Try experimenting with condoms, especially when jacking off alone. Don’t just use condoms when you’re fucking, practice with them when you’re masturbating. Get used to the feel of different ones. Once you jerk off with them a few times, it’s a lot easier to use them when you’re fucking. You’re more familiar with them, know the ones you like and how to use them to best pleasure yourself. Try different lube/condom combinations. The object is to get very familiar with condoms and lube, letting them become part of your pleasure, not an obstacle to it.