Jacob's Confidence

Jacob Turner was like many young men of his age in that he had no faith in himself to seduce the opposite sex. He had never been on a date with a girl, nor did he possess any sexual experience. He was a high school senior, an eighteen year-old virgin, and lacked any confidence in his ability to acquire sex. The problem wasn't physical. Jacob wasn't ugly, or fat. He didn't have acne problems, or bad hygiene. His difficulties were social. Jacob was a shy and reserved young man who had trouble even talking to girls; he had no idea what to say or do in order to attract them, so he simply quit trying.

Jacob was the son of a single mother and lacked a strong male role model his entire life. This made him more sensitive than macho, more intellectual than athletic. He enjoyed comic books and games, reading and movies -- mostly solitary activities. He would rather watch Game of Thrones than a football game, or play Dungeons & Dragons rather than go to the park and shoot hoops. Jacob was fully self-aware his interests were geeky and completely outside the realm of what most girls were into, which only deteriorated his confidence in ever gaining a girlfriend.

And like many men his age, Jacob was always horny.

He thought of sex constantly, both his desire to have some and his inability to get any. In order to alleviate the constant urges, Jacob turned to masturbation. He masturbated a lot. A typical day in Jacob's life consisted of three or four sessions. He would masturbate in the morning before school, usually in the shower or bathroom. He would masturbate after school, before his mom got home from work. He would masturbate in the evening after supper, and once again before going to sleep. That last session late at night was always the best. Jacob would confine himself to his room, quietly lock the door, and take his time while watching pornography on the computer, confident his mother was asleep downstairs - completely unaware of his habits.

Jennifer Turner was a wonderful mother who devoted herself for eighteen years to raising her son. She was thirty-eight years-old, having given birth to Jacob when she was twenty. Jacob's father was never in the picture, he was a cowardly man who was scared of being a parent and disappeared before Jennifer was six months pregnant. The two never married; she raised her son alone.

As a career nurse Jennifer had provided her son with a stable, middle-class upbringing in a modest house within a safe suburban neighborhood of Phoenix, Arizona. She worked five days a week and always came home to make sure she and her son could have supper together. Jennifer helped Jacob with his homework, made him do chores, and tried to invest in him the morals needed to be a good, upstanding person. Jennifer adored her son and encouraged him often, advising him to pursue his interests whatever they may be. She was proud of the fact that he was a handsome young man who didn't do drugs, didn't get into trouble, and always received good grades at school. She was looking forward to his acceptance to a college or university, as it was the spring following his eighteenth birthday and classes would begin that fall.

But she was also concerned for him. Jennifer was well-aware her son wasn't involved with any females; Jacob never once brought a girl home to meet his mother. Instead of going out on dates, Jacob would hang-out with his male friends to play video games or watch movies with superheroes in them. She also knew he was masturbating a lot; it was obvious from the sticky messes Jacob had started leaving in his socks and towels. She worried he might be gay or struggling with confusion over his sexuality. Not that Jennifer would love her son any less if he was homosexual, she would support him no matter what, but she didn't want him to be alone or confused with no one to help him understand things young adults often struggled with.

She resolved herself to find out. Jennifer decided to confront her son as gently as she could. Maybe he was gay, maybe he was simply a late bloomer, but Jennifer loved him more than anything and thought she might be able to help him in some way if the two could talk about it.

Their home was a split-level house and Jacob's room was on the upper floor, down a short hallway with a bathroom and another spare bedroom. When Jennifer approached his bedroom door it was just after 10:30pm and she heard her son's voice, pausing her fist in mid-air instead of knocking.

"...Mommy... oh, Mommy, you're so hot..."

Jennifer's expression bulged with surprise at what she heard. Instead of disturbing him, she silently leaned closer to the door. Jacob's heavy breathing came from the other side, low moans mixing with the slick sounds of lubricated self-pleasure. He was masturbating!

"...uhhh... so sexy... uhn!... uhn!... oh, Mommy..."

Oh my god! Jennifer thought, covering her mouth with a palm to keep from gasping. Was he fantasizing about her? Unwilling to interrupt and embarrass him, Jennifer hurried away as quietly as she could to her downstairs bedroom. The conversation she had planned would have to wait for another time, it would have been uncomfortable enough even without mixing in the topic of his masturbation.

