After several years, you meet up with a man who you had gay sex with after a casual encounter on Craigslist. When that guy pulls up and tells you he has a job for you, you say yes. Is it most likely illegal? Absolutely. Do you care? Not at all. Things aren't exactly pretty here in the lower income parts of Chicago, and when you're looking for where your next meal is going to come from, your standards for what exactly constitutes acceptable work aren't high. That's why I'm now on my way to my new job as a live-in servant in the rich folks' district, which promised to be low on back-breaking labor and high enough on pay, and that's just a combination that I couldn't resist, even if I have to admit that there's a part of me that thinks this is too good to be true. But like I said, I'm not exactly in a situation where I can be picky, so when an older guy wearing an ill-fitting suit picked me out on the street, engaged in a short conversation with me, then made me a job offer, I answered "When can I start?", and the answer to that was today.
The wealthier parts of Chicago are quite something to behold when you're poor—like I am. In some way, it's like stepping into a different world entirely. Houses are actually appealing to look at, and hell, they're actually houses, made to house a single family, not huge tenements that poor people crowd into. Just walking around, I feel out of place here, but of course, that's not true. People like me are very much at home in this part of town, because after all, the rich need their servants. After a bit of searching, I end up finding the place: a rather posh house that might be better described as a mansion. It looks like it's got plenty of room for people like me to stay rather than head home at the end of the work day, though that does mean that since I'm a live-in servant, I'm even more reliant on my boss. I suppose all I can do is hope I'm lucky.
I do have good reason to believe I got a break with this job, because I'm working for the Wilsons, a family of two—an older widowed man and his grown-up son—who used to be farmers out in the countryside until a rich oil well was discovered on their land, which the old man managed to leverage into a big payment as well as a job with the oil company that gives him a large, stable income. So I'm banking on this being a situation where you take the man out of the country, but can't take the country out of the man, and the two don't have the trappings of the usual snobby rich. Knocking at the door, I'm soon let in by one of the other servants that were hired earlier and brought inside. But while there are people here that move things around, clean, cook, and all those usual things, my job description is something else.
With the old man of the house frequently being out because of business travel for his job, he wanted someone to take care of his son, Arthur. Well, "take care" is a bit much, it's not like he can't take care of himself; he's an adult, after all. But at the same time, Arthur is a country boy through and through, and he is just not ready for life in the city. So while the other employees here have specific tasks, mine is simply to accompany Arthur and show him the ways of the city. Because of their wealth, he doesn't have a job himself, and part of my task might even be to just help him pass the time with whatever activities come to mind. It's certainly no job I've done before, so it might be a bit strange, but then again, this job probably has the least chance of grievous injury out of all I've worked so far.
So I'm brought to a study of sorts, where a young man is standing in front of a large desk, a map of Chicago spread out in front of him, and the servant that accompanied me announces, "Sir, your partner is here," then leaves. Partner? That's a bit of a loaded term, isn't it? Then again, looking at the guy, it's not like he's unattractive or anything like that—in fact, he's kind of cute.
The young man, who I presume to be Arthur, turns to face me, a big grin on his face. "Howdy! Pa told me you were gonna be along. So you're Roy, right? Gonna show me 'round this town and what kinda stuff you city folks do for fun?" he asks. It's very obvious he's rural as can be just from listening to him, and when I nod, he quickly extends his hand for a shake, which I accept. "Real nice to meet you, Roy. I've been lookin' this here map over a bit, but I ain't got the first idea where to start, so if you got any suggestions, I'm really wanting to turn you into a sissy maid and fuck you .