Message: Trying to Train My Ass

Anonymous: Hello, I’ve been trying to train my ass… but it’s been a few months and I still don’t seem to be able to relax enough. And it worries me because my daddy has a ver large cock and I don’t want it to hurt, but I want him to fuck my ass. How can I make the pain more bearable and turn it into pleasure for the both of us?

Anal shouldn’t hurt at all, and if it does, you’re not ready just yet for the size or speed that’s causing the pain. Go back down in size to something that doesn’t hurt, and focus on that size for a while.

A lot of my posts talk about clitoral denial and not combining clitoral stimulation with anal, but that’s more of an advanced technique for most, and if anal is uncomfortable or hurts, I highly recommend combining the two as often as possible as well as trying to orgasm frequently while masturbating anally as well. You want to associate the feeling of anal stimulation with pleasure, and clit play + orgasm will help you relax better, too.

Try to increase your frequency of training, and get a few sizes of butt plugs as well if you haven’t already. A lot of the popular jeweled butt plugs are pretty, and can help up to a point, but don’t do much training of the sphincter muscles themselves, because the neck is so narrow. Try getting something with a bit thicker neck, or working up to something like that over time. Wearing them whenever you masturbate if you aren’t doing something more active like using a dildo, and even wearing them during sex or just around the house or overnight, can be really helpful in helping you relax and open up.

If you are trying to increase in size and you feel like you aren’t relaxed enough, try bearing down/pushing out gently as if going to the bathroom. Your anal muscles are naturally tight and relax when “flexed”, so that can help open you up and ease in the object you’re trying to insert without pain.

Without more specifics I can’t offer too many other suggestions, but if you have any other questions, feel free to contact with a followup. I hope this helps!

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