By Raybound

The Pony Race

After meeting those two hot leather men at the bar and having a hot session with them, I never could have imagined that our next encounter would involve one of my deep secret fantasies — pony play! Here’s how it all unfolded…

The pre dawn sky was streaked with pink as I arrived home, the morning sun had not yet risen above the horizon. I was still feeling lightheaded from the effect of the endorphins that had coursed through my body like a wild river as I had endured the controlled torture of the night’s action. I went straight to bed and slept late, right through into the afternoon, breakfasting some time after three. Wild dreams filled with the images of the two leathermen had chased around my head shortly before I had woken. I put together the events of the previous night, realising that my life had been changed forever. This was one genie that I certainly didn’t want to put back in the bottle.

Sleeping on my stomach had alleviated some of the pain from the weals that criss crossed my back and buttocks. Tom had wielded the singletail with enthusiasm. His swollen leather clad crotch had been in my sight line throughout the whipping, growing inexorably as the excitement of delivering the thrashing worked its way into his brain.

Stepping from the shower I glanced over my shoulder at the full length mirrored wall. The lines formed an intricate pattern across the whole of my body from thighs up across my entire back, varying from red to blue black as the bruising matured. My cock stiffened involuntarily at the sight of it, recalling the deep eroticism of the previous evening. Driven by those images of my leather clad captors I stepped back into the shower cubicle and grabbed the now rock hard shaft of my penis. Standing beneath the hot stream I stroked myself slowly at first, the water cascading over my face. I stroked harder, faster as the intensity of the feeling grew. I heard my own screams reverberating inside the confined space as the thick bolt of creamy cum shot from me, splattering against the wet glass and trickling down. Still panting from the intensity of the orgasm i plucked the shower head from its holder and let the water chase the thick, gooey skeins of semen down the plug hole.

Towelling myself off I walked through to the dining room just in my tight black briefs. I loved the feel of them, the way that they confined my cock shaft. I couldn’t resist admiring myself briefly in the mirror. At thirty five I had a nice, hard body with good muscle tone. I’m five ten and one seventy five, not bad looking with thick blonde hair I thought that Tom and Jed probably considered me a bit of a catch. I took the slip of paper that Jed had given me from the pocket of the chinos that hung across the chair back. Turning it over I saw his e mail address “jedb79.” I guessed that the 79 was his birth year. I flipped open my tablet and typed it in.

Hi Jed. I just wanted to say a thank you for last night. It really was a great experience. I’m a little sore from meeting with Tom’s singletail but definitely up for another session. Just let me know when suits you. Simon

I had walked through to the kitchen and was pouring myself a coffee when I heard the ping of an arriving mail. Opening it I saw the reply.

“Hi there. That was some session! Tom and myself had an awful lot of fun, that is a talented mouth you have. We would be keen to meet up and discuss how we move this forward. If you are interested meet us at Carberry’s Motel. It’s a couple of miles further on than the Starlight bar. We will be there at eight. Jed.

I sat for a few minutes re reading the mail. I felt another stirring in my loins at the thought of being in their company again. I slipped into the drivers seat of the VW at seven thirty and headed west out of the city. Carberry’s was considerably upmarket from the Starlight. This was no country hick joint, probably used by businessmen for their illicit hanky panky. The late model metallic orange Ford Ranger was parked in the lot and I drew up alongside it, my little VW dwarfed by the truck. Jed and Tom were sitting in an alcove, quite discrete as we were going to discuss affairs that wouldn’t necessarily be acceptable to anyone overhearing our conversation. They were both in their black leather gear and boots. I sat down quickly before my cock had time to react to the stimulus.

It was strange to be chatting away like we were old friends with no reference to what our potential relationship might be

Jed placed a briefcase on the table and took out a couple of A4 sheets. He handed them to me.

“Take a look through and tell us what you think.”

At first glance it appeared to be a contract. It was headed Master/slave and laid out conditions of service. My heart raced as I read it. I felt that my whole life had led up to this point. Now it seemed that I was on the brink of it becoming reality. I spent probably twenty minutes reading the terms of service. It gave Jed carte blanche to treat me in virtually any way he wished. It did say that no permanent harm would come to me but specified that punishments were entirely at the discretion of my “owner”.

“Any questions?” Asked Jed.

The obvious one was about my work. I had been made redundant a couple of months before and was pretty much living hand to mouth doing a variety of low paid jobs. I put this to my potential master.

