Message: Guide To Enjoying Anal Sex?

Anonymous: do you know of any websites that are geared toward women to help them learn how to have more “comfortable” anal sex? my girlfriend shoos me away any time i go near it, i think all of her past experiences with it have her too concerned about the pain factor (i’m big, but not “huge”)

Update December 2018: Visit our Anal Sex Advice & Guide to the Anal Only Lifestyle page for a new section of this site that serves exactly this purpose.

Most good anal sex guides out there (and there are quite a few) focus on this issue more than any other. You can read through the archives here, where I’ve addressed this a number of times in the past, as well as this recent post.

Fundamentally, the key is a combination of lube, gradual warmup and increase of size over as long a period is necessary, and patience. You start with small toys and/or fingers, and slowly increase the size she can comfortably fit, stopping if anything is painful and trying again later. The amount of time varies wildly from person to person, with some able to painlessly go straight to anal sex and others needing weeks or months of training first. Everybody’s different, but with the right practice/training nearly anyone can experience painless anal.

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