Raven is definitely a cockerel, the male saddle feathers confirm it. Even if he didn't have saddle feathers, the size and color of his comb and wattles compared to the pullets the same age are another dead giveaway.
Whether you can keep 2 males or not depends on a lot of variables. How much space you have, how many females you have, and each individual cockerel's personality are the main deciding factors. The fact that Raven submits is helpful, but as he matures and hormones kick in that may change. If you have enough space for them to get away from each other and neither one of them has a personality that won't tolerate male competition you're likely to be ok. Also, if you have "enough" pullets that they don't feel the need to fight over females.