Their First Time

Listen, they say the first time ain't the greatest,
But I tell you, if I had the chance to do it all again, ooo
I wouldn't change a stroke, 'cause, baby, I'm the most
With a girl as fine as she was then.

— Prince & The Revolution, "Raspberry Beret", Around the World in a Day

Related to Will They or Won't They?, Their First Time is when a couple decides to have sex for the first time. Or at least talk about it. The more planning they put into it, the less likely it is to happen.

The fact that the fictional sex act tends to happen in a spontaneous moment is the Unspoken Plan Guarantee in action. When someone spends time researching sex, thinking it over, or talking about it with her intended partner, this lessens the odds it will actually happen. This usually ends with the couple calling a halt until they're "ready." On the other hand, when circumstances have put the two together with no warning, "ready" happens in about 30 seconds — just enough time to ask "Are you sure?" before then going for it. What's implied is that the less conscious thinking about it, the better. (Or perhaps all the thinking they've already done has only heightened their anticipation.)

With teenagers, this could well be the entirely unintended reaction between the opposite approaches to sex among teenagers; writers who depict it as harmless and are willing for the characters to have sex won't require the incessant talking beforehand, while those who are less comfortable (or whose audiences are) will be sure to avoid it, or depict it as bad, but either way be sure to have lots of angsty talking about it.

Keep in mind, the trope is Their First Time. It doesn't necessarily have to mean that either party is a virgin, only that it's the first time for those two particular people.

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Examples:

Anime & Manga

• Chapters 137 to 139 of Ai Yori Aoshi are dedicated to Aoi and Kaoru finally being able to have sex, after they're able to say "screw you" to their families and stay together.
• Tatsumi and Mine are implied to have done the deed together in Chapter 50 of Akame ga Kill!, having started dating a few chapters prior. It's confirmed that they did in the final chapter, where Mine is revealed to be pregnant.
• Promiscuous (only in theory) Yamada of B Gata H Kei tries to do this, failing miserably in hilarious ways. The entire show revolves around it; there's a reason one of the alternate titles is "Yamada's First Time."
• Guts and Casca of Berserk have their first time at the end of Volume 9 in Chapters 46 and 47 (also in the third episode of Berserk: The Golden Age Arc). Neither of them are very experienced in the act, Casca being a virgin, and Guts having a very ugly prior sexual experience. When Guts flashbacks to his rape at the hands of Donovan in the middle of the act, it very nearly results in Casca getting strangled to death. But after Guts comes to his senses and bares his soul to Casca, Casca gives herself to him, and the two more than proceed to make up for how it started.
• Bloom Into You: Touko and Yuu have sex in the penultimate chapter, in which Touko invites Yuu over to her home while her parents are away.
• Bokura no Hentai doesn't present these too positively:
  • Tamura's first time was while he was crossdressing, because his crush was straight and wasn't attracted to boys. Tamura ends up passing out due to the pain.
  • Ryousuke and his girlfriend Hacchi have their first kiss which leads into this, but Ryousuke kept thinking of Marika the entire time.
  • Subverted with Marika and Tamura. She stops before anything happens. Though earlier in the manga Tamura did touch her, which depending on your definition counts.
• Subverted in episode twelve of Btooom!. After Taira dies and Himiko confirms to Ryota that she is indeed the girl he fell in love with online, they kiss and start foreplay. However, Ryota realizes that Himiko, while willing, is terrified because of her PTSD from Attempted Rape, so he stops and just cuddles with her. This is treated as part of Ryota's maturation.
• Cross Ange: In Episode 22, after Tusk returns from his Disney Death in the previous episode, Ange gives him a Slap-Slap-Kiss, then, just to convince herself that he is indeed real and not dead, she mounts him and orders him not to go anywhere, as the tune of "Necessary" kicks in. They proceed to make love next to the ocean, finally ending the Unresolved and Belligerent Sexual Tension that had been building since Episode 5. It is notable for being the one sex scene in the show that isn't solely fanservice or a rapey form of Fan Disservice, and the entire scene is wholly tender and romantic. According to Tusk when he later fights Embryo in Episode 24, he and Ange went on for three days and nights.
• A plot point in Crying Freeman. Both Yoh Hinomura and Emu Hino are virgins, and since she witnessed one of his murders, she's his soon-to-be victim. When Yoh goes to her Big Fancy House, Emu tells him that he can kill her and she won't refuse... but as her last wish, she asks him to do it with her. Yoh tells Emu that he's a virgin too and accepts to be her first and last - and not only do they "deflower" each other, but he falls for her and takes her in.
• Surprisingly, it's the Beta Couple of DARLING in the FRANXX Mitsuru and Kokoro who end up in bed together first instead of Hiro and Zero Two. In episode 17, having found a book on childbearing in Ruins of the Modern Age in an earlier episode, Kokoro propositions Mitsuru. He initially rebuffs her, but after the group is confronted by the Nines and their COs, who insist their reproductive organs and emotions are just needed to pilot the FRANXX and an inconvenience otherwise, the pair sleep together in what is as much an act of defiance as an expression of their love.
• The very first page of Domestic Girlfriend starts with Natsuo and Rui losing their virginities to each other just for the experience. Neither of them is particularly impressed. When Natsuo starts dating Rui's sister Hina and they have sex, she is surprised that he actually knows what he's doing because she doesn't realize he's already had sex (and learned his lesson from those mistakes).
• Subverted between Clara and Mei in Don't Meddle with My Daughter!. Their first time together was in "Honey Hold me Tight's" first chapter, except Clara was possessed by a parasite at the time. Once the parasite was destroyed, they lost all conscious memory of the event. So as far as they're aware, their first time wasn't until the third chapter - when Clara gives Mei her virginity.
• In Fushigi Yuugi, Miaka and Tamahome decide to just go for it (Miaka's Virgin Power be damned!), because they're about to face Nakago and don't know if they'll survive to do the deed again. So they get started... and Miaka's stomach growls, which embarrasses her and turns off Tamahome. They finally do the deed on their honeymoon later, and Miaka gets pregnant. Which is VERY important in the Eikoden novels.
• A minor subplot in Futari Ecchi has Makoto Kawada's teenage sister Jun and her sexual self-discovery, which of course includes this. Not to mention, Makoto and Yura were both virgins in their wedding night (which was hilariously awkward), and pretty much the whole manga is about having this as a starting point to improve their sex life.
• Pretty much the whole chapter 52 of Future Diary is dedicated to Yukiteru and Yuno "becoming one", the "happy end" foretold by Yuno's future diary at the start of the series. Twisted soon after, as Yukiteru decides this peaceful afterglow is the best time to confront Yuno about Akise's dying message and she goes Ax-Crazy. Which is to say, she's still in her underwear, but now she's chasing him and literally trying to kill him with an axe.
• In Girl Friends (2006), Akko tries to have her first time with a guy at a party. However, he's unable to get it up, and it never ends up happening. The two are both so embarrassed by it (him that he failed to perform, she that she wasn't able to turn him on) that they both agree to pretend they did go through with it. In reality, Akko's first time is with Mari after they get together, and goes by much more smoothly.
• The Great Snake's Bride: Miyo and Daija have a difficult time consummating their relationship since Miyo is an average human woman and Daija is a snake the size of a house. Miyo panics when she first sees what his genitalia is like. It takes them several attempts to go all the way, but they manage.
• GTO: The Early Years: In Chapter 135 ("Night of the Young Lovers"), Ryuji and Nagisa do it for the first time (with their friends sleeping just on the other side of a curtain).
• Hori and Miyamura in Horimiya have their first time in chapter 37 after Hori worries that she's not cute enough to be Miyamura's girlfriend (due to not being afraid of horror movies).
• Hajime gives some details on his and Kaoru's first time in season 2 of I Can't Understand What My Husband Is Saying. It's never specified when it was (anytime from when they started dating to their honeymoon).
  Hajime: Speaking of which, when I broke her hymen, I looked for (the undo button) too— [Kaoru punches him in the back of the head.]
• Kaguya-sama: Love Is War:
  • It's hinted at multiple points throughout the series and outright confirmed in chapter 138 that Kashiwagi and Tsubasa slept together for the first time during summer break.
  • Kaguya and Shirogane have their first time in Chapter 220 when Kaguya stays the night at Shirogane's apartment while his father and sister are out. It wasn't fully intended, however. While Shirogane at first definitely wanted to do it with Kaguya, her anxiousness led him to asking if they should wait. They settled for holding it off before sharing a kiss... and then Smash Cut to next morning where Kaguya and Shirogane are laying under the covers naked. According to Kaguya, their kissing got them excited to the point of having sex, anyways.
• Maison Ikkoku: Godai and Kyoko finally sleep together in chapter 149.
• Mobile Suit Gundam SEED: Poor, poor Kira Yamato. His first time was with Flay Allster, who was attempting to manipulate him into exterminating the rest of his entire race.
• Molester Man: Molester and Kansai finally have sex in chapter 18.
• In episode 21 of Parasyte, Satomi invites Shinichi over to her house, where they finally do it.
• In the backstory of Rurouni Kenshin, Kenshin lost his virginity with his First Love Tomoe. As a bonus, it takes place when it's snowing.
• Ann and Daigo, totally unplanned, in an empty shack in Sand Chronicles. She mostly does it to re-affirm her love for him after he gets insanely angry and jealous at Fuji for kissing her. Presented with a Fade to Black and later affirmed.
• It's hinted in Shaman King that Yoh Asakura and Anna Kyouyama slept together right before he left Japan to go fight in the Shaman Tournament. Later, it's confirmed: the canon side story set in the future has their son Hana as the main character, and if you trace his age to Yoh's and Anna's timeline in the Shaman Tournament, you'll see that Anna was in the early pregnancy stage for the last arcs.
• The Shin Kimagure Orange Road movie has Kyousuke and Madoka finally doing the deed almost at the end. It also overlaps with First-Name Basis, as Kyousuke finally gets used to calling Madoka by her first name instead of Ayukawa.
• Subverted in the Sword Art Online anime adaptation. At the point in the web novel and the books where Kirito and Asuna trade virginities, in the anime they spend the night in bed together but don't actually have sex: Asuna is willing but they're both too nervous to actually do the deed. Instead they decide to get in-game married.
• Tales of Wedding Rings: After many interruptions and instances of them chickening out for one reason or another, Hime and Satou finally give each other their virginities in Chapter 56.
• The whole of Tokyo Ghoul:re chapter 125 is dedicated to Kaneki and Touka's first time.
• Chapter 200 serves as this for the main couple of A Town Where You Live, after many false starts. Alternative "first time" chapters were published with anime volumes, and also serve as alternative endings with other heroines.
• Touta and Kuroumaru from UQ Holder! have sex right after they finally become a couple in chapter 181.
• In Volume 17 of X1999, Sorata asks Arashi to give him her first time and she does. The bad news is she can't be a Dragon of Heaven anymore after losing her spiritual powers along with her virginity.

