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 boy (and it's nearly always a boy) 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.

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

Literature

 * 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".
 * 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 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.
 * That last spoiler makes the entire example one hard subversion combined with in-universe Fridge Horror. It would serve as a Moral Event Horizon for Tywin on its own, if Tywin hadn't been established as a Complete Monster 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.
 * 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 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.

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 and Order has a man being procecuted for his son's murders after he seemed to have done this (which left said son rather twisted). The twist was that.
 * 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 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 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".
 * In the third season of Damages, Leonard Winstone's father reminds him of the time he "broke him in" by taking him to a prostitue 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.

Manga and Anime

 * Happens occasionally in Hentai manga/doujin.

Theater

 * This is a major plotline in the play and film Biloxi Blues, where the young army recruit protagonist receives "training" from a lady of the evening.

Webcomics

 * 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.

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.
 * 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.

Real Life

 * A man having his first sexual experience with a prostitute was quite common in the Western world up until the early 20th century. A gradual loosening of social taboos against mixed gender social activities, unchaperoned dating, and female premarital sex beginning in the 1920s exploded in the 1960s with a huge impact on the sex industry. Prostitution became far less lucrative as young single men also gained sexual access to women who might be future marriage partners, and paying for sex took on a greater social stigma as a sign that a man could not otherwise succeed in convincing a woman to have sex with him.
 * In Felicia Pearson's memoir, Grace After Midnight, she recounts her experience with a prostitute when she was 12. Apparently she had told her mentor that she was interested in women, so he hired her a female prostitute to "prove" that she wasn't a lesbian, she just wanted to be more like the local boys, thinking that the prostitute would scare her off the idea of being with women. It didn't work out like he planned; it just confirmed for her that she was.
 * Some care workers in the UK have discreetly arranged this for handicapped young people who would otherwise have problems forming normal sexual relationships. Unsurprisingly, it's a legal and ethical grey area.
 * In at least two states of Australia (Victoria and New South Wales), disabled persons have a legal right to sexual experiences with a sex worker, should they choose to exercise it.
 * Some people have said that disabled people specifically should be able to have access to a sex worker if they are otherwise against legalizing prostitution, assuming that disabled people would otherwise be unable to access sexual companionship.
 * Ray Bradbury lost his virginity this way. It is detailed in Sam Weller's biography on the subject of Ray Bradbury how when he was a teenager, he went with a friend to the red-light district and each paid a sex worker to provide them with this.
 * Legend has it that Thomas Aquinas's family was less than thrilled by his decision to become a Dominican friar, and at a point hired a prostitute to seduce him. It did not work, and he became one of the most widely known Saints of the Dominican Order.