Anonymous: Trying to be “awesome”. In fact, already halfway there as we now have more frequent anal. But one thing is holding us back. You seem to be the anal guru so perhaps you can help. Naturally I like to go balls deep in my wife’s ass but she often reports pain, and it does feel tight round the head of my cock like a band. Why is that and what can I do to alleviate that? We do lots of prep and foreplay so I assumed she was relaxed, and entry is always okay. Anything we could try?

The rectum averages about 4.7 inches in length, from the anus to the bend into the sigmoid colon, but it can vary quite a bit from person to person. Someone with a shorter rectum will have more difficulty taking a longer penis to full depth. Pain when unexpectedly hitting the bend at the end of the rectum is not uncommon.

It is possible, however, to temporarily straighten that bend and be able to take objects significantly deeper. The best way to do this is with a relatively small (1″ diameter is often good), very flexible dildo, some lube, and patience. Work the dildo in as far is it will comfortably go, then gently push past that limit and back off. Keep doing this, slowly increasing the depth, and you should eventually be able to move past the bend and into the sigmoid colon with little discomfort, but it will likely still not be straightened out much. Move the dildo partway out until it’s only inside the rectum again, then push it past the bend again, and repeat for a while until it moves past easily. Now try it with your penis. This straightening does not last long, so it’s something you’d need to do as a regular part of your warmup session, but some people come to like the sensations of deep anal play on their own, so it may be an enjoyable process. You may also just try doing this with your penis instead of a dildo, and going very slowly in an attempt to loosen and straighten the bend so you can comfortably fit balls deep.

Note that while the rectum is generally free of any feces except immediately before going to the bathroom, there is a higher chance of encountering feces as soon as you enter the sigmoid colon. That bend, in part, serves as a sort of valve to keep them from entering the rectum until it’s time. It’s not necessarily a major issue, but be forewarned of the possibility of encountering something unwanted.

Finally, a simpler possibility: try a different position. The rectum changes length somewhat in different positions, and you can often get the deepest penetration with her on top.

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