massage into the center of it for several seconds. "Why is it you don't then? Fuck me?"

"I- its complicated," Ben stuttered as he felt his hand guided between Cynthia's thighs. His fingers were placed at the crotch of her shorts and he felt the warm, tender crevasse of her pussy lips. The moist bunch of shorts and panties that was open to him. "I- I don't know if... I don't want to take advantage of you." Ben stuttered as his middle finger began to rub up and down the center of her crotch.

Cynthia bit her lip as her hips rocked back and forth slowly, riding his hand. Her small hand reached out and delicately touched the shaft of his cock. His dick reacted by flexing and releasing a small drop of precum at her touch. Petting him, Ben's heart raced as he watched Cynthia licked her lips as she stroked him.

"Ben," Cynthia said, looking him in the eyes. "Look at me... does it look like I'm being taken advantage of?"

Ben felt his mind slip down a slope of self degradation and vulnerability. Like he was on display for the world to see, stripped naked to see how truly pathetic he was. He wondered if this was what Cynthia was doing now. Maybe that was what she was doing last night, too. It was all an insult. A form of torture. An elaborate prank making fun of how pathetic he was.

Cynthia must've sensed his mind slipping from the moment and his body retreating from her touch, because she moved onto him now. Onto the bed, she swung a leg over his hips and straddled him. Ben watched her pull her shirt off tossing it to the side of the bed and her luscious 19 year old breasts fall and bounce before him.

Cynthia looked down on him with passion in her eyes and something else. Something he had never seen before. Not truly. "Do I look like I want you?" She asked. Without waiting for a reply asked again, "then why don't you take me?"

Cynthia rubbed her hand up and down the center of Ben's chest while her other hand wrapped around the hard cock that flexed between her thighs. Stroking softly, she stared into his eyes as she stroked him over and over again. Her gentle fingers felt like a massage on his cock as the playful, goofiness that Ben had been used to seeing in Cynthia was gone. Her expression was of caring, of concern, and desire. With tender eyes she looked down at Ben as she stroked his cock with a look he had never seen. Cynthia looked at Ben with love in her eyes.

Ben's heart quickened as his cock flexed and stiffened in her palm. She was rubbing his pre-cum that leaked from his tip up and down his shaft. He was so close to cumming in Cynthia's hand when she suddenly stopped. Kissing up his chest, she kissed his neck, then sucked on his earlobe. Her hot breath massaging his neck as her nipples brushed along his chest with her swaying tits.

She removed her shorts and panties, tossing them to the pile of clothes with the rest so that she was as naked as he was then. She lowered her bare pussy lips down on Ben's throbbing shaft. Careful not to allow him to enter her, she grinded her soaked pussy lips up and down his cock. Arching her hips as she pushed her round ass out then dragging her hips down as she pressed her clit down on his hard member. Ben thought he could nearly cum just from the feel of her body on his. The sight of her breasts jiggling as she teased him.

"I see you..." she said as she continued to writhe slowly on him. Her breath labored as she hummed a moan between her words. "I see you better than you do. I see the man you can become. I see the life you could live. I see the man I'd stand beside... But that's not the man beneath me..."

Cynthia got off of Ben abruptly and went to the dresser beside the bed. Opening the top drawers, she pulled out a pair of black panties. My stepmother's panties... walking back over to the bed, Cynthia brushed the tip of the panties down Ben's face, his chest, then wrapped them around his cock as she stroked him with the panties gently for several seconds.

"I saw your stepmother, too," Cynthia said. "I saw the way she looked at you... talked about you... You should have heard her talk about finding porn on your laptop yesterday..."

"What? When?" Ben said, surprised.

"While you were out with friends," Cynthia shrugged. "You left your laptop open with stepmother porn playing when she brought down your laundry."

"No, I didn't," Ben said.

"She thinks you did." Cynthia said. Ben's eyes became recognition as Cynthia continued. "She also thought it was coupled as odd timing when you add in that you asked her for advice on girls before you leave for college..."

"But you..." Ben started.

"I told you. I see you. I see your lust after her..."Cynthia said, stroking his shaft with more purpose. Engorging his cock with his stepmother's panties around him. He felt his heart rate rise as the pleasure increased. "I'm the kind of girlfriend that gives into her boyfriend's desires. I'm the kind of girlfriend who wants her man to have everything he desires..."

Ben squirmed as he was near cumming. He was so distracted he almost didn't hear the thudding up the stairs as someone neared the bedroom door.

