A Sidecar to Desirebynasty_dan©
Hailey Bryant sighed and slumped back in the seat of her car, which had refused to start, and slowly pulled the ring of keys from the ignition. It was 8:20 and she knew she would be late for work, even if she called a cab. It was the third time in less than a month that she had gotten to work late and she didn't think her boss would be thrilled when she called to say she would be late again.
She and her husband had divorced two years ago and, though he had offered to buy her a new car just last week, Hailey was determined to make it on her own. She and Rob were done, over with, and she didn't want anything from him. She realized that it was simple pride – misplaced pride – that made her turn down Rob's generous offer but she really didn't want anything from him. To accept a car from her former husband would be tantamount to admitting that she couldn't make it without him. It had taken her too long to get away from that self-possessed jerk and she wasn't about to let him know that she couldn't make it without him, when in fact she was going to do it come hell or high water.
She climbed out of the old Chevy and slammed the door, which was a sign of frustration, but she wanted to have the last word. In her way, Hailey was slamming Rob and not the car door. She stamped her feet once and turned and walked to the front door. Mr. Cramer was surely going to have a fit and she would be lucky to have a job by the end of the day.
As she was about to pick up the phone to call in, her eighteen-year-old son walked into the living room, dressed for school. Jason was a high school senior and would be graduating high school in two months. The only concession she had made with her ex husband was that he would pay for Jason's college, something she couldn't do. She couldn't even keep her car running, much less pay for her son's college education.
"Car won't start?"
"No." she sighed and picked up the phone.
"The alternator is fried, mom," he said.
"I'll get one on payday." She looked at her son. "Can you replace it?"
Jason shrugged. "Sure. Jerry and I can do it. It's a piece of cake."
"Ok. I'll give you the money when I get paid Friday." Hailey turned back to the phone. "I hope Mr. Cramer doesn't fire me."
"Why don't you let Jerry drop you at work?"
Hailey stopped just short of dialing the number for work and looked at her son again. Jerry Mason, Jason's oldest friend, drove a motorcycle with a sidecar. It was how the two got to and from school every day and Hailey's brown eyes immediately widened at the thought of her riding in the sidecar of a motorcycle. She burst out laughing as she saw herself seated in the old sidecar, wind blowing through her hair as the contraption motored down the street. She could also see her boss' face when she rode up in it.
"You're kidding, of course."
"Not at all. At least you won't be late. And we'll pick you up after work at four."
Hailey stared at him for a moment without speaking. "But, what about a helmet?"
"I have an extra one in the garage."
Hailey involuntarily raised a hand and lightly touched her shoulder-length blond hair. It was strait and soft and easy enough to maintain but she wasn't so sure about what it would look like after a wild ride in a motorcycle car.
"Your hair is beautiful, mom," Jason said with a grin. "The helmet will protect it from the wind. Besides, you can run a brush through it once you get to work and it will be beautiful once again."
She made a face. "Don't make fun, Mister."
"I'm not. You are a beautiful woman, mom, and a short ride in a sidecar won't change that. Besides, I've seen your hair messy before and it always looked great." Jason smiled, and then said quickly. "At least you won't be late for work again."
She sighed. "Ok, I'm game."
At that moment, they heard the tinny sound of Jerry's motorcycle horn and Jason handed his mother his helmet. He hurried to the garage, grabbed one that had belonged to his father and met Hailey in the driveway.
"Hey, Mrs. Bryant," Jerry said with a smile.
"Hey, man, mom needs a ride to work" Jason said when he walked up. "The alternator on her car is fried."
"Sure. We'll get you to work."
"Thanks, Jerry. I owe you."
"Don't mention it."
Hailey watched as her son climbed nimbly into the sidecar, then lifted her left leg to follow. It was a tight squeeze and she had had to raise her skirt a little when she got in. When she sat down the skirt was up around her waist and her panty-clad ass sat directly on her son's lap. She just hoped he hadn't noticed. Well, it was Monday and only four days to go before payday and by the following week maybe her car would be running again.
