I have tried multiple times and it hurts unbelievably bad. I can handle a finger but nothing more. We have tried lots and lots of lube and I've been relaxed but it doesn't work. Recently we tried a vibrator, turned off and lubed. It started fine but its tapered and it was like my butt sucked it in! Let me tell you that pain almost made me faint. We've tried once again without the vibrator, just him , and I still couldn't handle it. I don't really care to do it but my boyfriend really wants to. Has anyone else had this issue?