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."
The anime adaptation of Infinite Stratos has Ichika in this exact situation, coerced to escort two of his close classmates to the cafeteria.
Sakura Trick inverted it in two dimensions—a Schoolgirl Lesbians example. At the end of their first day in high school, the slightly aloof Haruka noticed her old friend Yuu under this status. Haruka immediately has a Heroic BSOD, seeing her "special spot" has been taken by others, and ran off to another classroom. This was resolved by the two agreeing to do something to prove they're really special to each other: The Big Damn Kiss.
The TV version of Macross Frontier, Aruto saying You are the two wings of mine! to Ranka and Sheryl, and they don't seem to particularly oppose to the idea. In the Movie version, this is averted by somehow pairing Ranka with her own biological brother instead.
Subverted in a Tim Traveller story. Time decides to see what his life will be like in the future, and sees himself pulling this off as a young man. Then the girls' boyfriends appear and beat his future self up.
Madhouse Comics Digest #5 included a "Monsters from Outer Space" article which said that five-armed Plutonians were widely considered the best lovers in the known universe. The Plutonian depicted had a girl apiece on four of his arms and was using his fifth arm to phone potential dates for the following evening.
Bruce Wayne does this in Batman Begins, then does the same thing with three women in The Dark Knight. However, he only does it because Alfred told him to behave like a Rich Idiot with No Day Job, so that people don't start thinking about his activities and jump to conclusions. Alfred actually had to explain what he means, as Bruce has been out of touch for a while.
Elsewhere in the Batman franchise, Two-Face in Batman Forever has Sugar and Spice - Sugar for his healthy, 'normal' side, Spice for his twisted, acid-scarred side.
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.
Invoked in the first Charlie's Angels movie to crash a private party; two of the Angels get in by being with Bosley, and he gets in due to this trope (and becomes worthy of the host's attention besides).
In Wall Street: Money Never Sleeps, Gordon meets Bud at a fundraiser many years later. Bud has since become a billionnaire and retired and shows up with two ladies. Naturally, the ladies don't get any lines or even names, but this is partly due to Bud himself appearing only as a cameo.
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 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.
In Sidhe Devil, Doc leaves a party with Ish on one arm and Gaby on the other. The three of them invoke this trope to hide the fact that Doc is about to fall over from magical exhaustion.
The Brady Bunch: In his autobiography "Growing Up Brady," Barry Williams recalls filming of the episode "Mail Order Hero," the Season 5 episode guest-starring New York Jets quarterback Joe Namath, and writing that he pictured the trope being enforced as he came onto the set (i.e., several women on his arms, with dozens of other young women following behind). Averted, however, as Namath – although he was a bachelor at the time – was in extreme pain and was accompanied by only a small entourage that included his agent.
Done in NCIS to get three female NCIS agents into a club, after discovering that McGee was the "bouncer-worthy" one of the group.
And in the Mirror Universe, Jake Sisko comes across Nog (now running the bar after the demise of Mirror!Quark) with a sleazy-dressed Dabo girl on either side of him. He tosses one to Jake, who isn't all that bothered. Until Dad walks in.
A Gender-Inverted Trope in "Way of the Warrior" Dax enters with a shirtless and well-muscled holographic masseur on each arm. She also offers one to her companion — Kira in this case, who is reluctant to indulge in Kiss Me, I'm Virtual pleasures.
Star Trek: The Next Generation. Happy that the Continuum has given him back his powers Q materializes a mariachi band on the Enterprise bridge and a couple of women on either side of Commander Riker. Being more than capable of getting his own, Riker indignantly refuses Q's "fantasy women", so Q materializes them on Worf instead.
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 occurrences 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").
Supernatural. The Reveal that an apparently innocuous character is The Trickster is when he materializes two women in lingerie to join him for dinner. Later he offers them to Dean as a bribe to leave him alone. Dean is tempted, but turns down the offer.
Farscape. In "Dog With Two Bones" Crichton has an Imagine Spot re marrying Aeryn on Earth. At his wedding party, a tuxedo-wearing D'Argo is clasping a pair of human beauties.
Dave & Sugar: Several publicity shots and album covers of this late-1970s/early 1980s country music trio – lead singer (and one-time Charley Pride prodigy) Dave Rowland, accompanied by two female singers – had his two female bandmates (the "Sugar") hanging on each arm.
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.
The liner notes of a John Lee Hooker compilation tell of the writer having seen Hooker walk into a club with a white suit, a white cane and a young white girl on each arm. "Between this and the image of a blues singer playing on his porch, I prefer the former; this guy knows how to have fun."
Psy does this in one scene of his Gangnam Style video. With debris flying towards him and his girls.
Dean Malenko. After all, he was called "the Ladies Man" for a reason.
The Magnificent Muraco: During the height of his heel run in the mid-1980s, Muraco cut a nasty promo on Hulk Hogan on a beach. Two sexy, bikini-clad women were hanging on each each arm, smiling the whole time as Muraco ranted about how he would beat Hogan to within an inch of his life, then take his WWF World title.
This became Mr. Big's standard pre-fight animation, from King of Fighters '96 onward, which is the reason gamers believe that one of his syndicate's operations is prostitution.
In Sinfest, Satan commonly appears with a succubus on each arm. Less now that the succubi have personalities.
In The Order of the Stick: On the Origin of PCs, a newly-jailbroken Belkar is just musing that life couldn't get any better when happens upon a sign saying, "WHORES: 2-for-1 Sale!" The next panel is the three of them walking off like this.
Pietro from X-Men: Evolution shows up to a dance with a girl on each arm... And two girls besides them.
An episode of Tripping the Rift had the president of a planet in this situation, but its hat was homosexuality, so they were guys(he also makes a remark about his stay-at-home husband). Turns out he's really straight, which is a crime on said Planet of Hats.
Spider-Man and His Amazing Friends: In Season 2's "Along Came a Spidey," during the flashback, a teen-aged Flash Thompson mercilessly taunts Peter Parker; at one point when the two have an exchange at the beach, Flash – two beautiful teen-aged girls draped on each arm – kicks sand in "Peter Puny's" face and laughs evilly as he walks off. The two girls giggle, thinking Flash to be cute and funny.