Comic Books

• Batman: After years of dating on and off, Stephanie Brown and Tim Drake finally decide to have sex after defeating Flashpoint Gorilla Grodd in Convergence (it's Tim's first time with anyone, though not Steph's). Humorously subverted when they find they are both too bruised and sore from their injuries to go through with it, so they end up in a Sleep Cute instead.
• Blue Is the Warmest Color: After being followed to her home by Clémentine, Emma tells her she didn't want to take her home because she feared being unable to refrain from acting on her desire for her. They then passionately have sex.
• The Sin City series begins with the main character losing his virginity to a beautiful young woman. Then the girl gets killed right in their bed, and said main character is framed for her murder. Since this is a Crapsack World, he decides to not even bother clearing his name and goes straight to searching for the real killer/killers for revenge, alongside the woman's twin sister...
• Spider-Man: The first openly sexual relationship Peter had with any of his girlfriends was with Mary Jane Watson and the end of The Amazing Spider-Man (1963) #149 is generally acknowledged as the consummation of their love, albeit via a Sexy Discretion Shot:
  Peter: Mary Jane! Lady, am I ever glad to see you.
  Mary Jane: Do you mean that Tiger? For real?
  Peter: Come here...and I'll show you. (Shuts door to the reader).
• Zot!: Zot and Jenny spend an entire issue discussing whether they're gonna. They apparently come to the answer "not yet", but then again the issue ends with her following Zot into his interdimensional suitcase (it's that kind of book). What they did in there is up to the reader.

Fan Works

• Advice and Trust: After getting together Shinji and Asuka spent a while trying to define the limits of their Secret Relationship. During a talk Shinji told Asuka that, even if making out was nice, he was willing to take it slow because their relationship was special and he did not want to screw it up. Later, after nearly getting killed by Leliel, Asuka tells Shinji that she wants to bond with him completely because they might get killed at any time and she does not want to have any regrets. So they have sex that night.
• In Angel of the Bat: Times of Heresy, after some build up and a particularly good date, Cassandra's girlfriend Sadie attempts to initiate the couple's first intercourse. There is a tiny bit of lime, but the two don't even get their clothes all the way off before Cassandra refuses and clarifies she's waiting for marriage. This is one of several factors that drives a wedge between the two.
• As Fate Would Have It: Following their Relationship Upgrade and several subverted attempts, Nate and Yancy finally do it for real in Chapter 13.
• Back To Us has Adrien and Marinette consummate their relationship at the end of chapter 35.
• In the Kill la Kill fanfiction Before My Body Is Dry, the epilogue fic First Comes Love has Ryuko staying with Akio in the midst of a typhoon. After some time spent together dancing, they end up making love after some Tickle Torture. While the act is not shown, Akio and Ryuko are shown laying in bed together, under the covers and fully naked, the next morning.
• In Best of My Love, it's subverted at one point after Meng Yao, who is on the ace spectrum and thus is very infrequently interested in sex, loses interest midway through after initiating and then panics. Lan Xichen immediately stops and calms him down. Their actual first time, later in the fic, is a mixture of funny and heartwarming when Meng Yao is finally comfortably ready to do the deed and texts Lan Xichen — who was at breakfast with his family and hurries across town.
• In Black Sky, Xanxus and Dorea's wedding night is that, as Dorea used a bridal ritual to bond with her groom and it wouldn't have been efficient if both parties hadn't been virgin.
• Bridge to Terabithia 2: The Last Time ends its final chapter with Jess and Leslie, both 18 at this point, finally doing it, the day before they're leaving Lark Creek for university. The story abruptly cuts away from the two at that point, before following with a Time Skip to the Distant Epilogue where 13 years later, Jess, Leslie, and their children are attending Maybelle's wedding.
• The My Hero Academia fanfic burn it all down uses this as a plot device.
  • There is special attention given to Hawks and Dabi's first time, as Hawks is a Technical Virgin (he only had intercourse with a woman before and it's unclear how far it went as he realized for sure that he's gay, and never had sex with a man before). Dabi, who was originally just planning for a quick fuck, is completely taken aback by this casual admission, and asks Hawks repeatedly to clarify exactly how much experience he has with men (none). Afterwards he completely switches gears and becomes incredibly attentive while taking it slow and checking for consent and discomfort every step of the way. This becomes a turning point for the rest of the fic, as Hawks' Moral Dilemma about losing his virginity to the villain he was supposed to spy on leads to a long series of Disaster Dominoes that leads to torture, uncovering a huge Government Conspiracy, and a truly astounding level of property damage. On a less disasterous note, Hawks takes the lessons of that first time to heart, which comes in handy when Dabi opens up about his past of being raped, as Hawks refuses to engage in Dabi's horrible coping mechanisms of dealing with that trauma, making it clear that being kind and attentive was the standard he set and he was going to stick to that.
  • Shouto and Bakugo's first time is also briefly mentioned (though not shown in any detail due to the two of them being underage), but also becomes plot critical. The location they pick is Hawks' apartment, which as a result of the Disaster Dominoes mentioned above is bugged by the Hero Commision after they become suspicious of Hawks. This leads to them attempting to kidnap Bakugou to use him as leverage.
• Light loses his virginity to Ryuk in A Charmed Life.
• The Child of Love: The whole story happens because Shinji and Asuka had sex for first time, but since they were not ready yet for getting together and having sex their relationship soured for a while.
• Coby's Choice: Luffy and Nami have sex for the first time in Skypiea after slipping away from the celebration of Eneru's defeat.
• In Chapter 35 of The Command Quarters, Starscream attempts to lose his virginity to Megatron (keeping his lack of experience a secret), only to learn that Megatron is also a virgin.
• A Crown of Stars: When Asuka and Shinji tried to make love for first time -in the previous story- it was a mess because they were heavily traumatized and Asuka had been virtually and constantly raped for three years. Shinji realized he was hurting her and he refused to go on. In chapter 43, after considerable soul-searching, healing and counseling and spending a while opening up and reaching out each other Asuka asks him if he can promise her he will never leave her. They talk for a while, baring their souls, and Shinji promises, assuring her that he loves her and he is hers. Then they make love.
• Displaced (The Legend of Zelda): Up until chapter 48, Link and Zelda have refrained from having sex since Link believes it will damage Zelda's reputation; Zelda points out everyone knows they're a couple (some even think they're married), and already assume they're having sex and don't care. They proceed to do the deed.
• Elementary My Dear Natsuki: After Shizuru makes her return from the seeming dead, she and Natsuki return to their quarters at 221B Baker Street, where, after a conversation about what they actually mean to one another, they consummate their relationship, the first time for each of them. They find a tea service left by Mrs. Hudson, who also left a note, "It's about time!"
• A couple of Empath: The Luckiest Smurf mini-stories talk about the male Smurfs' first times with their female Smurf wives — the first with Empath and Smurfette, and the second with Tapper and Duncan McSmurf with their own wives. While none of the stories go into any graphic detail about them, Tapper says that his first time "was like heaven" before humbly confessing that both he and his bride were inexperienced lovers who didn't know what they were doing, while Duncan says his with his bride was rather "brutal" but worth it.
• Entre Nous (2021): Elodie fondly recalls that her first time with Laetitia was the best sex she's ever had. She'd been with other women before, but Laetitia hadn't.
• Evangelion 303: In chapter 5, after several weeks of Belligerent Sexual Tension, Asuka decides she can not hold it back anymore and tries to seduce Shinji very bluntly and awkwardly. Shinji tries to argue that they barely know each other, but she manages to seduce him.
• Feelings and Desires has Ash and Misty celebrating their first anniversary together as a couple in Cynthia's vacation villa. While Ash does want to take their relationship to a more intimate level, he suffers a mild case of Paralyzing Fear of Sexuality and thinks Misty might take it the wrong way. Misty catches wind of this and intentionally lures him into a couple of embarrassing situations for fun. It takes them having a talk about it for Ash to finally take the step and do it, knowing that she wants it too.
• The RWBY fanfic ''The First Times'', unsurprisingly, deals with this. It starts with Nora relating the time she took Ren's virginity, which involved her on top, candles that were not merely scented, and the entire building being a disaster zone when they left. Everyone is horrified when Ren confirms it's all true. Team RWBY then decide to tell their significant others about their own first times. Yang used a transfer student for practice due to knowing he was leaving the next day; it wasn't horrible, but it shows how freaked out she was that despite being impulsive and flighty, she planned the entire event down to the second. Blake was sold into prostitution for a few months following a surge in anti-Faunus racism; despite both the pimp and the john being surprisingly compassionate about the entire situation, she hardly enjoyed herself. Weiss secretly hooked up with a lesser noble girl at a homophobic rich kid retreat; when the girl got outed and dropped off the face of society, Weiss cut her out of her life with hardly a second thought—she's more worried that it means she's a sociopath. Ruby actually didn't have a first time at this point, but after hearing Weiss' story, she and Weiss make love for the first time. While Yang, Blake, and Team JNPR play games in Team JNPR's room. Yang wears noise-cancelling headphones that don't seem to help.
• In From Bajor to the Black, Eleya has her first time with a boot camp squadmate (in the back of an infantry fighting vehicle) to get back at her ex-high school boyfriend after a bad breakup.
  Eleya: Turns out sex is a lot of fun, who knew?
• Futures Freak Me Out: One month after their first real kiss, Asuka decides to take their relationship with Shinji to the next level; so she climbs into his bed wearing only two undergarments, and states she wants to do more than kissing and cuddling.
• Hetalia: Axis Powers fanfic Gankona, Unnachgiebig, Unità: Germany, Italy, and Japan actually didn't do it until they got married after months of dating. Let's just say the Bad Touch Trio announced the end of the waiting period while performing surveillance on the honeymoon ship.
• In the Hellsister Trilogy, Supergirl hooks up with Dev-Em and loses her virginity to him after the war against Mordru is over.
• HERZ: Shinji and Kurumi slept together for first and only time seven years before the beginning of the story, and it killed whatever relationship they previously had.
• Higher Learning: Although they had been making out for a long while, after Asuka's Mind Rape Shinji and she talk and decide sleeping together for first time. Later Shinji stressed that it was both their decision.
• Played for Drama in Hyrule Warriors; Link's first time is with Cia, after she cast a spell on him to keep him under her control.
• The Miraculous World of Caline Bustier: Adrien and Marinette had their first time at a bonfire party during a school trip to Spain. Future!Alix gleefully tells this story to Marinette's mother in the past, at the time when it's happening.
  Future!Marinette: At least now I know why I got grounded the second I got back.
• Naru-Hina Chronicles: Naruto and Hinata have sex for the first time after the former took over a year of dating to finally tell the latter that he loves her.
• Neon Genesis Evangelion: Genocide: After Asuka catches Shinji getting surprised by Misato in a Little Black Dress, she jumps him when they're alone and convinces him to have sex with her to prove his feelings.
• New Tamaran: The author wrote two lemon prequels - one where Starfire offers her virginity as a birthday gift to Robin, and one where Supergirl, Wonder Girl, and Batgirl describe how Robin deflowered them. Each story is meant to be a Sex Comedy involving Bizarre Alien Biology and/or Man of Steel, Woman of Kleenex, with Robin being made into both a Sex God and an Iron Butt Monkey.
• Nobody Dies plays with the trope in all sorts of interesting ways. Shinji and Asuka are in love, but due to several complications (Shinij's concern over Asuka's fragile mental and emotional state, lingering doubts on Asuka's part as to Shinji's deeper feelings toward her, etc.) have been avoiding taking that step. It takes an encounter with Lilith to get them to do it. While Yui is furious with Shinji (since they're still 16, and despite the rather logical and mature attitude they took toward it), the rest of NERV is quietly celebrating the Relationship Upgrade.
• The One I Love Is...: Rei has her first time with Shinji when she sees him crestfallen and tries to comfort him. Several months later Asuka is the one is distraught after her Mind Rape and asks Shinji loving her and making her forget the pain for one night.
• A Pleasant Surprise is about the protagonist, Midnight, losing his virginity to Fluttershy. A good amount of tension is built up, showing his initial doubts and hesitancy to go through with it, because he finally takes the plunge at the story's climax.
• Predator and Prey sees Geoff and Bridgette consummate their relationship not too long after he forgives her on the Aftermath for what happened with Alejandro on the competition (it's a long story), which also serves to signify how much more devoted and in love with each other they have become as a result of their reconciliation. Bridgette also discovers Geoff is a million times better than Alejandro, if you know what we mean.
• In the backstory of Risen, Scott Summers and Jean Grey had sex for the first time the night they got together.
  She found herself remembering the first time they had danced and the subtle transformation he had undergone, becoming more self-assured, less nervous; she had realized at that moment that this was *love*, that she wanted to spend the rest of her life with this man and die in his arms. Later that night he had told her how he felt, and she knew it was right; without hesitation she had taken him into her heart and her bed and had never looked back.
• Played for Drama in Scar Tissue. After Third Impact, Asuka and Shinji were left alone with their respective traumas. Eventually, Asuka pressured Shinji into sex, both to distract herself from the apocalypse and to prove to herself that she could control him. He felt horrible about the experience but did not stop Asuka in an attempt to make up for his past actions.
• The Second Try: After getting together in the post-apocalyptic world, Shinji and Asuka's relationship progressed slowly and steadily. They were somewhat weary and hesitant about sex, but after their first date Asuka decided that they needed to break the last barrier between them. She and Shinji talked and agreed to make love for first time.
• Chapter 18 of The Seven Misfortunes of Lady Fortune ends as Adrien and Marinette are on their way to her bedroom.
• In the Mob Psycho 100 fanfic Shigeko Kageyama AKA Mob (gender swapped) Mob is very disappointed by her first time with Teru. It's over very quickly, doesn't feel all that great, and Teru cries afterwards. She even remarks that manga and anime lied to her.
• In The Shoebox Project, James has this to say about his first time with Lily:
  James: And do you remember that time, with the toaster? It was like that only a hundred times worse and a hundred times longer and less burning and more squeezing.
• A Thing of Vikings:
  • In Chapter 12, Hiccup and Astrid have their first on the diplomatic trip to Norway.
  • In Chapter 22, Ruffnut and Magnus have their first time after their wedding.
  • In Chapter 40, after having a heart to heart Fishlegs and Heather decide to finally have sex.
  • In Chapter 47, Hiccup and Wulfhild have their first time.
  • In Chapter 60, Cami and Merida have their first, and are immediately caught by Merida's mother.
  • In Chapter 91, we see the aftermath of Tuffnut and Mór's first time.
  • In Chapter 98, Sigurd, Sophia, Heidrun, and Gunnar have sex with each other for the first time.
  • In Chapter 132, Picknose has sex with Mairwen and Signy respectively for the first time.
• Thousand Shinji: Although they had gotten together and made out many times, Shinji had not tried to take his relationship with Asuka further. When Asuka asked him about it, he answered he knew that she was still afraid and vulnerable, and if he tried to sped things up he might hurt her... and he would never forgive himself if it happened. So he would wait until she felt ready. In chapter 13, Asuka finally decided going a little further and she and Shinji bonded.
• The Marvel Cinematic Universe fic "Tingle" features a polyamory relationship between Peter Parker, Kate Bishop and Yelena Belova, with one of their first rules being that they will only have sex when all three of them are ready even if they have no problem with two going on dates without the third. As a result, they first have sex only after dealing with their initial threat of the Spot's gang, in Chapter 20 of the fic, despite having been dating since Chapter 12.
• Raven and Jinx have their first time in the fourth chapter of To Catch A Raven. Raven's demon side ends up coming forth, turning her skin red and giving her four eyes.
• As revealed in a flashback during the Fruits Basket fan fic Unshakable, Akito lost her virginity to Shigure when she was 14 and Shigure was 21.
• In the final chapter of X-Men: The Early Years, Scott Summers and Jean Grey get together and head back to the mansion in order to consummate their relationship.

