Ashley's Weekend Ch. 01

(hello out there! So this is the start of a new series wherein a young woman is introduced to the BDSM lifestyle via Shibari and other methods. I LOVE character and scene building so yes that slows the initial progress of, but I'm sure once rolling you WILL enjoy! PEASE give me some comments, and thanks so much for reading!!!)

It was serendipity, really. Johnathan Roberts was just chilling at his favorite gulf-side café, enjoying the day. For nearly 30+ years He'd been a lawyer, amassing a partnership in a firm and gaining substantial real estate holdings/investments, but after becoming a widow he just grew tired of it, and now in his mid-50's, He'd sold his shares of the firm, his rentals and undeveloped land, and moved two states/500 miles to Florida's panhandle, having decided to go into semi-retirement.

This 'forgotten-coast' quiet area breeds its own type of people, and after some months he was becoming known as less of an outsider, but still enough so that locals thought of him as one of those aloof, self-absorbed types. They weren't entirely wrong, and Johnathan guessed that's why the two waitresses at their station didn't know or care that he could overhear their conversation regarding Ashley Brooke West, their coworker's, desperate financial situation. And that is where the idea was born, that lead to the aforementioned moment of enlightenment.

Under darkening skies, he was on his way the next day to grab some lunch when Johnathan saw Ms. Ashley Brooke West, the one of whom the two waitresses spoke, walking and looking pensively up at the sky. She didn't even have an umbrella, and that was serendipity. He noticed her look beamed as she saw a customer she recognized step out of the luxury black full sized GMC truck, umbrella in hand. As he opened her door and got her seated, she said "Wow a knight in shining armor! Thanks so much for rescuing me!" Indeed, young lady, indeed.

Ashley West was a real beauty, standing about 5 foot 8, she was a natural brunette, her hair below her shoulders, pouty lips and doe eyes, and a curvy body with super nice breasts and shapely hips. She looked to be in her mid to late twenties, making her nearly half his age. Perfect. Not what he had been truly looking for, but one thing the courtroom had taught Johnathan Roberts was to go with what you've got, and go all in. The rest works itself out.

They talked a bit as he drove, her talking all about her dead car and her money woes (same as he heard the other night) and she gratefully accepted his offer of lunch, even mentioning that it was her first meal of the day. That was noticeable as she wolfed down her food, and he even bought her a to-go plate for her 'friend'. It was when she was complimenting the new 2023 Denali Ultimate Truck, with its plush leather interior that he went with his play.

"Ashley, I'm sorry you're in a tough spot, but I have an idea, if you're willing to listen."

She smirked and eyed him, replying, "Umm...OK...Go ahead."

"Look, I was at the restaurant the other night, and over heard via my waitress that you were on hard times. In addition to your car, you likely have school in the fall too, right?"

She rolled her eyes and grunted an "Ugh." Then looked at him and said, "My family is tapped, we're locals, and blue collar at that. No beach house, no nice vehicles to drive, no offense. I'm going to have to drop, and just work a few years and see what happens. I desperately want out of this life, but I owe more than a grand on the car, rent's behind even with a roommate, so school? Out of the question for now, especially at server pay rates."

"Yeah well, that's my idea. How much would it take for you to be fully caught up and then also how much for school?"

"I already see where this is going," she said quickly.

She was smart, he knew, but he noticed she didn't get out of the car or curse/slap him, so he was still in the game. At his prompt she answered "$2K for the car and rent, and another $3k in eight weeks for school to start the semester" She narrowed her eyebrows waiting for the expected brush off, but they popped up when Johnathan replied quite nonchalantly, "Oh, I can easily do that. In fact, I could be considerably more generous, depending...."

"You.....You can?" she finally stammered out, her mouth hanging open. It wasn't at all what she was expecting as he put the Truck in motion again.

"So I turn up over the waterway, then it's the last road on the left?" He replied. Seeing her nod numbly he continued. "I tell you what; I'll do more than that for each, say...$6K just for this weekend? I also have an idea for the rest, but let's get this out of the way first."

"But...well...there's more to it than that." Ashley said. Seeing the waterway she said "Go straight, let's talk." With the rain pelting the truck and starting the automatic wipers, they drove, and worked out the details. He was careful to let her know that unlike their idea of an unknown 'Sugar-Daddy', or having to work through some damn site, he was what could be called safe and a "known quantity" and that term resonated with her. He assured her he would be a very discreet gentleman, and the agreed number was $6K for the weekend, starting Friday late afternoon to Sunday early eve, the rest to be discussed. She was surprisingly matter-of-fact about the whole thing, and was even agreeable to the notion that she would have to be an 'eager participant.' Johnathan gave her $500 for listening to him, and dropped her at her address. Friday couldn't get here quick enough!

