She suddenly froze in place.
“Regan, walk.”
“I'm scared. I'm going to get hurt. Please, come closer. Hold my hand?”
“On your hands and knees, Regan. Now!” came the order.
Regan dropped quickly, feeling the dirt with her hands as she kneeled upon the hard ground. She heard the sound of swishing and cried out as a deep burn bit into the back of her thighs.
“Ow! No more! Please! Ow! I'm sorry I disobeyed you!” Regan howled as the switch cut into her flesh another three times.
“Follow my footsteps, Regan. Stay down there.”
Sniffling, Regan crawled after him, listening carefully for the crunching sound of his footsteps upon the dirt. She felt small pits in the path, but nothing that would have caused her to fall. Again, she began to feel an odd sense of shame for having failed him. Determined to prove herself to him, she silently followed the sound of his footfalls, ignoring the tenderness of her soft-skinned palms and knees.
He allowed her to rest after a while and checked her body for damage. She was hot and sweaty by that time and felt the summer sun heating up the area around her.
“Go find the stream. It's clean, and you can drink from it, but do not use your hands. No, stay on your knees. Standing is now a privilege you must earn.”
He dismissed her with a hearty smack to the rump, making her emit another sharp yelp. Regan pouted, tilting her head to listen for the sound of rushing liquid. Carefully, she picked her way toward the gurgling stream and squealed joyfully when her hands landed in the icy water. She did it!
Thirsty and hot, she dunked her face into the flow, drinking the sweetness heartily as it cooled her flushed face. She lifted her head at the sound of crunching grass, sensing Master Jay next to her. She tightened her body as he poured handfuls of cold water over her naked flesh and then pushed her towards the center of the stream bed. It was no deeper than her thighs, and it was frigidly cold, but that did not stop him from thoroughly rinsing her and cooling her hot skin down. He touched every part of her, every crevice, and explored her shivering body freely as she clenched her teeth at the combination of cold water, the hot sun, a light breeze, and the touch of his hands upon her flesh.
Regan gulped, suddenly needing to pee. Should she try to hold it?
Somehow, he must have sensed her discomfort. “We drink this water, so you may go onto the stream bed and squat on the dirt, Regan. Do not stand or use your hands.”
“But…”
“There is no but, pet. Obey me, or I cut another switch.”
Mortified, Regan crawled out of the water and, in ultimate humiliation, peed before him like an animal. His praise filled the air, proclaiming loudly that she was a ‘good girl’. Despite her confusion coupled with the words that implied she was nothing more than a well-behaved pet, Regan discovered that she flushed with pleasure at his praise. When had he opened the door to her true submissive? And what would be his next step?
Regan was collapsing on the ground by the time they began the walk back to the house. He had not allowed her to rise even once, knowing her palms and knees would be bruised and very sore, but that her lesson would be well-learned. He took pity on her as she whimpered quietly behind him, and finally scooped her up into his arms.
“We need to work on your endurance, my girl,” he said as she sighed with relief. “After you eat, you may nap for a while.”
“But, I don't… Yes, Sir.” Regan sighed, biting back a yawn. Every muscle in her body was aching, even ones she hadn’t even known she had!
Tenderly placing every morsel into her mouth with his bare fingers, he fed her while she kneeled on the ground. Several times, he would place one finger into her mouth to suck, and she sensed his smile as she did so eagerly.
After eating, he groomed her—that was the only way she could explain the way in which he prepared her for her nap. He snapped the collar he had used the day before around her neck and tied her to a table, again on her hands and knees. Regan fought to stay upright as he cleansed every inch of her body, followed by a long, deep massage of her legs, back, and arms. He brushed her hair gently and then inserted his finger into her mouth. It had a rubber tip that felt like a toothbrush on it! The soft, plastic bristles that were rubbing her teeth and gums were almost as soothing as the hand that lovingly stroked her still-stinging backside and thighs.
