The Derby was over. All that remained was the rest of Equestrian events until the end of summer. Jack knew Emma never participated in the later competitions. But suddenly, her name was on nearly every roster for the season.
She walked through the barn door wearing a long dress with a slit down the front. The neckline was cut low, showing an ample amount of breasts. Sleeves were puffy and pulled low on her tanned arms. A slit ran up the front, showing off a slender leg and platform heels. It was impossible to believe she was only fifteen when she had the body of a woman and a beautiful face that rivaled those social media models.
Mr. Jack was carrying some equipment to his old truck in the back and securing it when she found him. He wiped his face of sweat before shutting the backdoors. The young girl watched from a bale of wheat as the much older man removed his shirt and downed some cold water.
"What's that?" She indicated to the back doors where his truck sat behind.
"Boar trap. The Collins had one malfunction. I have a spare, so I'm letting them borrow it."
"Oh." She stared at her phone, scrolling through her apps.
Jack came over to his little victim to admire her dress. "What a pretty thing."
"Thanks." She blushed and gave a genuine smile. "Miss Deveraux wanted to throw us a small party for our accomplishments. She said to wear something nice. I didn't want to outshine the other girls so I wore this."
Jack smirked. His little minx was quite the asshole. But it was what he liked about her. It allowed him to put her in her place.
Legs spread and beneath him, specifically.
"My friend Lydia asked me how I got so good at riding."
"Oh?" Jack walked over to check the driveway of the giant residential mansion. "What did you tell her?"
"That it was all me." Emma gave a boastful smile. "With a little bit of help."
Jack looked at the fifteen year old brat. "Just a little?"
She giggled and licked her lips.
There was no one home. Which explained why she was here earlier than normal. Otherwise she would have snuck out in the late evening. His little slut was wanting to feel some good dick-down. How can he blame her? It had been nearly two weeks since he last "trained" her. She was so impatient she had arrived all dolled up. And since she was his own personal doll...
Jack walked over to the teenager and caressed her neck, rubbing his thumb over her plump lips. "You're enjoying these trainings, aren't you, Miss Emma?"
She nodded, opening that pretty mouth when he pushed two fingers inside. She sucked on them greedily.
"Is that why you're here? Hmm? You want to get fucked hard so you can ride better?"
She stared up at him, her big beautiful blue eyes were so young and innocent, unaware of the predator he was taking advantage of a sexy child like her. Not that it mattered. This was their dark secret and if she remained ignorant there was nothing to fear. He planned to take full advantage until that time came around the corner.
"Come here."
She obeyed quickly, breathing unsteadily as he gripped her neck and kissed her roughly, slipping his tongue in and out of her mouth and against her tongue in a salacious manner. She was still too innocent for all he did to her, but that didn't matter. So long as he felt good, her joy would be secondary. Besides, she would eventually come to like it, like all things he did to her.
Emma moaned when he pulled the front of her dress down so he could fondle and pinch her nipples. Instinctively, her hand went to the front of his crotch to unzip his pants. She had been looking forward to this all day, getting wet at just the thought of being alone for their training while she was at the party earlier. Plus, no one would be home all weekend. Which meant...
"We can go to the house tonight," she said against his mouth, stroking his thick and long cock. He was already so hard and hot in her hands.
He chuckled. "You're very naughty, Miss Emma."
She blushed. "I just want us to be comfortable."
Easily, he picked her up and placed her on a higher wheat bale. Spreading her legs wide, Jack flipped her dress outward until that tiny and beautiful pussy was on full display.
Emma gasped and held the back of his head when he knelt between her legs. His tongue licked her up and down, driving in as deep as possible while his mouth sucked her off.
"OH MY GOD-JACK!" She was already so close, the heat building and building. "Jack, Jack, Jack, Jack, JACK!"
He watched her thrash and lurch. The orgasm he gave her was so good she cried and moaned, her chest pumping up and down for quick intakes of breath.
Unable to wait any longer, Jack pulled her forward and took his monstrous cock in his hand to angle it's head at the entrance of her pink vagina.
Heart pounding, Emma watched him rub his cock up and down her aching pussy, moaning as he teased her sensitive clit. The massive invasion came without warning. It was just pleasure and then the sudden pressure of his long cock forcing her vagina wide open.
She shut her eyes at the familiar burn, her small nails digging into his forearms as he started their training session. He never waited for her to fully adjust. Just forced himself inside her and then the heavy and long penetrations began. Even if it hurt her when he went too deep or too fast, she was forced to endure whatever training he wanted to do.
She hated that she liked it so much.
He swung his hips with purpose and intent, keeping the teenager wide open with the wide grip of his hands on the underside of her knees. She felt so fucking good. Her tight little cunt suctioned onto his thick girth and he watched with sick pleasure the contorted look of pain and pleasure on her beautiful face.