****

Friday arrived and they agreed that Johnathan would pick up Ashley at her address a bit early. Which was fine by him? He had a shower, trimmed nicely and shaved his balls so everything was looking good, and set off, excited to see a text with Ashley's address, and that she was waiting. Pulling up at the old mobile home off a backroad, Johnathan took a deep breath and walked to the door. All he could hear was his heart pounding as he rang the doorbell.

The door opened, there was no one there but a voice said come in. he walked in, Ashley closed the door and gave him a kiss. He was thunderstruck; she looked even better than he was hoping for. Dressed in very tight PVC type trousers and a tight black vest top. She had an amazing body and her outfit showed it.

She grinned and said "Well by your look He'd say you approve."

All he could manage is "Wow, Ashley.....you look...amazing." She grinned and pointed towards her two small bags, and off they went.

****

Ashley was quite chatty for a bit, and then asked a serious question. "Why? And specifically, Why me?"

"Well really, it's just timing." Johnathan replied. "Look, I'm a widower as you probably know. Been a bit more than a year now. When I am ready for a relationship that's great, but not now." Pointing out at an island in the distance he said "That's where we're headed" and turned onto the bridge, then continued. "If I'm right, then I'm 2xs older than you, plus a few, so you can't say I exactly planned this, nor do I think this is some kind of movie, but at the end of the day, I have a definite want, and you have a definite need. This satisfies both." He liked that she smiled as she nodded.

There was silence as they pulled into the gated community, and as they pulled through the gate on his driveway she finally spoke. "You have a certain flair, I do say, and I also admit that you are rather easy on the eyes, even though you're much older..." She gave his thigh a squeeze, and continued. "Yes, this is a means to end," and then gestured all around at the beach front house, "but all in all it won't be a bad way to go....so let's go."

They went up the front main stairs after a too brief tour of the first level, and what a view he had following her upstairs, his hard on was raging now. They made it over to the large couch that faced the ocean via a bank of windows. Nudging between himself and the windows, she started taking her top and trousers off, and she was standing there in lovely blight blue cotton matching bra & panties. Man, was she hot.

Ashley motioned to Johnathan to get undressed, so he removed everything apart from his boxer-briefs. She came close, and they kissed. She was running her hands up and down his body. He returned the favor, feeling her lovely soft and warm skin.

She moved his hand in between his legs, rubbing his cock first and then whispered to him, "Impressed. Please impress him some more."

As he dropped his underwear Ashley took his cock, and he let out a soft moan. It felt electric somehow, and Johnathan looked like he could have popped his cork there and then. She removed his boxers, and with a knowing smile pushed him back and onto the couch.

She was straight down on her knees. His rock hard cock was pointing towards the ceiling; she held it against his belly and started licking his balls, sucking on them gently. The warm feeling of each lick and suck had him squirming and moaning in delight. She started to wank him whilst using her mouth on his balls but he moved her hand away as it was going to make him cum way too fast.

She stopped with a curious look and asked "are you OK?"

He replied "Hell yeah but it's going to make me cum too quick."

With a devilish look in her eye she took the base of his cock in her hand. Slowly Ashley used her tongue all over his throbbing head, slowly and firmly sucking his cock but only down about two inches. This was all too much and he said "Shit girl, I'm about to cum!" She didn't even move or slow down as he exploded right into her mouth. Ashley timed each spurt with her movement and it felt like Johnathan just kept cumming and cumming. He was literally drained and flopped back on the couch, his chest heaving.

Ashley stayed with his cock in her mouth for a good minute until his hard on had subsided. She was sure it was the best blowjob he had ever had, and the weekend was still young. Ashley jumped onto the couch beside him after having a good drink of water. Gesturing towards the Ocean she said "Well that's a great way to start, with a great blow and the view to match?".

They both laughed and he agreed. The view across the beach, with the low rolling waves typical of the Gulf was something Johnathan Roberts had paid well for.

They chatted for a bit, and she told him she was actually bi and had been living with a female lover for a few months. Her family had cut her off, and that was when the financial problems began. She also admitted that she had looked at the sites but was not impressed. When she saw the size of Johnathan's dick, along with the house, she decided this could be a fun weekend.