Time for a Change Pt. 01

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A newly divorced 40-year old has a night out he won’t forget.
774 words
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Part 2 of the 4 part series

Updated 06/12/2023
Created 12/30/2022
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Jacob wasn't prepared for being forty and living alone all over again. He knew his marriage was on a rocky road for some time, but being told in no uncertain terms that he was no longer loved hit him harder than any pain he'd felt before. In the weeks that followed, he drank a lot. Months followed, and he'd go to work, masturbate to internet porn, drink some more, sleep until noon, and repeat that monotonous and familiar pattern until he no longer knew what he was waking up for at all.

It wasn't until one of the girls at work asked him out to her birthday night out that he decided to break the mould and try to be single again, at least try to enjoy his knew found situation without all the self-loathing and pitying. He'd always found Cara quite cute, and he was sure she was just being nice in asking him out, but something inside Jakob woke up. He imagined buying her a drink, spending time talking to her about any old bullshit he could think of, potentially charming her, and then maybe kissing her if he was lucky.

When the night finally arrived, he had drank a couple of shots of bourbon before leaving his house, if only to calm his nerves, then headed for the bar where she'd asked him to meet her. As he arrived, Cara was there, sitting at a table all by herself. He assumed it was more of a get together with others, and now, knowing she was alone, he felt more nervous than before, wishing he'd drank a few more glasses of his cheap liquor.

Cara looked stunning. She was wearing an emerald green dress that showed off her shoulders, teasing her round, ample breasts with a cleavage that made his temperature rise.

"Hey, Cara," he muttered. "You look incredible."

She turned round to meet his gaze, smiled at him while playing with the straw in her drink with the tip of her tongue, and stood up to hug him. Her breasts pressed against his chest, and she leaned in close, pressing her body against him.

"Hey, you," Cara replied.

She stayed close to him for longer than he thought she would, feeling the tightening in his trousers press against her stomach. She could sense he was turned on by her, and playfully held the embrace until he coughed nervously. Cara let go, and the two of them grabbed a couple more drinks.

An hour passed and the two had have a fair amount of alcohol. Jakob kept looking at her golden skin and her dark brown hair, and how it grazed the skin of her chest. She noticed every time he looked at her - every time he admired her body or her smile. Suddenly, she stood up and slowly sat down on his lap, grabbing his hands and letting them fall upon her waist.

As her ass pressed against his legs, he could feel his cock harden, and poke between her cheeks as she ever so slowly started to rock back and fourth as not to arose suspicion. She could hear his stifled moans as she softly grinded him, and giggled while holding her drink, taking a sip between each movement. Cara put her glass onto the table and stealthily reached for his zip, raising her body off of him, then looked around to see if anybody was watching. She then reached between his now opened zip, pulled out Jakob's dick from between the buttons of his boxers, and started to stroke him. It was warm and clammy, but rigid and pulsing in her hand, slightly wet from the coldness of her glass. After a few more strokes, she sat back on top of it, his dick exposed and rubbing against the soft fabric of her dress. He could feel the shape of her cheeks clearly on his cock, and the smoothness of the silky dress felt good on his member. She continued to rock back and fourth, listening to the changes in his breath that might give light to when Jakob was ready to cum.

As Cara heard him moan, she could sense he was about to ejaculate all over her dress. She stopped grinding and gently got up, walked off to the washroom before beckoning him over with her finger. She disappeared through the door and left him alone. He was able to put his cock away before composing himself, drinking his last drop of whisky, and left the table in search of Cara, hoping to find out what the seductress' pussy felt like wrapped around his throbbing cock.

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