Yes this is possible with the Windows Fax and Scan feature in Microsoft Windows 7.The user interface and design of Windows Fax and Scan resembles a standard email program making it very easy for first-timers to use. Windows Fax and Scan manages your faxes by storing them in various folders such as incoming, inbox, drafts, outbox and sent items. The attach documents features allows you to send multiple documents in a single fax.
For step by step method of achieving this;
Step 1
Click the "Start" button and move cursor to "All Programs" to expand the menu, then click "Windows Fax and Scan."
Step 2
Click the "Fax" tab located in the bottom left corner of the window.
Step 3
Click the "New Fax" button.
Step 4
Type the fax number you want to fax multiple documents to in the "To" field.
Step 5
Type the subject of the fax in the "Subject" field.
Step 6
Type the message you want to include with the fax in the message box.
Step 7
Click the paperclip icon in the toolbar at the top of the window to attach a document.
Step 8
Locate the documents you want to attach. Press and hold the "Ctrl" key and click each document to select multiple files from a single directory. Click the "Attach" button to add the documents. If necessary, click the paperclip icon and select files again if you have additional documents to attach to the fax.
Step 9
Click the "Send" button to fax the multiple documents.