Dating Mom

First Edition

2026

 

Published by Sinful Lust Publishing

 

Dating Mom

 

Two years have passed since Jake Harlan's father died. Jake was sixteen when the tragedy occurred. While Jake missed his dad a lot, it was no more than his mom did. Their life had been ideal—living in the suburbs, with a two-car garage and excellent schools. Everything was just about perfect until the accident.

David Harlan had been driving home from work late one night when a drunken driver crossed the centerline and hit his car head-on. He was unable to escape the situation. The police said that the other car had been traveling at almost one hundred miles per hour.

The funeral was difficult for everyone. David and Elena's relatives flew in from around the country and were an enormous help to Jake and his mother. However, when the funeral was over, she and Jake had to go home and deal with the loss alone. The accident changed their lives dramatically.

Jake's mom, Elena, had to go back to work to make ends meet, and they had to sell their house. However, in the two years since David's death, Elena has done very well in her job, and she has been lucky in the stock market. She had purchased a new house for her and Jake, smaller than before, but very comfortable nonetheless. The job and investments provided enough money to enjoy life and take an occasional vacation.

While the two years since the accident had been financially stable, it was emotionally difficult. On an emotional level, she and Jake were still struggling. They leaned on each other for support and therefore had grown closer than the typical mother and teenaged son.

Jake Harlan became the man of the house overnight, but he knew that he couldn't make up for the loss of his dad to his mother.

Jake was a tall, handsome, and lean boy at 6' 1" and 175 pounds. He was bigger than most of his classmates. However, while he appeared to be a confident teenager, he was, in fact, very shy and overly sensitive. Although he had his dad's handsome face and the bright blue eyes of his mom, he wasn't comfortable with girls.

Jake wanted to date, but every time he was around an attractive girl, he would become tongue-tied and embarrass himself. It was easier for him just to avoid those situations. Besides, he almost felt like he would be cheating his mom if he dated.

Now 18, Jake had graduated from high school with honors and had earned a football scholarship to a local university. While he looked like the All-American boy, he had never had a girlfriend. His shyness was an incredible embarrassment for him. The shyness was primarily the result of a slight stutter that he had developed not long after his father died. He had hid it successfully from his mother so far, and most of the time he could cover it up. However, it tended to show up when he was nervous, and all too often, that was in the presence of girls his age.

Elena Harlan was still a very attractive woman as well. She was tall at 5' 7" with a well-proportioned body. However, like most women, she was critical of her body. She thought that her butt was too round and that her breasts were too large. Her tendency was to dress on the conservative side to cover up her perceived flaws.

Elena had been desperately lonely since David's death. Although she tried not to lean on Jake too much, he seemed to be the only one that really understood. She didn't have to explain to him how she felt when she was sad, angry, or lonely. He just knew. Elena thought that she could read Jake as well.

Out of sheer loneliness, Elena had tried dating. Unfortunately, she hadn't met anyone that she really liked or connected with on an emotional level or, for that matter, on a physical level. Elena still had strong sexual desires. However, she needed more from a man. She needed tenderness and understanding first. Most of the men she dated seemed to think that because she was a young widowed woman, she would jump into bed at the drop of a hat.

Jake tried to encourage her to go out and have some fun, but whenever he suggested that she find someone, she would always tell him that he was the only man she needed in her life now. It was almost as if she would be cheating Jake or somehow hurting David's memory. While she knew deep inside it was time to move on, she couldn't let go of the past.

Now 36, Elena worked hard to keep the family financially solvent. Her job as a public relations executive was rewarding but time-consuming. She had to work 12-hour days and sometimes Saturdays.

Jake talked her into wearing sexier clothes and had even convinced her that she looked great with short skirts and low-cut tops. He told her that she needed to show off her assets to get ahead in business. It had worked on the business level. However, her good looks also attracted a lot of unwanted attention from men.

Whenever Jake would tell her that she should date, she would turn his comments around and say he should be the one dating.

Elena was more concerned about her son's lack of social development than she was about dating herself. She wanted him to go out and have fun, yet he would be home most weekend nights with her.

One Saturday evening, Elena found Jake sitting in the living room watching TV as usual.

"Jake, why are you sitting home tonight? Why don't you go out with someone?" Elena said, sitting down next to her son and putting her arm around his shoulders. They had this conversation almost every weekend.

"Come on, Mom, give me a break. I don't need to go out; besides, I'd rather be home with you." That had been his standard response. It was a lame excuse, and they both knew it.

"Jake, you need to have friends, you know... girlfriends," Elena said in exasperation. Then she looked at him seriously and said, "I'm worried about you."

