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Hi there

I have done this before, for adding 'Calibri' font to the CKEditor and making it available in dompdf when printing PDF letters

Please download the font archive from http://dl.dropbox.com/u/34943170/Calibri_fonts.rar

Below are the steps i followed to make it work

To add 'Calibri' font to CKEditor

1. Copy the file 'calibri.ttf' from the downloaded archive to 'sites/all/modules/civicrm/packages/ckeditor/fonts'
2. Add the following to 'sites/all/modules/civicrm/packages/ckeditor/config.js'

config.font_names = 'Calibri;' + config.font_names;

/*
Copyright (c) 2003-2009, CKSource - Frederico Knabben. All rights reserved.
For licensing, see LICENSE.html or http://ckeditor.com/license
*/

CKEDITOR.editorConfig = function( config )
{
// Define changes to default configuration here. For example:
// config.language = 'fr';
//config.uiColor = '#AADC6E';
   
    // disable auto spell check
    config.scayt_autoStartup = false;
   
    // This is actually the default value.
    config.toolbar_Full =
    [
        ['Bold','Italic','Underline'],
        ['Font','FontSize'],
        ['TextColor','BGColor'],   
        ['Link','Unlink'],
        ['Image','HorizontalRule','Smiley'],
        ['NumberedList','BulletedList','Outdent','Indent','Blockquote'],     
        ['PasteText','PasteFromWord','SpellChecker'],
        ['RemoveFormat'],
        ['Undo','Redo'],
        ['Source','-','Preview','-','About'],
    ];
   
    config.font_names = 'Calibri;' + config.font_names;
   
};
3. Add the following to the end of 'sites/all/modules/civicrm/packages/ckeditor/contents.css' file

@font-face { 
    font-family: "Calibri";
    font-size: 12px; 
    /*src: url( fonts/helvetica.eot); /* IE */ 
    src: local("Calibri"), url("fonts/calibri.ttf") format("OpenType"); /*non-IE*/ 
}
Now you will be getting 'Calibri' font in the CkEditor font list


To add 'Calibri' font to dompdf

1. Copy all the files from the downloaded archive to 'sites/all/modules/civicrm/packages/dompdf/tests'
2. In command prompt, navigate to 'sites/all/modules/civicrm/packages/dompdf/' and Run the command to install the font in dompdf

This step will create .afm files for the True Type Font files using tt2pt1 utility. If Windows machine, you need to download the font convertor (ttf2pt1.exe) from http://www.columbia.edu/~em36/wpdos/typeinstall.html

Please check the path of the tt2pt1 utility at 'sites/all/modules/civicrm/packages/dompdf/dompdf_config.inc.php' around line number  183, before running the below command

php -f load_font.php -- Calibri tests/calibri.ttf
Now you should be able to print PDFs in Calibri font.

It works fine in CiviCRM 4.1.2