Dragon of the Wild West

Name: Dragon of the Wild West (Part 1)

Series: High School DxD X Overwatch

Ship: Issei Hyoudou X Ashe

Kinks: AU, crossover, sheriff Issei, femdom to maledom, prison sex, oral sex, blowjob, rimming on female, vaginal sex, anal sex, rough sex, creampies

Summary: In a town that was filled with crime, there was one man who could save the people, a perverted sheriff with a powerful weakness for sexy women.

A good bit away from the populated city was a small but lively town in the more deserted area of the lands. The town was small compared to the big city, but the people living in the town were very happy and lively. The people were happy with each other and lived happily for a long time.

But with every batch of fresh oranges, there are always a few rotten ones that ruin the fun for everybody else. A couple of years ago, the town suffered significant damage from criminals who saw it as an easy target, given its smaller size compared to the big city. There was barely any real security in the town, which made it easy for people to steal, rob and kill with little to no consequences.

This turned the peaceful and happy town into a high-crime town, ruining its once-happy and peaceful atmosphere.

This happened for several years until one man appeared and handled the problem with an iron fist. That person was a regular town citizen named Issei Hyoudou. Despite being one man, he managed to change the town for the better by fighting the criminals.

For the next six years, Issei was considered a hero in the town. He fought the bandits and criminals and drove them away from the town or captured them before handing them over to the city police. His efforts were recognised by the people and the police, who even awarded him the title of sheriff, making him the law enforcer of the town, which Issei gratefully accepted.

The town's people loved Issei. How could they not? He was their hero whom they had needed for so many years, and he handled all of their problems without gloating or taking any reward from it. He was the perfect hero in their eyes.

But every hero has a flaw, and that flaw has been exploited on several occasions. While Issei was a very good person, he had one major weakness: a sexy woman. While he doesn't abuse his position as sheriff, it is clear that Issei likes the company of a beautiful lady after a long day of fighting criminals and capturing them. It became quite known that the sheriff was a pervert, and the people didn't seem to be all that bothered by the fact that he was one. He didn't use his position in power to get what he way from women, and he never forced a lady to do something against their will.

The people loved that about him, and any lady who liked the sheriff wasn't shy to give the man a tease or even indulge the night with him. It was all good for everybody in the town. But that weakness towards a sexy lady was also well known to the criminals who were either from the run or were fighting with the sheriff daily.

Some female criminals tried to use their bodies to get out of trouble or even tried to assassinate the sheriff. But Issei wasn't a fool and knew that he couldn't let his dick decide what he should do.

But one time, in a moment of weakness, a female prisoner that the sheriff caught in the holding cell, who was going to be transported to the prison in the city, managed to seduce the sheriff into sleeping with her in return for securing her freedom.

Issei knew that it was wrong. But his dick was getting the better of his thoughts. One time turned to multiple times as several female criminals who he had captured managed to escape custody before they would have been transferred to a real prison.

Of course, the town started to notice those things. A criminal who has been captured being free the next day made no sense. And those criminals happen to be only female and good-looking. It didn't take long for the people of the town to connect the dots.

There have been several cases of known female bandits and criminals that Issei captured, somehow escaping custody the next day for reasons unknown. The prison doesn't have any cameras, so nobody knows how it happens.

So, it was clear that the Sheriff could be easily persuaded with a little bit of skin showing and perhaps some sexual favours if you happen to be a sexy female.

A well-known criminal by the name of Ashe was captured again by the Sheriff, as he had caught her after a long chase when she robbed the bank. Walking through the city, getting dirty looks from the people, Ashe, who was a beautiful white-haired lady, was being led towards the holding cells where she would stay a night before the city police would come and escort her to a proper prison.

But since it will take a while for the police to get to the town, Ashe had to stay in a holding cell for the night, which meant that she had one night to free herself somehow or else she would be stuck in a real prison for a long time.

As the Sheriff was dragging the criminal to the holding cell, people were cheering for the criminal's capture. However, some of the men who had heard the rumours about the Sheriff possibly letting the criminal go began whispering amongst themselves.

"I bet you three gold coins that Ashe escapes tomorrow." A cowboy said to another cowboy who puffed a bit of his cigar.

"Nah, have some more faith in our Sheriff. He might be a horndog, but letting female criminals go because they are dropping their panties for him is wild." The second cowboy said as he didn't believe the rumours.

"We'll see. So, you in?" The first cowboy asked, and the second nodded in agreement. They decided to wait and see if the rumours were true, since Ashe has been known to be captured by the Sheriff multiple times and somehow escaped every time that she has been captured.

Issei continued dragging Ashe to the holding cell building, and the moment they entered the building, Issei opened the cell and pushed Ashe inside. The beauty still had her wrists handcuffed behind her back, which wasn't a bother, as she just walked into the cell, as she had been stuck in it several times by now.

Issei closed the cell and locked it. The sheriff glanced over at the white-haired beauty who walked over to the bars and pressed her face against the steel bars. "So, the usual?" She asked with a teasing smile as Issei's face didn't betray any emotion.

"Quiet." He replied while locking up the cell to make sure that Ashe can't escape. The cowgirl merely looked at the sheriff with a smile that said that she had already won this game.