"You seem to do okay without boyfriends. Why do I need girlfriends?"

"Come on, Jake, that's different, and you know it. I've already been married. Besides, I already have a man. You!" Elena said, squeezing his shoulder affectionately.

"Well, I have plenty time to date. Besides, I already have a woman. You!" Jake replied, smiling at using his mom's own words.

Elena sighed in frustration. "Well, we're a fine pair, aren't we?"

"Mom, you're my best friend," Jake said seriously, snuggling into her arm.

"And you're my best friend too," Elena said, hugging him again. However, she couldn't let it go. "You still need to date. It's not healthy."

Jake took a deep breath. "Mom..."

"What?"

Jake's mouth was opened, but nothing came out. His head fell back on the sofa, and he closed his eyes. His face seemed to color in embarrassment. "It's nothing. Never mind," he finally said.

"Come on, Jake... please don't close me out," Elena said, turning his face to her and looking into his misty eyes. "We've always been able to talk about anything. Haven't we?"

Jake had wanted to talk to his mother for a long time about his shyness and the stutter, but he didn't want to burden her. Additionally, he felt embarrassed talking to her about girls. Now that he had finally gotten up enough nerve to bring the subject up, he knew he had to continue. "It's... it's just that I'm... I'm not so hot with the girls. I'm too shy, and whenever I get around a nice-looking girl, I... I... I... get tongue-tied," Jake said, his eyes unable to meet his mother's.

Elena was surprised but tried not to show it. She had never heard him get tongue-tied before. "Now wait a minute; you always say that I'm a nice-looking girl, and you don't get tongue-tied around me."

"I'm serious, Mom. I don't know what to do or say around girls. I've only kissed two girls in my whole life," Jake blurted before he could stop himself.

"Really?" Elena said in astonishment. My God, he was 18 and he had only kissed two girls, she thought. He must be a virgin! The realization shocked Elena. Then a bigger problem occurred to her. "You like girls, don't you?"

"Mommmmmm! Of course I like girls," Jake said, now totally embarrassed.

Elena sighed in relief.

"It's just that... just that... oh hell... I haven't even been on a real date."

"Wow, Jake, I had no idea!" Elena was unable to hide the shock in her voice. "I've seen you go out. You said you were going out with girls."

"I'm sorry, Mom, I lied. I go to the library or the mall. I just didn't want you to feel bad for me. You have enough on your mind."

Suddenly, Elena realized that she had neglected Jake since his father died. She had been foolish to think that she could read him. She had been so busy mourning her own loss, feeling sorry for herself and working on her career that she had missed all the signs. It was obvious now that he was very sexually immature. God, how could I have been so stupid? she thought.

The two of them sat silently for a long time. Neither one of them knew what to say.

Finally, Elena broke the ice with an idea.

"Jake, what would you think about you and I going on a date?"

"Come on, Mom! Get serious!"

"I am serious. You're very comfortable around me, so why don't we go out? You can act as if I'm your date. I can tell you what you need to work on. After all, I still remember what girls like." Elena stopped when she realized that he might be embarrassed to go out with his mother. "Uh...that is if you wouldn't be too embarrassed to be seen out with your old mom."

"God, Mom, you're not old. You're the best looking woman I know!" His face turned red as soon as he said it.

"Thank you, sweetheart, and you are the best-looking man I know. So why don't we two good-looking people go on a date?"

Jake was quiet for a few minutes, thinking. Maybe it would be good for her to go out, he thought. Besides, she might get off his back about dating. It could be a way for him to help her. Suddenly, he liked the idea. "Well... okay... I guess it might be fun," Jake finally said in a nonchalant tone.

"You don't sound that excited," Elena said with a pout.

"That's not it," Jake said quickly. But... but...

"What's wrong, sweetie?"

"I don't... uh, don't know about that stuff. I... I... I... would... uh... you know, feel silly if I messed up. That would be embarrassing," Jake said, a stutter in his voice.

"There's nothing you could do to embarrass yourself, honey," Elena said, patting his leg affectionately. "Come on, let's get dressed, and you can take me to dinner and a movie," Elena said, reaching to the table and picking up her car keys and flipping them to him. "You can even drive, lover boy."

"Mommmmm," Jake said, his face turning red again. However, underneath the embarrassment he was as excited as he had been in a long time.

Twenty minutes later, Jake was pacing around the living room nervously, waiting for his mom. When he saw her come down the stairs, he started to say something but stopped in mid-sentence with his mouth open.

Elena had on a tight, white pull-over top that was low-cut, exposing the upper swells of her breasts, and a short black skirt and high heels. She thought Jake would like the outfit since he picked it out for her.

