So we've picked up a butt plug, having heard that wearing one before anal play makes things go easier. So far, we've had fun with it, trying to get it all the way in, and find that the act of trying does have a loosening effect. However, we've been unable to get it all the way in! We're using plenty of lube, so it doesn't feel like its a friction problem; just that the hole feels like it can only stretch so far. Are there any techniques or approaches that are recommended for getting these things in to the proper depth?