"You know… this is the fifth time that you have captured me. People are sure to ask questions about why I keep escaping the day after being taken into custody. People will slowly lose the faith they have in their precious sheriff." Ashe's words spiked something within Issei, who merely reached out through the bars and grabbed Ashe by her neck and pressed her face against the bars.

"Even with those rumours flying around. The people trust me." Issei muttered, squeezing her neck a little, causing Ashe to choke nearly. But she didn't falter as a moment later, Issei let go of her neck, which allowed the white-haired beauty to take a step back to gather herself.

Issei took the chance to turn around and was about to walk away, but before he exited the room, she blew him a loud kiss that made him stop for a second.

"Catch you later, my hero," she said as Issei left the building, knowing that he would be back for her. They have played this game multiple times before, and this one wasn't going to be any different.

Ashe stared at the door before thinking to herself. "It's been a minute since I had some good action… I guess we can amp some of the fun tonight…" She mused to herself before walking back into the cell and sitting on the floor, as she just had to wait before her freedom would arrive right at the gate of the cell.

(Later)

A few hours had passed as Ashe was still sitting in her holding cell. It was the middle of the night now as Ashe was still patiently waiting for the Sheriff to visit her cell.

"He's taking longer than usual… that cocky bastard…" Ashe mused. Right on cue, the door to the room opened up, which caused Ashe to smirk. 'Speak of the devil…' she thought to herself as she slowly moved herself from the wall and stood back on her feet, which was a bit annoying since her wrists were still handcuffed behind her back.

The Sheriff walked over to the holding cell where Ashe was. He turned on one light, which brightened the room a bit, but it was still mostly dark, which gave it a rather ominous atmosphere.

Ashe, who was now on her feet, looked at the Sheriff with a small cocky smile on her face. "It's rude to keep a lady waiting, Issei," Ashe said casually, like she and the Sheriff were good friends.

"You're a criminal first and foremost," Issei replied as he tried to keep his composure. But Ashe knew that Issei was here for one specific reason, which made her slowly walk over to the cell bars and press her body against them, her face resting in between two of the bars as she looked at him with nothing but devious intentions.

"And you are the Sheriff whose job it is to keep filthy criminals like me locked up. But here you are… willing to make another deal with a criminal like before. You truly are a disgraceful man, Sheriff." Ashe teased as her sharp eyes locked onto Issei.

The Sheriff took a step forward as he was standing right infront of the famous criminal. "You're one dangerous woman, Ashe," Issei muttered, making Ashe lick her lips as she looked at him with nothing but amusement, but also lust.

"And you're a corrupted man, Issei. Now come here and get you some…" Ashe muttered, despite using seduction to get what she wanted. She had to admit that having sex with the Sheriff was the best sex that Ashe had ever had, which is why she sometimes let herself get captured, just so the two could have a night that they could hook up.

Issei sighed as he hated himself for being such a pervert. But he couldn't let the chance slip through his fingers now. He took a step forward and leaned in towards Ashe's face as he began making out with the criminal, who eagerly kissed him back.

The Sheriff and the criminal soon started making out passionately, with the cell bars being in between them. Ashe was dominant in the kiss first, her tongue exploring Issei's mouth for a bit. But Issei wasn't going to let the cowgirl get what she wanted as he began pushing back with his tongue, slowly overpowering Ashe's tongue, and now he was the one exploring her mouth.

Ashe moaned a bit in the kiss as she pressed her body harder against the cell gate, and she began feeling this heat rush through his body. The two continued making out for a bit until Issei broke the kiss as he wanted what he came for.

"If you want your freedom back, you will have to work for it," Issei muttered, causing Ashe to smirk as she immediately went on her knees.

"Then what about that shotgun, and let me polish it with my mouth," Ashe said with a bit of impatience in her voice as she wanted this as much as Issei. The Sheriff smirked a little bit as he reached out to his belt and pants with a swift tug, pulling them down, revealing his semi-hard, large shaft that made Ashe lick her lips with excitement.

"Looks like someone is excited to see me." She teased, which caused Issei to smirk a bit as he stood right by the gate. He pushed his dick right in between the bars like it was some glory hole. Ashe licked her lips as her favourite toy was finally infront of her face.

"Shut up and get to sucking, lady," Issei demanded with a tone of impatience that caused Ashe to smirk a bit.

"Oh, has it been a while since you got some?" Ashe teased again as she pressed her face against Issei's dick. She let the impressive length rest on her beautiful face before she started kissing the bottom side of it with her mouth.

"Either you start sucking or else I'm keeping you here and giving you to the police tomorrow." Issei threatened with a serious tone that made Ashe start attending to Issei's dick as she knew that the moment the police got her, she was going to jail, which was a massive problem for her.

"Okay, okay, Jeez, I was just playing," Ashe replied as she began licking the bottom side of Issei's dick with her wet tongue. Issei exhaled as he enjoyed the feeling of Ashe's tongue that was lapping the bottom half of his dick for a bit before she brought her lips to the very tip of the Sheriff's dick.

Ashe glanced up and gave a sensual wink before she pressed her lips on the tip of Issei's cock and gave it a sweet, wet kiss. Issei's expression didn't change as he let the cowgirl do what he wanted from her.

While still maintaining eye contact, Ashe slowly opened her beautiful pink lips as she began moving her face forward, slowly taking in the sheriff's penis inside of her mouth as she began properly sucking his dick with the cell bars still in their way.

