Even though Casey was still only the deputy of Copperbrook, he slept in the sheriff’s bedroom on the second floor of the police building. Considering how the bed would barely fit her big toe, Annabelle was more than okay with giving it up. Instead, she’d opted to sleep behind the building, right behind the jailhouse. It took a minute for him to fall asleep that night, as he—and a good portion of Copperbrook—discovered the new sheriff was a loud snorer. With him being the closest to her slumbering body, Casey was stuck waiting for exhaustion to force him to sleep as the walls rumbled like a freight train was just outside. 

Casey was awoken from his slumber the next morning by the shattering of glass. Jumping out of bed and expecting a break in, he was surprised to see a passive finger just outside his window. A moment later, it hid from view followed by a rumbling, “Sorry.” 

Rolling his eyes, Casey walked over to the shattered window and leaned out. 

“Annie. I told you not to knock! If you need me up, you just need to say ‘Casey’ and I’ll be up!” 

“Right, right. I’m sorry.”

Even though he couldn’t see her, Casey knew she felt bad for breaking the window. Still, considering how she’d shattered half of the windows on Main Street the day before, he was hoping she would’ve known to be more careful. 

“Anyway, what’s up?” 

His view of the town was suddenly replaced by her enormous blue eye.

“Let’s go take a morning walk around town!” 

“Annie,” Casey began, “You don’t need to do that. I appreciate your eager attitude, but it’s really not necessary.”

Annie’s eye was replaced by her mouth, “Well, I still think we should check out the town. Never know where trouble could be!” 

“I guess. But seriously, there’s almost never any trouble in Copperbrook. You’ve only been here for less than a day! At the very least, no outlaws will dare ride into town now!” 

“Yeah, but, uh…” Annie trailed off, sending her morning breath right into his face, “But we should still check out the town. Can’t be too careful.” 

Casey sighed, grabbing his uniform from its hanger, “Okay. I’ll be out in a second.”

Despite Annabelle insisting she was there to help, and the population of Copperbrook overwhelmingly accepting her services, Casey still felt a bit uneasy walking beside her. Perhaps it was due to how she could crush a locomotive beneath her foot if she wasn’t careful. Or maybe the image of her pointing a revolver with a barrel wider than his head straight at his body was still ingrained in his mind. Glancing up the massive sheriff, he decided that he might as well get to know her, considering she was technically his boss now. 

“So, uh, Annie?” He began. 

“That’s my name, darlin’! What’s up?” She asked, squatting down to bring herself closer to his level. 

Despite significantly lowering the height difference between them, Casey still had to crane his head back all the way to look her in the eye, “So, where are you from? How are you so big? How big, exactly, are you?” 

“Slow down there, hun!” She chuckled, “I’m from Texas, for starters. And I’m three hundred and five feet tall!” 

“Three hundred…” Casey trailed off, failing to imagine many things that were on her same scale, “But what about how you got so big? How’s that possible?” 

“Everything’s bigger in Texas, sweetheart!” She winked, rising to her full height once again, “Your legs must be burnin’ after all this walkin’ around! And we’ve still got quite a ways to go!” 

“I’ll be fine,” Casey insisted, not wishing to be placed hundreds of feet up into the air by a giant woman who’d clearly demonstrated already that delicacy was not her forte. 

Their walk around Copperbrook was as uneventful as Casey thought it would be. Annie kept a sharp eye out for any trouble, but trouble was nowhere to be found. By the time they’d made it to the ranch, Casey was tired and it was clear Annie wasn’t too excited about not having stopped any crimes. Leaning against a fence containing the huge herd of cattle that had been brought in about a month prior, Casey heard something hit the ground beside him. Turning towards the sound, a massive water drop crashed down in front of him, sending a few unfortunate stray droplets right into his open mouth. The foul, salty taste immediately assaulted his tongue and sent him coughing and hacking, looking up at the massive sheriff standing beside him. 

Annie had taken her hat off and was fanning herself, taking special care to get cooler air around her cleavage. Her exposed, soft midriff glistened with a thin layer of sweat in the early morning sun. With her free hand, Annie wiped away the sweat on her brow and sent a cascade of sweat drops the size of buckets crashing down around Casey. 

“Hey! Annabelle! Watch where you’re sweating!” He shouted, grabbing his canteen to wash away the foul taste in his mouth. 

