Milking a Cowboy

This is the second part of this story:
https://www.reddit.com/r/BallbustingStories/comments/1pm7qtq/family_first/?utm_source=share&utm_medium=web3x&utm_name=web3xcss&utm_term=1&utm_content=share_button

Note: some spelling is intentional for trying to mimick their country accent when speaking. If the spelling looks weird, trying sounding it out.

I arrived at the McKay ranch early. I wanted our session to start as a surprise. Conner wasn't expecting me for another 40 minutes and would be doing chores in the barn. I know this because for the past few years, I've been coming monthly to collect the McKays' loan payments. Last week, however, Conner and I came to an understanding. His family's loan would be cleared if he let me bust his family jewels for the next 10 weeks. Today starts week 1.

I'm not sure why I made this deal to be honest. His family still owed a few hundred k, and if I forgave it, it would come directly out of my pocket. My dad would kill me if he found out I made this deal. Still, I saw my chance to get my hands, and feet, on Connor, like I had wanted for years.

I didn't actually have a plan this week, just thought if I could do a surprise start, he wouldn't have a chance to brace himself for the first hit. I entered the barn when I saw him, carrying a couple buckets of water heading toward the horse corral. It may have been summer, but it wasn't so hot that he needed to go shirtless. Yet, there he was, sans shirt, the strain of the weight causing his muscles to strain. He wasn't particularly muscular, but he was well-defined. And those jeans... he had a belt to keep them up, but they say so low on the waist that his v drew the eyes low.

He walked up to the watering station and set a pail down so he could pour one bucket in; that's when I struck. The sound of ranch animals masked the sound of my own boots (I wore steel toed today on purpose). As he bent forward to lift the other bucket, I rocketed my boot forward, aiming for the bulge in the crotch of his jeans.

His body lifted from the force of my kick, though I was quite disappointed that the jeans masked the sound of his meat getting pulverized. I didn't quite expect him to drop like that. He didn't even move. I kneeled next to him to see his face, though his hands reaching into his jeans to directly hold his balls. He appeared completely out of it, except for heavy breathing. For a few seconds, I watched his chest and stomach expand aggressively as he sucked in deep breaths, then he started coughing deeply.

His blue eyes finally caught a hold of mine as he tried to compose himself.

"You sunovabitch" he coughed, before rolling onto this side and onto his hands and knees. He spat.

I would never let a good opportunity go to waste. I stood up and stood behind him, but he was too busy coughing again to notice. It was perfect. I shot my boot between his legs, aiming just below his ass and rearranged his nuts. He plopped forward onto the ground, writhing and groaning.

My pants were wet from my own leaking, seeing him busted like this. It was a dream come true! I enjoyed the sight for a few minutes as he came back around. He was panting as he dusted off his cowboy hat and struggled to get to his feet, as he knees shook.

"No more. I cayn't," he whispered as he leaned against the horse pen. Thanks to my post-nute clarity, I tried to be tactical.

"We 'greed ten weeks, Conner, an' this session ain't over yet."

"No. No. No. No. No," he said flatly, appearing to console himself. He still had one hand holding his groin from underneath, like he was keeping his balls from falling.

"I tell you what, McKay. Let's make a deal."

"No, no more deals."

"Jus' hear me out. I think you actshly enjoy this." I knew it was a stretch, if not ragebaiting. He met my eyes in disbelief as if I had forgotten I had just polished his testicles with my steel-toed boot.

"No really. I bet you'd cum from bustin' alone. That's how much you like it." He was stunned silent, knowing the wager was coming.

"If you cum from me bustin' you, then you spend each of the remaining sessions in just yer birthday suit," I was grinning from ear to ear just thinking about it. "But if'n ya don't, then no more sessions and yer debt is paid."

He was quiet for a moment, weighing the impossible options. He already didn't want his balls busted, let alone being naked for it, but he couldn't just give up the opportunity to free his family from the loan.

"Shit, Kyle. Sure. Why not? I ain't into this like you anyhow."

I tried to sound offended but couldn't contain my joy.

"We'll see, McKay. Spread 'em."

He sighed and stepped forward, shaking his head in denial. I, on the other hand, was risking 9 more sessions if i couldn't make cum! I needed to do some rapid fire shots or he'd waste too much precious time groaning and rolling around.

He didn't expect it, but I grabbed his shoulders and push him back against the pen wall and pinned his arms back. Before he could protest, I drove my right knee up into the McKay family jewels and followed it up with quick succession. I wasn't counting, but I think that was about a half dozen before my leg couldn't drive up with full force. That last knee was more of a straight push instead of pounding up into him.

It was a chore to hold back this cowboy as his body folded forward into me, so I dropped low and buried my shoulder into his stomach, perhaps too forcefully. He crumpled forward to lean on my back with an obligatory "ooomph!", and I beging driving my fist up to mash his berries, using my shoulder muscles as leverage. Since he was off balance, he couldn't force himself to go in any direction, which allowed me to go to town on it, though even my shoulder grew weary and my knuckles became angry at connecting with denim and his pubic bone. I needed to end this before I was too tired.

From my position, I reached up and unbuckled his belt and undid his jeans. From there, I yanked his jeans down, and I was lucky enough to have grabbed his boxer briefs at the same time. His cock was soft and uncut, but it laid across a couple of swollen balls, red and angry. I reached up and squeezed. Now, I'm a man of my word; I wouldn't win this bet by cheatin' and touchin' his cock. However, I couldn't hold both nuts in one hand because of the swelling, so I used both hands.

By now, he was using his hands to try to reclaim his manhood from me, but I couldn't let him stop me and risk losing the bet. If he stayed standing, he might be able to use his hands on my head! So I yanked down hard, which brought his body crashing down, his cowboy had fell off and bounced off my back as he rolled to the side. I forced him onto his back by directing him from his testicles and positioned myself between his legs, on top of his pulled down jeans to keep him tethered down.

For a brief moment, I caught his blue eyes looking my way, but they closed tight when I started squeezing. If I'm being honest, I didn't know what to expect, but after about 10 seconds, his cock started bobbing up and down before exploding all over his abs and up to his chest. It must have done this for around 20 seconds before it stopped and I let go.

We were both panting for different reasons, but I sat there between his legs to watch him holding his nuts until he finally calmed down enough to raise his head and look at me with defeat.

I stood up and looked down at him, having conquered his manhood.

"Next Sat'a'day, don't forget. No clothes."

Then I headed back to my truck.