The Perfectly Imperfect Marriage

Twenty-year-old grandson has a plan to seduce his sixty-eight-year-old grandmother

Continued from chapter 03:

After reading about women who deliberately dropped their towels to flash pizza delivery men, mailmen, UPS drivers, and FedEx drivers, he always wondered if his sister deliberately dropped her towel to flash him. Even though he enjoyed masturbating to the thought of his sister deliberately flashing him her naked body, he seriously doubted that she did. The first time his sister was naked in front of him, she screamed and picked up her towel before he could even get a good, long look at her naked tits, her naked ass, and her naked pussy.

Beyond embarrassed and mortified, Kathy obviously wasn't as sexually attracted to her brother as he was to his sister. Just as it sexually excited him to see his sister naked, it sexually excited him that his sister saw his naked prick. It sexually excited him that his sister watched him masturbating himself while she knew that he was masturbating over seeing her naked body. With her never removing her eyes from his exposed prick, it sexually excited him that she saw him cum.

Replaying it over again in his mind, he couldn't believe his sister stood there watching him stroking his cock as he shot a huge load of cum all over his chest and stomach. Yet, between seeing his mother's naked breasts, seeing his sister naked, and his sister seeing him masturbating himself, he now had plenty to masturbate over. Without a doubt, he'd be masturbating over his mother's big tits, his sister's hot naked body, and his sister seeing his erect prick for years.

His sexy, immorally immodest grandmother was a different story. She was nothing like his mother and sister. Carefree and unencumbered, having worked as a nude model for artists for years, she could have been a nudist. With her admitting to having a lot of sex with a lot of men, she briefly lived her life as a hippie in Vermont and as a Bohemian in the East Village of New York. She even attended Woodstock and shed her clothes in the pouring rain to play in the mud. Adding color to their otherwise boring lives, she lived with them in the spare bedroom.

As if she wasn't wearing anything at all, he couldn't count how many times he had seen his 68-year-old grandmother in her sheer, short, low-cut, revealing nightgown without the modesty of a robe. With him barging in his grandmother' bedroom without knocking in the way that he barged in his mother's and sister's bedrooms without knocking, he had seen his grandmother in her bra and panties, topless, and naked numerous times. Only, in the way that his mother covered her nakedness and his sister screamed, his grandmother never made a move to protect her modesty from his horny eyes.

Too much of a coincidence to see her without her clothes so often, he figured his grandmother was an exhibitionist and was deliberately flashing him. A virtual cum machine, he was always masturbating. When he wasn't masturbating over the imagined thoughts of his girlfriend, Mary, in her bra and panties, topless, and/or naked, he masturbated over all the up-skirts views and down-blouse peeks that he saw on campus. He couldn't count how many times he masturbated over imagining seeing his mother and sister in their bras and panties, topless, and/or naked. He couldn't count how many times he masturbated over all that he saw of his grandmother in her sexy nightgowns, in her bra and panties, and topless and/or naked.

Now that he saw his mother topless, his sister naked, and his grandmother in all manner of undress, he had seen all three generations of the women in his family. With him inexperienced enough and curious enough, he'd have incestuous sex with his grandmother if he could. Horny enough to masturbate over seeing his grandmother's sexy and shapely semi-naked and naked body, he started returning the favor of flashing her in the way she always flashed him. Whenever his mother and sister weren't home, in the way his grandmother wore her sexy nightgowns without the modesty of a bathrobe, he walked around his grandmother wearing pajama bottoms without the modesty of underwear.

Allowing his morning erection to make a surprise appearance, he deliberately flashed his grandmother in the kitchen when they were alone. With her at eye level to enjoy his show of exhibitionism, his best flash was when she was sitting at the kitchen table drinking her coffee and he leaned over for the cereal. As if he had perfectly planned it, even though he hadn't, his erect cock popped out of his pajama bottom pee hole and nearly hit the side of her face.

"Careful," she said touching and pushing away his stiff prick with her fingertips. "You could have poked my eye out with that thing," she said laughing.

'Oh, my God,' he thought. 'My grandmother not only saw my cock but also she touched my cock,' he thought. 'I can't believe she saw my erect prick. I can't believe she touched my erect prick. I can't wait to masturbate over my grandmother seeing and touching my erect cock,' he thought while sexually excited and eager to masturbate over this later.