But while for some it might be uncomfortable, for the two lawbreakers, it was quite a turn on as it added to the whole sheriff and criminal secret relationship that they had.

Soon, the holding cell was being filled with wet sucking noises as Ashe was sucking the sheriff's dick in the sloppiest way that she could, as she knew exactly what turned the perverted man on.

It was hard to suck on a dick with her hands handcuffed behind her back. But Ashe always liked a good challenge, so she doubled her efforts and sucked on the sheriff's dick with all of her might, which Issei noticed as he exhaled a bit.

"Not bad, criminal… it seems that your mouth is good for something other than talking shit," Issei muttered out, causing Ashe to smirk with his cock in her mouth. She slobbered all over the length before she continued moving her face back and forth as fast as she could, making her saliva drool all over the lower part of her mouth.

'Fuck… you never know how much you missed something until you see it again…' Ashe thought to herself as she hated to admit it. But she loved having sex with the sheriff. He was a man with an extra-large and girthy tool, combined with the stamina to keep up with a woman of her stature.

Issei, on the other hand, brought one of his hands through the bars and placed it on Ashe's head as he massaged her scalp, sending strong jolts through the criminal's body as she couldn't help but moan around Issei's dick that was pushing deeper into her throat.

'Scumbag… he also knows my weak spots…' Ashe thought as she couldn't stop herself from sucking on the large cock as fast and hard as she could. Not wanting to lose to the sheriff that early, she kept bobbing her face back and forth on the dick, making her face nearly hit the metal bars of the cell as she continued sucking on the man's dick with all of her might, trying to bring him to his climax. It worked as Issei could feel himself slowly getting close to his edge.

"Fucking hell… your mouth hasn't changed a bit…" Issei cursed out as he couldn't contain himself for much longer. Ashe's eyes narrowed as she kept on sucking harder on the dick with all of her might.

Ashe had her lips tightly sealed around the length as she continued trying to push the sheriff over the edge. Her efforts were rewarded with a sudden, powerful eruption of cum that filled up her mouth, which made her eyes widen for a moment before they returned to normal as the cowgirl swallowed all of the delicious seed that was filling her up.

Issei exhaled as he came quite a bit inside of Ashe, who eagerly swallowed every droplet of cum that came out of the sheriff's nuts. After a good minute of nothing but cum swallowing, Issei's balls were empty, which made Ashe slowly pull her mouth from the still hard dick as she exhaled the moment her lips left the giant prick.

"Oh, I've missed my favourite drink." Ashe mused as she couldn't stop herself from licking the girthy dick clean, just as Issei did, she wanted more. "So, what is next on the menu, Sheriff? You going straight to fucking me, or you want an appetiser before the main dish?"

Issei couldn't help but smirk a little as he pulled his dick from between the bars. He looked at the still kneeling Ashe with a hungry smile.

"An appetiser. Turn around and stick out your ass towards me." Issei ordered, causing Ashe to smile back as she slowly got on her feet.

"Could you remove these cuffs from me first. It's hard for me to move around with these on." Ashe suggested, causing Issei to suddenly reach out to her neck and pull her body towards the bars.

"Since when has a filthy criminal the right to bark orders at me? Either you obey me, or you are going to the gutter." Issei's dark words send a chill through Ashe's body, who, without thinking, submissively nods her head as she forgets that the sheriff could be quite a scary man if he wants to be.

"Yes, sir…" Ashe muttered in a way more submissive tone than before. She knew that the moment the sheriff was using that tone, playtime was over, and even someone like her was going to behave.

"Good girl. Now show me those goods that your mother gave you." Issei ordered because he was hungry and wanted to eat. Ashe nodded as she slowly turned herself around, her fat, juicy ass, which was only enhanced thanks to the tight leather pants that she was wearing.

Ashe rested her rear against the bars right infront of Issei. The sheriff wasted no time and, with expertise, reached out to Ashe's belt and unbuckled it without even having to see it. He then started pulling down Ashe's leather pants, allowing her beautiful, creamy, perfect, luscious legs to be revealed as she was wearing some sexy, lacy black panties underneath, which only enhanced the beauty of Ashe's ass.

"Fucking hell… it gets bigger every time I see it." Issei cursed out, causing Ashe to glance back with a tiny smirk.

"And it's all your playboy. Now do what you best and give me some of that premium tongue action." Ashe's tone returned to her teasing cowgirl style as she even shook her butt a bit for the sheriff, who felt his dick throb with excitement.

But deciding to have a taste first with his mouth, Issei reached out and pulled Ashe's panties down her thick, luscious legs, revealing her already wet vagina to the sheriff.

"Lean forward… press your asscheeks against the bars so I can have direct access to both of your holes," Issei ordered with a tone full of lust in his voice. Ashe nodded her head as she slowly leaned forwards, it was bit a bit difficult with her wrists cuffed to her back but she managed to balance herself while pressing her rear against the bars as now her vagina was right infront of the sheriff who got onto his knees so he could truly indulge in this tasty treat that was infront of him.

"Take as much as you want, darling…" Ashe muttered as she could practically feel the hunger coming from the man who was behind her. It excited her a bit as she soon felt Issei's tongue slowly licking against her pussy.