Hailey was sitting in the car, her long legs on either side of her son's legs, and facing forward. There was a small windscreen on the car and, along with the helmet, protected her from the wind that blew at them as Jerry drove the cycle down the street to the main street that bordered the residential area they lived in. They had gotten no more than four or five blocks when she felt something that was not normal. It was a few moments before she realized what it was.
Her son had an erection!
Hailey felt her eyes widen at that knowledge. She was sitting on her eighteen-year-old son's lap while his hard cock pressed hard against her ass! It was so bizarre, so incredulous that all she could do was sit and stare through the windscreen. Every jounce and jolt of the cycle just pushed the hard shaft of Jason's cock harder against her ass.
The realization that her son was aroused caused conflicting thoughts within her head. On the one hand, Hailey knew that it was wrong for her son to harbor sexual thoughts for her. She was his mother, and a mother and son don't have sexual thoughts and desires for one another. It's simply wrong. But it was also innocent, she knew, for a son to want his mother this way. It was just a way of life and the way young boys are.
On the other hand, though, she found she liked feeling a hard cock pressing against her ass. Even though she was still a nice looking woman for her age, Hailey was also thirty-nine-years old and Jason's mother. Wasn't it a compliment for a young man her son's age to become aroused with an older woman, especially if that older woman was his mother? And as long as nothing happened then it wasn't really a problem. Was it?
Still, the knowledge that her son had a raging hard on pressing against her ass made her a little uncomfortable. Hailey was embarrassed because she knew her son was also aware of what was going on. After all, it was his cock that pushed and strained against her well-rounded ass. She wondered if he was also embarrassed; obviously he had to know that she was aware of his erection.
Suddenly, the trip was over and she was climbing from the small sidecar. She thanked Jerry again, then bent and lightly kissed her son on the cheek as she had done every morning since his first day of first grade. She knew her face was a beet red and she saw with some satisfaction that Jason's face was also red as he tried to avert his eyes. At least he wouldn't be telling his friend about what happened. But, then, what young man would tell anyone that he'd gotten a hard on while his mother sat on his lap?
And it was then, as she turned to walk into the clothing store where she worked as a bookkeeper that she realized her pussy was wet.
Hailey was fortunate to catch a ride home that evening from a coworker, so there wasn't a repeat of that morning. That night, as Hailey and Jason ate supper and later watched television, there was a definite feeling of unease between them. Hailey wanted to talk about what had happened between her and Jason that morning. While she realized that what had happened wasn't the end of the world, that Jason had simply reacted to a female sitting on his lap, she knew that she should say something. She had to ease his discomfort but the words wouldn't come. She, too, was just as embarrassed as her son. And she realized – at least hoped - that it probably wouldn't happen again.
The next morning, though, before Jerry guided the bike two blocks away, she again felt her son's cock hard and pressing against her ass. It was hard and fat and lay between her cheeks as she bounced up and down on it. And, like the day before, Hailey found that she liked the feel of her son's cock pressing hard against her ass. In spite of herself and the voice inside her head that said it was wrong, she still couldn't help but enjoy it. It had been too long since she'd had a cock and it wasn't like she and Jason were actually having incestuous sex.
She cast a quick glance at Jerry. He was leaning forward with head and torso down to ward off the wind. Though it was April, there was a slight chill in the air and that was good. He wouldn't be able to see what was going on in the sidecar. She closed her eyes and began to take pleasure in the feel of her son's hard meat. Hailey's breathing became quick, tremulous, and she could feel her pussy becoming moist as the bike and sidecar continued to bounce down the road.
When Jerry guided the bike into the parking area and up to the front door, Hailey emitted a soft groan of dissatisfaction. She was reluctant to end the ride and wanted to keep going, to continue feeling her son's hard bulge against her ass. On trembling legs, she got out of the sidecar and bent low to kiss Jason. She saw his face was red with pleasure and could hear the shaky excitement in his voice when he said goodbye.
"You need a ride tonight, Mrs. Bryant?" Jerry asked as she straightened and grabbed her purse.
"If you could, Jerry," she replied in a voice that didn't sound right, but he didn't seem to take notice. "Sherry won't be able to take me home today."
"Not a problem."
