The Hobbler 5: The Preakness Stakes


Sarah gets back to her cabin at the riding academy in the early evening and has a long soak in the bath. She grabs her phone, taps the Bet360 app, and looks up the Preakness Stakes, the race Norris wants her to hobble next. Her eyes bulge at the odds for Cloud Computing, the horse Norris wants to win, currently at thirty-to-one. It’s a risk, she thought, but maybe Norris knows something I don’t. Studying the field, she sees the other horse being heavily backed apart from Always Dreaming is Classic Empire being the one who looks more likely to win with the former out of the way. Classic Empire is already at five-to-one and will shorten a lot before the race starts.

Still, an inside tip is something one shouldn’t ignore, and she bets ten thousand dollars on Cloud Computing to win and Ten thousand for a place just in case. After she’s done, she knows she can’t turn back now. Suddenly her phone rings, it’s Jillian, the academy manager.

“Hi, Jillian,” Sarah answers in a friendly tone.

“Sarah, how’s my favorite horse slut going?”

Sarah giggles. “Tired, I’m enjoying a hot bath right now.”

“I called around today, but you were out, did that man find you?”

Norris, Sarah thought. “You mean the old man in the black SUV this morning?” Sarah asks.

“Yeah, he came to the reception looking for you, I couldn’t get you on the phone, so I said it was OK,” Jillian said softly. “He said he knew you. I hope I did the right thing.”

I had the phone’s off while I was fucking your dog, she thought. “Yeah, it was OK, Jillian,” Sarah said. “He’s the man my father works for and was out here looking at foals or something. My parents told him I was here, so he decided to drop by for a surprise visit.”

“He said you grew up on his ranch.”

“Yeah, he’s like a second father to me,” Sarah said then mimicking vomiting in silence.

“OK, I just worried I did something wrong,” Jillian said. “Something about the man gave me the heebie-jeebies.” Jillian laughs nervously. “Anyway, I’m having a special night tomorrow night, if you’re interested. I have about ten coming to try bellyriding, are you interested?”

“Bellyriding—what the hell is that?”

“Oh, you’ll love it,” Jillian gushes. “We have these special harnesses that hold you beneath the horse’s belly, then we insert its cock into your cunt, and you go for a ride.”

Fuck, you mean as it walks or runs he pumps you with his cock?”

“Yeah, that’s the idea.”

“I’ve never heard of such a thing,” Sarah said, and part of her really wants to try it. “There’s only one problem.”


“As an official trainer for the US Olympic Equestrian Team, I can’t have people knowing about my, err, proclivities,” Sarah said feeling her heart race. “You understand, don’t you?”

“Yes, and like I said your secret is safe with me,” Jillian said. “I didn’t think, sorry. But if you’d like to try it, I can arrange a private lesson, just us two.”

“That sounds great, Jillian,” Sarah said and relaxes with a sigh. “That man who came today invited me to the Preakness Stakes, so I’ll be checking out in three days.”

“Oh, too bad,” Jillian said sounding genuinely disappointed. “I would love to have spent some more time with you—alone.”

Sarah knows what she means, yet the teen has no interest in eating Jillian’s pussy, she likes cock. “Maybe we can go belly riding together before I go,” Sarah said.

“I’ll organize it,” Jillian said. “I better go, talk to you later.”

“Yeah, see ya, Jillian.”

The call ends, and Sarah leans back into the tub and enjoys the healing balm of the hot water and the bath salts. Bellyriding, she thought with a snort. That’s a new one.


A couple of nights later, Jillian knocks on the cabin door at around ten pm and enters. “Are you ready?” she calls as Sarah comes to her and kisses her on the cheek.

“Ready as I’ll ever be,” Sarah said. “Won’t we freeze out there?”

“That warm jumper will see you OK, only your bottom half will be naked,” Jillian said. “You’ll be surprised how warm it is beneath the horse.”

“How does it work exactly?”

“The woman’s hands are fixed to ropes around both sides of the horse,” Jillian said. “She then uses her feet and hands to control how much penetration she receives from the horse cock inside her.”

“I’ve read online it can kill you,” Sarah said with a flushing face.

Jillian nods. “It can be dangerous, sure, but I only offer this to clients who are experienced horse fuckers,” she said. “I’ve seen you in action, and I know you take a hard fucking from a horse.”

“So where do we go?”

“Away from the cabins, that’s for sure,” Jillian said with a chuckle. “We have an old barn about a fifteen-minute walk from here where I can get you ready.”

“I’ve seen it, it looked empty and dilapidated.”

