• Scenarios
  • Tags
  • Sign in
PopularTags
write34
Sign in
Site Content
TagsSearchUpload PromptJoin us on Discord!
Social
Roguish Charm... And A Dress

Prompt originally from AetherRoom.club
Created: 2023-08-30
No ratings yet
Description
Nobles are strange, and so are their courtship rituals, but the kingdom of Isteria takes this a step further. Every year, there is a courtship festival in the capital city of Caershire, where high class bachelors and bachelorettes are the targets of various would-be partners competing in various events, be it sports, cooking, singing... you name it, there's a competition for it at the courtship festival, with the hand of a noble the prize. The event culminates in the Grand Tournament, where the most coveted bachelor is on offer. And I, a male rogue that is seeking a way out of my life of crime, am trying to win this tournament. All I need is a dress, some gumption, and a little luck.
Tags
yaoi, gay, first person, medieval, knight, courtship, contest, femboy, crossdressing, bizarre contests and game shows friday
Prompt
Today is the day. Today is the day that my plan will be put into action, and I will either succeed or fail. It's a bit of a relief, knowing that by the time the sun sets, this will be done and I'll either have made it or not, but this is very much the biggest scheme I've ever plotted, with possible results ranging from a life of riches to the death penalty if I get particularly unlucky. Not that I figure my life will be ruined over this. If I do get caught out, I assume the most likely result is that I flee the scene and make residence far away for a while; I've planned things out quite far in that regard. Being a rogue that makes his life's work through petty crime is ultimately a dangerous game, even if I've gotten quite good at avoiding consequences, and I've always been looking out for that one big score that gets me into a stable, safe life. And I think I've found it. Now, courtship for nobility is a very strange thing everywhere in the world, but I feel like Isteria takes it further than most. There is surely some line in an ancient text that people would point to in an attempt to explain how we got to this point, but this would probably only be a tenuous, vague link. There is no possible explanation that explains things like the courtship festival in a satisfactory manner. This was simply some idea of some king back in the past and inertia has brought us here, where every year, at the height of summer, single nobles and courtiers flock to the royal castle to engage in various events, including athletic competitions, artistic performances, culinary presentations, and much more. And it is all fiercely, desperately competitive, all driven by a need to upstage whoever you are competing against in a bid to impress knights and nobles seeking to find their partner. Furthermore, while a lot of realms' nobles sequester themselves away when it comes to these admittedly intimate matters, Isteria could not be more different. No, here, peasants from all across the country are allowed, nay, encouraged to loiter around the castle, viewing the proceedings. Performing under the pressure of an audience is practically required here. And no part of this is more famous, more eventful, than the Grand Tournament. Held in the king's gardens and viewed by thousands of commoners, a small set of hopefuls compete for the affection of the biggest catch of the year, whoever that may be. Usually, it's a famous celebrity, a prince, bard, or something like that, and this year is no different, with the grand prize being Sir Joyce of Herethford, a rising star in the kingdom that has become the catch of catches. This is my ticket out. While my feminine appearance has been helpful in wooing marks and making swindles work, this is where I can make a big splash. If I win this; if I manage to swindle myself into a marriage, I'm set for life. He already has a castle of his own in the countryside, and is only going to get richer over time. It helps that he is really, really pretty too, so I wouldn't even have to be playing a role to be a loving wife, well, apart from being a guy and all, so I'd still have to be playing the role of a woman. Carrying my backpack, I make my way towards the castle—seamlessly blending in with the other commoners, as is my bread and butter. With today being the day of the Grand Tournament, crowds are out in force, and that makes my sneaking all the more effective. Inside, many events are already running, with many peasants watching noblewomen dancing on one side, noblemen cooking on another, and I think I can hear the sounds of a servant announcing the beginning of an archery contest in one of the minor gardens outside. So with so many things to watch, it makes it quite easy for me to slip away into a side hallway and unlock a door with a key I managed to acquire from a stablehand in exchange for a couple of mugs of ale in coin. This allows me access to the lower bedchambers, which are deserted right now, with every single servant busy trying to keep this event running. The noise immediately quiets down as the heavy door falls shut behind me, and after trying a few of the smaller doors here, I find one that is unlocked and let myself in. Here, in this modest bedchamber, I can finally put my plan into action, and I unpack my backpack, which contains two important things. First, women's clothing—a dress, appropriate shoes, and