Double entry or double penetration of the anus is more challenging than a single penetration. For a top, it is more a challenge because you have two erect penises competing for the same space inside a bottom's rectum. For a bottom, it is also a challenge, but with the added potential for greater discomfort and pain if not done correctly or sanely.
So, yes, it is physically possible to double penetrate someone's rectum. It presents a challenge to both tops and especially the bottom. Comparatively speaking, I should also point out that the practice of fisting also presents a similar challenge.
I like a good challenge once in a while just to break the monotony of routine. But, there are some challenges that are not worth the discomfort and pain those challenges pose to the inexperienced or faint-hearted.
Be very careful, exercise good judgment, and play safe.
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