“Yeah, it’s a great cover for our bestiality services, and very private.”

Yes, I’ve already used the horses in there for my pleasure, Sarah thought. “OK, let’s go.”

They walk to the old barn, and Sarah’s pussy tingles with expectation and the memory of fucking her brains out with the two horse’s a few days ago. They go inside, and sure enough, the two black stallions are there tied to a post by their reins. One horse saddled in the traditional sense; the other has a strange harness on it.

“Aren’t you doing it too?” Sarah asks.

“Someone needs make sure the belly ridden horse doesn’t get too carried away, that’s how people get hurt,” Jillian said. “Besides I did it last night, and my poor pussy needs a rest. I’m sure you understand.”

Sarah giggles. “I sure do. What’s his name?”

Jillian smiles warmly. “Thunder, The stallion I’m riding is Big Ned.”

Sarah nods. “OK, so what do I do?”

“Take your pants and panties off first.”

“Oh, right.”

Sarah ties her hair into a bun and tucks a few stray hairs behind her ears. Then she kicks off her riding boots, soon followed by her pants and panties.

Jillian smiles and savors every inch of Sarah’s exposed flesh. “Nice, OK, hurry it up, Sarah.”

Sarah blushes and gazes at the stallions, knowing what comes next. “I think I’ll leave my boots on, it’s chilly, and they’re comfortable.”

Jillian can sense she wants to get the proverbial show on the road. “OK, let’s get you into the saddle, it’s a little strange at first, I know, but just put your head here, next to Thunder’s hindquarters, and wriggle your way to his front legs.”

Sarah nods appreciating the advice. Since she has read a few stories about bellyriding online after Jillian told her about it, Sarah feels prepared, or at least, as prepared as she can be. Sarah does as instructed and makes the awkward limbo-like motion to get into the saddle hanging below Thunders’ belly. It takes quite a bit of struggling and moving her body like a worm in the tight quarters of the horse’s underbelly, but she manages to get herself situated. Sarah raises her legs and arms, and the brunette ties them in ropes, which gives Jillian a spectacular view of her pussy.

“OK, strap me in, Jillian,” Sarah said with a shaky voice.

“Say no more.”

Jillian moves around and begins fastening her ankles and wrists to the side of Thunder’s body. Sarah pulls gently to get a feel for how tightly she’s held into place, and nods satisfied she isn’t going anywhere.

“Not too tight?” Jillian asks.

Sarah shakes her head. “No, it’s OK. The leather is cold, but it’ll warm up, I’m sure,” she said. “It’s soft though, which is nice. I was worried it would hurt.”

Jillian couldn’t believe how amazing Sarah appears in the bellyriding saddle. “We use nothing but the finest leather for this.”

The brunette riding master pulls out the box of shots. Sarah’s pussy is wet and engorged. The teen is naturally aroused, and Jillian can smell her dampness. Sarah is in heat and apparently looking forward to this.

Jillian laughs. “You’re wet already, and we haven’t even started.”

“I love horse cock, what can I say.”

Jillian starts masturbating Thunder. After a few seconds of her gentle fondling of the horse’s sheath, the animal’s phallus distends and drops. Jillian is quick, grabs the horse’s cock, and aims it at Sarah’s open pussy without putting it in.

“You’ll have to put it in, I don’t have any leverage,” Sarah said.

Jillian laughs. “This isn’t my first rodeo, Sarah.”

She begins to push the flat face of the horse’s head against Sarah’s wet pussy. It immediately slides off, causing Sarah’s stomach to tense as it rubs her clit.

The brunette MILF tries again, and this time she manages to push the edge of the blunt horse cock into Sarah’s pussy. Sarah winces as Jillian pushes the horse’s head past her pussy lips and into her wet pussy. The teen’s feet flex, as she feels the large cock familiarly stretches her cuntal walls, yet she bites her lip and says nothing. The stallion’s cock continues to fill with blood and push forward. Jillian is only massaging the horse now, not directing it as it pushes further into Sarah’s body. The teen winced again, gasping for air.

“Oh God—He’s HUGE—I love it.”

“Yeah, he’s hung like a horse—who knew,” Jillian said and giggles.

“Oh sure, laugh all you want, I’d like to see you getting a pussy full of horse dick.”

Jillian laughs. “You will one day, I promise.”

Sarah is breathing heavily now. “I’m afraid my pussy is so ruined that a horse cock is about all I can fuck these days.”

“I know the feeling.”

