"He was searching for U-boats," Mr Houston said.
"He attacked one and then he got shot down and the whole crew was killed. The boat captain survived and contacted the UK to tell them about the bravery and he (Trigg) was awarded the VC based on information from the German captain."
The other box features another hero, Cobber Kain, who was a Kiwi fighter pilot with the Royal Air Force.
Kain became a household name in the UK for his victories in the skies. He was later ordered to return home due to exhaustion and intended to pilot a Miles Magister to England across the English Channel.
In a gesture to his comrades he took off in a Hurricane to perform a series of low-level aerobatics but crashed and was killed.
Mr Houston said he would also be keen to paint the Ward Ave Chorus box, as James Allen Ward was his "boyhood hero".
"It's a great thing Chorus is doing," he said.
"It's been amazing, while I was painting, people were stopping and talking to me about it. It's great that we can tell them the stories and a wonderful way to commemorate them."