Plum (Shimbo's compact persocom, designed to resemble the laptop), tries to hide in the cleavage of Chi, because Hideki (with all the screaming around) is scaring her.
Yumi keeps her keychain-sized persocom in her cleavage (At least in the manga).
009-1: 009-1 has hidden the monkey with the implanted memory (containing data about a weapon of mass destruction by the Eastern Block) between her breasts when jumping out of a shuttle set to explode when it reaches a certain altitude.
Sha Chi from Penguin Musume hides a katana (of all things) between her breasts in one episode.
Takada Kiyomi keeps a page from the Death Note in her bra. Similarly, Light (in volume 9) discusses with Ryuk keeping Misa's notebook in case he needs to relinquish ownership of his again so he won't lose his memories by binding it to his chest with a corset.
Haruna from Kore wa Zombie desu ka? hide the secret scroll that Maelstrom borrowed from Ayumu between her umm.. cleavage. Lampshaded by Ayumu that she had to have bigger breast to hide it there.
During one arc of Black Lagoon, Revy ends up hiding the documents they have to deliver in her shirt, only revealing this when they give them to the CIA agents sent for them. The agents then complain that the documents are sweaty.
In an early arc, Shampoo hides an antidote shampoo down her shirt◊ and then dares Ranma to retrieve it. When bartering an antidote or power item with Ranma for a date, she tends to keep them there too, to prevent him from stealing and bailing. She once hid a kitten in there, but that was to scare Ranma into accepting the date (Ranma's an ailurophobe).
Similarly, Kodachi has kept items in her bra more than once.
A mirror-duplicate of female Ranma hid a magic compact in her cleavage once. Naturally, the real Ranma didn't even think twice about stealing it.
Though she doesn't actually have a cleavage worth mentioning, Pan muscles her way into the first saga of Dragon Ball GT by dropping the control keys for the spacecraft she has stowed away on down her shirt. Trunk's long hesitation about whether to retrieve them or not was the cause of much (possibly unintentional) Unresolved Sexual Tension between the two.
Many suspect that Ururu from Bleach has a hidden compartment... down there◊. It's bigger than she is! Ah, the wonder that is Hammerspace.
In one episode of After War Gundam X, Ennil asks the guards preparing to kill her and Dr. Farzenberg for one last intimate moment (pretending that they're lovers). They agree, and she opens her jacket... revealing a set of flash-bang grenades, which she and Farzenberg use to escape.
A few ladies in the manga hide things (microfilm, diamonds) "down there". Busty Fujiko's among the most frequent of practitioners.
The first opening sequence for the Lupin III (Red Jacket) series shows Fujiko dropping a diamond ring in her bikini top.
An episode of the second series has Fujiko in disguise, only for Zenigata to see right through it. After revealing her, the first place he looks for a hidden microphone is in her cleavage. And he's right.
Another episode of the second series has a giant Fujiko tuck a normal-sized Lupin into her cleavage for safe keeping. It Makes Sense in Context.
In a chapter, Rito gets shrunk to roughly 4 inches tall. Lala keeps him all day in her Marshmallow Hell.
Her younger sister Momo has been shown tucking her summoning device into her cleavage.
Boota of Tengen Toppa Gurren Lagann has ridden in Yoko's cleavage on multiple occasions, including the first day they met. Kamina and Simon's jealousy is obvious. What's even funnier is that after the time skip, when Yoko makes her dramatic entrance, guess where Boota goes.
Shinkon Gattai Godannar!! takes the Fanservice knob and turns it well past eleven. Two of the characters keep their cellphones in their cleavage (though it's more like a cavernfor both of them, really). Both also happen to keep them on vibrate, so everyone knows they're getting a call when their boobs start to rumble like the kind of volcano you run away from really fast.
In Detective Conan, Kudou Yukiko carries an unconscious Conan in her cleavage while riding a motorcycle across Japan. Conan is actually Shinichi, Yukiko's drug-induced de-aged teenage son.
Sheryl in Macross Frontier drops Alto's talisman down her shirt in the 5th episode as "insurance" that he'll keep his word. And in the False Songstress Movie she keeps a taiyaki-shaped cellphone in there, which wiggles so much when it rings that is actually leaps out!
Kalifa apparently hides her key between her breasts.
Nami hides things in there rather often, including the staff she uses to fight (both before and after getting the Clima Takt). She also stored a Den Den Mushi in her shirt, which was more than pleased.
Dominion Tank Police, the animated OAV run: the Puma twins (guised in finery) take out their large heavy weaponry from their bras and underwear.
In Ayashi no Ceres, Aya keeps Tooya's dagger in her bra. It's wonder how she doesn't get cut.
In the manga for the video game Tales of Symphonia there's an omake that says that Sheena has her exsphere equipped just under her left breast.
In an omake chapter of Fairy Tail, Erza produces a lead pipe... Well, there's a reason it's on this page.
During the after party of the Grand Magic Games, Erza cheers up Milliana by pulling out Happy, Carla, and Lily from her rack.
Pokémon Special character Blue note Green in the English version is rather well-endowed for a twelve-year-old. Sabrina unfortunately found out why during her battle with her. There was no way anybody saw that coming. Blue was frozen in place, so she taunted Sabrina's "health" (read: bust size) and baited her into attacking her big, round... Poké Balls. Not a euphemism: Blue apparently padded her top with them, and the attack released her Pokémon and allowed her to escape. Unfortunately, it was edited out of the English re-release.
Merle from Vision of Escaflowne apparently has much larger breasts than viewers are led to believe, because in episode 8, she stores two boxes of Pocky, lipstick, a pager, a watch and a discman in her cleavage.
Izumi of Hayate the Combat Butler apparently keeps her cell phone here. Revealed when a guy (kitten) steals it, by diving into her shirt.
