If you have this installed on a Windows system, this can be done. If you have a Mac, Outlook is not a compatible email client that you can use.
You have two ways to send an email to multilple people in your database. There's an option to send "multiple emails, one for each record in your found set" that can be used if you can pull up a found set of just the recipients you want. If they are all to get the same message, you can set this message up in a global field or you can specify just literal text in the body text box of the send mail dialog.
You can also use a calculation and/or script to pull the email addresses together into a single field with each email address separated by a semi colon or comma (use the separator specified for your email client.) Specify this field for your TO box in the Send Mail dialog.
Either approach can be used for what you describe, the second option exposes the email addresses of all your recipients to each other, so this may or may not be a desirably side effect.