Based off the character from Pinocchio.
The coachman had started out, at first, for the money of it. You could make a pretty penny off a jackass, back when they were useful–mines, the circus, farms. What did it matter, a few children disappearing here and there? Why go asking questions about Pleasure Island off the coast, who had built it, and what it was for? It was convenient, and profitable, and so long as those two boxes were checked, the coachman was satisfied. But it wasn’t long before there just wasn’t as much gold to be had from an ass anymore. The world was changing and so he began looking for other ventures and schemes–but he soon found that things were not nearly as simple as he’d imagined.
There were the dreams, at first. Lost on the island, wandering among the attractions and bars and rides, all alone, the braying in the distance coming closer until he would wake in a cold sweat, hands flying to his ears and mouth, certain he would be changed in the night, but always normal, for now, but the dreams only grew more intense. He took the boys there on a hunch, and sure enough, with a fresh shipment of asses bound for the mainland, he slept like a baby for weeks–but the nightmares returned, and the coachman understood. The island wasn’t simply a place for profit. For all intents and purposes, it was an employer–one he would need to keep pleased, if he was going to have a happy future.
He kept up his other business for a while, but everything fell by the wayside before long. It was just him and the island, unchanging with time, never growing old, always on the hunt for stupid young men to lure across the water, and ferry back in their cages. The island seemed to consume more and more of him, in time. At times, he would catch himself wandering among the attractions, talking to it like it was a person–it never replied, but he knew what it would say, in any case.
It got harder and harder, even as the island grew hungrier and hungrier. He couldn’t keep up–he wouldn’t be able to keep up, for too much longer, not if he didn’t find a better trap. Still, he’d managed to get a few…deals going, with some of the fraternities at the colleges around the city. They would send troublesome young men his way, and in return, he’d give them a fresh mascot (if they wanted) and a sack of gold for the pleasure. Gold was easy, after all–the island could give him as much as he needed, to sweeten a deal. But he could tell, now, that he was losing himself–his humanity. Slower than most, but it was happening all the same.
With most, it was the ears first. The ears, the teeth, the laugh. But with him, it wasn’t–it was his cock and balls, much to his embarrassment. He woke up one morning, to find a sheath running up his crotch, an eight inch cock flopping out–humanish, but also…wrong. He tried to ignore it, and stepped up his recruitment efforts, but it only got worse–the fur spreading from his crotch up his belly and down his legs, the beginning of a tail pushing out above his ass. He knew he had to do something–but what? He asked the island, he begged it for an answer, but it gave him nothing.
He picked up a shipment a couple weeks later–twelve frat brothers going on a pleasure cruise around the cape, with a stop at a mystery destination for an evening of pleasure. He could hear them from the caves at the cove, the laughter turning to screaming turning to braying–and listening to it, he found his inhuman cock beginning to…harden. He tried to ignore it as best he could–any indulgence on the island was enough to tempt things along, and he still had no intention of letting go of his humanity now, not after so many centuries of this. But his cock didn’t soften, and it wasn’t long before a figure came tumbling down the steps of the cove, hobbling and lurching for the boat.
There was usually a clever one, but the coachman could deal with them easily enough. He picked up the gun and leveled it at the donkeyboy charging toward him, bringing him to a halt, and told him to turn around and go have some more fun with his friends. The young man pleaded with him, everything word a frightened bray, and looking at him, his cock was growing even harder, forming a massive, obscene tent in the front of his pants. He…knew what he wanted–what the island wanted–but was it safe?
“You wanna…you wanna be normal, boy?” the coachman said, setting the rifle aside, “I got a cure, I suppose, but you won’t like it.”
The donkeyboy nodded and scrambled for the boat, but pulled up short when the coachman undid the front of his pants, and unleashed a massive, foot long donkey cock, stiff and leaking. His eyes went wide, and the coachman laughed. “Come on boy, you wanna be normal again? A real boy? Then suck, ‘n if you do real well, I can help.”
The donkey boy shook his head, but as he retreated, his hands and feet both solidified into hooves, leaving him wobbling on his hind legs a moment before he fell forward onto all fours. What choice did he have? He trotted up onto the deck of the boat, and started sucking at the coachman’s inhuman cock. He grabbed the donkeyboy by the long ears and started fucking his throat, working the shaft in as deep as he could, and it was only a minute before he felt sweet release, gout after gout of donkey cum pouring from his balls, directly into the boy’s mouth, and as he drank, the coachman watched as the last of the boy’s human face was swallowed by fur, a snout pushing out, and he brayed in confusion and horror at himself–but before he could run, the coachman had a loop of rope tight around his neck, and hauled him down into the hold of his ship.
When the new donkey was secured, the coachman inspected himself–he was by no means back to normal, but the hair had receded slightly, and the head of his cock flared slightly less–how many loads would it take, he supposed? His balls were churning again, the distant braying of the boys on the island making him hard, and he set off from the boat. There were bound to be a few holdouts left–why not allow himself a bit of pleasure too?
Bracken's Corner 