I teach English at an elementary school in Japan. While working I normally
call the teachers by their last name plus 先生. Like 田中先生 for example.

However, after work, let's say 田中先生 invites me to have a drink at an 居酒屋. Am I
still expected to call him (or her)「先生」 even if it's just the two of us and
we're outside of school? Would it be rude or inappropriate to call him 田中さん?
Does the teacher's age or gender make a big difference?

Edit: If I was Professor Moriarty's student, I would call him Professor. If he
was a co-worker that I've known for years and consider a friend, I imagine at
some point I would start calling him by his first name. In America, I think
most people let a person know when they can use their first name or nickname
by directly saying something like "Call me Bob!".

How about Japan? When a Japanese person becomes friends with someone, do they
usually say, "You can call me ...!"? Switching from first names to last names
or knowing when I can drop さん or 先生 has always been confusing for me.

Do you think it would be OK if I just asked directly? Like, "Can I call you
...?"

Edit 2:

I am an ALT. I've been teaching at this school for 2 years. I normally try to
use 敬語 and always use です and ます。 Most of the teachers speak informally to me
and don't use much 敬語。But most of the teachers are a lot older than me, so I'm
not sure if it's because I'm younger or if it's an invitation for me to speak
to them casually.
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usage politeness
How to use ～先生 properly with co-workers?
Normally when the Japanese company workers go out for the 飲み会(party) with
their Manager or Boss they call them 部長 or 社長 only.

In the same way your students will call you as ~先生 even after they
graduated/move to higher education.

Usually it's difficult for you to call it as 田中さん because you used 田中先生 all
the time to call him/her. However if you're friend to that person you can call
with lastname + san, or just with firstname. But if you only known them as a
colleague, better to call them as a 先生。
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This question is largely about culture but a place where culture and language
interact.

I work at a university in Japan and both on and off campus, we call each other
苗字 (family name)-先生. There's one or two exceptions where a 高橋 goes by her
first name (one of four takahashi's).

Japan is a relationally organized society, and the manner in which you know
the teachers there is _as teachers_. Thus, I think it will be off-putting if
you switch from 先生 to さん. I'd say it's more likely to switch to given names
than for it to be appropriate to call him 田中さん. (tldr: imagine switching from
calling someone Professor Moriarty to calling him Mr. Moriarty. It'd be kind
of weird right?)

In terms of what will happen in your environment. There's a few things to
consider here as to what is possible. The three possibilities are (let's say
his name is 田中[良和]{よしかず}):

  1. You will continue calling him 田中先生
  2. You will start to call him よしかず (if he wants to and suggests switching to first names).
  3. You will start calling him a nickname like よっちゃん or something (if you have that sort of friendly relationship).

What will not happen is that you will switch from 田中先生 to 田中さん because that
makes no sense to do. As I stated above, it's not a sign of familiarity to
change from Professor Moriarty to Mr. Moriarty.

What seems to affect whether you have something like 2 or 3. I'd suggest two
factors:

First, while you write `I teach English at an elementary school in Japan`, if
you work as an ALT, then according to the Japanese educational system, you're
technically not a teacher. I mention this not because I agree with the
assessment but because that may affect the expectations of the 教諭 who work
with you there. (tldr: do they think of you as a teacher like them or
something else?)

Second, many Japanese expect that foreigners prefer to be called by their
first names but don't necessarily want to be called in this way themselves. I
don't know if there's a strongly age-based pattern to this but this might
affect whether the teacher wants to feel close by communicating with first
names.

* * *

Can you ask from your side if you can call him よしかず or よっちゃん?

My first question would be _how_ you're communicating with him now. Do you use
敬語[けいご]? Do you use endings like ます (for instance 食べます) and です? Does he speak
to you casually ?

If the answer to any of these questions is no, then there's no linguistic
signal that this is a good idea.
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As an 83-year old Japanese person, I too have been long puzzled by why school
teachers in primary school and junior high school teachers call each other
“先生.”

In our conversation in business world, we call senior persons simply by their
titles, eg. 社長、専務、常務、局長、本部長、部長、課長, 係長、主任, or 支店長 (of banks, car dealers)、店長,
マスター (of retail shops and eateries,) often omitting their name, e.g. 田中、伊藤、中村,
but we don’t call our colleagues 先生. Instead, we attach suffixes 君, さん onto
their name, or simply call by their name without adding an honorific title.

先生 is also often heard in hospitals and law farms, where doctors and lawyers
call each other 先生. Lawyers in a big law firm I was in contact with when I was
in office used to call their co-workers "xx 先生".

先生 is also used in a derisive way, for example;

> 先生、よく言うわ – What nonsense that he says!

> あの先生がやらかしたことだ – This is what that guy did!

Calling 先生 each other seems to be a nostalgic remnant of the age and society
where school teachers, doctors, and lawyers were once regarded as a privileged
class or an esteemed profession to me.
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