#223) A Piece for Kentucky Derby Day

I was taught to ride horseback by my grandpa when I was small; it instilled in me a life-long love of all things equestrian. I still ride occasionally to clear my head, both English dressage and Western for pleasure trails. I like to go to the rodeo when it’s in town. And I ALWAYS follow the Kentucky Derby, from all the prep races leading up to the big day through the entire Triple Crown for the next five weeks.
I’ve been to the Derby at Churchill Downs once. It’s true, until you’ve seen the Derby, you ain’t seen nothing. I LOVE the fashion, especially the hats on the ladies. Let’s fashion a little story together…
Let’s make the story take place on the Friday before the Derby, the day the Oaks is run, a race just for the fillies. This’ll be about fillies, equine and human. I see her on the balcony in front of Millionaire’s Row. Like the horses on the track, this well-bred thoroughbred exudes class. She doesn’t go in for gaudy; she’s dressed in basic black, from her designer dress to her high heels to that broad-brimmed hat. Her make-up is flawless, as is her olive skin. Because of the latter, she doesn’t need much of the former, just a little mascara and a lot of lipstick on those full sensuous lips. The only other splashes of color are her blue jeweled earrings and that yellow and blue nail polish. Is that I tribute to the Ukraine flag? We may have similar sensibilities…
I come up behind her, lean in under her hat to whisper in her ear.
“I’m so disappointed to see your wedding ring, I’m falling in lust with you!”
She gives me the side eye, apparently likes what she sees. She smiles.
“I only wear that to keep the pesky men from buzzing around me. I call it my ‘flyswatter’. I’m not married. I’m not straight.”
“I’m neither either,” I return, “but are you kinky, like me?”
She smiles even wider, “I knew there was something about you that I liked!” She offers the hand without the jewelry. “I’m Karen.” I shake hands with her, am hesitant to release it, so turn it in my hand.
“I’m Jeanie. Is your nail polish referencing Ukraine?”
“Yes, very insightful.”
“I care,” I lament, “but feel so powerless. It’s so far removed from all this…” and I gesture at the opulent surroundings.
“I know… frustrating…” And we feel like kindred souls. Then Karen brightens, “Do you know what you’re doing here? I’m losing badly…”
“I like the number one horse, Secret Oath, in this upcoming race, the Oaks. I like the way she’s trained up to this, with that bullet work. She’s on her toes and full of herself in the post parade, confident. And she’s got a hot jock on her back, and a legendary trainer.” No sooner were the words out of my mouth than I had a vision of putting confident Karen on her toes by riding her hard, using a riding crop on her haunches…
Karen followed my advice and bet on the number one horse and won big. She sat at my table inside the historic pavilion and we continued talking, both about horses and handicapping, and other topics. We discovered that we were both staying at the Galt House, the old world premiere hotel in Louisville, kind of like the Pierre in New York City. After the rest of the day of races and winning, we rendezvoused back at the hotel’s bar. We drank cosmopolitans.
“The only thing left to determine is whether you are a Top, a bottom, or a switch,” I said, looking Karen in her deep pools of brown eyes.
“I’m a switch with the right person. And you, Jeanie, strike me as just the right person.”
If the alcohol made me light headed, her demeanor made me elated. “Your room or mine?” I asked, unable to stop smiling.
“I’ve seen my room, let’s see yours,” Karen answered, took my hand, and we strolled to the elevator. Once its thick doors slid closed, we attacked each other, kissing passionately, knocking out hats off our heads. “These hats are a pain!” she complained.
“But you look so sexy wearing it! Promise me that you’ll keep it on during our tryst… please! And our high heels, too…”
Inside my hotel room, we took each other’s clothes off. I felt my pussy become sodden when I saw Karen in her matching black lace bra and panties, then I peeled these off her, too. There she stood, in just that big hat and those high heels, with so much delicious femininity between those two extremities. And I stood in just my chapeau and shoes, unable to keep from panting in excitement. Karen took the lead.
