The fourth one really doesn't look any different to the third Other then being taller.
The overall silhouette is more distinctively masculine. Thicker legs, wider waist making the chest-torso-hip line straighter, longer torso, broader shoulders, completely flat chest.
There's a similar difference between the female and otoko no ko versions, too.
The right two also have a line on the neck which is supposed to imply how the male neck has more defined tendons.
So, a transvestite. As far as I know, a crossdresser is somebody that just wears clothes of the opposite sex, while a transvestite is also somebody who get a personal pleasure from doing that.
Since I see a erected penis, I'll just assume that Shimakaze-kun is experiencing a personal pleasure.