Jack stared at the spoiled princess in front of him. Emma Jane Lucas. Petite and innocent looking, she was everything opposite of a good young woman. At fifteen years old she was already one stuck up little shit. Entitled, demanding, quick to blame others for her own problems. It's why she hadn't won a single derby since her debut.
The teenager was too busy bossing around her derby contestants than working on her own skills. And now her father, who just happened to be the owner of the equestrian and derby events, finally stepped in. Either she won the next derby or he would remove her from future tournaments.
And the sick bastard Jack was, he planned to use that to his advantage.
The naive and pretty thing had showed up for their secret "training". He was the grounds keeper and took up residence in the family barn. It was a great distance away from the main house and they had all the quiet they needed on these private lands. The gathering storm outside would also be an added addition to coverage if needed. No one would be bothering them while he taught her how to becoming his personal obedient slut.
"Are you sure this is going to help me win?" The pretty blonde was blushed as she knelt before the much older ground keeper.
Jack unbuckled his belt, his cock already semi hard at the sight of her kneeling before him. "How do you think all the other girls got so good?"
"Miss Deveraux never taught me this."
"Miss Deveraux also isn't a man. And only men know how to win." He groaned as he took his big cock into hand and started stroking it. The twelve inch monster grew in length, stretching until the veins were visibly angry, tight with pressure. "Put this between your hands. Go on, take it."
She did as told, her slender fingers wrapping around his girthy and meaty flesh. In slow motions he taught her how to jerk him off, moving her hands back and forth and with just enough pressure on the grip. Once she got the hang of it he removed his hands and let her do it on her own, moaning as he closed his eyes.
"You said this is going to help me grip the reins better?"
He nodded, loving the way her smaller hands held and stroked him. Fuck, it had been a while since he had a woman. And she was every bit of one in spite of her age. Being fifteen didn't matter. She had the body of a woman with her c-cup breasts and perky ass.
"It's leaking." Emma stared in surprise at the white bead that started peaking from the head of his penis.
Jack leaned his head against the wooden posts of his bedroom quarter in the back of the barn. "You have to lick it."
"What?" She sounded appalled yet curious at the same time. "How is this supposed to help me?"
He gripped her hair instantly, tightening his hold as she yelped and cried. "You do as I say. If you want to win your next race and not get kicked out by your father, you do as I say, got it?"
She nodded in fear but stayed obedient. He knew the truth though. Emma was more scared of her father's rejection than him. For now. He was going to fuck her so hard he'd train her body to want more, and then she would have a different type of fear altogether.
The fear of not getting dicked down by his cock.
"Lick it. Now." He watched in disgusting lust as her pink tongue gingerly licked the precum from the tip of his penis. "Do it again."
"But I already did."
"You have to keep doing it. There's going to be more and we don't want it spilling out." He moaned. "This is part of your control when you ride. When you learn how to control the horse and guide it to victory. Do you understand?"
She didn't but nodded regardless. Mr. Jack had to know what he was talking about. She never paid him any mind, thinking he was just some old and lowly lumberjack that took care of their horses and land all day. But now, she felt very intimidated in his encompassing presence. Had felt that fear when he approached her a week ago, promising he could help her win after hearing her argument with her father. Desperate as she was, she agreed to it.
She just never expected to be doing this sort of training, too young to understand the older man's intention to fuck her into his own personal sex toy.
"Fuck." Her little licks on his sensitive cock was sweet and delightful. But he needed more. "Suck it. Put your mouth on it and suck it. Like that. Just like that. FUCK."
She tried to only take a little of it into her mouth since he was far too big. But she was helpless as he held her still and forced the girthy member into her mouth. Immediately she choked on it, gagging and coughing around it.
"Don't bite. Suck it." He held her tight as she squirmed and tried to push away. "Breathe through your nose. Calm down. That's it. Learn to breathe through those nostrils. Come on. No, no. Keep that mouth wide open. Relax that jaw. There we go."
With two hands on the back of her head he began lightly pumping his hips, forcing her to eat as much cock as possible.
"Keep sucking. Fuck." He watched as she did as told. Her beautiful lips were suctioned around his entire cock. Too small to take all of him but lord did she try. "Breathing control. This helps with your breathing."
She didn't understand. She wasn't the horse. She wasn't doing any running. How was this supposed to help?
"We're just getting started, princess. You just need to take more now. Open as wide as you can and relax those jaws."
Her little nails dug into his thighs as he forced almost his entire cock into the back of her throat and held it there for a moment before pulling it out. His membrane throbbed and bobbed, wet from the precum and her saliva.
"We need to get this nice and wet. See that? How shiny it is? That's what we want."
"For what?" She coughed.
"For making you the ultimate rider." He moved forward until she was backed against the wall. "Open that mouth of yours."
She did as told and he immediately slipped his cock all the way inside. This time though he started moving fast, his hips bucking in and out of her small mouth, his penis hitting the back of her throat. She tried to fight him off, thrashing as he went faster. If it wasn't for him keeping her head protected as he pumped in and out of her mouth, she'd have a concussion.
