As I reviewed my latest earnings report, I sat back and reflected on how it all began.

I was just a sixteen-year-old high school student. My parents were filthy rich. My dad was a movie producer, and my stepmother was a shopper. She spent and spent, had no time for me. Hell, she was just twelve years older than me.

We lived in Beverly Hills, one of the wealthiest areas of L.A. 

My stepmother never offered help or direction. My dad was a great father; I wish he had been around more.

The one thing he insisted on was that I learned the value of a dollar. 

I remember how he would buy almost anything I wanted for birthdays and holidays, but if I needed money for makeup, clothes, or going out, I was on my own. I had to earn a living after I turned sixteen.

So, I began babysitting at first, and it paid well. The people in my area were rich, and I was dependable. I made enough to do the things I wanted until my seventeenth birthday.

My dad bought me a car, which was the most wonderful thing that ever happened to me. There was a catch. I had to pay for gas, maintenance, and one-half of the insurance bill.

I was in my last year of high school, and I knew I needed more money, but working in fast food was a big no thank you. I considered a job working in a clothing store, but when I found out what it paid, I realized I would be better off doing more babysitting.

That's when one night changed my direction. I was babysitting for a single father. He was a nice man and told me to help myself to anything in the refrigerator I wanted. If I wanted to, after I put his son to bed, it was okay to use his sauna or swimming pool.

It was a blistering hot day in L.A., and even the AC did not seem to cool me down. 

After putting his son to bed, I decided to jump in the pool to cool down. The only problem was that I had no bikini. 

I thought, what the hell, his backyard was private, and I would only stay in the pool long enough to cool down.

I took off my shorts and T-shirt and jumped into the pool naked.

I swam around for a few minutes, then got out and sat on the diving board, letting the breeze cool my skin.

Suddenly, I heard my name being called, "Chloe. Oh, Chloe, where are you?"

It was Mr. Deacon. He was home early.

I ran to get my clothes inside, but I was too late. As soon as I opened the sliding door, there stood Mr. Deacon.

I tried to cover myself as best as I could. 

Mr. Deacon said, "Oh shit I am sorry. I did not know you were skinny dipping."

I ran to get my clothes and replied, "It's okay, how could you possibly know that is what I was doing?"

He laughed and said, "You're right, and you don't need to get dressed on my account, and please call me Jacob. If you'd like, I'd love to join you for a swim."

I thought he had already seen me nude, and going swimming might get me a better tip.

I dropped my clothes and said, "Okay, Jacob, the last one in is a rotten egg."  

Then I ran to the pool and jumped back in.

He was awkward trying to get his clothes off and fell twice before finally reaching the pool and jumping in.

He was a handsome man with salt and pepper hair and a five o'clock shadow.

We splashed each other for a few minutes, then he asked, "Do you go skinny dipping every time you come over?"

I smiled and replied, "No, just my luck this was the first time. I hope you don't mind." 

He replied, "Mind? I don't think so. Look at my cock I am hard as a rock. Chloe, you are a beautiful woman with a body that is made for sin." 

I could not help myself but to look down at his cock. I began to feel some tingling. Could I let this older guy fuck me?

I swam over to him and took his cock in my hand and playfully stroked him.

I looked at him in his eyes and asked, "Do you like that, Jacob?"

He just nodded his head. 

I asked, "Would you like me to suck it, Jacob?"

He replied, "Oh God, yes."

I took his hand and had him sit on the cool deck then took his cock in my mouth with most of my body still floating in the pool.

He watched me suck his cock and said, "Fuck Chloe you are so good at this. You are a fucking babe. Fuck I want you."

I looked at him and asked, "If I let you have me, what kind of tip will I get?"

His eyes lit up and he replied, “A thousand, no two thousand. How much do you want?"

I did not answer and got out of the pool and sat down on his cock and slowly slid up and down it.

Jacob said, "I just noticed your pussy is bald. I love that. Fuck me, Chloe. Make me cum."

