I live in a small town somewhere South and East of Lexington, Ky.
There is nothing small about Lexington and I end up there a lot. Perhaps too much, but then work takes me there on a routine basis. I get a lot of overnights in Lexington. There are multiple theaters, fine places to dine and a good selection of dance floors, bars and other hangouts. I'd like to admit to a puritan life style and tell you I never frequent such places. Of course, I'd be lying, so why bother?
I got to all those places, some more than others. I enjoy the secret feminine pleasure of allowing a man to buy my dinner, hold my chair, pour my drink and select my wine for the evening. Sometimes the men will get a reward. Sometimes they do not and that is completely up to me to decide. A man can spend $250 on a dinner date, a movie and a small gift if he chooses. He might get nothing while the guy who is charming, plays himself well and treats me to nothing more than a great grilled burger at a little hamburger and fry place just off Main Street will get the screw of his life.
Go figure, but from my point, that's why you guys keep asking us girls out. You like the feeling of the chase, of sitting there wondering if we will or if we won't while you shell out and fall all over yourself putting your best foot forward. I'll tell you though, just be yourself – honesty is a wonderful attribute and will win me over quicker than a $500 trip to the race courses opening meet – which is where I spent the first Friday in April.
the race course is the horse racing world's Mecca. It is THE place to be on the first Friday in April. And being there can cost no more than the $12 to park and another $20 for a couple of beers and a dog on a bun. Or, it can cost some bucks. I've had race course dates drop $1,000, all without knowing if they were going to get into my pants or not.
Actually, I should say without knowing if they were going to get under my skirt or dress hem because grown up big girls don't wear pants to the races. No, it's a skirt and heels, bare legs to the sun type of place. On this trip it was pushing 80 which means spaghetti straps, strapless bras and a dab of sun screen rubbed in well before arriving at the gate. The worst sun burn of my life came at the races, sex that night was awful. Thank goodness I left before sunup because I felt like absolute shit the next morning and screamed like a belt-slapped bitch when the shower hit the back of my shoulders the next morning!
And the first Friday in April 2010 was a beautiful day. A day meant to be enjoyed by kings and their queens. As well as by the minions of those among the commoners who found their way to the races for the sport of kings on that day.
I went with a girl friend and her daughter and the date of the girl friend. The daughter is one of my young mentors. At 21, she can wear a lot of my clothes but won't for long if she keeps eating and avoids the gym. She got her father's genes and his family leans towards heavy where her mother is one of those damn women who never exercises and looks great. Me, it's the gym, the bicycle, the rowing machine and any other torture device known to man to keep a hard, flat stomach and long legs. Shit, folks, let's face it, when you wear an A-cup bra, you can't afford a roll in the middle above the belt line!
But the daughter came to my house the night before our trip and she was dressed properly. She had brought a black bra and panties for the big outing. I put those beneath a pale yellow sun dress which her mother would never approve but hey, my house, my rules. A pair of three inch heels that she loves to borrow and her hair up in a tight twisted french braid hanging down to her bra strap with a touch of lipstick and make up to add flavor. She's a pretty young woman, not the little timid virgin her mother believes but not an out right slut. So I dressed her to draw a little attention, just not a lot of it and besides, with me as a chaperone, trust me, the looks could be turned on, or off.
As for myself, I dragged out a dress I only wear when I don't anticipate finding a lot of people from our little home town. It shows a tremendous amount of leg, in fact, it will show the bottom hem of a pair of bikini panties if I am not careful – or on purpose if I wish. The dress was a pale blue and I wore midnight black underwear and a strapless bra under it. I could have gone without the bra, but not with my friend and her boy friend along. Hopelessly high heels pushed me towards 5'10'' or so and enough lipstick to qualify me as a made up girl and we were off. That dress is cut low, but the only sight one gets is my bra, unless you happen to catch me leaning forward and sitting down. You might, might mind you, see a slope of a pale breast or the leading edge of my nipple. But it's a big might and you better work the angles really, really well guys.
