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Disclaimer: This is a fictional story set in a fictional location. It's an on-going story of two young men, a farmer's boy and a bully, as their relationship develops.
Saturday morning the guys got up to go look at tractors. A local tractor dealer was going to make them a good deal because Jake's Dad made the tractor guy a good deal on a new truck. So the guys dressed in their Ariat work boots, jeans, and T shirts. On the way there, Jake noticed that Kole was squirming a bit as he sat in the truck. "Something wrong with your ass, cowboy?" Jake asked. "Yes, you fucked my ass hole raw last night like a wild man, my ass is full of your cum, and my ass crack is raw from the painful wedgie you inflicted on me. All while I was tied up and helpless to resist you!"
The guys were going to buy a tractor plus a front-end loader and a brush hog. Jake nodded as he only had vague ideas of what they were looking for. He knew the car business and the options there, not the tractor business. Since Kyle no longer had a mortgage and Kole no longer had apartment rent, they could get something decent. Plus they had the profits from Jake's townhouse though some of it was going to be used to renovate the farm house. Kyle had picked out a capable tractor, large enough to mow and do the other field work they needed, but not so terribly expensive.
The dealer guy pointed out a nice lightly used tractor like Kole was interested in, with several implements including the front loader and brush hog. It also had a sickle bar mower and a wood splitter. The guy said the best deal would be the whole setup. Kole inspected and tested everything and agreed. Jake watch Kole climb on and over everything inspecting it. He also noticed that, as was often the case, the band of Kole's white Fruit of the Loom briefs could be seen as Kole reached and stretched and his shirt was lifted up. Jake also thought Kole was still walking a little funny after the good fucking last light. Or maybe it was just from the raw ass crack. Whatever the reason, it amused Jake.
The guys headed inside to complete the paperwork and Kole said he needed to stop by the restroom. Jake agreed it was a good idea. As Kole was washing his hands after pissing, Jake came up behind him and grabbed Kole's briefs and wedgied him, tugging Kole's underwear up his still sore ass crack. Jake said, "Now march out there and sign the paperwork. You aren't going to pull your underwear out of your ass crack. Understood, farm boy?" Kole replied "Yes Sir!"
Kole was self-conscious and sure he was walking funny from the wedgie as they went to the sales office to finish the paperwork. And of course, his dick was hard. He bet Jake's was too.
They sat in the office and started the paperwork. Jake watched as each time Kole leaned forward to look at or sign something, Kole's t shirt would ride up and Jake could see Kole's underwear now bunched up above his jeans from the wedgie. This just make Jake even harder. And Kole squirmed because his ass was still sore from yesterday's extreme wedgie and ass fucking.
The paperwork was done. The tractor would be delivered to the farm later that day. Kole excused himself to use the restroom again, alone, on the way out to pick the wedgie out of his sore ass.
Jake was waiting for him in the truck with a silly grin on his face. Kole opened the door and climbed in saying "You son of a bitch! What if someone saw my underwear hanging out and knew I was walking around in there with a wedgie!"
Jake said "Yes, that's why it was so damn hot! Watching my farm boy's boots stomping across the showroom floor inside knowing his underwear was wedgied up his ass. Seeing your underwear each time you leaned forward. And it sure looked like you enjoyed it too, given the bulge in the front of your jeans."
Kole knew that Jake had him figured out. Yes, he was mad, but he was aroused. Betrayed by his own dick! "That's what I hate about you. And what I love about you. You're kinky and you've got me figured out." Kole said, "And I'll have my revenge!"
Jake said "We've got some time before the tractor is delivered. We need to get my farm boy some new clothes for his new job on Monday. Sorry, my handsome farm boy will have to dress up a bit."
The new work clothes were really just tan khakis for Kole. Like Jake, he'd be wearing a black polo shirt with the dealer name on it.
Kole looked at the piles of khakis. Pleated or not. Cuffed or not. Jake said "Just keep it simple. No pleats. No Cuffs. Let's try 32x34 size." With that Jake handed Kohl a pair of khakis and pointed him to the dressing room.
Kole came back out wearing new khakis and his old boots. The pants were just a bit too short, so Jake said try these 32x36." When Kole stepped out with those, Jake said "Perfect. Now let's get you a few pair of these and then head to the boot store. You definitely need new boots to wear with these. Unless you want to get some new, fancier underwear. But I suspect you love having your tighty whities yanked up your ass crack."
Kole changed back into his jeans so they could check out and they headed to the farm store to buy some new boots. Kole had protested that he liked his old Ariat boots. Jake had said they were fine for working around the farm, but they were too beat up for the new job. "Plus they smell horrible" Jake added. Kole replied "Yes, but I know that nasty smell came from years working on the farm and it turns you on, you pervert."
Kole looked around and quickly spotted a new pair of his old faithful work boots -- Ariats with a square toe, brown foot, and ivory shaft in a 10.5 D. Looking at the new boots and his old ones, Kole realized how much he and his old boots had been through. Farm work, his brief college attendance, the loss of the farm, lugging groceries around, meeting Jake, falling in love with Jake. The old boots would still be perfect for their new farm, but the new version of the same boots would be great for the new job.
Kole tried on the new boots. A perfect fit, just like his old ones. Jake wanted Kole to get pointed toe cowboy boots instead, but Jake was adamant he wanted square toed cowboy boots for his work boots. This way they wouldn't be too much like twins. Though they would be wearing the same polo shirts and khakis, Jake would have his black, pointed toe cowboy boots to match his black hair while Kole's boots were brown with square toes, complimenting his dirty blond hair.
Once they checked out, Kole decided to start wearing his new boots to get them broken in for Monday. He stood beside the truck and swapped to his new boots. As he reached down to gather up his old boots and the box, Jake took the opportunity to grab Kole's underwear and give him yet another wedgie.
"You son of a bitch!" Kole exclaimed, "My ass is still raw from the earlier wedgies.". Kole threw the old boots and packaging in the back seat of the truck. Then he reached behind the rear seat and grabbed an old piece of bailing twine that had been there forever. Kole commanded Jake to turn around and put his hands behind his back. Kole made quick work of tying Jake's hands with the twine. The twine was rough, unlike the ropes they'd used before. Once Jake's wrists were secured, Kole walked him to the passenger side of the truck. Before opening the door for Jake, Kole reached down the front of Jake's pants and grabbed his underwear. Kole tugged and Jake now had a melvin (wedgie in the front). Then Kole reached in the back of Jake's pants and gave him a regular wedgie. This combination squashed Jake's nut and pulled his underwear far up his crack. Jake then opened the door and commanded Jake to get inside. Kole then fastened the seat belt across his captive. Only then did Kole stop to pull his underwear out of his ass. "You're riding home like that, and I'm not going to let you loose when we get home. Someone needs to teach you a lesson and it's going to be me! You've done gotten on my last nerve." Kole said, while noticing both he and Jake had raging hard ons.