Chapter 04:

Whenever alone with his grandmother, while waiting for her to open his bedroom door without knocking, which she had a habit of doing, he allowed her to catch him naked and/or masturbating several times. In the way that she always stared down at his engorged prick without looking away embarrassed that she caught her grandson naked, it was so sexually exciting to expose his cock to his grandmother. With his grandmother a willing participant, he loved flashing his prick to his grandmother.

He pretended he didn't know she was standing there watching him jerk-off, even though he knew she was standing in his room watching him. In readiness or her barging in his room without knocking, whenever he heard her walking towards his room, he'd strip naked. Whenever he heard her walking toward his room, knowing she'd open his bedroom door without warning, he'd start masturbating himself.

As his way to pretend that he didn't know she was standing there and as his way to expose his cock to her, once naked, he turned to face the door with a tee-shirt over his head. Again, as his way to pretend that he didn't know she was standing there, he always closed his eyes when masturbating. Sometimes, pretending he was the victim and his grandmother was the incestuous stalker, even though he was the exhibitionist, he even wore his headphones.

Even though he knew she was there watching him, giving his grandmother a free masturbation show, he continued stroking himself. Timing his ejaculation to when she opened his door and was standing inside of his bedroom to cum as she watched, he'd open his eyes and act surprised. Too late to stop himself from cumming, instead of acting sexually excited, he'd act embarrassed that she was standing there watching him stroke his stiff prick.

"Oh, my God. Grandma. I didn't know you were there. I'm so sorry. I'm so embarrassed," he'd say while acting mortified that she caught him masturbating himself and cumming in front of her again. "Please don't look at my cock," he said trying to stuff his erect penis back in his underwear.

In addition to flashing her his cock, masturbating himself, and cumming in front of her, he wished she'd volunteer to help him masturbate himself but she never did. Masturbating while wishing she'd take his cock in her hand to stroke him before taking his stiff prick in her mouth to suck him, he masturbated over his grandmother giving him a hand job before giving him a blowjob. Only, not even reaching out her elderly fingertips to touch his exposed prick, she never did that either. As if mesmerized by the sight of his erect prick, all she did was to stare at his exposed prick and stare at him ejaculating a load of cum all over his chest and stomach.

Nothing more than a sexual fantasy that he masturbated over, a dream come true, he wished his grandmother would give him sex. While she stroked him and sucked him, he'd love nothing more than to cum in his grandmother's mouth while feeling and fondling her big tits and fingering her erect nipples. At the very least, he wished she'd take a warm, wet facecloth and hold his prick in her elderly hand while washing the cum from his stomach and chest.

Seemingly, she enjoyed staring at his prick as much as he enjoyed exposing his prick to her and as much as he enjoyed seeing his grandmother in her bra and panties, topless, and/or naked. Seemingly, she enjoyed watching him masturbate himself and ejaculate as much as he enjoyed her watching him masturbating himself and cumming. Seemingly, she wanted to have sex with him as much as he wanted to have sex with her. Only, as if the incestuous line was electrified barbed wire, she was his grandmother and he was her grandson.

### Debbie Dear Debbie ###

Imagining having sex with his grandmother was an endless masturbation cycle. He masturbated over imagining his grandmother in her bra and panties, topless, and naked. He masturbated over touching, feeling, and fondling his grandmother's naked body while having sex with her. Then, he masturbated again after he purposely exposed her cock to her and she watched him stroking himself and cumming.

With him masturbating every day, multiple times a day, he wondered if his grandmother masturbated. He wondered if she masturbated over him in the way that the masturbated over her. In the way that he allowed her to catch him masturbating himself, he wished she'd allow him to catch her masturbating, but she never did. He'd love to watch her touching, feeling, and fondling herself in a sexual way.

While imagining listening to her moans of sexual pleasure, he'd love nothing more than to barge in his grandmother's bedroom to see her nightgown raised to her waist. With her legs spread wide, he'd love to see his grandmother naked while she rubbed her clit, fucked her pussy, felt her big tits, and fingered her nipples. In the way that he arranged for her to catch him masturbating, he wished his grandmother would allow him to catch her masturbating. He'd love to barge in the bathroom when she was taking a bath to watch her masturbate herself.

