Miss Entucy Derby

I had a chance to go to the Kentucky Derby in 1979 with my college girlfriend, Jessica, but I didn't. I regretted not going to America's biggest equine event, but things turned out pretty good, after all.

Jessica's best friend and roommate, Cindy, would be driving her new car there and invited me to go along. She was dating my roommate, Steve, and so the four of us would be traveling together. Make that five. You see, Cindy had a beagle named Brownie that accompanied her everywhere she went. After weeks of looking forward to attending my first Derby, the very night before we were to leave, she informed me that, since her little Pontiac Sunbird seated just four—a tight four—I would have to hold Brownie in my lap.

Now, Brownie was a really nice dog, but it was just the principle of the thing that I could go only if I held him that made me decline. Steve was her boyfriend, and why couldn't HE hold Brownie? What about Jessica, her best friend? Cindy was, basically, a bitch, and though pretty cute, never was there more of a mis-match that she and Steve. He was a great guy with a super personality, the most friendly, genuine dude I ever knew. Further, he was great looking, with a chiseled face, wide white smile, and long, sandy blonde hair. He played cornerback for our Southeastern Conference university, having the wide shoulders and slim waist of the classic football player build. Resembling David Lee Roth in his heyday, Steve was, in a word, a hunk that girls swooned over. Dude could walk into a bar and leave with any girl he wanted. Never did figure out why he was dating Cindy. He could do better, much better.

They left on a Friday afternoon while I stayed behind. Cindy's older brother was a big-time large-animal vet and was there to look after some famous horse in the race. So, with his status and connections, he got them all VIP treatment, invites into the track infield, hoity-toity parties, the whole nine yards.

Knowing this ahead of time, I lent Steve--who didn't have any dressy clothes--a crisp button-down-collar shirt, blue blazer, pressed cotton khakis, and some nice loafers. None of them was a perfect fit, but he looked spiffy. Frankly, Steve could throw on a pair of ragged cut-offs and be the best-dressed guy in town, but he needed appropriate attire for these special events.

Anyway, looking forward to Jessica's return, when there was a knock on my door late Sunday afternoon, I snatched it open to find her already pulling the sundress off over her head. Never wearing bra or panties, she was instantly naked. The puffy nipples on her pretty little apricots looked like they really needed to be sucked. And, at the terminus of her long legs, I could see through her scant bush glistening pussy lips and clit that beckoned for a good licking and dicking. But those activities would have to wait, for, sporting a naughty grin, Jessica poked me back a few feet, kicked the door shut, and lay a hungry and wet French-kiss on me. Sliding her tits down my chest and stomach, she dropped to her knees and gulped down my cock. Jessica absolutely loved to give blow-jobs and was one of the best at it in the history of womankind.

Naturally, after having been apart for two solid days, we had to make up for our then-typical fuck-three-times-a-day routine, and so got right down to business for the next couple of hours. I was lying there on my bed recharging when it occurred to me that Steve had not come in with her. Where was he?

Jessica said I was not going to believe what happened and recounted the story:

Steve and Cindy got into a spat on the drive up. I suppose without me there for Cindy to direct her near-constant barrage of snide remarks at, Steve got in the line of fire. Add in beer and the close quarters of her Sunbird, and you have the formula for an argument.

As soon as they got to Louisville, they rendezvoused with Cindy's brother at Churchill Downs and, with the well-connected vet leading the way, headed to a big pre-race party of crem de la crems where every man was wearing a tie but Steve. It was there that Cindy was openly criticizing him for being underdressed (I'd offered him one of my ties, but he just couldn't go that far and refused) and was ragging on him for imperfect manners. This was a crowd of upper-crust socialites, and, in truth, Steve was out of his operating range. He was such an affable, down-to-earth guy, and I'm sure he offended no one; yet he was anything but refined, and Cindy was treating him like an embarrassment.

Jessica said he was understandably pissed and lost Cindy and her in the crowd. At one point, they saw him across the room chatting up this gorgeous chick who was partying hardy. Much later, when Cindy and Jessica were ready to leave and asking the few left as to his whereabouts, they could get no one to say anything but an overly polite "I have no idea," though it would be an understatement that Steve stuck out in that crowd. Finally, they found a thoroughly inebriated old gentleman who was sufficiently sloshed to spill the beans. He'd been outside smoking a cigar and saw Steve and the gorgeous party-girl zoom off in her Bimmer. Apparently, it was lust at first sight, for that was the last anyone saw of Steve that weekend. Oh, who was the girl? Miss Kentucky Derby!