Fuu of Samurai Champloo has a pet flying squirrel named Momo, which seems to spend most of its time inside her kimono. Spoofed in an episode where two teenagers appear to be leering at her cleavage. At the end Fuu is furious to discover they were actually interested in Momo. There was also the first episode, where she stuffs some bombs down the front of her shirt, which unlike Momo are quite easily visible.
When Chypre and Coffret first ran into Tsubomi in HeartCatch Pretty Cure!, they hid in her shirt to escape from Sasorina. It works perfectly... until she creates a Desertrian.
In Futaba-kun Change!, the store clerk they meet while shopping for undies is so addicted to smoking that she has a tendency to try to sell underwear with multiple hidden compartment for cigarettes, just like the ones she wears to hide her smokes.
Princesses Gallet and Christina does this accidentally in Shina Dark when they are forced to leave the treasury/labyrinth of doom without any treasure... except what accidentally got stuck in their cleavage, much to Noel's jealousy.
Kana from My Lovely Ghost Kana is the eponymous ghost. Being a ghost allows her to drop the temperature on the room that she's in as well as apparently cool a can of beer to the perfect temperature by putting it in her ghostly cleavage and rotating it slightly.
In Sekirei chapter 62 Matsu pulls a tracking device out of her cleavage.
In one chapter of Sayonara, Zetsubou-Sensei, Chiri comes to clean Nozomu's house, and wants to straighten things so there is less "dead space". Nozomu comments that she has her own dead space, wearing a bra that's too large for her. She responds that she uses the space effectively and pins him to the wall with knives. (During this scene, Nozomu specifically references Fujiko of Lupin III.)
In Saki, Yuuki, after losing a practice match, accuses Nodoka of hiding mahjong tiles between her breasts.
The "Rodomontade" card in Munchkin Bites 2: Pants Macabre, which allows you to hold an extra card, depicts a card held in such a manner.
In The Spirit, Satin, a thief, hides a stolen medallion down her bosom. Unfortunately for her, the title character chooses to turn her upside-down and shake it out, rather than reach in.
In an issue of X-Men, Storm and Nightcrawler were enjoying a night out when she — wearing a revealing evening gown and no purse — suddenly pulls out a cell phone. When Kurt asks where she had been hiding that, Ororo responds, "My secret."
Jack of Fables #18: Hillary Page reveals she has the missing piece from the map to Americana. She stuffs it down her shirt for safe keeping.
At the end of Secret Six #7, it's revealed that Scandal has Neron's get out of hell card stuffed down her top.
In The Adventures of a Lesbian College School Girl, Jennifer hides the key to Petra's diary in her bra. Petra retrieves it with her teeth. Given the title, you can probably guess what this leads to.
She wasn't hiding it, but Madame Mirage once showed off by holding her pistol (by the barrel, grip facing outward) between her breasts. She even moved around a little to emphasize the fact that it was securely lodged in there. She's also seen to store a small video screen down there.
In issue #181 of Knights of the Dinner Table, Sara gets hold of the infamous cursed die Fitz and keeps it away from the rest of the knights by dropping it down her cleavage and zipping up her catsuit.
Modesty Blaise once used her bra to smuggle a saw into prison in order to create a rather elaborate escape plan.
At one point in thisHarry Potter fan work, Hermione stuffs Ron and Harry's wands down her blouse to keep them from hexing each other. However, Ron doesn't think that this is really a hardship. Unfortunately, nothing happened, which could inspire Fan FicFan Fic Fuel
Danny Phantom's Ember  somwhat subverted in that the object in question is larger than her breasts.
Gensokyo 20 XX: Kaguya isn't concealing a knife in her cleavage, but rather between her butt cheeks. Played straight in Mokou's case, in that she carries her cigarettes in her bra.
In Who Framed Roger Rabbit, when Judge Doom tells his henchmen to frisk Jessica for Marvin Acme's will, Greasy Weasel reaches down her ample cleavage to do it (and in order to cop a feel), but all he gets is his hand caught in a Bear Trap.
Willie hides the cure to the poison that infected Indiana Jones there in Indiana Jones and the Temple of Doom. Later, while Indy attempts to retrieve and Willie mewls, "I'm not that kind of girl!", Short Round comments: "Hey, Doctor Jones, no time for love! We got company!"
This trope is frequently used by Bernadette Peters. She used it in Pennies from Heaven... and then in the film version of Annie... and then once more in Woody Allen's Alice... and then again in the TV remake of Cinderella... the list is endless. Well, that's no surprise, given that she probably has a lot of room in there.
In the awful Thunderbirds movie, the Hood's female assistant stuffs some of the stolen jewellery down her cleavage when no-one is looking.
Pirates of the Caribbean: Elizabeth Swann and the Aztec medallion that — due to a gold chain's magical length-fluxuating ability — would pop down from her cleavage into her corset for a handy spider hole. Even Barbossa could not figure out whence Miss Swann pulled that hefty blunderbuss in At World's End. Jack, however, mocked this, given Miss Swann's figure.
Jack Sparrow: "So unless you've got a rudder and a lot of sails hidden in that bodice—" (scans her briefly) "— unlikely..."
In The Saint, a female scientist hides the notes to her invention on scraps of paper tucked into her bra. So the title character seduces her in order to get them.
In Kiss Kiss Bang Bang, Perry hides a gun down there with a fairly good justification — he knows it's the only place he'll never be searched. Doubly so because he's gay. Another male character uses the same justification in The Long Kiss Goodnight. Except without the "gay" part.
In It's a Mad, Mad, Mad, Mad World, Ethel Merman's character drops the car keys down her cleavage, prompting the male characters to turn her upside down and shake the keys out. Parodied and subverted in one master stroke.
In Batman, Vicky Vale attempts to conceal the film containing a picture of Batman unmasked in roughly that neighborhood, if her dismayed grab at her left breast in one scene is any indication.
In Batman Forever, Bruce Wayne asks Sugar (one of Two-Face's babes) how to turn Edward Nygma's machine off. He takes the glowing green battery from her and goes in, and then Sugar produces a second, identical battery from down her cleavage and switches it on again.
