Message: (Almost) New to Anal
Rafaela: Hello, my name is Rafaela and I’m from Brasil. In 2026, I’ll be 35. I’ve only had anal sex three times. Two of these experiences were frustrating because the guys were already on the verge of cumming, so they lasted only seconds. For the other one, I literally hired a male escort because I wanted to feel pain—real pain. I was facing a difficult time and I needed something to make me ‘feel alive,’ and what’s better for that than pain?
I was lucky the guy was really sadistic (lol); it hurt a lot. I had to bite my pillow, the sheets, even the bed, but I didn’t ask him to stop—I really needed that. He was so rough I thought I was going to die, but once he finished and removed his penis, I sat up and it felt like nothing had happened. Really—no pain, no nothing. We chatted a bit and he left.
I felt incredible. I felt alive. I felt that I am able to push my limits and go further in life, even in other areas, not just sex. It changed my view of the world; I feel more courageous. And, most importantly, I became addicted. I haven’t had another anal experience since then, but I know I want it. Now, when I have sex and there’s no anal penetration, it feels incomplete. I really want to enter this new world, but I confess I feel a bit nervous, especially because I know how painful it can be if not done properly. Actually, I don’t even know if it’s done properly, if it will still be painful.
I have a few potential sexual partners with whom I chat, and they say they would love to have a lot of anal sex. The whole point is: how should I start? By putting things inside, like a butt plug, and trying to wear it for a long period? I’ve tried, but I couldn’t manage to keep it inside for more than, I don’t know, 10 seconds. It hurts. I think I already have the right mindset, but I need some encouragement. Could you provide it for me? Give me a step-by-step guide to follow, starting from the very beginning? I’ll wait for your response. Thank you for your patience in reading all this.
Hello, and thanks for reaching out. I’m glad that you’re looking to embrace anal sex and potentially go anal only. I highly recommend checking out our Guide to Anal Sex and the Anal Only Lifestyle which goes into great detail about all the various aspects of anal and AO.
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