tagErotic CouplingsThe Waitress

The Waitress

byshowife©

Although the person and place are real the rest is a fantasy.



I've known Kathy for over 10 years, well not really known her personally, but rather as a casual acquaintance for the most of those years. I really haven't gotten to know much more than her name until the past 2 – 3 years.

There's this small town, by small I mean less than 400 people, where there's a little restaurant where I often stop for breakfast or lunch. For the first many years it would only be once every month or two but for the past years it's been almost every week. I stop more frequently now since I have to travel through this little town to check in on one of my investment properties that's about an hour up the road from there.

However, back to Kathy and how we got to where we are today. The very first time I went into this little place to get some food the main attraction was Kathy. Well it wasn't her so much that got my attention at first but when she walked away from me after taking my order it was a delight to watch.

She just had the nicest shaped ass I had ever seen! She's quite a thin women, I'm sure about a size 4 jeans and 32A bra, but her ass is that shape so many of us can spend hours admiring. How can I describe it? It looks much like an upside down Valentines heart or two halves of a peach? Definitely not big, not drooping, and not sticking out, but just sweet, very nice.

That didn't really mean much to me until recently but every time I stopped in to get some food I always enjoyed the view but never did anything more about it until a couple of years ago. Since I had become a regular customer she'd started to call me by name and was always happy to wait on my table

Over the years I'd seen her age but her ass always looked great and looked to still be nice and tight. One year I'd seen her with a black eye, a few weeks later she'd taken off her wedding ring and then told me about her divorce and the difficulty of raising young teenagers.

Things changed about a year ago when she was cleaning off the dirty dishes at the table next to where I was sitting and as she was bending over to wipe off the table she realized that her ass was pointing right at me. She stood up and muttered some kind of apology about her posture but before she could say much more I blurted out something like "don't worry I could look at your ass all day."

That made her blush even more and I thought that for sure I had offended her and she would think of me as some kind of perverted jerk. However, the next time I came in for lunch she greeted me like nothing had ever happened and our usual banter went on as it always had.

But over the next several visits to the restaurant I did notice one big change. Every time I was seated at a table Kathy would seem to make an effort to face away from me and bend over while cleaning up the next table, and even while serving food or coffee to the other table.

It wasn't too many weeks later that I decided to raise the stakes a bit and after she left the tab for the meal on my table I wrote on the back "Thanks, Nice Ass!" and left the cash and her tip on the table as I usually do.

The next week when I came in she seemed to be a little bit flustered but when she came to my table with coffee the first thing she said was "Thanks, and do you really think so?" Since the place was pretty empty I told her that I'd noticed her ass the very first time I'd come into the place and it was one of the reasons that I enjoyed coming back every week.

Needless to say this changed our weekly exchanges and although we both flirted with each other we never really acted on it. Well except I did take the opportunity one time to squeeze behind her in the narrow hallway to the bathrooms and was able to get a good feel of her ass and at the same time she was able to feel how "hard" my appreciation was.

Shortly after that quick little feel I stopped in the restaurant and to my surprise there was a large "FOR SALE" nailed to the outside of the building. Kathy explained that the owners were old and bad health was forcing them to sell the business and retire.

Over the next couple of weeks I asked her why she didn't buy the place, but the excuse of "no money" was all she could tell me. The weeks turned into a couple of months and still no offers had been given for the property. I guess nobody wanted to invest in such a small town. Kathy did say that she tried to buy the place and even had some ideas about improving things but that when she'd talked to the bank they had turned her down.

After I left that day I checked into the business and the property to see what hey wanted for it. I really didn't want to own a small town restaurant but was curious.

I was surprised to find that the whole place was for sale for what I thought was a small amount of money. In fact after running the numbers, with the level of business remaining the same as it was now, it would just about be paid for in 5 years and even then it would still turn a profit during that time.

Of course by then my devious mind had a plan in place so I submitted and offer as an anonymous buyer, with just a few conditions and it was accepted that day. Now I needed to move forward and see if the deal would come together, or if it would fall apart.

The next week when I stopped in the big sign now said "SOLD" and Kathy was eager to explain that an out of town buyer had bought the business but everyone was convinced that they were going to lose their jobs, or that something bad was going to happen to their livelihood. She explained that the employees were going to meet the new owner, and at least she was supposed to meet them in about 30 minutes.

Since I'd already had an after hours tour of the building I knew that there was an office in the back of the building that had both and inside and outside entrance and had arranged to have the meeting with Kathy in the office. After getting my breakfast to me she excused herself to go and wait for her new boss to show up.

I waited a couple of extra minutes and as always paid my bill and walked out to the parking lot, but instead of leaving I walked up to the outside office door and let myself in. Kathy was sitting in the desk chair and when I came in she was confused and it took awhile before she realized that I was the buyer.

I handed her a folder that contained the purchase agreement, and the conditions for the sale that needed to be met before the sale was final. Basically I would only buy the business if she would stay on as manager for a term of at least 3 years. She would receive a 25% increase in pay and also receive 25% of all profit that the business generated. She really looked happy as she read the details and seemed like she wanted to sign the papers right away.

