Mom & Son's Valentine's Day Sex Ch. 01

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Son celebrates Valentine's Day with best friend, his mother.
14.3k words
4.28
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Part 1 of the 9 part series

Updated 06/08/2023
Created 11/17/2017
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There are no characters under the age of 18-years-old in this story.

Mom & Son's Valentine's Day Sex #01

Author's Note:

Based on a true story, this is a mother and son Happy Valentine's Day story of love, romance, compassion, and understanding with lots of forbidden, incestuous sex.

Michael, 24-years-old, is in love with his 48-year-old, best friend, Kimberly. He looks forward to celebrating Valentine's Day with her, the woman of his dreams, his soulmate, his lover, the love of his life, and his mother.

* * * * *

"Happy Valentine's Day, Kimberly," said Michael beaming by her loveliness. 'With her hair perfectly coiffed and her makeup perfectly applied and making her look like a CoverGirl model, she looked so pretty,' he thought before thinking that he should tell her that. "You look so pretty," he said an understatement to how he truly felt about her appearance.

Forget about her being pretty, if she was anything, she was beautiful. With him blinded by sexual lust and incestuous love, as far as he was concerned she was the most beautiful woman in the world. Perhaps, because she was his mother in addition to being a beautiful woman was why he was so blinded by her beauty.

Always respectfully formal of her before, with her a much older woman and with him a much younger man, this was his first time calling her by her first name. Instead of calling her Mom or Mother, it felt odd to say her first name aloud but she insisted that he did and she looked pleased that he was so familiar with her to call her by her first name. He hoped that by the end of this night that he'd be calling her more than Kim or Kimberly. He hoped he'd be calling her his lover.

Their first time hopefully being intimately together, their first time hopefully having sex, he was nervously excited with sexual anticipation. Yet, somehow and a good sign, as if she already knew his sexual intentions, encouraging him, she gave him a soft smile and a come hither look on this day of love, romance, and sex, Valentine's Day. Seemingly, his time to make his move, she sexually wanted him as much as he sexually wanted her.

'I love you, Kimberly,' he thought and wanted to confess but too much too soon, he dared not say how he truly felt about her for fear that she'd reject him.

The last thing that he wanted was for her to reject his sexual advances. The last thing that he wanted was to make her uncomfortable by his sexual forwardness. The last thing he wanted to do was to ruin the close mother and son relationship that they both enjoyed. He needed to take it slow. Hopefully, if she made the first sexual move, he'd make all of the other sexual moves.

Even though he was sexually excited to hopefully have sex with her for the first time, he was already feeling remorsefully guilty to dare put the sexual moves on her of all women, his mother. She was his best friend, his most trusted confidant, and the woman who he told everything to but for telling her that he loved her, needed her, and wanted to have sex with her. Sexually lusting over her from afar, whenever he was in his room and stroking his cock, he always imagined his mother in her bra and panties, topless, and/or naked. Every time he masturbated, he imagined having sex with her.

She was not only his favorite masturbation subject but also, she was his only masturbation subject. After giving him so very many deliberate or unintentional up-skirt peeks of her white, bikini panties and down-blouse views of her cleavage and low-cut bra, when he wasn't with her, he masturbated over imagining being with her sexually. The thought that he may have a chance of having sex with her tonight was what he had always hoped would happen.

'This is it. This is the night that I make my sexual move to seduce my Mom,' he thought while hoping that he'd finally get to have sex with her.

As a son would tell his mother than he loved her, he told her he loved her many times before, of course, but not like this, never like this, not romantically and surely not sexually. She may be shocked to learn that he loved her not only as a son and not only as a friend but also as a potential lover. She may be shocked to learn that he sexually wanted her, just as he may be disappointed to know that she may not sexually want him. Yet, tired of carrying a torch for her heart, tired of being horny and sexually frustrated, he needed to know one way or the other if she felt the same way about him.

'Mom? I love you and I want to have sex with you,' he imagined saying to her. 'Mom, I want to make love to you. I want to finger your pussy while licking your pussy. I want you to stroke my cock while sucking my cock. After I make love to you, I want to fuck you,' he thought whenever thinking of having sex with his mother.