"But that's up to you. If you want to be the man you could become..." Cynthia said. Her words disappeared almost as fast as she did. Leaving the black pair of Sharon's panties draped across my cock, Cynthia snuck into the bathroom and closed the door just as the door to the hallway opened. Ben froze as he laid naked in his stepmother's bed with her panties on him as she stared at him from the doorway. This was another step in Cynthia's plan, Ben thought. She wants me to fuck Sharon while she listens, again.

Chapter 5

Sharon

Sharon was in a daze as she laid naked on her bed. With sweat on her brow and her breath finally coming under control, she stared at the ceiling. Ben had left her to go back down to his room a few minutes ago and Sharon still could not believe she did it, again. For so many years she had dealt with celibacy due to her estranged husband, she forgot how amazing it felt to have a man's cum inside her. She could feel it begin to leak from between her pussy lips.

Sharon had forgotten how much she loved sex. How much she missed being with a man. How much she enjoyed being around someone who was a good man. It wasn't like she wanted to be with Ben but the mutually beneficial relationship she had with him felt so good. It was exactly what she needed. Exactly what she wanted.

She heard the door open and looked towards the hallway where Ben had left expecting to see him return. Sharon found her pussy stirring at the thought of receiving more attention. But when she looked at the door it was closed. Sharon furrowed her brow as she heard the door continue to open and brush across the carpet when she saw movement out of the corner of her eye. It was her bathroom door. It was open and standing in the doorway was Cynthia's naked body.

"Cynthia! Oh my god!" Sharon said as she sat up. Her hands instinctively covered her breasts and pulled a cover over her thighs. "What are you- how did you-"

"I have a question for you," Cynthia said as she walked to the foot of the bed. "I know you care about Ben and I know you like him- he's a good boy. You're going to divorce his dad soon, aren't you?"

Cynthia's hand rubbed up Sharon's leg, startling her. Her palm cupped Sharon's inner thigh and rubbed higher and higher until she touched Sharon's warm, moist, tender flesh just around her pussy lips. Sharon felt her heart thudding in her chest. Her thoughts whirled in a maddening circle as she tried to focus on what was being said. She couldn't believe Cynthia was hiding in her bathroom the entire time she had sex with Ben. How long had she been in there? What was happening before I came home?

"Yes..." Sharon gasped.

Cynthia's fingers slid between Sharon's pussy lips, slowly pushing inside her with her fingertips before retreating again and again. Sharon's eyes rolled back as she released a coo. Cynthia's thumb swiped over Sharon's clit, spreading Ben's cum over her pussy lips again and again.

"I'd like to watch out after him when he leaves your house and you leave his family." Cynthia said. "Would you think I'd make a good girlfriend for him?"

"Oh, yes..." Sharon groaned as Cynthia's fingers pierced deeper inside Sharon's pussy. The juices from her pussy coating Cynthia's fingers with every pump.

"Would you talk to Brittany?" Cynthia asked. "And help convince your daughter I'd be a good girlfriend for Ben. I'd be a good person to keep him attached to the family."

Cynthia's fingers pumped Sharon's pussy quickly now making her breasts bounce with every thrust. Sharon's grunt became more guttural as she swooned in the bed. "Yessss... oh, god yesss... I will! Oh, god!"

Sharon had her eyes closed but when she opened them she saw Cynthia crawling between her thighs. Cynthia stuck out her tongue and made a long lap of Sharon's pussy from the base all the way to the top of her clit. Cynthia's eyes stayed locked on Sharon as she repeated the lick over and over. Lapping up every bit of Ben's cum that leaked out of Sharon's pussy, Cynthia pushed her tongue inside Sharon's pussy.

"Ohhhhgaadd. Oh god yes!" Sharon groaned as her thick thighs shuddered around this 19 year old's face.

Cynthia's tongue slipped up to Sharon's clit and began making circles on it just as Cynthia slid two fingers deep inside her pussy. The feeling of Cynthia's tongue vibrating on her clit mixed with the fingers fucking her pussy became too much to bare.

"Ohmygod! Ohmygod! You're going to make me cum!" Sharon moaned as she arched her hips and felt her clit sucked on by Cynthia's hot lips. Her body convulsed as a powerful orgasm took Sharon's body and flooded Cynthia's face.

