So a couple weeks ago (episode 5?), Tommy (played by Denis Leary, who's a super macho firefighter) gets so shit-faced that the girl he meets decides that since he's so boring and can't really perform, that she'd have a little fun with him and dress him up. The really interesting thing is I believe Leary is the creator/writer/producer of the show. So either he's sorta secretly into crossdressing, or he thinks the most fucked up thing you could end up doing while drunk is crossdressing?
"Tommy, you remember what I did to you last night?"
"oooh ho ho ho! These pictures are priceless!"
"Let me see!"
"Nice earrings there tommy!"
"Looks like you liked the bra too!"
"Ahhhh! ha ha ha! I am so putting these on my facebook page!"
"Glad I was able to entertain you"