Chapter 1

Did you ever have one of those days where you just knew it was going to be a rotten day the moment your foot hit the floor? Well, I had one of those days here a couple of weeks ago, myself. Fortunately for me, the day started out shit, but it ended up being a pretty good day after all.

I was leaving my home on the west side of Chicago that day and headed to St Louis. I was already pissed that I had to make this trip at all. You see I am the CEO of a pretty well established and profitable commercial real estate company.

This trip was necessary so that I could check on some properties that some of my agents had been having trouble securing. So it was up to me to come by and reassure the buyers and make this happen.

It was nice and sunny that early spring day and traffic on the I-55 was fairly light. I had taken the company limo and driver on this trip because I was going to St. Louis to make an impression and nothing says success like a black limousine!

This wasn’t one of those long stretch jobs you see the movie stars in or the ones three or four couples use to go to their high school prom, no this was basically just a luxurious Cadillac sedan.

I was making good time, and it would have been a fine trip except for the fact that I had stayed out too late with friends the night before and gotten up too early that morning. On top of the fact that I was still a bit hungover for last night’s fun, I hadn’t felt like eating anything that morning before I left.

Now at almost 11:00 am, I was starving. I kept going on hoping to find someplace to eat soon when I spotted one of those blue and white universal road signs that indicated a restaurant nearby.

I told the driver to take the exit and he followed the signs to a small family-style restaurant named Ethel’s. He pulled into the parking lot and I went inside, while he waited in the car. I stopped first to get a newspaper out of the box in front.

The restaurant wasn’t very crowded, there are only an old man sitting at the far end of the counter nursing his coffee and the cook back in the kitchen. Just as I found a booth and sat down, the waitress came out from the back of the restaurant.

I gave her a quick glance – she was headed to the other side of the restaurant. I looked over the menu to decide what I wanted to eat and then opened the newspaper.

I had just started looking over the day’s headlines when, out of the corner of my eye, I notice someone approaching my booth. A soft feminine voice says, “Good Morning, Sir, can I get you something to drink?”

I looked up and saw the young blonde waitress, standing there smiling at me. She looked to be somewhere in her early to mid-thirties, about 5’4” tall, with pretty green eyes, and what looked to be a nice figure under that none-too-flattering uniform.

“Yes, I think I’ll have a soda. And I’m ready to order too,” I said. She took my order and, smiling sweetly, headed off to turn it in.

I watched her nice, round butt jiggle and shake underneath her hot pink uniform as she walks to the server’s station and fixed my drink. Wow, I thought, What a body!

She really was too pretty to be working in a greasy spoon like this. I went back to my newspaper until she returned with my drink.

“Here’s your soda, Sir. Your lunch should be ready shortly,” she said, smiling again.

“What’s your name, miss?” I asked casually. I like to use people’s names whenever possible ... it makes things more personal and shows I am not just passing through life.

“Michelle,” she said, “My name is Michelle.”

“Well thank you, Michelle. My name is Roger. Nice to meet you, Michelle,” I said. She smiled at the personal contact and went off to continue her work, but as she got a few steps away I noticed she turned her head to glance at me again. I caught her eye and she smiled again, this time with her pencil in her mouth, sort of sexy-like.

A few minutes later Michelle returned this time with my lunch. “Here you go Roger, I hope you like it,” she said. I caught her looking at me with what seemed to me like more than casual interest.

“Thank you, Michelle, it looks very good,” I told her.

As I ate my lunch, I continued to read the newspaper. About halfway through my meal, Michelle came back to check on me and refill my drink.

“Roger, would you mind a little company? It’s pretty slow today and all my work is done for right now,” she asked.

“No, I wouldn’t mind at all, please have a seat,” I said.

“I don’t get much chance to talk to people except just to take their orders. So it’s nice to chat with customers when I get the chance. Are you from around here? I don’t think I’ve seen you in here before,” she said.

“No, I am just passing through. I am headed to St Louis. I live in Chicago,” I said.

“Chicago! Oh, I’ve always wanted to see Chicago! I’ve wanted to see a lot of places actually. I live in on the outskirts of Bloomington and have most of my life. I’ve been to Springfield a few times and once I went to Indianapolis with an ex-boyfriend to see the Indy 500.