The ride up to Lexington was fun, the younger girl and I had the backseats of a Chevrolet full-size pick-up truck. Even the rear-ward opening doors didn't keep us from putting on a show. Myself, well I yanked that hem up, showed a flash of panty and climbed aboard and then laughed as my young backseat cohort tried to get in.
Finally, I suggested that she either show her mom's date what she was wearing beneath the dress or he could turn his head, take their pick, but I was ready to go. The man turned away and the young girl hopped in. Her mother had no problem getting into the front seat – pants are that way. Darn pants anyway, as I hate them, but wear them a lot. It's a business world you know? And, well, if you aren't using the tools it's best to cover them up to keep the male minds somewhere close to the business at hand.
We had a great lunch and the younger lady did things for my own dress I can only dream about. I mean, I looked at her with a bit more hunger than I should, considering my mentoring role. But she really filled that dress out. A dress that is cut for an A girl worn by a baby B with a push-up bra. Well, you guys and girls can figure it out. Darn, she looked, well, great. I've heard that look described as “table grade”. I have heard it described in a lot of other ways, as well!
Getting in and parked was a snap with my friend's VIP parking pass. That's one of the things that deters me from the track a lot. Parking is rarely simply, today is was so easy as to make me wish for the good life. With no coolers or purses on wheels, we breezed through the entry gate and made our way to a nice boxed seat area. Not exactly the home of high rollers, but a far cry from the cheap seats. Looking down and out, we could see the occupants of those seats. The view from above looking down on a bunch of those low cut dresses was, well, stunning.
And the little slice of Kentucky we could see was equally pretty. All green with touches of early spring flowers popping up in groups around the grounds.
The stands filled and the first two races left my young charge with a few dollars to blow so I went with her down to the $2 window. As we stood in line, I noticed a man in a beautiful brown suit with a wonderful fedora hat watching us. I looked away, then back. Then I blushed. Yep, I actually blushed because a woman standing in the $2 line with a 20-year-old charge has no business casting eyes on a man in the $50 betting line. That would have been my entire stake for the day, $50 bucks. And he was fixing to blow it on one race. Hopefully, he knows more about horses than I do.
We both made our wagers and returned in time for the start of the third race, I lost again and yet another ticket found its way to the pitted concrete pavement beneath my heels. I could feel the wind tugging at my hat by this point and I secured it with a chin strap. Don't ask me to explain, guys, but I also know that a chin strap can be positioned behind the ears – aren't ears the handiest thing you've ever seen? Make good ankle rests, or so I'm told!
After the fifth race I excused myself from the group and went to the bar. Although my young friend could go legally, I don't teach that little experience in life. Somethings, a woman growing up just has to learn on her own. Oh, rescue her if she plays the game and loses, you bet. But this chick wasn't drinking on my watch. Her mother and date weren't either, so that meant Paula got a drink at the bar. Alone.
Well, I thought alone. As the barkeep pushed the glass towards me and said $5, the man in the suit and hat slipped in just in time to make an offer no lady refuses. “May I,” was all he said, with a smile and the simple passing of a $10 to the bartender. The man with the mop brow started to make change, but the hat man simply smiled and waved him off.
“Do you mind if I join you, lady?” he asked. A nod and he took the stool adjacent to mine. Now, the dress I had on wasn't meant for clubbing, not exactly at any rate. There was a slit up each leg that stopped about five or six inches below my hip bone. Had I worn anything other than high-cut bikini panties, they would have shown. As it was, I had an inch of wiggle room and midnight blue would be peeping out around the edges.
We talked for a few moments and the sixth race kicked off on the screen over the bar. I was swallowing a sip of alcohol when I felt the man's hand on my bare thigh. He had not the least hesitation as he rolled his finger tips to the inside of my thigh and then upwards to where the dress slit stopped his advance. Right there, with me and a glass in my hand, he pinched the absolute shit out of me. I found the bruise the next day. Right then, I just did good to swallow without choking and keep my pissed off attitude from showing.
“I was wondering from my seat if you were actually wearing underwear,” the man said, the question in this tone. “Now that you lost that extra inch of hem, I can tell that you.”
