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!" she said.
"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," I told her.
"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 sat on the seat, running her hands over 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 her's 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.
Seeing that Michelle was in her own little world, I took the opportunity and slipped my hand under her panties to find her soft, trimmed mound. A little further down between her spread thighs, I searched for the source of her heat.
A surprise awaited my probing fingers– Michelle had a very unusual pussy! Her clit stuck out of the blond fur of her pussy like a little cock. As I moved my hand down lower, trying to find her opening, I felt her pussy lips dangling down. They were meaty–almost as long as my finger is across, swollen and blistering hot to the touch.
"Ohhh, Daddy… please, please play with my pussy!" she whimpered softly. Well, she didn't have to ask twice! I slipped two fingers into her molten depths, splitting them slightly and running one on either side of her extended clit to capture it between them.
I curled my fingers around her pubic bone and began pumping them slowly in and out of her. She was already very wet and in the confines of the back of the limo, the squishing sound was quite loud and made it all the more erotic.
With her sitting on my lap, half reclined into me and my left arm wrapped around her left side and grabbing her right tit while my right hand played with her sopping cunt, Michelle was in heaven. I held her as I masturbated her bringing her closer and closer to the edge.
"Oh, Daddy! Ohhh you're gonna… you're gonna make me…. cum…" she moaned as she grabbed the arm across her chest. She shook her head back and forth as her passions began to take control of her. I could feel her trembling as she fought to control what threatened to consume her.
"Do you want to cum? Do you want to cum for Daddy, sweetheart?" I growled into her ear. To emphasize it I increased my pressure on her pussy and clit.
"Ohh yes! Please Daddy, please make me cum! Make your little girl cum, Daddy! Pleeease!" she cried. I knew that it was only moments away, I could feel her starting to break. Calling me Daddy and talking like this was wearing her defenses down rapidly.
"Okay baby, give Daddy a great big cum. Cum for Daddy NOW!" I said. And with a great cry, she exploded. She gripped the arm across her as I held her to me tightly. She tried to thrash around and writhe but she was restrained and that only seemed to add to the intensity.
Being held by 'Daddy' while she was in the throes of a wonderful orgasm seemed to make it even better. She flooded my fingers as I toyed with her large clit, sending waves of pure pleasure coursing through her.
I held her as spasm after spasm wracked her body, until finally, she was still, panting and sweaty in my arms. An occasion shudder told me that her mind was still reeling so I just held her for a few moments as she purred contentedly.
"That was wonderful, Daddy. Thank you for my cum. I haven't had a good one like that in too long!" she said weakly.
"You are welcome, sweetheart. I like making you cum," I said.
"Yes, but now it's your turn and I want to see you cum! she said sitting up. She slid off my lap onto the floor of the limo, turning to kneel in front of me.
I felt her hands unbuckling my belt and unsnapping the button on my pants. "Let's see what Daddy brought for his new girlfriend to play with," Michelle said as she began to pull my pants down.
I tried to help her work at undressing me in the confines of the limousine. I kicked my shoes off, and Michelle pulled my shorts down, and as she did, my thick eight-inch cock quickly sprang out.
"Oh my! What a big one!" exclaimed Michelle, clapping her hands with delight. "Looks like you're more than ready! Sit down here and let me have a taste!" She patted the seat beside her.
I finally got out of my pants, sat down on the seat, and leaned back a bit against the back wall. As I did so, Michelle climbed between my spread legs, her breasts lightly skimming across my cock and causing it to throb with anticipation.
"Mmm! We're gonna have a lot of fun! I'm going to make you the happiest Daddy in the whole world!" Michelle promised as her hand began to gently stroke up and down my rock-hard cock. "Now you just lie back, Daddy, and let me play with this big fat cock!"
A small drop of pre-cum had formed at the tip of my cock as Michelle ran her hand up and down my shaft. She lowered her mouth and quickly licked the cum off the tip.
"Mmmm… delicious!" she said smiling devilishly. Then the most marvelous sensation enveloped my cock, as Michelle began feverishly sucking my cock.
"Ohhhhh," I softly moaned as she began bobbing her head on my cock. "Ohhhh, yeah!"
Michelle fervently licked the head of my cock as she softly stroked the shaft with her hand, jacking me.
