My first time did hurt as well even though I was "conditioned", a tip I learned was try to relax the sphincter as much as possible. That is also good for cleaning your dick and your body after the fact. A healthy, fiber-rich diet lots of veggies, less meat eliminates the need to douche for some. It just means you need to be in a place in life where you can get routine STI testing — men who have sex with men should be tested for HIV and other STIs every months, minimum. PrEP requires good health insurance and an understanding doctor who is aware of your health needs.
They taught you how to get better.
21 Things to Know Before Losing Your Gay Virginity
I know there are links on the Internet for vaccinations that are recommended for gay men. Maybe you should seek out sex education information before you go forward. The wonderful benefits of sex far outweigh the risk of STIs. And again, a large quantity of Tea Towels small hand towels. The best thing you can do to protect yourself is have a doctor who you trust, who performs regular checkups. Here is a resource to help you find STI testing centers.