Film — Live-Action

• 100 Girls: Matt lost his virginity to a mysterious girl whom he got trapped in an elevator with while a blackout happened. Since he couldn't see what she looked like, he searches for her over the rest of the film.
• In Aaron Loves Angela, Aaron takes Angela to the private room Willie showed him so they can have sex. When Angela realizes what Aaron wants, she starts crying and runs away, thinking he sees her as cheap and not believing him when he says he's never had sex before, but later she comes back and they have sex on the mattress.
• Above the Shadows: Holly has never had sex, which given that she's invisible to most people isn't too surprising, as she confesses when getting intimate with Shayne. In fact, she isn't even sure what to do (this seems less believable). Regardless, she loses her virginity to him offscreen.
• Adam (2019): Adam, who's 18, first has sex while with Gillian while presenting himself as a trans man using a strap-on.
• Alena: Near the end of the film, Alena and Fabienne have sex after both realize their mutual attraction.
• One of the main subplots of American Pie, under the pact of Jim, Kevin, Finch and Oz to lose their virginities during their senior year of high school, is that of already-established Official Couple Kevin and Victoria going through their first time at the prom. It got awkward. Then they broke up after they did it.
• Happens again in American Reunion with the girl Jim used to babysit.
• In Bonjour Monsieur Shlomi, Shlomi and Tehila intend to have sex at her house while her parents are out. They get as far as taking off their clothes before Shlomi leaves due to his feelings about Rona.
• Booksmart: Amy tries to have her first time with Hope, but as she's never done it before, she ends up doing this wrong. They stop after she drinks to steel herself, then vomits on her lover.
• Conan the Barbarian (2011): Tamara has sex with Conan near the end of the film, consummating their obvious mutual attraction, and loses her virginity by doing so.
• Daylight (2013): In a flashback, Hooker with a Heart of Gold Rosita offers to have sex with Ray, and he accepts. They start a relationship, resulting in the conception of Anna.
• The Dreamers: Matthew having sex with Isabelle turns out to be hers, which surprises him greatly as she'd acted far more experienced.
• Eloïse's Lover: Àsia and Eloïse sleep together the first time after their kiss in the rain. For Àsia at least, it's her first time with a woman (or possibly anyone, since it's left unclear if she slept with Nat).
• Freshman Year: CJ and Marcella were both virgins before having sex.
• Girls Like Magic: Jamie and Maggie impulsively start to have sex toward the end of the film after much obvious sexual tension.
• The Incredibly True Adventure of Two Girls in Love: Evie and Randy have sex toward the end of the film. It's both their first times, which is a surprise for Evie since she'd thought Randy already slept with women before.
• Jennifer's Body: Needy and Chip decide to have sex together the first time. It's tender and sweet, though a bit realistically awkward. Unfortunately it's interrupted since Needy's seeing Jennifer's killing of Colin at the same time while they're having sex, seriously disturbing her, and so she breaks it off.
• Juno: In the first couple minutes of the movie via flashback exposition. Less about love, though, and more about two teens just being bored. In an interview in BUST magazine, Diablo Cody said that it was only Paulie Bleeker's first time but not Juno's. That much is implied in Juno's narration: "I hate it when adults use the term 'sexually active.' What does that even mean? Can I deactivate someday, or is this some sort of permanent state of being? I'm guessing Bleeker went live that night we did it, and that's why he got that look on his face."
• Lady Bird: Lady Bird's first time with her Jerkass boyfriend Kyle is awful and unsatisfying. He doesn't try to guide her, makes no effort to really please her, and ends up climaxing extremely quickly. It's particularly painful because he claimed to be a virgin to get her into bed, and offhandedly admits that he can't even remember how many girls he's been with at this point. Kyle's unapologetic when she voices her dissatisfaction and then outright mocks her for thinking he would try to make her first time special.
  Lady Bird: I just wanted it to be special.
  Kyle: Why? You're going to have so much un-special sex in your life.
  Lady Bird: I was on top! Who the fuck is on top their first time!?
• Listen to Your Heart: Ariana is implied to have sex with Danny when he's in the hospital, and it had been said earlier she's still a virgin in her early twenties due to her mother's overprotectiveness.
• Maggie & Annie: After going to a bar's lesbian night, Maggie and Annie have sex together the first time. Annie hasn't been with a woman before.
• Malavita: Belle seduces her teacher, and loses her virginity through him.
• Margarita with a Straw: Laila initially has sex from Khanum, in what's clearly her first time with anyone. In a second example, she has sex with Jared as her first time with a man.
• My Animal: Heather goes back to Jonny's place with her after the Dance of Romance they have, with the two having sex at length. After this however Jonny tells her to go then stops seeing or talking with her, so Heather is left bewildered and hurt.
• Plan B: Sunny loses her virginity while drunk with Kyle, after her real crush Hunter drove off with another girl. It's a huge let down.
• The Pretty One: The film opens on Laurel and a young man having sex. It later turns out she lost her virginity to him, having gotten tired of waiting. Everyone finds it a bit creepy since she once baby sat him as a kid.
• Princess Cyd: About midway through the movie, Cyd has sex with Katie for the first time. It's also probably the first time she's had sex with a girl (or someone AFAB anyway, as Katie's gender isn't clear).
• Red, White & Royal Blue: Alex and Henry's first time having anal sex in Paris is treated as this. While neither of them are virgins and they've already had oral sex at least twice at this point, it's nonetheless a big step in their relationship, especially since it's the first time Alex has been with a man in such a fashion. Henry describing the act as "making love" only emphasizes it. Alex is initially very awkward and nervous due to his inexperience, causing Henry to promise he'll properly guide him through it.
• Show Me Love: Elin loses her virginity through having sex with Johan, whom she dates briefly. He's surprised afterward when she tells him, since Elin has a reputation for promiscuity.
• Subverted in Spanking the Monkey. Raymond and the cute Girl Next Door are making out for the first time, but since they're both too inexperienced and don't really know what they want he's too gentle at first and then too aggressive when she tells him to be more rough with her, so they both stop. This contributes to Raymond's growing sexual frustration and the later sexual encounter he has with his mother.
• Happens in The Spectacular Now, and plenty of cast and directors interviewed about it discuss how they sought to make it more natural and less idealized. A deleted scene reveals, though, that it wasn't Aimee's first time, which was when she was 14 and the guy was 20.
• Stealing Beauty has a scene midway through the film of the younger members of the cast talking about their first times over drinks and weed. They include Miranda having sex with a man she calls "the local deflowerer" for whom women actually lined up, and her current squeeze Ian tripping with his babysitter when he was eleven. Main character Lucy is a virgin and partly visited Tuscany hoping to meet back up with the boy who sent her an unsigned love letter after a previous visit. She nearly has her first time twice (she has a panic attack the first time, with Niccolo, because the setting resembles what her mother wrote in her diary about when Lucy was conceived out of wedlock, and the second time the man is too drunk and passes out on her sofa). Ultimately her secret admirer turns out to be Osvaldo, who admits to having been a virgin himself after they sleep together for the first time.
• Steam (2007): Laurie has sex with Roy, even as Elizabeth does with Niala for the first time. It's shown with intersecting scenes of them all.
• Submarine: One of Oliver's main goals in the first half of the movie is to lose his virginity; eventually he gets his love interest Jordana to lose it with him.
• The Summer of Sangaile: Sangaile and Auste have sex together the first time about halfway into the film.
• In Too Soon to Love, high schoolers Jim and Cathy lose their virginity one night on a deserted beach. Cathy promptly gets pregnant.
• The Truth About Jane: Jane and her girlfriend Taylor clandestinely have sex at Taylor's house (Jane's, not Taylor's, first at least).
• The Wackness: Luke has sex with Stephanie, and it turns out he's a virgin beforehand.
• Waves: Emily and Luke have theirs together. He comes fast, but Emily says it's fine-they can do it again.
• When Time Got Louder: After Abbie and Karly's first date on the beach, they go back to Abbie's dorm room and have sex on her bed.
• Women Is Losers: At his urging, Celina has sex with Mateo on the roof after agreeing that she wants her first time with him.
• In Youngblood (1986), Dean and Jessie have sex in Dean's room, after moving his mattress to the floor so the springs won't creak.
• Young Hearts: Harper and Tilly decide to have sex together, the first time for both. They both make sure the other is ready, fully consenting and get protection beforehand.