I slid my hands under her to play with her hanging tits and heard her coo with pleasure. "Mmmmm…" she purred with my cock in her mouth, making it tingle with delight. "Mmmmmm!"
I lightly brushed my fingers across her hardened nipples, and she sucked my cock with a newfound vigor. Michelle was a good cocksucker, but she didn't deep throat me just yet–she only took about half of my length in her greedily sucking mouth.
But I didn't mind, she more than made up for it with enthusiasm!
I continued fondling her wonderful titties, rubbing my hands over them, feeling their firmness and their creamy softness. I gently rolled and pulled on Michelle's tender nipples with my fingertips. I massaged her tits until Michelle suddenly stopped slurping on my cock and asked: "You like my tits, Daddy?"
"Yes I do, very much!" I said. "They're nice and big, just the way I like 'em!"
"Scoot down a bit," Michelle said as she tugs on my legs. I quickly complied, and Michelle scooted further between my spread thighs, getting even closer to my cock.
She took her breasts, one in each hand, and placed my cock in the soft valley between her two large tits. Michelle began moving her tits up and down, fucking my cock with her full titties.
"Ohhhhh yeah!" I heatedly moaned. "Ohhhhh fuck that's good!"
"You like that, do you?" Michelle asked in a lusty voice. "You like fuckin' my titties with your big cock, Daddy?"
"Ohhhh yeah!" I replied. My hands were gripping the sides of the seat, my knuckles turning white with the effort. Michelle rubbed her tits up and down on my cock, and when it started to get a little dry, she quickly swooped down and sucked on my cock, making it nice and wet with her spit.
Her tits were amazing; warm and pillowy-soft, and the valley between them was slick with her saliva and the pre-cum that was copiously oozing out of my cock. "Mmm… I like this!" said Michelle. "I like you fuckin' my titties with your big cock, Daddy!"
Her nipples were rock-hard and poking me in my nut sack as she rubbed her wonderful titties over my cock, and sucked on the purple head of it.
Up and down her head bobbed on my shaft, licking and sucking my cock, then stroking my cock through the hot valley between her tits, until I couldn't hold back anymore.
"Ohhhhhh, sweetheart, I'm gonna cum!" I gasped. "Daddy's gonna cum! Ohhh yeahhh!"
My sack drew up against my groin as my balls began to pump their heavy load into Michelle's hot mouth. But before they could dump their sweet hot load of cum, Michelle had another surprise for me!
She clamped her thumb and index finger around the base of my cock, gripping my cock firmly, and pinching off my urethra running up the underside of my cock. My nuts tried to pump their contents out of my cock, but they were blocked!
Michelle continued sucking on the head of my cock as I came, and the sensation was unbelievably intense! My cock and nuts twitched and pulsated, but nothing came out of the tip!
Michelle kept licking and sucking on my cock as my nuts strained and struggled to pump out their milky-white contents, to no avail. Michelle sucked and licked the sensitive underneath of my cock head until my orgasm was finally over.
"Let's fuck, Daddy!" Michelle said as she pulled her lips off of my cock. "I haven't had any cock in weeks!" Michelle let go of the base of my cock, and to my surprise, almost no cum seeped out of my cock–I guess it went back to where it started from.
She climbed back into my lap, but this time before she sat down she reached between her legs and gripped my cock, pointing the tip at her hungry, juicy pussy. She rubbed the tip along her length, lubricating it before easing the mushroom head between her fat pussy lips.
"Ohhh, Daddy!" she moaned. "Oh, your big cock feels so good in my little pussy!" She slid down my shaft very slowly, enjoying every inch of me as I opened her up. My cock easily slid into the hottest, wettest, and tightest pussy I can remember ever having!
Her pussy muscles rippled around my cock, and it felt like a tight velvet vise squeezing and throbbing around my cock. I slid my cock in as deep as it would go, and my balls pressed against the cheeks of her luscious ass as I buried my entire nine inches in her.
"AAAAaaaahhh," I groaned as an involuntary moan escaped from my mouth. "Oh damn, that's good!"
"You like that, Daddy?" Michelle asked in a husky voice. "You like my tight little pussy, Daddy?"
"Oh yeah!" I moaned.
