You know I liked this a whole lot better when it was about a trans girl who had a nice supportive girlfriend and i could ignore the plotline in the background, the manga i just described above will never happen though because so few trans manga get made as is, crossdressing? yes. Trans? no.
To be honest, I'd be surprised if much crossdressing manga was authentic to what actual crossdressers experience than futa is a reflection of trans or intersex people. Indeed, is there any crossdressing manga that has a very sensitive approach to the subject, or is it pretty much all comedy and fetish?
Well I guess you could count Akemi from Sasameki koto because I started to get the feeling they were having actual identity issues near the end of that series (It says a lot that they turned up for the date with sumi in the female persona).
Also that they returned to crossdressed modelling after graduation.