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…at all times good to know where he got it from!
***
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 at all times 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 at all times 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. At all times 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 sort 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 profile, 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 gonna 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 gorgeous 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 wondered, 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 gonna 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 gonna 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 beautiful 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 wondered “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 gonna 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 beautiful, ornate, and HUGE four-poster, and the sheets were just unbelievably comfortable, even in just her hose and garters.
Johnathan broke his kiss to strip, and Ashley had no problem helping him. At last, she got to see the bulge and Ashley did an honest double-take. This man was BIG, especially for an older guy. It looked thick and ‘veiny’ and the damn thing was dripping too. Ashley would have been fine to ride that to completion, but then she got the second surprise of the day.
As he playfully ‘rough-housed’ her, “tearing” off her panties, Jason suddenly slowed, and starting at her ankle, he began kissing his way up the inside of her leg, looking at her with a devious little-boy smile. ‘This was becoming a great deal!’ she wondered as the kisses made their way up her thigh.
Jason liked that she ‘got it’ when he was playing-rough. She seemed to melt in to the bed like she belonged there (and she certainly could), and he had to say, while Ashley Hutchens nipples tasted good, the Pussy was incredible. All women have a taste, and this one had a genuine sweetness to it.
Ashley had shaved her pubes to a narrow landing strip, so he worked his way down, ‘tugging’ at her pubes just a bit, before kissing her bright pink-red clit. He had moved his hands to be cupping her Ass, and with his thumbs he eased open her labia, then began to methodically lick down one side, lap the Vagina just bit, then up the other, to kiss the clit, and begin over. Judging by her moans and squirming, she was enjoying it.
“Oh SHIT!” Ashley said aloud. This guy really knew what he was doing! Girls around the office had said that the old man kept his distance, and was both sweet while being very quiet. Several of the older ladies had flirted with him, to no avail. Right now though, all she could think about was how he was eating her out…and how incredibly well he was doing it.
Ashley liked that he was absolutely game to having her hand guide his head. Now he was both suckling on her clit and inserting he tongue into her Vagina when there – WOW! Ashley gasped and moaned loudly now, pushing her hips into him, grinding her hips as she shamelessly rubbed her Pussy on his face. Wow this deal was going well.
Wow. Good thing Jason was into swimming, because it was all he could do to get a nostril clear to breathe! She was very much into it, and while he had expected her to just lay there while he shamelessly pumped her to fulfill a deal, by her reaction Jason Roberts knew now, he had a tiger by the tail, and damn this tiger tasted good. This young lady was aggressively rubbing her Pussy on his face, and so he kept at it., enjoying how she was moaning saying “Yes-s-s..Ja-a-son…” and pushing her hips in to him. When she started to say “Oh!-I-!-I-!” he knew she was getting close and fact was, Jason wanted his dick in her, plain and simple, so he slowed to a stop, stood, and smiled.
“I should have told you I’ve had a vasectomy.” he said, and he rubbed the circumcised head of his cock on her, and that was all it took.
Ashley Hutchens was a responsible woman, and she was on the pill, otherwise she would have said something a lot sooner, but right now, her body was just responding to the stimuli, so as she had done before, she lifted her rear, pushing her hips out and relaxing, she took his mushroom shaped head in. “Uhh-h-h-h…” she moaned aloud, as she felt the dick she found herself wanting fill her.
Looking up at this man she was fucking, she found herself biting her lip as she felt him thrusting powerfully into her. Pushing herself up onto her elbows allowed Ashley to take the weight off her waist and, feeling him grasp her thighs and pull her open, she wasted no time moving her hips as before, enjoying the sensation of this mans satisfyingly large, fat dick inside her. It felt like it belonged there. She thought how long he would last, and hope it would be awhile.
Being inside Ashley Hutchens was like having your member held by a Hot, wet, pulsating glove. This girl knew her shit, and as she ground those hips to his thrusts, they were quickly making the bed bang the wall, both of us moaning & groaning…DAMN she felt good. The view was incredible. Ashley’s black hose-clad legs were fully open, the garters holding them in place, her breasts bouncing to his thrusts as his cock disappeared in her Pussy while she bit her lip.
It had been a while since Jason had Sex, just due to being a widower but it had been a really long time since he had someone that was moving with him, and that was making him want to pop my cork already. To make it last, Jason slid his hands out to almost her ankles, and spread her legs straight out to each side. At the bottom of the stroke, full-in as deep as he could go, he held and began to work in a circle. It worked, and a whimper plus the look of erotic grimace on her face let Jason know Jason was enjoying it as well.
Her voice and panting changed at Johnathan’s grind, and ‘oh-shit’ it felt good. This changed the angle just right, making his pubes massage her clit, and she called out his name, whimpering with each pant, now having a desperate tinge attached to each. This was not only a surprisingly great fuck, but a challenging one, as Ashley was used to being in control, and things ending too soon. To that end, after she felt him all-in, Kaitlyn now tightened her kegel muscles, squeezing that fat cock with her Pussy as it pulled out. It made her have a devilish grin, and now it was his turn to react, and she was confident he would not hold out much longer, which was both good and bad.
When she applied her Kegels, Jason knew he was on the brink. His voice tightening, his eyes popping out of head were pretty easy clues as well, so Jason applied his last ‘trick’. Going absolute balls deep, he held, then shifted his body up. He felt his slick dickhead press against something. That should be her cervix/G-spot, and instead of thrusting, he began to make slow circles, and tried to hold on just a bit more.
‘Oh no you didn’t!’…Ashley briefly wondered as she felt the large, mushroom head push into…yes…her G-Spot! Damn him, this deal and this man were GOOD. The events of the last hour (or however the hell long it was) and his ‘new’ movements did it. Ashley’s face flushed red, she tucked her chin, and held her breath, but it was no use. With a wail that built into a scream, Ashley Hutchens came, experiencing an incredible, pulsating, twisting & shaking Orgasm.
The experience of giving a woman half his age a gigantic Orgasm was incredibly satisfying. it would be ‘macho’ or cool to be able to say Jason did something impressive next, but the feeling of her Pussy grasp-pulsing on his dick like that was too much, and with an equally mighty roar, he emptied himself into her, letting her pulsing twat milk him of all he was worth. It was a good deal indeed.
**
Now dressed, they both moved a bit limp-legged towards the front. The deal was done, the trade was made, and there was little to say.
“I’ll say, this was waaaay better than expected.” Ashley finally said.
“Yeah, wow it sure was. I thought I went blind when I popped” Jason responded, then added, “I should have struck a better deal.”
Ashley laughed and said “well a deal’s a deal.” She said, and put her hand on the door knob, turning it.
“No-no, I’m a man of my word. What I mean to say is, I should have negotiated a second time, and had a Viagra ready.” he told her.
“So you’re saying that was without…” She started to say, as she opened the door. Ashley Hutchens had the watch in her bag, and was stepping out the door. She’d done it. she had the long coveted watch. But when Jason Roberts said that, she stopped in her tracks, looked over her shoulder and asked, “So you’re saying you have some Blue Pills handy?”
Jason smiled as Ashley closed the door and let go of the doorknob. Meeting her eyes he merely nodded. Good Deal indeed.
****
Hope you enjoyed this! please also check out my other stories, and give me opinion below!
