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"I know about these girls. With their low marks and high hemlines!"
—Grace "97%" Makutsi, ~The No. 1 Ladies' Detective Agency~
Not the same as the Sassy Secretary (although there is some overlap, especially in hard-boiled detective stories), this is a PA/Secretary etc. who is rather a sexpot. You may add office-related Double Entendre as you wish (heh heh, "dictation").
- This ad for "6 Hour Power" energy drink, that starts with a long Male Gaze shot up the legs of a ridiculously gorgeous secretary. She then appears to give her boss a blowjob right in his office.
Anime & Manga
- In Durarara, Namie becomes Izaya's Sassy Secretary early on in the series. She's also damn fine.
- Kalifa, Iceberg's secretary in One Piece. It turns out she's actually part of a group of undercover assassins who've been working to get close to him and steal some important documents for five years, whereafter she is still sexy but not, in fact, a secretary.
- Uno of Magical Girl Lyrical Nanoha, who doubles as Mission Control for the Numbers and Jail's personal secretary. Heck, her information gathering-based Inherent Skill is even named "Flawless Secretary".
- An unnamed, short-skirted secretary in yellow gets a little screentime in two episodes of Serial Experiments Lain. In one episode, she gets close-up shots of her legs as she re-crosses them, and in another, we get a nice leg shot of her.
- Cecile Croomy from Code Geass counts as this and Hot Scientist.
- Villeta Nu is also this to Jeremiah Gottwald in the first season .
- Shizune from Naruto, as Tsunade's apprentice and, after Tsunade becomes Hokage, office assistant.
- During an action sequence in the movie Kite wherein the heroine falls down a skyscraper, the action briefly cuts into an office building in which a corporate suit is having sex with his secretary.
- Yuri from Tantei Gakuen Q. Also a Broken Bird Sympathetic Murderer.
- Holon from Real Drive. She counts as Robot Girl too.
- Brita from Darker Than Black. But it's only a cover, as she's actually an agent for Evening Primrose.
- Grace O'Connor, milquetoast stage manager and personal assistant from Macross Frontier. It's a cover.
- Jodie Crawford from Metal Wolf Chaos is a secretary, has a cute err... icon, and a rather pretty voice!
- And definitely Nanao Ise from Bleach. But all the females in that are just completely sexy.
- In Mahou Sensei Negima Chachamaru became this for Negi. She even daydreamed about some office romance.
- Miyuki Hyuuga from Detective Conan. Another "Broken Bird Sympathetic Murderer# case.
- Betty Brant, JJJ's secretary was Spider-Man's first love, although she was not terribly sexpot. She briefly got replaced by Gloria, who was sex on two long legs!
- In the movies, JJJ's secretary was played by Elizabeth Banks. So yeah.
- Iron Man features the lovely Pepper Potts, in the film, and the comic, naturally.
- Anne the receptionist in the Marvel Universe comic Damage Control.
- Victoria Hand, Norman Osborn's second in command during Dark Reign and Siege.
- Moneypenny from the James Bond movies (and all subsequent parodies of her). Note that in the original stories she was more dowdy.
- Actually, the original stories describe her with the adjective 'desirable' through the series. There turns out to be a lot behind the secretary who inspired Ian Fleming, and the actress who played her for two decades .
- The Moneypenny of the Dalton movies had the edge of being both blonde and wearing glasses.
- Played with in Casino Royale 1967 - David Niven as an out-of-retirement Bond enters his office and tells Moneypenny "You haven't changed a bit!". After a long smooch, she informs him that she's Moneypenny's daughter.
- The film Secretary. Maggie Gyllenhaal. The secretary only develops her sexy side in the course of the movie, and is really neurotic and closed-up outside her relationship with her boss.
- Lois Laurel (played by no less than Marilyn Monroe) in the classic screwball comedy Monkey Business. At one point her elderly male employer hands her some paperwork and says "Find someone to type this."
- Provides a moment of levity in the film Schindler's List: the viewer is treated to a montage of Schindler "testing" all the young female applicants to be his secretary. He flirts outrageously with each of them, then there's a shot of a grim middle-aged woman hammering away expertly at the test typewriter, with Schindler glumly slouched beside her.