Annie looked down and realized where her discarded perspiration was landing, “Oh! I’m so sorry, Case! Man, I need some water to cool myself off right about now! I’ll be right back, Imma go check around to see if there’s anything.” 

There was a horrible crash as her boot came down upon the fence, causing the wood to snap like toothpicks. Realizing she’d forgotten about the fence at her feet, Annie tried to move out of the way to avoid causing further damage. Unfortunately, her feet crashed into one another, sending her off balance. Unable to control herself, Annie stumbled through even more fences before finally passing the point of no return. With a heavy crash that shook the ground, Annie landed flat on her butt, sending the cattle herd into a stampede. Forcing their way through the broken fence, they took off and fled town. 

“Damn,” Annie muttered, “Guess those fences are weaker than I thought.” 

While the sheriff slowly stood back up, Casey would only watch as the massive herd of cattle seemed determined to run all the way to the California coast. It would take at least half a dozen men to get them back safe and sound, and even then it would take the whole day. 

“Do I have something on my butt?” Annie asked, presenting her denim-clad rear and the remains of a wagon stuck to her right buttcheek. 

Casey sighed, “Go get as many ranchers as you can and tell them to get on their horses and chase after the cattle. If we hurry, we can—”

“I’ll get them! Just wait here and fix the fence!” Annie declared before dashing off in pursuit of the herd. 

After only a few long strides, the final pieces of wagon stuck to her jean shorts fell free, smashing against the ground. Looking at the damage he’d now need to fix, Casey decided to get to work before Annie returned. Whether or not the sheriff would be successful at wrangling the cattle was another question altogether. 

Deciding that it was best to patch up the fence in the event she succeeded, Casey went to work. Using the planks he could salvage and some more from the crushed wagon, he was able to quickly patch up the broken sections of fence. With the job done, Casey turned his attention to the distant figure of Annie running around like a headless chicken and chasing after what he could only assume were the cattle at her feet. After a minute or so, she walked back over to the ranch with a clearly sour demeanor. Bending down, she deposited only two of the escaped cattle back into their pen. 

“I know what you’re gonna say, and yes, it’s not as easy as I thought it was gonna be. Hop on, we can work on herdin’ up the cattle together,” She said, extending out her enormous palm. 

“I think I’ll pass. Just let me grab my horse and I can work on cleaning up this mess.” 

“But it’ll just be easier if you come with me now,” Annie shrugged, pinching the tiny deputy between her fingers and lifting him up. 

Casey’s cries to be put down fell upon deaf ears as Annie simply ignored him, jogging back to where she’d left the cattle herd. They weren’t running anymore, but they were spread out all over the place. Coming to a stop, the sheriff raised her little deputy up to her eyes, brushing away a stray lock of her blonde hair. 

“Okay, now what should I do?” 

“Let me think…” Casey trailed off, “First, you need to round them all up.” 

“I know that,” Annie huffed, “How do I do it?” 

“For a start, you could use those huge feet of yours to start getting them into a group.”

“Like…this?” The sheriff asked, taking a cautious step towards a group of cattle. The massive form of her boot, coupled with the sound of it landing on the ground, encouraged the cattle to turn and begin making their way back towards the rest of the herd. Sidestepping to the right, she got another group to behave in a similar manner. Walking in a semicircle, she began to get the herd back together and moving slowly back towards the ranch. 

“Okay!” Casey cheered, “Now all you need to do is keep this up and soon they’ll all be back at the-” 

“I’ll just pick ‘em up! But I do need to keep you somewhere else then…” Annie trailed off, tapping her chin thoughtfully. 

Grinning as an idea popped into her head, the giant sheriff brought Casey towards her chest. Realizing what her intention was, Casey tried to struggle free. Unfortunately, there was no fighting against her hand. Tucking him safely between her breasts, Annie giggled as she felt him struggling around. 

“Stop squirming, Case! Don’t wanna fall in!” She purred, patting her little deputy on his head and causing him to sink up to his chest in her soft flesh, “Now, to get all these cattle…” 

Squatting down, Annie gently scooped up a large portion of the herd in her hands. About forty or so of the very confused cattle were lifted up as she carefully began making her way back to the ranch. Depositing the very confused animals back where they belonged, Annabelle dusted off her hands triumphantly before turning her attention to the rest of the herd. Jogging back, she had an extra pep in her step, causing her to bounce up and down more with each step. 

