Mom's Three Weeks Off Pt. 01

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Starting her vacation off, a mother gets closer with her son.
15.7k words
4.79
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Part 1 of the 3 part series

Updated 11/26/2023
Created 09/17/2022
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Hello Reader,

This is my first time writing an incest/taboo story, but they have always been a favourite category of mine-especially mother-son focused ones. Here is a little story about two minor characters from my main series, Momma G.O.A.T. I hope you like it! Also, all characters are over the age of 18 and please forgive any grammatical mistakes; I am my own editor.

Deborah pulled into her driveway. With a sigh she parked her car and turned off the engine. She sat still for a moment, her hands resting at her side as she was unable to get the image of her son's cock out of her head.

Ever since earlier that morning when she had seen her boss, Tim, jerking off in his office to his lover, she couldn't rid herself of the almost mirror image she had seen a week ago. She had just come home from work after having gotten off early, and her son, Jason, had only had a half day at school so he had already been home by the time Deborah arrived. She guessed that Jason had thought his mom wouldn't be home for hours, and had decided to have a little alone time for himself. The reckless boy had left his door wide open, and it hadn't taken much investigative skill from his mother for her to find out what he had been up to.

Deborah fidgeted in the car presently as she recalled peering into her son's room that fateful day. She remembered climbing up the stairs after her son failed to respond to her call; her stockinged feet silent on the soft carpet. She hadn't meant to be sneaky, but as she was about to call out to her son again, his expressive moan coming through his open door gave her pause and she froze in place.

Standing in the hallway just in front of his door, the single mother waited, her breath bated as she listened intently. As she stood silently, Deborah could distinguish the steady "schlicking" sound that accompanied her 18-year-old boy's quiet moans.

99.999% certain what her son was up to, Deborah's cheeks had flushed immediately and she had felt herself creeping back towards the stairs. However, just as she was about to head back down, Deborah's legs had fidgeted, rubbing together. "Maybe he's working out..." she had reasoned to herself very unreasonably. Afterall, a mother shouldn't be so quick to assume that her teenage boy always has to be masturbating. She should confirm her suspicions just to be sure, so that she didn't lay any unwarranted, overzealous horniness on her precious son.

With that iron-clad rationale firmly in her mind, Deborah had felt perfectly reasonable as she crept, extra careful to be quiet, towards her son's door. Why she would be so secretive checking on her son's 'workout' didn't cross her mind.

This time, when she got to Jason's door, she poked her head around the corner, tilting her head so that her rich brown curls fell off her shoulders and she could look with both eyes. She had to adjust her horn-rimmed librarian glasses so that they sat right.

Thankfully, Deborah had managed to suppress her gasp, her hand going from her glasses to quickly cover her mouth, as her rich brown eyes widened in shock. Despite her silly reasoning that he might not be masturbating, Deborah discovered that not only was her 18-year-old son indeed jerking off, but her little boy also happened to have a HUGE dick; like the biggest Deborah had ever seen in person. Not that Deborah had seen many dicks to be fair, she had only ever slept with 3 guys, but nonetheless, she knew that what was in BOTH of her son's hands could not be normal.

Jason lay sprawled out on his bed, his lower half completely naked except for his socks. Why did men never take of their goddam socks? She wondered briefly before taking in the rest of her son. His head was tilted back and his eyes were closed so Deborah felt emboldened enough to peek her head around a little more, allowing herself a better view. She unconsciously bit her lip and furrowed her brow as she looked at her son's hands stroking up and down his long veiny shaft. Her eyes followed his hands on a downstroke and her hazelnut eyes widened again at her son's large sack. Shaking her head, Deborah tried to pull away, but couldn't; her stockinged feet were stuck in the carpet as if they had grown roots. Her eyes kept travelling back to her son's cock as portions of it disappeared beneath Jason's hands and fingers.

It wasn't until Jason started stroking faster and the "schlicking" sound from the lube become louder that Deborah realized her son was getting close to finishing. Knowing that lingering any longer was risky, Deborah stayed rooted to the spot, her eyes unblinking; she had to see the ending now that she had begun. Unconsciously rubbing her thighs together, Deborah didn't realize she was breathing heavier.