Her eyes grew heavy and she leaned against him, humming to herself.
* * *
“Tired, sleepy head?”
Groggily, Regan forced to turn in the direction of his voice. “Every muscle I have hates you right now,” she groaned.
“You'll get over it. By now you should understand that my orders are much easier to obey than the lessons that follow when you challenge them.”
“I guess I'm a slow learner sometimes.” Regan groaned again. “I am so stiff. Will you…? Please…?”
“Ask me,” he commanded.
“Would you please rub me down? Everything hurts,” Regan asked quietly, disbelieving that she was actually at the point of requesting comfort from her abductor!
“I would be more than happy to. I even have some nice, deep heating ointment to use. I also noticed that you only used up one of your questions today. Are you losing interest?”
“No. It just, well, it doesn't matter to me right now. Oh… Thank you,” Regan mumbled. He started at her feet, working his way up the entire length of her body and careful not to touch the sensitive skin of her sex or the tender flesh between her bottom cheeks with the ointment. When he turned her over to her stomach and began to massage his hard fingers into the ample flesh of her bottom, Regan lifted herself as an offering.
“Do you want something, darling?” he asked with amusement.
“I want you to fuck me again. Please,” Regan forced out. Master Jay said nothing as he plunged a finger into her tight pucker and held it there, waiting for her reaction. At first, Regan was surprised by the abrupt penetration, followed by the unusual warming of the skin surrounding his finger. The sensation grew hot and increasingly uncomfortable. Regan began to squirm under his hand as the ointment burned into her bottom hole.
“Please… Please! Take it out! It burns!” she begged, bucking up and down to escape. She froze as she felt his manhood penetrate her sex, and moaned with delight as the painful heat turned to pleasure as he took her slowly and carefully, not once removing the offending, ointment-covered digit from her rosy pucker. Regan lifted her bottom high, ignoring the feeling that she was presenting her body as a human sacrifice, and pumped herself against him. Ignoring her conservative mindset, she ordered him to pump faster and harder, to prove to her that he could satisfy her needs. Foreign words and phrases slipped past her lips, and she felt whorishly free and knew that she would die a happy woman should her heart explode while she came.
“Before you sleep, you are to ask me to spank your bottom until it is beet red,” he said, watching as she began to dose.
“But I don't want a spanking,” Regan said in a tiny voice.
“Did I ask you if you wanted one?”
“No, but…”
“I want this for my pleasure. Now ask.”
“But, I am so sore already!”
“Again, your disobedience disappoints me. Good night, Regan.”
“Wait! Aren't you going to stay here?”
“Not tonight. I want a pet that cherishes her master. You need to learn how to cherish the gifts given you, without question or suspicion. Good night.”
His voice reeked of disappointment, and Regan begged forgiveness as she heard him leave the room and shut the door behind him. Her wrists restrained snugly by the cuffs at the head of the bed, Regan simply buried her face in the flesh of her arm and cried bitterly. Why couldn't she learn?
Chapter Six
Regan opened her eyes, surprised to see light streaming into the room. She lifted her hands to her face, finding it devoid of the contraptions that he had sealed over her eyes. Slowly, sh
e sat up in the bed, also realizing that her restraints had been removed. Wincing, she reached behind her, recalling the punishment she experienced the night before.
He had returned the night before, carrying with him a heavy leather flogger with which he spared nothing. He had been very severe with her, lashing her bottom and the back of her thighs clear down to her knees. He had made her hold her cheeks wide apart as he whipped her tender crack and sex with the horsehair from the plug before reinserting it into her bottom.
She’d felt shame, realizing how he had trusted her to obey him, and how she had failed.
Was this his way of letting her go? Or was he telling her that she was no longer worth the effort he had given her? She had been with him only the two nights, and she was convinced that he had tired of her presence.