But for the most part, I am a local here. I’m sorry if I am a chatterbox, it’s just we get so few outsiders here. So when we do, and I get to talk to them, I tend to chatter like an angry squirrel!

‘I don’t mind the chatter. You have a nice voice and I am originally from a small town myself so I know what you mean,” I said.

“Oh really? Where are you from originally?” she asked.

“You probably never heard of it, I’m sure. A dinky place called Sterling City, Texas. I don’t think there were 1,000 people in the whole town! Of course, I haven’t been there in a while but I can’t see it being a booming place even now.”

“Yes, but now you live in Chicago. You are so lucky! I would love to see Chicago someday!” she said, dreamy-eyed.

“Maybe you will. It’s not that far away ... it’s only about two hours’ drive from here,” I said.

“Yeah, but I don’t have the money for a hotel or anyplace to stay. And I work six days a week here just to make enough to live on. I get to eat here for free when I’m working so that helps too,” she said.

I was about done with my lunch at this point and so Michelle gets up from the table “I’ll go get your check. Be right back!” she said.

I couldn’t help but watch that delectable round ass of hers shimmy as she walked up to the register to figure my check. I resumed reading my newspaper, waiting for her to return. “Here you go, I hope I didn’t talk your ear off too much!” she said.

“No, I enjoyed the company,” I said.

“You’re sweet. Have a nice trip and drive safe!” she said. I left a $20.00 tip on the table and went to pay the check. Then I went to the bathroom before going back to the car. As I came out of the restaurant, I saw Michelle sitting on an old wooden bench sipping on a soda in a paper cup.

“Was your lunch good?” she asked. “Was everything okay?”

I walked over to her “Yes, it was very good, thank you!” I replied.

“I’m glad. Thank you for the tip, by the way. It was very nice ... I could use the money,” she said.

We talked for a bit and Michelle told me that she was off work, but had to wait about an hour for the cook to give her a ride home.

“So is that your big black car over there,” she asked pointing to the limo. It was kind of an obvious statement since there wasn’t anyone else there and certainly no one else with a limo. But I humored her.

“Yes, that’s my car. Or rather my companies car. But since I own the company I guess you could say it’s mine!” I said.

“It’s very nice-looking. Is it a limousine?” she asked.

“Yes, it is. Would you like to see inside it? It’s got air conditioning and it’s a lot more comfortable than an old wooden bench!” I said.

“That would be nice. I’ve never seen the inside of a limousine before,” she said as we walked towards the car. As we got close, my driver got out and came around to open the door for us.

“Who is this?” Michelle asked, surprised there was someone else in the car.

“This is my driver, Paul,” I said, introducing him. He tipped his hat and then opened the door for us. As she got in, I watched her ass wiggle and it was all I could do to keep from grabbing the bouncing globes and rubbing my eager hands over them!

I got in behind her and started showing her the interior of the limo – the seats, the cabinets, and the accessories. She sits on the seat, running her handover the butter-soft leather upholstery.

“This is very nice, Roger ... so soft and smooth...” she said, “I’ve never felt anything so wonderful!”

Now I have to admit, Michelle isn’t the most beautiful woman I’ve ever seen – I have seen a lot of beautiful women in my day and Chicago has more than it’s share of gorgeous females.

But the way her titties were bouncing and that ass of hers jiggled and shook made my cock so hard I could drive nails with it! I figured that if I was going to make a play for her, I’d better do it soon.

“You know, Michelle, I know of a way you could make more money if you wanted to,” I said softly as I looked her in the eyes.

She looked at me puzzled for a moment not saying anything. Then the light clicks on in her head and her eyes fly open wide. “Roger! I’m not a whore!” she said, somewhat angrily.

“Michelle, that’s not what I meant. I know you aren’t a whore and I don’t date whores anyway,” I said quickly.

“Then what DO you mean?” she asked, still cautious. I could tell I had offended her by insinuating she was a whore. I would have to tread gently.

“I just meant that I could be your sugar daddy,” I said.

“My sugar daddy? What’s a sugar daddy?” Michelle asked. “I don’t know what that is.”

“Well, a sugar daddy is a man who spends money on a woman who is his girlfriend or mistress,” I explained. “A whore will sleep with anyone who has the money to buy her for an hour. She doesn’t care who it is so long as their money is good.