I looked down and realized that his pinch had caused a jerk on my part. The jerk had ripped the slit of the dress on up till the spaghetti thin strap of panty crossing my hip bone was clearly visible.
The man stood, smiled again and excused himself from my company. But in leaving, he motioned to the bartender, laid another $10 on the bar and told the man I would need another drink. I looked down and realized I had slopped half my drink across the bar.
Shit, damn, I hate it when I make an ass of myself. I honestly hate it.
I watched the remainder of the races through the ninth from my chair in the box. Laughing, talking with my friends and all the time stealing glances at hat man in the box across the isle. Tearing a page from the program, I found a pen in my friend's purse and wrote a simple note.
My cell number, along with the words, “I need a ride.”
Leaving the box, I eased across the isle, grabbed the hand rail on his side and, as he turned, I casually passed my hand over his suit jacket pocket. Please, God, let it be a real pocket and not a fake was all I could think. The note slid down into the cloth and I smiled as I went on up the steps.
The 12 th race came, and went and we exited the grandstands and were idling along the sidewalk talking about dinner plans. On a gamble and in a slightly loud voice, I made the comment that I really wanted to go straight on home. My friend's date obviously had plans, he was not going to waste an evening out with his lover and her daughter. There are major points to be gained there, guys.
Suddenly from nowhere, a voice broke into our conversation, “You asked about a ride, lady? I have a car and driver, perhaps I could drop you somewhere?” It was hat man, just off my shoulder and slightly to the rear. Little did he realize that I needed a ride 90 miles south.
“I do, but I don't know that you would want to go to London tonight,” I responded, trying not to let the desire drip off my voice. I'm sure my friend caught it, but only a grown woman would as the comment went right over her daughter's head.
“ Not a problem,” he said. “ I have no use for my driver after he drops me and London is just south of his home in Richmond,” responded the hat man.
I made my excuses to my girl friend, thanked her date for the wonderful afternoon and accepted the man's offered arm as we parted company.
“I really do live in London,” I told him.
“And I truthfully couldn't care less,” said the man. “By the way, how's your thigh where I pinched you?”
I said nothing but his grip on my arm tightened slightly and his voice dropped to a more husky tone but not a bit in volume. As we walked past a group of women walking alone, he turned to me and said, “Have you ever fucked in a limo?”
I blushed, and asked if I was going to. He responded that only if I was willing. And able.
His car was waiting in the corner where drivers wait for the boss. It was a long, four-door stretch Hummer2 with super high tires and a mud rail on the side.
The driver opened the door and then put his knee out with his hands to guide my foot onto the safe surface. As I stepped up, and then turned to enter the vehicle, I gave the world a show of my panty crotch.
The man stepped up and in effortlessly, obviously accustomed to the high step of the Hummer.. “For tonight, you may call me Keith. That is not my name, nor is this my car although the driver is my man to put it simply. Do you want to get out, or go to London?”
I looked at him, then at the driver's face waiting below the open door. “I'll go to London, Keith,” I said.
With that, the driver slammed the door shut and Keith stepped into a sunken well between the seats. With ease he removed his suit jacket, shirt and tie tack, then slipped out of his shoes and pants. He was not wearing underwear and, as his trousers came below his knees, I saw a hard cock of at least 7 inches, but unbelievably thick.
Keith smiled at me, laid his clothes aside and said, “Now, are you sure you want to go to London in this vehicle, if the answer is yes, you're going to take me however I choose,”
I wet my lips, my eyes locked on his cock. “Yes, but, I don't know ...” my response trailed off.
The man took my hand and drew it to his semi-hard penis. “You will take me everywhere, are you a virgin anywhere?” he asked.
“No.” The one word answer was out before I could stop it.
With that, he reached up and slipped my straps from my shoulders as the car moved out. I lifted my hips and allowed the material to puddle beneath my ass before he yanked the dress down and over my heels.
“Flat chested, I might have know,” he intoned as he gave the strapless bra a gentle yank, then a much harder pull which popped the catch behind me. He reached down and caught the waist of my panties between his fingers at each hip and they left my body as well.
