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- Used to good effect in Welcome To The Brothel. The protagonist is a virgin working as a mercenary during a civil war. His squadmates discover that he's never been with a woman, so they take him to a brothel. He learns about sex from a Hooker with a Heart of Gold. Whether it is ultimately for better or for worse is left up to the reader.
- Relax is a followup to Welcome To The Brothel. Apparently, the protagonist has been taught well by the prostitute.
- The Western movie Lightning Jack has a sequence, played for laughs, where Jack takes his teenaged offsider to a brothel and arranges for him to get hands-on sex ed.
- The protagonist's father in An Officer and a Gentleman only seems to "date" prostitutes, and his idea of bonding with his son is to invoke this trope.
- The main character of Sweet Sweetback's Baadasssss Song works as a towel boy in a brothel and loses his virginity this way. The movie depicts this scene by casting Melvin van Peebles's 13-year-old son, Mario, as the young Sweetback and having him come close to undergoing this trope in Real Life.
- Played with in Porky's: the boys go to Porky's in order to do this for themselves but are thrown out of the place. Later as a prank the other guys make Peewee think that he's going to have sex but then the hooker "dies" and Peewee freaks out.
- In Mask, the protagonist Rocky Dennis suffers from a genetic defect that causes his face to be disfigured. He's concerned that he'll never get a girlfriend because no one will look past his face. His mother then goes out to hire a prostitute to make him feel better. It backfires since Rocky not only doesn't have sex with her, they just talk, but also took the gesture as a sign his mother thought no one would want to be with him unless they were being paid.
- The original European version of Malèna has the young lead character experience this when his father sends him to a local brothel to "become a man". It's understandably presented as somewhat of a frightening ordeal, considering the boy is only about twelve when this happens. He also fantasizes about Malena herself replacing the prostitute.
- The Sessions tells the real life story of Mark O'Brien (played by John Hawkes), a poet paralyzed from the neck down due to polio, who hired a sex therapist (Helen Hunt) to lose his virginity.
- In Fanboys, one of the nerds picks up an escort in Vegas who explains to him that the girl in the group has a crush on him.
- Subverted and then toyed with in The Cherokee Kid. When offered the chance after saving a rather hospitable prostitute's life, she offers herself to the titular main character... Only to be turned down for a share of the turkey which was also killed in the scuffle with the bad guy. Later on he can't aim a gun, definitely can't do quick-draw, he can't even ride a horse. This being a cowboy flick, mind. When it comes out he's never made love, one of the women in the troop of outlaws decides to "make a man" out of him; while she's not ACTUALLY a prostitute (at least not said to be one) she fulfills every other aspect of the trope, especially since afterwards he can shoot straight and ride well.
- In The Curious Case of Benjamin Button, the captain of the boat Benjamin gets a job for hires a prostitute for him after he learns he's never had sex. This trope wasn't the captain's intent, as he thought Benjamin was an old man, but as he's really in his early teens, the end result is the same.
- The King's Speech. When his speech therapist asks Prince Albert if he and his elder brother chased the same girls, he confesses they shared the favours of a Parisian girl, implied to be a prostitute in an invocation of this trope. Not at the same time, he adds.
- The Last Prostitute (1991) has two teenagers (one played by Wil Wheaton) travelling halfway across the country to find a hooker who's been recommended by their uncle for this trope, only she's gotten out of the business and so isn't interested. She works on a farm now, and the teenagers have to hang around as stableboys as they told their parents they were going away on camp. Cue Coming-of-Age Story, but no Sex Ed.
- The entire plot of the '80s Teen Movie Private Lessons is this.
- Clint Eastwood produced, directed and starred in Honkytonk Man, a tale set during The Great Depression of a country singer with TB whose life's ambition is to sing on The Grand Ole Opry (already a decade old at the time in which the film takes place). Clint's character, Red Stovall, is accompanied in his travels by his young nephew Whit, for whom Red arranges the rite of passage, with of course a Hooker with a Heart of Gold. The fact that Whit was played by Kyle Eastwood, Clint's real-life son, can definitely bring on Unfortunate Implications if not Squick for some viewers.
- In Catcher In The Rye Holden arranges for a prostitute to come to his hotel room, and thinks that, since he never had sex before, it would be good to "have some experience." However, the prostitute, Sunny, is so businesslike about the whole thing that he decides not to go through with it.
- One of the characters in The Manticore by Robertson Davies has this arranged for him by his father.