'Oh, grandma,' he thought. 'I wish you'd masturbate me. I wish you'd allow me to catch you masturbating yourself. I wish you'd ask me to wash your back, your big tits, and your pussy while you're sitting in the bathtub.'

Yet, so sexually exciting for him to flash her his cock, with him unembarrassed and horny enough to do so, after a while, he even allowed her to watch him continue to stroke his cock while cumming. It took two to play their masturbation game of voyeurism and exhibitionism. With her unashamed, unembarrassed, and not shy about staring at his exposed prick, instead of apologizing for opening his bedroom door without knocking and instead of leaving, she stayed to watch his masturbation show while talking to him. Obviously, in the way that she stared at his erect prick, she wanted to see his stiff cock and her grandson cumming as much as he wanted to show her his engorged penis and allow his grandmother to watch him cumming.

He only wished his grandmother would volunteer him her help in masturbating him. He wished she'd volunteer him her hand. He wished she'd volunteer him her mouth. He wished she'd volunteer him her pussy. While pretending that she was his mother or his sister, he wished he could have sex with his grandmother.

In the way that he sexually lusted over his MILF of a mother and his sexy, bitch of a sister, knowing full well that he'd never have sex with either of them, he turned his attention to his grandmother. He sexually lusted over her as much as he sexually lusted over his mother and sister. An easy target, seemingly, his grandmother was just as horny as he was horny. His preferred victim, seemingly, his grandmother was just as sexually frustrated as he was sexually frustrated.

### Debbie Dear Debbie ###

Whenever his mother and sister weren't around, his grandmother was always flashing him. She flashed him her sexy, nightgown clad body. She flashed him her sexy underwear when standing in her bedroom in her bra and panties with her bedroom door wide open. She flashed him her big, naked breasts when she was topless. She flashed him her naked body when she wasn't wearing anything at all.

With his grandmother so sexy and so incestuously sexual, he figured he had more of a chance having sex with his grandmother if he had the nerve enough to make the first move. In the way that she always stared at his naked prick, he always stared at her in her bra and panties, topless, and/or naked. In the way she barged in on him while he was naked and/or masturbating himself, she was always walking around him in all manner of undress.

"You have such a big, beautiful cock, Jimmy," said Grandma Ruth leaning against his open-door jamb and staring at his erect prick. "You're going to make some woman very happy one day."

She gave him a sexy smile.

"Thank you, Grandma," he said staring down at his exposed prick before staring back up at his grandmother.

She curled her hair in her fingers while talking to her grandson. Years later, Jim read that a woman curling her hair with her fingertips was a sexual sign.

"Only, you shouldn't masturbate so much. You need a girlfriend to do that for you," she said giving him a sexy look as if volunteering her hand and volunteering to be his girlfriend. "Your grandfather never had to masturbate himself with me around," she said nodding her head while sliding a slow tongue across her full lips.

'Oh, my God,' thought Jimmy when seeing his grandmother's tongue sliding across her full lips. He imagined her stroking him. He imagined her blowing him. He imagined cumming in his grandmother's mouth and her swallowing his cum.

She gave him another sexy smile but this time with a naughty look and a wink while moving her hand back and forth as if she was already giving him a hand job. He wondered if she was hinting that she'd masturbate him if only he had nerve enough to ask. Even though he wished his grandmother would masturbate him, he'd never have the courage to ask her to do something like that.

She was his grandmother and not some cougar whore that he picked up in a bar for sex. She was his mother's mother. How dare he sexually lust over his grandmother in the way that he was incestuously lusting over her now. Even though he wanted to ask her to masturbate him, already feeling too much like a pervert for flashing his grandmother his cock and allowing her to watch him stroke himself and cum, he was too embarrassed to ask her.

### Debbie Dear Debbie ###

The best time he ever had with his grandmother was when he was alone with her for a weekend. His sister was away at college and his mother was visiting a sick friend or so she said. She may have been on a weekend date and having hot sex with a man she met for all that he knew. Sexually excited imagining what he'd do when alone with his grandmother, he was already plotting his sexual seduction and planning his sexual moves.

