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This is going to be a bit embarrassing.

Whenever I 'wink' my anus ie. contract the external anal sphincter or squeeze (as if I'm on the toilet), a small dip appears above it. From afar it looks like two anuses except one smaller. When I'm not contracting it looks fine. Do I have an anal fissure?  It is also purple all around as if bruised. Any help would be appreciated.

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Without seeing your anus and inside the anus from what you are describing is a hemorrhoid.  A hemorrhoid is an engorged mass veins that can be inside and/or inside the anus.  Although uncomfortable, this condition can be eaasily treated.  On the other hand to get the diagnosis of a fissure or fistula through the anus and inside the rectum you need to see a physician.  The more severe diagnosis are more painful and you would get bright red blood when you wipe.  You could also get blood if you have hemorrhoids.  Your symptoms will not just go away Try seeing a Recto-Anal Specialist.

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