First time using a dildo?

Hi! I’m a gay man and I recently bought three different sized dildos in the hopes of stretching my virgin hole and I’ve been trying them out. I started with the smallest one with lots of lube and it took about 15 minutes before I felt I was ready to use the second largest one. The glans was a little difficult to get in but with more lube I was able to get it all the way in but couldn’t ride it for too long due to the discomfort. The next day I was having pain mainly at the entrance and I was wondering if that’s normal? There was no bleeding so I don’t think it was anything serious. Also, for those of you who use dildos, how long does it take to feel comfortable using them?

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