A Hero's Misfortune

Author's note: This has been edited to fix some of the pacing issue. Hope you enjoy!

"Last round." The bartender said. He was a gruff man with a smooth bald head. "Whoever loses owes the winner 100 gold."

Cass was playing a game of blackjack with Sidra, the tavern's waitress. A shorter woman with dark skin and curly hair that went down to her shoulders. They'd been playing for a couple of hours and ended up tied. But Cass wasn't worried. He was the chosen one after all, and he couldn't lose. Sidra drew a king, followed by a nine.

She grinned as she placed them down. "Your turn."

It didn't look good, but Cass wasn't a cheater. He reached over and grabbed two cards. By luck that he could only assume came from the god's favouritism, both cards were a ten. "Well, would you look at that? Guess I won."

"Fuck!" she scowled.

Cass grinned and motioned for her to hand over the gold. Sidra looked away from him and scratched at her cheek. "I... I don't have that kind of gold on me right now. If you could wait a couple days, I could- "

"A deal's a deal." He shrugged. "Time to pay up."

"What if I pay you what I have on hand and show you my tits to make up the rest?"

Cass looked her up and down, taking in her figure. Her breasts weren't too big, but they had a nice shape that paired well with her slim waist and round ass. "You've got yourself a deal."

Hesitantly, Sidra slipped her thumbs under her top and lifted it. With no bra to hold them in place, they bounced a bit before settling. Her nipples hardened in the cool air. Overall, they were quite nice to see.

"If you let me touch 'em, I'll consider your whole debt settled."

She thought for a moment, then nodded. Cass was tall enough that when he stood up, he towered over her. He grabbed a breast in each hand and gave them a gentle squeeze. To his surprise, they were incredibly soft and warm. Before now, he'd never actually touched a woman's breasts. Captivated by the feeling, Cass flicked one of her nipples with a thumb, earning a shocked moan.

"Cass!" She gasped and pulled her top down, "I think that's more than enough to cover my debt."

Her voice was stern, but when she turned to leave, there was a giddy smile on her face. Now that he was the chosen one, he had that effect on women.

"Don't mean to interrupt," the bartender said, "but you have visitors."

He motioned to three women at a table who looked at him with desperate eyes. Now that they had his attention, they approached him. The one in the middle was almost as tall as him with blonde hair and huge tits. Some of the biggest he'd seen. To her left was a woman of average height with red hair and a nice figure. Though not as big as her friend. On her right was a short brunette with breasts that were surprisingly large for her height.

"Hero." the short woman said nervously. "We need your help."

"How so?" Cass couldn't keep his eyes off their breasts. All three had a large amount of cleavage, and the blonde's dress could barely contain her breasts. One wrong move and they'd tear her top open.

"You might not remember me, but we grew up together in our village."

Cass looked her up and down. Now that Cass saw her face, she did look familiar. It took a moment before he recognized her. She had a massive crush on him when they were kids, claiming that one day she'd marry him.

"Siya?"

She nodded with a blush. "I'm glad you remembered! I thought you would've forgotten me after you left."

Cass placed a hand on her cheek. Her plump lips looked inviting, practically asking him to kiss them. And the way she looked at him... "How could I forget someone as beautiful as you?"

The blonde woman cleared her throat. "I'm Hex, and this is Brynn."

"Forgive me," he took a step away from Siya, "nice to meet you both. A friend of Siya is a friend of mine."

Both of them seemed to approve of that, especially Brynn who looked down and pulled at her long hair. "Would you mind if we went somewhere more private? We have something important to ask of you."

Three attractive women asking to be with him in private? Sounded like today was his lucky day. "Of course, I'll take you to my room."

The bartender gave Cass a wink as he led them down the hall. His room was the largest with a bed big enough for a few people. He hadn't told anyone before, but he was still a virgin. Despite his new rank, he was too nervous to court someone. But now was his chance.

Once inside, he sat on the edge of the bed. He didn't have any chairs for the three women, so they got on their knees in front of him. The way their dresses clung to them, with erect nipples poking through the thin fabric, it was clear that they weren't wearing anything underneath. Cass could feel his dick twitching with excitement, forming an impressive bulge down his pant leg. Siya stared at it in awe, Brynn blushed brightly, but Hex looked hesitant.

