Beat egg yolks and ¾ cup sugar until the mixture turns light yellow. Add milk and vanilla.
Combine egg yolk mixture with dry flour mixture, stirring gently just until combined.
Beat egg whites until soft peaks form, then add final ¼ cup of sugar and continue beating until egg whites are stiff.
Fold beaten egg whites gently into the batter mixture just until combined.
Thoroughly spray cupcake pans. Fill each cup about half way with batter. It is best to work quickly, because the batter will start to fall. I had good luck with my first 3 pans (I can only bake 1 pan at a time in my oven.)
Bake 8-10 minutes, until tops turn golden brown and a toothpick inserted in the center comes out clean.
Wait about 5 minutes, then gently remove cupcakes from the pan. I used a fork to pull the cakes away from the pan around the edges then they came out fine. Allow cupcakes to cool completely.
Then combine evaporated milk, sweetened condensed milk, and ¼ cup heavy cream in a bowl. Whisk to combine thoroughly.
Cut waxed paper or parchment paper into squares (about 3.5″ X 3.5″, or 1/3 the length of the roll worked well for me). Put the cupcakes back into the muffin pan upside down on top of the squares. This will work better than muffin cups because the paper will be loose around the edges allowing the milk mixture to drip down the sides so that it can be better absorbed by more of the cake.
Poke each cupcake with a fork 2 or 3 times.
Pour milk mixture over the upside down cupcakes, about 1 teaspoon at a time. Go through the whole batch and then start again, repeat several times. At first the milk will pool on top but will be soaked in when you start the second time around. It is amazing how much liquid this cake can hold!
I started by focusing on the tops and after 2 or 3 times I started letting some of the liquid drip down the sides. I repeated about 6 or 7 times. Continue repeating until the cakes seem thoroughly soaked and the sides of the cake are moist and sticky. Rest after each round just a bit to absorb the liquid.
Let the cakes sit about 30 minutes. In the meantime make the icing. NOTE: this makes a bunch so you could probably half the amounts of each ingredient on the icing list and still be fine. Beat the remaining pint of heavy cream with 3 Tablespoons sugar. (Honestly, this makes way too much whipped cream, but I made the whole recipe because I wasn’t sure how much to use.)
When soft peaks form, add a splash of vanilla and the juice from maraschino cherries. I was hoping to flavor the whipped cream with the cherry juice, but it wasn’t as strong as I hoped and didn’t soften the whipped cream, so add even more if you want a stronger flavor.
Continue beating until firm peaks form. I went a bit past standard whipped cream.
After cakes have been sitting for 30 minutes, top each with whipped cream and a cherry. Store in the fridge.