Graham crackers and/or Gingersnaps for dipping (or fruit, pretzels, etc.)
Stir pumpkin puree, pumpkin pie spice, and 1/4 cup sweetened condensed milk together in a small bowl. Set aside.
Place the chocolate chips and heavy whipping cream in another small bowl or glass measuring cup. Microwave in 30 second increments, stirring between each, until the chocolate is melted and smooth (about 1 minute total in my microwave).
Pour the chocolate slowly over the pumpkin mixture. Use the back of a wooden spoon or a knife to swirl it.
Place the marshmallow cream and remaining 1/4 cup sweetened condensed milk in yet another bowl. Heat for 20-30 seconds, until it stirs smooth. Pour slowly over the top of the chocolate pumpkin mixture and swirl again.
Serve immediately with gingersnaps, graham crackers, fruit, or pretzels for dipping.