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I get a feel for the scene you are establishing. I like the difference in power between the two people, with an implication of danger. With some tweaking, I’d read on.

Point-of-View (POV) problems. You are inside the POV character’s head (“thought the stranger”) but he thinks of himself as the stranger? He should use his own name, or you should get inside the head of whoever would think of him as “the stranger”. If you want to narrate from a distant POV, then why call him “the stranger” at all? The narrator would not have a context for recognizing some characters and not others. I’m also a little confused at points about who is who.

If you are in the stranger’s POV, then it is a slight POV violation for him to seem like he knows why the other guy is doing something (when he received no reply; encouraging a response).

Too much repetition: man in the alley, walkway, mask, face. Is the walkway a sidewalk or an overhead structure? Maybe no one else is bothered; see what others say.

My suggestions [to cut] and to insert or change; some of my suggestions to cut are because there is extra info that does not add anything.

The man in the alley said, “The one you seek is at the Witching Hour.”
John scowled behind his cloth face mask. He stood on the walkway arching over the adjoining street, [the stranger stood listening, adjusting a hat over the cloth face mask], the hem of his heavy cloak moving in the sluggish breeze. After a long pause, the man in the alley took a step forward out of the shadows [when he received no reply]. Faint light from the empty street outlined the wretched planes of his face. Not a trustworthy face, thought John. But nobody would be trustworthy, not here.

“Well? Do you want to know the way or not?” the man hissed from below. [, encouraging an answer from the silent figure standing on the walkway,] “Well?”

I think you'd do well to decide who is telling me this story, presumably it's someone who doesn't know about the demon and that's your twist. Once you know who's eyes we are seeing the story from the POV and names should calm down.

The simple truth is even if we don't know a gender, in our head we'll insert one - usually "he." That's why dogs are often called "good boy" whether or not they are boys.

The demon's not going to think of himself as the "stanger." He/she/it is going to call him/her/itself "Bob." Us labels that fit the POV.

Because you are withholding, I'm not hooked. Tell me. Really, you'll hook me. If the demon is there on a specific errand, let me know. Let me hear him ask the question "Where's Friar Tuck?" before the man in the alley answers.

Good luck

If you must surprise us with a gender switch, tell it from other perspectives (the guy in the alley, someone at the Witching Hour, etc.). Or have the character act and think like a guy because he's gone into really deep cover, playing the part to thoroughly hide her gender. BUT if you do that, you have to be very careful; you are liable to lose the reader's trust.

The POV character is the stranger in the mask. He gets directions from the man in the alley. Then he enters the Witching Hour and converses with another man. Finally he goes upstairs to sell his soul to the demon.

My dilemma: the story is a mystery in the guise of an epic fantasy. The mystery person could be either male or female, my plot is useless if the reader knows who the character is.

There must be a way I can keep it gender inspecific and maintain my mystery!!! This is a problem that has to have a solution that does not cheat the reader.

Can I get away with making the chapter soft POV and not get inside anyone's head?

If you change it to first person, you might create a worse problem if the POV is the "stranger."

I read a Thriller a few years ago where the author, a very well established one, got into the killer's POV. The killer was masculine in the POV. The person who done it, the same person, and whose POV we also got into is female. So, when that little "twist" came about, I threw the book across the room. I'll NEVER read that author's work again. So, it's probably not worth the cost to trick the reader.

Why don't you start with the demon's POV? Another masked being coming to sell a soul. Demon doesn't care what gender the soul is, probably, so wouldn't think about it. If you tell the story after using the other two student's POVs, you can keep that mystery from us, the reader, if those POVs don't figure it out. A reader doesn't need to know what the POV doesn't but must know what the POV does AND would naturally think about it. This plot line wouldn't work in full Omni as a result. Pick a POV that doesn't know the answer to the question.

A million thanks for your kindness and insight. The good thing is I still have months of writing ahead and have time to tweak that first chapter even if I have to write it 20 times.

It would be quite fine to go along from a POV that isnt that character and having them refer to the stranger as a male then at your twist reveal that it IS in fact a female.

How many times have we made assumptions about the gender of a baby to have the gloating and now slightly annoyed parent correct us. If there is a good reason (and there should be) to keep this secret (like only men can be in the school), the Stranger won't correct the wrong assumption.

kings falcon, I've decided to make the 'man in the alley' into a drunken sailor on a wharf. Sailor cannot be confused with Stranger, i.e.

<<<"You're either lost or you're new in town, stranger."

The stranger scowled beneath the mask.>>>

The student explains to the demon why he/she wore a mask in the first chapter. I am using misdirection carefully enough (hopefully) that everyone will assume it's a man, kings falcon. You brought up a great point when you wondered if only men can attend the school. That IS glossed over in the narrative and the reader only meets male students up to a certain point and the subject of female warriors is never brought up. Early on a list of the schools is read aloud and among the Irongates and Lionhearts and Dragonsmiths there is one school called White Glove. The first of the story takes place in a military school environment and that school name is very innocuous and above board, but also incongruous with the other masculine names.

At least, I think it's a fair and viable misdirection. If I’m thinking wrongly please let me know.