Jennifer changed and crawled into her bed. She lay in the dark, her eyes wide open. Was Jacob really thinking about her when he was masturbating? Was that even possible? Was that normal? Many questions swirled in her mind and she wanted answers. But how could she get them? Jennifer worried that if she confronted Jacob about what she heard, it would certainly humiliate him and possibly drive a wedge between the two. She would have to find another way - the close relationship Jennifer held with her son was too important to risk.

Sleep came with difficulty and the following morning Jennifer's mind remained pre-occupied by what she heard through her son's bedroom door. As she was doing her best to stick to a daily routine and prepare some breakfast, she heard Jacob's morning alarm. Barely a minute later she listened to him enter the upstairs bathroom and start a shower.

Sensing an opportunity, she rushed upstairs, entered Jacob's room, and sat at his desk. She wriggled his laptop mouse and watched as the screen flashed to life. He hadn't turned it off or locked it, thankfully, and she was able to open a web browser. Jennifer felt guilty for snooping, but curiosity got the better of her. She opened the browser's history and saw the last page Jacob had been looking at -- a Facebook address. Clicking the mouse on the link, Jennifer's face twisted in confusion as a sub-directory of her own Facebook page loaded. It was a picture gallery from the vacation she and Jacob had taken to Florida only two weeks prior. The browser's memory automatically enlarged the last picture Jacob had been looking at and Jennifer's eyes went wide with shock. It was a picture of her, on the beach at their hotel, in a bikini.

He was looking at me, her mind screamed, my son was masturbating while looking at me!

Quickly closing the browser and pushing the computer's sleep button, Jennifer hurried out of her son's room and returned downstairs to the main floor kitchen. A mixture of confusion, worry, and flattery swirled through her emotions as she finished breakfast. "Well," she whispered to herself, "At least I know he's not gay."

=======

Jennifer had trouble concentrating on her hospital duties that morning as thoughts of Jacob's masturbation dominated her mind. During lunch break she sat alone in the hospital's cafeteria, setting her phone on the table beside a tray of food. Jennifer ate with one hand and typed into Google with the other. She found a psychological article about the habits of male masturbation and found it was not uncommon for men to fantasize sexually about their mothers. Unfortunately the article didn't offer any advice to mothers about what to actually do when catching their sons masturbating to such fantasies, nor did any other articles she browsed. What Jennifer did find was plenty of pornographic links to sites that advertised incestuous videos between mothers and sons and wondered if Jacob ever watched such things on his computer. Of course he does, she thought, he's an eighteen year-old with raging hormones.

Images of her son sitting at his computer desk, his erection in a pumping hand, viewing pictures of her while moaning 'mommy... mommy' entered Jennifer's mind and she felt a tingle between her legs. The sensation of arousal made her feel immediately guilty and she quickly turned off her phone's screen and pushed the thoughts from her mind. Jennifer forced herself to think about work for the remainder of her lunch break, but not without difficulty.

Jennifer was still a relatively young woman, after all, at thirty-eight years-old, with sexual desires and fantasies of her own - most of them long-denied from a lack of men in her life. Raising a son on her own, working a full-time job, and always being home in time to make dinner and help Jacob with his homework meant Jennifer had sacrificed a personal life. She also didn't want Jacob exposed to different men or becoming confused by her having boyfriends that ultimately may not develop into a long-term relationship, so Jennifer had avoided dating all-together. She told herself that such things could wait until he was gone to college. So, like her son, she satisfied her sexual desires through masturbation. She did it far less frequently than he did, of course, and was able to be more discreet about it, but she still viewed herself as a very sexual woman.

It was mid-afternoon when Jennifer was treating a patient not much older than Jacob. The poor man had recently undergone major abdominal surgery and needed help going to the bathroom. Jennifer helped him to the edge of the bed, dismissing and soothing his embarrassment as she held a basin for him to urinate in. But when Jennifer saw his penis, the thoughts of Jacob masturbating flooded back into her mind and remained there for the rest of her work day.

