Using room temperature wine, place in small bowl and add gelatine; mix well. Add parmesan cheese and dissolve by stirring constantly with a small whisk. Set aside and let gelatine form.
Heat half & half in a saucepan until bubbles form around edge of pan; do not boil.
Place grated cheddar in food processor. Slowly add half & half and mix until cheese is smooth and silky. Add salt and pepper.
In a serving bowl, place 1/3 of the cheese mixture on the bottom. Dollop 1/3 of the port wine "jelly" on to the cheese. Using a chopstick, "marble" the port, but not mixing completely with the cheddar. Repeat this step two more times. Remember, the last time you do this step is your "presentation". Swirl carefully!
Chill for at least 6 hours so the flavors can marry. When ready to serve, let come up to [nearly] room temperature. Enjoy!