Ashe let out a small sigh as she kept pressing her butt against the bars. She enjoyed the feeling of the sheriff's tongue slowly licking against her folds.

"Goodness, how many women you've eaten to be this good at eating pussy?" Ashe asked, as she knew that she wasn't the only lady who had slept with the sheriff to secure their freedom or to get favours from the sheriff, who had a lot of power and influence in the town.

Issei stopped for a moment. "Enough to start a whole breeding farm." He replied jokingly, causing Ashe to smile a bit before a moan escaped her lips.

"Shit… keep going honey… you're making me feel great…" Ashe muttered out with a tone full of lust. Her whole body kept on trembling as she could do nothing but shake on her feet as she felt herself slowly heading towards her climax.

Issei's mouth was still latched onto Ashe's pussy as he pushed his tongue deeper into her wet, delicious hole and explored her insides with skill and precision that Ashe couldn't find in any other man.

"F-fuck~!!" The cowgirl shrieked as her juices squirted a bit out of her hole directly onto Issei's tongue and the prison floor. Ashe shuddered a bit on her feet as it had been a minute since she had climaxed like this, and it was all thanks to the sheriff, who was the only man capable of making her feel good with little effort.

"Delicious like fine wine." Issei mused as he licked Ashe's pussy a bit to get the last bits of her juices out of her honeypot.

"Oh… fuck… you're a drug that no woman can't get enough of…" Ashe mused as she exhaled a bit while still keeping her position. Issei smirked as he slowly brought a finger to Ashe's vagina, teasing her hole a bit.

"Oh, I know, sweety. You aren't the first woman who came crawling back with their panties already pulled down to their ankles. And you will not be the last." Issei said with a slight cocky smirk on his face as he reached out to his pants and pulled out his keys.

"Come here, for being such a well-behaved prisoner, you deserve a little bit of freedom," Issei said, causing Ashe to stand back fully straight as she let the sheriff take off her handcuffs from her wrists, allowing the cowgirl to move her arms freely.

"Thank you for your kindness, sir. What is the next time you want me to do?" Ashe asked as she still had her rear pressed against the bars, as she knew that the fun was far from over with the sheriff.

"Show me your asshole. I'm in the mood to have a taste of that fine, juicy ass of yours." Issei demanded, causing Ashe to smile as she happily reached out to her rear and spread her buttcheeks apart, revealing her perfectly clean, beautiful backdoor that was inviting Issei in.

Ashe pressed her spread-open cheeks against the bar harder to push the entrance of her back door further towards Issei's face. "Come and get it, love. You're the only man that is ever to touch this hole."

The sheriff licked his lips as he wasted no time pushing his face forward and began licking Ashe's asshole with his tongue. Ashe let out a small sigh as the feeling of her asshole getting licked by the sheriff brought a great wave of pleasure towards her body.

Realising that she could use the bars of the prison cell to keep her cheeks spread apart, she moved her hands so she could bring them to her own body as she pulled open her dress shirt so she could start touching her chest. In contrast, another hand of hers went directly to her dripping wet cunt as she began touching herself while her asshole was getting licked.

"Oh yeah baby… keep going… your tongue feels amazing…" Ashe moaned out as her face was filled with pleasure in a way that none would ever expect of the well-known criminal. Ashe couldn't help but bite her bottom lip as her pussy kept on gushing onto her fingers, which she was digging deep into her snatch.

Issei's tongue started to push into Ashe's butthole, causing a strong surge of pleasure to run through her body as she couldn't contain herself, and she climaxed onto her hand.

"F-fuck~!" Ashe cursed out again as Issei's tongue was capable of making her feel amazing in a way that no other man was able to come close to.

Issei kept teasing Ashe's asshole for a bit, his tongue pushing into her rear, slowly lubing it up as the horny sheriff was going to indulge himself tonight.

Ashe kept touching herself for a bit until Issei suddenly stopped, which caused her to turn around to look behind her. "Why did you stop?" She asked as Issei just stood up onto his feet and grasped his fully hardened dick with his hand and gave it a few strokes.

"Because it is time to indulge in the main course," Issei replied as Ashe bit her bottom lip as she felt the tip of Issei's cock slowly rub against her back door. The feeling of dick pressing against her butthole brought a strong shudder through Ashe's body as she braced herself for a very rough ride.

"Bring it on… I'm not an easy horse for you to tame." Ashe challenged with an aroused smile on her face. Issei just flashed her a grin as he slowly started to push himself inside of her asshole, spreading her anus hole wide apart to make room for the girthy, long shaft.

"We will see Ashe… My gun is capable of taking down the fiercest of beasts, and you won't be any different." Issei assured as he kept pushing his dick deeper into the cowgirl's asshole. Ashe tilted her head back as she felt her asshole getting spread wide open by Issei's massive dick.

'F-fuck… this dick is too good…' Ashe thought in her head as she knew that she won't be able to sit properly for the next couple of days when Issei was done with her. But it was all worth it in the end.

Issei licked his lips as he brought his hands through the bars so he could place them onto Ashe's amazing hips. He smirked a bit towards the white-haired beauty as he kept pushing more and more of his dick into Ashe's asshole.

"You're tighter than usual. You missed my dick inside of your ass?" Issei asked while still pushing more of his cock into Ashe's body, who tried to keep herself composed. But it was quite hard with such a girthy shaft entering her body.

