It's been nearly a year ever since I've been made to join the Mariani family as dumb muscle. Things used to be so different before, but apparently, fate had something else in store for me. I used to have a girlfriend, a steady job, even if it wasn't glorious, I had a place to live in, even if it was small, things were good enough. Then the prohibition came, and everything went to hell. First I was out of a job, and before long, I was out on the street, my girlfriend left me, and I was neck-deep in debt. At that point, there was only one option left for me: The mob. The Mariani family had used the prohibition to further cement its grip on the city—with legal alcohol options wiped out over night, organized crime was ready to pick up the slack. Speakeasies popped up all over town, all either openly or more subtly associated with the Marianis. And so, to escape the loan sharks ready to break my legs, I threw in my lot with the mob to try and get protection from them.
Soon enough, I was in too deep, having pledged my life to the mob with my debts, and now there was no way back. This was my life now. Violence, constant vigilance not to get caught by the law, murder if necessary. But that would change just last week ago, as my superior took me aside and told me that I was being relocated to a very special job: Protecting the Boss's son at a remote seaside mansion. One might think that that job is safer due to the isolated location, but that is not the case for one simple reason: The prince. That is what people call the Boss's son, Arthur, and it's for a reason. Arthur is the next-in-line to the spot of the Boss, and he knows it. Despite his almost frail appearance, the man has inherited every last bit of his father's cold intellect and vicious charisma, with his look only enhancing it through the juxtaposition. And because of his status as the Boss's chosen one, he is treated like absolute royalty, with disobeying the prince being a one-way-ticket to a very, very bad time that you might survive if he is merciful... which he pretty much never is.
So now here I am, reduced to a glorified butler for a man that could have me killed at pretty much any moment, meaning that I am constantly on edge, fearing that every day could be my last. While there are several people here taking care of Arthur and seeing to his every wish, I'm largely in charge of cleaning, the most thankless job. It usually means that I'm wandering throughout the house at most times, constantly at risk of running into the prince and having to do something for him, which brings its own dangers of him finding what I do lacking. Today, I've been lucky so far and haven't seen him yet, a streak which I hope continues as I head towards his bedroom, the one room that I absolutely have to make sure is clean.
Opening the door without much thought, I am suddenly face to face with something I had never even considered to be a possibility before. There he is, the prince of crime, the cut-throat nobility with an icy stare that could freeze your heart with fear in an instant... wearing a dress. My mind short-circuits immediately, incapable of processing the sight before me. His reaction is almost instant, pulling out something from a pocket in his dress that might be a blackjack and striking me three times in a row with absolute precision. Darkness overtakes me right away, and I am out like a light before my body even has the opportunity to hit the floor.
When I come to again, I am tied to a chair and blindfolded, unable to see. As I slowly start struggling against my bonds, a soft, emotionless laugh echoes in my ears. "Don't bother. I know my knots, and you're not getting out of that until I let you, ingrate." The voice I am hearing is Arthur's, but where am I? For a moment, I try to sputter out some sort of apology, but all that gets me is a slap squarely across the face. "Shut up. You're on thin fucking ice right now, and every word that comes out of your stupid mouth is making it worse, so you are going to listen now, understand?" With the taste of blood in my mouth, I nod, and he continues. "You've just seen something none of you goons were ever supposed to see, and I should honestly just have you killed before you talk. I'd do it myself, but it'd stain the rug. However... I have a different idea. So if you treasure your miserable life, you better listen up. Here's how this is going to go. I am giving you a choice: You will either become my personal servant, following me around wherever I go and seeing to every last desire of mine, no matter what... or you take a swim with cement shoes. Take your pick, meathead." His voice is cold, without a shred of that anger that one would expect from someone that just had one of their deepest secrets revealed. In a way, that is to be expected from the prince, but at the same time, the way he phrases this "personal servant" business has me worried. Then again, it's not like I have a choice, because it's either that or death.
After a short moment of silence, I simply reply "I will serve you." with a defeated tone in my voice. Again, he laughs in that emotionless way, and after a short moment, I can feel him removing the blindfold. To my surprise, I find myself still in Arthur's bedroom, and there he stands in front of me, still wearing that dress. Now I can finally get a good look at him, and I would have to lie if I were to say it didn't fit him. It's a modest, long black number that perfectly matches his long black hair and contrasts with his pale skin. If I didn't know better, I could have mistaken him for a woman right then and there.
A smile creeps into his expression, and it's not a welcoming, warm one. It's a vicious, cold one, like a predator that is about to toy with its prey. "Alright, Jack, welcome to your new job. Here's how this is going to go: When I speak, you listen. When I command, you follow. And above all... you don't blab to anybody. If what you've seen here today gets out in any way, I will make sure you regret it for every last minute of what will be the very short remainder of your miserable existence, got it?" A wordless nod is all I can muster as a response, and with another one of those creepy chuckles, he takes a step away, giving me a better look at his entire figure in that dress. "I know you like how I look. Of course you do, I'm the best looking god damn thing your perverted eyes have ever been able to witness. And guess what... you're going to fuck this beautiful thing, right now."
My jaw drops in sheer confusion. "Y-you can't... you c-can't mean..." I stammer, incapable of forming a clear thought.
Meanwhile, he steps behind me, untying the bonds keeping me in the chair. "Oh, I can. I can do anything, my new servant. I can tell you to do anything, and if you don't want to die, you'll do it." he says, a new tone creeping into his voice that has every word dripping with lascivious intent. With my bonds undone, he steps back in front of me before sitting down on his bed and slowly beginning to lift up his dress. "So right now, I am telling you... to fuck my ass. And trust me... I can go for quite some time, so if you don't want to sleep with the fishes, you better sleep with me until I'm satisfied. So get over here, you dumb musclehead, and show me you're at least useful as a fucktoy for me to pleasure myself with."