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Given that AManIsNotAVirgin, a leading man who has no sexual experience will be mortally embarrassed about the fact and feel the need to get de-flowered as soon as possible. The plot generally follows his attempts to meet Girls and get them into bed so he can win his place among his fellow Men. This is almost always a comedy plot (usually a comedy film), so his attempts are inept or nerdish and HilarityEnsues.

Conventionally the hero is successful, thus proving his masculinity and reassuring the insecure male virgins in the audience that they, too, will someday be Men. AnAesop about love being more important than sex will then be shoehorned in, and the hero will settle down with a nice girl -- quite possibly the UnluckyChildhoodFriend he completely ignored in his quest to 'get some.' Whether this happy ending satisfies the MoralGuardians varies; the wholesome 10% may shed some sanctity on the rest, but the main draw is the other 90% of the work -- the adventures of a shallow individual preoccupied with proving his (or her) worth through casual sex.

If the movie was made after 2000 then there will invariably be an UnratedEdition DVD promising even more titillating moments.

This trope could have originated from such [[TruthInTelevision warped standards in the real world]], or contributed to those standards; probably, both.

Often a subtrope of the ComingOfAgeStory. Contrast with the CelibateHero theory, which says, "Real men can resist sex." Compare SexIsCool. Often found in the SexComedy. A subtrope of this trope is ProfessionalSexEd.

----
!!Examples:

[[foldercontrol]]

[[folder:Anime and Manga]]
* The TransformationSequence of ''{{Pretear}}'' uses this trope as symbolism.
* In ''Anime/TurnAGundam'', the protagonist and other children would celebrate a coming-of-age ceremony as per tradition: among other things, they would go to the top of a mountain, strip naked, and put leeches onto each others' backs to create marks. And do whatever else they want. Too bad an untimely attack ruined the ceremony, or it would've been...very...interesting.
* The universe anime and manga ''{{Manga/Loveless}}'' has a unique aspect in that all virgins have cat ears and a tail until they first have sexual intercourse, and this is utilized in various ways to show a character's personal life. It's also [[SubvertedTrope subverted]] and questioned, especially with Soubi [[spoiler:who loses his ears as a result of sexual abuse by his teacher in a traumatic experience]].
** What makes it more twisted is that [[spoiler: Soubi was raped by Ritsu because Ritsu resented Soubi's mother for marrying someone else]].
* In the ''Manga/KodomoNoOmocha'' manga, Sana (thirteen at the time) wants to hurry up and "become an adult" because she imagines that [[spoiler: if they're adults, she and Akito won't have to be separated. They get in bed and partially undress, but Sana proves to be too ticklish and nothing happens because the mood is ruined.]] [[SubvertedTrope Subverted]] (arguably even [[DiscreditedTrope discredited]]) because it's clear that [[spoiler: Sana's becoming extremely irrational / mentally unstable]] at this point, and [[AuthorAvatar Sana's mother]] explicitly refutes this trope when they talk about it afterward.
* ''GunXSword'' appears to play this trope straight at one point, with [[EvilIsSexy Fasalina]] promising to turn the newest member of the Original Seven into a man through sex. However, this is later [[SubvertedTrope subverted]], as the narrator explicitly states that Van (a virgin) is a man, while [[spoiler: Michael]], despite his initiation into adult sexuality, is just a boy.
* [[SubvertedTrope Subverted]] in Jeanne Da'ck's works (being hentai) where DeliberateValuesDissonance is PlayedForLaughs in that the sex is a gauntlet to [[RiteOfPassage become an adult and choose a lover upon completion.]] A [[AlwaysMale candidate]] is left alone in a well-stocked house (namely a PornStash) with a [[BigBeautifulWoman local woman]] for a week to tempt him to [[ADateWithRosiePalms just jerk off,]] which if he does [[DisproportionateRetribution would auto-DQ him and wait]] [[FourIsDeath four more years as a virgin before retaking the test]] with [[InnocentCohabitation sharing a bed,]] [[FetishFuel an undersized mini-skirt on Day 2, a bikini on Day 3 and]] [[FullFrontalAssault just being fully naked together on Day 4]] until midnight of the fifth day where he not only finally ''can'' have sex, but has to ''stay'' inside her for entire day ([[UrineTrouble including pee breaks]]) with Viagra-like medicine being allowed with a surprise sixth day where the candidate has to have sex with his own [[IncestIsRelative MOTHER and cum 15 times in her before midnight.]] Upon completion, [[EarnYourHappyEnding the candidate gets whatever woman of his choosing to live happily ever after with.]]
** The second time this culture is shown [[UpToEleven ups the ante with TWO local women,]] skips straight to naked time on the ''second'' day, [[BrainBleach has to watch his own mother have sex with a chief as a supposed learning aid]] for the fourth day, perpetual BJ on the fifth with the women allowed to tag out ([[DepartmentOfRedundancyDepartment yes, including pee breaks again]]) and all day sex to wrap up the sixth day.
* All over the place in ''RevolutionaryGirlUtena'', as the difficulty and implications of growing up are one of its main themes. It's best exemplified in Akio, who represents the corruption of the adult world, who by the end of the series is basically an in-universe MemeticSexGod, and who repeatedly tempts the duelists by giving them a vision of 'something eternal' by taking them a drive in his car in sequences heavily suggestive that he's having sex with them. It's also possibly the reason behind the incestuous themes, exploring the tension between characters wanting to return to their carefree childhoods with their siblings but increasingly unable to access that world except through 'adult' means.
[[/folder]]