"Fuck, Emma. That's so good." Her mouth was fantastic. She was a fast learner too. She stopped fighting and eventually accepted it. Her wet gags turned him on so much.
When he finally pulled his cock from her mouth she spat out the salty taste of precum, letting it dribble down the side of her mouth.
She squealed when he turned her over. On her hands and knees she was helpless as he pulled her long t-shirt up to reveal her leggings. A big hand immediately went to her breasts and rubbed the nipple to a startling swell beneath her shirt. His big hands were hot and rough as they touched her softer skin. A spike of something euphoric went through her.
"Wait."
Light night struck outside, spooking the horses awake. She could hear them rustling in their stalls. This wasn't normal. This wasn't something she should be doing. But that one spark made her so curious.
He slowly pulled her leggings down, revealing the pinkest and prettiest pussy he had ever seen. "This is how we're going to make you the best rider."
She didn't say anything as he went back to rubbing her breasts, pulling on her nipples that were sensitive to each touch. He wiped her mouth clean with his other hand and she jumped when she felt fingers between her legs. He touched her where she peed, and a pleasuring sensation speared through her. It was exciting and it was scary at the same time.
"Your breathing is different." She was so wet, so slick. He kept playing with her clit, stroking himself as he watched her pretty pussy become even wetter.
Her entire body became hot the longer he touched her between her legs. He made her ache for something she didn't know all too well she needed.
"Does that feel good?" He asked quietly in the silence of their foreplay.
She nodded, her breath hitching with each pleasuring wave that built.
"Do you want to come for me?"
She didn't know what he meant but the pleasure started mounting more and more until finally it burst, erupting so strongly inside her that she cried out again and again, each blissful spasm making her hips move on their own as her pussy puckered and pulsed.
"Good girl. That's a very good girl." She was shaking from the experience of her first orgasm. The wet show she gave him had him licking his lips. These taboo sessions were going to be their darkest secrets, and by the time she learned what he was really doing it would be too late.
She'd be too addicted to care.
"Did you like that?"
She nodded. Emma had never felt anything like that before. It was amazing and dark and she felt she didn't know what life was before it, but she also felt like this shouldn't be happening. How could this feel so good, yet so wrong?
"Do you want to feel that again?"
She nodded hesitantly after a moment.
"Do you want more than that?"
There was more? That was already a lot. But she nodded after a long moment. That decision would be something she wasn't sure she'd come to regret or not.
"Spread your legs for me." He touched each thigh as she moved them apart, smiling sadistically because he knew she was his already. "Beautiful, Emma. Very nice. Your body is perfect for riding."
It was. She was toned in all the right places. Her perky ass was so plump he couldn't help but smack it once. She yelped and glared at him over her shoulder.
"I'm not a fucking horse." She yelped when he slapped her ass again.
"No, you're not." But he was going to ride her like one. "But a little pain is a lot of gain, and you need to understand how to handle it."
She squealed when he slapped her ass again and again, until her cheeks were flamed and red. Why? Why did she need to understand pain? None of this made sense. But she couldn't help but feel...excited.
Suddenly, something massive pressed against her vagina. She gasped as it continued to press inside, widening her sex in a way that felt wrong in spite of how her body wanted it. Like she would tear if it kept pushing in.
She went to move forward but he held her in place with his strength, rubbing the tip of his cock up and down her sensitive and pink pussy with a groan.
"What are you doing." She was breathing hard as lightning struck outside, unable to take her mind off what he was doing and so she turned her head to see him press against her. He was much bigger than her, towering over her like a bear about to eat her.
"I'm making you a woman."
Jack tightened his hold on her hips and pulled her towards him just as he pushed his cock inside her. All twelve inches force its way inside her tiny cunt. She was small. She was so tight. And best of all she made him feel fucking good. He ignored her screams and cries of denial as he rutted into her from behind. Blood and his precum helped to lubricate each slide, allowing him to fuck her as hard and deep as he wanted. She would only hurt a lot for a small amount of time. And then she'd grow to like it.
"STOP!" She cried painfully but he didn't seem to hear her. The slapping of his hips against her was louder than the thunder outside. "MR. JACK, PLEASE!"
She begged and sobbed, and still he tore through her like a hot knife, tearing her apart with every invasive pump.
"IT HURTS! STOP!" She grit her teeth as he only went faster, thrusting into her so deep she thought he was trying to kill her. "PLEASE STOP!"
God, she felt fucking amazing. She squeezed him so tight he became dizzy and had to stop himself from coming only by pulling out of her totally. The young teenager fell forward and wrapped herself up to cry.
"Do you like it?"
"FUCK YOU!" She screamed at him, tears running down her beautiful face. "I TOLD YOU IT FUCKING HURT!"
"Miss Emma, you're being dramatic. This is part of your training."
"NO! I HATE IT! I HATE YOU!"
"Miss Emma." The dark predatory look was back in his eyes as he addressed her. Fear locked her in place and she quieted down.
He sighed as if growing tired and moved to sit on the floor with her. The dim light showed his naked body and bobbing cock covered in blood. Her blood.
"If we don't get you prepared, if you don't win, it won't just be the derby you get thrown out of. It'll be your home here as well."