- This is occasionally the use for the Betan Licensed Practical Sexuality Therapists in the Vorkosigan Saga - Kareen Koudelka had her first time with a hermaphrodite LPST. They're also a government regulated Band of Brothels.
- Apparently, Beowulfans in the Honor Harrington series believe this for both genders, to the point where Allison Harrington wanted to get her daughter a night with a male courtesan for her Academy graduation. Mom did not know until much later that it was more than self-image issues that made Honor a Celibate Hero for so long. She was pissed when she found out. It also didn't help that Honor was nearly raped by another cadet, who didn't anticipate Honor being a master of coup de vitesse. This incident not only affects Honor on a personal level, but also affects her career, since her would-be rapist and his father do their best to ruin her career before it even starts, despite the fact that she never reports the assault.
- In Looking for Alaska, the characters hire a male prostitute (disguised as a teenage sexuality expert) to put on an "assembly" for their class, declaring it the "ultimate prank". Which was done in tribute to Alaska, who planned the prank but didn't live to see it executed.
- Happens to young Alexander in the Arcia Chronicles: after the hunchback ugly duckling challenges the Undefeatable to a duel for insulting his family in public, a Hooker with a Heart of Gold makes a bet that she will make him a man if he survives. Obviously, he does and she keeps her end of the bet.
- In the Tamir Triad by Lynn Flewelling, the main character's elder cousin hires the protagonist a prostitute for this reason. Unbeknownst to him, his cousin is actually a girl (magic is involved) and also not interested in women. The protagonist and the prostitute end up just faking it (as the cousin is listening in from the next room).
- In A Portrait of the Artist as a Young Man, Stephen Dedalus is practically forced to explore sex this way because he lives in very Catholic Dublin; it causes no end of Catholic guilt for him later on. It was largely Truth in Television for the author, James Joyce, although he turned up the guilt for the book because of Rule of Drama.
- In Tyrion Lannister's backstory in A Song of Ice and Fire, he loses his virginity to a crofter's daughter who he ends up marrying shortly after, only for his brother Jaime to reveal to him that she was a whore whom Jaime had paid to give him his first experience in an elaborately-crafted setup. Eventually, it turns out that this isn't quite what happened. That last spoiler makes the example a subversion combined with in-universe Fridge Horror. It would serve as a Moral Event Horizon for Tywin on its own, if Tywin hadn't many times before then. Also turns out to be Tyrion's Berserk Button.
- Mercedes Lackey has used this at least twice:
- The Fairy Godmother: Prince Alexander says this is normal in his kingdom, and was done for him.
- The lady in question takes the "education" part seriously, and gives him some very useful "training" for when it's his turn to initiate someone.
- Exile's Valor: Alberich spies on a conversation at a high-class bordello that is the usual place for wealthy gentlemen to bring their sons for a "first time".
- The Fairy Godmother: Prince Alexander says this is normal in his kingdom, and was done for him.
- Discworld series:
- In Monstrous Regiment, Jackrum brings his extremely young-looking troops (actually, female) to a brothel, and uses education as an excuse. (Really, they're just there to steal the women's clothing for disguises.)
- In Pyramids, the first quarter of which explains much about the workings of the Assassins' Guild School in Ankh-Morpork, there is a specific reference to the very thorough personal and social education of the older boys at the (then all-male) School. As sons of the best families in the land, the School sees to it that they can hold their own in all companies and answer all challenges. Reference is made to older boys coming back to the School very late, even the following morning, yawning, tired and unable to focus on the day's lessons - but in a way which is accepted and tolerated by the teachers and carrying none of the usual sanctions. It is hinted that this is connected with "seamstresses".
- In the Homecoming Saga, this is actually an accepted practice in the city state of Basilica, referred to as hiring an "Auntie" for a young man's first time.
- In The Dark Tower series, this was how the main character Roland lost his virginity.
- Kushiel's Legacy both subverts this trope and plays it straight. For a bit of context before the examples, you should know that prostitution is considered an honored and sacred profession to the d'Angeline people, women cannot become pregnant unless they intend to be, and bisexuality is the norm.
- When Phèdre and Alcuin are training to be courtesans, Cecilie Laveau-Perrin is hired to be their tutor. But subverted, as—to Phèdre's surprise—Cecilie's teaching is confined to the classroom and books. She teaches them what to do, to be sure, but she doesn't show them.
- Played straight a few books later. A traditional among the nobility and upper classes is to celebrate their sixteenth birthday and entering adult society by a visit to the Court of Night Blooming Flowers (an elite Band of Brothels). Princess Sidonie even has Amarante, the daughter of a priestess of Namaah (aka basically-the-goddess-of-sex-among-other-things) as one of her ladies in waiting... and to teach her "the arts of the bedchamber."
