You and Wilbur have been friends for a while now, you even lived together. Unbeknownst to you, he had the biggest crush on you.

Deep down, you liked him too, but to cope with those feelings that you wanted to keep hidden deep down, you'd sleep with other people

Because of this, Wilbur would refuse to sleep until you'd get back from whichever house you went to that night

Because sex sells, he knows that.