Suddenly, Jason spoke his first words since Deborah's arrival, and they blew his mother away. "Oohhhhh, Mom, just like that. Oh Mommmmmmm." Her son groaned as he thrust his hips up, his dick sliding through his slick hands as it erupted.

Deborah's mouth hung open as wide as her eyes while she watched her son's balls contract. Her gaze went up his throbbing shaft to see a huge white rope of spunk leave her son's swollen cock head, followed by another, and another, for a repeated six sticky ropes that ended up landing on top of her straining son with wet smacks. His load sounded HEAVY.

As he settled down and his ragged breathing started to slow, Deborah realized where she was, what her son had just done, and what she had done by watching him. Flushing again so deeply she could have sworn her hair blushed, she was finally able to rip herself away from her son's door and quickly scurry down the stairs, hopefully as silent as she had been on the way up.

Quickly ducking back outside, even forgetting her shoes in her haste, Deborah waited a full two minutes before pushing open the door and announcing herself for the second time that afternoon. Thankfully, Jason called down to her his usual greeting and the two managed a totally normal evening thereafter.

Ever since that day, Deborah had tried, and started to succeed, in ridding herself of that image. The guilt at having spied on her son as he masturbated had eaten at her and shamed her to the point where she had managed a semblance of peace within herself, the image of her son's beautiful big cock almost blocked and forgotten.

However, since seeing her boss Tim earlier that morning stroking himself off in such a similar manner, all the images of her son came rushing back in full force, if not stronger than before; as if her repression of the images had only fortified their importance.

With a shake of her head and a start, Deborah pulled herself together, banishing the image of her son's thick, cum spitting cock, and opened her car door. Briskly, all business in her strut, she walked up to her front door and let herself in. These were going to be a long three weeks of vacation to be sure she thought ruefully with a shake of her head... "Long indeed" she thought, not sure herself what she was referring to.

***

Jason walked home; his sneakers almost silent on the sidewalk as the few butterflies in his stomach did anxious flips. He didn't feel the normal Friday evening excitement for the coming weekend. He was too busy thinking about his mother, Deborah. Most boys didn't get anxious thinking about their mothers, and those who did usually did so for different reasons. Jason was nervous thinking about his mother because, well because he was really attracted to her. Not attracted to how good of a mother she was, which she assuredly was, but attracted to how unbelievably sexy he found her as a woman. He knew that it wasn't normal for a boy to be attracted to his mother, or at least, he thought he knew. He knew that taboo stuff was frowned upon, but then again, he also knew that... well, taboo stuff was pretty kinky, and there seemed to be a big audience for it.

Right then, he was debating with himself. He wasn't sure if he should risk masturbating with his door open again, or if he should just leave it alone. He could have sworn that he heard his mom at his door the last time he had done it. But then he had heard her open the front door a few minutes after his climax and he had been very confused. Maybe she had seen him and run, or maybe she hadn't seen him at all and would rip his head off if she found him jerking it so openly like that.

He really wished that he had never let his friend Jimmy convince him to masturbate where his mom could see. A few weeks ago, when Jason had confided in his best friend his... strange attraction to his own mother, he had been floored, and so had Jimmy, to find out that they shared the sentiment. Not both about Jason's mother! That would have led to a fight for sure, but to their own respective mothers.

What had floored Jason even more was when Jimmy had told him that his mom jerked him off! Jason had called Jimmy a liar flat out, thinking it some poor joke. But then, the look Jimmy had given Jason had given him pause. It was one of those, "I don't care if you believe me or not, actually I probably pity you if you don't believe me, because I know I am fucking right" kind of looks. And Jimmy RARELY had the confidence about anything to pull off that look convincingly; Jason had started to believe that just maybe his friend was telling the truth.

A few days, and many questions later, and Jason had actually been convinced that Jimmy's mom, the good old Pastor's wife, church going, bible-toting Mrs. Bywater, was jerking off her son on the regular. After his initial incredulity, Jason had to know how it had happened, and how it might potentially happen for him.

After some prompting, Jimmy had opened up to Jason about his relationship with his mom. He had been pretty hard to get answers from, seeming to guard information about his relationship with his mother as if that was somehow sharing her. Jason guessed it could also just be awkward telling your friend how your mother gave you handys after school like it was a normal thing.

