A common Establishing Character Moment. A man (and it's almost always a man) walks into a room, arms intertwined with those of two ladies, showing what a stud he is. Conversely, the ladies may get on his arms mid-scene just to imply that everything's goin' pimpin'.
The Japanese call this trope also "a flower in each hand" (両手に花, "ryoute ni hana").
A more unlucky fellow will have this lead to a Lover Tug of War. Often overlaps with In Da Club, Hookers and Blow and the Paid Harem.
Beauty and the Beast : the special edition has the Re Cut song "Human Again" in which Lumiere sings that when the spell is broken: "I'll be cooking again / be good looking again / With a mademoiselle on each arm."
In One Piece, during one of Boa Hancock's Bishounen!Luffy daydreams, she imagines Luffy like this with Nami and Robin once he mentions their names.
At one point in the Fishman Island arc, Brook comes out of a cafe with a pair of mermaids hanging off of him in this fashion. He is a rock star by this point in the story, after all.
Iono the Fanatics: a Yuri Genre example. On the first page of Chapter 0, Iono can be seen with two members of her yuri harem on each arm.
Saki: One of the shots in the opening involves the female titular protagonist having Nodoka grabbing on to her left arm and Yuuki grabbing on to her right.
Variant: In Catch Me If You Can, Frank Abagnale strolls through an airport in full pilot uniform and surrounded by a gaggle of excited, giggly stewardesses. In this case, though, the aim is to distract all the FBI agents looking for him.
Rent: A Rare Female Example. At the end of "Tango: Maureen", the bisexual title character walks away with a guy and girl on each arm as Mark and Joanne look on.
In The Big Picture, Nick, feeling low, imagines himself in a 1940s-esque picture, sitting in a bar lamenting how he used to come in there with "a broad on each arm and a bankroll that could choke a hippo," but now he can't even get the bartender to give him one more drink.
Literature
There's a variation in one of the ElfQuest novelizations, where villainess Winnowill has a guy on one arm and a girl on the other.
Daisy Miller: 1880s Europe's local Strange American Girl finally goes too far when she walks down a street in Rome with a man on each arm! One of them is the protagonist who, unlike Daisy, is painfully aware of the awkwardness of the situation. It causes a scandal.
Anansi Boys: Spider does this with an entire crowd of women; his brother Lampshades this by saying it shouldn't be possible.
The Eye of Argon introduces Agafnd as having "a naked wench seated at each of his arms."
During Wedge's Gamble, Corran Horn, undercover on Coruscant with some other Rogues and Rebel agents, tours the Imperial palace in the company of two women, aware of what it looks like and pleased at the jealousy, because both are tall - taller than him, actually - and striking. Of course, one's one of his wingmates and the other is from Intelligence and a ranking officer. Being thought of as arm candy is useful.
Gossip Girl: The first time we see Chuck Bass he is sitting on a couch with two of Blair's minions, Kati and Iz. In the next episode we first see him waking up in bed with one woman on each side of him. He is then continuously seen with two women at a time, when he's not fawning over Blair. Apparently, twins find him.
In one of the earlier seasons, Xander enlists Buffy and Willow to fake this with him. He's trying to make Cordelia jealous. They play along.
Later, the recurring Buffy character Andrew turns up on Angel with a woman on each arm. Since he'd been heavily implied to be gay in the past, some fans found this annoying. There have been two different explanations given for this change: Joss has blamed it on last-minute changes to the episode, saying it was supposed to be Dawn with a gender-swapped version of this trope, and the other story was that it was originally supposed to be a larger group of men and women meeting Andrew, meant to give a general impression of beauty to contrast with Andrew's earlier characterization as a social outcast, that was shrunk to just two women due to a misreading of the script.
The Star Trek: The Original Series episode "Shore Leave" ends with the revelation that all the strange occurances have been just illusions; McCoy appears (having been seemingly killed) with a lady on each arm.
The Office: Done so Michael, Ryan, and Dwight can get into a club.
Hustle: Danny Blue has a scene in episode two of the first season where he's accompanied by two female flight attendants, as a quite obvious Shout Out to Catch Me If You Can (mentioned above under "Films").
Glee: When Sam goes to the prom with Rachel and Mercedes (they both went with him because he thought he wouldn't be able to afford it), they are clearly invoking this with their prom picture◊.
Music
The AC/DC song "TNT" makes a reference to this, along with several other tropes among the Badass vein.
The Beach Boys song "Surf City" includes the line "Two girls for every boy," but it might mean something different.
'Killer' from Beetle Bailey — frequently. In one case, Beetle and the others arrive a bit too late for a party, and find Killer showing the length of his arms with two ladies on each arm!
In a Farley strip, Farley is recounting to Bruce the Raven a dream he had in which he had A Lady On Each Arm.