[[folder:Comic Books]]
* In ''Comicbook/SexCriminals'', when Suzie sleeps with her high school boyfriend Craig, she thinks it will be this. Turns out she doesn't feel any different afterwards.
[[/folder]]

[[folder:Film]]
* ''{{Porkys}}'', promoted as "The Raunchiest Movie About Growing Up Ever Made", features a 17-year-old hero. The sequel advances into MyGirlIsNotASlut territory.
* ''RevengeOfTheNerds'': No matter how many times the Nerds outsmart the Jocks, they haven't really beaten the Jocks till the chief Nerd seduces the chief Jock's girl. (Yes, I know, there was the big speech about Nerd pride while the ScaryBlackMan types intimidated the Jocks, but which part did we all really cheer at?) Of course she's a cheerleader, too; see AllGuysWantCheerleaders.
* ''Film/TheFortyYearOldVirgin'': Much of the humor in the film is due to the fact that the hero lives up to the title. He collects toys, underlining the pre-manhood status of male virgins. Ironically, despite his 'man-child' status, in many ways his non-virgin male friends were far more infantile and immature about sex than he was.
** It should also be noted that the hero reached his spiritual manhood long before he lost his virginity, since he waited to have sex until the honeymoon.
** Taken to another level in TheMockbuster TheAsylum film, ''The 18-Year-Old Virgin''. The titular virgin is a female HollywoodNerd who wants to lose it to her crush at a party. The guy is open to the idea, but doesn't want to have sex with a virgin, so she has to find ''someone else'' to take her virginity before she can hook up with her dream guy. HilarityEnsues.
* The entire plot of the film ''AmericanPie'', which in turn owes more than a passing debt to the similarly-structured 1980s comedy ''Hot Moves''.
** And even more so in ''Film/AmericanPie: The Naked Mile'', where ironically this trope was shoehorned as the secondary plot (because watching nude people was [[ExactlyWhatItSaysOnTheTin the one true point of that movie]]).
* In the 80s AffectionateParody of westerns, ''Film/RustlersRhapsody'', the hero is confronted with the fact that one of the requirements to being an official, sanctioned hero is that he has to be a "confident heterosexual". He thought it was ''just'' heterosexual.
* Played for drama in 2002's ''RogerDodger'', with the interesting approach of treating it as a FilmNoir object.
* RareFemaleExample in ''Film/FourRooms'', where a girl remarks on how she is "now a woman" after having sex with the main character.
* Another female example would be Winona Ryder's character Charlotte in ''Film/{{Mermaids}}''. This is somewhat of an inversion, however, in that Ryder's (Jewish) character embraces strict Catholicism, and even hopes to become a nun, precisely to ''avoid'' having to deal with her newly-awakened sexual urges. [[spoiler:She ends up doing it in the end, however.]]
* A harrowing example in ''Film/LeavingLasVegas''. A group of frat boys "buys" Sera to make a man of him. When she rejects his request, [[spoiler: they gang-rape her]].
* ''SexDrive'' is about a teenaged virgin who goes on a cross-country drive to meet up/have sex with a hot girl he met on the internet.
* [[{{Deconstruction}} Played horribly straight]] in ''LAConfidential'' where three teenagers kidnap a girl and rape her in order to 'become a man'. She is then left tied up in an apartment for days and only rescued because the kids were framed for another crime.
** Much worse in the book: after raping her, they drove around and "sold her out" to all their friends.
* A more serious-minded example: ''Summer of '42''.
* In the movie ''MilkMoney'', three preteen boys go to great lengths (breaking open piggy banks, having yard sales) in order to come up with the $100 (in change) needed to hire a hooker and achieve manhood. Hilarity ensues when they get to the city with the money, only to start asking random women to remove their clothing because they can't "tell a prostitute from everybody else." After successfully hiring one (who only gives them a brief topless show for their money), they pass out cigarettes, announcing that they have had sex and are now men. Men without matches, as it were, so they simply enjoy the unlit cigarettes hanging there.