Jennifer Connelly again in The Rocketeer. She hides the stolen reverse-engineered plans of The Rocketpack she finds in a secret Nazi bunker.
In the film adaptation of the comic book Barb Wire, Barb (played by Pamela Anderson) hides a pair of contact lenses in a little tube down her cleavage. Then it turns out they were fakes and she was wearing the real ones. Still, the compartment stands.
Adrienne Barbeau tucks her license into her bra in The Cannonball Run as part of her strategy for beguiling cops out of giving her speeding tickets. It works, too... until she's pulled over by an equally busty female police officer.
Adrienne Barbeau also uses her Compartment in Swamp Thing.
Notably averted in Diamonds Are Forever when Tiffany Case tries to conceal a data cassette in her bikini bottom. Needless to say it's glaringly obvious there, especially since the Big Bad forced her to wear the bikini specifically to prevent her from concealing anything. Well, that's the reason he gives, anyway.
A View to a Kill: Pola Ivanova smuggles away an incriminating tape down the front of her robe.
In Mission: Impossible II, Nyah attempts to hide the expensive necklace there. Ethan then forces her to give it back, right in front of the head of security.
Mad Money, where the trio stuffs every single scrap of clothing with money.
There was interesting subversion in an early Jet Li film. In it, Jet Li's character caught a female reporter recording something sensitive. He goes up and asked her for the tape. The reporter promptly dropped the tape down her blouse, thinking he won't search her there. He didn't, he just grabbed her legs, turned her upside down and shook until the tape dropped.
In Bad Boys, Tea Leoni's character manages to hide a handcuff key in her bra and uses it to escape at the end. The mook guarding her sees her reach for it but doesn't think to check her.
In the 1974 The Four Musketeers, Constance (Raquel Welch) got her hands on a key which she triumphantly dropped into her cleavage — having forgotten that her friends needed that key to unlock the chains and rescue her. And then, it being a very small key, it slipped further down and she couldn't dig it out. Eventually she tried jumping up and down in hopes that it would fly out.
In Don't Be A Menace To South Central While Drinking Your Juice In The Hood, the boys rush their friend to the hospital after he gets hurt in a Drive-By shooting. The receptionist makes them fill out a bunch of paperwork, giving them a pen from the front of her shirt. When one of the boys asks to get a drink of water, she pulls out a paper cup already filled.
Time After Time, Jack offers a prostitute a shiny coin. She quickly deposits it down her corset.
Inverted in Sherlock Holmes where Holmes handcuffs Irene Adler and drops the key down her breasts for another man to have to fish around for. Plus the earlier scene when Irene reaches down the the front of her dress for an envelope containing information on the case. The fact that Holmes grabs her arm and prepares to defend his life indicates she's kept more lethal items there in the past.
The Bounty Hunter gives us this line:
Gerard Butler: Something tells me I should frisk you. Jennifer Aniston: Why? Do I look like I have a weapon between my breasts?
Clue: Miss White produces a handkerchief from her cleavage. That's probably all that could fit there considering her dress. We imagine that Yvette and Miss Scarlet could have easily hidden all of the evidence away given how their attire complimented their ahem tracts of land.
Toward the end of The Running Man, Amber (who, as a contestant in the Deadly Game, is wearing a spandex bodysuit) produces an incriminating tape. Leading to...
Richards: Where did you hide that? Amber: None of your business.
In Runaways, the girlfriend of the Big Bad is scanned for tracking devices by the cops, who find one planted in her bra. A definite subversion, as it was one of several bugs hidden within her various garments, and she herself didn't know it was there.
Restoration. Robert Downey Jr. plays a 17th century doctor who is losing all his money in a shell game, and searching desperately for more. Meg Ryan is playing his mentally disturbed wife. She shouts loudly "My money's up my skirt!" much to his embarrassment. Sure enough she then produces a coin from up her skirt. And wins the game for him.
The trailer for Jonah Hex implies that Lelia keeps a knife in her bustier, but that it was taken when she was "thoroughly searched."
In the film, At the Circus, the villainess, played by Eve Arden, places an important item down her costume (she's a human fly in the circus) leaving Groucho to muse (to the camera); "There has to be some way to retrieve that without offending the Hays Office."
All About Steve. Mary stuffs a cookie wrapper into her bra, further reminding us that she is insane.
Magnum Force. The prostitute in the taxi cab pulls double duty on this trope, hiding large sums of money in both her bra and panties.
The Clark Gable film China Seas does this twice. First, when China Doll (Jean Harlow) steals half of the hundred pound note down her dress. When asked where it was, she kept cupping her breast, not so subtly. The typhoon leaves her soaking wet, but somehow the note survives intact. Later, when the ship is boarded by pirates, two of the girls in the lounge drop their earrings down their tops. Little good it does them, as one of the pirates sees them do this and with one gesture, gets them to take the valuables out again.
In Carry On Cowboy, Belle carries a gun in her cleavage.
Parodied in Laurel and Hardy's Way Out West. Trying to keep the deed to a gold mine from a femme fatale, Stanley stuffs it down his shirt. This doesn't deter her at all and she accosts the extremely ticklish Stan.
In the 2002 film Trapped, Charlize Theron's character hides a scalpel between her buttocks. She then gives a Groin Attack to the main villain with said scalpel.
Abbott and Costello Meet the Mummy: The Femme Fatale pulls a gun from her shirt. However, since she was dressed for the desert it takes opening a few buttons to get it out and putting them back when putting the gun away.
In Il Postino, the girl hides her love letters here. Given that she wears low cut tops and that she is hiding them from her mother and grandmother, the letters are retrieved in pretty short order.
An older woman went shopping, and tucked her $50 into her brassiere for safekeeping. While on the bus, a young man reached in and grabbed it, and ran. Afterwards, the police asked why she took so long to raise the alarm. "I didn't realize he was going for my money," she protested.
