Don't forget to donate to at https://donate.nifty.org/
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.
Kole considered asking for a coin toss again. But he wasn't sure he'd be lucky with a coin toss either. Kole was determined he wasn't going to get wedgied twice in one day. The only way to avoid that was to win the wrestling match quickly. Kole had been studying how Jake took him down last time and as the lined up and circled each other, their boots stomping on the floor, Kole lowered his head and charged into Jake's stomach. Jake wasn't prepared for an attack like that and went down easily. Kole was soon on top of the temporarily weakened Jake and proclaimed victory. Jake acquiesced., partly because Kole had taken him down quite unexpectedly and partly because he longed to be the one punished.
"Take off your shirt and pants, so you're wearing nothing but your underwear and boots! Then stay right there." Kole commanded. "Yes, Sir!" was the response.
Kole returned and saw Jake was wearing a pair of black Jockey boxer briefs. That would work nicely for what Kole had in store. Kole rolled Jake on his stomach. Jake's hands were quickly tied behind his back. Another rope soon secured Jake's black cowboy boots. A third rope and Jake was hogtied. Kole sat on the floor in front of Jake and put one his cowboy boots in Jake's face. "Lick it!" was the command. Jake barely had time to blurt out "Yes, Sir" before Kole's black Justin boot was forced into his mouth. Jake loved the smell and taste of the leather. Kole had told him he didn't wear his black boots much (they were his "fancy" boots and he didn't attend anything fancy recently until he met Jake) so they weren't as smelly as Kole's work boots.
Then Jake heard, "Time to switch. Here's the other boot!"
After his boots were properly worshiped, Kole got up and removed the hogtie rope from his captive. He then untied Jake's hands but did not untie his booted ankles. "Hop over and sit in that chair." Kole demanded. "Yes, Sir" and Jake started hopping. Once Jake was in the chair, Kole tied each of Jake's wrists to a chair arm. Kole then untied Jake's feet and soon each booted foot was tied to a chair leg. This gave Kole a little better access to Jake's crotch.
Kole then blindfolded his captive cowboy. "We're gonna play a guessing game. I hope you get the answers right, otherwise you will be punished."
For the first thing to guess, Kole returned with one of his Ariat brown work cowboy boots. He held the boot over Jake's mouth and nose and forced his captive to take a deep breath of the well-worn boot's smell. "What's that smell?" Kole asked. Jake, his voice muffled by the boot said "One of your work boots Sir." Jake was catching on!
Next, Kole told Jake to open his mount and inserted a saltine cracker. "What did I just feed you?" "A cracker, Sir."
Kole returned with Jake's underwear from earlier in the day. He forced the underwear in Jake's face. "What's this smell?" Jake responded, "I think it's a pair of used underwear, Sir." Kole responded "Whose?" "Mine Sir".
Kole then returned with three glasses. He held the first to his captive's lips. When asked, the captive replied "Bourbon, Sir." Kole replied, "That's too easy. Which one?" The reply was Marker's Mark, Sir?" It was more of a question than a firm answer. And it was wrong. "Incorrect. I'm not going to tell you the answer was you may have to guess again."
Kole pulled out the front of Jake's underwear and dropped an ice cube in. It quickly found its way to Jake's left nut. "Fuck my nut is freezing!" Jake gasped. Kole asked which and Jake screamed "My left nut, Sir!"
Next Kole held another boot over Jake's face. "It's a new boot, I think one of the Tony Lama tall boots we just bought for riding Sir." Said Jake. "Correct but which one?" Kole asked. Jake guessed "Left, sir?" Kole replied that was incorrect and another ice cube was dropped, this time Kole made sure it went to Jake's right nut.
Next another glass was put to Jake's lips for him to taste. Jake took a sip and screamed "Holy fuck! That tastes like piss!" Kole responded, "That is correct, but you forgot to say `Sir'. Kole put a handful of ice cubes down the front of Jake's underwear. Jake gulped out "Sorry, Sir."
"Let's try to identify the bourbon again" Kole suggested. Another guess, another wrong answer. This time a clothes pin went on one of Jake's nipples. He squirmed and the ice in his crotch settled in deeper.
Kole then put one of his old stinky boots over Jake's face again. After a good long whiff, Jake again identified the boot but guessed the wrong foot on the follow up question. So a clothes pin was applied to the other nipple. Either Jake was a really bad guess on left/right boots or Kole was deliberately punishing his captive.
Kole opened a beer and asked his captive to identify it. Jake was sure there was only one kind of beer in the house and made his guess. "Incorrect!" was the response. Jake was now sure Kole was messing with him, but what could he do? He was securely bound to the chair. Kole walked behind his captive cowboy and dropped a few ice cubes down the back of Jake's underwear.
Judging from the wet spots on Jake's underwear, some of the ice was melting. Jake was taking his punishment fairly well, but Kole loved to watch Jake squirm. And when Jake squirmed, the ice shifted and the clothes pins bit a little more.
Just for fun, Kole flicked a clothes pin. His captive screamed and shifted on the chair. By now, Jake's entire crotch and ass had to be filled with ice. Just to make him squirm a bit more, Kole tickled his captive which made Jake squirm. Kole watched the clothes pins bounce up and down tormenting his captive more.
Kole then removed the ropes biding his captive's feet to the chair and then tied the two booted feet together. Then Kole untied Jake's hands from the chair arms and retired them in front of Jake. Kole commanded Jake to get up and lay on his side on the floor. "Yes, Sir!" his captive said.
Kole then laid beside his bound cowboy captive. Kole pulled down Jake's underwear. Much of the ice had melted but there was still a good amount left. Kole threw the ice cubes in the sink and returned to his captive. With little foreplay, Kole lubed his cock and Jake's ass and plunged his cock into Jake's waiting ass. "Man, your ass is cold tonight!" Kole exclaimed. "Sorry, Sir!" came the response.
Kole figured the faster way to warm up Jake's ass was to fuck it long and hard. So he did. As Kole was pumping away on Jake's ass, he heard one of the clothes pins snap and go flying "Son of a bitch, that hurt!" Jake screamed, then he blurted out "I'm cumming!" Kole felt Jake's ass involuntarily clenching his cock as Jake's load was shot. Kole pulled out and shot his load onto Jake.
Kole then placed his hand over Jake's mouth and removed the last clothespin. Kole enjoyed the muffled sounds coming from Jake.
Kole told his captive that his poor performance on the guessing game meant he was going to sleep tied up on the floor unless he could get himself loose. Kole brought down a pillow for Jake and a blanket. Kole helped Jake pull up his cold, wet underwear before covering Jake with the blanket. As Jake made himself as comfortable as he could, Kole snuggled in beside him and that was nice. Jake struggled with the ropes binding his hands but couldn't make any progress. He knew he'd never get his boots untied either, so he decided to make the best of it and enjoy Kole snuggled against him. Kole was still fully clothed and already asleep.
Jake was awakened a couple of times during the night. The first was when Kole reached over and tweaked one of Jake's still tender nipples. "Fuck, why can't I move?" Jake thought, then remember he was still tied up, both his hands and his booted ankles. Later Jake awoke to feel Kole tugging on Jake's underwear. Jake still managed to get some sleep despite the fact he was tied up, had tender nipples, and now a wedgie. Kole remained on the floor under the cover with Jake sharing the same pillow until morning.
Jake awoke with a jolt the next morning. He quickly realized he was still tied up and Kole was playing with his cock. As Kole noticed Jake was now awake, Kole said "I guess my captive cowboy didn't get loose last night. I'm still horny as hell and you aren't going anywhere." With that, Kole grabbed the bottle of lube and fucked Jake again.