To prep filling, whip together pimento cheese and cream cheese. You can use a fork for this but for best results beat it with either a hand mixer or a stand mixer with the paddle attachment for a minute or two. Transfer to a sturdy plastic bag for easier piping.
Preheat a sturdy skillet over medium-high heat. Add canola oil and once hot, add peppers. Cook until the peppers char on both sides, maybe 2-3 minutes per side. Try not to overcook them or they will get too soggy.
Remove peppers and let cool.
Slice each pepper open down the center. It’s okay to leave the seeds in. They shouldn’t be spicy.
Pipe in pimento cheese filling and garnish with sesame seeds.