Sigh. And this story idea is not so hypothetical.

I am married with two step daughters (and yes, my husband "knows"... although I am stealth to most of the rest of the world), and while my children are not trans... the closest I can come in personal experience to your scenario was something that happened a few years ago. At that time, I worked with "special needs" children... including a transgendered early teenager. A child who is still a minor, and this is a public forum... not to mention work confidentiality agreements... so I am severely limited in how much I can say... but I will say this much.

In the couple years I worked with that child, I was pretty much the only person in his/her life that was even remotely supportive of how s/he felt... so it is perhaps not that surprising that the child bonded to me much more than is normally the case at work. Confided all sorts of things in me... and asked me for advice about many things. I was not this child's parent -- but as the real parents were "hostile", I suspect I ended up "in loco parentis" to her/him in many ways. Certainly, s/he seemed to deeply respect my opinions on things, and paid very close attention to any "suggestions" I made...

Did I ever admit I had some things "in common"? No. It was a question that I wrestled with internally, literally for years... often starting to say something, only to bite my tongue and change what I had started to say. In the end, I never did disclose. Instead, I found ways of sharing information with the child that I attributed to other people. A nurse I had worked with before (I also used to work part-time in a hospital back then), who had transitioned FtM. An intersexed person that I knew. Second hand stories from one of the women I knew in the hospital lab, whose spouse was transitioning. A couple teachers at other schools in the district, whom I knew were post op TS. I was always careful to not say *too* much about those others -- since they *were* real people, and most of them were also "mostly" stealth -- but I was careful to always go through a show of agreeing to ask them about questions the child had... then getting back to him/her with an answer the next day. An answer that in reality came entirely from me.

[The child was also completely blind -- merely suggesting places to look on the web for information would not have been practical, as s/he still needed assistance to use a computer... and the person training the child to do that was "unsupportive"].

Why all the "asking a friend" rigamarole? Sigh. I once knew a trans-guy, fairly deeply stealth. [What can I say... those of us who live stealth occasionally feel a need for "unrestricted" talk... which we can not do in our daily lives. So we tend to have very carefully chosen, rarely seen friends among those who move in similar circles... or at least, it has seemed to happen to me that way...]. Anyway, the organization he worked for was revising its anti-discrimination policy... and he made the simple mistake of being "too knowledgeable", on the subject of transgendered issues. Shrug. Most trans-guys pass extremely well (with their clothes on, at least), and even for a trans-guy, he was much more passable than usual. You would think that he could talk about that sort of thing with immunity... but such was not the case. He was fired a few weeks later. I don't really know too much about what happened later -- he moved to another part of the country and went really deep stealth, cutting all ties to his past, after that... in an attempt to re-build his life. The downside to being stealth at work -- if your "legend" is blown, employers sometimes get nasty about it...

Being stealth (or even just "less than entirely Out and Proud"), one of the biggest "tricks" is simply to never do anything that raises questions in the first place. In this day and age, if someone *really* gets serious about digging long and deep into anyone's past... they can often (not always, but often) find *something*. The trick is to never give them a reason to look that hard. Shrug. I work with kids, and as such I have detailed background and criminal record checks done on me every year -- it's just part of the job, here. Despite that, I am completely stealth at work... I managed to bury things *that* deep. But even I could be "outed" if I were stupid enough to give someone a major clue, or a major reason to not stop with "routine" checks. A reason to pay someone to dig deeper and deeper into every tiniest aspect of my history.

And so... I am always careful (in my 3D life) about just "how knowledgeable" I let people know that I actually am, on any GLBT issue related subject. I help when and where I can... but circumspectly, attributing things to stuff I "heard on a talk show", or "was told by a co-worker", or some such dodge -- and I hold back even then, never really admitting the full depth of my knowledge. It is just part of living the way that I do... something I have done for so long that I don't even think about it anymore...

Shrug. A rather lengthy answer, but I think one that is relevant. The short version would be, I would use the information I have "to help him find himself the best way [I] could".

As someone who transitioned young myself (although long enough ago that I am no longer young)... and works with children... I simply can not imagine outing myself to a child. An adult? Maybe, under unusual circumstances... although very cautiously. People are complicated and wear all sorts of masks... you never know exactly how someone will react to that sort of information. But a child? Way too risky. I work with kids (both very young and teenagers), and it might raise your hair to know just how many of them have confided things to me such as, "Dad wears mom's dresses on the weekends" (a comment from a sixteen year old boy, made with rolled eyes and a "what can I do about it" sort of shrug), or "Mommy isn't feeling good today 'cause she had a 'bortion yesterday" (an eight year old girl), or "I am staying at my aunt's tonight 'cause my mother is back in drug rehab again" (a twelve year old) -- just to use a few recent examples.

Would a TG child/young adult do that? Maybe. Maybe not. Even if I were certain that the child was truely transgendered (and not just experimenting), many kids that age are still questioning themselves... not at all certain of themselves. Going through cycles of self-doubt, and often attempting to "purge" such things from themselves -- trying to "become a man" by "acting like a man". It is why there are so many TS who have histories of having served in the armed forces, being police officers/firefighters/body builders/you name it -- anything "macho" and often "dangerous". The risk that the child would, sometime in the future, go through such a self-denial phase... and say something to someone during it... is just way too high. They might regret doing so right after they did it... but it would already be too late...

Or at least, that was the conclusion I reached, after a couple years of being in the situation I described. Shrug. Maybe it was just me, and I should have done something different. We will never know -- the kid moved to another school district a couple years ago...

Sigh. My answer might be different, if I were an adult transitioner who had kids from *before*, or was "out and proud" enough to be doing public speaking. But you specified an early transitioner... and from context, both many years post op and with the implication that she was stealth. Which complicates things a *whole* lot...

Just my two cents worth. I hope something in here was helpful to you...