In a mixing bowl, beat cream cheese, granulated sugar, and brown sugar until truly smooth and creamy. Add peanut butter and milk, continue mixing until integrated into a luxurious, thick cheesecake layer.
In a separate chilled bowl, whip cold heavy whipping cream with vanilla extract, cocoa powder, and powdered sugar until stiff peaks form—creating a rich chocolate layer.
Begin assembling in clear serving cups: spoon or pipe a layer of the peanut butter cheesecake base evenly into each, pressing slightly for uniformity.
Sprinkle a few chopped Reese’s on top of the cheesecake layer, then drizzle with chocolate sauce for an extra chocolatey kiss.
Top with a generous swirl or spoon of the chocolate whipped cream.
Repeat the layering with another cheesecake dollop, more chopped Reese’s, and a drizzle of chocolate sauce.
Finish each trifle with a final swirl of whipped cream and garnish with a half mini Reese’s on top.
Chill the assembled trifles in the refrigerator for at least 1–2 hours to set and meld flavors before serving.