config.ru

require "intercession"
require "myapp"
require "myapp/session_extras"

use Rack::Session::Cookie, :secret => "I'll punchasize your face for FREE!"
use Intercession, MyApp::SessionExtras

run MyApp

intercession.rb

class Intercession
  def initialize app, behavior
    @app      = app
    @behavior = behavior
    
    methods   = []
    @behavior.instance_methods.each { |m| methods << "#{m}" }
    @before   = !!methods.include? "before"
    @after    = !!methods.include? "after"
  end

  def call env
    if session = env["rack.session"]
      session.extend @behavior
    end

    session.before if @before == true
    @app.call(env).tap { session.after if @after == true }
  end
end

myapp.rb

class MyApp < Sinatra::Base
   get "/" do
     halt 403 if session.anonymous?
     "Yay, I know you!"
   end
end

session_extras.rb

class MyApp
  module SessionExtras
    def user
      @user ||= self[:user_id] ? User.find_by_id(self[:user_id]) : nil
    end

    def anonymous?
      !user.nil?
    end
  end
end