some fairly simple gloves. This isn't the most amazing stuff, and it would probably look out of place if every competitor was a true noblewoman, but smaller, poorer families that own a bit of land and have tangential contact with the elite still get their shots, so I should be able to pass as one of them fairly well. I slip off my regular clothes and slide into the dress, packing the other stuff into a nearby cupboard—if things go well, I won't need them anymore, and if things go badly, I won't be able to retrieve them anymore. Looking down at myself, I hope that I look good enough to pass as a woman. I had some people tell me I look like a woman and have used my girly looks for profit, but I have never actually tried to make others believe I am a woman. I am confident in my abilities, but still, the first time can be difficult. But the second thing I have is the more important one: a faked invitation for "Galeria", the firstborn daughter of a small landlord and farmer of modest wealth that lives in the countryside and also doesn't actually exist. This is my masterwork, a forgery that I put my all into, and I clutch it closely to myself as I exit the quiet side chambers and rejoin the crowds, making sure not to arouse any suspicion. Now all that's left is entering the competition and winning it. My heart is pounding as I walk along the main halls towards the exit to the large central gardens where the Grand Tournament will be taking place. When a guard stops me and tells me only competitors are allowed here at this time, I hand him the envelope, trying my damndest to not let the nervousness show, and breathe a silent sigh of relief when he nods and motions me to enter. Thankfully, experience has told me that the right hand doesn't know what the left is doing here, so there's not a central list of competitors, one can just show up with an invitation. While I had heard of the king's gardens before, seeing them for the first time is really something special. They are absolutely beautiful, but I have no time to smell the roses, because there is a tournament to be won. It doesn't take long before the crowds begin to file in as well, filling up the seating areas set up all around a central grassy plot, and I find myself alongside about a dozen other hopeful women, and it seems my disguise is capable enough of fooling even them, as nobody seems perturbed by my presence. And as I wait, I see my target arriving at the premium seating with the best view of the plot—Sir Joyce—and gods, he is stunning. A youthful face so inappropriate for a veteran knight, and a smile that could charm the undergarments off women even better than mine. Why, I could very much see myself snuggling up to him in bed... er, what am I thinking? This is no time to swoon. And then, the murmuring of the crowd slowly dies down through the signal of several servants, and one steps forward and begins bellowing, "Hear ye, hear ye, we have assembled for the Grand Tournament here in the king's gardens! A small group of fair maidens will be competing for the affection of Sir Joyce of Herethford, the conqueror of Isteria's foes!" He pauses for a moment to allow the crowd to cheer and Sir Joyce to make a few polite nods and gestures of acknowledgement. "As you all know, these maidens will compete in multiple events, and your approval will help determine the winner," he continues. Right, this is, in a way, a popularity contest rather than the more direct decisions made by the bachelor or bachelorette in the side events. Playing the crowd is a big part here, and I can imagine my rogue's background and ability to make people like me being an advantage here. Finally, it was time to begin. "The rounds will be as follows. The first round will be the garden race, a footrace through the entirety of the king's gardens and a test of dexterity, but also of grace. The second round will be, of course, as you know and love, the bare-knuckle fistfight melee, where knocked-out competitors are eliminated. And finally, the third round and decider will be the tavern chant performance, where each remaining maiden will perform the lewdest, bawdiest song they know for Sir Joyce and the crowd. So, if the maidens would take their place at the starting line..." he trails off. We take our place, and this is going to be strange. I did not figure having to run a race in this darned dress into my plan, but I'm sure I'm capable of outclassing these dainty women regardless. Another servant counts down from three, and with one final yell, we're off.... [Click to expand]
Today is the day. Today is the day that my plan will be put into action, and I will either succeed or fail. It's a bit of a relief, knowing that by the time the sun sets, this will be done and I'll either have made it or not, but this is very much the biggest scheme I've ever plotted, with possible results ranging from a life of riches to the death penalty if I get particularly unlucky. Not that I figure my life will be ruined over this. If I do get caught out, I assume the most likely result is that I flee the scene and make residence far away for a while; I've planned things out quite far in that regard. Being a rogue that makes his life's work through petty crime is ultimately a dangerous game, even if I've gotten quite good at avoiding consequences, and I've always been looking out for that one big score that gets me into a stable, safe life. And I think I've found it.