Yes, Steve hooked up with no less than Miss Kentucky Derby. Maybe it was the clothes I lent him. Probably not. Talk about sweet revenge: The bitch Cindy publicly puts him down, and he fucks the beauty queen! I watched the Derby on TV and saw her on camera. She was truly beautiful.

Furious, Cindy made no further effort to locate Steve and left with Jessica and Brownie on Sunday without him. Now the dog had the whole back seat to himself!

Anyway, Jessica told me about all the fun they had for rest of the festivities and the well-heeled equine gentry they met. Interestingly, the race itself seemed to fade into the background of before and after parties. We fucked one last time, and she departed in the early evening for her apartment to study for a test. I puttered about, made dinner and showered while trying to get a better bead on exactly what Miss Kentucky Derby looked like. I recalled that she was extraordinarily attractive, but—not knowing my own roomie was boinking her—didn't save a real clear mental image. I wondered if I would see Steve--and my clothes--ever again.

Then about 9:00 o'clock, while I was quietly taking a dump in the john down the hall, I heard him boisterously come in, accompanied by a voice and giggles that were distinctly female. Could that be Miss Kentucky Derby?

Our apartment was a large one bedroom, and when we'd flipped for the bedroom, I lost. Consequently, my "bedroom" was not partitioned from the rest of the very spacious den/dining area. It actually worked out OK, since I had most of the furniture and the stereo, and Steve got most of the pussy. In fact, my double bed was right by the door. So, I ambled down the dark hall to see that he and some slender chick, both naked, were in my big bed and all over each other.

I hoped they appreciated that Jessica, the cum-lover, had swallowed every drop of my semen earlier, leaving the still-unmade bed clean. To respect their privacy and let them know I was home, I ducked into the kitchen and intentionally rattled stuff around, thinking they'd take their sex party on down the hall to his bedroom, which had an actual door. I could see as they walked past the kitchen/hall doorway whether or not she was Miss Kentucky Derby and satisfy my curiosity

But they stayed put, and from the sound of things, they were getting hot and heavy. Before I'd gone to the bathroom, I'd just cracked the last cold Bud, and it, along with the bong and weed I'd just cleaned, was sitting on the dining table, in direct view of my bed.

I'd already eaten and washed the dishes, so what was I supposed to do, stand in the kitchen all night or skulk back down the hall into the tiny bathroom?

"You suck dick so fuggin' fine!" I heard Steve say, over the sounds of her slurping.

"Just keeping licking. Oooooh, that's it, perfect. You eat pussy soooooo good!" the female voice called out.

OK, it doesn't take a genius to figure out they're in a 69. Despite that major sex session I'd had with Jessica earlier, I was getting turned on. And, of course, I was just dying to find out if this gal was Miss Kentucky Derby. Whoever she was, she was naked having sex with my roomie in my bed not 20 feet away. Should I take a peek? All I had to do was tip-toe through the other doorway—the one leading from the kitchen to the den-dining/my bedroom space, peer around the corner, and there they'd be in my bed.

No, I would not peek. That would suggest I was doing something wrong. THEY were the ones doing something "wrong"—fucking in my bed—knew I was home, and, besides, my beer and reefer were awaiting me out there.

So, I just sauntered on in to the dining area, sat down, took a sip, and loaded up a bong hit. As I turned around to situate the tall bong between my knees and do up the hit, my eyes gazed up to see her perfect buns framing a pair of wet pussy lips, below which Steve was rapidly flicking his tongue on her engorged nubbin.

He disengaged momentarily and looked back at me, upside down, making his face appear to be frowning. But, of course, he had the biggest smile ever, though his furrowed brows telegraphed "What the fuck are you doing here?"

"Bong hit, anyone?" I casually offered.

"Yeah, I'd like a one," she said, raising up and twisting around to give me a side-view of a particularly pretty peach. "Would you pour up some mint juleps? Bottle's in my bag there, already mixed up. All we need is ice and glasses. We've been living on 'em all weekend. Help yourself."