By now we were moving through the outskirts of Lexington, KY, stopping at lights and surging ahead to make turns. Keith reached over and dropped the windows on all four doors beside us. Then, taking my legs he pulled them forward and up above his shoulders. His cock bobbed at the entrance to my cunt.
Even though I was wet, and had been for ages, it took a half-dozen lunges before he buried his girth in my pussy. It was so damned thick, it hurt. He saw the look on my face but did not stop lunging into me.
Looking down, I could see the angry red lips of my pussy surging around his cock and, to my surprise, noticed the condom he had managed to put on without my knowledge.
The man was a demon, at a stop light, he plowed me so hard that I grunted, then screamed as his last unbelievably thick inch was stuffed inside me abused pussy.
He finally backed off and allowed his cock to slip out, I noticed the accumulation of semen captured in the tip of the condom. Reaching down, I unrolled the rubber from his cock, fighting to get it off over the head of his still hard member.
As we merged onto the interstate, Keith climbed into the seat and pushed his cock head at my lips. I opened and within seconds was swallowing his length. But my mouth had never been stretched to this point before. I know he felt the scrape of my teeth several times in the five minutes that he throat fucked me. I also realized that people in the other lanes could see what was happening.
Finally, with his cock at an even bigger state of erection, he pulled himself out and pushed my face towards the car window. I gripped the door edge as I felt him fumble in the console in front of us. Looking back, I watched as he rolled another condom down his horribly thick dick and realized he he intended.
Keith spit into his hands, then parted my cheeks and pushed a single finger into my rectum. Without any lube, the finger felt like a normal man's cock. He extracted that digit and positioned the head of his cock at my little anal rosebud.
The drive lunged the vehicle over into the passing lane at that point and, without any warning, the first two inches of dick plunged into my asshole. I screamed. Then I screamed again, the sound carried away instantly by the slip stream of wind rushing past the car.
It was then that I looked up and saw my friend, her dinner date and daughter going by our vehicle on the inside lane. I smiled, caught her eye and waved. With the wind whipping my hair, the unfamiliar vehicle and all, I can only pray she only saw what she thought she saw, not was was there, displayed in front of God and everyone.
I was laying on the window sill at that point, my small breasts not even large enough to dangle in that classic doggie position. A man's cock was trying to penetrate the depth of my ass. And it simply wasn't going any farther.
Looking back, with tears running down my face, I begged him to pull out. He did and I reached down and stripped the condom off his cock. “Now, in my pussy, please, get it wet before you fuck my ass,” was all I could think to say.
Keith plunged that incredibly thick sausage back into my soaked, but thankfully well-stretched cunt. He plowed me for another five minutes before pulling out. This time, I reached back and parted my own cheeks, my face buried in the driver's headrest.
I let out a single scream as the huge, thick penis slid all the way home in my rectum.
For 10 minutes that man fucked my ass. He reached up and grappled my tits for only a moment before yanking his hands back to my hips, calling me a “flat bitch” as he continued to butt fuck me.
I don't know how long that motion went on. But we were passing Mt. Vernon, KY when he finally fell back into the seat behind him and gave me the order to screw him myself.
I lifted and plunged, my own hands milking and twisting my small breasts as I tried to get him off. Several minutes later, he pulled me down and held me at the base of his dick and I felt the hot, sticky crawl of his cum draining into my bowels.
Keith held me that way for another 10 miles before finally pushing me forward onto my own seat. I found my panties, slipped them back on, then the ripped dress. As I dressed, I felt his semen leaking from my ravaged ass hole.
I leaned forward, took his cock in my hands and kissed my one-time lover deeply on the mouth. “Thank you,” was all I said.
There were no more words as we pulled into the first restaurant at the very first London exit. I left without help, the man sitting there and staring at me. As I started to close the door, he took a slip of paper, the one I had written my note on, and handed it to me.
I was inside and they were gone before I looked at the other side of the paper. Below my note, he had written, “I knew you would be great, call me, sometime,” and a phone number. I punched the number into my cell phone before I called a friend for a ride.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/anal/a-day-at-the-races.aspx">A day at the races</a>