Jillian is indeed impressed that the teen is able to take, what already seems ten inches of hard horse cock into her body. The teen can apparently handle a big dick, but Thunder’s phallus appears insanely big compared to Sarah’s tiny cunt. Sarah’s cunt stretches to the point it would seem painful to the untrained eye, but also amazing.

“So far so good,” Sarah moans.

Jillian stops masturbating the stallion, when suddenly Sarah’s body goes stiff then breaks into an orgasmic shudder. The teen’s butt flexes hard as the hard cock inside of her seems to bottom out. Her body becomes bright red, and she isn’t breathing.

“Sarah. You OK, talk to me.”

Sarah isn’t saying anything or even breathing, but her whole body is shaking hard. Eventually, she groans, “OOOOOH—FAAAAAAARCK.”

“Jeez, Sarah, we haven’t even got going yet,” Jillian said rolling her eyes.

Sarah is taking deep-ragged breaths. “Holy shit—Fuck—Ahhhhh.” The teen’s butt is quivering and flexing until eventually her body seems to relax and she takes a deep breath. “Fuck, sorry, didn’t mean to cum so soon.”

“Are you alright to go on?”

“I’m not a man,” Sarah said sarcastically and laughs.

Sarah’s anus is clenching rhythmically, her pussy is pulsating too as her stomach heave, and her breasts jiggle. The teen’s nipples stick out of her jumper, and she appears exceptionally horny.

“OK, then let’s go for the ride of your life,” Jillian said mounting the other black stallion Sarah now knows is called Big Ned. “Now, if his dick falls out while we’re moving just yell out and tell me so I can put it back in.”

“Got it,” Sarah said.

They leave the barn, and Jillian sets off in a canter, the reins of Thunder tied to the saddle horn, pulling him along. Omigod, feel that cock sliding inside me, she thought amazed. As the thought flashes through her mind, Thunder begins cantering along the rough ground. Sarah’s body rocks in the bellyriding saddle, and the sound of the animals, heavy hooves hitting the ground is overwhelming. The now hard pink cockhead of the big stallion is sliding around inside her, bumping her, prodding and poking. She closes her eyes, feeling her clit throb, she so much wants to rub it, yet with her hands tied to the side of the beast, she can’t. Her next orgasm is now at the mercy of the stallion.

Every bump and gallop from the horse causes her body to slide along the cock impaling her wet cunt. She moans, sometimes screams as the fathead of the cock slams against her cervix, pushing it deeper into her body as more and more horse cock enters her. The bellyriding saddle purposely tied so her body will move, and it does. She can hear Thunder panting, and knows it isn’t the gallop causing it. Every bump and jolt causes mini-orgasms to billow through her body, causing her to shake and flush bright red.

Sarah’s mouth hangs open as if in some long silent scream, and blonde her hair jostles maniacally with the movement. Her next orgasm hits her with the force of a sledgehammer, surging from her cunt and clit through her body on a crest of outrageous orgasmic power. The teen’s body shakes and her cunt contracts wildly all over the stallion’s big cock. The animal, feeling some sexual heat itself, jumps and kicks its back legs out, the landing ramming its cock into her even deeper, and triggering another powerful burst of pleasure. The continual motion of the stallion is keeping Sarah in orgasm. The horse’s thick cock is jamming itself into her, filling her, and stretching her, is sending her to sensual heaven.

She cums repeatedly, and nearly blacks out from the rapturous spasms her body experiences. Her eyes roll back into her head, while her mouth hangs open, framed by her wild blonde hair. Eventually, even Thunder experiences the joy of this orgasmic cunt continuously cumming on its big cock, and can’t take it any longer. With a grunt and a gravelly low moan/growl that echoes and vibrates Sarah’s body, Thunder cums. The stud’s semen explodes from her still spasming cunt, spraying all over her lower stomach, groin, and upper thighs, then slowly dripping in big white clumps to the ground.

The stallion cums so hard, Sarah squeals as its hot semen fills her womb and stretches it, making her stomach bloat as if she were pregnant. Thunder suddenly slows and stops, panting from his run now and from this crazy pussy still squeezing his cock. Gradually Sarah calms until her body eventually sags into a sweaty, used blob of flesh. Sarah turns her head to see Jillian bending and staring at her wide-eyed.

“Are you OK?” Jillian asks.

“Omigod—Oh—fuck—that was wild,” Sarah moans between breaths.

“I think it’s time you took this to the next level,” Jillian said with a smirk.


The brunette MILF suddenly pulls the cock from Sarah’s pussy making the teen groan. She rubs a hand over Sarah’s cum-covered loins and starts sliding fingers up her asshole.