Regan slowly stood, her body crying out in pain as she hobbled to the bathroom. Still groggy, she failed to see the dozens of irises throughout the room, or the tray of giant chocolate covered strawberries near the window. She entered the bathroom, genuinely surprised to see the tub was already filled and ready for her. Gingerly, she stepped in and carefully sunk to the bottom. She then noticed sliced peaches and a glass of orange juice perched on the side of the tub.
Regan sipped the juice and then leaned back to submerge her head under the water, holding her breath as she listened to the bubbling jets around her. She was confused. Was this a final farewell to show her what she had missed out on because of her disobedience? She washed her hair in the fragrant shampoo that he had found in her favorite scent, and her heart sunk even deeper.
He had done so much for her! But wait—she’d struggled, she hadn’t been a willing participant of any of this. That is… she hadn’t been at first!
Regan wiped the salty tears that burned her eyes and stood up to wrap the towel around her body. She had finally found a man who thought her to be smart, beautiful, funny, and understood her needs. And she’d chased him off.
“Damn you, Jay. Everything would have been fine if you’d never shown your face!” she cursed, walking back into the room. It was then she noticed the flowers and the strawberries, and grief struck her deeply once again. All because she was not able to conquer her foolish pride…
The phone next to the bed rang. Hesitating, she lifted it to her ear.
“Are you awake, Regan?” his low voice asked.
“Yes. Listen, about yesterday. I am so sorry. I know I should have listened to you…”
“Are you dressed?”
“No. I have nothing here to wear except that t-shirt. Jay, please forgive me. I promise I will do better!” Regan broke into tears, clutching the phone. “You were right. I am lonely, and I do need someone who understands me. I don’t want to… to lose our… well, whatever it is we have.”
“In the closet is a box. Follow the directions very carefully,” he said firmly and without emotion. “Pay attention to each detail. When you are finished, call the number on the cover. Am I understood?”
“Yes, Sir. Does this mean you’re giving me a second chance?”
“You are such a silly girl. Do you think a little disobedience is going to scare me off? You do need to mind better, and today you will learn. Do as you are told.”
“Yes, Sir,” Regan said, her hands clinging to the receiver as she sighed with relief before slowly hanging up. She dropped her towel and walked to the closet, opening it to find a large box with her name written across the top of it. It was heavy, and Regan took it to the bed to open it, gasping as her eyes fell upon the contents.
On top was the horsetail plug with a note…
My Dearest,
You remember this? You know where I desire it to be placed. Use the lube on the strawberry tray to help you. Follow these instructions step by step, do not go out of order or unpack anything until you have completed the prior instruction. Show me you can obey, Regan, and make both of us proud.
With Love, Master J
Swallowing, Regan looked at the plug. It was about five inches long and wide at the base, with long, silky brown horse hair protruding from the end.
With a sigh, Regan went to the tray and found he had left chocolate-and-strawberry-flavored lubricant. Glancing guiltily around the room to ensure that she was not being watched, Regan tasted the lube out of curiosity.
“Damn, these taste almost as good as the real thing!” she exclaimed aloud.
Carefully, she dripped the lube on the plug and then reached between her legs to find her still tender bottom hole. She tried to follow the example he had set the night before by moistening the area and then gently probing and stretching her reluctant entryway as she tried to relax. Regan squatted, feeling the heat of her blush covering her body. She tried to press it in, but the pain was too much. Tears in her eyes, she tried to think of what to do. Remembering one of her stories about the heroine having to insert her own butt plug, Regan repeated the event.
She took the plug into the bathroom and set it on the edge of the tub. Carefully, she lowered herself onto the tip, making sure it was centered at her bottom hole. She pressed down, pushing out, and felt her eyes widen as it popped deep into place. She sat for a moment, trying to adjust to the odd sensation within her. Because of the length of the plug, she felt as though she had to arch her back, making her bottom stick out more. It also made sitting impossible.
