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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.
The guys slept through the night. Despite erections poking back and forth as they rolled around in the bed, neither of them were woken up. But the sun came up early Saturday morning and that woke them up. Though neither said anything, they were both amazed by their morning wood.
Jake jumped out of bed and said they had a big day planned but it was a surprise. He told Kole to get in the shower and appropriate clothing for the day would be ready when he was done. Kole showered and returned to find a t-shirt, long sleeved shirt, a worn pair of jeans and his black cowboy boots laid out. He dressed and headed downstairs. Within a few minutes, Jake appeared wearing similar clothes. Jake's boots were more traditional cowboy boots, not as fancy as he normally wore.
They ate breakfast and they were soon on the road. Jake wasn't saying anything about what was planned. At the base of the mountain, Jake pulled into a farm and Kole saw the signs offering trail rides. Kole was touched. It was obvious Jake had understood how much he liked horseback riding and had taken it upon himself to try and cheer up his new friend.
Kole quickly explained to the person in charge that he was a fairly experienced horseman but hadn't been on a horse in a couple years. He quietly mentioned he wasn't sure his friend had spent much if any time on a horse.
The cool morning air was refreshing. The horse was great. Kole was having a great time. It looked like Jake wasn't doing bad either. By then end of the ride, the day had warmed up nicely. Kole stripped of his long sleeve shirt to just the sleeveless shirt Jake had set out for him.
After they turned in the horses, Kole was grinning from ear to ear. He thanked Jake and asked him how his ride was. Jake said "To be honest, I've never spent much time on a horse, but this horse was easy to ride. And, I'm sure you'll be happy to learn that my underwear seemed to go deeper up my ass with every bounce of the horse. So I've had a two-hour wedgie going on!". Kole couldn't help but laugh a little.
They stopped for tacos on the way back to the cabin. During the meal, Jake mentioned how natural Kole looked on the horse. "Did you ever have to work as a cowboy on your farm?" Jake asked. Kole admitted he really didn't. The cows were fenced and it was rare one got out and had to be chased. But Kole had spent a little time goofing around in the Junior Rodeo when he was 10 years old. But everyone else already had more experience and, even as a kid, the farm had kept him busy. Jake still thought that must have been some fun. Kole conceded it was fun, but also a lot of work. Jake joked "Maybe we'll have a rodeo someday." But Kole wasn't sure what he meant by that.
By then, the day was warming up and they headed back to the cabin for a little relaxation. The two riders, still dressed in their horse riding attire, sat in a couple lounge chairs on the cabin deck, enjoying a couple of beers and talking. Jake admitted to being a bit of a jock, maybe not a great one, but he dabbled in football, baseball and wrestling. However, he certainly wasn't going to mention to Kole wrestling was just too erotic for him to continue the sport past the first year.
Since Jake had asked Kole to someday demonstrate rodeo skills, Kole asked Jake to show him some wrestling moves. Jake was more than willing to do so. Jake explained "First we stand and face each other, square on. We lean in and when the referee signals, we start." Kole said "I'm the referee, let's go!". For a brief moment, they looked like a true pair of wrestlers circling each other, looking to make a move as their boots stomped on the deck. That was the last moment Kole had any chance of looking like a wrestler. Before he knew it, Jake was on him and had him thrown to the ground face up and was towering over him. Kole squirmed and moved around but it seems every move he made, Jake was one step ahead. Kole went from face up to face down, sometimes any movement was difficult. Sometimes, he though Jake let him lose just to grab him again. Kole's big mistake came when Jake let him up and Kole made it up on all fours and was just trying to stand up before Jake pounced on him again. Before he knew it, Kole's head was pinned under Jake's crotch, just as Kole was standing up, which left Kole's ass raised in the air. Oh the view Jake had, The ragged shirt had pulled up exposing, once again, Kole's Fruit of the Loom underwear band. Jake took his hands and grabbed the underwear and pulled. Kole tried to fight back, but there was little he could do in the position he found himself. "Say `uncle'" Jake demanded. Kole was stubborn and tried to hold out. Jake pulled with both hands. Soon the underwear was pulled up enough that Jake could grab the leg holes. Eventually the pain of the underwear both flossing his ass and smashing his balls was too much so he mumbled "uncle" just as he felt his underwear start to rip. And rip it did. This time it had ripped clear through before Jake had let go.
Jake let him up. Kole said "You told me I didn't need any extra underwear!" Kole had secretly brought a few extra pair just in case, though. "I think you need to make it up to me again, just like last time." But Jake said, "No I won fair and square. Maybe we'll make it up sometime later.
Jake said it was time to shower and get into their nicer clothes because they were going to dinner at the clubhouse. The cabin was part of a community with a nice clubhouse and other amenities. But all Jake was concerned about was the fantastic steaks the clubhouse offered. Kole protested that he couldn't afford such a meal. Jake said his family paid the bill, so the vehicle purchases at the dealership over the years should cover it.
Soon they were off to dinner. Kole was in his black jeans, his good black Justin cowboy boots, and a shirt that was somewhere between a dress shirt and a western rodeo shirt. Jake's wardrobe was a pair of khakis, his Lucchese boots, and a blue dress shirt. They were a handsome couple. Once seated, Jake explained the idea of pairing wine and steak and promptly ordered a bottle, Kole didn't know anything about wine, but admitted it tasted great with the meal.