- In The Red Tent, Prince Shalem mentions having been taken to the high priestess to lose his virginity upon reaching puberty. She kept the room dark, so he couldn't actually see her, the idea being that he was sleeping with whatever goddess she served or represented. He fondly remembered it as "like a dream within a dream," although he says it does not compare to his honeymoon with Dinah.
- Earth's Children and its pre-historic cultures are all over this, and for both genders too! During Summer Meetings, women can volunteer to be "donii-women" and help out boys in need of a first time. It's a religious office ("Doni" is the Zelandonii word for "Earth Mother"), and the fact that such women typically end the summer pregnant is considered a mark of Her favor. Plus, when it's a girl's turn, a man is chosen (sometimes from her clan, but preferably someone from a bit farther off) to give her a magical experience. This is also a religious task, and both parties are supposed to avoid emotional entanglements.
- Goes horribly, horribly wrong in the Spenser novel Crimson Joy, in which a Serial Killer of prostitutes turns out to be repeatedly acting out his rage at a prostitute who his abusive father hired to "make a man of him" and who humiliated him when he couldn't perform.
- In The Lords of Satyr, young Nicholas's father takes him to a brothel to get the deed done, though he has already had the first few lessons with a flirtatious housemaid. (This plus his father's own example makes him a believer in the Madonna–Whore Complex, though he eventually gets over it).
- In the novel Scarlett, Rhett takes the young man who has been peeping into women's bedrooms to the local brothel, realizing that his behavior is not out of perversion, but simply a genuine curiosity about the female body.
- In Fried Green Tomatoes at the Whistle Stop Cafe, Idgie sends Ruth's son to the Village Bicycle (who would be a quintessential Hooker with a Heart of Gold if she actually were a prostitute) to take his virginity after he admits that he's downright terrified of having sex (aside from the normal angst of a teenage boy, he has only one arm and fears either hurting a girl or having her laugh at him).
- In Anne McCaffrey's Damia, Afra loses his virginity to a "companion". It's implied that "first timers" like Afra are common visitors to brothels in that universe.
- In one of Mickey Spillane's novels, the protagonist mentions this trope usually ends in the boy being too nervous to perform and tipping the hooker extra so she'll tell his father otherwise.
- Common enough in Genome, although most use virtual partners. Only the wealthy can afford to hire professionals for their kids.
- The 80s TV series Bret Maverick mentioned this in a two-part episode called "Faith Hope and Charity": the townsfolk are setting up for massive retaliatory scam in the saloon's upstairs rooms, and the bartender waxes nostalgic over a certain bed, recalling that his father had hired a prostitute to show him how it's done. The wave of nostalgia renders the bartender useless for the task at hand as the scene is Played for Laughs.
- An episode of Law & Order has a man being prosecuted for his son's murders after he seemed to have done this (which left said son rather twisted). The twist was that it was his grandma who corrupted him and the father was powerless to stop his mother.
- Mentioned in Frasier; according to Bulldog, his first sexual experience was with a prostitute that his dad had hired for him. (He claims, "All I wanted was a bike.")
- On the HBO series Rome, Atia hires war-hero Titus Pullo to make her son Octavian (the future Emperor Augustus) into a man. Naturally, one of Pullo's efforts is to take young Octavian to a Roman whorehouse. Octavian is fifteen or sixteen when this is going on, going by the relative ages of characters and historic actions that are occurring. By Roman standards, he was about to legally become a man, and Atia wanted him to learn all the appropriate Roman male behaviors, including 'penetrating someone.' Octavian himself, by the way, is rather bored by the whole thing and just wants to get it over with to stop Atia's nagging.
- The Firefly episode "Jaynestown" dances back and forth between playing this straight and subverting it. Inara, the show's Hooker with a Heart of Gold, is hired by a rich snob to "make his son a man". The son has much more confidence afterwards, but this may have had as much to do with Inara's pep-talks before and after as with the actual sex.
- Happened at least once in Key West, involving Jennifer Tilly's character and a teen so nervous that when asked if he brought protection he tells her he's already wearing it. He was fully clothed at the time.
- The series Weeds has an uncle take his 12-year old nephew to a massage parlor so he can get his first "happy ending".
- In the third season of Damages, Leonard Winstone's father reminds him of the time he "broke him in" by taking him to a prostitute for his first time.
- Christian treats Matt to this in Nip/Tuck. It doesn't work so well...