I recognized that beautiful face. She was Miss Kentucky Derby, all right, but she looked different—even better. I think it had something to do with her having a super hot body and being nude. Yes, that was probably it! Moreover, she didn't mind one whit my watching them go at it. All I had to do was mix drinks and furnish bongs. A fair deal, I thought.

When I came back from the kitchen with the drinks, she had impaled herself on Steve and was riding him cowboy, er, cowgirl, horsegirl, whatever, you know, on top with a cock in her pussy.

Facing me, she was as relaxed as a woman sitting fully clothed on a Chippendale chair, taking a big gulp of the mint julep before carefully setting it on the bed and inhaling a humungous hit from the 2-foot bong with nary a cough and then leaning down to lock lips with Steve and blow it shotgun-style into his lungs.

So I sat there watching her boobs bobble and Steve fondle and tweak their hard little nipples as she methodically up-and-downed her hips on his prodigious, picture-perfect penis, pausing every once in a while to grind her pussy around or French-kiss him before resuming proper all-the-way-in, all-the-way-out shaft work. I could tell that Steve was somewhat anxious, but, of course, not enough to stop and go elsewhere!

Meanwhile, I sat at the table not 10 feet away loading us bong after bong, sipping my mint julep. Thrusting slowly up and down, she informed me that she'd made the mixture herself according to an old family recipe with real mint leaves and some rare, practically ancient single barrel Old Grand Dad bourbon whiskey. It was extraordinarily smooth, smoky, and superb. Best whiskey I ever drank.

Despite being quite obviously a Kentucky blue-blood accustomed to the finest things in life, she had absolutely no qualms about screwing in plain view, all the while nonchalantly conversing with me about whiskey, the Derby, and so forth.

She gradually picked up speed and came with a shuddering orgasm, pussy juice streaming around her well-manicured brown pubic hairs (swimsuit competition) and down her lovely inner thighs. She had that definite pageant look—almost too perfect—if there is such a thing, and it was quite obvious what her REAL talent was.

Steve twisted her around so that she was facing away from me, then slid his legs from beneath her, and at once pulled her hips up as he stood on the floor at the edge of my bed to shag her doggie. In so doing, demonstrating talent of his own, he never allowed his cock to slip out of her cunt. Impressive. More impressive was the appearance of her tight, sopping-wet pussy, its lips folding out of sight on his in-stroke and back into view on the out-stroke, over and over and over again.

I refreshed their drinks and quickly returned with them and a hit for Steve, holding the tall bong up and lighting it for him as he peeled her buns back to give me a close-up view of both delicious holes before exhaling and wiggling a pussy-juice-lubed thumb into her welcoming pooper. Her medium-sized boobs were hanging alluringly down, swaying to and fro with each thrust of his cock. Flinging her long, lovely brown hair over her neck, she turned and looked into my eyes, giving me what can only be described as a pageant-winning smile. I imagined her in the Miss America contest giving her answer to "the question," sincerely saying she wished for world peace, or perhaps a worldly piece of cock. Ha!

Speaking of cock, mine had bored its way out the wide leg of my Dolphin shorts and was sticking straight out, hard as a bat. Don't ask why I didn't just feed it into her mouth right then and there. Some kind of Southern gentleman complex, I suppose.

Anyway, Steve quietly pounded her ever harder and faster as she oooohed and aaaahed and cussed like a sailor. Finally, his hips a blur, he crammed his other big thumb in her tiny brown hole to pair with the other still there and blasted volley after volley of man-juice into her quivering cunt. She, too, came tumultuously, belting out an eardrum-splitting scream that could surely be heard eight floors down on the ground floor of our high rise.

Gradually decelerating to a slow fuck, he pulled out to reveal her gaping-wide-open vagina oozing a veritable river of white cum. Plucking his thumbs from her anus, it remained relaxed and open, as if to ask, "Why don't you poke your dick in here?" but, alas, it didn't happen. They then gathered their clothes and things and headed down the dark hall, stopping off in the bathroom before going into his bedroom, closing the door behind them. The show was over, but, before long, they were at it again. Lying in my bed, I used up half a bottle of Jergens lotion and whacked off for hours while listening to their moans and groans, eventually letting myself cum and falling into a deep sleep.

I awoke the following morning to the sound of silence and rushed off to class just in time to make it. When I returned, Steve was sitting at the dining table chowing down on enough bacon and eggs and biscuits to feed a brigade. I'd never seen him look so exhausted, even when bruised and bloodied after football games. The man was beat. I sat down, cleaned some weed, and told him to tell me the whole story from beginning to end. Though he was a real ladies' man, even he kept shaking his head back and forth as he told the story, saying "unbelievable" time and again.