A mistress, or ‘sugar baby’ as they are sometimes called, is a more exclusive arrangement. I would give you a call when I was coming through here, and we’d meet somewhere for a while.”

“Hmmm...” she says. “You’d pay me to be your girlfriend?

“Yeah,” I reply. “That’s about it.”

“What about when you are gone? How does that work?” she asked. I mean how often would you be coming through?” she said.

“Well, I will be coming through probably once a month for a while, until I get this St. Louis thing corrected. But I won’t ask you to wait for me. You can have a boyfriend, it’s just that I’d be paying to see you on the side when I did come through,” I explained.

“Well, I don’t have a boyfriend right now ... the boys around here are so immature and childish. It’s like dating your little brother!” she giggled. “So that’s not a problem right now.”

“I see,” I said. This made things easier for me ... jealous boyfriends can be such a pain!

“So just how much would you pay me to be your mistress?” she asked. I could tell by the tone of her voice that this line of conversation had piqued her interest.

“Well, how much did you make in tips today?” I asked.

“Only about $40.00, and half of that was your tip!” she said, dejectedly.

“Well then let’s say $60.00 for today to bring you up to a $100.00 day. And we’ll talk more about it when I come back through in a few days.

“Well ... I could sure use the money...” Michelle said tentatively. “But I’m not a whore!”

“Of course you’re not, Michelle, you’re my new sweetheart! And I’m going to take care of you!” I said with a smile. “Real good care of you, too!”

I handed her three $20’s, and she put them in her purse. “So what do I call you? Sugar Daddy? Roger?” she asked.

“Well, you can call me Roger ... or Daddy if you like,” I said.

“Thank you for the money ... Daddy!” she said with a soft giggle as she began to remove her uniform top. “Umm ... can he see and hear us?” she asked. She was referring to Paul, my driver.

“I can put the privacy shield up if you like, but Paul is discrete. He doesn’t concern himself with what goes on back here,” I said.

“Please ... at least until I get used to this whole thing,” she said. I pushed the button and the privacy screen went up blocking Paul’s view and sound from the back of the limo.

She unsnapped the clasp on the front of her lacy bra, letting her nicely proportioned breasts spring free from their confinement. They jiggled and wiggled about on her chest, but surprisingly, there was no sag at all to them!

“I hope you can keep up with me!” Michelle said as she hurriedly stripped off the rest of her clothes except for her silky panties. “I haven’t had sex in almost three months, and I’m so horny it isn’t funny!”

“That makes two of us!” I said with a smile.

She moved from her seat to come and sit in my lap with her back to me wriggling her tight firm ass in my lap. She felt the large and growing bulge there and began rolling her ass over it, enjoying the way it felt between her ass cheeks.

“Mmmm ... Looks like somebody wants to play!” she said.

I reached around her and pulled her back closer to me. My hands found her full, firm creamy tits and I sank my fingers into the tender tit-meat. Michelle moaned softly as I began mauling her luscious globes.

Her hard nipples poked at my palms, begging to be played with, so I took the little nubs and rolled them between my fingers.

Michelle moaned again louder this time and I learned that her tits and especially her nipples were extremely sensitive and one of her hot spots.

She laid her head back on my shoulder and reached one hand up to my face as I cupped her tits, hefting them and feeling their weight in my hands. “You have wonderful tits, Michelle,” I told her, squeezing them slightly as I spoke.

“Thank you, Daddy ... mmm, I love it when you play with my titties ... it feels sooo good!” she said.

I fondled and toyed with her tits for several more moments, pinching her nipples, tugging on them gently, and sinking my fingertips deep into the pillow-soft meat.

I turned my head and kissed her cheek as she moved her head to the side giving me access to her soft neck. My kisses moved to her neck and then to her shoulder as she groaned, wriggling again on my lap.

Then I moved my hand down to her panties, rubbing her dampening pussy through the smooth cotton material. Her pussy was smoldering – I could feel the heat coming from it through her panties.

I could hear her breathing deepen as she became more and more aroused. She leaned back against the seat and laid her head back, closing her eyes as her legs spread for my hand. As I rubbed her pussy through her panties, Michelle reached up and began playing with her wonderful tits, rolling the tender nubs between her fingers and gently pulling on them, getting them harder and more erect.