I increased my rhythm, and he watched his cock go in and out of my pussy. His face was turning red, and I hoped I was not giving him a heart attack.

He grabbed me and said, "Fuck I am cumming."

I stood up and he watched his cum drip out of me then I jumped back into the pool.

He followed me in and came and hugged me and said, "I don't even know what to say to you, but that was fantastic. I know this is a stupid time to ask. How old are you?"

I replied, "I will be eighteen soon."

He gulped and said, "No shit you are not kidding?"

I shook my head.

I knew he thought he was in trouble because of my age. If he only knew I did not care.

He got out of the pool and went inside his house for a moment, then said, "Come here, Chloe, I have something for you."

He handed me five crisp new one-hundred-dollar bills and said, "Come by tomorrow night, and I will have some more to give you for a tip."

I said, "Thank you. I probably should get home now. See you tomorrow." 

I didn't sleep very well, thinking about what I had done. Was I a prostitute now? I was no stranger to sex, but somehow this made me feel a little dirty. On the other hand, I thought about how much more he would give me.

 ................................

My phone rang, and it was another client booking my company.

Now, where was I on my train of thought?

That's right, I was remembering this is the night and conversation that changed my life.

I went to Jacob's house around seven pm, and he answered the door, inviting me in.

We sat down and Jacob said, "First thing I want to tell you is that was one of the best days of my life with you last night. You are such a total babe. You are smart, pretty, and very sexy, Chloe. Before I give you the rest of your tip, I'd like to ask if you'd like to do this."

I asked, "To do what, Jacob?"

He replied, "I am not sure you know this, but there are a lot of homes that get broken into in Beverly Hills when people are on vacation. I am going away with my son overseas for a month, and I would like to know if you are willing to house-sit for me. I won't be going for about three weeks, and I will pay you well. You can look at it like a huge tip."

I laughed and asked, "How huge?"

He replied, "I was thinking of five figures provided I get another romp in the hay with you."

I had to think about what he just said for a couple of minutes, then replied, "Is your son in bed?"

He nodded his head.

I took Jacob by the hand and led him into his living room, where I told him, "Now sit on your couch, I want to show you something."

I did not have much on just my shorts and a t-shirt, but I gave him a quick strip show before dropping to my knees and undoing his pants.

I pulled out his cock and teased him by licking it like a lollypop.

I asked him, "Do you want more Jacob? You want my shaved pussy? Tell me what you want."

He replied, "I want you to sit on my cock and fuck me."

I stood up and sat on his lap and very slowly lowered myself unto the tip of his cock. Just letting his head feel my heat, my dampness.

I watched the hunger in his eyes grow. He was focused on my pussy teasing his cock.

I finally slid all the way down onto his cock and rode it very slowly. I was getting wetter and wetter. I wanted as badly as he did.

He grabbed my ass and pushed me up and down on his cock. I was a ragdoll in his strong hands. 

He began pumping me faster and faster. I saw his face turning red like it did at the pool, and I knew he was about to fill me up with his seed.

He let out a loud grunt then filled me up with his cum.

I asked him, "Is that what you wanted, Jacob? Did you like it?"

He laughed at me and said, "What do you think? I didn't like it, I loved it.

He picked me up and sat me down on his couch, saying, "I will be right back." 

He came back with a pile of one-thousand-dollar bills in his hand and said, "That is how much I loved it, and I trust that will be enough for you to house sit for me."

I looked at all the money and said, "Just tell me the dates you want me here, and it's a done deal."

He gave me a calendar and circled the dates for me and handed me a list of things to water for him. He also had a list of maintenance people who come by, such as the pool company and gardeners.

I kissed him and said, "Thank you, Jacob. I promise to do a good job. Time for me to get home. I will call you before you leave." 

When I got home, I counted the money and almost passed out at how much he gave me.

.......................... 

I had to tell somebody about my good fortune. So, I decided to tell my bestie, Grace.

