Hey everyone! I dreamt this up while writing my multi-part series (see my other works). This one is an "origins" story of sorts, as it centers on my previous character's (Johnathan Roberts) father...always good to know where he got it from!
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Ashley Hutchens checked her phone. "Yes, I'm here, last patio home on the right" was all it said. Outside the car there was a 'Clack!' and a hum as the gate to this snobby place swung open. Ashley put the old Toyota in in first, released the clutch and rolled into the gated community, feeling a bit out of place among the opulence.
Ashley had never cared much either way for Jason Roberts. THE senior partner at law the firm, he was a much older man, replete with whitening hair. However he had a handsome, distinguished air, and it didn't hurt that he was nicely dressed. She had always known 'JR', as the non-lawyer employees snidely referred to him, to be rather well-to-do, and the high-end cars in the drives of this little hamlet on St. Georgina Island certainly showed. She sighed and shook her head, wondering how the old man had gotten a hold of something she had spent years saving & looking for.
Ashley had worked on the other side of their very successful & profitable law and real estate office for about 4 years now, mostly for the old man's son, who had a bit of a reputation. She had spent the very large part of it saving to one day 'repay' her dad. Ashley had grown up living only just above edge of poverty. They had enough to make it, but only just. 6 years back, her dad had sold the only possession they had worth much of anything, a rare watch that he had bought when he got out of the navy. It had paid more than a year of schooling for her two year degree. Kaitlyn had been saving since hired to purchase another one of these for her dad as "re-payment", but it had always been elusively just out of reach. That is, until Jason Roberts found out she coveted one.
Jason Roberts had noticed the really attractive little Ashley Hutchens on the other side of the office a long time ago. She stood maybe 5ft or so, it really seemed to depend on the shoes she was wearing. She had a tight, curvy body, dark brunette hair that was mid-back, and a wide smile for such a small face. Always professional, she worked very hard and kept to herself. As she was a subordinate coworker, working on his son's side no less, Jason steered clear, but on several occasions, He happened to catch her staring at a man's watch on her desktop, often on Ebay and the like, a particularly nice watch at that. Odd thing was, Jason knew he had one of those he never wore. It wasn't like him, the ranking partner, to desire such a young woman and the fact was, such a scandal would be devastating, we're it not carefully handled. But Ashley Hutchens had that certain something and pretty soon, the little head was doing the planning.
Janet, the office snoop, got him the story on the watch, & Jason let it cool for more than a month, lest he risk tipping off Janet/the office. It only took a 'chance' (wink-wink) meeting away from the office for him to make the offer. He was impressed that she willingly took it. Ashley played it cool for sure, because it was almost two weeks later when she got in touch, and the deal was made.
And so that was how he found himself on this day, a guy in his very late 50's, standing in his patio home and waiting on a lady literally half his age plus a few to show up for a 'trade'. A widower, Jason spent what little time he wasn't working for the firm either swimming, biking, or working out. So a new way to 'burn off energy' was not only welcome, but he certainly intended to make the most of it.
Ashley pulled into the drive, noting he had moved his very nice Maserati and some kind of low, classic car under a cover to allow the old Corolla into the shaded carport. She tugged at her new leather skirt and blouse, making needed adjustments due to the seat belt and the clutch, and put on her new heels. 'JR' was at least generous.
'JR' had asked her to first go by a nice boutique in town, and true to his word they had a 'small account, and some suggestions' for her. After going with the white blouse, black leather skirt, hose and garters, she had more than enough for a pair of boots and some accessories too. Taking a deep breath, Ashley got out and made her way to the door, seeing that he already had it open. She had to admit he cut a nice silhouette for an older man, and holding the door was a nice, gentlemanly touch. Not something she as used to.
It wasn't that 'JR' (she had to quit calling him that) was bad looking. He was about 6ft/183cm, and actually quite lean, not having the pot belly or body fat as with so many men his age. His hair was thinning and graying, but his facial lines were handsome, and she found herself thinking. But he was older, like dad age, and then some, and that had never been her thing.
However, it was apparent that without a 'compromise' of some type, Ashley Hutchens was never going to pay back her dad, and she just could not accept failure. Ashley was not above using her body to achieve her goals, she had done so in the past, and at least 'JR'(one last time) was clean, and the surroundings were certainly nice.