Jokes

• A teenage guy comes to his dad and confesses that he had intercourse for the first time. Dad says: "We need to talk, sit down for a while." The son replies: "I can't. My butthole still hurts like hell."
• A young groom-to-be was nervous and didn't know what to do on his wedding night. His best man told him he would rent the hotel room next door, and if he had any trouble to holler through the wall. Finally the big night came, but as the groom was taking a shower the new bride realized she really had to use the toilet herself. She was too shy to go into the bathroom with him in there, and realized she wasn't going to make it to the public restroom in the lobby. At a total loss, she used the shoebox her bridal shoes had come in and stuck it under the bed. Finally the groom came out of the restroom and walked over to the bed - but stepped right in the shoebox. He looked down and exclaimed "This box is full of shit" And a voice from the next room over yelled back "FLIP HER OVER!"
• A Dumb Blonde was getting married, but was confused about the wedding night. Her mother tried to put what to do delicately. "Take what he loves the most and put it where you go to the bathroom." The wedding night the blonde called her mother in tears - the new husband had stormed out when she put his bowling ball in the toilet.

Literature

• In Alexis Carew: The Little Ships, Alexis infiltrates Hanoverese space to make contact with the Berry March fleet and talk them into rebellion. She finally makes contact with Delaine Thiebaud, a Berry March naval lieutenant she fell in love with while a prisoner of war in the previous book, and sleeps with him for the first time after explaining the situation.
• All-American Girl (Meg Cabot): The sequel Ready Or Not focuses on this. The protagonist Sam Madison is the girlfriend of the First Son and a spokeswoman on teen issues (a role thrust upon her in 'reward' for her saving the President's life in the first book). She worries when her boyfriend implies he wants to have sex and eventually concludes she's ready for it. It turns out he didn't mean to imply that at all but they end up having sex near the end of the book. Mix with this Sam very vocally objecting to the President's plan to limit access to birth control for teens on live television (which accidental implication that she and his son have done 'it' already before the fact) making Sam a big 'ol ball of angst up until they do.
• In Almost Perfect, Sage and Logan spend a weekend visiting Laura at her college. After a wild frat party, Laura goes off with her boyfriend, so Sage and Logan have sex in her dorm room, although Sage keeps her shorts on.
• Anatomy Of A Boyfriend by Daria Snadowsky discusses the main character Dom and her first time with her first boyfriend Wes. Sort of different from most YA books in that everything is described in a more-or-less Ikea Erotica style, and it also addresses more of the awkward things that happen during sex (such as someone possibly farting).
• Arifureta: From Commonplace to World's Strongest: Yue seduces Hajime in the bath while they're recuperating from their ordeals in the Great Orcus Labyrinth in Oscar Orcus's estate at the bottom. They're both virgins, though Yue was trained in sexual arts by her aristocratic family.
• Bazil Broketail: Relkin has sex with Minanswa and loses his virginity by doing so in book two.
• Bridge of Clay
  • Shown with Abby and Matthew. Basically, she was the driving force, invited him to her place and guided him. Which later comes up as one of her complaints when she decides to leave him.
  • And then there is Clay and Carey's first time, fully spontaneous after they've been together for a long time. Tragically, it is also their last time, as the girl dies on the very next morning as an indirect consequence of their love-making.
• The second chapter of Candy by Terry Southern had a chapter dedicated to the title character's first time... it ended with her father being knocked unconscious.
• Ikki and Stella have their first time in volume 9 of Chivalry of a Failed Knight.
• The Chronicles of Dorsa: Tasia and Joslyn finally have sex together the first time in the latter half of the first book after heaps of sexual tension beforehand while taking a bath together.
• In Daystar and Shadow, Robin and Shadow have awkward, unsatisfying sex while hiding above the entrance to the New Christian stronghold. Afterwards, Shadow is distant, which Robin eventually realizes is because he only used his body when she wanted him to use his mind.
• The Empirium Trilogy: Three days before the fire trial, Audric sneaks into Rielle's rooms to discuss his personal fears as to what becoming Sun Queen would mean to them both. The conversation culminates with Rielle and Audric making love on her bed.
• Sayama and Shinjou, the main couple of The Ending Chronicle, have sex in the last volume.
• In Evidence of Things Not Seen, Izzy decides to have sex with her friend Alex, a fellow virgin, so that her virginity won't be a factor in future sex-related decisions. Unfortunately, she assumes that A Man Is Always Eager and doesn't check in with him first, resulting in an accidental sexual assault.
• Forbidden: Lochan and Maya, who have been romantically involved for some time, but have sworn to never have sex, eventually lose their virginity to each other near the end of the book, thinking that the rest of their family will be out of the house for a few days. Unfortunately, their mother walks in on them, and their whole lives fall apart.
• In the Gentleman Bastard series, teenage Locke and Sabetha finally act on their feelings for each other after years of Belligerent Sexual Tension and semi-friendly rivalry, then have a bemused "Was that all?" moment. Their second and subsequent times, however, are much more rewarding.
• The Han Solo Trilogy: It is heavily implied that Bria and Han have sex on the Togorian beach for the first time.
• Harmonic Feedback: When Drea and Justin have sex on his bed, it's her first time ever, and his first time in a serious relationship.
• Subverted in The Hate U Give, between Chris and Starr. After discussing it for much of the novel, including an incident where Chris tried to take a make out session to the next level before Starr was ready, there's a scene towards the end of the second act where it looks like it may finally happen, this time with Starr initiating. However, Chris stops it, pointing out that Starr is suffering some pretty severe PTSD and is in an awful emotional state — i.e., not in a position to make such a big choice or to grant consent. Starr realizes he's right, and the two end up cuddling and falling asleep in his bed instead.
• In The Hearts We Sold, Dee loses her virginity to James, after overcoming her discomfort with intimacy (physical and emotional).
• How a Realist Hero Rebuilt the Kingdom: Souma's advisors start pushing him to consummate with his fiancees in about volume 3, once the Three Duchies' uprising and the war with Amidonia have been won. It takes that long both for Souma to figure out both that he actually likes being King (meaning Altar Diplomacy is now on the table), and to get things in Elfrieden settled enough for him to have time to think about women. He finally makes a Love Confession to Liscia at the end of volume 4, and they have sex for the first time following a tense state visit by the "Saint" of the Lunarian Orthodox Papal State in volume 5.
• Done with so much subtlety in The Hunger Games: Mockingjay that readers are still debating whether or not Katniss and Peeta were having sex or just making out.
• In The Ideal Sponger Life, Zenjirou and Aura consummate their marriage in the first volume.
• Kea's Flight: After Draz figures out how to temporarily turn off some of the surveillance cameras, he and Kea have awkward sex on a picnic blanket in the hydroponics lab.
• The Kingkiller Chronicle: In The Wise Man's Fear, the teenage Kvothe's first time is with the thousand-year-old legendary Fae seductress Felurian, who's infamous as a Sex Goddess that can outright kill or drive insane the men she sleeps with. Kvothe lucks out that due to him being The Bard, she prefers to hear his songs than to actually fornicate him to death, allowing him to trick her by taking advantage of his virginity: He makes a song about her, while deliberately understating her sexual prowess. She's indignant to it, but he explains that since he was a virgin, he has nothing to compare the experience with. So she decides to allow him to leave her glade so he may experience the love of other women, and return to her when he is able to accurately describe her beauty and skill.
• The Last Adventure of Constance Verity: Constance Verity had lost her virginity in the Amazon jungle to a man named Korak the Savage "and it was glorious."
• Last Night at the Telegraph Club: Lily and Kath first have sex together alone in a dark classroom where they had been going to make out.
• Like a Fish Understands a Tree: George and Tracy, who have Down syndrome, finally get to move into an apartment together, despite their families' resistance. George has had no sex education, so Tracy shows him what to do.
• In volume 6 of Mushoku Tensei: Jobless Reincarnation, Rudeus has his first time with Eris. Then, Eris leaves the next morning and only leaves behind a letter that poorly explains she doesn't feel they're right for each other. The trauma of apparently being dumped right after sex causes Rudeus to suffer from erectile dysfunction for three years.
• Of Fire and Stars: Dennaleia and Mare first have sex near the end of the first book, after a long period of mutual attraction, when both have confessed they love the other before.
• The Oleander Sword: Priya and Malini finally have sex after deep, sustained, building desire to.
• In Otherland Renie and !Xabbu joke that they manage to have three "first times" together. First time they get intimate is with virtual bodies in a virtual environment, the second is a short, intense mindlink when they're still connected to the network and the final is normal sex with their real bodies at the end of the series.
• Portrait in Sepia: Aurora and Diego's wedding night is a big disappointment to her. Justified in that Aurora has not received proper instruction about sex, including that sex can be enjoyable for a woman, and Diego is madly in love with Susana, his brother's wife.
• In Post-High School Reality Quest, Buffy has sex with her boyfriend Tristan against the advice of the Text Parser in her head.
• Dealt with in the later books of The Princess Diaries series. Mia and Michael spend a year discussing/planning, and almost do it, before Mia realizes that Michael is not a virgin, and calls the plan off.
• Discussed in volume 4 of Reign of the Seven Spellblades. When she and Oliver give The Talk to their friends, Chela mentions that probably eighty percent of Kimberly Magic Academy Students will have had their first sexual experience within its walls by the time they graduate. Chela herself ends up having to perform some over-the-clothes Intimate Healing on Oliver later in the volume to address the aftereffects of the previous antagonist's Sex Magic.
• The 'First Time' is apparently an important rite of passage on Lothar in Restoree. Harlan is all set to while away a short sea voyage with some sexual dalliance - until he learns Sara is a virgin whereupon he backs off, but promises to go through with it later when they have time to do it properly.
• In The Roosevelt, Emmet and Jeremey move into the titular assisted living facility together, and have sex as soon as their parents are gone.
• Shine Shine Shine: Before Maxon went off to college, Sunny led him to a wooded area, where she showed him how to have sex. Afterwards, she had sex with other men during her early adulthood, but Maxon never had sex again until he and Sunny got married.
• Song at Dawn: Estela is nervous about her wedding night for this reason. When her husband shows no sexual interest in her she goes to a stable hand in frustration and has a traumatic experience.
• Sorry, Bro: Nareh and Erebuni enjoy passionate sex together the first time after the latter has read her fortune. While Nareh mentions being intimate with women before, it's not made clear if that meant full on sex. In any case, she finds this is better than any sex she's ever had with men.
• Stim: While Robert and Chloe are sharing a bed after the earthquake in the first book, Chloe admits her attraction to Robert, and Robert realizes he's attracted to her too. They have clumsy, awkward sex. Robert orgasms but Chloe doesn't, and they decide to research sex to avoid that problem in the future.
• In Sword Art Online, Kirito and Asuna have their first time in the first volume. In the original web-novels, this happened in chapter 16. There was also an infamous chapter detailing the scene in graphic detail... and with hilariously questionable quality. Once the author published the novels officially, that part was removed and a simple Fade to Black was used instead.
• Tell Me How You Really Feel: After going to a bar together, Sana and Rachel go into a back room where they have sex.
• The Testament of Sister New Devil: After six volumes of flirting and foreplay between Basara and his aunt Chisato, he finally takes her virginity during Vol.7. Since Chisato wanted to be dominated, he used his powers to create a doppleganger of himself and ravished her to the point of utter submission.
• Third Time Lucky: And Other Stories of the Most Powerful Wizard in the World: In "The Last Lesson" Magdelene eagerly loses her virginity through having sex with Adar, her master, basically throwing herself on him.
• To Sail Beyond the Sunset: Maureen describes in livid detail how she and her classmate Chuck Perkins lost their virginities to each other.
• Tamora Pierce has written several in her Tortall Universe. Kel had some time to consider it and at least two aborted attempts with Cleon. Daine's was after the series finished. Alanna and Aly both had rather unplanned ones during the series; they hadn't spent much thought considering sex beforehand.
• Trapped on Draconica: Kalak was having a breakdown due to recent events and his Jerkass mask slipped. Princess Daniar comforted him and they ended up having sex. As per the trope, it worked because it was spontaneous.
• In The Twilight Saga: Breaking Dawn, Bella and Edward finally consummate their marriage on their honeymoon, and it results in Bella becoming pregnant.
• In Vampire Academy, Rose got a dose of Squick when she happened to wander into Lissa's mind as she and Christian were about to have theirs. Then in Shadow Kiss, Rose and Dimitri do it in a cabin. The afterglow is promptly overshadowed by a Strigoi attack on the school in which they lose Dimitri.
• Where the Crawdads Sing: Kya has hers with Chase Andrews in a cheap motel during a road trip to Asheville. She finds the experience to be painful and unpleasant, even though she genuinely wanted it.

