I had a girlfriend who loved anal and I wondered how it felt--but I was too scared to try anything bigger than a finger.
After she broke up with me, I moved back to my hometown and rekindled a relationship with my best friend, a guy. I gave him blowjobs. After a few months, he told me he wanted to fuck me! I was scared, but I simply could NOT say no to him. So I went to a local adult video store and bought a classic 6" vibrator and taught myself how to receive anal. When he topped me, it went smoothly and felt AMAZING.
Now I still use anal toys mostly for warmup, but now it's warmup for pegging with my wife. I also have learned to like p-spor stimulation during solo play and I'm going to try long-term wear and see how I like that.