Hailey spent the day in a whirl of conflicting emotions. No matter how hard she tried to focus on her work, she couldn't keep out the unbelievable erotic thoughts that filled her head with relentless persistence. At one point she found herself wondering what Jason's cock looked like, then how it would feel in her mouth and pussy. The tiny voice of guilt and shame that told her such thoughts about her son were wrong began to fade away after a few hours. And, before it was time for lunch, Hailey was imagining her legs spreads wide as she took her son's cock deep into her dripping wet pussy.
At lunch, she hurried to the ladies restroom where she sat on the toilet, her legs spread wide as she imagined making love to Jason while she rubbed her sex-swollen clit. One hand toyed with her hard nipples; pinching and pulling on them while the fingers of her other hand caressed and rubbed her pussy. As Hailey loved her nipples and pussy she whispered her son's name, giving into the burning lust that drove her closer to a mind-numbing orgasm.
"Jason...oh, baby," she hissed softly. "Please fuck mommy's pussy! Make mommy feel your hard cock!"
Hailey released her right tit and drove two fingers of her left hand deep inside her pussy. She gasped softly. She could almost feel that it was her son's cock driving hard and fast inside of her as she pounded her pussy with her fingers. Her hips began to rotate slowly as she worked her fingers in and out of her wet, hot pussy. The fingers of her other hand continued to rub her clit as the fantasy continued to play inside her head.
"Yes! Oh, Jason, cum for mommy!" Hailey groaned softly, trying not to make much noise as she felt her orgasm begin to build. "Fill mommy's cunt with your hot man-seed!"
Then she came. The thought of her son's cock deep in her pussy, filling her with his hot seed, took her over the top and it was all Hailey could do to keep from screaming. Her body trembled violently with the eruption of her orgasm and she began to whimper lightly as she rode it to completion. Finally, she stood on legs that felt like rubber and walked slowly to the sink. She ran splashed cold water on her face and took several deep breaths before she felt able to leave the bathroom.
The ride home that afternoon was much the same as that morning and the morning before. It was obvious to Hailey that she aroused her son, that he wanted her as bad as she wanted him. As Jerry guided the motorcycle toward her home Jason's cock was again hard for the entire ride. And she sat astride his legs with her ass squarely on it, wanting desperately to rock her hips back a little so her pussy would come into contact with his hard bulge.
But she had to take it easy, at least until she was sure that he really did want her sexually. The last thing she wanted was to cause any damage to their relationship. She loved her son with all of her heart and she didn't want to hurt him. What they were about to do, if it actually came to completion, was wrong and could very well do more damage than it was worth. And the damage could be irreversible.
While she knew she couldn't overtly seduce her son, Hailey realized that she could do things that might encourage Jason to seduce her. She realized that he probably wouldn't do anything on his own if everything remained the same. And she wanted Jason to make the first big move.
So, for the next two days, Wednesday and Thursday, Hailey decided to let him know that she wanted him. She began to gently rock her hips as they rode in the bouncing sidecar, pressing his bulge hard with her ass and pussy. She wantonly rubbed against his cock and this only fueled the fires of her lust and made her want him more. And after every trip, she had to hurry to the bathroom to play with her clit while hot, erotic fantasies played inside her head.
By Friday afternoon, while she was waiting for Jason and Jerry to pick her up at work, Hailey had determined in her mind that she would have her son. Every night that week she had lain in bed late at night thinking it through, trying to tell herself that making love to her eighteen-year-old son was the biggie of what everyone considered taboo. Parents did not have sex with their children. This was so far against what most people thought of as "THE NORM" that she would be ruined in town if it got out.
But she didn't care. For the past several days all she could do was think about her son and what he looked like naked. She thought of how his cock looked and fantasized how it would feel to hold it one hand while she caressed his cum-swollen balls with the other. She imagined several times while masturbating that she was on her knees sucking his hard meat before lying back and spreading her legs wide so he could fuck her cunt for hours.
On Friday afternoon at four o'clock when she saw Jerry's motorcycle pull into the parking lot, Hailey opened the door and walked out of the store on trembling legs. Ten minutes ago she had slipped into the ladies room and removed her panties, and then slipped them inside her purse. It was a part of her plan to let Jason know that she was willing and ready for him should he really want her. She just hoped that he pushed his hands up under her skirt this time; on the ride to work that morning, Jason had caressed her thighs for the last two blocks of the trip.
