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Professional Sex Ed (view source)

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{{trope}}
[[A Man Is Not a Virgin]], yet there's always [[Sex Asas Rite of -Of-Passage|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 boy [[Double Standard|(and it's nearly always a boy)]] a practical demonstration of sexual intercourse. Might be performed by a [[Hooker Withwith a Heart of Gold]].
 
Subtrope of [[Sex Asas Rite of -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.
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* [[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 Aa Gentleman]]'' only seems to "date" prostitutes, and his idea of bonding with his son is to invoke this trope.
* The main character of ''[[Sweet SweetbacksSweetback'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 ''[[Porkys|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 [[wikipedia:Roy L. Dennis|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
 
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* 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 (Literature)|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". {{spoiler|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 [[Defeating the Undefeatable|Undefeatable]] to a duel for insulting his family in public, a [[Hooker Withwith 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 [[Raised Asas the Opposite Gender|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 apparently [[Truth in Television]] for the author, [[James Joyce]].
* 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. {{spoiler|Eventually, it turns out that this isn't quite what happened.}}
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** ''[[Tales of the Five Hundred Kingdoms|The Fairy Godmother]]'': Prince Alexander says this is normal in his kingdom, and was done for him.
** ''[[Heralds of Valdemar|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 (Literature)|Discworld]] series:
** In ''[[Discworld (Literature)/Monstrous Regiment|Monstrous Regiment]]'', Jackrum brings his extremely young-looking troops {{spoiler|(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 ''[[Discworld (Literature)/Pyramids|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 [[KushielsKushiel'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 [[The Protagonist|Dinah.]]
 
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* 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.)
* The ''[[Firefly]]'' episode "Jaynestown" dances back and forth between playing this straight and subverting it. Inara, the show's [[Hooker Withwith 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 well have 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".
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== Webcomics ==
* In ''[[Fanboys (Webcomicwebcomic)|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.
 
== Western Animation ==
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