** One of the boys chooses to cover his eyes when the prostitute removes her top, proclaiming that he "wants to be a gentleman." This is fortuitous, as it removes the squick factor of the prostitute's likely disposition at the end of the movie as [[spoiler: his future stepmother.]]
* One of the subplots of ''TheBoatThatRocked'' is the attempts the crew to let Tom Sturridge's character lose his virginity.
* Most of the plot of ''The Last American Virgin''.
* ''DirtyDancing'': Baby.
* Boner (pronounced "Bonner") in ''Film/ShriekIfYouKnowWhatIDidLastFridayTheThirteenth''. He spends the entire movie trying to get some. At one point, he spontaneously declares that the protagonists should [[AmericanPie make a pact to lose their virginity before graduating]]. Everyone turns him down simultaneously (but [[TheDitz Slab O'Beef]] agrees). At lunch (oysters, natch), he laments that roofies aren't getting him laid when he takes them (Slab opines that he's not taking enough). Even when it looks like he's getting some at the climax, it's all [[InnocentInnuendo sight gags]] to illustrate [[ActionGirl Martina Martinez's]] [[Film/{{Scream 1996}} rules of a parody situation]]. A HospitalHottie jumps him for his BiggusDickus as he's being loaded into an ambulance. The WhereAreTheyNowEpilogue reveals that she's a post-op transsexual; Boner doesn't care.
* This is pretty much the plot of every MichaelCera film. ''{{Superbad}}'', ''NickAndNorahsInfinitePlaylist'', ''YouthInRevolt'', plus he also loses his virginity in ''{{Juno}}''.
* ''Film/TheVirginityHit'' is the story of Matt, whose friends try to get him laid. [[HilarityEnsues And make a movie out of it.]] On a side note: the main character is played by Matt Bennett. Yes, [[{{Victorious}} that Matt Bennet]].
* In ''OneFlewOverTheCuckoosNest'', although he has to be persuaded by others into doing it, [[spoiler: having sex is what gives Billy Bibbit the confidence to stand up to Nurse Ratched, and gets rid of his stutter into the bargain. Candy must be some lover.]]
** Though after this triumph, Nurse Ratched [[spoiler: [[DontTellMama threatened to tell his mother]]. Billy promptly [[{{Deconstruction}} started stuttering again]], locked himself into a room, and [[DrivenToSuicide killed himself]]]].
* RareFemaleExample: In ''Film/LittleDarlings'', two teenage girls at a summer camp compete to be the first one to lose their virginity.
* ''The Cheerleaders'' is another RareFemaleExample even as soft-core porn as Jeannie isn't even considered HollywoodHomely by the cast, just either [[OvershadowedByAwesome obscured by her fellow outgoing cheerleaders hogging all the guys]] and/or hit with [[FinaglesLaw hit with hilariously Epic Fails like a casanova's waterbed bursting open enough to wash her out the door,]] plus her boyfriend's a [[NoAccountingForTaste a bland nebbish that sees her as a Genki Girl in the bad way.]] It finally takes [[DatingCatwoman a guy from the opposing team]] [[ButtMonkey that's also in the same situation since he missed out on the orgy that wiped out both teams]] to finally get laid in the locker room. Ironically, the star actress was actually as casual about being naked as Creator/HelenMirren compared to the [[IronyAsSheIsCast outgoing cheerleaders in the cast.]]
** Speaking of porn, a couple of the (non-Debbie) cheerleaders in ''DebbieDoesDallas'' invoked this trope, in the shower, in order to carry on their money-raising scheme. Unfortunately, one of the actresses had a c-section scar, which undermined the scene's authenticity!
* ''Film/SixteenCandles'': Freshman Ted spends most of the film trying to get laid. He starts with a puppy-dog crush on Sam, a sophomore, who wants nothing to do with him. When she finally reveals why she's been rejecting him (she herself has a crush on a senior, Jake), he gives up his dream in order to hook the two of them up. By doing so, he ends up rewarded by having sex with Jake's drunk girlfriend, Caroline.
* The central character in SexComedy ''Film/PrettyMaidsAllInARow'' is a frustrated high school senior who sports erections all the time and can't believe he's never so much as touched a breast. The guidance counselor steers him towards a female teacher to be his MrsRobinson.
[[/folder]]