He had never been home alone with his grandmother for more than a few hours and now they were alone with one another for an entire weekend. This was it. This was his chance to seduce his grandmother. This was his chance to touch, feel, and fondle his grandmother's naked body while having sex with her. This was his chance for him to get his grandmother to stroke his cock, suck his cock, and fuck his cock. Hoping to somehow have sex with her, he ran all the sexually incestuous scenarios through his head of how he could seduce his grandmother.

With first things first, turning down the lights low and putting on some soft music, he'd have to get her in a sexy, sexual mood. She loved the Beatles, whoever they were. He could play one of their records. Then, maybe he could get her a little tipsy with copious amounts of wine. She liked wine. She had two glasses of wine every night.

Maybe if he got her horny enough and drunk enough, she'd allow him to feel her big tits through her nightgown. It sexually excited him to think about feeling his grandmother's tits through her nightgown. She was always walking around the house wearing her nightgown without the modesty of wearing her robe. Dressed as if she was a prostitute at a whorehouse in Nevada, she wore the sexiest nightgowns that left little to the imagination. His mother was always scolding his grandmother for showing too much skin.

"Mom, put on a bathrobe. Jimmy can see everything," she said.

Only, with his grandmother a free spirit and an exhibitionist, she never covered her sexy, shapely body with a bathrobe.

"I'm sure I'm not showing my grandson anything that he hasn't already seen. I'm too hot wearing a bathrobe," she said. "Besides, why would he want to look at an old woman?"

That was when he thought of something even better than turning the lights down low and playing Beetles music. Aware that certain movies put his grandmother in the mood for sex, he agreed to watch his grandmother's favorite, older women with young men movies with her. If he had his druthers, he'd love to watch Spanking the Monkey and The Secretary with his grandmother, his two favorite movies.

She loved Billy Wilder's Sunset Boulevard with Gloria Swanson and William Holden, when Norma Desmond, played by Gloria Swanson, takes up with a young writer, William Holden as Joe Gillis. She loved Truman Capote's Breakfast at Tiffany's with Audrey Hepburn and George Peppard. George Peppard plays Paul Varjak, a kept man by a wealthy designer. He falls for a party girl, Holly Golightly played by Audrey Hepburn. She loved Charles Webb's and Mike Nichols', The Graduate, with Anne Bancroft and Dustin Hoffman. Anne Bancroft plays Mrs. Robinson, a cougar who seduces her neighbor's son, Benjamin Braddock, played by Dustin Hoffman. Those three movies, especially when she was drinking, always made his grandmother horny.

"Another glass of wine, Grandma?"

### Debbie Dear Debbie ###

He filled her empty wine glass nearly to the brim. Continuing to ply his grandmother with alcohol, he figured that it would be easier to seduce his grandmother when she had been drinking. After being the victim of her sexually, inappropriate suggestions, he knew that the more wine she drank, especially after watching any one of these movies, the more sexual she became. Obviously, her sexual fantasy was her having sex with a much younger man. In the extrapolation of that sexual fantasy, he hoped that her sexual fantasy was her having sex, incestuous sex, with him.

Moreover, the more wine she drank, the more careless she was with her nightgown. The drunker she became, the more she gave him inadvertent or deliberate up-nightgown views of her white panties and down-nightgown views of her big tits. The more wine she consumed, the more careless she was with her wardrobe.

Just as he loved spying the sexy coeds on the college campus while hoping to see their panties and bras, he enjoyed seeing his grandmother in all manner of undress too. So sexy and with him imagining the rest, as if he willed it to happen, he loved it when her nightgown strap slowly slid from her shoulder. Just as he loved watching her expose the meaty, jiggling top of her big breasts, he loved seeing her long line of sexy cleavage, and the white, creamy side of her big breast. While imagining the rest, it was more sexually exciting to see bits and pieces of his grandmother's shapely and sexy body than to see her completely naked.

Something that got him in the mood and gave him an erection, the more wine she drank, the more of her body she inadvertently or deliberately flashed him. The more wine she drank the easier it was for him to touch her and feel her without her resisting his inappropriate, incestuous, sexual touches. She was already always so touchy feely anyway but even more so when she had been drinking, especially while watching her sexy movies of older women having sex with younger men. He hoped that if he plied his grandmother with enough alcohol that she'd not only allow him to put his hand on her big tits but also that she'd put her hand on his erect prick.