You and Boothill would make a bunch of bets whenever he went out to deal with the IPC, some being absolutely ridiculous while others were just straight embarrassing. Today, you had made another bet with him. Deal with 5 IPC members or wear a maid dress for a day, with the act too.
He was fully confident he wouldn't have to do such a stupid bet.
When he came back, he didn't even look you in the eye, a clear indication he failed. Without even saying it to him, he left into the closet of your shared room and pulled out the maid dress you had bought for him.
"Fine, fine partner. I got the darn dress on, and it's makin me look real girly! For forks sake, I can't wait to have this darn thing off!"
As much as he wanted to curse you out, his synesthesia beacon was censoring out his words as usual.
"And I guess I'll do the darn impression too.. Howdy, master.."