However when she got to the final paragraph she paused and looked perplexed. It simply said that all this agreement was conditional on a "personal service agreement" with me that she also had to sign. She looked up at the paper I was holding and when I asked her what do you think I want? She smiled and said "you want my ass don't you?"

I handed her the last page and the requests were quite simple. At least once a week she would willingly give me her ass, her cunt and her mouth for my sexual pleasure to do with as solely as I desired. In addition to the weekly meetings I would require her to spend 6-8 weekends with me where she would attend to whatever I wanted in a sexual matter. This could include but not be limited to the previously mentioned sexual activities, serving as a hostess for parties, either clothed or nude, posing for nude photos or movies, and having sex with whoever I asked her to accommodate.

She swallowed a bit hard at the last words but after some thought said that I could have had her any way I wanted without having to buy the place. I already knew that but thought this was much cleaner and would carry less emotional baggage for the next 3 years. She then offered to sign the papers, but I explained that they needed to be notarized and I would pick them up next week. This would mean that at least one other person, the Notary, would know that she had signed up to be my sexual slave for the next 3 years.

To my surprise she asked if I'd like to seal the deal, and have a taste of what the future will hold? After a quick yes from me I instructed her to stand and start to undress. She stood up from the desk chair and slowly began to unbutton her shirt. I was pleased to see that she was calm and as she pulled off her shirt she even smiled as she reached behind to unhook her bra.

She apologized for the little tits but didn't hesitate in removing her bra and showing them to me. I was happy to see that she had soft pink nipples and that although her tits were little they were still nicely shaped and didn't have much sag to them at all. I guess that gravity is less of a problem for women with small tits.

She stood there and waited until I waved her on to continue and after taking off her belt and unfastening her pants she pushed her jeans and her panties off at the same time. Once again I was pleasantly surprised to see that she was indeed a real blond and also that her pussy had just a thin covering of hair.

Once she stepped out of her clothes she just stood facing me as I looked her up and down. She didn't seem embarrassed at all but just watched me as I looked her over. I asked her to bend over the desk and I moved around behind her to finally get a look at her ass. All these years of looking at it walking away from me and now here she was bent over the desk showing her bare ass to me.

I quickly dropped my pants and started to squeeze and knead her little ass. Soon was also pulling apart her cheeks and running my cock up and down the crack between her sweet ass cheeks. She told me that she hadn't had anal sex more than a couple of times and that it was a long time ago.

However I had come to this meeting prepared and I quickly lubed her ass and started to explore her ass hole. I could tell that it was going to be tight, it was evident she wasn't used to having anything shoved in her ass. But that would all change soon.

I told her that I was going to fuck her in the ass and she told me to go for it, and that she wanted it too. It was slow and easy and after a few thrusts had still managed to get about half way into her ass. She was doing the best she could to let me use her but I could tell from the way she clenched her hands that it was difficult for her.

She was encouraging me to push harder and get it all the way in so I grabbed he by the shoulders and shoved my cock all the way into her ass in one quick move. My balls were now up against her pussy and I could feel that she was turned on as she was very wet.

I waited a few moments and then pulled almost all the way out and after a pause plunged all the way in again. She gasped and pushed back against me as she was really doing her best to give me a good fuck with her ass. I realized that today wasn't the day this was going to happen and after a few more, but less vigorous, pumps in and out of her ass I pulled out all together.

Much to my surprise she was crying when she stood up and I figured that she must really be hurting but instead she was saying how sorry she was and that she really wanted me to fuck her ass, and now I wouldn't buy the business, and she wouldn't be able to make more money and on and on.

Finally she quieted down, actually she looked quite nice standing there naked and crying about not being able to please me, and I explained that this didn't change anything. I would buy her some butt plugs so she could work on stretching out her ass and that I would enjoy fucking her ass many times in the future. I also reminded her that I had plans for her for the next 3 years and that today was just the start of our business relationship.

She finally stopped crying and hugged me and asked "now what". I asked if she was any good at sucking cock? For a response she dropped to her knees and in less time than it takes to think about it had swallowed almost the complete length of my cock. Not only was she a good cock sucker but she could deep throat as well! This was going to be enjoyable!

It wasn't until she was well on her way to getting me to cum that it dawned on me that she had taken my cock in her mouth without any hesitation even though just moments before it had been shoved all the way into her ass. She later told me she didn't think about it until she had already sucked it in and by then she figured that it was something I wanted her to do anyway.

I told her when I was getting ready to cum and that I wanted her to take my cum on her face. She just nodded and as I pulled out of her mouth she positioned herself under my cock so that every drop of cum was between her eyebrows and chin. Nothing missed its mark.

I must say that she looked great with a face covered in cum and quickly took out my cell phone and took a couple of photos. I explained that I would be back next week to pick up her contracts, both for work and for sex, and bring her the butt plugs at the same time. She was still kneeling on the floor, naked, with her face covered in cum and as I went to the door she said "Thank you for a future."

As I walked away I was already thinking about what the next weeks and months would have to offer.



Ok, if you've gotten this far you've made it through the story and I'd appreciate some feedback so email me. Too much background? Not enough sex? Write more as it could get interesting" Let the story die?

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