[[folder:Literature]]
* ''Franchise/TheDarkTower'': Roland goes downtown and gets a prostitute immediately after becoming a 14-year old gunslinger. He does it for no other reason than because he could.
** Although there's a [[SubvertedTrope subversion]] in ''Wizard & Glass'', with a scene immediately after this where Roland's father busts into the room and lets him know he's still got a fair way to go before he's truly grown up.
* For another Stephen King example, in ''{{IT}},'' six [[{{Squick}} eleven-year-old]] boys [[UnusualEuphemism run the train]] on the one female in the group (consensually!) as a way to reforge the bond between them and find their way out of the sewers. It's used as a metaphor for leaving their childhoods behind.
* In ''[[{{Deryni}} The Quest for Saint Camber]]'', Kelson has a vivid dream of marrying and mating with Rothana during his ''cruaidh-dheuchainn''. Meanwhile, Dhugal observes a young female Servant named Rhidian disappear through another door near the underground chapel (the girl is gone for an hour); he later speculates that Kelson participated in some kind of sexual initiation or ritual marriage, but he doesn't share this idea with Kelson.
* In the ''Literature/ApprenticeAdept'' series, werewolves can only receive full adult status (conferred by a fourth syllable in their name) by going through a ritual first mating (A female chooses a male to mate with when her first heat comes. There's no chance of pregnancy, but the two are barred from mating with each other again)
* In the sci-fi novel ''[[Literature/GreatwinterTrilogy Eyes of the Calculor]]'' a fifteen-year old youth is going off to fight a duel against a more experienced opponent. He intends to stop off a brothel first because dueling as a virgin is regarded as bad luck, but the 22-year old maid seduces him figuring she'd be a better inspiration to live than some anonymous whore.
* Discussed in ''TheBadSeed'': during a discussion with friends, {{Motormouth}} Monica Breedlove mentions how much she despises sex being treated as a rite of passage in fiction; she feels sex is just another life experience, nothing more, nothing less, and goes into a surprisingly funny rant about how she would rather read a story about a boy casually losing his virginity to a prostitute.
* A major part of Johnny and Owen's growing up in ''Literature/APrayerForOwenMeany'' by John Irving concerns the efforts of Johnny in particular to find a girl. However, it's [[SubvertedTrope subverted]] when the adult Johnny of twenty years later admits he is still a virgin and no longer has an interest in changing that.
* ''ClanOfTheCaveBear'' series, in a rare female example in Jondalar's Cro-Magnon culture a girl's first time happens shortly after her first menses and is called First Rites. They can pick whichever eligible and consenting man they want to perform the ceremony. Boys get special training so that they will ensure the girl has a good time. A man's first time isn't really as specially celebrated although men who are frequently asked to perform First Rites are considered quite the stud. This is contrasted with the Neanderthal culture that raised Ayla, where sex is something men demand whenever they want, of any woman, who will immediately assume the...position. A young man who hated Ayla raped her repeatedly this way in order to flaunt his power over her and punish her for being herself, even though there was no sexual stigma.
* In ''Literature/{{Xanth}}'', this is referred to as "joining the Adult Conspiracy", as the details thereof are a closely guarded secret.