- Gladys from The Pajama Game is really more cute than sexy, though she's treated that way by other characters.
- Ingeborg in Billy Wilder's One, Two, Three.
- Hot Fuzz. Supermarket manager and Smug Snake Simon Skinner has one, though her personality is more that of a gum-popping Sassy Secretary. She does have a part-time job as a table dancer though, and seems to spend more time sitting on the desk filing her nails and showing off her legs that doing any work.
- Ulla from The Producers.
- Amy Adams' character to Tom Hanks' in Charlie Wilson's War; congressman Charlie Wilson makes it a point to only employ beautiful women as his assistants.
"Congressman Wilson, he has an expression. He says, 'You can teach 'em to type, but you can't teach 'em to grow tits.'"
- Pepper Potts in Iron Man played by Gwyneth Paltrow.
- Marcia Gay Harden as Miss Cheevus in Spy Hard.
- Adrian Veidt's secretary in Watchmen is quite attractive, if prone to making exasperated facial expressions when his back is turned. And getting gruesomely shot in slow-mo.
- Miss Scott, General Turgidson's secretary and mistress in Dr. Strangelove. For bonus points, she's the only female character in the movie, and spends her entire screentime in a bikini.
- Dolly Parton's character in 9 to 5 is a subversion. She looks like this, and everyone else in the office thinks she's this, but she is horrified by the suggestion, and it leads to her joining the other two in their plot.
- Judy in the book Plainsong.
- Lady Jessica acts has her semi-husband's aide in Dune. She once with mild bitterness notes that this makes her a perfectly safe trusty of Atreides state secrets.
- John Nike from Jennifer Government muses at one point how, while hot secretaries are fun, they are ultimately impractical (since they ineivtably wind up demanding, and your books never get filed properly).
- Joan from Mad Men.
- The new British boss' male assistant (effectively a secretary) is considered absolutely heavenly by all of the younger American (female) secretaries. They particularly like his voice and accent, complete with the line about listening to him read the phone book.
- All of them. Probably even Miss "Queen of Perversions" Blankenship, in her day.
- This is actually a recurring plot point--as Joan mentions in Season 4, it's not uncommon for men to hook up with and/or marry their secretaries. Sterling does it early on, eventually marrying Don's secretary; Harry Crane gets Exiled to the Couch for it; and Don himself had a fling with Allison and ends up proposing to current secretary Megan by the end of Season 4.
- Sam from Richard Diamond Private Detective, originally played by Mary Tyler Moore, pulled this off while being unseen for the most part - all the viewers got was her voice and her legs...both of which proved replaceable.
- Jennifer Marlowe (Loni Anderson) in WKRP in Cincinnati. (Although she is very precise in identifying herself as a receptionist, not a secretary. And who didn't type or get coffee.)
- Stella's secretary in How I Met Your Mother. Notable in that she was played by a much revitalized Britney Spears following her divorce and subesequent breakdown.
- In Seinfeld, George tries to avoid getting a sexy secretary. He ends up with a nerdy, more efficient secretary instead, and has sex with her anyway, because she was so efficient it turned him on.
- Auf Wiedersehen Pet had Dagmar and Christa (played by Lysette Anthony)
- Commandant Klink of Hogan's Heroes had two, Hilda and then her Suspiciously Similar Substitute Helga.
- In the ITV 1 Work Com, Mumbai Calling, one of the call centre staff decides to hire a sexy secretary for his new boss. After said boss makes it clear he doesn't want one, the female assessor from London, who was dropped miles away at his suggestion (they thought she, Terri Johnson, was a he) and now looks very disheveled after an encounter with a fruit stall and donkey droppings, arrives. The first guy pulls a textbook Right in Front of Me, when he compliments her on her "dirty Carol Vorderman" look, but says the interviews are over.
- Oz. Warden Glynn gets a vivacious black woman as his PA, and for once no-one complains about having to wait to see him.
- Elaine Vassell from Ally McBeal
- Donnatella Moss from The West Wing wasn't just a secretary, but it was clearly included in her job description. As for her sexiness, sceptics are referred to the opening section of The Portland Trip and the red dress that has become infamous in the fandom.