She couldn't hide it as she gave a weak nod and confessed. "I missed it… a lot…" Ashe muttered as Issei's dick was still pushing deeper into her asshole, which caused Ashe to feel a level of pleasure that she wouldn't find anywhere else.

"Good girl…" Issei muttered as he stopped pushing his dick forward. He gave Ashe a moment to breathe before he began moving his body back and forth at a slow pace.

"Oh fuck yes… I missed this… more sheriff… fuck me more with that… incredible dick…" Ashe pleaded with pure need in her voice. The sheriff couldn't help but grin. How could he say no to such a request?

"As you wish, my lady," Issei replied as he did exactly what Ashe asked of him. His pace started to build up. The holding cell was soon filled with wet, slick noises as the sheriff continued fucking the prisoner's asshole, who in turn started to let out more moans in the cell.

"Y-yes… more… y-your dick is the best thing… this town has to o-offer~" Ashe moaned out as her pussy was leaking with her fluid without having to be touched.

Ashe's arms were just dangling from her body as she let the sheriff do all the work, who was more than eager to fuck her asshole as he wanted.

"And you better never forget it. Your body is my property." Issei groaned out as his hips began smacking against the bars as he was trying to push as much of his dick inside of Ashe's asshole as he could. But naturally, the bars of the cell were holding him back from fully pushing his dick into Ashe's asshole.

But that wasn't an issue for the sheriff, who kept on thrusting his hips against the bars, pushing as much of his dick inside of Ashe's asshole as possible, who was starting to make slutty faces that nobody except the sheriff had ever seen on her face before.

"Fuck me~! Fuck me with that big fucking dick, sheriff~!" Ashe shrieked as she was losing herself to how incredible Issei's dick was making her feel. The pervert licked his lips as he happily complied with the prisoner as he continued fucking her ass as hard as he possibly could, as the tightness of her backdoor was straight up addictive for the sheriff of the town.

"That's the plan bitch… fuck your ass is too good… I'm going to cum soon, Ashe… take my cum in your fucking ass!" Issei roared as he kept ramming his hips against the bar to push as much of his dick inside of Ashe's asshole as possible.

Ashe's eyes went cross from how incredible she felt as she could do nothing but climax from the giant dick that was ramming into her butt. Issei, on the other hand, gave one final thrust before he started to load his cum directly into Ashe's asshole.

The white-haired beauty could do nothing but stare infront of her and climax over and over again from Issei's cock that continued filling up her asshole with nothing but cum. Ashe's body was spasming a bit from how amazing it felt to have her asshole getting creampied by the sheriff.

She was breathing heavily while also barely being able to stay standing up as Issei's cock was still gushing inside of her ass. When the pervert was finally finished dumping his load, he slowly pulled himself out of Ashe's asshole, which allowed the beauty to fall onto her knees, breathing heavily from the intense anal fucking that she had just gone through.

As Ashe was catching her breath, the sheriff looked at the prisoner and felt a second wind rush through his body. Without saying a word, he picked up his keys and opened the gate of the cell.

Ashe, who barely had time to regain her bearings, was suddenly met with a wet dick pressing against her face as Issei was now in her cell with his cock right infront of her face.

"Clean it bitch." Issei ordered with a lustful look on his face as he practically thrust his dick towards Ashe's face.

"Yes, sir…" She muttered out with a more submissive tone as she was still exhausted from the rough anal fucking that she had just experienced. Without wasting any more time, she opened her mouth and took Issei's dick back into her mouth to start sucking it again.

Loud sucking noises came from Ashe's mouth as she sucked on Issei's dick that had just come out of her ass. The sheriff smirked a bit as he pushed a bit of her hair out of the way.

"Now that is a good girl… keep sucking, Ashe," Issei muttered as he made sure that Ashe sucked his dick clean. Ashe glanced up as she sucked on the sheriff's dick as hard as she could for a bit, filling the holding cell with loud sucking noises, which only turned both of them more on.

After a minute of sucking, the sheriff pulled Ashe's face off his dick and looked down at her with nothing but hunger in his eyes. "On your feet, prisoner," Issei muttered as his dick was throbbing with need. Ashe gave a weak nod of her head as she slowly got to her feet. Her legs trembled a bit from the brutal assfucking that she had just received just a few minutes ago, but when she got back on her feet, Issei lifted her from under her legs and pushed her back against the cell bars.

Instinctively, Ashe's hands reached out for the bars to hold onto as she looked at the sheriff, who was holding her against the bars, ready to fuck her inside the cell.

"Make me my sheriff… fuck this lowly prisoner with this giant dick of yours…" Ashe muttered with clear desire in her voice as she wanted this just as much as Issei wanted it. The sheriff looked the white-haired beauty right in her eyes as he kissed her on the lips for a bit before slowly rubbing the tip of his cock against her vagina and slowly pushing it in.

Ashe's eyes widened as she felt her vagina get invaded by the sheriff's mighty shotgun. Her whole body trembled at the feeling of the large dick slowly sliding into her wet, tight hole, spreading her insides apart in a way that only Issei was capable of doing.

Ashe's whole body trembled as she could do nothing but clutch the cell bars as hard as she could while her toes curled in the air.

"F-fuck me… oh I've m-missed this big fucking d-dick…" Ashe cursed out as it felt like she was having a seizure from how incredible her body felt from having Issei's dick filling her up.

