Prepare pudding mix according to package directions, using 2 cups milk. Cover and chill 5 minutes.
Toss sliced peaches with granulated sugar.
Cut pound cake into 1/2-inch slices. Place half of cake slices on bottom of a trifle dish or deep bowl; drizzle evenly with half of bourbon. Spoon half of peach mixture evenly over cake slices. Spread half of pudding over peaches. Repeat with remaining cake slices, bourbon, peach mixture, and pudding. Cover and chill at least 2 hours.
Beat whipping cream at medium speed with an electric mixer until foamy; gradually add powdered sugar, beating until soft peaks form. Spread whipped cream over trifle; sprinkle with almonds.