COMBINE berries and sugar. Refrigerate until ready to use. Beat cream cheese spread in large bowl with mixer until creamy. Gradually beat in milk. Add dry pudding mix; mix well. Blend in 1-1/2 cups Cool Whip; spoon half into 2-1/2- L bowl.
TOP with cake, berries and remaining cream cheese mixture. Refrigerate 4 hours.
MELT chocolate; drizzle over trifle. Top with remaining Cool Whip.