As she drove home from the hospital, her panties grew damp as Jennifer once again imagined Jacob in the throes of pleasure while looking at her on his computer, picturing his hand as a pumping blur. She could hear him, just as she heard him through his bedroom door the night prior, moaning 'mommy... mommy'. The idea of a virile, younger man finding her so attractive that he was forced to pleasure himself flattered and excited Jennifer, even though that man happened to be her son. She wondered how often he enjoyed that particular fantasy. And what did he think about? Was he imagining sexual intercourse with her? Jennifer shuddered at the sudden thought of Jacob between her legs, his erection penetrating her.

What are you thinking, her mind reeled, how can you think about your own son that way?

=======

"How as school today?" Jennifer asked as she and Jacob sat at a small kitchen table, enjoying dinner. She had made spaghetti and was twirling some onto a fork.

"It was okay," Jacob shrugged, "I think I did okay on my algebra quiz. How about you, how was work?"

"Oh, you know," Jennifer hid the fact that her day had been anything but typical, "Same-old-same-old."

As they continued to eat, Jennifer regarded her son fondly. Jacob was so cute with his neatly-trimmed brownish-blonde hair, cropped short at the sides and tousled on the top. He had large brown eyes and two adorable dimples in his cheeks when he smiled. He had a slender frame, Jacob was still skinny and coltish with growth, but he had broad shoulders and was starting to develop into his manly frame. He was tall at 6'1", far taller than Jennifer. He was sweet, he was beautiful, and he was her son. Jennifer loved him more than anything else in the world.

She started wondering if he had ever kissed a girl and imagined being in his arms...

"Mom?"

"Huh?" Jennifer was distracted from her fantasy.

"Why are you looking at me like that?" Jacob was staring at her.

"I'm sorry," Jennifer tried to hide her blush with a smile, "I was just thinking about how much I love you and how proud I am of you. Soon you'll be off to college... you're a man now."

"Mo-om," Jacob grinned embarrassedly. He had finished eating and began to gather his plate.

"Don't worry about the dishes," Jennifer reached and placed a hand on his arm, "I'll take care of them tonight."

"You sure?" Jacob wondered.

Jennifer nodded.

"Thanks, Mom." Jacob stood and then bent to kiss her cheek before heading upstairs to his room.

Jennifer smiled at him. Her cheek tingled where she had felt Jacob's lips.

The rest of the evening passed quickly. Jennifer did the dishes, some house cleaning, and ironing, finally settling into bed to watch the late evening news. But her thoughts were never far from Jacob. When the news was over it was 10:30pm - the same time it had been the night prior when she heard Jacob masturbating.

Turning off the television with a click of a remote, she couldn't help but wonder what Jacob was doing upstairs in his room at that moment. She didn't want to spy or violate his privacy, but once again curiosity got the better of her. Climbing out of bed, Jennifer slipped a robe on over her nightie and padded as quietly as she could in bare feet up two flights of stairs to the upper level.

Jennifer held her breath as she approached Jacob's bedroom door, both out of excited anticipation and the desire to be quiet. A sound from his door handle startled her and for a brief instant Jennifer feared Jacob was about to open the door and catch her snooping, but then she realized he had simply locked the handle. She snuck a bit closer to listen and was rewarded a few moments later to the sound of a video coming from his computer. A pornographic video.

The pleasurable moans of a female were obvious and Jennifer wondered what sort of sex scene her son was watching. Fapping sounds started and it took a few seconds for Jennifer to discern that the noises were the sounds of Jacob stroking his cock. He was masturbating. He was masturbating vigorously!

"Oh my god," Jennifer whispered, her voice barely audible. She leaned against the wall next to the door jamb and continued to listen, imagining her son furiously pumping his hard erection.

Several minutes passed and suddenly the video stopped, replaced by the sounds of Jacob briefly typing. Jennifer heard her son moan in pleasure and the fapping sounds became louder. "Mommy," his voice came through the door, "I want you so bad, Mommy..."

Jennifer's heart pounded in excitement. Without thinking about what she was doing Jennifer hiked the hem of her robe up, allowing her other hand to slide beneath her nightie.

Jacob continued to talk in low murmurs, "...so sexy... want to touch you... rub you all over... oh, Mommy... want to cum on you..."

Jennifer shuddered and felt her legs go weak as she leaned against the wall and masturbated herself.