Meanwhile, Casey was finding himself in an increasingly more troublesome situation. Annie’s sweat was turning her skin slick, and the bouncing of her breasts wasn’t helping. With every step, he felt himself slipping further and further into her cleavage. His attempts to get the sheriff’s attention went ignored, and his struggles only succeeded in making him sink faster. It was like he was trapped in a pool of quicksand during an earthquake. 

“Annie! I’m slipping! Hel-” He cried.

With a final bounce of the sheriff's cleavage, Casey slipped. Everything went dark as the temperature skyrocketed between her enormous breasts and the poor deputy was squeezed on all sides. 

——

“M’kay, I think I’ve got the hang of this now,” Annie said to herself, using her boots to round up the remaining cattle. Once they were tightly bunched up like a school of sardines, she bent down and grabbed another armload of cattle. She was surprised how calm they were, only making the occasional ‘moo’ out of confusion more than anything else. Glancing back at the remaining cattle, Annie figured she only needed one more trip before they were all back in place. 

Casey had finally stopped whining, but still insisted on giving the occasional struggle. Dropping off the cattle in her hands, she stood up and glanced down to check on her little deputy. To her surprise, he was gone. 

“So that’s why you stopped complaining,” Annabelle smirked, “I think I’ll leave you in there until I’m done roundin’ up these cattle.”

Knowing her little companion couldn’t hear her, the sheriff walked back to the remaining cattle to finish up the job. Deciding to see Casey’s reaction to her jumping, Annie was rewarded by a good amount of squirming between her breasts. 

Collecting the last of the cattle proved to be a breeze for Annie. With the last of them back at the ranch, all that was left was for her to release Casey from his soft prison. Part of her wanted to dig the little deputy out from her cleavage and show him how she’d managed to fix the problem, but another part wanted to keep him in there until she was finished with her patrol around the town. Deciding that he could breathe in between her breasts just fine, she decided to finish up her patrol without having someone yelling at her to be careful. 

Like Casey had told her, there was no crime to be stopped on her patrol. Circling back to the police station, Annie’s feet were dying for some relief. Looking for a spot to sit, her eyes fell upon the jailhouse. Casey had lectured her about being careful around the town’s buildings, but she was confident that the jail was strong enough to support her weight. Besides, it would only be for a few minutes. 

The jailhouse was built onto the back of the police station. Made from bricks and iron, it was significantly stronger than any of the other buildings in Copperbrook. The only thing that might’ve been stronger was the bank’s vault. Knowing that Casey would only get mad and tell her not to sit on the jail, she decided to let him out once she’d rested up. Carefully squatting down, Annie felt relieved as the roof held her weight. There were a few groans from the structure, but it held her weight just fine. 

“This thing’s only good for a chair anyways,” She muttered, “And a small one at that. No bad guys to lock up, it’s just wasted space. I know! I’ll make this my personal seat in town! I get a nice view over ev-”

With a loud crack, the jailhouse gave way beneath the titanic sheriff’s rear. The bricks simply crumbled to pieces as the metal supports bent like chicken wire. With a loud crash that rocked half the town, Annie felt her face turn red as a tomato as she looked down at the pile of rubble beneath her butt that used to be the town’s jail. 

——

Casey had lost track of time trapped between the sheriff’s breasts. Finally, her enormous fingers fished him out, revealing him to the sun and allowing him to finally take a full breath now that he wasn’t being smothered by her soft, enveloping skin. Still, as much as he hated being trapped there, part of him couldn’t deny that being squeezed in her cleavage was fun. Looking up at Sheriff Annabelle, he quickly caught on that she’d done something she wasn’t proud of. 

“What did you do?” He demanded. 

“Well…” Annie trailed off, “I finished up the patrol, everything went great, and now I’ve decided to sit down and take a break!” 

“Why do you look like you’ve broken something?” 

“I mean, I did just have a teensy tiny lil’ ol’ accident when sitting down. I mighta’ misjudged how much weight the jail could hold, that’s all.” 

“You sat on it?” Casey yelled, “Are you kidding me!”

“Well, yeah, but I’ll fix it! I promise! Look, there’s a bunch we can salvage!” Annie replied, jumping to her feet and turning around to present the destroyed jail. 

All that remained of the Copperbrooks’s former jailhouse was a pile of crushed bricks, iron bars, and the perfect indent of Annie’s butt in the middle. Casey turned around and frowned, to which Annie nervously chuckled and readjusted her hat before clearing her throat.

“Well, at least we know now what it takes to pull off a…‘prison break’, amirite?”