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.