All was quiet until Hex cleared her throat. "Now that we have some privacy, there's something we need to ask you."

Brynn pulled her eyes off his dick and nodded. "The prophecy says that the chosen one would be incredibly strong. And on his quest to slay the Demon Queen, he would form a harem of virgin women to keep his bed warm and bare his children."

The two women looked at Siya expectantly, but she was too transfixed by his dick. Hex nudged her, causing Siya to look at them. "Hm? Oh right, sorry! We wanted to know if we could be that harem for you."

The other two nodded, their eyes suddenly serious.

"Please," Hex continued, "we're desperate. If we don't find a strong suitor, our bloodlines are over."

Cass looked at Siya. "I thought you had quite a few siblings. So, your lineage should be fine, right?"

"Not anymore." She looked at the others sadly. "A fire burned down our village during a raid and I was the only survivor of my family."

The three women silently moved closer, mere inches from his crotch. Brynn glanced between his legs again while Siya knowingly placed a hand on his upper thigh. Nearly touching his bulge.

Despite their obvious lust, it was a solemn request that he took seriously. But like them, his lust had already made the decision. He'd help these ladies by getting laid.

"All right then." He undid the front of his pants and a large dick flopped out in front of them. All of their eyes widened, and their mouths hung open in shock. "Let's get started then."

Siya made the first move. She slipped his tip into her mouth with fervor. Something she'd obviously been wanting to do since they met. Brynn looked envious but got to work kissing and licking his base while Siya struggled to fit him deeper down her throat. Cass felt like he was in heaven. It took all of his effort not to cum immediately.

Hex, however, sat back hesitantly with red cheeks.

"No need to be shy. It's big enough to share." He said gently.

"It's just that..." she watched the other two pleasure him. "I don't mind dick, but I have more of a preference for... women."

"Hey," the two girls stopped for a moment, "Don't rush it then. Do what you want to make yourself feel good until you're up for it."

She nodded and the girls started sucking him off again. Cass meant what he said, but he also wanted to fondle those giant tits of hers. They were a prize he couldn't have. Yet.

Instead of servicing him, she undressed herself and the other two while they worked. Then, she kneeled behind Brynn and reached around to cup her breasts. Hex fondled them while seductively kissing the other's neck.

It was so hot, that Cass couldn't take it anymore. For a brief second Siya's lips weren't around his dick, he blew several loads. His dick twitched with each one, shooting ropes of cum all over the faces and tits of the three women. Siya and Brynn looked smug about their work. Happy to have made him cum so much.

"That was hot," Siya said. She scooped some cum off her breast with a finger and licked it. "Mmm."

Seeing he was still hard, Brynn and Siya stood up and shoved him back on the bed. Hex watched excitedly as Brynn crawled up next to him and started kissing his neck with quiet giggles. Her breasts pressed against his arm.

Siya, however, was bold. She crawled on top of him, swaying her untouched pussy just above his tip. "I've been wanting to do this since we were teens."

She lowered herself until her tight pussy gently gripped his tip. But instead of taking him in, the cruel woman swayed her hips side to side, taking pleasure in watching him squirm in anticipation. The other two women giggled.

"I'll count to three before taking our virginities..." Siya leaned down and kissed his chest.

"One..."

She gently made a trail of kisses up his neck.

"Two...."

She licked her lips and kissed him, slipping her tongue in for a moment.

"Three..."

Before Siya had a chance to make her move, alarms sounded in the distance. One of the Demon Queen's generals had been sighted nearby. Not a moment later, the door to his room flew open as a soldier barged in. He didn't seem to care about the state he found them in.

"Fuck!" Cass shouted. "Now??"

Equally upset, Siya and Brynn joined Hex and put their clothes back on.

"But I'm so horny after that..." One of them complained.

"So unfair."

"We didn't even get to cum."

Cass was pissed but stumbled after the guard as he put his clothes back on. Behind him, the women followed him uncertainly. Their cheeks flushed red from a mix of embarrassment and frustration. The guard led them towards the city gates where a crowd of people were gathering.

"What's the situation?" Cass asked.

"The Demon of Onyx was spotted riding by on horseback." He said with a gruff voice. "Whole city's on alert. Last time he was spotted, he wreaked havoc among some of the villages."

