Create two images - one being they picture you wish to show, the other blank. Then add a bookmark where you want the image to appear, and run the following function to place the picture or the blank image in the bookmark according to the value of the checkbox. If you employ a checkbox content control you can use the CC exit even to check the value of the check box and run the function with the appropriate image for the value of the checkbox. The image will only print if it is actually displayed in the document.
Code:
Public Sub ImageToBM(strBMName As String, strImagePath As String)
'Graham Mayor - http://www.gmayor.com
Dim oRng As Range
Dim fso As Object
Set fso = CreateObject("Scripting.FileSystemObject")
If fso.FileExists(strImagePath) Then
With ActiveDocument
On Error GoTo lbl_Exit
Set oRng = .Bookmarks(strBMName).Range
oRng.Text = ""
oRng.InlineShapes.AddPicture _
FileName:=strImagePath, LinkToFile:=False, _
SaveWithDocument:=True
oRng.End = oRng.End + 1
oRng.Bookmarks.Add strBMName
End With
End If
lbl_Exit:
Set fso = Nothing
Set oRng = Nothing
Exit Sub
End Sub