Redd Foxx told a similar joke early in his career, about a woman accosted by a mugger. The rather Savvy mugger figures she might have some more money hidden away, and begins to search her thoroughly. After a while, the woman tells him that she doesn't have any other money "But if you keep doing that for five more minutes, I'll certainly write you a check!"
A young woman with a cold was invited to a formal party. Lacking pockets, she put a handkerchief in each cup of her brassiere. Partway through the party, she steps aside and pulls out a handkerchief to sneeze and blow her nose, afterwards discarding the handkerchief in lieu of stuffing it back in. Later, she feels a sneeze coming on, so she reaches in for her second handkerchief. Not finding it, she starts rummaging around when she realizes the room has gone completely silent. She looks up and sees everyone staring at her. "What?" she said, "I know I had two when I started tonight!"
A comedienne had this as her whole routine during a stand-up showcase, possibly Comicview on BET. At first she started small, pulling a handkerchief out of her bra to dab away sweat while telling a story, but then the things she pulled out got increasingly outlandish, including a sandwich (that she started to eat), and ending with a bottle of wine. In case you're wondering, she was a larger woman wearing a loose-fitting blouse, so everything was fully concealed at first.
In Gone with the Wind, Scarlet O'Hara averts this trope. She thinks about hiding her money inside her, uh, bosom, when Yankee soldiers come to raid her house, but is afraid if the soldiers see it they will strip-search her, so instead hides it in her baby's diaper.
Velvet from The Malloreon sometimes keeps a small, virulently poisonous snake there. Her love interest Silk is not amused. For that matter, neither is the snake's owner. Later she keeps a bunch of them down her dress after the snake has babies. She also mentions that initially she got the creeps from keeping the snake there- she did it because she's an assassin, and it was a useful emergency weapon.
In "Trill Coster's Burden", one of Manly Wade Wellman's Silver John stories, The Vamp tucks a giant ruby into her cleavage, and tells John that if he wants it he'll have to reach in and get it; he declines, and she gets away. (This ends badly for her, since the reason he wanted it in the first place is that it has a curse on it he's trying to break.)
Discworld: Nanny Ogg keeps all sorts of things in her knickers, including alcohol and cash. But since she's a dumpy old lady, this is Fan Disservice. It helps that a witch wears several skirts, several pairs of pants, several stockings, and "knicker pocket" can only be the first layer in their underwear. But that's putting way too much thought into it.
A Song of Ice and Fire: Similar to the Xena example below, Asha Greyjoy keeps a dagger sheathed between her breasts. Being one of the few female ship captains, she's quick to show it off and refers to it as her "suckling babe".
In A&M, this causes a clerk to nearly faint, and just brings his crush on the girl full-circle.
In one of The Indian in the Cupboard novels, Patrick gets sent back in time to The Wild West and is a few inches tall. When he finds a sympathetic lady who wants to carry him around, she considers her shoulder, decides it's too slippery, and goes with her cleavage.
Tiny Gulliver in Gullivers Travels also gets a cleavage ride. He's just nauseated by the hygiene factor, though. After hearing his description of the experience, so are most readers.
In Tom DeHaven's novel It's Superman!, Lois hides a metal tag that could be used to incriminate Lex Luthor in her white cotton Gamble's brasserie when questioned by the police.
Sheen from Piers Anthony's Apprentice Adept series carries small tools in her breasts. Note that because Sheen is a robot, this is entirely literal; she actually detaches her breasts to reach these items.
In a novel based on Primal Rage, villainess Malissa is trying to taunt main character Kage with a map. She sticks it in her cleavage to keep him from grabbing it. Then proceeds to antagonize Kage with her taunts and cattiness until he loses his patience with her and grabs it anyway.
Enola Holmes uses this trope as both a means to disguise herself by exaggerating her bust for disguise purposes and hiding important items, most notably a dagger with the protruding pommel posing as a broach.
In the sequel Eldorado, Sir Percy's wife Marguerite smuggles letters from him to his League out of prison in her kerchief... or, as her husband puts it, "... on your exquisite bosom where I so love to pillow my head."
In another sequel, Sir Percy Hits Back, the Scarlet Pimpernel himself sends a secret message to Fleurette, his latest rescuee, by slipping it into her Victoria's Secret Compartment... while disguised as her prison warden, which freaks the poor girl out.
In the Land of Oz books by L. Frank Baum, the sorceress Glinda is forever pulling her wand or some other useful magic doodad out of her "bosom". She probably wins the trope because on one occasion she pulled out a magical handkerchief which turned into a camping setup for a dozen people!
Used by Rosamund in the Knight and Rogue Series to store the key to a flimsy lock, much to Fisk's exasperation and Michael's delight.
John Updike's short story "A & P" features an attractive, bikini-clad customer who pays with a dollar bill pulled from her top.
The Hollows: Rachel sticks her cell phone here for a wedding, since her dress lacks pockets. It rings loudly and rudely. Takata finds it amusing when she says she "had it on vibrate. Really."
The title character of Orlando: A Biography carries the manuscript of "The Oak Tree" in her bosom for a couple centuries before publishing.
In Some Golden Harbor, Adele and Tolvera use a false bosom used by Elemere to hide a pair of machine pistols for use in a raid on a paranoid councilor's mansion, knowing that they would be scanned for weapons on arrival, while a seemingly restrained Elemere wouldn't.
This is how Gwyneth of The Ruby Red Trilogy takes her mobile phone to the past with her despite it being forbidden.
In Margin Play, Amber carries (at different times) a business card, a thumbdrive, and a gun in her bra.
The very first Nero Wolfe novel by Rex Stout, Fer De Lance, features a young Italian housemaid who carries her money rolled up in the top of her stocking. Given that the novel was written in 1934, only a cad and a bounder would try to get to it there. (Archie does, anyway.)
In one second-season episode of Charlie's Angels, one of the Angels asks "How do you hide a gun in a bikini?" Bosley's answer? "Very carefully."