She shook her head, not believing him. "That's a lie."
"I overheard your father talking to your mother. If you don't do well on this next race, your father is going to send you to live with your mother." It was the truth and his golden ticket to trapping her with him.
She sat there, blood seeping from her vagina, next to the man she didn't realize was raping and taking advantage of her. All she could focus on was what he told her.
"I don't want you to go, Miss Emma." He feigned sadness. "This is your home."
After a moment of silent thought she turned around and got back on her knees. She would do anything to keep her home.
Jack smiled darkly as he got behind the pretty doll. This was all too easy.
"You'll feel good soon, Miss Emma. I promise you. It's only the first time that it hurts and then you'll like it."
She grit her teeth as he pressed his cock back inside her. There was a lot of resistance but no matter how much her pussy tried to stop him he was just too much. He was so deep inside. So deep.
"You'll feel good soon, Miss Emma."
She cried out as long deep strokes impaled her. All twelve inches of him slammed into the innocent girl, hurting her. But the more he trained her something else started to spring forward. Pleasure intertwined itself with the sharp pain.
Her stifled screams changed into moans. Jack grinned and started pumping into her like the wild stallions he took care of when the mares were in heat.
"This is how you win, Emma." He thrust into her brutally, making her cry out. "This is how you stay here."
"AH! AH! AH! AH!"
"You'll win for my cock. Do you understand?" He squeezed a perfect breast. "Say it."
"I'll win." She struggled to speak. It was getting too intense.
"For?"
"For your cock—AH! Fuck!" She fell forward, sweating from head to toe at this marathon she didn't expect to have for training. That same pressure as before was back. But this time it was much more than the first time.
"Take it, fucking take it!" He hollered as he ejaculated a load deep inside the young girl. She screamed again and again, the orgasm ripping through her so hard she blacked out momentarily.
Slowly, he pulled his cock from her, holding her ass in place so he could see his sperm spilling from her pink cunt. The night was still young, and there was still much more training he had to teach her.
Emma woke up in a gasp, moaning in painful delight at the slide of Jack's thick cock inside her aching vagina. He was on top of her this time, hands on either side of her head, his big body between her thighs as he forced every inch of his monster cock inside her tiny vagina.
"It's deep, it's deep, it's deep, FUCK, it's deep," she kept saying breathlessly, moaning with each stroke of pleasure. Unable to help herself she turned and bit his wrist when he started power thrusting into her, his hips swinging and rocking heavy into her.
"Fuck." Her pussy was so hot and tight. He couldn't hold back fast enough and the orgasm snuck up on him. He shouted and groaned as he came inside her again.
She lay still, feeling a burst of heat from him inside her. "What is that?"
"The secret you need to be the best rider," he lied effortlessly. "It's cum."
"Is this what the other girls have been doing to win?" She scoffed. "Fucking cheaters."
She moaned as his cock slipped out of her and had a strange desire to have him come back to her. She frowned at that. Mr. Jack was nowhere near her type. But she couldn't help but feel pulled to him for whatever reason.
"When can we do this again?" She pulled her leggings on and straightened her long t-shirt.
"When you win the next derby race." He remained naked, watching her pull on her rain boots.
"That's not until next week. I'll still need to train, right?"
He didn't answer her, just walked her to the barn opening. The rain was gone now but there was still thunder in the distance.
"Mr. Jack, I want to train. I want to win." She stood in front of the older man.
Seeing her so innocent, so pretty, with her long dark hair flying in the wind and her nipples peaking through the t-shirt she wore, he couldn't help but lean down and force a kiss onto her. It was a hard and deep kiss, one she could never get from those soy boys that flaunted after her. He drove his tongue down her throat and mashed their lips together in a ferocity that made her moan in pleasure and fear. Her eyes were dilated when he pulled back.
She screamed as he fucked her against the barn door that led to an open green pasture. The horses in the nearby stalls were the only witness to this taboo act.
"Jack!" He was ruthless as he slammed into her from behind. If he kept this up he was going to break her. "AH! AH! AH! FUCK!"
She jerked away when it was too much, her pussy still unable to take his brutality. He punished her for it, slapping her ass viciously before popping it out so she was leaned forward, her only anchor the wooden frame of the barn.
He stabbed her repeatedly with his cock, making each thrust harder than the last. Tears ran down her face as she begged him to be more gentle.
"This is the training you wanted. This is the training you get."
He was so deep in her gut like this. She could feel every solid inch of him burning through her. Even when she had an orgasm he beat her with his cock into another one and another one until he finally came, shouting into her hair as he emptied himself and held onto her.
"Take a shower when you get home."
She nodded, still breathing hard from the intense training. She groaned when he slipped his cock out of her. Hot semen fell from her pussy, a reminder for him to keep track of her period.
"When was the last time you bled?" The last thing he needed was a pregnant teenager walking around.
"I just finished a few days ago."
There were a lot of things in his favor tonight. He helped her by pulling her leggings back up. She pulled his face down to lick his lips and pull him in for another kiss.
She came back every night for the next week. He pumped her with enough semen for a sperm bank by the time race day came. And when she took first place they celebrated by doing what they did best together.
Training.