Back in 1984, I was working in a National park for the summer and fell into a sexual relationship with a gay male coworker. He was the first guy - and only guy for 35 years - who fucked me. And I fucked him too. We foolishly didn’t use condoms or lube. The pain from the penetration far exceeded and masked any pleasure there may have been. Also, my experience from fucking him was that I was grossed out when I had to clean his “excrement” off the tip of my cock.
That experience - as a young, naive college student essentially “scared me straight” for, well, 35 years.
Over the years, the visual of anal sex in videos has always been arousing but an experience that I was not open to reliving. But from chatting with new acquaintances on here and other forums, I have learned better how to prepare. So far, I have. Altered all of them with the exception of acquiring a plug or a dildo, which I really should do.
My suggestion for what it’s worth: Always use a condom until/unless you are in a committed or exclusive situation; lubricant is a requirement for both the top and bottom; cleanliness - a cheap enema from the pharmacy or a very good cleansing with water injected gently inside your rear goes a very long way towards relaxing and enjoying the experience particularly if it is likely that your partner will rim you during the experience.
My first experience being fucked in recent years was an older gentleman who took it slowly, lay on his back and let me lower myself onto his hard, condom covered, lubricated cock. The fact that he had a fast refractory period enabled us to fuck twice in rather quick succession which was great because I really enjoyed the second ride and THAT was the experience that has kept me interested in pursuing it when the opportunity is right. Subsequent experience has taught me that I really need to get a device to help me relax and train my sphincter. And yes, one friend had suggested one of the narrower and longer cucumbers.... don’t think I can do that.....