"And I've missed this amazing pussy on my dick…" Issei muttered back as he kept on pushing more of his dick inside of Ashe's vagina, who, in turn, moved her legs so she could wrap them around Issei's midsection for better support.

"Then fuck me all you want, you stallion… make me never forget how amazing that big dick of yours is!" Ashe's words were like adding fuel to the fire. Issei's eyes were filled with determination as he stared her right in the eyes before he began moving his hips back and forth as fast and hard as he could.

The holding cell was soon filled with loud skin slapping noises as the sheriff and criminal were anything but subtle. If it weren't thanks to the building being soundproof, then most townspeople would have heard the obvious fucking that was happening in the holding cell.

Issei clenched his teeth hard together as he kept on ramming his dick as deep as he could inside of Ashe's vagina, causing his balls to slap against her rear, which only added to the incredible pleasure that both were feeling. Ashe's eyes were darting all over the place as her pussy was in a state of constant orgasms.

"Fuck~! Fuck~! Fuck~! Fuck~! Fuck~!!" Ashe kept on cursing as she could barely contain herself from how incredible she felt. Issei looked at her with nothing but sexual desire in his eyes as he kept on ramming his hips against her bottom with all of his might.

"Fucking hell Ashe… your pussy is way too good…" Issei groaned out as he couldn't stop himself from ramming his dick as deep as he could into Ashe's pussy. The white-haired cowgirl moved her arms to wrap them around Issei's neck as she looked at him with nothing but pure hunger in her eyes.

"Then fuck me harder, you stud! Fuck me so hard that I can't ever feel another dick inside me again!" Ashe yelled as she was losing herself to the pleasure that the sheriff was making her feel.

"I will! Since you love playing this game… I'm going to fuck you the entire night!" Issei roared while leaning forward to stare Ashe right in her eyes. The criminal stared right into the sheriff's eyes with nothing but pure bliss in them. She could do nothing but lean forward as she captured his lips with her own, as she made out with Issei, who still kept ramming his dick as hard as he could inside of her.

Loud skin-slapping noises filled the entire prison as Issei was going all out on her body.

When the sheriff was about to cum again, he didn't give Ashe any warning as he kept thrusting his hips faster and harder until he came. When he reached his peak, he bit into the criminal's lower lip while slamming his crotch against her vagina and kept it there as he started dumping his load into her vagina.

Ashe's eyes widened before they rolled up as she could do nothing but accept the powerful, potent cum load that was filling up her vagina. 'S-so much… fuck~! I love this dick!' Ashe cursed in her head as she could do nothing but climax on the sheriff's dick that was filling her pussy up to the brim with cum.

After a whole minute of nothing but cumming, Issei slowly lowered himself and Ashe's body towards the ground. His dick was still inside of her pussy while Ashe had her arms around his neck for dear life.

Slowly, both the sheriff and the criminal started to come down from their sexual high. Issei was still holding onto Ashe's body and kept her close while the beauty was breathing heavily with sweat all over her beautiful face.

"Now that is my kind of ride…" She mused while slowly sitting up on Issei's lap, as she still felt his dick inside of her pussy, which was now filled with his cum. She looked down at Issei, who was staring at her without saying a word.

She gave a small smile before kissing him on the lip as she played with his brown hair. "You still have some gas in the tank? I didn't let myself get captured by you only to go two rounds. You'd better keep your word to me about going the entire night." Ashe teased, causing Issei to exhale before looking at her.

"Oh… don't worry, my dear criminal. You won't be getting far tomorrow when I'm done with that sexy body of yours…" Issei muttered, causing Ashe to smirk back at him.

"That is what I like to see, cowboy. Show me what you got." She replied slowly, standing up, letting the large dick slide out of her freshly fucked pussy as she wanted another round and looked forward to what the sheriff had in store for her.

Soon, both Issei and Ashe were completely naked, and all their clothes were discarded on the ground as the two were furiously making out with each other in the middle of the holding cell.

Both just wanted each other, and neither was going to stop until both of them were thoroughly satisfied. While Issei and Ashe were making out, Ashe had his dick in her hand, which she was jerking a bit while she was still kissing him.

After a minute of nothing but kissing, Ashe slowly got back on her knees as it was time for her to clean his dick again, which was coated with her vaginal fluid.

Licking her lips with clear desire in her eyes, she leaned forward and took Issei's dick back into her mouth to suck it, which caused Issei to bring his hand to her hair and push her white locks out of the way.

"I can never get tired of that mouth of yours, Ashe." Issei mused as Ashe just knew how to work her mouth on his dick in a way that nobody else could do. The criminal looked up and flashed him a sultry wink as her mouth started to go up and down again on the dick.

Issei exhaled as Ashe sucked his dick for a good minute, the feeling of her soft puckering lips squeezing around his length and not stopping until she got what she wanted was driving the sheriff insane with lust.

Ashe's mouth kept bobbing on Issei's dick for a good minute until she suddenly pulled her mouth off the dick. "Paint my face white, sweety… give me a good ole creampie…" Ashe mused as she moved her mouth to Issei's nuts to slobber all over the man's nuts while her hand proceeded to jerk the fat dick, causing Issei to chuckle a bit.

