I started anal masturbation around 17 years old, first with fingers, then a toothbrush case. I tried really hard but It was painful and not so pleasurable. I stopped doing it for years after I had a gf. Recently my gf was far away from me for months and I got too horny to experiment with anal masturbation again with finger penetration. It felt so good and I could feel the sensitive spot which was similar to my gf's G spot. The orgasm was intense but without ejaculation. In fact, from my previous experience, my urge for ejaculation disappears whenever anal penetration starts. The urge of anal penetration continued to be strong for the next two days until I masturbated my penis. However, the second time I tried it when I wasn't as horny, it was not so pleasurable anymore. The sensitive spot should be P spot but mine didn't provoke ejaculation. It made me felt more like a vaginal orgasm. Does any guy has the same experience? Why didn't mine work all the time while my ex gf could have anal sex exclusively 4-5 times a week?
You won't get deep enough with fingers, I am a gay bottom so I have had lots of experience in this area. Get a 7" or so dildo and go from there. You will need to get used to it (lube and gentle insertion at first). I have a few 9" dildos for when by bf is away. Fucking your ass with the dildo (just like you see in anal porn) will give you quite satisfying results.
