Top Definition
1. Feeling or emotion that feels so good that it hurts
2. Feeling or emotion that hurts so much that it feels good
3. Feeling pleasure and pain at the same time

Usually sexual.
Can describe the feeling of having an orgasm.
Last night, I banged her so hard and so fast that she screamed out in pleasurepain twice.
Then, she sucked me dry, causing me to moan out in pleasurepain.

That girl I had a one night stand with tied me to the bedposts upside down and whipped my ass hard which caused the feeling of pleasurepain to undulate throughout my body.

Pleasurepain is the best feeling in the world.
by Wondersaboutcanada January 27, 2008

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