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In the "To username" enter everyone you want to send to, like this.

Mel_Ruller, b4melinda, JohnWest

The next time you want to send to the same group all you have to do is double click in the empty "To username" box and select from the list displayed.

If there is a username in the box and you want to send to multiple recipients, just clear the box and then double click it and select from your list. Of course this list will grow as you define it.