Add sliced strawberries, water, and sugar to a saucepan.
Cook over medium heat for about 10 minutes, stirring frequently until strawberries are soft.
Remove from heat and set aside to cool.
Making the Banana Pudding
In a mixing bowl, add pudding mix, milk, and heavy cream.
Whisk together or use hand mixer until fully combined.
Refrigerate for 5-10 minutes, or until pudding sets.
Add in vanilla extract and mix again.
Fold diced bananas into pudding.
Set aside.
Making the Whipped Cream
In a separate bowl, add chilled heavy cream and beat with stand mixer until stiff peaks form.
Add in powdered sugar and mix until combined.
Add in vanilla and mix again.
Set aside.
Assembling Pudding
In a trifle or individual serving cup, layer banana pudding, strawberries, and vanilla wafers. Top with whipped cream, more vanilla wafers, and a sliced strawberry.
Serve immediately or refrigerate until ready to serve.