Seen repeatedly in Deadwood, HBO's Western Drama Series. The prostitute Trixie carries a tiny derringer handgun, and practically never goes anywhere without it. The weapon always stays hidden until she produces it — usually from her cleavage.
Everybody Loves Raymond: Whilst trying to keep the car keys from Frank, Marie drops them down her blouse. Frank: "I'll walk!!"
In a Dream Sequence episode of Sister Sister, Lisa hides money in her bra.
After informing Jack and Larry of the possible hiding places for a wad of money she used at first, Cindy says that she was finally able to think of the safest hiding place — inside her blouse.
In another episode, in an attempt to score some action with Jack, Lana takes some money off of him and puts it into her cleavage, telling him to "make a withdrawal." Jack obviously isn't amused, but Chrissy finds it hilarious, saying, "It's a treasure chest!"
A hilarious misunderstanding in Coupling (best not to go into exactly what said misunderstanding was, for fear of text walls) led to a discussion about why men don't smuggle. One given reason was a lack of "concealment crevices"...
Parodied in Married... with Children when Marcy, notorious for her flat chest, attempts this trick — and the object falls through her shirt and onto the floor. Played straight with Peg, though — who should be the posterwoman for this trope.
iCarly: Conversed in "iMake Sam Girlier"; a bully shoves french fries down Sam's shirt. After Sam beats her up, she pulls a fry out of her blouse, eats it, and remarks that it's a pretty good place to keep french fries.
"War Stories": Zoe successfully attempts to ransom back her husband Wash and Mal from Niska. After averting Niska's attempt to pull off a Sadistic Choice by picking her husband when Niska says the ransom is not enough for both men, he re-evaluates saying that the ransom was really a little too much and has his Dragon cut off Mal's ear which Niska then hands to Zoe wrapped in a handkerchief. Zoe calmly takes it and carefully tucks it into her shirt (though not her bra). Although, being the Captain's faithful sidekick, Zoe might have felt that shoving it into a pocket was simply disrespectful.
In "Shindig," Mal lifts a big wad of money off a guy in a bar. He gives it to Inara for safekeeping... and she immediately sticks it in her top.
Smallville, "Odyssey". Lois concealed a flash drive with incriminating evidence on Lex in this area.
Dollhouse, "Grey Hour". Bank robber-imprinted Echo loses her memory of what she's doing, so the Dollhouse uploads the same imprint into Sierra in an attempt to walk Echo through the heist. Sierra tells Echo that she has a bottle of resin on her person. When Echo can't find it, Sierra remarks "Bra's a good place".
V.I.P. has Valerie Irons (Pamela Anderson) hiding everything the propmaster could find, but she's outshone by Kay Simmons (Leah Lail), who had a laptop (or perhaps toptop) computer hidden there.
Larry's agent Jeff in Curb Your Enthusiasm is accused of having a small penis by an ex-mistress, who works as a maid. Jeff explains that in fact it's the opposite, she has a very large vagina. Larry suspects her of stealing a baseball, and when he loses his cellphone tries calling it. Hilarity ensues.
A skit on Carol Burnett's variety show back in the '70s had her character pull things needed for songwriting out of her cleavage: paper, pencils. When it's pointed out that the pencils aren't sharpened, she sticks one back in — and the grinding sound of an electric pencil sharpener is heard.
Variant in Star Trek: The Original Series episode "Charlie X". Charlie shows Yeoman Rand a "card trick" where he throws the Ace of Clubs over his right shoulder and Yeoman Rand, sitting on his left, gives a startled expression before pulling the card from out of her low-cut uniform.
In the Chuck episode "Chuck Versus the Three Words", Sarah keeps a knife in her bra. Notable in that the it isn't clumsily concealed in between her cleavage but is instead housed in a special sheath near the straps.
Due South, "All the Queen's Horses": Fraser and Thatcher are handcuffed together in the train's horse box, but Fraser may be able to pick the lock using one of Thatcher's hairpins — once they have it. Their hands are unusable because they're cuffed in an inaccessible place, so Fraser has to remove the hairpin from Thatcher's hair by mouth... but then he drops it. Guess where it lands? He then has to retrieve it, again by mouth (but only after asking permission of his superior officer). Thatcher's expression as he recovers the would-be lockpick is priceless.
Xena: Warrior Princess: Xena keeps a knife down her cleavage. Well, she keeps weapons everywhere she can. Gabrielle's efforts to copy her are hampered by her "less impressive" assets.
From Bones, while pretending to be a carefree married couple with Booth and trying to gain some information off some guys, Brennan walks up to them and casually takes out a wad of cash from her low-cut dress.
Done by Victoria Justice's character. How suitable. Lampshaded in the episode "Freak the Freak Out", when an exhausted and sleep deprived Tori blows her nose, and, unable to find a garbage can, just shoves the tissue down her shirt.
One episode has Cat keeping candy in her bra, which she offers to her friends.
In an episode of Happy Days, a female gang have captured Richie, Ralph and Potsie because Chachi had been dating the younger sister of the gang's leader and dumped her. The leader puts the key down her blouse and taunts Richie, "Come and get it, if you've got the guts!" Later, Richie has the key, and he puts it down his shirt and says the same thing, so the gang leader rips his shirt off.
Richie: That is a gutsy lady.
On M*A*S*H, Margaret and a friend from nursing school talk about how they kept cheat sheets to their nursing exams in their bras.
In a first season episode of Night Court, the gang received a sealed file containing Harry's criminal record. To keep Dan from opening it, Lana stuffs the file down her blouse. It didn't fit very well in there.
In the All in the Family episode "Mike's New Job", Edith does this with a slip of paper (on which is written the phone message that will lead to Mike and Gloria's move to California) to keep it away from Archie. Archie doesn't hesitate to go in after it.
Alex Hunter from White Collar hides a knife here. She and Neal use this to escape the Big Bad's Death Trap in one of the season finales.