"Hi, guys!" she said in a perky tone hoping that her nervousness didn't show.
"Hey, Mrs. B."
Just as Hailey walked around to the other side of the sidecar to get in she saw Jason's eyes flick momentarily down to her legs. His eyes lingered for a moment longer than what would be considered appropriate before he raised them to her face. She sucked in a slow, deep breath when she saw the look on his face. It was obvious that her son was interested in her in a way that transcended the normal mother/son relation.
"I, uh, have the money," she said digging into her purse. "How much will this part cost?"
"I called Jack's Auto and they said it's gonna run thirty-five plus tax," Jerry said.
She handed Jerry a fifty and smiled. "Can we go home by Anderson Street, Jerry? I know it's longer but I've been in that stuffy old building all day and I need some fresh air."
"Not a problem, Mrs. B."
"Ok. Are we ready?" Hailey asked with what she hoped was a seductive smile as she looked at her son.
"You bet," Jerry piped up.
"I've been ready all day," Jason said softly.
Hailey nearly gasped. There was a wicked look in his eyes as he looked at her and Hailey felt her pussy becoming moist as she lifted one leg and began to squeeze into the small car. She felt Jason's hands on her hips helping her in as he had done every time that week. Then, unlike any time before his hands slid slowly and softly down her legs as she sat down on his lap. She quickly put on the helmet and Jerry gunned the bike and guided it back onto the street.
She had asked Jerry to take the long way home because she wanted the extra time to make sure that her son understood how she felt. She wanted him to know that if he wanted to fuck her she would have no objections. Hailey fully intended to pull out all of the stops because this would be the last ride on Jerry's motorcycle. Hopefully, before the evening was over, Jerry and Jason would have her car running again and there might not be another opportunity.
Suddenly, she felt her son's hands on her thighs, caressing slowly and softly before they had gone two blocks. She sucked in a deep breath and watched his hands as she felt his cock hardening under her. Without really thinking, she took his right hand and slowly pushed it under her skit then let go and waited. For a long, uncomfortable minute she was afraid that he wouldn't do anything. She thought that maybe she had mistaken everything that had happened that week and she was going to end up looking like a brazen slut.
Then Jason moved his hand up along the inside of her thigh until his fingers touched the smooth, shaven mound of her pussy. She gasped loudly as his fingers began to probe and rub her in places that no man had touched in a long time. She leaned back against her son and closed her eyes for a moment. It was really happening! Her son, her eighteen-year-old son was touching his mother's pussy! A small part of her knew that she should feel shame but all she could feel at that moment was how nice and erotic it was to have her handsome son rubbing her slippery clit.
She felt his other hand go under her skirt. He pushed a fat middle finger deep into her pussy and Hailey hissed loudly through her teeth. The motorcycle engine was loud and she couldn't hear the tiny whimpering sounds coming from her mouth, as her son's fingers loved her scorching pussy. She began to rock her hips a little, rubbing Jason's bulge with her ass, hoping it gave him pleasure.
Jason slipped a second finger, then a third inside of her cunt and she cried out softly. They were in an area of town where there were no houses and little traffic. No one would hear her, except for Jerry, if she screamed her lust at the top of her lungs. Still she was careful in the way she moved. Hailey just wanted to sit back and enjoy the touch of her son's hands between her legs.
Jason's fingers began to move in and out of her slippery cunt, faster and faster. The finger on her clit that had moved in slow, lazy circles, now moved faster, more determined. She felt her orgasm building within her and she moved one hand to her breasts, alternately kneading them. She continued to rock her hips, fucking her son's fingers that impaled her wet, hot cunt.
Just as Jerry was about to make a left turn onto her street, Hailey saw Brenda Jenkins, a woman she had gone to high school with years ago. Brenda smiled and waved and Hailey barely managed to wave back. At that moment the knowledge that they were passing by an old friend while her son's fingers fucked her slick cunt sent a powerful shudder deep inside her tummy, and Hailey came.