Jed answered the question. “That isn’t really an issue. You see I had a pretty substantial inheritance a few years back. You will have all your expenses covered.”

This was quite appealing. My rent currently accounted for over  half my income. It seemed as if I might actually be better off financially with this proposed arrangement.

“Could I have twenty four hours to sort things out?”

Jed agreed to this and went on to explain.

“The guy that you saw in the cell is Anton. Tom has owned him on a contract just like this one for more than a year. We thought that it was time that I had my own slave. Of course you will be answerable to both of us. The domestic work will be split between the two of you. Apart from that you will be available for our amusement. Basically you will be a sex slave.”

There seemed little point in delaying the inevitable. I wanted this, had wanted it all my life. I picked up the pen and signed along the dotted line at the bottom of the second page. I agreed to meet Jed at the hotel at six p.m. the following evening.

I took a cab to the Carberry motel. Jed was on his own and I climbed aboard his truck. It was a half hour drive to his place. I recognised the bumpy unmade road that we had bounced along the previous night from the roughness of the ride, this time I was not naked and hogtied in the load bed. Tom was waiting for us on our arrival. The house was massive, a ranch style place. To the rear a blue and white Cessna 400 on a grass airstrip. For the first time I realised that Jed had serious money with which to indulge his hobby, of which I was about to become a part of.

We went through to a large square room furnished in a modern minimalist style, all black leather and chrome. The three of us sat down with cold drinks. Once again I found that I couldn’t take my eyes off these two guys. I was well aware that I was being cock driven but the urge was just too strong to resist.  They began talking about Saratoga. I knew that it was a place in New York State famous for trotting races. Tom came over and began examining me.

“You know I think that you have a real chance of winning with him. With some intensive training he might just do the trick.”

Jed explained. “You see it’s the alternative Derby. This one is for humans. We would like to train you up for the competition, it takes place the last week in September.”

He picked up the TV control and the screen came to life. I had never seen or imagined anything like it. Naked guys strapped to little trotting carts were racing around an oval track. The drivers seated behind them were all leathermen. They wielded long dressage whips that they used to spur their charges on to greater efforts. Several hundred spectators lined the white painted rails cheering on their favourite runner and rider combination. I thought that I had never seen such an erotic spectacle in my life.

Jed clicked off the TV. “What do you think? Are you up for that boy?

I didn’t really need to think. I imagined myself helplessly strapped to one of the sulky carts being driven to the limit to satisfy my owner. I knew then that I wanted that more than anything in the world, and I wanted to win. The training program was tough. Either Tom or Jed would be up early to release me from the steel barred cell that was my usual sleeping place. The centre cell of the three was permanently unoccupied while the far one held Anton. I had no idea what he had done to justify the treatment that was meted out to him. The punishment bondage that he was kept in was an ongoing permanent torture. The device that kept him in a world of pain was called a kneeler. A pair of steel fetters connected by a short length of chain had a metal clamp that locked in place around his scrotum. There were only two options when locked into a kneeler. You could squat in such a manner that the chain didn’t threaten to rip your balls off, the downside being the agony generated in your calfs and thighs was huge. Alternatively, you could just roll onto your side and lie there. Tom had temporarily precluded this option by fitting a steel and leather head harness with a ring on top of the skull. A chain attached and connected to another set into a beam in the ceiling above held poor Anton in a permanent squat. My sympathy for him however would soon be put into perspective as my own training program commenced.

Early the next morning the sound of Tom’s Dehner’s on the steps leading down to the dungeon announced his arrival. The look of the guy, two hundred and thirty pounds and six feet two in head-to-toe black leather gave me an instant hard on. In his gloved hand a wide leather posture collar with a heavy steel ring attachment was soon buckled tightly about my neck. He clipped on a leather leash, and I was led back up into the house. Jed awaited us in the room that we had sat chatting in the previous evening. Tom manoeuvred me into position in the centre of the room. “Stay right there boy with your legs apart”.

Taking some electric clippers Jed quickly shaved my head, all my thick blond hair soon lay strewn around where I stood. My pubic hair soon followed before I was wet shaved to a perfect smoothness. I eyed the stainless steel contraption that he now held. I had seen guys locked into chastity devices in films but never experienced one. In a matter of seconds the concentric steel bands were locked into place around my shaft with another behind my testicles. My cock now safely out of temptation’s way.

