Put his boots on

Used to describe someone (typically a male) who has apparently completed a sexual conquest. Derived from the original Star Trek televison series in which, on several occasions, Captain Kirk obviously bedded the hot woman who is never seen again. ...Alien chick in 60s go-go/hippy fashion apparel primping while Kirk pulls his Star-Fleet-issue black leather boots on.

A smarmy, smug man walks out of bedroom at a loud party. "Observe! Manfed has just put his boots on! Matilida will be out shortly!"

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Fingers in his ass

Fingers in his ass originally was a joke from both the undertale and danganronpa fandoms and features the characters Sans Undertale and Nagito Komoeada.

“Fingers in his ass, fingers in his ass, Kanye west he likes, fingers in his ass.”

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Hi, welcome to Chilli's

It's a mad ass vine. “Hi, welcome to Chilli’s” is a phrase that became popular on social media with a Vine by Adam Perkins titled “I’m really proud of this one”, which was posted March 2015.
In the Vine, the Viner walks into a bathroom, wearing only boxer shorts, and states, “Hi, welcome to Chili’s.” but skrrt, vine is dead.

Hi, welcome to Chilli's
*wanting a small tattoo that has a lot of meaning* "Hi, welcome to Chilli's"

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Trap his ass

Be so irresistible that he has to commit to you.

Oh my god, did you see that guy? I’m gonna trap his ass.

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Put His Foot in It

Idiomatic phrase meaning to make a mistake - having stepped into a pile of manure metaphorically speaking.

When he asked her if she'd put on weight, he really put his foot in it.

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beat to his socks

An old black phrase to refer to extreme poverty.

Man, Richard used to be one hep cat; now he's on smack and beat to his socks.

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grab his cock

A phrase used as a smart ass answer to all questions. Similar to a barrel roll.

Girl:I really like this guy, but I don't know what to say to him.

You: Grab his cock.

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