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Professional Sex Ed
A Man Is Not a Virgin, yet there's always a first time for everything. Some parents or mentors want to ensure their children's education is comprehensive, and some things are best left to professionals, so an older adult procures the services of a prostitute to give the child a practical demonstration of sexual intercourse. Might be performed by a Hooker with a Heart of Gold.

Subtrope of Sex as Rite-of-Passage, where a male virgin deliberately goes to a woman or girl (one he already knows or one sought out for the purpose) to "become a man".

Can be a feature of certain historical settings like The Wild West, or confined to certain cultures or social classes.

Examples

Fan Fiction
  • Relax is a followup to Welcome To The Brothel. Apparently, the protagonist has been taught well by the prostitute.
  • 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 mare, 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.

Film
  • 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.
  • This seems to be why Billy Bob Thornton's character takes his adult son with him to visit a prostitute in Monsters Ball.
  • 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 Malena has the young lead character experience this.
  • 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 wide 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.

Literature
  • 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.
  • 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".
  • 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 folowing 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 Orson Scott Card's Homecoming series, this is actually an accepted practice in 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.
  • A traditional among the nobility and upper classes in Kushiel's Legacy is to celebrate their sixteenth birthday and entering adult society by a visit to the Court of Night Blooming Flowers.
  • 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.
  • In the Kushiel's Legacy, this is standard for young nobles when they turn sixteen, and 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').
  • 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.
    Anxiety: What if he sleeps with her?! [The Price Is Right-like indicator pings]
    Angel: What if he's rolled in flour... [price goes up] whipped... [up again] and made to wear diapers! [astronomical amount]

Live-Action Television
  • 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. (Note that he looks to be about twelve when this is going on.)
    • Octavian is fifteen or sixteen, going by the relative ages of characters and historic actions that are occurring. (Actor Max Pirkis was in his late teens.) 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.'
  • 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....
  • 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.
  • On 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.

Manga and Anime
  • Happens occasionally in hentai manga/doujin.

Theater

Western Animation
  • 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.)
  • 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.

Of Course I'm Not A VirginVirginity TropesSex as Rite-of-Passage
Pity SexThe Oldest ProfessionRed Light District
Professionals Do It on DesksAdministrivia/No Real Life Examples, Please!Queer People Are Funny
Primal SceneSex TropesProfessionals Do It on Desks

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