** Though simply knowing how [[ExactlyWhatItSaysOnTheTin "stork summoning"]] is done is enough to become part of the Conspiracy. Jenny Elf and Gwenny Goblin are shown uncensored Tapestry pictures of a couple going at it, in order to initiate them, as they needed the knowledge to complete their Humphery-given task. (Che didn't count; as a centaur he already knew the "raw facts")
*** This trope is played so straight that in one book, the plot kicks off with a goblin having to take her kid brother to a forgetfulness spring, because he's gained tremendous power just by learning to ''swear''. Lord knows what would have happened if he'd found out about stork summoning.
* The ''MilesVorkosigan'' series has Miles' first time described in his thoughts and fitting the FeudalFuture, it matches a traditional one of European aristocrats- on a "Grand Tour". Miles went to [[PleasurePlanet Beta]] and had his first experience with a woman who had a fetish for those deformed like himself. When he saw her with someone else, he tried to slit his wrists and was only stopped from suicide by [[BattleButler Bothari]] (the context of Miles' memory is that he knows Bothari was a psycho, but he also remembers Bothari's kindness to him).
* In ''Literature/TheIronDragonsDaughter'', girls have a [[ICallHimMisterHappy "naming ceremony"]], in which a good experience will render their ladybits "pliant and a friend for life". It's implied that boys have a similar rite.
* This trope is common in the books that MissMarple's nephew Raymond West usually gives her to read, and Miss Marple hates it. Not because of any squeamishness about sex, but because of the rite-of-passage bit; she feels that it removes all the romance and mystery from sex and reduces it to something roughly equivalent to taking a vitamin pill.
-->Sex as a word had not been mentioned much in Miss Marple's day, but there had been plenty of it, not talked about so much, but enjoyed far more, or so it seemed to her. Though usually labeled Sin, she couldn't help thinking that was preferable to what it was now, a kind of Duty....Really, to have sex urged on you as though it were an iron tonic! Poor young things.
* In ''TheRedTent'', girls in Padan-Aram undergo a ritual upon reaching their first period where they are masturbated with a small household idol by their female relatives, in order to a) break their hymen to offer the resultant blood to the goddess Inanna, and b) encourage (via orgasm) the girl undergoing the ritual to [[DreamingOfThingsToCome dream about what her destiny holds]]. (The Canaanite women, who do not do this ritual, view it as {{Squick}}.)
** In the same book, [[LoveInterest Prince Shalem]] mentions having been [[ProfessionalSexEd 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 [[TheProtagonist Dinah]].
* Apparently, Beowulfans in the ''Literature/HonorHarrington'' 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 [[AttemptedRape more than]] self-image issues that made Honor a CelibateHero for so long. She was ''pissed'' when she found out.
* In Creator/IsaacAsimov's ''Literature/TheGodsThemselves'', there's an alternate universe and humans have discovered absurdly cheap power by exploiting the different rules of their universe and ours. In the alternate universe, there are three kinds of gaseous people and a kind of solid people. [[spoiler: the solid people are the merging - which is their analog of sex - of three gaseous people]].
* In ''TheEpicOfGilgamesh'', the wild Enkidu only becomes a civilized man after he has sex with the temple prostitute Shamhat.

