Where I am (East coast of the US,) a 'rap session' is most commonly used as a musical term. Where one person, or a group of people, practice their freestyle rapping. It can be casual or competitive depending on the setting. An example would be in the movie "8 Mile," in the where Eminem and his friends meet and take turns free-styling. (That scene might be wrong. It's been a long time since I've seen that movie, but it's more or less an accurate depiction of what I define a 'rap session' as.)