Stretched ears

Hey everyone I’m currently in the process of stretching my ears. Does anyone have any tips on how to get the gauges in easier? Once it starts getting on the thicker side it hurts really bad and won’t go in. My pain tolerance isn’t very high so I can’t just jam it in. I’m on the very first pair and want this to be an easy as can be process. Thanks for any help!

Edit: I’m using acrylic tapers and don’t know any other kinds to use. These ones I hate. I’ve had them in for almost a week now. The black bands never stay on and the taper has been continuously falling out of my ears.