Suddenly nervous and questioning his own intentions, he felt the way a man must feel when down on one knee, holding up the ring, and asking a woman to marry him. He felt the way a man must feel when waiting for the woman he just proposed to give her answer. Taking the chance to tell her how he felt on this special day or love, romance, and hopefully sex, Valentine's Day, a mother's intuition, she looked at him as if she already knew his intentions.

Yet, different from other couples, even though he loved her, he didn't want to marry her. He just wanted to have incestuous sex with her. He just wanted to make love to her before fucking her. The last thing he wanted to do was to insult her or offend her by her thinking that he only wanted her for sex. Just as he hoped she'd accept him as her lover, he hoped she wouldn't reject him.

In the way that he was sexually attracted to any woman, he wanted her for more than just sex. He wanted her for romantic love. Yet, he'd willingly finger and lick her pussy to orgasmic pleasure if only she'd suck his cock and allow him to ejaculate his cum in her mouth. If there was one woman that he was dying to have sex with, it was Kimberly, his best friend, and his MILF of a mother.

'I love you, Mom,' he thought.

Hard to read her, perhaps because she was his best friend and not his lover, risking their friendship, he was taking a big chance in soliciting her for sex. Hoping he hadn't misread her sexual signals, he hoped she sexually wanted him in the same way that he sexually wanted her. He'd love nothing more than to take their friendship to the next level. He'd love nothing more than to be sexually intimate with her. He'd love nothing more than to see her in her bra and panties, topless, and/or naked.

'She loves me. She loves me not,' he thought. 'Perhaps, she loves me only as her son. Perhaps, she loves me only as a friend and not as a lover. Perhaps, she wants to have sex with me. Perhaps, she doesn't want to have sex with me. Even though it's obvious that she loves me as her son and as a friend, her best friend, perhaps, she'd never have sex with me,' he thought while wondering what her reaction would be to him soliciting her for sex. 'Perhaps, jeopardizing their friendship and close relationship, she'd be deeply offended and devastatingly hurt that I dared solicit her for sex.'

He hoped that he didn't ruin the close connection and the deep attachment they enjoyed by asking her for sex. As much as he'd be hugely disappointed if she refused to have sex with him, he'd be heartbroken if she sexually rejected him. Yet, even worse than that, he'd never forgive himself if he was to blame for ending their friendship. He'd be crushed if she didn't want anything to do with him ever again. Taking a chance, with it well worth the risk, he persevered in revealing his sexual attraction to his mother.

"Thank you," she said when he said she looked pretty. "Happy Valentine's Day, Michael," she said.

* * * * *

She usually called him Mike instead of Michael but not on this day of love, sex, and romance. Instead of calling him by his childhood name, she called him by his man's name. Perhaps, a good sign, he hoped her calling him Michael instead of Mike was encouraging. Now that he was older and more mature, he preferred her calling him Michael instead of Mike or Mikey. When she called him Michael, he felt more like a mature adult.

As if he had just met her instead of having known her all his life, now that he had sex and the image of her naked on his horny mind, he felt awkward around her when he never felt that way before. Undressing her with his eyes, he couldn't help from imagining her sitting across from him while wearing one of her short, sheer, low-cut, and sexy nightgowns. He couldn't help from imagining her sitting across from him in her sexy, low-cut bra and white, bikini panties. He couldn't help himself from imagining her sitting across from him topless or naked.

Having successfully hidden his sexual lust from her for six, long, sexually frustrating years, now with love in addition to lust hitting him hard, he looked at her with unveiled, romantic love and sexual lust. She returned his look of sexual lust with her look of love, kindness, understanding, and compassion, not the looks he had hoped to receive but at least she wasn't angry with him for looking at her in that sexual way. She was his mother after all and would never scold him for looking at her with loving eyes.

Unless he was misreading her and he hoped he wasn't, he hoped that she had sexually been thinking about him in the way that he always sexually thought about her. He hoped that she masturbated over him in the way that he masturbated over her. He hoped that she imagined him naked and having sex with her in the way that he imagined her naked and having sex with her.

