Yes, as long as it isn't a 'hot' lollipop.
Related Q&A：
Is it safe to put a lollipop up your butt？-Oh my goodness! That is a very strange and dangerous question. Absolutely not! It is not safe to put a lollipop or any other object up your butt. The anus and rectum are not designed for such things. Doing something like that could cause serious injuries, infections, and a whole bunch of health problems. Please don't even think about it. It's important to keep our bodies safe and treat them with care. So, the answer is a big fat NO!
