autoload1.rb

cls = []

2.times do |i|
  cls[i] = Class.new do
    def go
      autoload :Autoloaded, 'autoloaded'
      p autoload? :Autoloaded
    end

    def it
      self.class.const_get :Autoloaded
    end
  end
end

2.times do |i|
  c = cls[i].new
  c.go
  p c
  p c.class.constants
  p c.it
end

autoloaded.rb

puts "LOADED"

class Autoloaded
end