“You will stay in chastity throughout the training period. We don’t want your energy being sapped by you wanking, I will keep this safe.”

Jed slipped the little silver key that locked the device into the pocket of his leather jeans. My arms were moved behind my back and Tom fitted a single arm glove. Made of heavy grade leather it laced my arms tightly behind me. Straps bound my upper arms together above the elbows. A pair of soft black leather running shoes were laced onto my feet and Tom led me out to where the pick up stood at the rear of the house.A solid steel rod had been attached to the tow bar and the other end was fixed to my collar.

Tom looked me in the eye. “This is your training program boy. By the time we have we have finished with you the Saratoga trophy will be ours.”

They both slipped into the Ranger and the engine fired up. Jed dropped the truck into drive and it gathered speed, moving out onto a circular cinder track than ran between the house and the airstrip where the Cessna 400 was parked. The pace was easily manageable at first. After a couple of laps it became more challenging and I was panting heavily. By the time we had completed four I was nearing exhaustion. At the end of the fifth I stumbled and fell. Jed drew the truck to a halt and I was unhitched. Tom led me back into the house.

I noticed that he held a stopwatch in his hand. “Eight minutes thirty five seconds”. He announced.

Jed nodded. “Not bad. Although I think that we can improve on that, at least get it down to the eight minutes.”

He turned to me. “That was your trial to see what you might be capable of. You will run the five laps three times a day. We expect you to improve a little each time. The Saratoga tournament is at the end of next month. By then we will be expecting your times to be a lot better than today’s. Of course strapped to a sulky you will be much slower, we will do some sulky work from time to time.”

And so my training as a human pony began. Three times a day I set off around the oval cinder track. Gradually my five lap times fell towards the magic eight minutes. Tom stood beside the starting point with his stopwatch. Interspersed with these runs Jed would harness me to his little sulky cart, a steel frame with bicycle wheels and a single padded seat. My forearms were secured to the timber shafts that projected forwards, heavy leather straps binding me tightly to them. Jed in full leathers and his magnificent highly polished laced knee boots settling into the seat, the long dressage whip in his gloved hand. We would do some circuits, the thin whip encouraging me whenever my pace flagged, my cock fighting the confinement of the steel chastity lock to absolutely no avail. The nights were spent in my cell listening to the whimpers of Anton who was invariably bound by various steel devices. Occasionally Tom would unlock the door and use Anton for his pleasure before leaving him bound and hooded.

One day in late September Jed announced that we would be leaving for Saratoga some fifteen hundred miles distant. We would be taking the Cessna, the flight being some six hours in duration with one stop for refuelling. Anton and myself occupied the two rear seats. I was casually dressed in tee shirt and shorts, Anton in a black leather straitjacket and heavy leather hood, a head harness and a gag ensuring that he was totally unable to communicate. Anton was a bit of a mystery. I understood that he had signed a contract with Tom that gave the latter consent to use him in whatever way he desired. I was beginning to understand that, unlike Jed, Tom’s sadistic inclinations knew no bounds. I had on several occasions witnessed him being taken from his cell and suspended from the hoist in the centre of the dungeon, his screams echoing round the walls as he was whipped, caned or tortured in some other manner. I shuddered to consider the life that lay ahead of him.

Jed treated me well. He loved the oral sex that I gave him and I too enjoyed that aspect of our relationship. I was trained to relax my gag reflex and, apart from a little enthusiastic foreplay with one of the many whips that lined the dungeon wall my limits were never approached. The ponyplay appealed strongly. I loved the degree of helplessness that it involved.

We circled the ranch a few miles west of Saratoga Springs before touching down on the private airstrip. We were met by  Chuck Driscoll, a large Texan in his SUV. We were ferried the few hundred yards from the airstrip to the house. Behind the house stood the stable block. Divided into sixteen individual stalls where the ponies were to be housed.  The tournament was due to begin the following  day.

The next morning Jed arrived and collected me from my stall. The sulky cart stood out side and I was quickly strapped into it, my wrists secured by heavy saddle leather cuffs equipped with triple steel buckles strapped me to the wooden shafts. A leather strap head harness with attachments for the reins was soon in place. I felt my cock straining against the steel restraint that held it in confinement before me, I found the helplessness incredibly erotic. Jed had hinted that success in the tournament would bring the reward of being released and milked, something that I realised after several weeks would provide a spectacular orgasm.

