A Calamari Cock Ring is a ring worn around the penis, usually at the base but made from calamari.

However, If someone calls you this - it typically means they don't have a high opinion of you.
Person 1: How would they view me? Behind closed doors, are they of the opinion I'm the real deal, or in training?

Person 2: So? - Well I think they have a lot of time for you, but there may be certain questions.

Person 1: Oh, shit.

Person 2: Well, you know, they think they're hot shots. They make hard jokes.

Person 1: As in?

Person 2: Well, sometimes when you were absent they used to refer to you as "the calamari cock ring. I don't even know what that means.

Person 1: I think it means they think of me as a cock ring made from calamari, Frank, it's pretty self-explanatory.
by Airbar August 7, 2018
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