Kaitlyn' Good Deal

Kaitlyn Parker checked her phone. "Yes, I'm here, last condo on the right" was all it said. Outside the car there was a 'Clack!' and a hum as the gate to this snobby place for the well-to-do swung open. Kaitlyn put the old Toyota Corolla in in first, released the clutch and rolled into the gated community, feeling a bit out of place amongst the opulence. Kaitlynn had never liked Johnathan Roberts, one of the owners of the firm where she worked. He was always an arrogant ass, albeit a nicely dressed one.

Kaitlynn had always known 'JR', as they snidely referred to him, to be a man of means, and the high-end cars in the drives of this little hamlet certainly proved it. She sighed and shook her head, wondering how such an asshole had gotten ahold of something she had spent years coveting, saving & looking for. Not to mention the deal she'd struck with him to obtain it.

Kaitlyn had worked on the other side of their very successful & profitable office for about 4 years now. She had spent the very large part of it saving to one day 'repay' her dad. Kaitlyn 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.

That damn watch, her dad's only possession of any real value, had paid more than a year of schooling for her two year degree. Kaitlyn had long ago decided she would one day pay her dad back, had been saving since the day she was 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 Johnathan Roberts found out she coveted one.

I had noticed the really attractive little Kaitlynn Parker on the other side of the office a long time ago. She stood barely 5ft/152cm if that; it really seemed to depend on the shoes she was wearing. She had a tight, curvy body, dirty-blonde hair that was mid-back, and a wide smile for such a small face.

Always professional, she worked very hard (or so I always heard) and kept to herself. As she was someone at work, I tried my best to steer clear, but on several occasions, I 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, I had one of those in perfect condition I never wore, and pretty soon, the little head was doing the planning.

Janet, the office snoop, got me the story on the watch, & I let it cool for more than a month, lest I risk tipping off Janet. It only took a 'chance' (wink-wink) meeting away from the office for me to make the offer. Kaitlyn played it cool for sure, because it was almost two weeks later when she got in touch, and the deal was made. I was a bit surprised she went for it, but I wasn't one to let an opportunity go to waste.

And so that was how I found myself on this day, a guy in his late 50's, standing in his upscale condo waiting on a lady literally half his age to show up for a 'trade'. A widower, I spent what little time I wasn't working for the firm either swimming, biking, or working out. So a new way to, umm...'burn off energy' was not only welcome, but in the case of someone so attractive, I intended to make the most of it.

Kaitlyn pulled into the drive, noting he had moved his very nice custom-paint Porsche and some kind of low, classic car under a cover to allow the old Corolla into the shaded carport of the last posh condo on the row, bordering a large pond. She tugged at her new leather skirt and blouse, making needed adjustments due to the seatbelt and the clutch, and put on her new heels. 'JR' was at least generous. He 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, Kaitlyn got out and made her way to the door, seeing that he already had it open.

It wasn't that 'JR' (she had to quite calling him that) wasn't 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. 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, she was never going to get the watch & pay back her dad, and she just could not accept failure. Kaitlyn 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 posh enough.

"Do you have it?" she asked, matter-of-factly.

"Of course." I answered, 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." Kaitlyn asked, as she examined the watch, then put it in her new bag.

"Only ones who will know are those you choose to tell," I responded, then added, "I see you took advantage of the offer regarding clothing. Consider that a thank you gift for the consideration."

Kaitlynn smiled for the first time. "Yes, I will say, it was a nice gesture, and glad you like it. I know I do." 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 your request..."

I let her nudge me back, and had a seat on the couch. Holding a hand up and making a slow 'twirl' motion, I watched as this beautiful creature turned for me. The leather skirt was office-length (what a shame), but she looked mouth-watering in it. She was standing between my knees now, and looking down at me, & 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 my pants, and simply smiled. Turning, she let me lower the rear zipper, and smoothly, she stepped out of them to reveal the matching panties, garters and hose (the panties being notably settled over the garters). So far, it was looking like a good trade.

Kaitlyn was careful with these clothes. She was used to buying at discount stores, 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, Kaitlynn 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, compared to the guys her age. 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 me want to leap of the chair and POUND her, but I was going to get my money's worth (dammit,) so I let her continue the show. She stepped back just a bit more, she was close, so I lightly touched her sexy ass by giving it a kiss. I heard her give a little chuckle, then she stood up, reached back, and released her bra. She turned around, and I finally 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 Kaitlynn liked about showing off her body. She gave him a final 'twirl' and then, taking his hands, she placed one on each breast. Again, Kaitlynn was pleasantly surprised, as he cupped and kneaded her nipples. It was certainly a break from the norm, so she reached down, and pulled his shirt over his head, then the same for his undershirt. Straddling him, she allowed him a kiss.

Kissing this older man 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. Kaitlynn liked that he gave her breasts attention, unlike most of her lovers. Now he had one hand cupping a breast, the other a cheek, and Kaitlynn found herself unexpectedly but pleasantly wet with anticipation.

The taste of her nipples was nice, and they seemed to poke out even more. She moved my face back to hers, and offered me a second kiss, this time with just a bit of tongue. I wanted this girl, no doubt, but not here, I was getting my money's worth, remember? So moving the other hand to her ass, and with a bit of effort, I shifted...moved...(Thank goodness for all the workouts) and stood up, holding her. She wrapped her legs around me, and I walked her back to the bedroom. This deal was going great and I was finally going to give the maid something proper to clean.