With incest such a steep mountain to climb and an uncharted territory to traverse, he hoped they were on the same, sexual page. Two likeminded people had a much better chance at making a sexual relationship work than one, especially an incestuous relationship. He hoped that they were about to have sex for the first time. He hoped she'd make him the happiest man in the world by giving him the chance to make her the happiest woman in the world.

Albeit, for the love of his mother, with age of no consequence to him, he didn't care that she was twice his age while he hoped that it wouldn't matter to her that he was half her age. What did age matter when they were in bed naked? What did age matter when they were in love and making love? Unless she's a minor, and as long as they're both consenting adults, age is of no consequence when a man is with the woman of his dreams.

* * * * *

'This is it. This is really it. This is finally it. Today, Valentine's Day, I'm going to make a sexual pass at my mother. I'm going to solicit her for sex,' he thought. 'Now or never, I need to make my incestuous move. I need to make my sexual intentions and my sexual feelings known. I need to make her my woman. I no longer want to be her son and her best friend. I want to be her lover too,' he thought while looking at her with nervousness and self-doubt.

Not wasting precious time with conversation as he always did before when sitting with her, then regretting not making a sexual move on her later, something special was in the air tonight. As if it was kismet, fate, and/or their destiny, it was as if they both knew what was about to happen. Hopefully in tune with one another, as if the angels were smiling down on them, they were both seemingly on the same, sexual page. Yet, instead of angels, it could be the Devil inviting him to sexually play in the Devil's playground with his blood related mother.

Obviously, no ands, buts, or maybes, in the way she was looking at him, she sexually wanted him as much as he sexually wanted her. Befitting that this moment should happen on Valentine's Day, the day of romance and love. In the way that she looked at him and leaned into him as if to cuddle or kiss him, he wondered if she ready for this sexually, romantic moment as much as he was?

Hoping that she just wasn't tired when she leaned up against him and closed her eyes, he hoped she was asking him to kiss her. He hoped she was asking him for more than just a peck but a long, wet kiss, a French kiss. He'd love nothing more than to part his mother's lips with his tongue. Yet, afraid to make the first move, he didn't know how his mother would react to his romantic kiss.

While imagining touching her cheek, he stared down at her pretty face. While imagining parting her lips with his tongue, he stared down at her red, full lips. While imagining moving her hair away from her beautiful, blue eyes, he stared down at the strand of blonde hair that always fell across her eyes as if it was a sexy curtain. Wishing he could touch them, feel them, fondle them, and suck them while fingering her erect nipples, he stared down at the impressions her big breasts made in her tight blouse.

'I'd love nothing more than to French kiss my mother while feeling her through her clothes,' he thought.

When he didn't kiss her, she looked at him with her big, expressive, blue eyes as if she was waiting for him to make his move to kiss her. She looked up at him as if she was expecting him to take her in his arms and make her his woman. She looked at him in the same way that he looked at her. With him supposedly the aggressive man and her supposedly the submissive woman, it was up to him to make the first, sexually, romantic move. It was up to him to take her. Going beyond their mother and son relationship, it was up to him to make her his woman and his lover instead of his best friend.

'Do it! Just do it,' he thought. 'Kiss her. She wants you to kiss her, you fool. Kiss her.'

As his way of breaking the ice and to not only show her what he thought of her but also what he sexually wanted from her, he took her in his arms. He brushed back the strand of her natural, blonde hair that fell in front of her captivating, blue eyes and stared at her as if she was the only woman in the world. As far as he was concerned, she was the only woman in the world. Filled with love, he looked at her as if she already was his one and only and as far as he was concerned, she was. Sexually excited, he gazed at her in the way he had never gazed at anyone before.

Then, not giving her the peck on the lips that he usually gave her, he kissed her. He really kissed her. Parting her lips with his tongue, he gave her a deep, wet, sexual kiss. The first time kissing her in such a passionately sexual way, he French kissed her. He French kissed his mother. He couldn't believe he French kissed his mother.

The first time kissing him in such a passionately sexual way, surprising him more than he surprised himself when he kissed her, she surprised him when she returned his kiss with her kiss. Even though he sexually lusted over her for six, long, sexually frustrating years, he never had such a sexual attraction to her before as he had now. Instead of just feeling sexual lust, as if she was Helen of Troy or Juliet of Romeo and Juliet, he felt romantic love.