Now, courtship for nobility is a very strange thing everywhere in the world, but I feel like Isteria takes it further than most. There is surely some line in an ancient text that people would point to in an attempt to explain how we got to this point, but this would probably only be a tenuous, vague link. There is no possible explanation that explains things like the courtship festival in a satisfactory manner. This was simply some idea of some king back in the past and inertia has brought us here, where every year, at the height of summer, single nobles and courtiers flock to the royal castle to engage in various events, including athletic competitions, artistic performances, culinary presentations, and much more. And it is all fiercely, desperately competitive, all driven by a need to upstage whoever you are competing against in a bid to impress knights and nobles seeking to find their partner. Furthermore, while a lot of realms' nobles sequester themselves away when it comes to these admittedly intimate matters, Isteria could not be more different. No, here, peasants from all across the country are allowed, nay, encouraged to loiter around the castle, viewing the proceedings. Performing under the pressure of an audience is practically required here.
And no part of this is more famous, more eventful, than the Grand Tournament. Held in the king's gardens and viewed by thousands of commoners, a small set of hopefuls compete for the affection of the biggest catch of the year, whoever that may be. Usually, it's a famous celebrity, a prince, bard, or something like that, and this year is no different, with the grand prize being Sir Joyce of Herethford, a rising star in the kingdom that has become the catch of catches. This is my ticket out. While my feminine appearance has been helpful in wooing marks and making swindles work, this is where I can make a big splash. If I win this; if I manage to swindle myself into a marriage, I'm set for life. He already has a castle of his own in the countryside, and is only going to get richer over time. It helps that he is really, really pretty too, so I wouldn't even have to be playing a role to be a loving wife, well, apart from being a guy and all, so I'd still have to be playing the role of a woman.
Carrying my backpack, I make my way towards the castle—seamlessly blending in with the other commoners, as is my bread and butter. With today being the day of the Grand Tournament, crowds are out in force, and that makes my sneaking all the more effective. Inside, many events are already running, with many peasants watching noblewomen dancing on one side, noblemen cooking on another, and I think I can hear the sounds of a servant announcing the beginning of an archery contest in one of the minor gardens outside. So with so many things to watch, it makes it quite easy for me to slip away into a side hallway and unlock a door with a key I managed to acquire from a stablehand in exchange for a couple of mugs of ale in coin. This allows me access to the lower bedchambers, which are deserted right now, with every single servant busy trying to keep this event running.
The noise immediately quiets down as the heavy door falls shut behind me, and after trying a few of the smaller doors here, I find one that is unlocked and let myself in. Here, in this modest bedchamber, I can finally put my plan into action, and I unpack my backpack, which contains two important things. First, women's clothing—a dress, appropriate shoes, and some fairly simple gloves. This isn't the most amazing stuff, and it would probably look out of place if every competitor was a true noblewoman, but smaller, poorer families that own a bit of land and have tangential contact with the elite still get their shots, so I should be able to pass as one of them fairly well. I slip off my regular clothes and slide into the dress, packing the other stuff into a nearby cupboard—if things go well, I won't need them anymore, and if things go badly, I won't be able to retrieve them anymore. Looking down at myself, I hope that I look good enough to pass as a woman. I had some people tell me I look like a woman and have used my girly looks for profit, but I have never actually tried to make others believe I am a woman. I am confident in my abilities, but still, the first time can be difficult.
But the second thing I have is the more important one: a faked invitation for "Galeria", the firstborn daughter of a small landlord and farmer of modest wealth that lives in the countryside and also doesn't actually exist. This is my masterwork, a forgery that I put my all into, and I clutch it closely to myself as I exit the quiet side chambers and rejoin the crowds, making sure not to arouse any suspicion. Now all that's left is entering the competition and winning it. My heart is pounding as I walk along the main halls towards the exit to the large central gardens where the Grand Tournament will be taking place. When a guard stops me and tells me only competitors are allowed here at this time, I hand him the envelope, trying my damndest to not let the nervousness show, and breathe a silent sigh of relief when he nods and motions me to enter. Thankfully, experience has told me that the right hand doesn't know what the left is doing here, so there's not a central list of competitors, one can just show up with an invitation.
