Chapter 101: Cross-Dressing
Chapter 101: Cross-Dressing
The heat of the Council had yet to cool, and the Commercial District of the Outer Castle was teeming with members of the Demon Race. Merchants, tourists who had come for the festival, and adventurers out for a brief respite—the streets were a sea of diverse faces.
Among the crowds of people passing by, one particular duo stood out.
One was a gentleman with an androgynous charm, standing in the mid-170s—not exceptionally tall, but possessing fine proportions—with shimmering blonde hair.
The other was a girl in a dress, looking incredibly young and cute. Even with high heels, she didn't quite reach 150 centimeters.
They exuded an air of sophistication and grace, looking for all the world like high-ranking nobles of the Demon Race.
In particular, the androgynous gentleman radiated an intimidating pressure, a latent power rarely seen in ordinary demons.
As a result, whenever the two took a step forward, the crowded masses parted to the left and right, carving out a path for them to walk comfortably.
Seeing them dressed so formally that their noble status was unmistakable, onlookers whispered that they must be out for some form of entertainment. Some even speculated that marriage talks might be underway for the girl, whose age was difficult to discern. The two heard every word of these hushed conversations.
"That’s what they’re saying. Since they’ve brought it up, should we just head straight to a wedding hall?"
The gentleman wrapped an arm around the girl’s waist. It wasn't exactly to escort her through the oncoming crowd.
It was a way of sharing body temperature, a gesture meant to soothe the girl, who was visibly stiff with tension. It was a silent message: Don't be nervous. You can walk with more confidence.
Despite understanding the intent, the girl remained unable to relax. And for good reason.
She was deceiving everyone here. She could only imagine what would happen to her the moment she was found out.
The girl whispered to the gentleman in a voice so low it was inaudible to anyone else.
"Can we... go somewhere with fewer people...?"
"Hmm? If we do that, I won't be able to show off how cute you look to everyone."
"I don't need to be shown off...!"
Barely managing to keep her voice from rising, the girl snapped at the gentleman walking beside her. However, his nonchalant, smiling attitude forced her to shut her mouth.
If they got into an argument here, they would draw even more attention, and then it would be discovered—that the person walking through the city in an elegant dress wasn't a girl, but a man.
And that, thanks to the wide skirt of the dress, no one noticed he was extremely aroused, with a cock the size of a forearm standing fully erect.
Furthermore, the one committing this madness was none other than their next Demon Lord. The girl glared at the gentleman with eyes full of resentment. The gentleman’s name was Nero, and the girl’s name was Jaejin.
*
The story goes back to when Jaejin was still mingling with over a dozen Lust Demons. Jaejin had been grabbing the firm buttocks of the prepared Lust Demons one by one, thrusting his long cock into them.
After having fifteen ejaculations squeezed out of him by Lust Demons who gave their all for a single climax, Jaejin was having a late lunch.
Having done a great deal of work since morning, the rest and the meal tasted like heaven to the famished Jaejin.
It was then that Nero, whom he was scheduled to meet a bit later, came to find him.
It had been a while since he last saw her, the last time being when she and Lena had squeezed him dry together a few days ago. He had heard that she had been frequenting the taverns in the city lately.
"A tavern? Ah, Isaac's Garden? I've been there a lot recently. It’s a very noisy and fun place, probably because so many adventurers stop by. Quite a few humans visit, too."
Perhaps she had been bored, as she sat across from Jaejin, who hadn't finished his meal yet, and began to chatter away.
She talked about going down to the city to find the Adventurer's Guild, being mistaken for a novice mage there, and even ending up going out to subjugate monsters on a whim.
Most of it felt like a dragon’s "commoner experience" diary born out of boredom, but since she was genuinely enjoying rubbing shoulders with people, Jaejin found himself getting swept up in her excitement.
"So, Jaejin. There’s something I want to try♡"
"Hmm? Something you want to try? If it’s something you want to do, Nero... sure, let’s do it."
If it was something as fun as the stories she had just told, he had no reason to refuse. Thus, Jaejin readily nodded.
However, Jaejin had overlooked something at that moment. He forgot how selfish and troublesome this hedonistic dragon could be, and how much her innocent, malice-free purity could embarrass a person.
Jaejin would soon regret his complacency—the fact that he hadn't felt a sense of crisis even after being squeezed until he fainted by that very purity.
Nero took Jaejin to a costume shop within the castle. It was a place primarily used by high-ranking demons, nobles, and high-level demons, operated by the Three-Eyed Tribe, who were renowned for their aesthetic sense.
After exchanging a few words with the designer to commission the clothes, Nero looked at Jaejin with a beaming smile.
"Did you know that even in places you always pass by, the feeling of walking through them changes depending on what you're wearing? This time is going to be incredibly fun."
Her request was simple. Since today’s milking could be finished quickly, she wanted to walk around the city together. Jaejin had no particular reason to refuse the suggestion of just dressing up and going out.
In fact, for Jaejin, who had spent a dense milking session from morning until lunch, a break to catch his breath was exactly what he needed, and Nero’s proposal was quite welcome.
"So, what kind of clothes did you order?"