Groaning, Regan looked at the tail in the mirror. She could not help the smile that fell across her face. She wiggled her bottom, watching the long tail swish back and forth, tickling her naked thighs. With a naughty giggle, she headed back to the box.
A good little pony has special needs. Since you have not been saddle-broken yet, we will start you with the basics. We must protect those darling little feet with nice, solid shoes. Put the special leg binders on first and then shod yourself.
Regan grinned as she removed a pair of high-heeled boots, complete with horseshoes on the sole! They were black leather and adorned in buckles and straps.
“I’ll say this much, Master Jay,” Regan spoke aloud as she pulled on the thigh highs and then slipped the boots over her feet, “you have good taste. I would wear these pretty things anywhere!”
Next came a simple black garter belt to help hold up the hose. The bands were trimmed in tiny silver bells that jingled as she hooked them to the stocking edges. She paused to view her half-dressed body in the mirror. She turned and wiggled again, grinning as the tiny bells tinkled merrily as the tail swayed back and forth.
Regan wrinkled her nose as she pulled a black leather contraption out next: the harness.
Ordinarily, your master would dress and bridle you, my darling. This first time, though, I wanted you to have the time to enjoy each little gift and the pleasure of adorning yourself. By now, I am certain you see how incredibly lovely you are.
It took Regan nearly fifteen minutes to figure out how the harness was to be worn. She could not determine if she felt more excitement or shock as she slid the chastity belt between her legs, careful to pull the tail through the open section in the back. She shrugged into the upper harness and adjusted the buckles that held her bare breasts upright. The leather was studded with chrome studs, crisscrossing over her torso. Following the instructions, she cinched the waist, surprised to discover curves that she had never noticed. Glancing again in the mirror, Regan had to admit… she looked hotter than hell!
Gauntlets with bells were slipped over her wrists, followed by a high neck collar that kept her head held high. Finally, the outfit was complete, except for one item.
Call the number on the box and then place your bridle over your head. Yes, my dearest, you will, once again, be blindfolded.
Regan obeyed quickly, smiling at the happy sound of the bells with each movement. The bridle fit like a harness over the top of her head, complete with blinders. She also noticed the small bit and reins. On impulse, she inserted the rubber bit between her teeth. He did not say she had to gag herself, but she wanted to show him that she had repented.
>
Regan was standing tall and proud, fully decked in the regalia, when she heard Master Jay enter.
“My God, Regan… you are the most amazing thing I have ever seen,” he forced out. Regan lifted her head higher, hearing his footsteps as he approached her. She felt her skin quiver as he stroked her.
“You have stolen my breath, my beautiful pony,” he whispered into the back of her neck, kissing the nape. “Look how proud you are! And you even placed the bit between your teeth without being told. I am very, very pleased. I knew you would be lovely, but I did not expect regal!”
Regan pulled herself up even higher than her five-foot-five height, lifting her chin and hoping he could see her smile. She stood in place as he tightened the tack and made some adjustments, certain to secure the rubber snaffle firmly in her mouth. She felt him rub something cold to the top of her right thigh and tilted her head, making her bridle bells ring.
“It is just a temporary brand to claim you as mine. Maybe one day you will want a real one.”
Regan nodded her head in understanding, purring as his hand wrapped around her thigh and checked the chastity belt that covered her crotch. He was humming the tune again, but this time Regan did not strain her ears to recognize it. It didn’t matter. He was back, and he hadn’t abandoned her.
* * *
Bit in her mouth, Regan was unable to ask any questions, her only noises being grunts, groans, and whines. She found if she relaxed her jaw, it eased the discomfort of having the soft rubber bar between her back teeth. The plug, however, was a different problem. Not only was it uncomfortable due to the length and girth, but progressively painful as she tried to sit.
Master Jay laughed, pushing her forward. “No, no, honey. Ponies don’t sit; they kneel or they stand. You will be a standing pony, I think. You are incredible, and I can’t wait to train you. For now on, one stomp means yes, and two stomps means no.”
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