“I’m used to Topping. I want to submit to you first. Spank me as red as your fingernail polish, no darker, as red as my lipstick!” she said crawling across my lap on the bed. “…And I’m Topping right away! Spank me for that, too!”
I did. I spanked her beautiful big bottom long and hard. I made her kick her long legs, in order to absorb the pain in her ass, until her shoes went flying off in different directions. I spanked her olive-complected butt until it glowed, until it radiated, until I nearly climaxed involuntarily. I dug my fingers into her firm cheeks and parted them wide. God, even her ass hole is gorgeous, I thought to myself as I gazed at the hairless, tiny, tight orifice.
“May I touch you here…play?” I asked, touching her there.
“You sound as anal-erotic as I am,” Karen answered. I took that as a yes. I spit on it and on my fingertip and plunged it in. No sooner did I get in knuckle deep than I began to spank her again, alternating orbs as my finger thrust in and out of her tooter. Karen started to moan, a vocalization that came from deep inside her. I’ve never heard such a profound, guttural, hungry growl come from a woman. It didn’t seem to come from her throat, or from her lungs; it came from deep within her. We were off to the races. Karen started cumming as I masturbated her butt and spanked her mercilessly. She stiffened, then collapsed across my lap. I kissed the ass I’d just belabored until Karen revived.
“Do me!” I gasped, and we switched places. Karen was a regal, natural born Dominant. She spanked me expertly, until I couldn’t fight it back any longer and came in a gush across her thighs. She let that be the signal that we should move on from playful punishment to pure pleasure. Tongues and fingers in vaginas took over where palms (and one finger) had lit the flames to stoke our fires into a conflagration. I made her cum again, harder, then she worked on me. Just as I reached my peak, Karen raked her pale yellow and light blue long fingernails across my tender tushy’s flesh and down my thighs. I groaned and came in her mouth.
On the racetrack, they call it a dead-heat when two thoroughbred horses finish the race at the wire simultaneously. My orgasm was so intense, I suffered the little death, what the French first labeled as petit morte. I fainted dead away. When I came to, Karen was leaning over me. Her lipstick was gone. My pussy juice replaced it all over her mouth. She was sweating, flushed and red-faced.
“I’m dead and you’re in heat,” I joked wanly. Karen didn’t get it.
Karen lived in the deep South, I on the East coast. We put our phone numbers into each other’s phones, but both of us secretly doubted that we’d ever get together again. She had an early morning flight back home, said that it’d be easier to part now. It was just racing luck that had brought up to this blissful, wistful moment. Karen got dressed. I tried to stifle, then hide my tears. I kissed her with all the passion in my heart, tasting my jism on and in her mouth. As soon as I closed my door, the tears burst forth, and I ran back to the bed, sniffed it until I found where Karen had left her scent, and snuggled there in a fetal ball, euphoric that I’d just shared myself so intimately, empty at the same time.

3 responses to “#223) A Piece for Kentucky Derby Day”

  1. The racetrack is a spanko’s kind of place. The far side of the track is called the backside. A horse who closes on the front-runners is said to come from behind. They carry whips and use them!They don’t allow artificial insemination to make a thoroughbred, so the horses have a choreographed sex date, and they call the mare’s owner a breeder. The daddy is called a stud. Mount up!


  2. “…I felt my pussy become sodden.”

    “Sodden.” “Moist,” “wet,” “damp,” sure. But this is the first I have heard sodden. Like a log submerged in a river for a long time.


    • Like you could press the heel of your hand against my pubic bush, and it’s be like you were wringing out a washcloth. I was awash with desire. I was floating away on it. I was drowning in it. Sodden. That’s what I wrote and that’s what I meant, damn it!
      Just kidding! Felt like ranting what with men questioning my word choices, wanting to punish my poor butt when they were in the wrong…
      I’m better now, A.J.
      Jean Marie


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