- Attempted in A Place To Call Home. In a flashback scene, we see George's father hired a prostitute for him and got as far as introducing him to her. We don't see exactly what happened, but it appears George refused to go through with it.
- The 70s series James At 15 has James postpone a date with his girlfriend on his 16th birthday (in which he was expecting to go all the way) because his rich uncle has promised to give him "what every 16 year boy wants." James is expecting a car. He is very disappointed when the present turns out to be a hooker.
- In Veronica Mars, a boy meets a cute girl at a convention and has his first sexual experience with her. Later, it turns out she was hired by his friends. Subverted however in that it's revealed that they genuinely fell in love that night and just spent the entire time talking.
- Game of Thrones:
- Tyrion sends Joffrey two prostitutes as a nameday present, in the hopes that getting laid might calm him down a bit. It backfires spectacularly because Joffrey is only interested in making them torture each other.
- Tyrion also provides some prostitutes for Podrick upon learning that he was a virgin, giving some of Littlefinger's girls a rather large bag of gold to introduce him. A while later, Podrick comes back to Tyrion to return the bag—not because he had refused to do it, or because he had stiffed the girls, but because Pod turned out to be so, erm, good that they refused payment.
- The Janitor from Scrubs says to Doug while drawing a mural of a whore house on his leg cast that on his 12th birthday, his father took him to the whore house. Given the Janitor's tendencies for Multiple-Choice Past, it's uncertain if he was telling the truth, but Dr. Kelso confirms the place existed.
- Drop the Dead Donkey. Pointy-Haired Boss Gus Hedges starts having erotic dreams about office hottie Joy, so he asks Handsome Lech Dave for help, promising to be "financially grateful". Realising his boss is a stuck-up virgin Dave sets him up with a professional sex counselor and the problem is resolved (actually Gus passes out from anxiety and the hooker lies to him about his night of passion — what else would you pay a hooker for?). Dave turns up for the promised pay rise the next day, only Gus has fallen asleep and is having a Homoerotic Dream about Dave, who is immediately thrown out of the office the moment Gus wakes up.
- Herman's Head. Herman's boss gets divorced, so he asks Herman to set him up on a date. Herman fobs the task off on his friend Jay, who sets Mr Bracken up with an escort, paying for it using Herman's credit card. The hooker goes along with it, but charges extra for 'roleplay'. Herman then has a nightmare about how much this will cost him.
- In the Chilean Soap Opera Machos, the pretty much all-male Mercader family used to have a sort-of "tradition" where the sons would lose their virginities with local prostitutes. This deal ended when one of the current patriarch's boys, the fifth son Adán , was so traumatised by the idea that developed a severe case of erectile disfunction; years after this, the poor is still a virgin and that completely fucks up with his self-esteem.
- General Hospital: Lucky visits the local Hooker with a Heart of Gold because his girlfriend is recovering from a rape and he doesn't want to burden her with his sexual desires.
- A milder version on Married... with Children, when Al takes Bud to the local nudie bar once he's of age.
- In an episode of Hotel!, a father firmly believes that his son needs this trope to become a man. Privately, his son confesses to a hotel employee that he isn't a virgin but doesn't want to tell the girl's name to his father out of respect for her. His father himself frequents prostitutes and asks one to help him out in this respect. However, his son runs out on the "date". The hooker then suggests someone more his age and sets up a "blind date". However, instead of the girl, his son ends up picking up another woman, who looks like a professional. Except she turns out to be an undercover cop, who busts him for solicitation. Whoops. In the end, the father finally accepts that his son is a man.
- In the New Girl episode "Virgins", Nick reveals that his father once hired a pair of prostitutes to for him and Winston when they were teenagers. Winston went through with it (and refused to believe they were "professionals" when he heard the story again), but Nick backed out.
- In the Family Guy episode "Fore Father", Chris takes up Quagmire as a father figure, and takes him to a strip club to help him become a man. Knowing Quagmire, this is nothing out of the blue.
- On The Cleveland Show, Junior hears Cleveland making fun of him for making an abstinence pledge and, on Ernie's advice, goes to the local whorehouse. Cleveland and Lester show up to stop him from going through with it. (What happens with Ernie isn't clear, but by the end he and a prostitute elope together.)
- King of the Hill: Attempted by Cotton Hill, who in a flashback took a teenaged Hank and his friends to the then-seedy Hotel Arlen to buy them hookers. Hank of course runs out screaming. In the same episode, he attempted to do the same with Bobby, not realizing its not "that" kind of hotel anymore.