I brought her up to my bedroom and told her, "Have a seat, Grace. I want to show you something."   

I had hidden all the money in a book, opened the book, and let all the thousand-dollar bills fall into her lap. 

With a shocked look on her face, she said, "What the hell did you do, rob a bank?"

I smiled and said, "No, I did not rob a bank. Sit back, and I will tell you how I earned the money."

I went on to explain all that happened, and I would now watch his house for thirty days in the summer. 

After I got all done, Grace asked, "You think he needs two house sitters? For that much money I would fuck him and watch his house too."

I shook my head and said, "I don't think so."

We spent the rest of the afternoon thinking of ways to spend all my money.

......................................

Three days later, Jacob called me and said, "How are you, Chloe?"

I replied, "I am good, and you?"

He said, "The reason for my call is I have a co-producer who is going with me overseas, and he is also in need of a house sitter. It would be the same time I'm gone, and I thought you could spend the night at one house, then the other. If you'd like, I could take you to his house, and you could meet him if you want to. He only lives two blocks away from me."

I replied, "I can do that. When do you want to go there?"

He replied, "How about tonight?"

Then it hit me. Grace could take care of his house.

I replied, "That would be fine. Would you mind if I brought a friend with me?" 

He replied, "Of course not. See you at six." 

I picked up my phone and called Grace.

I said, "Hey, Grace, guess what? Jacob just called me and said a friend of his is also looking for a house sitter. I am going to meet them at six. Do you want to go?"

Grace replied, "I think I do. Do I have to fuck them?"

I replied, "I think it's just a summer job, but I am not positive."

Grace laughed and said, "Okay I will go and if they do want me to fuck them I might. I have not had sex in months and could use a good hard cock. I will be at your house around five."  

Grace came over about five, and I told her, "Grace you don’t have to fuck anyone. I don’t want to be your pimp."

She laughed and said, "I don’t need you for a pimp, I am my own best pimp."

I thought once Jacob saw her, he would want her. She was about like me, little over five feet tall but bigger boobs and dark brown eyes and she shaved her pussy as well.

Jacob was right on time, and when he saw Grace, he began to pant like a dog.

I said, "Jacob, this is my friend Grace. She might want to take care of your friend's house if you think that is okay."

Jacob replied, "My pleasure to meet you, Grace, and I am sure it will be okay with Matt."

We arrived at Matt's house, and he greeted us at his front door. I could tell by the look in Grace's eyes that she would not mind spending some time with him.

He was probably in his thirties, with blondish hair, and pearly whites that were shown off by his mile-wide smile.

Matt showed us both around his house, and this would be an easy job. He had no pets, and most of his houseplants were fake. 

His backyard resembled a luxurious spa. Hot tub, pool, sauna, and a waterfall that was at least ten feet tall flowing into his pool.

I pulled Jacob aside and whispered, "Does Matt expect Grace or me to fuck him?"

He whispered back, "I told him about me and you and he never said anything about it. So, I don't know."

After explaining everything he wanted done while he was gone, Matt invited us to put our feet in the pool and relax. 

Being as tactful as Grace never is, she asked Matt, "Do you want the same kind of service that Chloe gave to Jacob? If you do, would my tip be like his?"

Jacob's face turned beet red with embarrassment. 

I just rolled my eyes before Matt asked, "What service did Chloe give Jacob?"

Grace slid over next to Matt, put her hand in his crotch, and said, “This kind of service."

Matt looked over at Jacob, and he shrugged his shoulders and nodded his head.

Matt then looked over at Grace and said, "Now that depends on how good you are, young lady. I have been known to be a big tipper."

Grace pulled out his cock from his swim trunks and began to blow him.

Jacob watched them, then looked over at me, and I knew he wanted the same. 

I nodded my head and Jacob walked over to me and pulled out his cock.

I began to masturbate him when Matt said, "I think we should take this inside."

Jacob replied, "Good idea."

As we walked back into his house, I grabbed Grace's shirt and slipped it over her head. She stopped and pulled off my shorts exposing my bare ass for both guys.