"As you wish… my lady…" Issei mused as he grasped his dick and jerked it with his hand, and jerked himself right infront of Ashe's face.

Ashe licked her lips as she continued licking the very tip of the cock as she watched her lover jerk himself right infront of her face. Issei kept jerking his dick in her face for a good minute, slowly bringing himself to his climax as he was getting ready to paint her face white with his cum.

"Fuck…" Issei groaned out as his semen started spraying all over Ashe's face. The criminal pulled back as she let her beautiful face get showered by the thick chunky ropes of Issei's cum that splattered all over her face, giving her a bukkake with just one cum load.

"Fuck… that was good…" Issei groaned out as he kept jerking his cock for a bit to make sure that he got every bit of cum out of his dick. Ashe smiled as she gloated in the creampie that she was receiving. When Issei was done cumming, he took a step back to gather himself, as even with a man with his stamina, he needed a small break every once in a while.

Ashe took this moment to slowly scoop some of the cum from her face and brought it to her mouth. She licked the cum off her hands like she was a cat as she made sure that she made it look as hot as possible for the sheriff, who was staring down at her with nothing but arousal on his face.

"Fuck Ashe… you really know how to make a man happy," Issei muttered out as he stared at the criminal who continued cleaning her face from his cum as she made sure that none of the creamy white seed was going to waste, as it was the highest quality of cum in the town.

"A man of your skills and talent deserves to get more than the average rookie," Ashe muttered as she wiped the last bit of cum from her face. When her face was completely clean, she slowly stood back on her feet and smirked at the sheriff.

"So what now, sheriff?" She asked, placing her hand on her hips while showing off her amazing curvy figure that Issei was addicted towards.

"Hands on the bar and stick out your ass towards me. Time to teach a slutty inmate like yourself a lesson." Issei answered while flashing her a horny grin. Ashe licked her lips with excitement as she turned herself around and walked over to the bars before grabbing onto them.

She took a few steps back as she was now sticking out her ass towards the sheriff as much as she could while arching her back in the sexiest way that she could manage.

Ashe looked back at Issei and flashed him a sultry smile while shaking her juicy, creamy ass for him. "Come and get it, sheriff. Teach this criminal a lesson." Ashe teased in a tone that ignited Issei's fire within his body.

He smirked a bit before walking up to Ashe. He gave her ass a good slap, which sent a strong tremor through her body.

"Oh, I will…" Issei muttered as he grasped his dick with one hand while his other was on Ashe's hips. He guided his dick towards Ashe's delicious-looking pussy, which was oozing a bit of Issei's previous cumload, which, in his opinion, made Ashe's pussy look even more appealing to him.

The sheriff took a deep breath before slowly pushing himself inside of Ashe, who in turn grasped the bars of the prison cell with a deathgrip, as no matter how many times they fucked, she would never get used to the shape of Issei's cock, and she loved every bit of it.

"Oh yes… stuff that dick back in me… I think I might not be able to live a normal life without this big cock fucking me…" Ashe's words aroused Issei even more as, while he was moving his dick further inside of her vagina, he gave her ass a good slap that sent a strong tremor through her body.

"Then I keep you around as my bitch and fuck you every chance I get." Issei's words, combined with his dick pushing deeper into her pussy were turning Ashe on. She weakly nodded as she knew that this was just in the moment, and she gave in.

"Yes… fuck me! Fuck me every day, you fucking stud!" Ashe cursed out as she came again on Issei's dick. The sheriff clenched his teeth as he began moving his dick in and out of her pussy, fucking her at a strong, steady pace against the bars within the prison cell.

"I will… I'm going to fuck you so hard that you will never be able to leave me, Ashe!" Issei roared while thrusting his dick as hard as he could. His brain was filled with endless clouds of lust as he couldn't stop himself from reaching out to her amazing ass and giving it a harsh slap.

Ashe moaned louder in return as her pussy was gushing all over Issei's dick while her body was trembling from how incredible she felt. "Fuck~! Fuck~! Fuck~! Fuck~! Fuck~!" Ashe kept cursing out with the sluttiest smile on her face.

Her body was coated with a thick layer of sweat, as this was undoubtedly the most physically intense thing that she had done in quite a while. The same was for the sheriff as he was giving it his all in fucking the slutty criminal with his raging dick that was slamming against her womb.

The sheriff brought his hands to both of Ashe's hips as he kept on thrusting his cock as deep as possible inside of her pussy. His eyes filled with sexual hunger as he continued fucking the white-haired beauty like he was a beast possessed.

"Dammit, Ashe… your body is too good… I'm going to cum again soon." Issei muttered out while still moving his body back and forth as much as he could.

Ashe nodded her head as she had trouble forming forward from the constant feeling of her insides getting rearranged by the massive prick.

"C-cum… cum in me…" Ashe moaned out as she could do nothing but clutch the bars of the prison for dear life. Issei grasped her hips harder as he kept on thrusting his dick as hard as he could inside of her.

Eventually, the sheriff was close to reaching his load. He kept on moving his body as much as he could, as he was ready to blow another load into the criminal's vagina.

"Cumming~!!" Issei roared out as he gave one final thrust before he began shooting his load into her vagina again. Ashe's face stuck making the same slutty expression as she could do nothing but stare infront of her with nothing but pure bliss visible on her face as her body couldn't stop vibrating from the constant feeling of her insides getting painted white again and again.