Chapter 6

Ben

"No," the word came out of Ben 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!" Angela screamed, startled. Ben didn't hesitate. Pulling Cynthia to her knees beside the bed, her his throbbing cock. Cynthia wore a smile of excitement as she parted her lips as she took the head of Ben's cock into her mouth for the first time. Her eyes closed and her tongue lapped the head of his penis over and over as she savored the moment.

Cynthia's tiny hands wrapped around his shaft as she pumped his shaft while her lips worked up and down the head of his cock. With each push, her lips went farther and farther down his shaft making him groan.

Angela, tipsy from the alcohol, swayed from side to side where she knelt on the bed in a daze as she watched the site. Ben threw his head back in a grunt before looking down into Angela's eyes. There was curious interest in her eyes as she watched Cynthia devour his shaft. When Cynthia suddenly deep throated his entire shaft, gagging on it, Ben closed his eyes and grunted until she pulled her lips off of him.

When Ben opened his eyes Angela was on her knees beside Cynthia and grasping his shaft. Stroking his wet hard member she pushed her lips down his shaft as Cynthia took his balls in her mouth one at a time. Switching back and forth. Angela's massive breasts bounced as her head bobbed up and down on his cock. Their lips met around Ben's cock. They kissed and licked at the tip of his penis as Cynthia's hand cupped Angela's breasts.

Ben grabbed Cynthia by her arm and raised her up to her feet and pushed her down on the bed. Cynthia looked up at Ben with excited wonder as she was tossed around under Ben's charge. Angela was guided on top of Cynthia. Straddling Cynthia, Angela mounted her as she immediately leaned forward. Their breasts mashing into another as they kissed, experimenting with another beyond what they had previously.

Ben lined his hard cock up with Cynthia's pussy and pressed the tip inside her tight pussy lips. He felt the pressure squeeze on him as he pressed inside. He heard Cynthia moan while kissing Angela. Thrusting inside her, Ben had to force his bare cock in and out of Cynthia several time before he pushed all the way inside her.

"Arrghhh oh fuck!" Cynthia cried as Angela kissed and sucked on her neck. Bucking his hips Ben picked up the speed. "Oh my god, baby, yes yes fuck me!"

Ben gathered Angela's loose hair into a ponytail grip with one hand as he fucked Cynthia. His hand gripping Angela's fat breast with one hand as he fucked Cynthia's tight pussy. Suddenly, he pulled out of Cynthia and guided his cock inside of Angela's eager pussy.

"Oh god!" Angela cried out as Ben pulled her head back by her hair. "Oh my god, yess..."

With hard bucks of his hips, Ben fucked his step sister hard making her giant breasts clap together with every thrust. Cynthia pinched her nipples and mashed Angela's breasts together as Ben fuck her pussy raw with a hard grip of her hair.

"Ahh ahh ahh ahh ahh yeah yeah!" Angela cried out as another orgasm washed over her. "Ohhhh godddd..."

Ben pulled his cock out from her pussy and rammed it back inside Cynthia who wasn't ready. "Ahhhh fuck!" Cynthia cried.

Her legs closed around Ben's hips refusing to let him pull out as he fucked her deeply. Angela twerked her hips, grinding her clit down on Cynthia's wet clit as the euphoria erupted between them. The sweaty mash of bodies squeezed, pinched, grinded on another as the chorus of screams peaked.

"Oh god- oh god, Ben," Cynthia moaned. "Cum inside me. Cum inside my pussy baby!"

Ben gritted his teeth and groaned at her sweet words. His hands gripped Angela's thick hips as he fucked Cynthia's tight pussy. Cynthia's voice screamed, "I'm cumming I'm cumming oh god yes I'm- I'm... ahhh!"

Ben's cock spasmed hard as he released strings of hot cum inside Cynthia's tight wet pussy. She writhed just as Angela writhed as she came again, grinding her pussy on Cynthia's. Ben held his shaft inside Cynthia until the last drop of his cum had oozed out and inside of the girl before he collapsed in the bed beside the two women.

His oldest stepsister and his other stepsister's best friend. What a wild weekend. How did this happen? Where is this going?

After several minutes of them catching their breath, Angela stood up in silence, gathered her clothes and left Ben's bedroom. Cynthia and Ben remained naked in his bed longer. They held each other in silence with Cynthia curled into Ben's chest. He didn't know what would happen when Brittany came home. He didn't know what he would say to his stepmother when he went up stairs. He didn't know what would happen with his father when he finally came home from the business trip. What Ben did know was, he was going to be the man he was meant to be from now on.