“Noooo, not that,” Sarah moans fighting the pleasure Jillian’s fingering is giving her.

“Yes, it’s time you took your riding to another level,” the brunette said hotly. “It’s time to break your anal cherry.”

Jillian reaches for the still erect horse cock and grabs it, sliding it against Sarah’s still gaping, cum-leaking pussy. The horse, feeling her cunt on the end of his dick thrust his hips forcefully.

“Ahhhhhhhhhhhhhhhh,” Sarah screams, as the thick cockhead didn’t go in her cunt, Jillian forces the massive cockhead inside her asshole.

“See, you can take it,” Jillian whispers as she rubs the teen’s clit.

“No—No—Oh God—IT HURTS,” Sarah wails.

However, with a wild laugh, Jillian mounts Big Ned and starts galloping along the trail to Sarah’s horror. Thunders thick cock slides inside her colon unhindered by an annoying cervix. Sarah now actually feels the size of Thunder as it pushes, jolts, and jams its way deep inside her belly. Her stomach boils as the horse cock shoves aside her innards with scant concern for the trauma it can cause. The blondes body stops swinging against him with his movement as she has too much thick cock impaled in her. Instead, she moves with the dick.

Her anus burns with intense pain, yet the friction of its slippery cock against her sphincter eventually builds to pleasure. Every time Thunders cock thrust into her ass, her stomach gets bigger, and as it pulls away, it gets smaller. Her clit starts throbbing; however, she can’t enjoy it until she discovers she can lift her bottom slightly, so her clit is rubbing against the horse’s furry belly. The friction of animal fur against clit sets off the sparks she wants so badly, as her anus glows from pleasure so unique to what’s she’s felt in the past. The combined forces meet in her stomach–clitoral and anal–joining to form a chorus of delight making her spasm with joy.

“Sarah, are you OK?” Jillian shouts.

Sarah concentrates hard on trying to squeeze her anus on the big cock of the horse, and she hears its guttural, throaty growls in response. This is one horny horse, she thought. Sarah works harder to get herself off, the deliciousness of humping her clit against the furry belly of the horse and the glowing fire in her anus does the trick, and an outpouring of orgasmic bliss drenches her from head to toe. Again, she starts spasming all over Thunders cock, and the horse whinnies in delight in return. He releases his seed deep inside her abdomen, its gooey warmth triggering anal orgasms in her until they stop by a river and his softening cock slips out of her ass followed by a torrent of semen.

Sarah is exhausted, so is the horse it seems. “Omigod that was fucking amazing” she calls to Jillian.

“I knew you were ready for it,” Jillian said in a small voice as she dismounts.

“Can I go again, up the ass?”

Jillian smiles and nods in the darkness. “Sure, but I’ll need to swap horses, I think Thunders done for now.”

After Sarah climbs out of the bellyriding saddle, she goes to the stream and washes her loins. In the darkness, she sees the tree stump she used her first day at The Maryland Riding Academy to fuck Onyx, the place where Jillian caught her in the act of bestiality.

“You brought me back here,” she said as Jillian removes the saddle off Big Ned.

“I thought it would be a beautiful memory for you on your last night here,” Jillian said and smiles.

“It is, Onyx is an amazing fuck,” Sarah said.

“I’ll miss you when you’re gone,” Jillian said. “It’s not often I meet a woman like me.”

“What about your bestiality clients?”

“We’re at a whole other level to most of them,” Jillian said pulling the bellyriding saddle off Thunder. “Will you ever come back for another visit?”

Sarah puts the regular saddle on Thunder while Jillian puts the bellyriding one on Big Ned. “Of course I will,” Sarah said. “But I have to get back to work.”

“Going to the Preakness Stakes is not work.”

If you knew what I’m gonna do there you’d think differently, Sarah thought. Then again, maybe you wouldn’t. “No, after that, we have a tournament at Loch Moy,” Sarah said.

“Ah, I know of it,” Jillian said. “We’re going to it as some of our riders are competing in the amateur events. Maybe I’ll see you there.”

“I hope so.”

Jillian finishes with the saddle and Sarah climbs into it again. The brunette MILF jerks Big Ned into hardness and holds it at Sarah’s wet cunt.

“So what’ll it be—ass or cunt?”

“Hmm—ass, definitely my ass,” Sarah said.

When Jillian has pushed the fat cockhead into the squirming teen’s asshole, she mounts Thunder and rides off at a gallop. Sarah moans loudly thinking she’ll have to use her ass when she hobbles Always Dreaming.


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