In order to send multiple documents for e-sign you need to make sure you are under the Checklists or Documents tab within necessary transaction, select the task and click the Use forms button from the right hand side menu.
After that you can select required forms by checking appropriate boxes and hitting Submit.
Once selected you will see the list of the forms you would like to send for e-signature. You can add additional ones by clicking add form link or go to the next step by clicking the Next button.
Signers are going to be populated into your e-sign package documents according to the roles assigned to the them in the transaction. You can add missing signers or delete not required ones. After information has been reviewed and adjusted click the Next button.