Related to Will They or Won't They?, Their First Time is when a teen 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.)
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.
- 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."
- Mobile Suit Gundam SEED: Poor, poor Kira Yamato. His first time was an attempt to seduce him into exterminating the rest of his entire race. What can you expect when Jesus has sex?
- Pretty much the whole chapter 52 of Future Diary is dedicated to this, 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.
- A minor subplot in Futari Ecchi has Makoto Kawada's teenage sister Jun and her sexual self-discovery, which of course includes this. And 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.
- It's strongly hinted in Shaman King that Anna Kyouyama and Yoh Asakura went through this 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.
- In Girl Friends, 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.
- 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 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.
- In Sword Art Online, Kirito and Asuna have theirs at the end of episode 10. 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.
- 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.
- Happens in Rurouni Kenshin, between Kenshin and his First Love Tomoe. As a bonus, it takes place when it's snowing.
- Chapters 137 to 139 of Ai Yori Aoshi are dedicated to Aoi and Kaoru finally being able to have theirs, after they're able to say "screw you" to their families and stay together.
- 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.
- 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.
- Tokyo Ghoul:re: The whole chapter 125 is dedicated to Touka and Kaneki's first time.
- Uchi no Musume ni Te o Dasu na!: Subverted between Clara and Mei. 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.
- Hori and Miyamura in Horimiya have their fist 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 look for (the undo button) too—[Kaoru punches him in the back of the head].
- 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.
- In the manga Risou No Himo Seikatsu, Zenjirou and Aura had their first time & wore their wedding rings in chapter 4.
- DARLING in the FRANXX: Surprisingly it's the Beta Couple of Mitsuru and Kokoro who end up in bed together first, not 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 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.
- Domestic Girlfriend: The very first page 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).
- Kaguya-sama: Love Is War: It's all but stated that Kashiwagi and Tsubasa slept together for the first time during summer break.
- The Sin City series begins with the main character losing his virginity to a beautiful young woman. And 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...
- 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.
- 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.
- Spider-Man: The first openly sexual relationship Peter had with any of his girlfriends was with Mary Jane Watson and the end of Issue 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).
- As Fate Would Have It: Following their Relationship Upgrade and several subverted attempts, Nate and Yancy finally do it for real in Chapter 13.
- Axis Powers Hetalia 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.
"The Axis Virgin Trio is no more!"
- 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.
- 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.
- 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.
- 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.
- 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.
- Ghosts of Evangelion: Shinji and Asuka have sex for first time during a vacation trip, six years after their first meeting. They hadn't been emotionally or psychologically ready until then.
- 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.
- 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.
- 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.
- 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.
- Thousand Shinji: Although they had gotten together and made out many times Shinji had not tried to take his relationship 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.
- 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.
- 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. And 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. And Yang wears noise-cancelling headphones that don't seem to help.
- 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.
- 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.
- Light loses his virginity to Ruyk in A Charmed Life.
- In Hellsister Trilogy, Supergirl hooks up with Dev-Em and loses her virginity to him after the war against Mordru is over.
- Back To Us has Adrien and Marinette consummate their relationship at the end of chapter 35.
- The plot of The 40-Year-Old Virgin.
- 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.
- 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."
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- The book Ready or Not by Meg Cabot 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 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.
- 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.
- Twilight. It is a main plot point over the course of the entire third book, and results in creating the plot of the fourth book.
- 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).
- Trapped on Draconica: Daniar and Kalak. Kalak was having a breakdown due to recent events and his jerkass mask slipped. Princess Daniar comforted him and this happened. As per the trope it worked because it was spontaneous.
- 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.
- Done with so much subtlety in Mockingjay that readers are still debating whether or not Katniss and Peeta were having sex or just making out.
- 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.
- The 'First Time' is apparently an important rite of passage on Lothar. 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 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.
- In The Hearts We Sold, Dee loses her virginity to James, after overcoming her discomfort with intimacy (physical and emotional).
- 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.
- 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 makeout 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 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 Kingkiller Chronicle, the teenage Kvothe's first time is with a thousand-year-old Fae demigoddess of lust who's infamous for driving men insane with desire for her. Somehow, he impresses her with his prowess. Beginner's Luck?
- 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.
- 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.
- Degrassi: The Next Generation has done this at least twice.
- Felicity's title character played out this trope with David, her boyfriend at the time, complete with spontaneous reversal.
- 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?
- 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. And 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.
- Twisted example on the first season of Gossip Girl: 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.
- 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.
- 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.
- Seth and Summer on The O.C.. In fact, their first two times were awkward, for very different reasons.
- Roseanne subverted this well in the episode where Becky timidly appealed to her Overprotective 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.
- 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.
- 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. 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 were pretty much a Running Gag, and his friends constantly teased him for it. He finally loses it off-screen in the fifth season to his older co-worker Nina. It was... aaaaaaawkward.
- 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. 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!"
- 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.
- 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).
- 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.
- 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.
- iCarly parodies this in iGet Pranky with Carly's first prank:
Carly: I'm sure it'll happen... when I meet the right person.
- Glee devoted an entire episode to this (it's even called "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.
- This was also 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.)
- 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).
- 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?
- 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.
- 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.
- 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.
- 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".
- 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.
- 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 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.
- 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.)
- Happens in each route of the original Fate/stay night, for Shirou at least, 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... They do have a much better time together in Fate/hollow ataraxia though, 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.
- Not helped by the fact that Shirou's... size makes Rin even more nervous.
- 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. And 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 Sunrider, flashbacks show that Kayto Shields and Ava Crescentia had their first time back in high school, days before Avas 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.
- Sticky Dilly Buns 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 and thoughtfulness make the sex about as good as it could get for Ramona (and probably for him too).
- And when Ruby thinks that Andy is proposing sex, she is initially nervous, but talking to friends and thinking about the best way to handle things calms her nerves, and is clearly a valid approach, whatever subsequently happens; Ruby has only recently made all these friends, and now they help her. The fact that actually getting to the sex itself turns out to be more complicated than expected is just one of those things.
- 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.
- Milo and Liam go through this in chapter 5 of Tripping Over You. They wind up having to consult the Internet for advice. It seems to go smoothly in the end, though.
- Part of Milanor and Kylier's backstory in Dept Heaven Apocrypha, though it's treated as a Noodle Incident - the only certain details are that they did it way too soon, and the fallout estranged them for quite some time, though they're back together by the start of the plot.
- 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 getting 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.) 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.
- 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.
- An episode of Pepper Ann mirrors this plot, except that the first time in question is a First Kiss.
- Parodied in Bob's Burgers except it's about eating lobster.
"When you get married, just pretend you've never eaten lobster before."