Jason kicked a rock and watched as it bounced along the sidewalk, to hit a crack and veer off into the grass on someone's front lawn. Looking up at the house, Jason realized that it was Mr. and Mrs. Kim's house, the parents of one of his other friends, Sam. Shaking his head, Jason turned around, only now realizing that he had walked past his own house by a few blocks.

As he made his way back the way he had just come, he tried to tackle the issue by talking to himself; sometimes he found that it helped.

"Okay, let's make a list of pros vs. cons," He started. This was something his mom had taught him a long time ago to help him make decisions.

"Pros of jerking off with my bedroom door open for... for mom to see." He said, unconsciously blushing speaking out loud the taboo he was considering. "One: I get to jerk off like normal, but it's kind of a lot better... the thrill and all." He mumbled.

"Two: Maybe... Just maybe, Mom catches me and doesn't freak out." That one seemed more likely than he was admitting to himself. His mom rarely freaked out on him; she was usually always very understanding.

"Three: I don't know why she would... but apparently Mrs. Bywater does it soooooo... Maybe Mom decides to help me out and she jerks me off..." Jason swallowed as he realized that his dick was starting to swell in his shorts as he thought of his mom's hands wrapped around his dick. Fuck did his mom ever have pretty hands. She always kept her nails nice and manicured, and her hands were so soft whenever they touched him, a hell of a lot softer than his own.

Reaching down and adjusting his dick so that it was trapped under his waistband, making it less obvious, Jason kept walking, adding to his list. "And four: Once it happens, maybe I won't ever need to jerk myself off again..." He mused wistfully, his dick swelling some more as he let his imagination take him away.

He could just imagine the look on his mom's beautiful face as she pumped his dick in her hands, lube spilling out between her fingers as she stroked him. He could even see her breast jiggling contained as they were in her bra and professional blouse. He loved watching his mother's breasts bounce around in the clothes she wore; especially her office clothes. He tried imaging what his mother's tits would like bare, but he had never been lucky enough to see them in their full glory. Jimmy said that he saw his mom's tits all the time; Jason could admit to himself that that fact had him seething with jealousy, but he would never admit it to Jimmy; Jimmy liked to gloat a little too much sometimes.

Snapping out of his fantasy, Jason shook his head and went onto his next list, the cons. "Con number one: Mom catches me jerking off and... freaks the fuck out." He let out the words with a sigh. "Con number two: Maybe she stops talking to me, and maybe we don't hang out anymore." That one hit pretty hard, Jason felt his now flaccid dick slipping back into his shorts, its lack of rigidity making his pants unable to hold it up any longer.

Jason tried to come up with a con number three, but he couldn't see his mom doing anything too drastic like throw him out of the house just because he was jerking off carelessly.

Totaling up his lists, he saw that he had 4 pros and only two cons. Sure the list was pretty short, but double the pros vs. the cons was a pretty rare outcome. However, that second con was pretty fucking brutal. Jason and his mom had a great relationship, and he fucking loved his mom. Like maybe loved her a bit too much. He had always been a mama's boy, but recently, he had started to get butterflies in his stomach just being around her like he used to with girls he had crushes on. Talking with Jimmy certainly hadn't helped him much in that department. Jason really wanted to maybe see where things could go with his mom, but he didn't want to lose what they had right now.

Turning onto his street, Jason shook his head again. He was going to have to give this more thought he decided as he pulled out his housekeys.

***

Deborah turned in the mirror and checked herself out; she still had a few minutes before Jason got home and she wanted to make sure that what she was wearing wasn't too scandalous. She had on a pair of black yoga pants that hugged her wide motherly hips and long legs nicely. At 5'9, Deborah was kind of tall for a woman, but she was still shorter than her growing boy who was already 6'1.

Deborah pushed one foot up on her toes, arching her foot so that her bum looked better. She always had trouble getting into almost all kinds of pants. Ever since she had started to develop, Deborah had a big bum and shapely hips. But after giving birth to Jason, she had added a few pounds that never seemed to want to leave her butt and hips. Every day, Deborah had to wiggle into her pants, whether they were jeans, leggings, or even a skirt, she could never just slide her clothes past her bum; only sweatpants went on without a problem, and even then, the butt was often tight. Since she always filled out pants so nicely, Deborah always made sure that her panties were the invisible kind where the lines couldn't be seen through the cloth above.