'Being that today was Valentine's Day, maybe Cupid had something to do with this memorable day and magical kiss,' he thought while continuing to kiss her. When she returned his kiss, unable to think of anything else but her sweet lips, she blanked his mind with her kiss.

With them more best friends than lovers, he kissed her lots of times before, of course. He kissed her on her birthdays, on his birthdays, on Christmas mornings, on New Year's Eves, and on Valentine's Days but not like this, never like this. Nothing more than a peck, the first time parting her lips with his tongue, he had never French kissed his mother before. Now, as if addicted to her lips, he couldn't wait to French kiss her again.

* * * * *

Obviously, they were both ready and willing to take the next step in their friendship that had somehow morphed from friendship, sexually lust, and now to romantic love. As if a key, this kiss not only unlocked the love they felt in their hearts for one another but also this kiss freed the forbidden, sexual passion of a much younger man falling in love with a much older woman. In this modern age of cougars and Sugar Daddy's no one paid no never mind to how old or how young men and women are.

As if this one kiss validated their love and superseded their mother and son relationship, with that kind of connection already in place, they were hopefully now poised to be lovers in addition to being best friends. Now, no matter what curveball, fastball, and/or screwball life through at them, they could endure anything. Never expecting to kiss her, and never expecting her to return his kiss, but always hoping he could kiss her and hoping she'd return his kiss, he surprised himself as much as he surprised her by French kissing her.

His friends and their relatives would never approve nor understand his sexual attraction for a woman who was twice his age but he didn't care. His friends and/or their relatives would never approve nor understand his sexual attraction for his mother. Only, he didn't care. He was beyond all of that nonsense now.

'Fuck them,' he thought. 'They don't know how I feel about her and how she obviously feels about me. They'd never understand our forbidden love. Besides, what we hopefully do behind closed, bedroom doors is none of anyone's business.'

This first, French kiss was their first step in changing their relationship from just a friendship to friends with benefits. Their first, real kiss, an unforgettable kiss, even if nothing came of it, he'd remember their first, French kiss for the rest of his life. With her lips so soft, so full, and so sweet, he'd remember this kiss first forever. His dream of love, romance, and sex come true, whenever he wasn't physically with her, he'd remember pressing his lips against her lips and parting them with his tongue in his dreams. Now that they were together as man and woman and hopefully as lovers, in addition to best friends, he'd never leave her side.

Even better than the kiss that his Prom date, Jessica, a hot, sexy cheerleader, and his ex-girlfriend, gave him six years ago, when he was an 18-year-old, high school senior, this kiss was the best kiss he had ever had from anyone. Even better than the kisses that hot, sexy, drunken redhead gave him at a college frat party, her kiss paled in comparison to Kimberly's first kiss. Better than the kisses that he imagined giving Emilia Clarke from Game of Thrones, Scarlett Johansson from Lucy, Kate Beckinsale, Angelina Jolie, and Charlize Theron, he had never felt such sexual passion for any woman as he felt for Kimberly now.

'Wow,' he thought while reeling from her deep, wet kiss.

"Happy Valentine's Day, Kimberly," he said again.

* * * * *

Holding her and hugging her, wanting to hold her forever, he never wanted to let her go. Going for broke, while waiting for and expecting her to stop him, he had always wanted to touch, feel, and squeeze her beautiful, shapely ass. He moved another strand of blonde hair away from her big, blue eyes again before sliding a slow hand down her back to cup her sweet, firm ass in his horny hand through her short skirt and panties. Especially for an older woman, no doubt from her playing tennis, doing palettes, and swimming, she had such an incredible, round, firm ass.

The first time touching her in such a brazen, sexual way, she further surprised him when she allowed him to feel and squeeze her ass as if her ass already belonged to him. As if he was dreaming or sexually fantasizing this happening, he was happy that she allowed him to sexually touch and feel her while kissing her. Obviously sexually aroused by his French kiss, she looked at him stunned in the way he looked at her filled with lustful desire. Hoping she'd want to take the next, sexual step with him, now he couldn't wait to undress her. He couldn't wait for her to undress him. He couldn't wait to have sex with her.