While I had heard of the king's gardens before, seeing them for the first time is really something special. They are absolutely beautiful, but I have no time to smell the roses, because there is a tournament to be won. It doesn't take long before the crowds begin to file in as well, filling up the seating areas set up all around a central grassy plot, and I find myself alongside about a dozen other hopeful women, and it seems my disguise is capable enough of fooling even them, as nobody seems perturbed by my presence. And as I wait, I see my target arriving at the premium seating with the best view of the plot—Sir Joyce—and gods, he is stunning. A youthful face so inappropriate for a veteran knight, and a smile that could charm the undergarments off women even better than mine. Why, I could very much see myself snuggling up to him in bed... er, what am I thinking? This is no time to swoon.
And then, the murmuring of the crowd slowly dies down through the signal of several servants, and one steps forward and begins bellowing, "Hear ye, hear ye, we have assembled for the Grand Tournament here in the king's gardens! A small group of fair maidens will be competing for the affection of Sir Joyce of Herethford, the conqueror of Isteria's foes!" He pauses for a moment to allow the crowd to cheer and Sir Joyce to make a few polite nods and gestures of acknowledgement. "As you all know, these maidens will compete in multiple events, and your approval will help determine the winner," he continues. Right, this is, in a way, a popularity contest rather than the more direct decisions made by the bachelor or bachelorette in the side events. Playing the crowd is a big part here, and I can imagine my rogue's background and ability to make people like me being an advantage here. Finally, it was time to begin. "The rounds will be as follows. The first round will be the garden race, a footrace through the entirety of the king's gardens and a test of dexterity, but also of grace. The second round will be, of course, as you know and love, the bare-knuckle fistfight melee, where knocked-out competitors are eliminated. And finally, the third round and decider will be the tavern chant performance, where each remaining maiden will perform the lewdest, bawdiest song they know for Sir Joyce and the crowd. So, if the maidens would take their place at the starting line..." he trails off.
We take our place, and this is going to be strange. I did not figure having to run a race in this darned dress into my plan, but I'm sure I'm capable of outclassing these dainty women regardless. Another servant counts down from three, and with one final yell, we're off.
Memory
I am Giles, a young man that earns his keep in the medieval kingdom of Isteria as a rogue of sorts, doing odd jobs, engaging in petty crime, and swindling people out of their coin with a kind word and a smile. It's not a glamorous life, but it is a life that I have so far been able to sustain and even amass a little stash of wealth with. Helping me with that are my rather feminine looks, with a soft face and long hair making me appear more approachable and less dangerous, which makes it easier for me to club them over the back of their head in a dark alley and rob them. In addition, I've become accustomed to teasing and toying with men to get them into a vulnerable position that leaves them more easily exploitable for my purposes. However, in doing so, I have developed a genuine desire for other men that I have indulged in at times without an ulterior motive, just for passion's sake. In this endeavor, I have taken on the moniker of Galeria, a small-time noblewoman from a modestly wealthy countryside family.
World Info
View World Info
  • Joyce, Herethford

    Sir Joyce of Herethford is a young man that has quickly become a particularly famous knight in Isteria, his renown growing through valiant performances in serving our king in recent campaigns of conquest and expansion. He is also quite beautiful, having a boyish, youthful charm that belies his martial prowess, and is known for being a kind and gentle soul in private as well. This has made him the kingdom's most sought-after bachelor and the target of noblewomen the realm over. And, well, he has not just caught the eyes of women, but some men as well, and that includes me. Ever since I saw him in a victory parade through the capital of Caershire and read the announcement of this year's courtship festival's Grand Tournament being the search for his bride-to-be, I have become infatuated with the idea of becoming his wife through subterfuge and crossdressing, seeing it as my ticket out of my life of crime. Am I in love with him? Well... maybe. Maybe I'm seeing a bit more than just a get-rich scheme in his pretty face with those lips I catch myself dreaming of kissing one day.
Download Count: 3