The Hobbler 4: Maryland Riding Academy

0 items
The Hobbler 4: Maryland Riding Academy
The Hobbler 4: Maryland Riding Academy
Year: 2017
After hobbling Flash Jester in the Kentucky Derby, Sarah has a holiday at the Maryland Riding Academy hoping to find the self-control she needs to stop. But more opportunities for horse fucking just keep presenting themselves.
Sheela B.
  • Free Sample

Sarah Chambers climbs out of the manure hatch on the morning Kentucky Derby glancing around to see a couple of cars and a driver in each, the racing people hadn’t arrived to begin the morning work yet.  The hatches abutt the stables, behind them, and are there for manure to be collected after race day is over.  Today is the big race and after spending the night fucking the energy out of the favorite ‘Flash Jester.’  This is her job as the hobbler, using her mouth and cunt to drain a thoroughbred enough, so it will lose the race, an entirely untraceable form of race fixing.   She stands aside as Josh Norris climbs from the hatch and it’s closed and locked again.

“Job’s done,” Josh said to his father, Carl in a quiet voice.

Carl Norris, a tall, thin man with a craggy face, glances at Sarah with a smirk making her turn away, as her face burns.  “I knew I could count on you,” Norris said to the teen girl.

She turns back toward Norris with a frown on her face. “I don’t get it,” she said.  “According to the form guide, your horse isn’t even a chance to run a place in the Derby.”

Norris shrugs.  “True, Big Red won’t win today,” he said, “but a place isn’t impossible.”

“So why do this to Flash Jester, he does have a chance of winning?”

Josh laughs.  “He’s the favorite, so he’s pretty much unbackable,” he said.  “So we want to make sure the horse we’re betting on wins.”

“What horse is that?”

Norris said sarcastically, “What did the form guide tell you?”

She thinks for a moment.  “Um, I’d say the next-best horse is ‘Always Dreaming,’” she said.

Josh laughs and rolls his eyes.

“Get in the car, Josh,” Norris said sternly as he takes Sarah’s arm and leads her to the second car.  “This car will take you back to your motel.  Have a shower and get some sleep, you still have a big day today with your Olympian’s.”

As the old man opens the back door, she asks, “Am I right about ‘Always Dreaming’?”

“You know better than to ask,” Norris said coldly.

The man practically shoves her inside and shuts the door.  The car starts and drives away; the driver soon lowers a window because her smell is outrageous in the confined space of the vehicle.  The driver is visibly relieved when the fresh air rolls over him.


As she showers, the water is nearly black as it drains away, and she has to scrub herself to get clean.  Her body aches, especially her cunt as the big horse cock had fucked her hard and stretched her poor pussy beyond its limits.  When she douches, Sarah sees blood wash from her pussy, and it doesn’t surprise the woman.  No sex for me for a while, she thought.  My pussy will need to heal after Flash Jester’s huge cock.

Her mind is ticking over about Norris’s plan to hobble the favorite so they can make more on the eventual winner, which she thinks has to be Always Dreaming. After she’s in bed fighting her tiredness, she grabs her phone, opens the Bet365 app, and looks at the current odds.  The favorite by a long way is Flash Jester, the odds on him winning are currently three to one and Sarah knows that’ll shorten by the time the race starts.  Always Dreaming’s odds surprise her at fifteen to one.

She knows this horse by reputation, and going by the form guide, she really can’t see any other horse that can challenge Flash Jester today.  Though a couple of other horses are at shorter odds than Always Dreaming, her horse instincts can’t get away from what seems obvious.  Especially after what she did tonight, Flash Jester will not win today.

If he does, he’ll be the greatest racehorse I’ve ever known, she thought with a yawn.  Too bad, nobody will know what he overcame to achieve that.  The temptation to bet on the race is too great, and she transfers all her savings into her Bet365 account, ten thousand one hundred and twenty-five dollars. Sarah bets the whole amount on Always Dreaming for the win.  Not long after she falls asleep.


The sound of knocking wakes her and she gingerly climbs out of bed noting how her body is aching all over, especially her groin.

Coming—coming,” she shouts as she wraps a robe around her naked teen body.

When she opens the door, her boss John is standing there, and his eyes bulge with a loud gasp as the man sees her for the first time.  “Omigod, Sarah, you look dreadful,” he said breaking into a frown of concern.

She does appear roughed up.  Her blonde hair is all over the place, she’s pale with deep dark bags under her eyes, and her body is sagging as if in apparent discomfort.  Sarah decides to play along, remembering how she told him she had gastro as her excuse for missing the dinner last night.

“Yeah, rough night,” she said with a shrug.  “But I think I’m over the worst of it.  I’ll be at the track as planned.”

He steps inside, and she doesn’t close the door.  “Don’t be silly,” he said.  “Lucy will prepare Rambo, and then help Ryan with the other two.”

“I’ll be fine,” Sarah said. “Lucy has other things to do.”

“Nothing is more important to her than Rambo, you know that.”

Sarah does know the Equestrian’s love for her horse better than anyone does, as she remembers watching Lucy and Rambo in action at The Ponderosa.

