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Heat a medium saucepan over medium, then add enough oil to lightly coat the bottom. Stir-fry the guanciale and onion until both start to brown at the edges, about 5 minutes, then scooch them to the side of the pan.
To the empty side of the pan, add a little more oil if dry, then stir in the crushed red pepper and oregano. Reduce the heat if the spices start to burn. Nestle in the tomatoes (with their vines still on) and cook them until fragrant, about 1 minute.
Add the rice and stock and bring to a boil over high, then reduce the heat to medium-low. Simmer, stirring occasionally, until the rice is tender, 15 to 20 minutes. Taste and season with salt. If your tomatoes had stems and vines, remove and discard them.
Serve immediately with a topping of fresh basil and a dribble of sesame oil, if using.