Welcome to 30BaD!
In my experience, I need to eat little amounts frequently. Something I found helpful was adding dates (or any high cal fruit) to my meals; lots of calories and I don't have to eat as much. Now I eat 15 dates every day just so I don't have to sweat about getting enough cals!
Also, I find that fruits with a high water content (watermelon, oranges) are MUCH easier for me to consume in large quantities. I get roughly 1/4 of my calories a day from various types of oranges!
Hope it helps ^_^
Start with one or two and work your way up sloooowly. Your body is not used to it. You could also try watery fruits like grapes, pears, nectarines…these are very easy to digest! Make sure you are mono-mealing.