Live-Action TV

• In Arrow episode "The Fallen", after nearly three years of sexual tension, Oliver and Felicity finally have sex under the surprising suggestion of Ra's Al Ghul. He advises Felicity to have a night of consummation as Oliver is to be assimilated into the League as the new Ra's, with Ra's expressing sorrow he himself was not afforded one last night with his family prior to being taken into the League.
• Played with on 3rd Rock from the Sun: Tommy plans to have his first time with Alissa on Valentine's Day. After finding out that it won't be her first time, he worries that he's not experienced enough. So he has sex with a stranger the day before and then tells her, thinking she will be pleased. She isn't.
• Better Things: It turns out that Frankie lost her virginity with a boy, mostly to see what it's like and wanting this as her choice. Sam isn't too happy (she's only 14).
• Beyond: Holden's first time happens with Charlie in a moment of passion. It's possible he'd already had sex with Willa in the Realm, though he doesn't remember it and it's unclear whether this would "count".
• The "big plot" of Season 9's "The Opening Night Excitation" episode of The Big Bang Theory. Amy's birthday happens to land on the same night the new Star Wars movie comes out, and given they had just gotten back together Sheldon decided that he was ready for intimacy (he has never shown sexual interest in anyone else, and even with Amy he was adverse to actual intercourse). The episode then compares the nervousness and excitement of seeing the Star Wars film with losing your virginity, with the advice to not overhype yourself into expecting it to be the greatest things ever.
• Boy Meets World milks this plot for at least two or three episodes. Cory and Topanga didn't have sex until their wedding night, but there were several episodes about how they were considering sex and almost went all the way.
  • Heck, they didn't even do it on their wedding night, thanks to Eric.
  • This actually saved their lives, albeit in a Dream Sequence, when a murderer ran around the school. Shawn, being Genre Savvy about horror movies, deduced virgins will live, and Cory is then delighted that Topanga saved him. Leading to one of the best exchanges in the whole series.
    Shawn: Virgins. Virgins never die.
    Corey (to Topanga): Hey, thanks for saving me.
    Eric: I'm dead.
    Jack: I'm dead.
    Shawn: I'll get as sick as you possible can without actually dying.
    Corey: Wait a minute, Feeny's dead.
    Eric and Shawn (singing): Go Feeny! Go Feeny! Go Go Go Feeny!
  • Cory had the opportunity a couple of times with girls other than Topanga. Considering what type of show this is, he didn't go through with it.
• Buffy the Vampire Slayer:
  • Willow and Oz are an interesting example, as she's the one who wants to jump his bones, but Oz declines, saying it's just to make Xander jealous, and she's not ready. Then there's a second time when she initiates sexytimes, wanting to make it up to him for an earlier clinch with Xander, but Oz declines again. They do finally make love in the third season finale.
  • For negative aspects, there was Buffy, who unintentionally turned her boyfriend into a soulless murderer by having sex. Let's not forget Xander's almost first time with the bug-lady teacher who wanted to tear his head off post coitus. Or Xander's actual first time with Faith, to whom he meant nothing to and got his feelings hurt. Then she nearly killed him when he came back for seconds. Not to mention Dawn, who never had sex but tried to with a hungry Vampire and a jock who'd accidentally brainwashed her with his jacket. Anya's first time with Xander didn't go as planned either because he was still in her system and he was still acting like a jerk to her.
  • Dawn has her own horrible first time in the Season 8 comic-book continuation, though in that case it was mostly her fault. Dawn had a gentle boyfriend called Kenny, but she actually lost her virginity by cheating on him with his roommate! It turned out Kenny was a pretty potent thricewise demon (a fact Dawn knew about!) and he cursed her with a spell that made her transform into a giant, a centaur and a doll. She apologized to Kenny afterward, ending the spell. They then parted ways on good terms.
  • A variation appears in the Season 8 comics after Buffy sleeps with Satsu (not her first time, but her first time with another woman) — she starts babbling nervously and asking Satsu if she was doing it wrong because of her unfamiliarity with lesbian sex.
• Camelot: Arthur and Guinevere have sex on a beach, echoing a recurring dream he had of this before they'd even met. She's very worried afterward that her soon-to-be husband will know she's no longer a virgin though.
• Control Z: Sofia impulsively throws herself at Raúl after becoming close with him, and they have sex. It's possibly her first time overall.
• Conversations with Friends: Frances having sex with Nick was her very first time with a man, as she admits after they've done it. He doesn't mind.
• Cursed (2020): In "Poisons" Arthur and Nimue have sex after much obvious mutual attraction. She explicitly says it was her first, while saying it's different than she expected, but enjoyable.
• Dance Academy:
  • Abigail and Sammy want to have sex, until Sammy decides that he isn't ready.
  • In season 3, Tara and Ben decide to do it but their plan is halted when the cleaning lady walks in on them.
• Dark Desire: Zoe has sex with Darío on a blanket while out for a picnic, and it's explicitly her first time with a man. Later she also has sex with her friend Karina too. Karina is the first girl she's been with.
• Deadly Class: Marcus sleeps with Maria and loses his virginity after a long period of unresolved sexual tension.
• Dexter: New Blood: Harrison and Audrey sleep together after significant sexual tension in "Too Many Tuna Sandwiches". Angela gets very upset when she finds them in Audrey's bed together the next morning.
• Dickinson: Sue and Emily had sex for the first time in "I Have Never Seen Volcanoes".
• Dracula (2013):
  • Jonathan and Mina consummate their relationship in the sixth episode, pre-marriage vows. Since it was a spur of the moment decision, it goes smoothly.
  • Lucy later seduces Jonathan and loses her virginity by having sex with him to get at Mina for previously rejecting her.
  • Dracula and Mina finally have sex in the series finale, after much obvious sexual tension.
• Everything Now: Mia loses her virginity with Alison in between Episodes 4 and 5. She doesn't really feel any different afterward, and Mia's somewhat surprised by that.
• Everwood:
  • Ephram (in his late teens) dates Madison (in her early twenties). When they try to have sex for the first time, Ephram is too aroused and... finishes early. They were making out when she reached over his head to get some condoms. This reaching pushed her boobs into his face, and she kept wiggling on top of him to get to the condoms. They were quickly unnecessary. Ephram is embarrassed beyond words and extremely upset, and quite realistically, unable to talk about it with anybody. It is implied the next try was successful.
  • Amy is very insecure about her first time ever with Ephram whom she imagines is very experienced from his relationship with Madison. Her cool grandma assures her it is new and strange every time you have a new partner.
• Farscape: In one episode Crichton and D'Argo have to prove they aren't possessed by an energy being so they share personal details such as when they lost their virginities. Crichton claims he lost his when he was 16 to a girl named Karen Shaw, but a later episode reveals that "Karen" was actually a time-travelling Chiana. Young John assumed that her grey skin was part of a Halloween costume.
• Felicity's title character played out this trope with David, her boyfriend at the time, complete with spontaneous reversal.
• First Kill: In the first episode Cal and Juliette lose their virginities together (or Juliette does at least-Cal had a girlfriend before).
• Friday Night Lights had the episode "I Think We Should Have Sex", a Title Drop that briefly summarized the mindset of Julie Taylor. It's widely regarded by fans as one of the best episodes of the first season.
• Lucky Spencer and Elizabeth in General Hospital.
  • For that matter, can we mention how long it took Dillon Quartermaine and Georgie Jones to finally manage to have sex?
    • And among their many issues was that during that interim, he lost his virginity to Sage Alcazar, who was a virgin herself until they slept together.
  • Also done with Jason Quartermaine and Keesha Ward. After she confessed that Their First Time would be her first time, he admitted that it was his first time too, prompting her to wonder how they would know what to do.
  • Stone and Robin, though the only obstacle was simply that she wasn't ready. He respected her decision to wait, and after nearly a year of dating, she was.
• Gilmore Girls has had a few examples:
  • Rory and Dean's first time had no discussion at all (any talk would have probably stopped it, him being married and all) so of course they just did it. After putting it off until marriage (a value Lane didn't even know she had), Lane and Zack's first time was well-planned, long coming and supposedly really romantic. So of course on par with the trope it was horrible — illness, wetness, dirt and discomfort were all present and she got pregnant with twins.
  • Paris, who lost hers off screen and then talked to Rory about it...and then believed it was the reason she didn't get into Harvard.
• Ginny and Georgia:
  • Ginny early on has sex with Marcus as her first time, and loses her virginity this way. It later turns out he'd also been a virgin at the time, to Ginny's surprise.
  • Later, Max's first is with Sophie.
• Glee:
  • This was a subplot of the first season episode "The Power of Madonna", in which three couples (Emma and Will, Rachel and Jesse, and Finn and Santana) attempt to get it on. Emma and Rachel balk at the last minute, but Finn goes through with it. He then instantly regrets it, because it was totally meaningless and he's really in love with Rachel. (That Santana hates him and is a closeted lesbian can't have made the experience any more enjoyable.)
  • In the third season episode "The First Time", Artie, who is directing the high school production of West Side Story, tells Rachel and Blaine that they're too virginal to play Maria and Tony to his satisfaction. This kicks off a plot full of Aesops about having sex for the right reasons and waiting for the right moment with the right person, and the episode ends with scenes of Rachel and Blaine having (clearly very happy) first-time sex with their respective boyfriends, Finn and Kurt.
• Good Omens (2019): Anathema and Newt in Episode 4. He'd never had sex because he's hopeless with women, while she'd been instructed to stay a virgin until then by Agnes' prophecies.
• Gossip Girl:
  • A twisted example on the first season Blair and Nate have been together for a long time, but Blair wants to put off losing their virginity. Nate, however, has already lost his - to Blair's best friend, Serena, an act that partly causes Serena to leave town in shame. Blair seems to have a feeling that Nate likes Serena, because the instant she learns Serena has returned, she drags Nate upstairs from a party for Their First Time - which gets interrupted by Serena's arrival. Soon afterward, Blair plans Their First Time again, only for Nate to choose that moment to tell her about cheating on her with Serena. This leads to more discord between them and they eventually just break up, and in a matter of hours later, Blair loses her virginity to Nate's best friend Chuck in the back of a moving limo. But wait! A few episodes later, Blair and Nate are back together and they actually do have sex. However, when Nate finds out how Blair's First Time actually did happen, he breaks up with her for good. Phew!