- Private Helga Geerhart from Allo Allo.
- Young Mr. Grace (and his brother Old Mr. Grace) in Are You Being Served? had multiple sexy secretaries during the series. Just the sight of them often put quite a lot of stress on his weak heart, and in the sequel series Grace And Favour, a sexy secretary's bikini top popped off (off-screen, of course), and gave Young Mr. Grace a fatal heart attack.
- Stacy from Spin City played by Jennifer Esposito
- The secretary that gets kidnapped by Martians in Disney's Mars and Beyond.
- In the video for the Rammstein single "Pussy", the drummer Christoph Schneider plays a CEO who gets seduced by his secretary.
- Sandra McCoy as Justin Timberlake's "Sexretary" at the beginning of 'N Sync's "Pop" performance at the 2001 MTV Video Music Awards.
- Lene Alexandra in her "My Boobs Are Okay" video.
- Before joining Morning Musume Nakazawa Yuko was a secretary, she's also quite attractive.
- Ms. Buxley from Beetle Bailey, of course.
- Beetle is dating her now. Which begs the question, what happened to Bunny, Beetle's sweet girlfriend of before?
- Agatha Crumm's secretary, Winnifred.
- Stacy Keibler played a secretary-like character named Ms. Hancock on the team Standards and Practices for the majority of her time in WCW, and occasionally donned the sexretary gear in WWF/WWE as well.
- During his run as WCW Commissioner, Ernest "The Cat" Miller had a secretary named Ms. Jones.
- In WWE, when Mick Foley was the commissioner, Debra McMichael played this for a short time.
- Miss Tesmacher (no, not that one....)
- Samantha, the unseen/unheard assistant and scorer on I'm Sorry I Haven't a Clue.
- Hedy LaRue from How to Succeed In Business Without Really Trying. She can only type 12 WPM, but has other obvious qualifications.
- Ulla from The Producers. (Yes, she is definitely worth mentioning twice.)
- Rachel in Hotel Dusk: Room 215.
- Vice and Mature from The King of Fighters.
- In the goblin starting zone in World of Warcraft, the player had one on their home on Kezan.
- Mass Effect 2 has Yeoman Kelly Chambers, who is essentially Shepard's secretary. Flirt with her, and, regardless of gender, she flirts right back. She can even show Shepard her gratitude for being rescued.
- The Imperial Agent in Star Wars: The Old Republic contacts headquarters through Watcher Two, who the male Agent can flirt shamelessly with.
- Kotori Otonashi from The Idolmaster game/anime.
- Olga from Asura's Wrath Reincarnates into one of these in The Stinger of Episode 22 of the game, and is Deus's secretary.
- The webcomic Evil, Inc.. has had two; Lightning Lady and Desdemona. (Evil Atom hires them strictly on this basis.)
- Lavender of El Goonish Shive is a shapeshifting alien secretary who adopts a rather over-the-top appearance because she's a bit attracted to her boss.
- Ms. Sara Bellum, the Mayor's faceless yet very statuesque assistant from The Powerpuff Girls.
- The secretary from the Garfield: Babes and Bullets special.
- Iron Man: Armored Adventures gives us the lovely Tricia, secretary to
Howard StarkObadiah Stane.
- Swat Kats has Callie Briggs, the (much more competent) aid to the (foolish) Mayor Manx.
- An episode of the Sam and Max animated series pastiching spy films in general and James Bond in particular featured one. When Sam addresses her as "Honey bunny", Max suggests that he's being a tad familiar, but Sam points out that no, "Honeybunny" is her name, she's the temp the Geek hired; so Max flirts a little himself. Later on, she tries to flirt back, but she's disguised as the Geek at the time (it's probably best not to ask how or why, since the Geek is twelve years old and half Honeybunny's size), and Max is so wigged out that he opts to run for the hills even after she takes off the disguise.
- Rosemary on Hong Kong Phooey.
- Janine Melnitz on The Real Ghostbusters had some game but her appearance was changed because the creators felt her appearance and demeanor was too extreme in the first year. She was softened up and made rather generic.
- Leslie from Word Girl.
- Sandra Telfer of Broken Saints fame.
If you don't mind me asking... How the hell do you people manage to get any work done?