"What's wrong?" Elena asked, concerned about the look on her son's face. Suddenly, she thought that she had made a big mistake.

"Mom, uh, uh, you look, look..." Jake stuttered, trying to tell her how great she looked.

"I'll change," Elena said, turning to go back upstairs, fearing that she had gone too far in trying to look young and "hot."

"No! You look beautiful," Jake blurted out.

Elena turned back around smiling. "Why, thank you, sweetie; I thought you were upset with what I was wearing."

"Wow, Mom, I hope some of my friends see me with you. God, they will be so jealous!"

Elena felt her heart swell with pride and love. "Well, let's go make them jealous. For tonight, why don't you call me Elena?" she said with a smile.

"Okay, Mo... uh, Elena," Jake answered. "Elena," he said again to himself, loving the way her name rolled off his tongue.

Jake rushed to the car in front of his mom to open the door to let her in. As she sat down, Jake couldn't help look at the expanse of her thighs as her skirt pulled up. When he looked up, he saw his mom smiling at him. God, she saw me looking up her skirt, Jake thought. "I can't even do that right," he thought, mentally chastising himself.

As he drove, Jake kept glancing over at his mother's legs. He felt a stirring between his legs and was suddenly very confused.

Elena's skirt had pulled up her legs, revealing her tanned thighs. She tried to pull it down, but the bucket seats of her car made that difficult.

Jake drove to a small Italian restaurant that they went to on occasion. It was quiet and intimate with a genuine Mediterranean look. The tables were covered in red checked tablecloths, and each had an old wine bottle in the center with a lit candle. There was even a violinist playing music.

Dinner went great and was very relaxing. Elena even let Jake have a couple glasses of wine. Elena wanted to make him feel more grown up. He certainly needed some confidence building.

Elena had quite a bit more wine than Jake. She felt a little tipsy but also warm and relaxed.

Jake had no trouble talking to his mom. The wine had loosened his tongue just a bit. Besides, it wasn't like it was a real date, he thought.

They talked about school, friends, music, and movies—all the things that a boy and girl would talk about on a date. Occasionally, Elena would point out things about how he should act on a date. Like waiting until his date had taken her seat before he sat down or opening the restaurant door for her. She tried not to be too critical. Not surprisingly, though, Jake didn't need much coaching. He was a natural gentleman, like his dad.

For a little while, Jake truly forgot that Elena was his mom.

Elena also forgot for a short time that she was out with her son. He suddenly seemed so mature. His pretty blue eyes sparkled in the dim candlelight as he laughed and his face lit up like a candle when he smiled. God, he was handsome, she thought. Suddenly, Elena felt a little shiver run through her.

When dinner was over, Jake escorted Elena out to the car, opening the restaurant door and hurrying to open the car door.

Elena was just a bit unsteady on her feet. She knew that she shouldn't have had that last glass of wine.

When Jake opened the door of the car, and his mom slid in, he tried not to look at her exposed thighs again. However, that was impossible. No matter how hard he tried, his eyes went to the dark area between his mother's legs. The light from a street lamp melted the shadows, and Jake drew in his breath. His mother's legs opened, revealing the silky tops of her thigh-high nylons, her smooth thighs, and then a pair of pale blue silk panties hugging the pouch of her sex. She paused for a second with one leg out of the car.

Jake stood almost frozen, his eyes as large as saucers.

"Well, are we going to the movies or not?" Elena asked, again noticing that her son was looking up her skirt. Another shiver ran through her. Now Elena wasn't sure whether the spreading of her thighs had been an accident on her part or not. She felt so naughty tonight. It was just a little innocent fun, she told herself. The wine was making everything seem all right.

Jake's shocked face turned scarlet when he saw his mom watching him again. Suddenly, he felt ashamed of his behavior. If I do this to my own mom, what will I do when I go out on a date with a real girlfriend? he thought.

At the movie theater they got sodas and popcorn and then found a seat near the back row. Since the movie had been out for a while, the theater wasn't crowded. They practically had the theater to themselves.

The movie was funny and light, making them both laugh. About midway through the movie, Jake carefully raised his arm and put it on the back of the seat behind his mother, his bare arm touching her shoulders.

Elena didn't miss the move and felt another of those little shivers come over her.

At one point when they were laughing, Jake moved his arm until it was around her, his hand hanging over her shoulder. His mom surprised him by sighing and snuggled even closer into his arm.

Elena smiled to herself at her son's boldness. She felt so comfortable and loved at that moment. It had been a long time since she felt like this.

Suddenly, Jake realized that his fingers were touching the top swell of his mom's breast where