In Battlestar Galactica, D'Anna Biers hides a video camera tape in her shirt and hands over a fake one to be confiscated.
In "Hampton Wick", there is a sequence in which the female protagonist works as a pickpocket. She is shown stealing watches, wallets and other valuables, hiding them in her blouse, and later extracting them to give them to the crooks who employ her. After a few iterations, she is seen with an uncomfortable expression on her face; then she drops a stuffed alligator onto the heap of loot.
The tendency of women to try and use this trope for shoplifting was referenced in this skit (about the 3:50 mark).
Officer: At one stage I had cause to approach a woman who I was pretty certain had been smuggling out bars of soap down the front of her blouse. Eventually, of course, she made a clean breast of it.
In Community episode "Cooperative Calligraphy", Annie is accused of hiding her pen here. To rule it out, everyone in the study group has to strip down to their underwear.
Sherlock, "A Scandal in Belgravia": Mrs Hudson hides a camera phone down her blouse.
Stargate SG-1: Vala Mal Doran will do that to hide something she stole. Notably in episode 2 of season 9, with a gold medal from the Ancient Cavern of Glastonbury.
In Zoey 101, one of the female teachers was shown to be hiding a can of ravioli and a spoon in her bra.
Santana: Hello?! I taped it to my underboob! If Kurt taped it to his junk, we'd never hear the end of it! We'd be singing songs about it all week!
An episode of My Two Dads had the Judge taking a cell key from a cop and locking herself in with Joey, then ostensibly storing the key in her chest when the cop demands it back. She then handcuffs herself to Joey and has a picture taken to aid his protest against beach pollution (what got him jailed in the first place was dumping oil on a CEO's desk or something similar).
Discussed on Once Upon a Time: When Snow White is about to go negotiate with her wicked stepmother to save Prince Charming, she disarms as requested. Grumpy the Dwarf advises her to "keep the small knife between your tuffets" as a hold-out weapon in case Her Majesty was going to play dirty.
NCIS: Los Angeles: Kensi uses a bra holster in the Season 3 episode "Neighborhood Watch".
Arrow: In "Trust but Verify, Thea tucks the capsules of Vertigo into her cleavage. Not that there was anywhere else to put it in that dress.
An Israeli song called something like "Where are those girls", mentions women carrying a few hand-grenades and a small gun in their bras in case of sudden battle. "But of course, today's cleavages can barely hold what's already there..."
The video to Kesha's song "Blow" has her pulling out her bra at one point.
The end-of-game match sequence for Capcom's Breakshot has a cue ball that bounces off the table, hits a glass, and knocks a lemon that lands between a woman's breasts to reveal the match number.
This cover for a 1962 issue of Detective Magazine.
This trope gets mentioned in the 1948 Alan Jay Lerner/Kurt Weill musical Love Life in the song "Economics":
Now Edna used to slip her husbands Pay down her chest And just to keep it extra safe She never undressed! Now that's good economics, That's good economics, That's good economics But awful bad for love!
Older Than Radio: In Die Fledermaus (1874), Eisenstein has a ladies' watch that he charms pretty girls with. He is disguised as a Marquis at a dinner party, and his wife (unbeknownst to him) is disguised as a Hungarian countess. He tries to seduce her, and three guesses where she stows the watch. (It is intended to be worn like that, mind, as it's a highly steal-able item.)
Playfully subverted in Annie Get Your Gun. After Annie's younger sisters lock up her guns before her big showdown against Frank, each of them tries to tuck the keys down the front of their dresses for safekeeping. And each time, the keys fall right to the floor. Annie's little brother decides to keep the keys in his pocket instead.
In Final Fantasy X, this appears to be where Yuna and Lulu keep potions, judging by the animation when they use one. Hilarity ensues when you teach Yuna the Use skill. Apparently the girl keeps grenades in there.
In an otherwise short-and-forgettable flash game, Bush Royal Rampage, while being guarded by George W. Bush, Queen Elizabeth II has her tiara shot off, which only serves to anger her. She then pulls out a piece of plastic no bigger than a poker chip from her cleavage... which expands into an uzi!
In Silent Hill 2, Maria keeps the three keys to a triple-locked door tucked into her short skirt, in her boots, and in her cleavage, in that order. While she's opening the door, James attempts to sneak a peek to no avail.
The Guild Wars' female assassin underwear has a dagger between the breasts.
That's nothing compared to Magoichi, who is apparently capable of summoning pistols, hand grenades, a shotgun, a machine gun and a bazooka from her corset. Either that, or some sort of secret dimension. Though She actually keeps her pistols in a strap on her leg. All infinity of them.
In MadWorld, the three geisha you save in the Asian Town level appear during the final boss battle, pulling health-restoring items from their cleavage and tossing them off to you if you're running low. Oddly, the announcers make no comment on this.
Meryl Silverburgh of Metal Gear Solid fame stored a key card and Desert Eagle pistol inside her cleavage, as well as an untold number of magazines for said pistol.
In Wild ARMs 3, Maya Shroedinger has an attack called "Calamity Jane" where she shakes her skirt and a gatling gun falls out. Yikes.
In Resident Evil, Jill Valentine can carry more items than her allies, Chris (RE1) and Carlos (RE3), despite the fact that both of the guys are demonstrably stronger than she is. This is especially noticeable in 3, where Jill's wearing a tube top and miniskirt, while Carlos is wearing combat gear loaded with pockets.
In one of the cutscenes in Bayonetta, she hides a round in VSC.
Nurse-ninja Valentine of Skullgirls stores a number of objects between her quite sizable breasts (which is saying something, considering the rest of the game's cast), including throwing stars, syringes, and a thermometer.
Mad Moxxi in Borderlands 2 seemingly stores an unbelievable number of items in-between her not unremarkable breasts, which she will reach into when offering the player an item. These can range from submachine guns to pistols to even shields or relics. This may be excused, however, because of the game's use of small, digitizing "storage decks," one of which she could conceivably have tucked conveniently into the front of her shirt.