As they pushed their way through the crowd, people started to notice him. The loud voices of a confused mob slowly grew silent as they watched him. Despite what he felt about himself, he was their hope. Their savior. Cass tried his best to imitate a posture that seemed confident and heroic.

"We have a horse for you." The guard said as they reached the wall guard's stables. "He's fast enough to keep up with that demonic abomination of a horse. You should have no problem catching up to him."

Cass looked around and noticed no one else was on horseback. The other soldiers looked scared. "Who's coming with me?"

"Uh...no one, sir." The guard said. "Only the chosen one can defeat a demon."

Cass's hands felt sweaty at the thought of facing a demon on his own. But it was his destiny. With the prophecy on his side, he couldn't possibly lose.

"Okay, but I want a horse for these women." Cass pointed at Siya, Brynn, and Hex. "Get them on horseback as soon as possible. If I fail, I want them to have a quick way out of the city."

The guard hesitated but nodded.

As Cass rode out, he heard the guard calling for someone to get them a horse. The large city gates creaked as they opened to reveal a wide-open field with distant hills on the horizon. Far away atop one of those hills was a powerful figure on horseback, waiting for him.

The silent crowd started cheering. Thanks, praises, and wishes of luck. A few women on the brothel's balcony shouted for him and then flashed their tits. Cass tried not to blush from the attention. If this was the response he got when leaving, he couldn't imagine the cheers when he returned.

With a wave, Cass rushed through the gates to meet his destiny.

In the distance, the tall armored figure disappeared over the hill. Cass snapped the reigns and charged after him. Although he was scared to fight a demon, he was also angry. He wanted to take his frustration out on the man who interrupted his chance of losing his virginity.

On the other side of the hill, out of sight from the city, the general waited for him beside his horse. A sign that he wanted a duel rather than a fight on horseback. Cass ignored it. Instead, he charged straight for him with a spear ready to impale. Right before he stabbed him, the general sidestepped and slammed a fist into his head. Everything went black.

Cass didn't know how long he lay there before he finally woke up. As he stirred, he heard voices talking. No, they were pleading with someone. Cass opened his eyes to see Hex, Brynn, and Siya standing between him and the general.

"Please don't kill him," Hex begged. "We need him!"

The general just silently stared down at them. And he towered over them. Even compared to Cass, he was at least two feet taller."

"We'll do anything." Brynn cried. "Anything if you let him live."

"Why?" the general demanded. There was something strange about his voice.

"We're to be his wives. So that he can save our family's bloodlines by giving us strong heirs."

"Him?" The general laughed and removed his helmet. It turned out that the demon was actually a she. A tall woman as beautiful as a goddess with long black hair. "I doubt he'd be able to provide the strong heirs you desire. He's weak."

Noticing he was awake, Siya helped Cass to his feet. Though he needed to lean on her for support, giving him a clear view down her dress. Now wasn't the time for that.

"He's not weak, he's the chosen one," Brynn said softly. Seeing the demon's face seemed to have made her uncertain.

The general easily pushed past Brynn and Hex and reached for Cass. With shocking strength, she grabbed his armour and ripped it off. It clanked on the ground in pieces. Then she tore his tunic and pants off, leaving him completely naked.

"With a little dick like that?" She snorted. "You three could do way better than him."

"I-it's" Cass stuttered. He tried to cover himself, but the general forced his hands behind his back and tied them together. His dick now exposed to the world. "It might not be the biggest, but six inches is at least average."

"Yeah!" Siya said, "Size doesn't matter to us. Nor does it make him inferior."

"I dunno." The general said. Then, she started stripping her armour. Each piece she removed made her more attractive. Toned arms, a subtle set of abs, thighs that could crush a skull, and a pair of large round breasts. But what surprised him the most was the massive cock that hung between her legs. "I'd call his size inferior."

Her cock was proportionate to her body, but since she was so tall... It was huge compared to someone like Cass's. She had to have been at least a foot long and three times as thick as his own. The three women, all of whom had defended him and vowed to be his wives, were silent. They just stared at her cock with obvious lust.

"I'll give you three a deal," the general said with a smirk. "Join me and become my wives instead, and I can provide you with as many powerful heirs as you desire. I'll even spare the little guy and bring him along as a slave."

There was a long pause as they thought about it. For a second, Cass thought they'd stand by him. But instead...