“What should I do then?” she asks.

“Get some sleep,” John said.  “Come in later only if you’re sure you’re OK.”

If only you knew why I look like this, she thought feeling shame.  If you knew what I did last night to rob Flash Jester of his moment of glory, you wouldn’t be so kind to me.

“All right,” she said, and sighs, “I’m sorry to let you down.”

“Don’t be silly, Sarah,” John said, “It’s not your fault getting sick, it’s just unlucky.  Now keep your fluids up and if you’re not feeling any better by midday I want you to go see a doctor.”

“I’ll be OK,” she said.

“Call me if you need anything,” he said with a smile.  “Now I gotta go.”

“See ya later, at the track.”

He squeezes her arm and leaves.  Sarah closes the door and goes back to bed.


Sarah gasps as she sees Josh smile wickedly and raises his open palm to slap the snorting horse’s ass. She hears the loud crack, and then feels Flash Jester jerk forward. The horse’s huge, round cock head is stretching the walls of her cunt until she thought her pussy might rupture.

OOOARRRGHHH,” she groans as Flash Jester’s enormous, pulsing hunk of horsemeat rams all the way into her cunt with one firm stroke. Sarah’s body goes slack as her mind ignores the pain, mental and physical.  Her ass lifts into the air by the horse’s fat cock as it pumps steadily into her fantastically tight cunt.

Oh, wow, horse slut, you really are the best horse fucker in America,” Josh shouts and laughs coldly, watching her lower belly bulge with every forward thrust of the horse’s big cock.

Josh squeezes and milks her tits as the horse fucks her hard.  Throwing her head from side to side, as more cock penetrates her, she feels the head push against her cervix.  The thick cock, thicker than a man’s arm, stretches and pushes her cuntal walls in the way she’s grown to love, and moans escape her.  The stallion is suddenly pressing her against the hay bale, crashing into her with the meaty thwack of flesh-against-flesh, and driving her body into the bale.  She can feel the engorged head scraping through the length of her overstretched cunt, as waves of pain/pleasure ripple through the length of her body.

On, and on, he humps her without care or respite.  She gasps, her breath coming short in her lungs as her body twists and jerks on the huge cock.  Another orgasm rips through her like fire, and suddenly the stallion tenses, and buries his cock in her cunt as deep as she can take him.  Twenty-five inches of horse cock throbs in her body as he starts to ejaculate again.  She feels something similar to a fire hose burst in her, filling her with fiery, soothing liquid, thick and sticky.  Her rumbling cunt and raw clit respond, and she suddenly finds herself cumming.  Her cunt gobbles and sucks hungrily at the horsemeat, and she squeals.

Then she feels the giant cock in her throat, it’s hard to breathe, yet the thing moves in and out, slowly inching forward by the moment.  Josh is laughing loudly, slapping her tits and ass, as the dominant animal forces its cock out of her mouth from inside.  Flash Jester impales Sarah, with her pussy against Flash Jester’s balls, and its flanging cock head pressing against her nose and eyes. The stallion starts shooting cum all over her face, covering her, so all she tastes and smells is horse cock and semen.



Sarah sits up with a gasp and wide eyes, the dream had been so real.  Impaled on the giant horse cock from cunt to mouth bizarre and humiliating, impossible, yet exciting just the same.  The way Josh had laughed at her and called her names made her feel cold.  Glancing at her watch she see’s it’s nearly eleven am, so she drags herself from her bed, her body still aches, and has another shower hoping the hot water will soothe her muscles.  Later, she gets a taxi to the racetrack and eventually makes her way to the stables where her horses are.

The first stall has Rambo inside looking immaculate, Lucy’s experience and love for the horse showing.  However, no one else is there, so she goes to the next stall to find Ryan and Lucy finishing the chestnut mare ‘Lady Bianca’ as the other, a gelding called ‘Lionheart,’ is ready.

“WOW, you guys have done a great job,” Sarah said to announce her presence, “the horses look terrific.”

Ryan and Lucy turn to face her with raised eyebrows, smiling and happy to see the attractive blonde trainer.  “Oh, hey, Sarah,” Lucy said, “How are you feeling?”

Sarah shrugs.  “Like a truck just drove through me, but I’ll live,” she said.  At least I don’t have to pretend to be sick, she thought.

“I told you that fish burger looked bad,” Ryan said.

Sarah doesn’t remember him saying anything of the sort but goes along anyway.  “I shoulda listened,” she said, “it tasted good going down, for what it’s worth.”

“Not so good coming up, I bet,” Ryan said and chuckled.

“No,” she said and grimaces, “sorry for being a hassle.”

“It’s no hassle,” Lucy said.  “We’re all a team, right?”

Sarah nods.  “Mustn’t be long before you have to go enjoy the spotlight?” she said to Lucy.  “You look beautiful in your gear.  Rambo’s a lucky boy.”

The comment strikes Lucy as odd as if Sarah is talking about her man.  “Oh?”