[[/folder]]

[[folder:Live Action TV]]
* [[SubvertedTrope Subverted]] in ''[[Series/BabylonFive Babylon 5]]'': the ranger Marcus Cole admits to Ivanova that he is a virgin, and is saving himself for the right woman (i.e. Ivanova). He seems completely at peace with this; Ivanova feels sympathy for him, but he neither needs nor desires her sympathy.
** [[spoiler: He never does lose it, either, instead dying to save her life.]]
* The ''{{Firefly}}'' episode "Jaynestown" dances back and forth between playing this straight and [[SubvertedTrope subverting]] it. Inara, the show's HookerWithAHeartOfGold, is hired by a rich snob to "make his son a man." The son has much more confidence afterwards, but it's not clear how much was meant to be attributed to the sex and how much to Inara's pep-talks before and after.
** The son's remark "YOU wanted to make a man of me. I guess it worked," implies more that it was the pep talks, since the father's behavior clearly indicates that by "a man" he meant "the same downtrodden kid but now he's had sex".
*** Or it was referring to the fact that his actions directly contradicted his father's orders, and he was therefore standing up to "the man" himself.
* On ''MarriedWithChildren'', much of the humor of the Bud Bundy character centers around his pathetic and increasingly desperate attempts to have sex, and his sister Kelly repeatedly teasing him for it.
** He has an active sex life, but he lacks partners...
** He did lose it at some point though. Didn't he have sex with Al's boss(female)Gary
** Uninspiringly enough, despite being a one-handed-stud, Bud still suffers from the HollywoodDateless trope.
* On the HBO series ''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.)
** [[CrowningMomentofFunny ''"Octavian, have you penetrated anyone yet?"'']]
** Also note that Atia at this time believes Octavian has been penetrated-by Uncle Caesar, because he can't tell her where they disappeared to one night(Caesar was actually having an epileptic seizure). But the Romans saw it as necessary for Octavian to do the penetration to become a man.
* With the exception of Harry, this occurs to the aliens on ''[[ThirdRockFromTheSun 3rd Rock From The Sun]]''. Harry was implied to have had sex in an early episode and it was presented as a joke that someone that clueless actually "got some", but the other three Solomons lost their virginity with great fanfare.
* Loss of virginity is a big aim of all the main characters in ''TheInbetweeners''.
** Which leads to a hilarious reveal in the final episode with [[spoiler: Neil]].
* Sid of ''{{Skins}}'' is under pressure from his best friend Tony to lose his virginity, as Tony is embarassed to be friends with a virgin. JJ in the third season is also miserable about being a virgin, especially when his two best friends manage to be very sexually successful, but eventually his lesbian friend Emily sleeps with him out of pity.
* In a flashback ''Series/HowIMetYourMother'' showed us how Barney losing his virginity to Rhonda "The Man-Maker" French turned him into TheCasanova we know today.
* In ''Series/{{Glee}}'', Finn loses his virginity to Santana, believing in this trope. but was incredibly regretful about it immediately afterwards and the following Monday denies he lost it yet.
* On ''BoyMeetsWorld'', Cory and Shawn say that their prom night will be "the night we leave as boys and come back as men", and both try to persuade their respective girlfriends to have sex for the first time. Cory and Topanga almost go through with it, but [[LetsWaitAWhile decide not to in the end]], and Shawn and Angela, well... the episode ends [[DidTheyOrDidntThey without resolving that plotline]] and it's not mentioned in the subsequent episodes.
* [[SubvertedTrope Subverted]] in an episode in ''{{Series/MASH}}'' with a wounded soldier who is taunted by his for waiting to have sex until marriage. He finally has enough when they deal him a hand of pornographic cards just to tease him for being flustered and claims to be volunteering for a dangerous mission, even going so far as to request the necessary paperwork to do so. He is ultimately convince by Potter that he shouldn't do anything he is uncomfortable with, be it sex or putting his life in even greater risk, in order to prove himself as a man to anyone.
** Also subverted a couple of times with Radar, most notably in the "Fallen Idol" episode.
* Slightly parodied in ''Series/GameOfThrones''. Tyrion and Bronn set this up for Podrick (with three high priced prostitutes). When he comes back, as awkward and boyish as ever, still carrying all the money they assume he refused to go through with it. Apparently [[spoiler:he impressed them so much they forgot to ask for the money]].
** Not only that, [[spoiler:upon hearing he still has the money, "Sit down Podrick," Tyrion says. "We're going to need details. Copious details." What they hear apparently impresses them so much that they are still talking about it the next episode.]]
* Used as the main focus of an episode of ''NewGirl''
[[/folder]]

[[folder:Other]]
* The internet legend ''Densha Otoko''/''Franchise/TrainMan'' is the story of a virgin {{Otaku}} who falls for a woman he saved from a [[TheChikan train groper]]. While he does throw out his Otaku-ish things once he realizes he's fallen in love with her, his real enemy isn't his desire to prove himself so much as his own self-confidence.
* In some ancient cultures, prostitutes were expected to help a young man lose his virginity, so that by the time he got married, he'd know what he was doing.
** Fun fact: these "ancient cultures" included medieval Catholic Church. Yep. The prostitutes were considered a necessary evil, allowing [[ValuesDissonance young men]] to [[UnusualEuphemism let loose the steam]] before the marriage and thus preventing extramarital sex.
*** There was also the fear that those young men would turn to each other to...relax. Female prostitutes were better than male friends helping each other out.
** Not only that, this was actually quite common in Western Europe until *TheTwentiethCentury*. There was also less real stigmatization of prostitutes themselves, added to the fact that wives were [[DoubleStandard expected to stay virgins until marriage]] while husbands were supposed to... be more knowledgeable by that point. It still happens, although it's for the most part a DiscreditedTrope. Still somewhat accepted in [[ValuesDissonance other parts of the world]] for much the same reason.
** Apparently one reason the Zulus were so feared in battle was that they had entire regiments of young men who were not allowed to have wives before they killed their first enemy, no doubt exacerbated by the other groups of older soldiers who were married. So you can guess how motivated the young ones were...
[[/folder]]

