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It was a running joke about his family all around town. And not those good jokes that make people go smile nicely and chuckle warmly. No, this was one that had people smirking and snorting as they passed any of them around town, no matter where it was. They'd ask his mother or father something like "is he one of your little asses?" and then bust into fits of guffaws in the middle of the supermarket. They raises donkeys on their farm, among other animals. Nobody cared about the other ones though as long as they got to imply that he was among the asses they raised.

Jake had heard all the jokes, some of them well crafted better than others. After years though of the same people making them, they all were on a cycle of repeats. His cynicism had both started and subsequently stopped his counting of how often each joke was made. When the same one is heard more than five times in the same day, it's not long till you give up counting. Anyways, Jake knew they were just words in jest; everyone would tell him was a good kid he was, ruffling his hair. That too ceased to irritate, as he'd learned if he protested they'd just tease more.

Now, his family did raised donkeys among other animals, but the donkeys were what people around there had more of a need for, helping to work the fields and such. People in town would call and ask to use a team and Jake and his father would bring them over, picking them up at the days end. Jake loved those days cause he could find a spare moment to himself in the barn, cleaning the stalls and usually stroking one out too as nobody else ever came in during the day. It was the only place he got some privacy.

This day was a trifle different though by comparison. His father figured with the harvest approaching soon it could be good to get some more donkeys to work the fields. They had enough room in the barn so he'd made some calls, and this was the day the new jack was being delivered. It would give them some time to get him settled in and used to the farm and jobs he'd be doing. Jake and his dad brought the donkey into the currently empty barn and set him into an unused stall, then Jake's dad left his son to his work in the barn. Jake set to work diligently, feeling the donkey's eyes on his back the whole time. It unnerved him at first since the barn was usually empty but the feeling quickly faded. In no time Jake was done, standing in the middle of the barn smiling.

He checked on the donkey one more time before moving to his favourite spot in the barn and started stripping off his clothes. Working on a farm had given him some muscle and definition; Jake was always pleased to see his hard work had been paying off. Stripping off his pants, his boxers tenting already in anticipation he swung it around in it's confinements, enjoying the feeling of the fabric on his member. Jake's boxers were quick to drop, his modest 6 inch cock springing free, eliciting a sigh from him, promptly wrapping it in his hand as he began stroking. The pleasure he was giving himself made his knees shake a bit so Jake slowly dropped to his knees, not noticing the donkeys stall door had opened up.

The jack was watching the boy with fascination, his thick cock emerging from it's sheath to drool on the barn floor. Silently it moved behind Jake, watching till the boy leaned forward, supporting himself on his hands, exposing his ass. The donkey quickly moved over top of Jake, trapping him where he was. This shocked him from his lusty dealings; he tried to squirm and move away but was trapped under the beast. He wanted to say something but feeling the donkeys drooling hard member on his back left him speechless, his erection fading from the shock. Slowly the donkey started to hump Jake's ass, sliding over his back and between his cheeks. Occasionally the flared head would brush against his hole and the donkey would bray while Jake shivered. With every pass of the donkeys head, the more of his precum lubed Jake's ass. Eventually the donkey pulled back enough to line up its cock with Jake's hole as it started to press forward, making Jake groan and his eyes bulge.

"No no no donkey you can't, you'll not fit it won't work what are you--" Jake cut off with a gasp, feeling his hole beginning to stretch open slightly. The donkey's flared tip was too big to fit in but the eye was lined up enough to set the donkey off. He started braying as his cock unleashed a torrent of donkey cum, mostly landing on the barn floor and Jake's back, but some shot into Jake's lubed ass. He shivered in disgust at the whole situation, on his hands and knees, trapped and humped by the new donkey on the farm. Once his orgasm subsided the donkey moved back and Jake shot up to his feet, running and grabbing a nearby towel. While wiping off the cum from his back he lead the donkey quickly back to his stall, securing the door. He used his towel to wipe the rest of the cum from the floor before rapidly dressing and fleeing the barn.