Ronin Galaxy: In the beginning of the second chapter, Leona manages to keep her sword hidden in the upper folds of her kimono, even past the gaze from possible onlookers such as Cecil.
Spoofed in this Ask Altair comic — the method makes no sense in the character's case.
A The Devil's Panties strip shows Jen and one of her friends getting ready for a night on the town. Club clothes for women often have no pockets and they were helpfully wearing corsets. Jen and a group of corseted women also used this trick during a Medieval Re-enactment weekend, storing assorted melee weapons. When the ladies are attacked by bandits thinking them unarmed, Hilarity Ensues.
Milo: What're you wearing? Jenny:(having shoved two comically large cans down her tank top) Oh, I got a nice, tight shirt on. It really shows off my cans... they're nice... and... cylindrical.
Genderbent in Prequel. Gharugg keeps things in his abs.
In Dubious Company, after capturing the pirates, Marty frisks Tiren. The Extended Disarming sequence leaves a mass of weapons greater than her, and he is creeped out by where she keeps her shirukens. Also noted on her profile page:
Through intense training, Tiren has learned to hide an innumerable amount of weapons on her person, regardless of what she happens to be wearing.
Shredded Moose did this with a word bubble's tail. It was allegedly so vile that even the most caustic critics were afraid of comment on it beyond pointing out that it's there, And That's Terrible.
Jamie's pet kitten gets lost there a few times. It's implied that the kitten was a soldier who died young in a previous life, now getting a hero's reward.
And Jamie's sister uses it for a hidden liquor stash, which she dares Hazel to get for herself when Hazel's nervous about going underwear shopping with her. The bottle contained water that time, it was a Magic Feather ploy so Hazel would stop freaking out about her boobs.
As Busty Girl Comics shows us, this compartment is good for other things aside from weapons, such as:
In Wapsi Square, Atsali collides with Castela and her smartphone falls between her embarrassingly ample breasts. Castela outright searches to find the phone (and the next page, while non-canon, reveals more loot).
Khanzarina Misha from Open Blue hides a handgun in her cleavage. Rumor has it that she keeps her saber in there too.
The spectacularly busty Winter Pierzina and her viral "Bra Purse" series spoofs this, although she admits that she really does this on a regular basis.
Survival of the Fittest v4 pre-game has a bizarre example, where a character puts around 6 to 8 jello shots down her bra. Needless to say, this is treated as Snark Bait among many handlers, to the point of borderline Memetic Mutation. In a previous game, Maxie Dasai - somewhat more realistically, stows a pistol in her shirt. This is lampshaded by the student she's fighting, who has to restrain himself from ranting at her about gun safety. Unfortunately, things took a turn for the more serious afterwards, as her opponent, Adam Reeves, tore her shirt and bra open to get to the gun, leading to him rapingMaxie.
While reviewing Interstella 5555 with other crew Paw Dugan, Nella and Elisa, Jew Wario is skeptical at the sight of the female lead tucking a card between her boobs. Lisa responds that it's just one of those special things about being a lady. To demonstrate, Nella pulls several tins of food out of her bra. Shocked, Jew Wario turns back to Elisa, who has produced three books and a pair of sandals from her cleavage.
Futurama: Corporate tycoon "Mom" hides the controlling device of the world's robots in her bra. At the end of the episode it's also shown that Professor Farnsworth keeps the controls of his giant albino shouting mutant gorillas in his pants.
Family Guy: Chris' substitute teacher hid everything in her boobs, including a whole class' worth of tests. She even had a machete in there. And then there's the time the raccoon that kept attacking Peter jumped out from between Lois' breasts after she undid her blouse. It was the third time the raccoon attacked Peter.
When the Monarch proposes to Dr. Girlfriend, they're about to have sex and she's completely naked. He's therefore understandably baffled when she pulls of list of concessions he needs to make out of nowhere, though his reference to how it's "undoubtedly moist" shows that the Monarch has his theories.
"I Know Why the Caged Bird Kills": Doctor Girlfriend pulls an aerosol can from her cleavage, while wearing her Queen Etheria costume to boot!
Sit Down, Shut Up: Miracle Grohe keeps a list of all the students who are on the starvation drive in her blouse.
Near the end of one Pepe Le Pew cartoon, Pepe is looking for Penelope, thinking she has maybe returned to the perfume shop. Penelope, who finds a blue Pepe to be extremely hot, comes in behind him, closes the door, and drops the key down the front of her coat. It's a Poetic Justice ending: Pepe had been chasing her throughout the cartoon because a spill of whitener had left her tail with a skunk-like streak. Towards the end, she fell in a rain barrel (removing the white on her tail and giving her a cold so she can't smell anymore) while he fell in the blue paint (covering up the BO that made her run away earlier). Now she's chasing him. Several Pepe Le Pew cartoons have these turnabout endings.
A use of not getting past the radar in KaBlam!: The Kablammy Awards episode ended by giving the award to the winning cartoon. Where's the envelope? In June's dress. But seeing as she's ten and well, doesn't have anything, they got away with it. But so did a lot of other things.
In Grandma Got Run Over by a Reindeer, Cousin Mel often hid things between her breasts like Austin Bucks phone number, Santa's letter, and some money she received from Bucks.
Cornfed's girlfriend Tamora from an episode of Duckman hid things like Cornfed's phone number and her note to him in her enormous breasts.
In the Goof Troop episode "The Ungoofables", Peg's great-grandmother hid a soda recipe in there.
Played with in some old Popeye cartoons: Olive pretends to hide things (mostly money) in her cleavage, but her hand descends all the way to her boots/shoes.
Young Justice: Madame Xanadu in "Denial" puts her money in her cleavage.
Stickin' Around's own Stacy Stickler is a rare young girl example of this, since she does this with a bottle opener to prevent Bradley from opening a bottle of Mr. Fizzy until after he helps her clean up her closet.
Luanne in King of the Hill stuffs dollars in her top to hide them from Bobby in the episode "Joust like a Woman".