By the time we got inside, we were both naked, and Matt and Jacob were not far behind us, taking off their clothes.

Matt said, "Have a seat on the couch, ladies. We are both very hungry."

We sat side by side as Matt spread Grace's legs and began to munch on her pussy. Jacob did the same thing to me.

I looked over at Grace and knew she was in heaven. She had never had a man like Matt before.

I leaned over and decided to give them a show they would not forget and began making out with Grace. Our tongues darted around our mouths.

Simultaneously Matt and Jacob stood up and put their cocks into us.

Grace looked up at Matt and asked, "You like fucking my young pussy? You going to cum in me?" 

Matt nodded his head.

Jacob was going back and forth watching his cock going in and out of me and watching Matt fuck Grace.

Jacob asked me, "What do you think about trading partners for a couple of minutes?"

Before I could even say a word, Grace said, "Go for it."

The next thing I knew I felt Matt put his cock in me and pumped me like a madman. 

I saw Jacob slide his cock into grace and slowly fucked her. 

I didn't know what kind of tip we would get, but it better be a big one. 

Matt kept fucking me and then Jacob said, "Lets bend these two over and fuck them doggie style."

Matt flipped me over and pulled my ass towards him then shoved his cock back into me.

 Jacob went slower with Grace, and she bent over on the floor so he could fuck her there.

Matt said, "I am close, let's switch again."

Matt barely got his cock back into Grace before he shot his load in her and on her ass.

Jacob saw that and then filled me up with his cum a minute later.

Matt fell into a slump on the floor and looked at Grace, saying, "You're hired."

Grace laughed and said, "Okay, big boy, where is my tip?" Then held out her hand.

Matt asked, "Would a check be, okay?"

Grace answered, "I don't think so. How would I explain that to my parents? I am only seventeen, and they see my checkbook. So, cash please."

Matt looked over at Jacob and asked him, "Are they both seventeen?"

He just shook his head. 

You could hear Matt mumble under his breath, then say, "Okay, no problem. Come by tomorrow night and I will have your tip."

.......................................................................

I took a sip of my Coke and thought back to that night. What a crazy way to start a business. I remember Matt giving us both a six-figure tip.

I then remembered my conversation with Grace the following day. 

I told her, "You know what, Grace? I have an idea. What if we found some more houses to take care of? We would be rich by the time we are twenty-one."

 She laughed at me and said, "You want us to be call girls? We would get busted sooner rather than later. I don't think so."

I replied, "That's not what I mean. What if we just took care of people's houses while they are away, around here? You know a real business. If we fuck them once in a while for a big tip that would be okay too.

.............................................

That was the day we made a company.

I remember taking care of Jacob's house, and I helped with Matt's house for that month.

Jacob and Matt were pleased with our work, among other things. They gave us the names of a lot of their friends.

Grace and I had a stream of clients who traveled. Most of them were in the motion picture business, like my dad, Jacob, and Matt.

We decided to establish a company with a name and all the necessary details in place. We came up with "House Sitters Inc."

We got so busy that we had to hire some help. We also knew that with hiring anyone, there would be no mention of sex, nor would we allow it. We did not want to go to jail for running a prostitution ring.

We hired three of our female friends, who were all attractive, and two male colleagues to cater to the female clients who wanted a little eye candy.

My dad was a big help with our business. He got us hooked up with an accountant and a lawyer. He never figured out why we had so many clients and made so much money.

...................................................

A year into our business, and it was going great.

One day, Jacob called and asked, "I am having a bachelor's party for a dear friend, and I am looking for some entertainment. I am looking for several women to strip at the party, and maybe more. Would you and Grace want to do it? Do you know of any other friends who might want to join us for a party? I promise you will make more money than you ever dreamed possible. Most of the guys that will be there are billionaires and want discreet fun. If you don’t want to fuck them that’s okay but you won’t make as much money. So, what do you say?" 

To be continued