Lollipopped - Futa Tales: Season 1, #4

Bobby Jones and Angela Tan have been friends for over fifteen years. Now, they are roommates living in the big city. One day, the lock to the friend zone brilliantly constructed by Angela begins to crumble, walls fall, and the two consider exploring a relationship. Bobby had never been with a transwoman before, and Angela had her share of cis men using her as a fetish. Bobby takes on the challenge of passing the test.
Will he be able to win her love and pass the test?