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Dress For The Job

Prompt originally from AetherRoom.club
Created: 2023-11-16
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Description
Sometimes, the job market isn't exactly brimming with options. That is the kind of situation where both you and your roommate find yourselves taking a job at a lower tier theme park. But while you end up doing the fairly mundane job of taking tickets, your roommate finds himself playing the role of a princess, with the dress, wig, and everything else. But when the two of you end up back home, still in work clothes... man, why does he look so cute in that dress?
Tags
yaoi, gay, first person, princess, crossdressing
Prompt
Phew, what a first day at work. Who knew that not having a clear job description would come back to bite me in the ass just about immediately? Here I thought that I'd just be sitting in a booth, taking some people's tickets and letting them in, but no. Since this place isn't exactly hauling in the crowds, the ticket booths are frequently quiet, but that doesn't mean you can rest, oh no. No, then the ticket takers effectively become some sort of free workforce that is used wherever the boss wants to use them. Whether that's restocking food stalls, mopping the toilets, or whatever else needs doing. You might even find yourself staffing one of the carnival games. Teach me to not read the contract, but hey, it probably could be worse. For one, I could be stuck with Stuart's job. While he has a more defined job description, what that entails was still a bit of a surprise to him. Starting out, he was only told that he was going to play a mascot character for the park, walking around, interacting with guests, that sort of stuff. He thought that that would mean something like playing a knight, or a prince, something like that. Well, as an irritated text message told me just as I was setting up in my booth, the role they had chosen for him was, in fact, that of the princess. He sent me a picture of the pink dress and everything. Apparently, they couldn't get any actual women on staff due to some leery behavior on the part of the boss causing some issues during the job interviews, so some guy was going to get stuck in the dress. At least he's probably a pretty decent pick for it, since he does have a bit of a girly appearance. As I slump down on the couch back at the apartment, I can't even muster up the energy to change out of the work uniform. Seems like these guys are massive cheapskates, because they made us put down a deposit for the uniform and require us to take care of it ourselves, washing it and such. Honestly, these guys can consider themselves incredibly lucky the job market is such crap, because if people had a real choice here, they wouldn't be working at fucking Medieval Land, that's for sure. And while I sit there, the door opens, and in steps Stuart. I'm not looking at him yet, I'm slumped over backwards and staring at the ceiling, but I can tell it's him from his voice, cussing under his breath. I can hear him fall into the armchair and take a big breath as well. "God damn, that shit sucked. At least nobody seemed to notice I was a dude, or if they did, they were polite enough to not tell me to my fucking face," he complains. Actually, thinking about it, I haven't even seen him in that dress yet, I was always in other parts of the park. Wait, if I have to take my uniform home... Summoning up some of my last remaining energy, I sit up straight and look at him. Sure enough, they made him take home the dress, he's still wearing it, and, uh, it's throwing up a lot of questions that I don't want to think about right now. "H-Huh... you, uh, didn't c-change there...?" I mutter, thrown off by the sight. "They made me change in my damn car, Paul. I might as well just fucking drive home in the dress and get into costume at home the next day from now on, because I ain't going through that shit again," he explains, but all the while, I'm still kinda stunned. Even though the dress is clearly low quality and the long blonde wig is some sort of old stock from an ancient theater or something, I can't deny... he's pulling it off. Whereas under normal conditions, he just kind of has a babyface, this crossdressing getup is turning that into a weirdly dignified, soft look. The blonde wig cascading down his shoulders, the dress covering up the lack of feminine features on his body, something about it just works. "I must look like a fucking idiot in this," he adds, and I feel the need to interject. With a sudden burst of enthusiasm, I say, "Well, I think you look really pretty in it." And the moment the words leave my mouth, I clasp my hands in front of my mouth, shocked that I actually said it. A massive blush rises to Stuart's cheeks, and he's just as shocked as I am. "What... what did you just say?" he asks, but while I'm terrified he's pissed at me now... it doesn't seem like it.... [Click to expand]
Phew, what a first day at work. Who knew that not having a clear job description would come back to bite me in the ass just about immediately? Here I thought that I'd just be sitting in a booth, taking some people's tickets and letting them in, but no. Since this place isn't exactly hauling in the crowds, the ticket booths are frequently quiet, but that doesn't mean you can rest, oh no. No, then the ticket takers effectively become some sort of free workforce that is used wherever the boss wants to use them. Whether that's restocking food stalls, mopping the toilets, or whatever else needs doing. You might even find yourself staffing one of the carnival games. Teach me to not read the contract, but hey, it probably could be worse.