Being that she was so petite (just 95 pound/43kg), Kaitlynn was used to getting picked up like this, though she didn't mind it a bit. This old 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 HUGE four-poster, and the sheets were just unbelievably comfortable, even in just her hose and garters. He broke his kiss to strip, and she had no issue helping him.

At last, she got to see the bulge and Kaitlynn couldn't help but notice he was BIG, at least for a white guy. It looked thick & the damn thing was dripping too. Kaitlynn 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, he 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 thought as the kisses made their way up her inner thigh.

I liked that she 'got it' when I was playing-rough. She seemed to melt in to the bed like she belonged there, and I have to say, while Kaitlynn Parker's nipples tasted good, the pussy was incredible. All women have a taste, and this one had a genuine sweetness to her cunt. She had shaved it to a narrow landing strip, so I worked my way down, 'tugging' at her pubes just a bit, before kissing her bright red clit.

I took my time, moving my hands to cup & hold her sexy ass. With my thumbs I slid my hands towards me & eased open her labia, then began to methodically lick down one side, lap the soaking wet vagina just bit, then up the other, to kiss the clit, and start over. Judging by her moans and squirming, she was enjoying it.

"Oh SHIT!" Kaitlynn said aloud. This guy really knew what he was doing! Girls around the office had said that while he kept his distance, Johnathan Roberts was supposed to be very withdrawn since becoming a widower, though a few of the older ladies there had flirted with him. If they had only known, because all she could think about was how he was giving her oral, and his SKILL. Kaitlynn 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! Kaitlynn was moaning loudly now, and pushing her hips into him, 'twerking' her hips as she shamelessly rubbed her pussy on his face. Wow was this deal ever going well!

Good thing I was into swimming, because it was all I could do to get a nostril clear to breathe! She was very much into it, and while I had expected her to just lay there while I shamelessly pumped her, by her reaction I knew now, I had a tiger by the tail, and damn this tiger tasted good. This young lady was aggressively rubbing her pussy on my face, and so I kept at it., enjoying how she was moaning saying "Yes-s-s.." and pushing her hips in to me. When she started to say "Oh!-I-!-I-!" I knew she was getting close and fact is, I wanted my dick in her, plain and simple, so I slowed to a stop, stood, and smiled.

"I should have told you I have a vasectomy." I said, and I rubbed the circumcised head of my cock on her, and that was all it took.

Kaitlynn Parker 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 let him fill her. Looking up at this man she was fucking, she found herself biting her lip as she felt him thrusting into her. Pushing herself up onto her elbows allowed Kaitlynn 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 a satisfyingly large, fat one inside her. She wondered how long he would last.

Being inside her was like having your member held by a hot, wet tunnel. This girl knew her shit, and as she 'twerked' those hips to my thrusts, we were quickly making the bed bang the wall, both of us moaning & groaning...DAMN she felt good. The view was incredible. Kaitlynn's black hose-clad legs were fully open, the garters holding them in place, her breasts bouncing to my thrusts as my cock disappeared in her while she bit her lip.

It had been a while since I had sex, just due to being a widower but it had been a really long time since I had someone that was moving with me, and that was making me want to pop my cork already. To make it last, I slid my hands out to her almost her ankles, and spread her legs straight out to each side. At the bottom of the stroke, full-in, I held and began to grind. It worked, and a whimper plus the look of erotic grimace on her face let me know this gorgeous woman 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, whimpering with each pant, now having a desperate tinge attached to each one. Johnathan Roberts may be old, but dammit this guy knew what he was doing! He was REALLY good at interpreting what she liked and providing it. This deal was getting better by the minute!

Johnathan was not only a surprisingly great fuck, but a challenging one, as Kaitlynn was used to being in control. This was 180 degrees to guys her age, and she was totally into it. To that end, after she felt him all-in & grinding on her, Kaitlynn now tightened her kegel muscles, squeezing that fat cock as it pulled out. She now had the 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 &bad.

When she applied her Kegels, I knew I was on the brink. My voice tightening & my eyes popping out of head were pretty easy clues as well, so I applied my last 'trick'. Going absolute balls deep, I held, then shifted my body up. I felt the head press against something. That should be her cervix, and instead of thrusting, I began to make slow circles, and tried to hold on just a bit more.

'Oh no you didn't'...Kaitlynn briefly though as she felt the large, mushroom head push into...yes...her G-Spot! The events of the last hour (or however the hell long it was) and his 'new' movements did it. Kaitlynn's face flushed red, she tucked her chin, and held her breath, but it was no use. With a wail that build into a scream, Kaitlynn Parker came, experiencing an incredible, pulsating, twisting & shaking orgasm.

I would like to be able to say I did something next, but the feeling of her pussy grasp-pulsing on my dick like that was too much, and with an equally mighty roar, I emptied myself into her, letting her milk me of all I was worth. It was a good deal indeed. Hell, it was the best ever.

**

Now dressed, we both moved a bit limp-legged & staggered towards the front door. Our time was up. The deal was done. The trade was made, and there was little more to say.

"I'll say, this was waaaay better than expected." Kaitlynn finally said.

"Yeah, wow it sure was. I thought I went blind when I popped" I responded, then added, "I should have struck a better deal."

Kaitlynn 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." I told her.

"So you're saying that was without..." She started to say, as she opened the door. Kaitlynn had the watch in her bag, and was stepping out the door, when she stopped in her tracks, looked over her shoulder and asked, "So you're saying you have some Blue Pills handy?"

I smiled. Good Deal indeed.