Ask Kim: Bottoming is a Pain

Dear Kim, 

I recently tried bottoming for the first time and it kind of hurt. A lot of my friends who are bottoms seem to really like it but I don’t understand. Am I doing it wrong? 

Thank you, 


Dear Butthurt, 

It’s not uncommon to experience some difficulty when trying receptive anal sex, or bottoming, for the first time. There are a few ways to make it a more pleasurable experience! 

First off, if it hurts, stop. You don’t want to damage the delicate tissues down there! Next, try some foreplay. Inserting smaller things very slowly to “warm up” will help relax your internal and external sphincters. Wait, what? Two sphincters? That’s right – you have an external sphincter, which you can relax at will, and an internal sphincter that relaxes with gentle stimulation. It’s essential that both of these muscles are relaxed for comfortable bottoming. 

Lube is also really important for anal sex! There are water-based lubes specifically formulated for anal sex. Some people prefer silicone-based lube because it is longer-lasting. Be sure to avoid silicone lube if you’re using silicone sex toys. There are also folks who use oil-based lubes, like coconut oil, but these CANNOT be used with condoms because they break down latex – and I recommend using condoms during anal sex EVERY time to avoid STI’s like chlamydia, gonorrhea, and syphilis. 

Last, know that not everyone likes bottoming – heck, not everyone even likes anal sex! – and that’s totally OK! Oral sex and mutual masturbation are great ways to get intimate with a partner. 

I hope this helps you create a fun and pleasurable experience for you AND your partner! 

Be well, Be yourself. 


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