I have my own small legal office downtown Las Vegas. I hire a lot of legal assistants that are coming out of college. I hired a gal recently that is older, she had good credentials as a paralegal. Her name is JoAnn, a sexy 53yo gal with a body of a 25yo.

I had never screwed around with any of my assistants, even though there were several times it crossed my mind. I learned a long time ago screwing someone you had to work with could cause a lot of problems down the road.

Anyway back to JoAnn. She was a great employee and with past experience I didn't have to spend most of my days going over all of her work like I had to do with the girls fresh out of college. JoAnn knew what to do and how to prepare the legal forms and saved me a lot of time to do the other things needed to be done.

Well about eight months into the job, JoAnn began to have money problems. Las Vegas is famous for people gambling their paychecks away. Long story short, I helped JoAnn out. I would front her paycheck frequently and then it became even more. She had become a financial train wreck basically, and I realized I was only enabling her.

Now I'm a single guy and have been careful with my money, I'm not rich by any means but I have enough security in the bank to be okay. So I began to give JoAnn money for just about anything, rent, car payment, etc.

One evening at work I realized I was going to put an end to this mess. JoAnn wasn't ever going to get her life together and I would eventually go broke paying for all the shit she couldn't cover.

It was just after 8pm when I decided to call it a day. Suddenly I heard someone at the front door of the office. Since I was downtown it wasn't unusual to see drunks and homeless people roaming around after dark.

Just as I came out of my office to the lobby area, JoAnn was coming through the front door, she did have her own key to the building that I had given to her when she first started working.

Before I could say anything she turned and gave me this big smile. Her arms were full of things and I went over and took some of them from her. She told me she had brought me dinner as she walked past me and went into my office.

The first thing that caught my attention was the way she was dressed. Very petite dress and her high heels echoed off the hardwood floors. The next thing was her perfume, no idea what it was but I liked it!

I followed her a moment later into my office. JoAnn was bending over my desk placing paper plates and other items on my desk, I couldn't help notice the sexy little dress she was wearing was riding high up the backs of her shapely legs.

JoAnn heard me walk in and she turned to look at me quickly. She was wearing quite a bit of makeup, normally she wore the basic at the office. Tonight her eyes were framed in mascara and liner, her lipstick had a shiny gloss to it as well.

She came over and took my hand and led me around to my desk. Once seated she walked around the other side and pulled out a candle and sat it down. JoAnn walked over to the far wall and turned the overhead fluorescent lights off. For a moment the only light in my office was from the street lamps outside the building, JoAnn lit the candle she had placed on my desk.

JoAnn had brought deli sandwiches and some other items. It was her way to thank me for all the help I had been. I tried not to think how this compared to the money I had "loaned" to her, but it did creep into my mind as we ate. JoAnn pulled a chair to the the side of my desk and we had the candlelight burning between us.

The glow of the candle really set her makeup off, I found myself staring at her eyes and the gloss lipstick made her lips look like liquid. As JoAnn talked I barely heard a word she was saying, for the first time I was thinking about JoAnn in a sexual manner now.

At some point one us came on to the other, maybe we both did at the same time? All I know I had the taste of JoAnn's lipstick on my tongue. I kissed her hard and felt my cock rising to the occasion quickly.

I fondled her breasts in the soft glow of the candlelight and JoAnn moaned with approval as I squeezed them with another kind of hunger. JoAnn pulled away a few moments later, her face was slightly flushed. She put her hands to my shoulders and pushed me back slightly until I bumped against the edge of my desk.

I watched in silence as she unzipped my pants and pulled out my throbbing cock. JoAnn knelt before me and began to suck my aching cock. Within minutes her mouth had worked me up into a hot lather. I really wanted to let her have it down her throat, it had been a while since I had been with anyone and I was more than ready to cum. What was left of JoAnn's lipstick after our makeout session was now on my pulsating cock.

I reached down and took her wrist and pulled her up against me. I lifted up the back of her dress and cupped my hands on her ass cheeks and squeezed them. JoAnn moaned into my shoulder as I grinded my hard cock against her pelvis.

I took her over to the sofa against the far wall and lay her down. JoAnn slid her thong panty off as I peeled my clothes away. Without undressing JoAnn I just pushed her sexy little dress up and entered her. JoAnn was soaking wet and I easily buried my hard cock into her pussy.

I fucked her almost savagely and JoAnn seemed to enjoy it. She wrapped her legs around my waist, her heels digging into my sides. JoAnn moaned with pleasure just as I'm sure I did but didn't notice. She told me to keep fucking her, which that was going to happen regardless.

JoAnn clawed my back as she came again, the erotic pain seemed to arouse me even more. I just took her anyway I wanted, flipping her over onto her fours I took JoAnn from behind. I held onto those shapely hips tightly as I felt the twinge of impending release.

I reached under and took her breasts, squeezing them through the material of her dress. There wasn't going to be time to enjoy her bare breasts this time, I was already beginning to shoot my hot load into JoAnn.

I lay on top of JoAnn for a few minutes after I came, I could feel her moving in some way and realized she was fingering her drenched pussy. Not one to leave a woman unsatisfied I flipped JoAnn over onto her back and shoved three fingers into her cum filled pussy. She bucked and squirmed with pleasure, biting her lower lip as she climaxed again.

At some point she reached down and pushed my hand away, letting me know she couldn't cum another time. I squeezed in behind JoAnn on the sofa and we both dosed off for a bit.

I heard her heels on the floor at some point, JoAnn was trying to walk to the bathroom on the other side of the lobby. Just watching her walk was starting to get me aroused all over again but I let the moment pass.

So I am paying for the most expensive piece of ass I have ever had. Nothing much has changed JoAnn still needs money often and I'm there to give it to her. In return we fuck whenever the time presents it's self.............
































Comments

Anonymous

by Anonymous on May 26, 2016 at 3:28 PM

I'm a 55 year old male who enjoys hobby girls. I was fucking a 23 year old red head who was hot and slutty and really broke. I started lending her money as she was homeless. In return she would fuck me extra whenever I wanted. Like you I've spent more than I've gotten but at least she is still alive. She got arrested 3 months ago for an old warrant and I'm still supporting her in jail but it is a lot cheaper! Crazy.

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Anonymous

by Anonymous on May 27, 2016 at 12:52 AM

Why pay someone who basically is an expensive prostitute when there's lots of free sex about?

(0)  (0)
Anonymous

by Anonymous on May 27, 2016 at 3:10 AM

Point me to the free sex pool please. I would appreciate it.

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