[[folder:Music]]
* Music/BobSeger's "Night Moves".
* Mentioned in some ParentheticalGirls songs, and the focus of "Unmentionables."
* "Strawberry Wine" by Deanna Carter is a RareFemaleExample.
* The main topic of the song "Sic Transit Gloria" by Brand New
* T.G. Sheppard's 1982 hit, "War Is Hell (On The Homefront Too)" has a man recalling how he lost his virginity to an [[MrsRobinson older woman]] while her husband was away fighting in WorldWarII.
* Mondo Rock, "Come Said the Boy"
* "En Het Werd Zomer" by Dutch singer Rob de Nijs, about a guy seduced by a girl one summer day and becoming "a man" afterwards.
* "Nothin' Like the First Time" by LadyAntebellum.
* Main focus of "La Première fille" by French singer Georges Brassens. The narrator goes on to detail all the different girls it could have been, and all the different ways it could have happened, regardless of which he will always remember his First. This incidentally allows the narrator to imply [[TheCasanova a very rich]] sexual life on his part by enumerating random female names saying that they'll all be forgotten long before he forgets TheOne. Brassens uses the phrase "baptism of love" whih is exactly this trope, as well as SelfDeprecatingHumor about how awkward and nervous he was while trying to keep his cool which could imply this trope in retrospect.
* "Summer (The First Time)" by Bobby Goldsboro.
* "This Girl Is a Woman Now" by Gary Puckett and the Union Gap is a RareFemaleExample.
[[/folder]]

[[folder:Video Games]]
* The AdventureGame series ''VideoGame/LeisureSuitLarry'': This is the entire plot of the original game, starting with Larry's desperate attempts to visit a prostitute before trying to find "True Love". In fact, failing to have sex before sunrise in the original game results in a NonstandardGameOver, as Larry, sworn to lose his virginity by the end of the night, commits suicide. He even gets technical about it after visiting a prostitute and deciding that prostitutes don't count.
* Rare female example in ''[[BaldursGate Baldur's Gate II]]:'' if the player romances Aerie, she asks to sleep with the protagonist at the end of her romance arc to prove herself a woman rather than a girl. Accepting her offer leads to the ''bad'' ending of the romance-the good ending has the player teach Aerie the distinction between sex and love. The good ending leads to Aerie's continued romance arc in ''Throne of Bhaal'' where this trope is visited again as Aerie, very much in love, asks the protagonist to sleep with her again-not to become a woman, but because she loves the protagonist, and sleeping with her is the good path.
* Used ([[ButNotTooGay somewhat euphemistically]]) in conjunction with the ComingOutStory for symbolic value in ''VideoGame/BlazeUnion'' as the final arc of [[ComingOfAgeStory the canon route]]. Gulcasa, grieving over Siskier's death and left stricken by being forced into [[SelfMadeOrphan symbolically committing matricide]], turns to Nessiah for comfort. His childhood friend Jenon and his remaining mentor figure Medoute sense that something is different about him, but don't understand what until Medoute witnesses a sexually charged scene between Gulcasa and Nessiah while spying on them.
* Alistair in ''VideoGame/DragonAgeOrigins'' [[SubvertedTrope subverts this trope]] by refusing female!Gray Warden sexual advances until he falls in love with her, despite the fact that he admits sexual attraction and current virginity.
* In-universe example in ''VideoGame/NoOneLivesForever 2'', when the backstory of the traitor from the first game is explored. A series of audio diaries reveal that he trained rigorously to take on the role of a super-spy, but being unable to pick up women leaves him feeling inadequate. This changes when the last tape is found...
--->"She wasn't good looking and she smelled like a horse, but she was woman enough for me. My last obstacle to becoming a super-spy has been conquered. As of today, I am no longer a virgin! YEEEEEEEEEEHAAAAAAAAAA!"
* In ''VisualNovel/KatawaShoujo'', this is the case for [[spoiler:Hanako Ikezawa]], another rare female example. [[spoiler:She allows Hisao to have sex with her even though [[FanDisservice she's obviously uncomfortable]] and ''neither'' of them is emotionally ready, because she wants him to stop seeing her as [[DontYouDarePityMe someone that]] [[DeclarationOfProtection needs protecting]]. (Even more so, after their sexual act Hisao mistakenly ''thinks'' that [[SexualHarassmentAndRapeTropes he forced Hanako into sex]], and while explaining this trope Hanako has to dispel these fears too.)]]
* Taketo Kanzaki's sequel in ''VisualNovel/ClassTripCrush'' takes an interesting angle on the trope. Early in the route, Taketo and the protagonist agree to have sex if Taketo's high school soccer team wins an upcoming national tournament; when an accident leaves Taketo with a cracked rib just before the tournament begins, that promise is one of the main things behind his determination to get back onto the field in spite of his injury. In fact, the protagonist is looking forward to it almost as much as Taketo is and there's no real reason that victory has to be a requirement - except that Taketo wants it to be as momentous and meaningful as possible, and won't settle for less than winning the tournament [[spoiler:and ending his soccer career on a high note]] beforehand, to the point that if the team ''doesn't'' win, he decides to wait and try again at the ''summer'' tournament... rather to the protagonist's disappointment.
[[/folder]]