"I accept." Hex eventually said. She didn't look at him as she walked past. "Sorry, but I did say I preferred women. And now there's a woman with a massive cock promising to help me."

"I'm also sorry, but how could I say no to a cock like that?" Brynn left next. "At least we haven't had sex yet, right? So, we weren't properly bound."

Hex and Brynn got on their knees in front of the general and started pleasing her. Brynn fondled her heavy balls while Hex worked the tip with her lips. The general, with a smug look on her face, waited for Siya.

"Cass... I... It's not that size matters... I just..." She looked back and forth between him and the massive cock. After a long moment, she got on her knees with her friends. Fluids were already running down her thighs from anticipation. "I'm a virgin, so I didn't realize how small your little thing was. I love you, but I need this cock in me."

"Mmm." The general moaned. "Now you know how it feels to suck a real cock."

Cass watched in horror, unable to escape his bonds, as the three women pleasured someone else in front of him. Especially Siya. She was someone he had a crush on since they were little, and now he's forced to watch her give someone else a blowjob.

The three of them worked the cock for a while until the general pushed them aside. She grabbed her cock and stroked it furiously until she blew a load straight onto Cass's face. Then a second and a third, covering him in her thick cum.

"Fuck." The general breathed. "You girls are surprisingly skilled for being virgins. I'll be sure to return the favour with my cock tonight."

"Now for you." The general approached Cass. The three women followed behind with satisfied grins from the compliment. "You're my slave now, so you'll be coming with us. To make sure you don't play with my toys though..."

She pulled out a black collar and strapped it around his neck. For a moment, everything felt weird. Hex, Brynn, and Siya joined him with wide eyes. The world was slowly getting bigger. Cass looked at them as they grew taller and taller. Until they were tall enough that he was at eye level with Siya's breasts. He turned around to look at the other two, but they were so tall now that he had to look up past their breasts.

But it wasn't over. Cass's dick began to tingle. He looked down to see his dick get smaller and smaller, inch by inch, until it was just under two inches. That made him realize that the world hadn't grown. Much like his dick, he had been shrunk.

"There you go." Cass turned to find a massive cock pointed right at his face. Not only was he at eye level with Siya's breasts, but he was also at eye level with the demon's cock. "On top of the physical changes, that collar has other effects. You'll learn about those later though."

"By the way, the name's Gwen." She pulled her dick back and let it plop against his face. Not only did it look bigger up close, but it was surprisingly heavy too. After slapping her cock against him a few more times for fun, Gwen moved on to the others. She turned to Hex first, lifting the straps of her dress, and slipping them off her shoulders. Her blue dress fell to the ground, leaving her completely naked too.

"Gods, look at the tits on this one." She grabbed a breast in each hand and gave them a firm squeeze. "Can't believe someone with a rack like this is still a virgin. I'll be sure to fix that tonight."

Next was Brynn, who quickly stripped when Gwen turned to her. She seemed mesmerized by her new lover. As if it took all her energy not to pounce on Gwen and suck her off.

"Looks like someone's eager." Gwen teased. Then she reached down with two fingers to stroke Brynn's pussy. "And already wet for me too."

And last was Siya, the girl Cass had always wanted to be with. She kept her head down and fidgeted with the end of her dress. Occasionally, she'd glance nervously at him.

"No need to feel ashamed," Gwen said soothingly. "It's only natural for you to move on to someone more capable. I can protect you, support you, and fuck you till your mind breaks from pleasure. Things he can only dream of doing to you."

"But...I still love him."

Gwen gently slipped Siya's dress off, one strap at a time, and placed a hand on her cheek. "And that's perfectly fine. You can still be with him, but that nice ass of yours belongs to me. I can already imagine it bouncing as I fuck it all night long."

Siya looked a little relieved, as well as aroused, but she also refused to look him in the eye. She stepped aside as Gwen attached a leash to Cass's collar.

"Since you care about him that much," she handed the leash to Siya, "I'll leave him to you."

She seemed amused by that, pulling on his leash to get him to follow her. It was tight around his neck, but he was thankful it was Siya who had the leash rather than Gwen.

Now done with her teasing, Gwen led them further from the city, with the reigns of their horses and her demonic horse in hand. Apparently, she had set up camp nearby. As they walked, Siya kept glancing down at him.