Batch send to a Category group in Outlook

Earlier I used a super email program called Calypso. With which we could send an email to a group of members / customer etc. and it was even possible to send them as blind messages.
Switched over to MS Outlook and thought it should be possible to do the same thing and email to a category. Unfortunatly I have not found any solution to this feature Maybe someone can show how to do it.