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1.
Any sort of issues related to and/or involving semen. This can include cum in the face/hair, the inability to cum, cumming too fast, or the ever-dreaded cum in the pants.
"So we were hooking up last night, and he came in his pants." That's a real cumundrum!
by 123sober October 06, 2010
 
2.
The conflicting feelings of not knowing where to deposit your load.
She told me to cum on her ass, but her tits were amazing. It was a total cumundrum.
by Sub 20 August 21, 2013