The act of masturbating to something sexually displeasing, usually over disgusting pornography or someone considerably unattractive. The challenge will be completed if one forces oneself to cum.
1:

"I did a challenge wank over 2 girls 1 cup last night"

2:

Billy: I challenge wanked to Olga's profile picture last night
Sam: No way, that's disgusting! Did you complete the challenge?

Billy: To my disgust, yes!
by shalabon January 6, 2015
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A wank with some challenges.

For instance, your phone may be nearly out of battery, so you have to hold your phone and charger at a particular angle to keep it charging. The movement will dislodge the charger at the worst possible moment, with the risk of phone dying being a real threat.
"Bruh I had a logistically challenging wank last night, Jesus Christ it was more difficult than doing the Christmas shopping
by cancerisnotaverygoodthing November 21, 2018
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Wanking carried out whilst riding a bicycle through various villages in East Anglia. This can be a solo or team sport. Points are gained for how many villages you manage to wank in.
x: Did you have a good weekend?
y: Bit sore....cyclo wank challenge this weekend, 10 villages mate! Check that out!
x: Fucking hell I might try that with the wife this weekend...
by Dicksplatlia May 17, 2007
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