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.