Rubbing her hand over where she knew her panties ended, Deborah sighed and let the hand holding up her baggy T-shirt fall. She turned back so that she was facing the mirror dead on and looked at her chest. She was wearing an around the house casual summer T-shirt that she had left over from her previous marriage. It was a black Nirvana T-Shirt with the dead eyed yellow happy face, its tongue sticking out. She and her husband had been big fans, and even though that cheating dick was gone from her life, he couldn't spoil Kurt Cobain.

However, while she wouldn't have thought twice about wearing this around the house, she turned sideways and looked again to see if she could see her own nipples. Deborah had worn this shirt in front of her son countless times, but she had NEVER worn it without a bra underneath before. She, as a proper mother, ALWAYS wore bras when around her son. Deborah knew that some mothers didn't but she had always had very sensitive nipples that could be aroused by the slightest thing. And when she got aroused, her puffy nipples started to poke out and added the perfect point to her wonderfully sloped breasts.

Turning back again, she hefted her breasts in her hands, lifting their familiarly comfortable weight and squishing them through the soft fabric. She bit her lip involuntarily as she felt her nipples start to stiffen. With a shake of her head, she dropped her tits and appreciated the jiggle that followed as they settled back down on her chest. "All you've done is take off your bra Deborah, it's not like you're walking around with your tits out for the boy to see." She berated herself as she turned away from the mirror and picked her bra up off the floor; walking across her bedroom carpet she threw the piece of fabric into her laundry hamper. "Not like how he is walking around the house with that... thing out for me to see," she mumbled more quietly to herself.

Turning to look at her clock, Deborah frowned. It Read 03:37 PM. Normally Jason would have been home a few minutes ago. Walking out of her bedroom and down the stairs, Deborah blushed as she realized how much more her tits bounced without her bra to contain them. "Maybe I should get my bra..." She wondered before telling herself no, it was perfectly normal for a mother to go braless in front of her son. There was nothing to be ashamed about, so what if her breasts bounced, it was completely natural and something to be admired, not hidden and shamed.

That was what she told herself distractedly as she reached the front door and turned the handle, deciding she would see if her son was walking down the street.

***

Jason walked up the path to his front door, thoughts of his mom still in his mind, distracting him. As he reached for the handle, the door swung open, startling him. With a small jump, he almost ran into is mother.

Deborah pulled back with a squeak as she almost bumped into Jason, her hand reflexively coming up to her face in surprise. She covered her surprise, turning her squeak into a laugh as she let out a sigh. "Oh, you scared me honey," Deborah laughed, placing her palm on her chest as if calming her beating heart.

Jason looked at his mother, the surprise at reaching the door at the same time still on his face. However, as his mother laughed at their predicament, he couldn't stop his eyes from being drawn to her chest. Her breasts bounced in the most enticing way he had ever seen, and he had looked often recently. His mouth hanging halfway open, he brought his eyes quickly back up to his mother's soft brown gaze when she coughed lightly. He could have sworn she had a slight blush on her cheeks, a blush that must mirror his own hot face.

"Ummm. Sorry mom!" He rushed, "I took a wrong turn and had to backtrack. It made me a little late," he offered weakly, his steel grey gaze falling back to her chest in her favourite Nirvana T-shirt before quickly shooting back up to her eyes.

Deborah felt her heart flutter a little as her son dragged his wandering gaze back up to her eyes. She pretended not to notice, but her body absolutely noticed his look. She forced herself to focus on his words instead of his searing grey gaze. "You got lost?" She asked quizzically, tilting her head so that her lazy brown curls fell over her shoulder.

"Ummmm. Yea." Jason offered dumbly, making such a valiant effort to keep his eyes locked on to his mother's. "I had a lot on my mind walking home," he added after a second's hesitation.

"Well, the semester is almost done and you still have some exams to write," Deborah offered, not wanting to ask what had been distracting her son; afraid that he might have been distracted by what was clearly distracting him at the moment, yet also hoping that it might be the same thing. "My gosh what am I doing?" she thought to herself as she felt her tummy flutter. Wanting to end this slightly awkward interaction, Deborah pulled her son inside.