For one, I could be stuck with Stuart's job. While he has a more defined job description, what that entails was still a bit of a surprise to him. Starting out, he was only told that he was going to play a mascot character for the park, walking around, interacting with guests, that sort of stuff. He thought that that would mean something like playing a knight, or a prince, something like that. Well, as an irritated text message told me just as I was setting up in my booth, the role they had chosen for him was, in fact, that of the princess. He sent me a picture of the pink dress and everything. Apparently, they couldn't get any actual women on staff due to some leery behavior on the part of the boss causing some issues during the job interviews, so some guy was going to get stuck in the dress. At least he's probably a pretty decent pick for it, since he does have a bit of a girly appearance.
As I slump down on the couch back at the apartment, I can't even muster up the energy to change out of the work uniform. Seems like these guys are massive cheapskates, because they made us put down a deposit for the uniform and require us to take care of it ourselves, washing it and such. Honestly, these guys can consider themselves incredibly lucky the job market is such crap, because if people had a real choice here, they wouldn't be working at fucking Medieval Land, that's for sure.
And while I sit there, the door opens, and in steps Stuart. I'm not looking at him yet, I'm slumped over backwards and staring at the ceiling, but I can tell it's him from his voice, cussing under his breath. I can hear him fall into the armchair and take a big breath as well. "God damn, that shit sucked. At least nobody seemed to notice I was a dude, or if they did, they were polite enough to not tell me to my fucking face," he complains. Actually, thinking about it, I haven't even seen him in that dress yet, I was always in other parts of the park. Wait, if I have to take my uniform home...
Summoning up some of my last remaining energy, I sit up straight and look at him. Sure enough, they made him take home the dress, he's still wearing it, and, uh, it's throwing up a lot of questions that I don't want to think about right now. "H-Huh... you, uh, didn't c-change there...?" I mutter, thrown off by the sight.
"They made me change in my damn car, Paul. I might as well just fucking drive home in the dress and get into costume at home the next day from now on, because I ain't going through that shit again," he explains, but all the while, I'm still kinda stunned. Even though the dress is clearly low quality and the long blonde wig is some sort of old stock from an ancient theater or something, I can't deny... he's pulling it off. Whereas under normal conditions, he just kind of has a babyface, this crossdressing getup is turning that into a weirdly dignified, soft look. The blonde wig cascading down his shoulders, the dress covering up the lack of feminine features on his body, something about it just works. "I must look like a fucking idiot in this," he adds, and I feel the need to interject.
With a sudden burst of enthusiasm, I say, "Well, I think you look really pretty in it." And the moment the words leave my mouth, I clasp my hands in front of my mouth, shocked that I actually said it. A massive blush rises to Stuart's cheeks, and he's just as shocked as I am.
"What... what did you just say?" he asks, but while I'm terrified he's pissed at me now... it doesn't seem like it.
Memory
My name is Paul, and I'm a young man working as a ticket taker down at Medieval Land, a low-quality theme park that recently opened near the town I live in. It's not a quality job, but it is a job—at least as long as this crappy park can keep going before government inspection shuts it down or whatever. While it doesn't make me a lot of money, it's enough to live comfortably enough in the little apartment I share with Stuart. That arrangement does have a few limitations we have to live with, like having to share the same bed. Limitations that seem to have led to there being some sort of odd tension between us where we're not quite sure how we see each other. At least, I'm not quite sure if I see him as just a friend or something more...
World Info
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  • Stuart

    My roommate, Stuart, is a bit of a down on his luck type. Not for lack of trying, mind, he's absolutely been busting his ass trying to get a job, but the results just haven't been there up to this point. Well, now he's actually found a job, even if that job is a quite unorthodox one. To be specific, on the outskirts of our crappy little town, a crappy little theme park that is simply named Medieval Land has recently opened its gates, and it has been struggling to find employees. Because of that, they've had to get creative, which leads to things like Stuart being hired for the job of playing one of the mascots, a princess. Yes, he's a guy playing a princess, and yes, he has to wear a dress and a wig. It does help that he has a bit of a babyface, which gives him something of a feminine look capable of passing as a woman at a glance. Apparently, that's good enough for Medieval Land.
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