Message: I Really Want To Like Anal

Anonymous: I keep trying anal because I really want to like it and be like one of the beautiful ladies on here, but I never get off and it never feels good. I’ve tried with several different partners, and it’s always the same. Help!

There can be a lot of different reasons it doesn’t feel good for you, and it’s hard to pinpoint precisely without more information. You may need more lube, you may need more warmup, or you may simply need more practice. For many people, anal is a new sort of stimulation and requires developing new associations between those feelings and the idea of them being pleasurable initially. Though I am very much opposed to women ever playing with their clits and pussies once they’re more anally experienced, it can be an essential component of early anal training—make sure you always play with your clit while experimenting with anal play. It can make all the difference at first as to whether something in your butt feels good or not.

You should probably be training anally on your own initially rather than just trying to have sex. Use fingers, a dildo or a butt plug, but make anal penetration part of your standard masturbation routine. Every time you masturbate, ideally daily when possible, make sure you also have something up your ass, especially when you orgasm. It shouldn’t take long for this to be feeling good and for you to feel amplified and different orgasms thanks to the anal penetration.

Have partners finger your ass while eating your pussy or during vaginal sex. Wear a butt plug during other sex acts. Essentially, start making anal play a constant part of your sex life, always during other things that already do make you feel good. Over time, you’ll learn to enjoy the anal play on its own and it will feel good just to wear a butt plug for a while or to masturbate anally, and after this point you should begin having anal intercourse again—but for a while at least, continue rubbing or using a vibrator on your clit at the same time to aid orgasm and make sure everything feel good as you get fucked. Over time, as you enjoy it more, I suggest becoming slowly less dependent on your clit.

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