  • This was also done with Jenny in season 3. Jenny's first time was going to be with drug dealer Damien. Then she had The Talk with Serena and watched Dirty Dancing. When Damien is about to sleep with Jenny, she asks him how he really feels about her. He is unable to give her a straight answer, so she decides losing her virginity to him wouldn't be right (though for some reason, she feels she has to lie and tell everyone they really did sleep together). What happens in the season finale? Her real first time ends up being with Chuck, whom she means nothing to at all. It is this very action that results in Jenny being Put on a Bus.
• Hanna: Hanna has her first time with Anton, a boy she meets through Sophie. However, this then leads to a rift as Sophie also likes him.
• House of the Dragon: Rhaenyra nearly has sex with Daemon after he takes her to a brothel in King's Landing, but he pulls out and leaves at the last possible second. She eventually loses her virginity later that night to Ser Criston.
• The How I Met Your Mother episode "First Time in New York" revolves around the gang reminiscing about their first times as Robin tries to convince her little sister not to lose her virginity casually. They range from horrible (when Ted confessed to his high school girlfriend that he was in love with her, she lied that she loved him too and then casually abandoned him immediately after he put out) to sweet (when they were college freshmen, Marshall and Lily lying in bed planning a gloriously romantic first time wound up with them having hurried sex in the heat of the moment) to awkward (Robin's boyfriend barely entered her before rolling over and telling her "Yeah, I'm gay.") to humiliating (Barney lost his virginity at the age of 23 to his mother's 40-year-old friend).
• I Am Not Okay With This: Sydney and Stan at the end of episode two. Stan falls in love with her because of it; Syd, on the other hand, simply regards it as a one-time thing. Despite this, they still end up being close friends. It was doomed, given Syd's realized she's a lesbian, describing having sex with him as "really awkward".
• Impulse: Jenna and Zach lose their virginities together. Jenna's also attempting to be straight through having sex with him.
• In From the Cold: Anya and Faina have sex in "Little Bird" after much obvious sexual tension.
• Interview with the Vampire (2022): In "In Throes of Increasing Wonder...", after wooing Louis de Pointe du Lac for a few months under the guise of friendship, Lestat de Lioncourt invites his Love Interest to enter his home and join him for a nightcap, and they engage in passionate lovemaking soon after. During their post-coital bliss, they share a Held Gaze that silently communicates their love for each other.
• Jane the Virgin: Jane's first time having sex was in "Chapter Forty-Seven". The Unspoken Plan Guarantee element is both played straight and deconstructed: their plans are derailed by constant interruptions, and it's only when they are able to be spontaneous that they succeed in consummating their marriage. The deconstruction happens when they fail at Idealized Sex, and Jane isn't particularly satisfied. Ultimately, good sex requires both spontaneity and planning.
• Subversion (even if it might predate the trope's existence as a trope): Lance Kerwin and Melissa Sue Anderson's sleeping bag liaison in James At 15.
• Shows up in Lie to Me. Lightman's worried that his daughter Emily is about to have sex with her new boyfriend, when he catches them making out. He obsesses over it for most of the episode, until they finally sit down and have a talk about the issue. Turns out, Emily broke up with the guy without sleeping with him. But she's already lost her virginity months ago to someone else.
• Lois & Clark: The episode Soul Mates (right after the wedding one) revolve around this. Justified as Lois and Clark had to explore time and anterior lives to lift a curse, then properly having their first time.
• Lovecraft Country:
  • Leti lost her virginity to Atticus while at a party with him.
  • It turns out that Atticus' first time was with Ji-Ah, a woman he met in South Korea.
• Manhattan Love Story: Dana and Peter lament how something always comes up and interrupts them or ruins their night before they actually do the act. They finally manage to after many hurdles.
• Motherland: Fort Salem: Tally loses her virginity through hooking up with Garit during the Beltane festival. She's ecstatic about it later.
• My Left Nut: Because he thinks he's going to die, Mick tries to rush his relationship with Rachael because he doesn't want to die a virgin. But this ends up getting Averted since by rushing things, he ends up screwing it up alienating Rachael just as they're about to have sex. But by the end, he also ends up not having cancer and patches things up with her and they have a Relationship Upgrade, but now taking the relationship slow since he no longer has to worry about dying.
• The New Girl episode "Virgins" has the group reminiscing about their first time. All the stories were incredibly awkward and cringe inducing, except for Cece, who lost her virginity to Mick Jagger.
• Averted in NewsRadio when Jimmy is telling Dave about a chance reunion with an old flame. Jimmy thinks Dave is referring to this trope. Dave clarifies and wishes he hadn't.
  Dave Nelson: Was it the first time?
  Jimmy James: No, I've had sex before, Dave.
  Dave Nelson: I mean was it the first time with her?
  Jimmy James: Oh. Yes, it was. We started out kinda slow...
  Dave Nelson: Um, could you hold that thought...forever?
• Seth and Summer on The O.C.. In fact, their first two times were awkward, for very different reasons.
• One of Us is Lying: Nate and Bronwyn have sex finally in Season 2 after confessing their love for each other.
• Outlander: Brianna and Roger, after handfasting (an old Scottish custom in which a couple get temporarily married outside formal proceedings), tenderly have sex in a closed up shop (it's also her first time, period, as she is a virgin before this). Unfortunately, they have a fight afterward, which causes Brianna to leave.
• The Outpost: Janzo, who's established as a virgin earlier, loses his virginity with Wren and they later become a couple.
• The Republic of Sarah: Bella and Tyler arrange to have their first time together, but at first it doesn't work out as a result of the pressure. However, later they have sex-multiple times, in fact.
• Roseanne:
  • The show subverted this well in the episode where Becky timidly appealed to her mom for help getting birth control pills. It is revealed that not only did she already lose her virginity to biker boyfriend Mark entirely offscreen, but they had been having sex for quite some time and simply wished to stop using condoms.
  • Darlene's was more typical. After putting off her otherwise nice but pressuring-for-sex boyfriend, the first time she finally proposed Their First Time, he 'failed to perform', and took the whole episode to get over his self-imposed pressure.
• Will and Emma's first time in Scream: The TV Series happens prior to the show, but is used as a plot point - not only did Will only do it because he'd been dared he couldn't get Emma to put out, but it was also filmed for proof he'd succeeded, and later accidentally e-mailed to everyone in the school.
• Siren (2018): Ryn, Maddie and Ryn have sex together finally in "Leverage". Before this happened they had accepted Ryn's offer of making love with them, but hadn't gotten around to it.
• In Smallville, Clark finally has his first time with Lana in a Season 5 episode where he lost his powers, only to be chewed out by his parents when they find out. He calls them on it.
• Special Ops: Lioness: Cruz and Aaliyah have sex after they establish a mutual attraction for each other.
• That '70s Show:
  • The show had several early episodes that centered, partially or fully, on Eric and Donna preparing to sleep together, and then backing out at the last minute. They're finally able to do the deed about midway through the second season (one episode ends with them about to do it, and the next episode begins with them already finished). More realistically than most TV "first times", it didn't go all that well, leading to angst the morning after. This leads Eric to the very logical conclusion that what they need is "Practice, and lots of it!"
    Hyde: If God had intended for virgins to lose it to each other, he wouldn't have invented middle-aged hookers, man!
  • Fez's attempts to lose his virginity are pretty much a Running Gag, and his friends constantly tease him for it. He finally loses it off-screen in the fifth season to his older co-worker Nina. It was... aaaaaaawkward.
    Fez: Well, our faces didn't line up right, so I kept bumping my chin on her nose. And then there were some sounds.
    Hyde: What kind of sounds?
    Fez: Well, I will say this, it was not applause. There was no romantic music like in the movies, so I had to hum. And then Nina told me to stop humming. And, uh, then I started again without realizing it. And then she got mad. And then I think she got sad. (...) And then afterwards, I went into the bathroom, and, uh... And cried a little. And then I snuck out the back door.
    Donna: Poor Fez. Well, you know, at least it couldn't have been any worse.
    Fez: I left my underwear in her bathroom.
• True Blood:
  • In season two, Hoyt and Jessica lose their virginity to each other. Then later, they later found out that vampires who die with their hymen intact will continue to regrow it and so had to find alternative ways to express their love. This is probably a good demonstration of why the realistic, loving relationship between the two characters saved Jessica from the Scrappy heap.
  • Sookie loses her virginity to Bill in season one. It's a positive experience for her, especially so after she reveals that she was molested as a child by an uncle.
    Sookie: I never thought I'd be able to...
    Bill: I am honoured that you chose me.
• What I Like About You has a different spin on this for every single character. The most prominent versions were the straight-play with Holly & Vince in "Halloween" (an episode full of angst from both, followed by the "30-seconds-later" thing) and the subversion with Val & Vic throughout season 4 (they probably did it on their drunken wedding night, but Val doesn't remember; either way, they don't go again until after their "formal" wedding in the finale, by which time both are more than ready).
• The Wilds:
  • Shelby and Toni resolve their sexual tension offscreen by having sex (which is at least Shelby's first).
  • Her flashback has Nora and her boyfriend Quinn decide to lose their virginities together.
• Yellowjackets:
  • Jackie convinces Travis to have sex with her as she doesn't want to die a virgin.
  • Apparently the case for Taissa and Van, who get it on out in the woods, although they might have earlier.
• Zero (2021): Omar and Anna have sex, which is at least his first (not hers).