His story matched Jessica's, and he said from the moment he met the beauty, it was clear she had the hots for him and wanted to fuck. With that in mind, he grabbed his stuff out of Cindy's car—convenient, since the windows were left partially down for Brownie—and they left the socialite party and went back to Churchill Downs. Earlier, Cindy's brother, the horse veterinarian, had given him, Jessica, and Cindy VIP badges that entitled them to go anywhere on the grounds. So, off he and the hottie went back to the stables, where they got naked and literally took a roll in the hay amongst million-dollar three-year-old thoroughbreds.

At one point, she hopped up on one and began slathering her pussy back and forth along its back. Kinky as shit! Not to mention dangerous! I'd love to know what horse that was and what effect her antics had on its race performance. Anyway, they sucked and fucked and licked all night long in various stables, eventually curling up to fall asleep in a vacant one, only to awake the next day to resume the fuck-fest. Without watches, they didn't know what time it was, but she figured out it was way later than she thought and told him she had to scram in order to get ready and dressed for an "official appearance." It was only then that he found out that she was, in fact, Miss Kentucky Derby!!!

So, when I saw her on TV, she had been romping not long before in the stables with none other that my own roommate, Steve. Like he kept saying, unbelievable!

They hooked up right after the big race and went to several invitation-only parties where he met the governor of Kentucky and many other dignitaries. Thankfully, he had the right clothes, which, by the way, he'd totally ruined by the time he got back home. During the parties, they sneaked off to fuck time and again in the bedrooms of the magnificent homes. I suppose it was the frequent taking my clothes off and putting them back on that just wore them out!

They checked in some upscale Louisville hotel sometime early Sunday morning, crashed, and had a swanky room service brunch when they awoke. She, of course, paid for everything. He'd never had caviar before and thought it might be gross, but quickly changed his mind when she dabbed some onto her nipples and asked him to suck it off, finding the fish eggs really quite tasty, after all. He said the chocolate-covered strawberries he ate from her pussy were the best he ever had.

They stayed at the hotel the rest of the day, drinking champagne and, of course, having sex, before ordering a staggeringly expensive room service dinner consisting of filet mignon and lobster claws. He did not say from which of her bodily contours and orifi he consumed those treats.

It was not exactly a case of wham, bam, thank-you, sir, either, as she drove Steve ALL the way back to our college town, several hundred miles away, drinking mint juleps and tooling at break-neck speed in her BMW 2002. Of course, she had more sex with him when the arrived at our apartment, as previously described.

He said she really liked his thumbs in her bottom, and after they went back into his bedroom, she literally begged him to eat out her ass and then butt-fuck her. Always cooperative, Steve honored her request while she used a basting syringe she found in the kitchen to frig her pussy. I found that hilarious, as the baster was an implement my mother gave me before I left for college that I'd never used. I was simply delighted that someone had found a use for it. At any rate, this was the late 1970s, and it was extremely rare to find a girl back then who'd let you run it up her poop shoot, much less plead for it.

Steve said they stayed up until the wee hours of Monday morning until he was spent, or thought he was spent. She wanted to suck his dick some more before she left. He was amazed that she was able to get him hard again and coax out a couple drops of cum, which, like all good girls, she swallowed with glee. She departed prior to sunrise, before I awoke, and we assumed she drove back to the blue grass of her Kentucky home, never to see or hear from her again.

As I mentioned before, Steve was a guy who had the personality and looks to bed just about any woman he wanted and had fucked many. He said of all the women he'd been with, when you combined good looks, kink, horniness, and fun-to-be-with, Miss Kentucky Derby was the all-time best. Coming from Steve, that was some declaration. I'd guess you might say he enjoyed the way she "horsed around."

Needless to say, that was the end of his relationship with Cindy, who never spoke to Steve again. Of course, the irony was that, had she not been such a bitch and insisted that I hold her dog, then I would have gone along, and things would have turned out differently. Without me to bitch at, she sniped at Steve, pissing him off and driving him to fend for himself at the party alone, where he met Miss Kentucky Derby. By fucking her, Steve may have pulled off the sweetest revenge of all time.