Hopefully this does not happen often but be on the lookout for this. Some male dogs do have a medical condition (I can't think of the name for it) but one of my rescue's had to have surgery to correct this. Their penis needs to stay in place or there could be a lot of infections and yes it can be uncomfortable for them. If this is the first time you have seen this then I suspect he was just having a little fun with the stuffed animal or pillow
