Christmas in the Heir (A Locktime Holiday Original)
It always started with the two of you celebrating a big deal.
Then it would escalate to a high-stakes bet on a local game or something –– the first one ever was "office maid for a day" and you don't remember the game itself but you knew it was close. She tried to add in at halftime that you would have to wear a french maid outfit if you lost, and when you balked, she sweetened the deal with "...and if you win, I'll have to do *anything* you tell me to do for a whole day."
You agreed, knowing that 1) this would be a fun opportunity to humiliate her if you won, and 2) that Kenzie had *never* swallowed cum. She *hated* it more than anything.
By the last 30 seconds of the game, she was up by a score, and scrolling through the different maid outfits online that she would be making you wear, but in a miracle play with 15s on the clock, overtime was forced, and you won on the first play of sudden death.