Once inside the house Jake threw his towel in to the hamper and jumped into the shower. He shuddered under the hot water thinking of what had happened, and almost happened. He'd almost been fucked by a donkey. He tried soaping his ass as best as he could but it was sensitive and still slick with the donkeys cum. He couldn't tell anyone, it was too humiliating. Besides, Jake thought with a slight smirk, people would just say it was incest.

When he was out of the shower and dried off Jake had resolved to forget the whole thing. A one in a million time incident. He got dressed and went to help his mother with dinner, laughing like normal. After dinner was finished Jake and his dad went around to collect the other donkeys for the day and had them back into the barn. All the chores done his family said goodnight and headed to bed.

Through the night Jake rolled around, plagued by the donkey in his head walking towards him, hard cock pointing right for him. He was trying to run but each step the donkey seemed to be closing in. While he dreamed Jake's ass started to swell in his shorts. It wasn't much, so much so it was barely noticeable. What was was his pucker started to darken and swell till it was that of a donkeys. In the dream just as the donkey caught up with him Jake's alarm rang and he sprang up, heart pounding. He did a quick look around the room just to make sure there wasn't a donkey close by, his rational brain not thinking right. Shaking his head Jake got up and dressed, noting his ass felt a little different, but pegging to getting stretched slightly yesterday. Shaking his head a second time he vowed to forget those events.

Jake fell into the normal routine after that. A hearty breakfast then off with dad to deliver the donkey teams. His dad left him in the barn to clean up while he checked on other aspects of the farm. Jake tidied the place with his usual methodical cleaning, running generally on auto pilot. When he was done he debated if he should stroke himself off today. Part of him said no, but he missed yesterday and the horny voice in his head said to just go for it. Jake did a quick check to make sure the donkey was secured in his stall then started to strip himself off, his cock springing to attention. With his back to the donkey he didn't see it use it's teeth to open the stall door with surprising quietness, much as it had the day before. The donkey was less patient today, his horniness building watching the boy's naked form. Quickly and quietly he moved behind Jake and shoved him down to the ground, who landed on his hands and knees with a muffled ooof. The donkey pressed it's muzzle against Jake's ass and gave his donkey pucker a quick lick with his thick tongue, making the boy groan softly at the sensation. The donkey then took its spot over Jake, once again trapping him under it's body.

The donkey started it's humping quickly in a steady rhythm, dragging his cock over Jake's body, smearing precum all over the boy again. Jake was once again stupified that this was happening again and thought to himself what, why me? Why is this happening twice. And with a donkey no less.

When his ass was thoroughly lubed the donkey lined up the flared head of its cock with Jake's swollen pucker and started to press forward slowly. Jake's eyes bulged and he tried in vain to scramble away from under the donkey. His hole was stretching, more than it had stretched the day before. Wider with more pressure from the donkeys huge cock. Soon the pressure was too much and the donkey's cock pushed into Jake's ass.

Jake was expecting pain. An immense agony through his whole body. He was counting on it as something to latch his mind onto. But all he felt was a jolt of pleasure through him. He moaned loudly as his once virgin ass was filled by the donkey. More and more sunk into him, boy and beast grunting with pleasure, until Jake had taken half the donkeys cock. He knew somewhere in his mind that it was impossible to take more, his body physically couldn't do it, but he wanted all of it all the same. The donkey had begun thrusting its hard cock in and out of Jake's ass, braying loudly. The donkey and Jake were both approaching climax, Jake's hard cock leaking under him, his balls churning their biggest load.

"I'm being fucked. I'm being fucked by a donkey! Uuugh a donkeeeeehaaaaaaaaaaaw!" Jake brayed as his cock shot the biggest load of his life. Spurt after spurt. Jake's orgasm was causing his ring to spasm which set the donkey off, shooting it's load deep into Jake's insides. Jake looked down at himself as he was filled up, seeing his belly swelling from all the cum. The donkey's breathing eventually slowed, as did Jake's, and it pulled itself from his ass, Jake collapsing on the ground, spent. The donkey knelt down beside Jake, curling himself protectively around the boy.