[[folder:Webcomics]]
* For a long time, ''Webcomic/MenageA3'' manifested this trope in seemingly pure form with Gary, the desperate, confused geek virgin. Then Gary got laid, and his story turned into a [[SubvertedTrope subversion of the trope]]: he became a desperate, confused geek ... who occasionally has sex. He's still Gary.
* Taken to the [[http://www.pvponline.com/2008/05/27/innocence-lost/ logical extreme]] with Francis and Marcy of ''Webcomic/PvP'' when they [[http://www.pvponline.com/2008/05/28/ding/ lose their virginities to each other.]]
* [[http://pbfcomics.com/?cid=PBF191-Boy_Scouts.gif This strip]] of ''ComicStrip/ThePerryBibleFellowship.''
* Christian Weston Chandler's Self Insert Character in ''Webcomic/{{Sonichu}} ''is just as desperate to lose his virginity as his RealLife counterpart. Hilariously (or disturbingly, or a little of both) when he does finally get laid it's by ''tricking'' a woman into having sex with him...and he ''brags'' about it.
* In ''ScaryGoRound'' when The Boy loses his virginity he immediately becomes a MAN, and resolves their problem. Once he's done though, he's expended all his strength and reverts to "callow youth".
[[/folder]]

[[folder:Western Animation]]
* One episode of ''WesternAnimation/AmericanDad'' parodied this plot, in full-blown DoesThisRemindYouOfAnything style. Stan is upset because although he is a CIA agent, he has never killed a man, and ARealManIsAKiller. So he sets out to find the right person to be his first kill.
** The episode "Failure Is Not a Factory-Installed Option" episode [[MomentKiller has a repo-man telling Steve "Well you may have planned on becoming men through sexual conquest, but perhaps an equally valid preparation for adulthood would be a night filled with disappointment and compromise."]]
** The first several episodes of the series had subplots about Steve trying to score with girls. Luckily, [[CasanovaWannabe this aspect]] of his character [[CharacterizationMarchesOn was later downplayed]].
* ''WesternAnimation/BeavisAndButtHead'': In probably one of the greatest speeches of all time, [[http://www.trilulilu.ro/Vanecika/54ec165dccd6bf Beavis talks about]] how he and Butthead are never going to score, and grow old without having sex.
* Butters from ''WesternAnimation/SouthPark'' getting his first kiss in "Butters' Bottom Bitch" is an obvious metaphor for this trope.
* An early episode of ''WesternAnimation/TheClevelandShow'' dealt with the double standard with this trope. He tries to prevent his step-daughter from having sex while trying to get Cleveland jr. to lose his virginity.
[[/folder]]

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