Step Mother's Advice-Undermine

Step Mother's Advice-Undermine

Part III

Chapter 1

Cynthia

...36 hours Earlier...

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.