Can Outlook send multiple simultaneous emails to different people without doing a bcc?

The easiest way to do this is with Word Mail Merge. When you use the mail merge wizard, the first thing you will select is the document type. One of your choices is Email Message. Later, you will get to select Outlook as your source for the email addresses. Even nicer is the fact that you can include values from your contacts in your email text by including fields.

Each email is sent separately with its own To: address.