"Uhh... uhn... Mommy... I'm gonna cum... oh god...UHH! UHNNNN!"

She listened to her son stroke himself to climax and imagined the semen ejecting from his cock. Jennifer winced and her expression twisted with pleasure as a sudden orgasm ignited between her legs, a fast burn that took her by complete surprise. She had to bite her lip to prevent herself from crying out as the warmth flooded through her thighs and abdomen. Barely able to stand, Jennifer was thankful the wall had been there for support.

Then there was nothing, no sound. Jennifer worried that Jacob had somehow heard her despite her attempt at silence. She hurried away from his door as fast as she was able without making any noise, her bare feet trotting down the carpeted steps towards her room. She shut the bedroom door and finally allowed herself to breathe, her heart drumming within her chest. Jennifer was flush from her orgasm and her mind was reeling from what she heard and experienced.

Her own son had a crush on her; that much was obvious. A naughty crush that was full of lust and vivid sexual fantasy. Jennifer didn't know how to react. Her rational side told her it was wrong, but her passionate side was flattered and wanted to explore the idea further.

No, she suddenly thought, such a thing isn't possible. It's incest! Jennifer remembered what she had read earlier that day, how it was normal for Jacob to have his fantasies. They were harmless -- a person shouldn't be condemned for solitary fantasies they enjoy in privacy. There was nothing wrong with what Jacob was doing and there was nothing out of the ordinary about him masturbating, even if his fantasies were a bit incestuous. She was the one crossing the line for thinking it could ever involve her directly.

Still, Jennifer longed to see him do it. She wanted to watch Jacob jerk-off and cum while looking at her. She couldn't help it. She wondered what his penis looked like and how much semen came out when he thought of her. It was all so carnal, tantalizing, and arousing that Jennifer couldn't help but to masturbate herself to sleep that night.

=======

A week passed and Jennifer did her best to control her fantasies. She was determined to let the matter drop and refused to continue spying on her son, despite any further curiosity. Jacob would eventually move past his crush, Jennifer reasoned, and he would go off to college, find a girlfriend, and his crush would become a distant memory. At least, that's what Jennifer kept trying to convince herself of. But as the week wore down, so did her resolve. She wanted to tease him, to fuel his desires. If Jacob wanted to look at her, Jennifer wanted to give him something to see. Giving her son something to look at was harmless, right?

It was Saturday when Jacob was in his room with his best friend, Matt -- a fellow eighteen year-old senior.They were playing video games on Jacob's PlayStation when Matt rose from the floor to stretch.

"You need another soda?" Jacob asked.

"Nah," Matt lifted his arms and puffed out his chest as he worked the kinks out. He casually glanced out Jacob's bedroom window, which had a view of the back yard. Matt was treated to a sight that made his eyes widen. "Holy shit!"

Jacob glanced at him, "What?"

Laying on the back patio on a folding lounge chair was Jennifer, clad in a blue floral print bikini and sunning herself under the warm spring day. Though she was thirty-eight years-old, Jennifer had maintained her figure through the years and still had a body that made Matt gaze with desire. Her shoulder-length, dark blonde hair was splayed around her head and she had on a pair of large sunglasses.

"Is that your mom?" Matt stared out the window, pushing the frames of his glasses up the bridge of his nose.

Jacob quickly rose from the floor to see what Matt was ogling.

"I always knew your mom was pretty, but damn!"

Jacob elbowed his friend, "Dude, that's my mom."

"Yeah," Matt nodded, "Your mom is hot."

Jacob wanted to protest further but his own gaze lingered on his mother's shapely frame. He stared at her toned legs, rounded hips, and her c-cup breasts that were barely contained by the thin triangles of a bikini top.

"I'd like to squirt-out some suntan lotion for her," Matt joked crudely, "If you know what I mean."

"What?" Jacob was distracted from similar thoughts, "Aw, man. That's gross. That's my mom you're talking about."

"Whatever," Matt sighed, "I need to get going, anyway. I'm supposed to help my mom shop for my sister's birthday present. You want to hang-out tomorrow, maybe go to the honbby shop?"

"Yeah," Jacob reached to turn off his PlayStation, "That's sounds cool."

"Okay, man. See you later. Say 'hi' to your mom for me," Matt grinned and saw himself out.