"Slow…slow…slow—AH! AH! AH!" She cried out, unable to stop him from digging further. "JACK! It's too deep!"
"You can handle it." All twelve inches of him were inside her now as he slammed away, grunting heavily with each stroke. "Besides, your pussy isn't complaining."
It wasn't. Even if she said no, her body told on her. Her tight cunt was dripping with want. It begged to be dicked down by the sick rapist that took advantage of her.
He adjusted his grip on her and the fifteen year old prepared herself for the most intense part. His long strokes became short and fast, with him always keeping himself buried deep inside. The slap of his hips between her legs was muffled only by their surrounding of wheat bales. She was unable to make any sounds but the occasional moans and cries when he became like this, her body overcome with pain and pleasure.
Jack tore into that sweet cunt of hers, stabbing into her cervix, feeling her orgasm consistently the longer he kept this up. Sweat covered the both of them, and it had nothing to do with this summer heat.
He was taken back when she managed to bring her boots to his chest in an attempt to kick him off. He just held on to her legs, his cock still inside the angry teenager.
"You're fucking hurting me." Emma was breathing hard from the intensity of this training.
Obliging her for the moment Jack slipped his cock from the vice-grip of her vagina.
"Show me. Where does it hurt."
The teenager brought her hand to her bellybutton. "Right here."
He massaged her midsection. This was important from time to time. Showing care but not too much of it. It had to be a perfect blend of toxicity between being uncaring and loving. The perfect trauma bond.
"Be more gentle," she complained. "You're always so rough."
"Is that what you really want?" He moved to her breast and squeezed it until she cried out. "Is that what it takes to being the best rider?"
A dark look came over his face and she was scared as he brought his cock back to her pussy and rammed it inside. There was no mercy as he fucked her furiously and relentlessly. She cries became screams with each penetrating stab of his cock. Orgasm after orgasms ripped through her.
"This is why we train. This is what you deserve." His grunts were heavy as he fucked the shit out of the young girl. "You spoiled, ungrateful little bitch. FUCK!"
Her screams of pain and pleasure turned him on to a degree he didn't think he'd ever get to, driving him to the brink of his own orgasm and he shouted as he finally came inside her. His cock jerked and jutted, spilling more and more semen in that vagina of hers.
He lay on top of the teen, the both of them catching their breath. When he finally pulled out, still very hard, white cum spilled from her pink sex.
"You're bleeding a bit." He left the girl to retrieve a towel. Carefully, he cleaned her up. "Are you okay?"
She stared at him with a light in her eyes, nodding timidly.
He kissed her gently, setting the towel down so he could thumb her sensitive clit. His tongue slipped onto her mouth, sliding against hers as he continued to rub her.
"You're so beautiful."
She gasped when he put three fingers inside her and started pumping up and down. Her head fell back as nothing but pleasure mounted. He sucked on her nipples, moving his hand faster and faster and faster, his fingers curled upward to reach her g-spot until she came with a cry. The small mewing noises she made was sweet and innocent.
He checked between her legs to make sure he got most of his cum out. There was a lot of it on the floor.
Emma had never really felt anything towards anyone. And while this was just supposed to be training between her and her grounds keeper, why did she feel a strange yearning and attachment to him? She didn't feel this way about Miss Deveraux. Then again, Miss Deveraux's training was nothing like Mr. Jack's.
All she could think about was Mr. Jack and the things they did together. She wanted to make him happy because he made her happy in a strange way. It was his compliments when he gave it. The way he paid attention to her. But he was also frightening and threatening. When he was like that she felt like a doe in headlights. Like she couldn't do anything but take the violent and euphoric training.
The young girl had no understanding of her mixed emotions, having grown a toxic attachment to her rapist.
"You did very well with today's training," Jack complimented after they were both dressed and more put together.
"Are you going to come to the house?" She stared at him pleadingly. "Freida always makes dinner and packs it away for me." And their private chef always made too much.
"This training is supposed to be a secret, Emma."
"I know, but like, no one is home. And I want to do more training. This is the perfect time to help me so I can win more."
He smiled. They were all excuses of hers. It was the human desire to enjoy sex for the purpose of procreation. It was embedded in all their DNAs. But she didn't need to know about all that just yet. No, he'd keep his sweet little victim in the dark just a while longer.
"You know, I could use a shower." It wasn't like he already didn't have a nice shower installed into the barn.
Her home was immaculate and rich. It was only the best of oak wood and marble columns, decorated by real fur rugs in front of a roaring fireplace and useless antiques that lined the walls and the occasional corner table.
Wearing an expensive robe that wasn't his, Jack ate like a king at the long dinning table while Emma chattered like an excited teenager that she was, telling him about everything and nothing. Stories about her friends, family, the one time pet dog that ran off and got stepped on by the neighbor's bull. She had also taken a shower and wore just a long t-shirt. No bra either as he could see her nipples peaking through the cotton.