"Ummmmm, then fuck me, Daddy, fuck me with that big fat hard cock of yours!" she cried. She reached up to grab hold of the two hand straps over each door using them to hold her hips just a couple inches off my lap, allowing me to stroke in and out of her.
I began to slowly stroke my cock in and out of her warm syrupy wetness, and as I looked down to where our bodies are joined, I could see her fat pussy lips clinging to my cock as I withdrew.
They almost looked like two big, pink windshield wiper blades – wiping the juice off of my cock as I pulled back, and then smearing her syrupy girl goo back on it as I pushed my cock back into her snatch.
My cock slipped out of her snatch, and I took the opportunity to rub it up and down against her swollen labia and feel their silky smoothness on the shaft of my rock-hard cock.
Her pussy lips were red-hot, and they were so large that they wrapped around the shaft of my cock as I slid my cock up and down her juicy slit. I slipped the head of my cock back in her cunt and got a good coating of her oily juice on it.
Again, I pulled out and rubbed the shaft of my cock up and down her gash, relishing the feeling of her sizzling pussy lips wrapping around my cock, her abundant blonde fur tickling the head of my cock, and the warm sticky juice steadily flowing out of her twat and over my cum-filled balls.
"Ummmm!" Michelle moaned loudly. "I like the way you make me feel all tingly inside!"
I slipped my cock back into her slick tunnel and slowly began stroking in and out, in and out of her tightness. I've had many women in my time, but I've never had one that was as tight as Michelle! Her pussy seemed to have a life of its own as it massaged and kneaded my invading cock.
Michelle's tits wobbled about on her chest, her nipples pointing skyward like two big pencil erasers, as I fucked my cock in and out of her tight and juicy snatch. I rubbed my hands up her sides to her tits, playing with them even as I drove my cock into her cunt.
"Are you ready to cum for me?" asked Michelle with a lewd smile on her face.
"Huh? Am I what?"
"Are you ready to cum? I can make you cum anytime I want!"
"How?"
"Like this…" and before I knew what she's doing, her pussy seemed to get even tighter around my cock! The muscles inside her spongy pink tunnel rippled and fluttered around my cock, and before I knew what's happening, she was right–I began to cum!
It wasn't like a typical climax, either, shooting spurt after spurt of cum rapid-fire into her hot box. This was more like one continuous burst of cum, almost as if I was pissing instead of cumming.
There was a strange and unusual sensation in my nut sack–like toothpaste being squeezed from a tube! My balls seemed to have a never-ending supply of cum to offer up to Michelle's wonderful snatch, it just kept flowing out of my cock and into her pussy. My cock felt like a garden hose, and I was watering her twat with it!
"Ohhhhhh…" Michelle purred as I came inside her. "Ummmmm! That's so damn good!" She wiggled her hips a little, and my cock slid around inside her tight pussy. "Shoot your cum in your baby's pussy!"
I pulled Michelle down hard onto my lap, pressing her hips down as I tried to bury my cock as deep in her pussy as I could. After a bit, the sensation quit, and I no longer felt like I was streaming into her twat. Michelle lifted herself up and off me so she could turn around and suck what cum was left in me, cleaning my cock off with her mouth at the same time.
Then she moved closer between my legs resting her head on my chest as she knelt there between my spread legs.
"That was wonderful, Daddy. Thank you for making me feel good," she said. "And thank you for being my Daddy. I think this is going to be so much fun! I want to be a good baby for you and make you happy, Daddy"
"I think it's going to be fun too. And I can hardly wait to come back through and see you again. But right now, Paul and I have to get going if we are going to make St. Louis. And it's about time for your ride to take you home as well," I said.
"Yeah. When do you think you will be coming back through here?" she asked.
"Oh, it will probably only be a few days. I am hoping to come back sometime this week," I said.
Michelle took a pen and wrote down her phone number and the number of the restaurant. "Here is my phone number and the restaurant's number. Give me a call when you are headed back this way so I can be ready to see my Sugar Daddy again!" she said, smiling.
"Oh, you can count on it, sweetheart!" I said with a big grin. I helped her out of the car and walked her back to the wooden bench to wait for the cook to take her home. I gave her a long, passionate kiss.
"Call me when you get to St. Louis so I know you got there safe," she said, softly looking in my eyes.
"I will. I promise," I said, then turned to walk back to the limo and I left with a waved goodbye as I headed for the highway.
