Stepmother's Advice-Mine

Stepmother's Advice

Mine

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.