Voices sound from behind Sarah, and she turns to see the other two riders and greets them, all sorry she had been sick.  Eventually, Sarah extricates herself from the stables since John had told her to take the day off anyway, and heads for the track to immerse herself in the atmosphere of race day at the Kentucky Derby.  She doesn’t go to The Ponderosa’s corporate box, nor does she go to the one Norris is using for his guests and family.  Instead, she pushes through the crowd to the fence so she can watch her Olympian’s moment of glory, then the Kentucky Derby.

She wonders if Flash Jester will recover in time, yet she knows it’s impossible.  I’ll lose ten grand if he does, but it’d be worth it to see Norris’s face, she thought.  A passing vendor sells her a bottle of cool water, and she drinks, waiting.  Eventually, the loudspeaker trumpets and the announcer introduce the US Olympic Equestrian Team or those who could attend anyway.  She see’s Lucy trot Rambo up the track, the way the redhead’s body glides on the horse is poetry to Sarah.  Then Chas on his stallion looking resplendent, and they’re all wearing their Olympic medals and waving to the crowd.  The sound of applause and cheering is loud, and Sarah claps with the crowd enjoying the spectacle.  Chas is carrying the trophy the winner of the derby will get, and he gives it to a man in a suit that places it on a stand for all to see.  The trophy is up for grabs, and now it’s up to man and beast to work together to win it.

The horses competing in the Kentucky Derby start entering the track, jockey on top in bright, colorful silks being led by one the hands employed by the ranch where the horse trains.  Flash Jester appears led by Harry Burns, the old trainer who forced her to leave Bob Simpson’s ranch.  Part of her feels a deep satisfaction knowing she’s pulled one over the old idiot again.  Who are you gonna blame this time, she wonders as hatred boils in her gut at the sight of the man.

Eventually, the horses race, and as history shows Always Dreaming wins, Flash Jester ran tenth, and Big Red (Norris’s horse) fourth.  The payout is as good as she expected and pays eleven dollars and forty cents for the win.  Sarah won more than one-hundred and fifteen thousand dollars in one race.  It stuns her, and she thinks that maybe this hobbling business isn’t so bad after all.  I get to have the wildest night of sex imaginable, then make a killing on the track, she thought, win/win.


“I need a break,” Sarah said to John after the race was over and they ate dinner at a restaurant to toast their glorious day.

“Yes, you have been working hard lately, and that’s why I think that gastro has hit you so hard,” he said smiling warmly at her.

“Our next meet is in a couple of weeks in Maryland,” Lucy said gazing at John.  “I think the horses competing from The Ponderosa are in terrific condition, so I think Sarah could easily take some time off until then.”

“Great Idea,” John said.  “I know a man who runs a riding academy in Maryland.  It’s a beautiful ranch; I can hook you up if you like?”

Sarah sucks in a quick breath and giggles.  “That would be nice, John, I can go and relax for a few weeks and meet you at the Loch Moy event.”

“Are any of your dad’s horses racing at the Preakness Stakes this year?” Chas asks then sips some white wine.

Sarah shrugs.  “I don’t know, they might race Big Red again, I guess,” she said blushing.  “Always Dreaming is the favorite after his win today, no doubt.”

Chas laughs.  “Yeah, I lost my money on that nag, Flash Jester,” he said rolling his eyes.  “I never saw such a fancied horse run so poorly.”

“I heard—” John said leaning forward and whispering, “the stewards thought he’d been hobbled or something.”

Hobbled?” Lucy shrieks with raised eyebrows.  “Nonsense, I saw the security around those stables, and no one would get near any horse.”

John shrugs.  “Where there’s a will there’s a way.”

“Um, did they investigate it?” Sarah asks feeling her heart race and her stomach roil.

John nods.  “Yes, but they could find nothing,” he said.  “Flash Jester just had a bad day; it can happen to any horse.”

“True,” Chas said nodding.  “I’ve seen countless horses in our sport seemingly in peak fitness and form before an event, and then have an absolute stinker on the day.”

“Same with riders,” Lucy adds.  “You just can’t emulate the pressure of an event during training.  Same goes for racehorses, right, Sarah.”

“Yes, once you add the big crowd and the loudspeakers yapping all the time, a racehorse can easily get spooked and put off,” Sarah said feeling herself relax.  “Like any athlete, the best are those who perform under the pressure of competition, not on the training track.”

Athletes don’t perform well if they spend the night before fucking either, she thought and grimaces.

“Well said, Sarah,” Chas said with a smile, mistaking her grimace for lack of confidence.  “Our horses are athletes in their own right, so true.”

“That’s why our Sarah is so good at her job,” John said with his chest puffed out.  “She knows how to get our horses in peak condition for competition.”

“Here, here,” Lucy shouts.  “The work you’ve done on Rambo has improved his performances, I really notice it.”

Sarah blushes.  “Well, I’m just doing my job,” she said turning away.

“I’ll call about that riding academy now,” John said, “and if you’re lucky you can go straight there rather than coming back to The Ponderosa.”

He calls, and the owner says it’s no problem; they have an empty cabin on the property Sarah can stay in for the next few weeks.

The next day, Sarah catches a plane to Maryland.


Read this story in our Members Area.

Leave a Reply

Your email address will not be published. Required fields are marked *