A girl also did this in the Beavis and Butt-Head episode "Date Bait" after Butthead gives her some dollars.
DC Showcase: Catwoman features Selina retrieving her whip and a golden cat collar from inside her suit by way of her undoing her top. This is quite impressive considering just how tight we see the suit really is.
In the American Dad! episode "Max Jets" Roger's girlfriend Gina hid their marriage documents that wouldn't leave her any of his money after he died in her cleavage.
Betty Boop often retrieves items from the front of her dress, usually a compact mirror with makeup. Makes sense since her usual flapperdress doesn't have any pockets.
During the U.S. Senate investigation of the Iran-Contra Scandal, Sen. Howell Heflin (D-AL) accused Lt. Col. Oliver North's secretary Fawn Hall of smuggling papers out of the White House in her brassiere..
During their infamous performance at the Video Music Awards, Britney Spears, Christina Aguilera, and Madonna would stick their microphones down their cleavage when they were dancing. It wasn't that noticeable on Madonna, since she was wearing a black tuxedo, but on the other two (especially Britney), it was odd looking.◊
There have been bras designed with a pocket between the cups to hold money.
There have also been bras designed with a holster between the cups. There just aren't many good places for a woman to carry concealed, y'know.
Those frilly gowns with corsets worn by ladies of the pre-industrial age did not have any pockets. Where did the ladies keep love letters? In the Victoria's Secret Compartment!
Efforts to avert this trope in real life are one of the big reasons that premodern police forces kept a few "matrons" on staff — female police officers who wouldn't cause quite as much hilarity to ensue in a search. Even today, police and other law-enforcement departments, for legal and practical reasons, keep females on the rolls to handle anything beyond a basic on-the-spot frisk.
Quite a few girls who go to parties in an outfit designed without pockets will keep their phone in there. Lily Allen can be seen doing just this in the music video to one of her better singles.
Wedding dresses don't have any pockets, and neither will the bridesmaids; a few strategically placed tissues can be quite handy if anyone's a little tearful after the big moment.
In the 1950s, the "Miami Brassiere Brigade" stole hundreds of thousands of dollars of coins from phone boxes (it went to the company where they worked) by putting it in their bra. The things you learn from QI...
There is a knitting pattern for a bra with a pocket. While not in the cleavage, it claims to be able to hold condoms note which is actually a bad idea, since body heat can weaken the rubber in a condom, which is also why they don't recommend that men keep them in their wallets, change, and other small items.
Hurricane Katrina Rescues, an animal rescue programme, mentioned that just prior to Hurricane Katrina when people where evacuated to Texas from Louisiana via coaches people were smuggling their pets on board with them when there was a no pet policy. According to the Houston SPCA, one such animal smuggling lady managed to hide a cockatiel in her bra.
An anecdote from the filming of the original Doctor Who: apparently during the filming of the 1987 episode "Time and the Rani", the actress who played the female villain, Kate O'Mara, held up recording because her stick-on beauty spot had vanished from her face while on location, which meant they couldn't film her as it would have caused a continuity issue. It turned up an hour or so later... down her cleavage.
When S. Epatha Markerson won a Golden Globe in 2006 for her performance in Lackawanna Blues, she had her acceptance speech concealed in her cleavage. It created a really funny moment when she mentioned that it "moved" and she couldn't find it, and a really heartwarming speech when she had to wing it.
In a marching band with woodwind instruments, this is actually quite reasonable. Marching band uniforms don't always have pockets, and woodwind players always need a spare reed on hand.
Many female shoplifters will attempt this. You'd think women would keep stolen goods away from where most men are looking. Actually, they're cashing on it. If a dude tries to make a grab for the stolen "goods", the shoplifter can easily start screaming he's a pervert.
There's a news story, complete with footage, about a Midwestern woman being questioned by the police during a murder investigation who had a baby squirrel pop out of her cleavage several times during the interview. Each time, she just pushed it back down without comment.
It is, or was, common for women to keep their lipstick in their bras even when carrying a purse. The warmth softened it, making it easier to apply evenly.
Girls often tuck ipods into their cleavage when running around the track in gym class or at gyms so they can listen as they run.
For "smaller" girls, the side of the bra can be substituted for between the boobs, especially if they wear a size too small or a push up bra. This should be the side of the breast, NOT under the armpit. Generally used for phones or iPods. Be careful, this may cause an odd lump under the shirt.
Sports bras create an actual 'pocket' between the breasts since they're made in one straight piece of fabric instead of discrete cups. Beware stuff shoved in the top making its way down between the breasts and out under the elastic strap, especially if it's heavy or the bra's a little tight—the notch at the base of the breastbone can create a gap under some circumstances.
The WonderBra has been recommended to travelers as a form of money belt, putting extra cash into the insert pockets.
Larger-breasted women are especially lucky in this area in terms of how much stuff they can hold in this compartment without it being noticeable. With large breasts comes large difficulty finding shirts that actually fit properly, so assuming that she doesn't tailor it later or isn't excessively fat, the shirt will go over the bust and hang down. If a larger breasted woman is in this situation, she can put amazing amounts of stuff under the breast that can create quite a lump, but is quite invisible if she keeps her shirt on. This is sometimes called "infinite capacity".
Many women keep cash/credit cards tucked in the bra even if they do have pockets. A woman may not notice if someone picks her pocket in a crowd, but it's a sight more noticeable if someone tries to reach down her bra.
One company now sells a bra-mounted beverage pouch for women. They call it the Wine Rack. According to their press releases, it holds 25 fl. oz., and makes an A-cup into a DD.
Female operatives in World War II were specifically trained in the use of all possible hiding places on their persons, especially the ones most men would be reluctant to examine too closely. This was most assuredly among them. This aspect of training has most likely been retained.
Can lead to case of Fan Disservice if you're a cashier and a larger, older customer feels herself up in order to pull out a wad of cash...that's moist.