Music

• The All-American Rejects' "Dance Inside" is a good example of this.
• Sparks' "Amateur Hour" is about how the first time will always suck because of inexperience.
• "De Eerste X" ("The First Time") by Dutch band Doe Maar in which someone is deflowered by a woman, but feels he can't live up to her expectations. Then he leaves her, but feels regret afterwards.
• The Zenryoku Shounentachi no Toriai song "First Experience" recounts a tale of this from the woman's point of view, and also addresses how awkward it can be while trying to play it up for all the sexiness it can muster.
• Meat Loaf's "Paradise by the Dashboard Light" from Bat Out of Hell is about a high school couple, "barely seventeen" making out in a car, then having sex when the boy swears he loves the girl and will marry her. He grows to hate her over the years.
• "Christians in Love" by comedy band Dead Cat Bounce details the first intimate exchange between a newly-wedded Christian couple, playing up both of their inexperience with crass imagery. It turns out that the band themselves are actually watching it happen from outside the couple's hotel room, and are demanding their payment for having performed at the wedding.
  Like a shithouse door in a force-9 gale
  They're banging hard 'til their hinges fail
  With no real discernible sense of rhythm
  Like Keanu Reeves in the movie Speed
  They're scared that slowing down might lead
  To some sort of explosive cataclysm
  Taking Dennis Hopper with them
• "December, 1963 (Oh, What a Night)" by Frankie Valli and the Four Seasons is about a man fondly remembering his first time having sex with a women way back in "December, 1963".
  Oh, what a night
  Late December back in sixty three
  What a very special time for me
  As I remember, what a night
  Oh, what a night, you know I didn't even know her name
  But I was never gonna be the same
  What a lady, what a night
• "Will You Love Me Tomorrow?" by The Shirelles deals with a woman's concern about whether her boyfriend will still love her the day after giving up her virginity to him.
  Tonight you're mine completely
  You give your love so sweetly...
  ...Is this a lasting treasure
  Or just a moment's pleasure?
  Can I believe the magic of your sighs?
  Will you still love me tomorrow?
• "Night Moves" by Bob Seger is about a guys "first time" in the back of his car with his girlfriend.
  Out in the back seat of my '60 Chevy
  Workin' on mysteries without any clues
• Mystery Dance” by Elvis Costello is also deals with a mans very awkward first time using the euphemism "Mystery Dance" to refer to first time sex.
  Well, I remember when the lights went out
  And I was tryin' to make it look like it was never in doubt
  She thought that I knew, and I thought that she knew
  So both of us were willing, but we didn't know how to do it

Theatre

• Tacked on as almost an afterthought for a quick joke in Heathers. After singing one of the best songs in the show about having sex with J.D., Veronica caps off the next scene with this.
  Veronica: Oh, and, uh... by the way... (awkwardly pats J.D.'s shoulder, clicks her tongue) ...You were my first. (walks away, leaving a bewildered-but-flattered J.D.)
• The second act of Jasper in Deadland opens with a flashback of Jasper and Agnes talking about their feelings for each other before having sex for the first time.

