I take though your old high school friend did not know that the woman was trans?
How did he feel when he found out?
He didn't take it well. My buddy who was the groom of the wedding didn't tell him for a few weeks hoping it would pass over but when the jerk from my class told him that they were in a hot an heavy phone romance he told him. The jerk called up the transvestite and told it that he would shoot her dead if he ever saw it again.