Quite simple really. For example:
Private Sub CommandButton1_Click() 
Dim Rng As Range, StrOut As String
If Me.OptionButton2.Value = True Then
    StrOut = "EXAMPLE SENTENCE 1" & Chr(11) & vbTab & _
            "EXAMPLE SENTENCE 2" & Chr(11) & _
            "EXAMPLE SENTENCE 3" & vbCr & " " & Me.TextBox1.Text
Else
    StrOut = ""
End If
With ActiveDocument
    Set Rng = .Bookmarks("BOOKMARK2").Range
    Rng.Text = StrOut
    .Bookmarks.Add "BOOKMARK2", Rng
End With
End Sub
More flexibly:
Private Sub CommandButton1_Click()
Dim BkMk As String, StrTxt As String
Call UpdateBookmark("BOOKMARK1", Me.TextBox1.Text)
If Me.OptionButton2.Value = True Then
  StrTxt = "EXAMPLE SENTENCE 1" & Chr(11) & vbTab & _
            "EXAMPLE SENTENCE 2" & Chr(11) & _
            "EXAMPLE SENTENCE 3" & vbCr & " " & Me.TextBox1.Text
Else
  StrTxt = ""
End If
Call UpdateBookmark("BOOKMARK2", StrTxt)
End Sub


Sub UpdateBookmark(BkMk As String, StrTxt As String)
Dim Rng As Range
With ActiveDocument
  Set Rng = .Bookmarks(BkMk).Range
  Rng.Text = StrTxt
  .Bookmarks.Add BkMk, Rng
End With
End Sub