The Most Pleasurable Pain

Sunlight peeked through the shades as Devon awoke from a restless slumber. Pulling the covers off of her, she nearly stepped on Stephen’s sleeping form. Kneeling beside him she gently caressed his cheek. The feel of his skin under her fingers was smooth and warm. Tracing the line of his face, she didn’t notice him watching her. Grabbing her hand, he brought it to his lips and kissed her palm. “Good morning Mistress Devon.”
“Good morning Stephen. Are you ready for today?”
“Yes Mistress Devon, I only want to please you. I am yours to do with as you desire.”
Devon left the bedroom to retrieve her bag from the patio. Stephen knelt at attention bowing his head as she came back in the bedroom.
“Stephen, do you employ a pony trainer?”
“Yes, Mistress Devon. Randy is my assistant trainer.”
“Tell him that I require his presence immediately.”
Stephen rose from his knees and left quickly. Devon took a shower and dressed herself in all leather. She was zipping her boot when Stephen returned with Randy. Extending her hand to Randy, she introduced herself. Randy shook her hand with an extremely firm grip. He was 5'10, slim build, deeply tanned with very short black hair and steel grey eyes.
“Randy, did Stephen inform you of why I requested your presence?” asked Devon.
“No Devon, Stephen only told me that you wanted to see me immediately.”
“Stephen has agreed to be a pony for the weekend and I would like you to assist me in training him. I do not have a lot of experience and I need a professional.”
“I will assist you in any way that you need me. I have one question though, why has he submitted?”
“I appreciate your help, thank you. And as for your curiosity, Stephen has submitted to me because it pleases me. Any more questions?” asked Devon sharply.
“No mistress.” replied Randy.
“Good, I need you to take my pony to the stables and have him harnessed and ready in twenty minutes. I feel like going for a drive today.”
Randy snapped Stephen’s lead on his collar.
“Before you leave, take this bag. It contains the harness that I want Stephen to wear, including the matching tail.”
“He will be harnessed and waiting for you in the training ring, Mistress Devon.” She nodded to him as she handed him the bag.
Randy exited the room with Stephen in tow as Devon went to the bathroom to finish getting ready.
The training ring was located 100ft south from the house and 300ft to the east of the horse stables. Walking briskly to the ring, Devon passed several small buildings and one rather large building that had several small windows running the length of it. There were double doors at the entrance of the building where Stephen was standing proudly wearing her harness. The harness was white leather with a royal blue inlay that made a striking contrast to Stephen’s tan body. The bridle Stephen wore consisted of a single leather piece that formed a loop around his head attaching to silver O rings that held a thin plastic bit and a set of long driving reins. The harness consisted of a belt with two large straps attached to the top of the belt that cris-crossed over his chest and shoulders. There were two smaller straps extending downward from the belt that looped around the cart shafts. Stephen’s wrist cuffs were attached to the shafts which caused his hands to wrap around them. The cart itself was a small white one-seater with small silver spoke wheels. The cart reminded Devon of a backwards wheelbarrow. Randy was inserting the dildo tail into Stephen’s asshole as she approached. The tail dildo was light blond and fell to just an inch above Stephen’s feet which were shod in thick white soled boots.
“Mistress Devon your pony is ready” said Randy as he handed her a long driving whip and the reins. Inspecting the straps for a tight fit, she stroked the whip slowly over Stephen’s thighs and ass. She continued her exploration, sliding the whip across his chest and neck. Stephen watched her slide the whip over him with fear and anticipation in his eyes. He shuddered when she gently stroked his head through the bridle. Stepping away from him she gathered up the reins and seated herself in the cart. “Walk” she commanded as she cracked the whip over his flanks. He moved immediately forward, lifting his knees high in the air. She tugged the right rein to signal him right. Stephen responded immediately and turned with ease. She drove him towards the patch of woods she had seen the night before from the balcony. The path was smooth and even which was perfect for galloping. She laid the whip sharply and repeatedly across his flanks as he picked up speed. Trees became a blur as she spurned him on faster until he was running full out. She felt giddy as the wind whipped through her hair. Stephen kept up the break neck speed for about a mile when she felt him falter slightly. Not wanting to risk a fall or serious injury to either of them, she tugged his reins gently until he slowed down to a walk. Stephen was sweating profusely and his breathing was labored due to the bit obstructing his airflow. Walking him through the woods, it felt surreal. She couldn’t believe that her former master was now her submissive; her very own pony to do with as she pleased. God, he was beautiful with head held high, long lean muscles tanned and taut with his tail streaming as he snorted in a stallion like matter. Devon continued to follow the trail until she glimpsed a small portion of the pony stables through the trees.
