playing off the last analogy about landing his “big plane” on her “little strip.”
If the “plane” (penis) is serviced (sexed) well he will “leave a tip” (semen.)

when you put someone in a headlock you put both of your arms around their head and squeeze.

A double entendre in the sense his woman gives him dome grabbing his “head.”

“Swag in the bag” could mean either:
1. The hottest fashions in the shopping bag he treats his girl with.
2. His balls in his scrotum that keeps her wanting the D.
“She like that cockiness” is a play on words in the sense that in reality “she like the cock(iness).” Since he “please her properish” it can be assumed that he gives her what she wants.

“Hut” is a sound used in football (among other things) to accent a syllable. “Hut one, hut two, hut three” can be used as a preface to the quarterback saying “hike” which is a signal to go. The title of this song (“Pigskin”) is filled with football analogies.

Gambino has so much money he is willing to give it away freely. A “milli” is reference to the lil Wayne song of the same name [http://rapgenius.com/Lil-wayne-a-milli-lyrics] and Teunchi himself is referenced when he says he’s “not Lil Weezy.”
Even though he isn’t as well known or respected of a rapper, he still has a ridiculous amount of money making his pocket size “silly.”

“the goods” in this sense could either mean the D, or more likely the stuff that he can buy. Both his main chick and his side chick get the goods because they’re both looking “muy bueno” which is Spanish for “very good.”

a reference to Benny Benassi, an Italian DJ known for his techno works

Seemingly a jab at the group 3OH!3 (also based out of Boulder, Colorado) best known for their hit single “Don’t Trust Me.”
https://www.youtube.com/watch?v=mdB3Oyd5HtU
The bridge to the preceding song contains the lyrics:
“Shush girl, shut your lips. Do the Helen Keller, and talk with your hips.”
Confronting male arrogance would be taking a stand to show that a woman is more than just a sexual object for a mans pleasure. The same point of view that Helen Keller actually had.