As we approached the start line I glanced across at my opponent. The pony was a red headed guy who carried rather too much timber. As Chuck mounted the start rostrum, his handgun gripped and ready to fire to begin our heat I was confident. From the outset I allowed my opponent to pull ahead. Jed was clearly happy with this as the dressage whip didn’t see any action. The track wended its way through the trees shielding us from the hot September sun . The track comprised two long sections running parallel to each other. As we reached the far end my opponent was visibly tiring and, just after the turn, I overtook the other sulky and began to pull out a substantial lead. At the finish we were fifteen seconds ahead. I looked across at the red headed guy, his back and thighs were whipped raw by his rider’s whip. I didn’t envy him over the course of the coming evening. His rider didn’t look pleased. We however were now into the last eight.

I was rested during the afternoon while the other heats took place. In the evening I was once again harnessed up for the next round. This time I eyed my competitor. The guy was shaven headed just like me and quite similar in stature. I realised that this was going to be much tougher than the first heat. Sure enough our rivals went off much faster and I adopted exactly the same tactics. This time after the turn my challenge was resisted. As we both gathered speed I gradually drew level. For the first time Jed brought the whip into use, hard slashes fell across my back and shoulders, driving me on to still greater efforts. My lungs felt as if they were about to burst but over the final few metres we slowly edged ahead. We were now in the semi finals.

The following morning we were scheduled to run in the  first semi final. Our opponents looked seriously fit. The pony was a small, dark athletic looking guy. From the off they streaked ahead and, at the turn had pulled out a substantial lead. It looked as if our race was run. With two hundred metres remaining we were fifty metres behind and Jed’s frantic whipping was achieving nothing. I saw the last turn ahead, a tricky left hander. Their sulky, quite unnecessarily cut the corner and the wheel caught the protruding root of a large tree. I watched in amazement as it tipped slowly onto its side. We passed the wreckage and crossed the finishing line to the cheers of a couple of hundred assembled spectators.

The final was to be run on Saturday afternoon. Our opponents were an outfit from down south. The pony was a finely muscled black man who I guessed would be a formidable challenge. His body was oiled and gleamed in the sun as we took our places side by side on the starting grid. At the sound of the starting gun we moved off. Once again I used exactly the same tactics, allowing our opponent to take the lead. I kept their sulky well within range until the turn and then closed the gap until we were almost within touching distance of them. After negotiating the curve where our previous opponent had come unstuck I watched as the pony in front received a tirade of strokes from his driver’s whip. I could clearly see wild weals on his dark skin, a cut opened where several blows had landed on the same place. Now we were in the final stretch. Jed brought his own whip into play and the crowd went wild as both guys thrashed their mounts mercilessly in an attempt to gain an advantage. We crossed the line side by side, unable to tell who the winner was. Chuck announced that he would have to give it some consideration and that the winner would be announced at the dinner that evening.

I don’t think that I had ever seen so much black leather! All the tables were filled with the owners of the sixteen ponies as well as other invited guests. The fourteen vanquished guys were appointed waiters for the evening and dashed about serving drinks and food. Kendrick the other pony and myself had been brought up onto the stage before the dinner began. Chuck Driscoll had then appeared with what I recognised as two kneelers, one in each hand. Soon we were both locked into the devices, facing out towards the dining area.this was the first time that I had worn one of these diabolical pieces of equipment. I understood from what Jed had told me that they were Chinese law enforcement equipment, used in that country effectively to gain confessions from suspects. It was easy to understand how, even after a few minutes locked in one, that you might admit to anything you were accused of. We were placed facing so that we might watch each other’s agony as the stress as the evening progressed. We watched as the evening progressed, our groans of pain drowned out by the hubbub of the leather men’s chatter as they ate and drank.

Finally Chuck mounted the stage and unlocked us from our kneelers. He was wearing a magnificent pair of Wesco lineman boots that reached to mid thigh. He ordered us to worship his boots as he made his speech, which we did, one kissing each leg. I couldn’t fail to notice the hefty bulge at the crotch of his skin tight leather jeans. He announced that, despite a lengthy period studying the photographic evidence he had been unable to separate the two finalists and therefore we were to be declared joint winners. He handed silver trophies to both Jed and Kendrick’s owner. Both guys held their prizes aloft to rapturous applause from the assembled leather men. As he led me back to my stall Jed told me that I would receive my reward the following evening back at the ranch.