Ashe was gripping the bars of the cell so hard that it seemed she was trying to bend them. Her whole body was trembling as she could feel her insides getting filled to the brim with nothing but cum.

After a good minute, Issei slowly came down as his legs were giving out from cumming so much in such a short period of time. Issei dropped onto his ass, causing his dick to flop out of Ashe's vagina, which started leaking with semen a bit of semen.

Ashe slowly fell onto her knees as she was breathing heavily from all the fucking that she just went through. Her body was shaking as she could do nothing but gasp for air. Issei lay on the ground in the middle of the holding cell as his head was spinning from all the climaxes that he had just gone through.

"Fuck… I'm going to feel that tomorrow…" Issei cursed out as he took a moment to gather himself. But it seems that the criminal wasn't done with the sheriff, as the moment Ashe managed to regain her bearings, she turned around to look at Issei with a small smirk.

"Don't think… that this is over yet…" Ashe muttered as she crawled over to the exhausted sheriff, as she was going to milk him for everything that he had. Ashe slowly got on top of him with her ass towards his face. She was now in a reverse cowgirl as she used her hand to jerk Issei's dick a bit to get it fully hard.

"Ashe…" Issei muttered as he was completely spent. But it seems that the criminal wasn't going to stop just yet. When Issei's dick was erect again, she slowly lifted her ass and lined up his dick with her butt before slowly lowering her rear and slowly devouring Issei's cock within her asshole.

"Sorry, hun… but you wanted this. You are about to get it." Ashe said with a smirk as she began bouncing her amazing fat booty on Issei's dick. The sheriff could do nothing but watch as Ashe was fucking herself on his dick, which felt both incredible and very draining.

"Fucking hell…" Issei groaned out as he let the criminal have her way with him. He just reached out to her hips and grasped them while Ashe continued bouncing her booty on his crotch, which was begging for a break.

"Oh yes~! Now I'm the one riding this stallion…" Ashe muttered out as she kept fucking herself on Issei's dick. The sheriff just looked at her with a face filled with pleasure and discomfort as it felt like his dick was about to fall off from how many times it had been fucked today.

"Ashe…" Issei groaned out as he could barely contain himself for much longer. The white-haired cowgirl just glanced back with a small smirk on her face.

"You're going to cum again? Do it… fill my ass up with your cum, my dear sheriff…" Ashe's words send chills running through Issei's spine. He looked at the amazing ass of the prisoner as he could barely contain himself anymore.

Using his hands that were on her hips to slam her body down on his dick, he slammed her amazing booty down on his dick right before he came.

Ashe's eyes rolled back into her head as she felt her asshole getting filled with cum for the second time. Her whole body trembled as she shuddered on the bed with nothing but pure pleasure visible on her face.

"Oh yes~!!" Ashe's moan filled the cell as she kept her butt pressed against Issei's crotch, as she continued milking his dick for every droplet of cum that he had.

After a minute, Issei's balls were empty. He just lay on the ground of the cell with a look of bliss and utter exhaustion on his face as he could do nothing but stare at the ceiling of the cell with a look that said that he couldn't take any more.

Ashe took a minute to gather herself as well. But when she came back to her senses, she slowly turned herself around and lay down on top of Issei's body. She looked down at him with a small smile before kissing him on the lips.

Issei weakly returned the kiss as he just wanted to sleep now. Ashe broke the kiss while looking down at him. "Thanks for the amazing time, my sheriff. I promise not to do anything for a while." She muttered before standing up as she stumbled a bit while gathering her clothes. Not bothered by the fact that she had cum leaking out of both of her holes, she pulled her panties up to keep as much of Issei's cum inside of her body.

With a smile on her face, Ashe put on her clothes as the gate of the cell was already open. When all of her clothes were back on, she glanced back over to the sheriff and blew him a kiss before leaving the cell, as Issei was going to have a fun time explaining how Ashe escaped again.

"Fuck me… and my stupid dick…" Issei cursed at himself as he was hopeless when it came to sexy women.

(The next day)

The two cowboys who made a bet on whether Ashe escaped her captivity were at the bar. They were waiting for any news about the criminal, as things have been quiet lately.

"Looks like I won." The cowboy who bet that Ashe didn't escape her cell said as the other guy just narrowed his eyes.

"The day isn't over yet." The first cowboy replied as right on cue, the radio started to announce something.

[Breaking news: Notorious criminal Ashe has escaped her captivity and escaped the town.]

"Ha!" The first cowboy cheered with a grin. "Give me my money, boy."

The second cowboy grumbled something under his breath while taking out a few gold coins and passing them to his buddy.

"How the hell did she escape for the fifth time? This can't be normal." The second cowboy said, causing the first one to shrug his shoulders while taking the coins.

"Whatever the reason is. It's making me some money and I'm all for it." The first cowboy said with a grin as the two happened not to notice a tall lady walk into the building with a small smile on her face.

"Excuse me, gentlemen. Can you two point me to the sheriff of this town?" The woman asked, causing the two guys to turn around and be surprised at the very tall woman who was towering over them. "I wish to have a word with him."

"W-wait, you are…" The first guy stammered as he recognised the woman.

"Nico Robin…" The second guy finished the sentence, causing the tall lady to smile.

"That I am."