"So what did you do when you found out your sister stole your favorite earrings?"
"Stepsister," she corrected. "I stole her favorite shoes and tossed them into Mrs. Ruth's disgusting pond." She wrinkled her nose. "It reminds me, I'm glad camp got cancelled this year. That pond is about as deadly as Mrs. Ruth's."
He let her pick at his food, occasionally feeding her some banana pudding. Just because he wanted to he pulled her to stand beside him so he could reach under her shirt to fondle her breast. Her eyes dilated with lust.
"Daddy is supposed to come back home next month."
"Oh yeah?" Jack rubbed her nipples, pressing her breasts together.
"Yeah…" She licked her lips. "How are we supposed to train when he's back?"
With ease he pulled her onto his lap. Her legs were at a near split to accommodate the bigger man's size. He undid his robe pulled the flaps aside. His cock was already semi hard and he closed his eyes as she took his penis and stroked him to a full and hardened stand.
"It's so big." She admired the veiny dick in her hand.
"Still can't believe you can take that?"
She smiled and nodded before getting back to the topic. "What are we going to do about training when he's back?"
"Your events will be over in two weeks." He watched the teenager use both hands to jerk him off. "We won't need to train for a while."
She didn't say anything but he knew she didn't like his answer from the way she looked down without any expression.
"I'll be on vacation when he gets back anyways. Around the same time you're supposed to be going to camp."
She frowned. "But the camp is cancelled."
"Exactly."
Her eyes widened. "I haven't told them yet."
"We can spend more time training far away from everyone if you wanted."
She squealed in joy and hugged him. "I can't wait, Mr. Jack! But how are we supposed to meet up?"
"Don't worry about the details." He held her close, running a hand up her slender back. "Just show me how happy you are."
She slipped her tongue into his mouth, kissing the older man with an expertise he taught her while he touched wherever he wanted on her body. There was no foreplay as he lifted the smaller girl over his heavy penis. She hissed as he forced her to sit on his monster cock.
"Hurts?" He groaned at how tight she was. God almighty, she could kill a man with her delicious cunt.
"Yeah…a little…" Her face told him it was more than a little, and the only way to overcome that was to get right into it.
He forced her up and down onto his massive dick. She was wet in no time even if she was still in pain. Each bounce made her cry out and the faster he went the wilder she became.
"MR. JACK!" She screamed as he continued to slam into her cervix with a violent force. "AH! AH! AH! AH!"
He tightened his hold on her and thrust into that pretty cunt of hers, forcing out orgasms. He liked that she was so young and dumb. It made the grooming even better and she wouldn't be able to tell between right and wrong when the time came. All she would know was that she wanted this dick down. She would need it.
This was what he was training her for. To blur the lines between these taboo acts and the morality of societal norms. She would forgive him for anything. He knew she was already infatuated with him.
He stood, carrying her with his cock still deep inside, purposefully stuffing her cervix and making her beg and cry. The fucking resumed once he set them down on the fur rug.
Slender legs curled against his hips as he fucked the fifteen year old ruthlessly. As many rooms as possible, Jack made sure to take advantage of her in. The weekend was a fuck fest of orgasms and cum. He filled her up so many times he'd be surprised if she wasn't pregnant by the end of it.
More. He needed more. And she begged for more. They were perfect for each other.
Before her stepmother and stepsister made it back from their weekend festivities he fucked her one last time in the master bedroom. He wanted to violate every personal space to assert his dominance over the girl he enjoyed raping.
"Jack! AH!" She struggled beneath him, clawing and grabbing at the silk sheets of her father's bed.
He slapped her ass, fucking her harder, enjoying how tight she was. God, her cunt was amazing. No matter how hard or deep he went, he couldn't ever fully break her.
He leaned back to get a good look at that glistening, young pussy taking every monstrous twelve inch of his cock.
"Please, cum! Please, cum! Please! JACK, PLEASE!" She screamed at his relentless assault, having no more energy to carry on.
He purposely held back just to get her to this point. He was addicted to her pain and pleasure. Her desperate pleas that would take him over the edge. His load was like a geyser as he spurted into her with a shout.
Panting, he fell over and stared at the overhead mirror. He was thoroughly spent after this weekend. Dick was still hard and wet from her pussy as it lay bobbing on his stomach. The beautiful young girl rearranged herself to lay on top of him, breathing just as hard. White cum smeared her inner thigh.
They were going to have to do something about birth controls so she didn't get pregnant.
"I don't want this to end." She closed her eyes in ignorant bliss. "That was so much fun."
In answer, Jack flipped her over again and shoved his cock right back inside, making her gasp.
"I didn't intend to stop just yet."