Devon commanded Stephen to trot as more of the stable came into view. He responded quickly and with precision as he pranced and snorted to the stable doors. She halted him to a stop, dismounted the cart, and watched as Stephen tossed his head and stamped his feet.
“Easy boy, that’s a good pony” she murmured to him as she stroked his hair to calm him. Randy was waiting for them as he stepped from the barn with a bucket of soap and hot water.
“Clean him, feed him, and water him, I will back for him in one hour to practice dressage” instructed Devon as she handed Randy the reins. Stephen was led into the stables as Devon made her way back to the house.

An hour later Devon stepped into the training ring where Stephen, bridled and tailed stood patiently. Randy came out of the tack room and handed her a very short dressage whip that had a knotted piece of leather on the end. Gathering the reins and the whip, she put him through his paces. Snapping the crop in her left hand and tugging the reins with her right, she walked and trotted him in a circle. Knowing that he hadn’t had formal pony training in years, she gave verbal cues. She had him perform the piaffe, a collected trot which he did with grace and precision. His head held high, body and cock erect, knees lifting and lowering in place, Stephen pranced and made an elaborate spectacle of himself. She knew that this type of behavior wasn’t acceptable in pony dressage, but she didn’t care. His prancing and snorting was meant for her pleasure and enjoyment. Commanding him to stop, she praised him by stroking his head and whacking him across the thighs leaving a nice red stripe. Leading him to the center of the ring, she instructed him to kneel. Turning towards the gate, Randy had a grim look on his face as he observed Stephen’s performance.
“Is there a problem Randy?” Devon asked.
“Your pony is high-strung, untrained, and lacks discipline.” said Randy.
“What do you suggest be done about my cheeky pony?”
“He needs to be whipped thoroughly and with no disrespect Mistress Devon, he needs a more experienced trainer to correct bad habits.”
“You are the professional Randy. Why don’t you train him for awhile and I will observe.”
Randy was unsure if he should or not, Stephen was his employer and he didn’t want to lose his job. Devon sensing his apprehension assured him that there wouldn’t be any repercussions for obeying her. Stephen had told her to utilize his staff as she saw fit. As Randy took control of Stephen, Devon went to the entrance gate and sat down on a bale of straw. Randy lunged Stephen in a circle until he was breathing hard. The prancing and head tossing quickly stopped as Randy showed Stephen this wasn’t for his pleasure. The pleasure was only reserved for his trainer and master. Devon instructed Randy to present Stephen in various poses to show his compliancy and his desire to please her. Randy went straight to work displaying Stephen in the most open humiliating ways. Stephen scrambled into position; opening and bending, showing his ass and cock as Randy commanded with voice and whip. The obedience of Stephen’s flesh, as he did his best to please Randy made Devon tremble. She rubbed her thighs together as she felt herself grow wet. Heat spread throughout her body as she imagined Stephen bucking underneath her as he bucked under Randy’s hand and whip. Losing herself in the fantasy, she felt the beginning tremors of an orgasm. Controlling her breathing and concentration, she held her orgasm back as Stephen’s heated gaze bore into her. She knew he had been watching her which made her shiver with excitement. Of course, he would have to be punished for that little indiscretion later when they were alone. As for now, she would sit back and enjoy the performance he displayed purely for her pleasure and approval.