"Do you have it?" she asked, matter-of-factly, after showing him her phone was fully off.
"Of course." he answered as he also showed his phone to be off, and pointed to the box on the table. "as-new-as stated."
"Nice that it's in the box" she commented, then "I need to know this is going to stay strictly between us." Ashley asked, as she examined the watch, then put it in her new & expensive bag.
"Only ones who will know are those you choose to tell," he responded, then added, "I see you took advantage of the offer regarding clothing. Wow you look great in it. Consider that a thank you gift for the consideration."
Ashley smiled for the first time. "Yes, I will say, it was a nice gesture, and glad you like it." Sensing his intentions, she stepped over, placed a hand on his chest and said, "Why not have a seat, I'll show you the rest of what you requested..."
He let her nudge him back, and had a seat on the couch. Holding a hand up and making a slow 'twirl' motion, Jason smiled as he watched this beautiful creature turn. The leather skirt was office-length (what a shame), but she looked mouth-watering in it. She was standing between his knees now, looking down at him, and she lifted the blouse over her head. She was indeed wearing the black satin bra, and it held those B-C cups just right. She looked down at the tent in his pants, and simply smiled, and Jason noticed what a sexy smile it was.
Turning, she let him lower the rear zipper, and smoothly, she stepped out of the skirt to reveal the matching panties, garters and hose (the panties being notably settled over the garters, an indicator she had certain expectations). So far Jason thought, it was looking like a good trade.
Ashley was careful with these clothes. She was used to buying at discount stores and Goodwill, so boutique level items were certainly special indeed, and she coveted them. She had never been one for a thong, so she had chosen panties that, while 'thin' as they went between her ample cheeks, were not the goofy single string in the back. Leaning forward, Ashley pushed her hips back and bowed her spine, showing off what she had, & she heard him sigh just a bit, obviously enjoying the show. He wasn't pawing her, he was letting her be in control & present herself, and she had to admit, it was a nice change. Perhaps this deal was going to work out to have some 'perks'.
The look of that pussy in those black panties, thru her legs made Jason want to leap of the chair and POUND her, but he was going to get his money's worth, so he let her continue the show. She stepped back just a bit more, she was close, so he lightly touched her sexy ass by giving it a kiss. He heard her give a little chuckle, then she stood up, reached back, and released her bra. She turned around, and finally he got to see those gorgeous breasts & nipples. They stood out like erasers, and the area around them was a pretty, petite, pale-pink circle.
There was something that Ashley liked about showing off her body. Doubly so that this man seemed to appreciate it. She gave him a final 'twirl' and then, taking his hands, she placed one on each breast. Again, Ashley was pleasantly surprised, as he cupped and lovingly kneaded her nipples. He was certainly a break from the norm, this man, so she reached down, and pulled his shirt over his head, then the same for his undershirt.
Straddling him, she allowed him a kiss. This was not her norm, but then again, things were going well. She could feel her sex rub that tented part of his pants, and it was nice, especially as he moved to the nape of her neck (yes...) then to a breast, where he took his time. He had one hand cupping a breast, the other a cheek, and Kaitlyn found herself unexpectedly/pleasantly wet, and she welcomed it.
The taste of her nipples was nice, and they seemed to poke out even more. Jason Roberts knew she was a mom, and the twisted side of me thought "lucky sum-bitch, getting to nurse those". She moved his face back to hers, and offered him a second kiss, this with just a bit of tongue. He wanted this girl, no doubt, but not here, He WAS getting his money's worth, so moving the other hand to her ass, and with a bit of effort, Jason shifted...moved...(Thank goodness for all the workouts) and stood up, holding her. She happily wrapped her legs around him, and he walked her back to the bedroom, getting a few kisses along the way.. Finally, he was going to give the maid something proper to clean.
Being that she was so petite (just 100 pound/54kg), Ashley was used to getting picked up like this, though she didn't mind it a bit. This man was not aggressive at all! He was a good kisser, not just all over her, so she enjoyed the feeling of being carried, then placed finally on a bed, and what a bed it was! It was a gorgeous, ornate, and HUGE four-poster, and the sheets were just unbelievably comfortable, even in just her hose and garters.