Visual Novels

• Being A ΔΙΚ has this show up quite significantly for the MC and all Main Girls, along with some others.
  • As discussed with Isabella in the flashback in "100%", the MC lost his virginity to his best friend Zoey in high school while fooling around with her; though they remained Friends with Benefits for a long time, both of them seem to have realized their deeper feelings for each other by the time she left for San Diego. Things do not get any simpler when she comes back, having realised her feelings for him...at the end of Episode 8, by which point the MC may have committed to a Main Girl relationship.
  • Josy's first time with the MC happens in "Maggot Brothers" if he stays at her place, and is interrupted by Pete and Monica returning home, leading to him having to escape through the window.
  • Maya's first time with the MC in "The Initiation" is interrupted when it turns out to be a prank by Quinn, with the former grinding on him (and starting to get into it) before he is tased by the latter. Their actual first time in "100%" is also somewhat sensitive, given that it is Maya's first time with a man.
  • While Isabella does sometimes engage in sexual activity with the MC throughout Seasons 1 and 2, they do not go all the way till he commits to her in Episode 8, which is also the first time she is having sex with anyone since James. Notably, it is played as being extremely cathartic for Bella as a sign of her starting to move on from James.
  • Especially notable for Jill, who starts the game as a virgin and whose tendency to believe that her life is like a romance novel means she attaches a great deal of importance to her first time; the arc words for her path, aimed at the MC, are "Are you my destiny?". Unsurprisingly, she does not engage in sexual activity unless the MC commits to her in Episode 8 by confessing his feelings for her at her third date with Tybalt (and kissing her in front of him), after which she loses her virginity to him in his room and affirms that they are now together.
• Shown with all the girls in Daughter for Dessert in a similar way, in which the protagonist seduces each one with a different masculine quality.
• Has a different character with each girl in Double Homework:
  • One of the rules of the protagonist’s, Johanna’s, and Tamara’s ménage a trois is that when two of them do anything sexual together, they need to tell the third person. The two girls also let the protagonist choose which one he wants to bed first. He chooses one of the two after Dennis starts blackmailing Dr. Mosely, fearing that he may not get another chance. He does, and sleeps with the other one soon afterward.
  • Lauren passes the protagonist a note in class telling him a plan to get out of class, and then asks him if he would consider them to be "dating." She seduces him if he says he does.
  • When the moment hits between the protagonist and Morgan, Morgan says that they should get straight to the point, since "we're both fairly experienced."
  • Amy seeks out sex with the protagonist on the yacht, and allows him to do whatever he wants when he finds her in the hot tub.
• Fate Series:
  • Happens in each route of the original Fate/stay night, but it's most prominent in the Unlimited Blades Works route, where Shirou's and Rin's first time is Played for Laughs due to the awkwardness of the whole situation... and it works, because Rin is tsundere even in bed. She actually refuses to take off her shirt at first, and Shirou eventually has to make her compromise with stockings. Not helped by the fact that Shirou's... size makes Rin even more nervous. In fact, this is a rare case of, after the act, the girl bitching the guy out because she didn't like it. So much for the afterglow...
  • Shirou and Rin do have a much better time having sex together in Fate/hollow ataraxia, where they don't have the pressure of a Mate or Die scenario looming over their heads and they've become comfortable enough with each other for Rin to let out more of her "dere" side.
• Happens in each route of Katawa Shoujo:
  • The most glaring example comes in Hanako's route, where not only are neither she nor Hisao emotionally prepared, but despite Hisao's tries, Hanako is very much in pain. (Not helped by how the body tissue from her scars severely limits her flexibility).
  • Goes more smoothly in Lilly's route, where Hisao notices some drops of blood when he penetrates Lilly and gets nervous — but she tells him it's okay, and their sex scene is relatively pleasant aside of this.
• This is the basic premise of Kindred Spirits on the Roof: Sachi and Megumi are ghosts and are very much in love with each other. They wish to take it to the next step before passing on to the afterlife but they don't know how. So they rope Yuna, the only person who can interact with them, into a plan: Find possible girl-girl couples in the school, help them get together and hope that the ghosts will learn from their experiences.
• In Melody, this takes on a different flavor with each of the various girls that the protagonist can be involved with:
  • Melody: The two of them get off to several false starts due to Melody's virginity being on her mind, or just being in public when the "right moment" comes. However, it eventually hits when they're in the bedroom together.
  • Isabella (her path only): Isabella starts coming on to the protagonist as soon as they see each other, but they can’t do anything yet due to Tim being there. At night, after Tim is drunk and (supposedly) asleep, they pick up where they left off.
  • Becca (her path only): Becca holds off with the protagonist, not wanting to appear easy. She reaches the point where she wants it, but stops the protagonist because he doesn’t have a condom on hand. Soon after, he gets a condom, and they go all the way.
  • Amy (her path only): Amy tries to seduce the protagonist in her hotel room, but he resists for Melody’s sake. However, when she invites him in for the second time less than a week later, they fool around, but Amy passes out from alcohol before they consummate their relationship. Soon after, however, they have sex.
  • Sophia (her path only): The protagonist and Sophia know pretty early that they’ll be having sex, and they do on their first meeting alone after Sophia offers him a “discreet” relationship.
• Happens in both the main story and after story routes in Princess Evangile, when Masaya and his respective love interest of that route decide to consummate their relationship, depending on the situation and circumstances. Notably, in the main story routes, these usually happen before the Big Bad enacts an Evil Plan on either Masaya or his Love Interest, while in the after story routes, it's simply there for a combination of fanservice and the fact that Masaya and his Love Interest are finally comfortable with one another.
• The good ending of Sable's Grimoire: Man and Elf has Sable and Lisha consummate their new relationship.
• Sex Advice Succubus: Chloe contacts Qmin, the titular succubus, for advice because she will be visiting with her online girlfriend for the first time, and worries if it's even possible for them to have sex (because Chloe is a ghost). In one of the endings, Qmin encourages Chloe to stop worrying so much and just deal with it as it comes, because even though the first time is probably going to be awkward as hell, figuring it out together is what makes it fun.
• In Sunrider, flashbacks show that Kayto Shields and Ava Crescentia had their first time back in high school, days before Ava’s graduation. It was very much a spur-of-the-moment thing, as Ava was leaving for the military right after graduation and the two of them had just admitted their feelings for one another earlier that evening.

Webcomics

• In Doc Rat, Ben and Daniella's first time together is something the lead-up to was particularly dramatic. Both were already experienced,^note In fact, both already had produced offspring; though Ben's previous daughter was born after his first wife left him and moved to America, and Daniella's first clutch of children were eaten by a predator. but Ben's insistence on waiting for the right time gave Daniella the false impression that their relationship was souring. Once they got engaged, they finally had sex after a dinner date at Ben's house. The premonition is a Sexy Silhouette of Danni leaning forward on the dinner table, looking like she's about to jump Ben over it.
  Ben: Did you bring dessert?
  Daniella: Did I ever.
• Due to taking place during college, a number of characters and couples have sex with each other for the first time in Dumbing of Age and shown in the Slipshine comics.
• Seen in flashback in Everyday Heroes: Marko (Mr. Mighty), reveals to Jane the Heroes' most-guarded secret - the existence of the power-suppressing drug Nylvarrine - and even gives her a sample as a sign of trust. He's then moved to go all in and propose to her. Jane (who had some serious trust issues from her time as a villain) reacts by popping the Nylvarrine pill into Marko's mouth and taking her top off.^note By Jane's own admission, as she relates (most of) this to their daughter Summer, they hadn't even kissed up to this point
  Jane: That was "yes", by the way.
• Evon: Evon and Hero finally consummate their relationship between comics 1011 and 1015, after some prodding of Evon by her clone/sister Evee, who plays matchmaker despite loving Hero almost as much as Evon.
• Kevin & Kell's premonition for the first time for Rudy and Fiona, after a quarter century of Comic-Book Time (roughly a decade real-time) of dating? Fiona telling Rudy that dishes from a special dinner can wait until morning. That next morning, Rudy wakes up in bed with her. But they agree that marriage can still wait a bit longer.
• Kill Six Billion Demons opens with the protagonist Allison preparing to lose her virginity with her boyfriend Zaid, having scheduled the date and time with him beforehand. Allison is reluctant, Zaid is being pushy, and everything goes to (a) hell before they can actually do it. Allison’s actual first time is never shown, as the next time her sex life comes up is after a Time Skip, during which she started dating Cute Monster Girl Cio and picked up plenty of experience (especially regarding no longer being so awkward she needs to schedule when she’ll have sex).
• Comics in the Ménage à 3 universe play first times all sorts of ways, sometimes averting the trope and sometimes not — mostly, it seems, because they're Sex Comedies and will do whatever gets a laugh.
  • In the original comic, the sex between Gary and Kiley is the first time for him, though not for her, and is realistic enough to avert the trope, in that he suffers Premature Ejaculation. (Then things get less realistic.)
  • In Pixie Trix Comix, the first-time sex between Julian and the virgin (and previously not-consciously-bisexual) Aaron fits the classic trope pattern, being spontaneous to the point of rashness and yet apparently very satisfying for both parties.
  • Sandra on the Rocks is all over the place on this subject; the attempt at first-time sex between Marie and Ingrid is abortive, mostly because Marie realizes that she's entirely straight, while Alex's first time is just plain confused, thank to the dubious machinations of Eloise and Nadine.
  • Sticky Dilly Buns, however, ruthlessly averts the conventional TV view of unprepared sex being good sex, twice. (It may be relevant that the couples involved aren't naive teens.)
    • The first time between Jung and Ramona takes place off-screen, but it's very clear that Jung's scrupulous preparation makes the sex about as good as it can get for Ramona (and probably for him too).
    • When Ruby thinks that Andy is proposing sex, she is initially nervous, but talking to friends calms her nerves. The fact that actually getting to the sex itself turns out to be more complicated than expected is just one of those things, but when it happens, Ruby turns out to be mentally and physically ready, and enjoys it.
• This plays out in Sunstone when Ally and Lisa finally meet, but subverted as they've both had sex before; it's their first time trying out BDSM with each other and naturally they are quite nervous about it.
• Tripping Over You: Milo and Liam consummate their relationship in Chapter 5, with only a short break to consult the Internet for advice when they realize neither of them has sexual experience with another man. They're pleased enough with the results.

Web Original

• Literotica has an entire section titled "First Time," which is about exactly this.
  • Playing with the trope, however, stories in this section don't necessarily have to be about the characters losing their virginities - more that it needs to be the first time for that particular couple.
• One of the first internet hoaxes was supposed to be a live deflowering at a site called Our First Time. It followed two "teen virgins," Mike and Diane, as they chose condoms, informed their parents, and got tested for HIV, with their actual first time broadcast live in August 1998. However, when people started to notice that the two didn't look like teenagers, the entire plan was revealed as a hoax, and the guy behind the whole thing said that he intended Mike and Diane to abstain at the last minute (after charging a $5 viewing fee, intending to use the money to fund a Vanity Project named "Heart of the Beholder" in which the two actors would get the starring roles.) Strangely, it seemed like nobody at the time noticed that "Diane" had been a cast member on Road Rules the previous year under her real name, Michelle. Details.

Western Animation

• Big Mouth: When Val and Leah sleep together for the first time in "Sugarbush", he's quick and clumsy. When they're done, Val collapses next to her and claims it was amazing while a clearly unsatisfied Leah hesitantly lies to assuage his ego. Bonnie sums it up with "It was pokey and fast and chaos. He promised you a happy cry, but left you feeling crappy and dry." They do it better the second time, when Leah becomes more comfortable telling him about what she likes.
• Parodied in Bob's Burgers except it's about eating lobster.
  "When you get married, just pretend you've never eaten lobster before."
• After Tom falls asleep at Daria's house (during a perfectly innocent study session) and gets caught sneaking out the door at four in the morning, a rumour begins going around that the two had sex. Daria begins to wonder if maybe it says something about their relationship that they're not sleeping together and tells Tom she wants to start. She changes her mind after they've agreed and, worried that Tom will think she doesn't really like him much after all, writes him a breakup note. He forgives her and life goes on.
• In the Harvey Birdman, Attorney at Law episode "Peanut Puberty", which plays the Puberty Superpower trope for parody, Peanut at one point asks Black Vulcan about his first time...fighting a supervillain. Apparently both he and the villain were nervous about it, exchanged small talk first, and then had a cigarette afterward. Peanut would later come into Harvey's office and introduce his 'villain friend', implying that he had his first time.
• An episode of Pepper Ann mirrors this plot, except that the first time in question is a First Kiss.

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