"Ah, a butler outfit and a dress. I thought it wouldn't be bad to walk around pretending to be nobles for once. They say the more experiences, the better, right?"
A butler outfit brought to mind a neat suit, sleeves tidied with cufflinks, and a monocle, but Jaejin was unsure how well that would suit him.
It required good body proportions and, above all, height to pull off. It was an outfit that would look great on someone with a build like Nero’s.
On the other hand, imagining Nero in a dress made his heart flutter. Given her exceptional beauty, she would surely look like an angel in either a simple or a lavish dress.
While they were talking, the designer came out with clothes that fit the two of them: a butler suit and a very cute-looking dress.
"Wait? This looks way too big for me to wear, doesn't it? And isn't the dress too small for you, Nero?"
The problem was that the outfits didn't seem to account for their builds. At this rate, the clothes would be too baggy to walk in properly. Nero’s dress also seemed to be the wrong size for her.
"No, they’re exactly right."
"What do you mean, right? It seems more like you should wear the butler suit and I should wear the... dress...?"
Jaejin stopped mid-sentence as he realized something had gone terribly wrong. Nero looked down at the frozen Jaejin with a silly, grinning face. For some reason, that smile seemed to reek of mischief.
"Exactly. See? This dress fits Jaejin’s body perfectly, doesn't it?"
Nero held the dress up against Jaejin’s body. It had been tailored perfectly to him, likely the result of the Three-Eyed Tribe’s unique physical analysis, but the fact that it was a dress was far more important than the impressive skill involved.
"I-I'm a man, though?"
"Gender doesn't matter when it comes to wearing a dress♡ What matters is how well the clothes suit you♡"
Nero was purely insane. Her purity, which could only be described as madness, was not bound by fixed common sense; she simply chased the pleasure she could see and feel.
While that was part of her charm, it was currently a source of horror for Jaejin. Having a sophisticated yet cute, girlish dress thrust upon him was a scenario he had never experienced before.
"I can't wear this...! How do you expect me to wear this...!!"
"No, it’s just that you don't know your own charm. It’s going to look amazing on you... Ehehe."
She was being devious. Her smile and laughter were so sinister they gave him goosebumps. He tried to run away, but against a polymorphed dragon, all a frail human male could do was struggle as his arms were pinned.
"I won't do anything bad... Hehe, come here...!"
In the end, with the designer’s help, Jaejin was stripped in an instant. After his body was wiped down with a towel, he was slowly dressed in the gown from the top down.
With a wig that felt like real hair, a young girl with straight black hair tied in a half-updo was completed.
If there was any consolation, it was that he was still wearing male underwear. But even that provided no comfort when he saw his reflection in the mirror.
A girl so cute that no one would suspect she was a man, even from up close, stood there. Meanwhile, next to him, a terrifyingly handsome woman dressed as a man was adjusting her outfit.
"Wow, there’s probably hardly any girl who suits a dress this well♡"
Jaejin wanted to snap back at Nero’s words, which didn't sound like a compliment at all, but he was so preoccupied by the awkward sensation of emptiness in his lower half that he couldn't even grumble.
"Wearing something like this... it’s just uncomfortable..."
"But it’s incredibly cute♡ Everyone passing by will probably stare. They’ll wonder if such a cute girl always lived here♡"
Hearing that didn't make him happy at all. To Jaejin, a man, it was essentially saying he didn't look manly, so it didn't fall under the category of a compliment.
Nero hugged the sulking Jaejin from behind. Since she hadn't polymorphed into a man but was simply a woman cross-dressing, the sensation of her breasts could be felt against his back.
"And you know, you’re turned on, aren't you? Did you think I wouldn't notice you’ve had an erection ever since you put those clothes on?"
"...!?"
She had known all along that his erection hadn't subsided since the moment he put on the dress. Since when? How? Jaejin turned around in shock, and the answer was immediately clear.
A dragon with blonde hair and golden eyes. Though she was an eccentric, there was nothing in the world that could escape her gaze.
"Now, imagine it. The gazes that will be on you as you walk around outside for the next half-day. Every time that happens, your excited, erect dick won't be able to properly release that sexual desire, leaving you in a state of frustration."
Nero began to caress Jaejin’s chest through the fabric. The stimulation through the cloth was very faint, but for the already aroused Jaejin, even that felt like a massive surge of sensation.
"And then, I’ll slowly pleasure the dick that’s been simmering for hours. I’ll tease your sensitive, burning cock, touching only the spots you like, very slowly.
I’m planning to fuck you until deep into the night, with that frustrated dick inside my pussy, while you’re still wearing those very clothes. What do you think?"
Such an absurd proposal. He should have refused. But the more he listened to Nero’s words, and the more his chest was caressed by her fingers, the more impossible it became to want to say no.
Jaejin, who felt like he might climax just from the stimulation of his chest and her description, looked at Nero with a desperate face as she stopped the stimulation and waited for his answer.
"I... I’ll do it... I’ll do it, so... you have to make me feel good, okay...?"
Nero looked at Jaejin, who had finally succumbed to desire and accepted the cross-dressing, with devious eyes. She quietly licked her lips and led Jaejin outside.