Their First Time

""Be gentle...""

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.

An example of how curious TV sexuality is. Someone, usually the woman, researching sex, talking about it, etc. for a few days seems to be a subconscious indicator of immaturity and one of the couple will usually put it off "until they're ready."

Realizing both are "ready" usually takes 30 seconds, enough time to ask "Are you sure?" and then going for it. Implied is that the less conscious thinking about it, the better. Or that all the thinking they've already done has only heightened their anticipation.

Interestingly, this may be related to the Unspoken Plan Guarantee.

Happens in Soap Operas a lot.

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 is as bad, but either way be sure to have lots of angsty talking about it.

Anime and Manga

 * Lovable Sex Maniac-wannabe Yamada from B Gata H Kei is desperate to lose her virginity, and she ends up failing miserably in various hilarious ways. The entire show revolves around it.
 * Poor, poor Kira Yamato, from Mobile Suit Gundam SEED, whose first time was with his long-term crush, Flay Allster, who was attempting to seduce him into exterminating the rest of his race out of Fantastic Racism toward the Coordinators following her Freak-Out after her father's death.
 * What can you expect when Jesus has sex?
 * Pretty much the whole chapter 52 of Mirai Nikki is dedicated to this.
 * 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 hinted in Shaman King that went through this right before   And later
 * The Shin Kimagure Orange Road movie has doing the deed almost at the end. It also overlaps with
 * 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
 * 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.
 * A plot point in Crying Freeman. Both Yoh and Emu 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... but as her last wish, she wants him to have sex with her. Yoh tells her that he's a virgin too and accepts to have sex with her - and not only they "deflower" each other, but he falls for her and takes her in.
 * Official Couple Hoshino Hajime and Negishi Yumiko from Love Roma subverted the Unspoken Plan Guarantee aspect of this trope by discussing the subject extensively before making a go of it, and while it's as awkward as one would expect of two virgins, it's nonetheless very sweet.

Comic Book

 * The Sin City series begins with the main character losing his virginity to a beautiful young woman. And then the girl appears dead, and said main chara is framed for her murder. Since this is a Crapsack World, he decides to not even bother clearing his name and goes straight search 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.

Film -- Live Action

 * 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.
 * 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."

Jokes

 * 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 !@#$%^&*!" And a voice from the next room over yelled back "FLIP HER OVER!"
 * A 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

 * The second chapter of Candy by Terry Southern had a chapter dedicated to the titular 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 Princess Diaries series..
 * The book All-American Girl: Ready Or Not by Meg Cabot (same author as The Princess Diaries) focuses on this. The protagonist Sam Madison is the girlfriend of the First Son and an 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, 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 the act.
 * Tamora Pierce has written several. Kel had some time to consider it and at least two aborted attempts with Cleon, Daine's and Kel's actual first times were both after the series finished. Alanna and Aly both had rather unplanned ones during the series; they hadn't actually 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. Now Your Mileage May Vary, but there is much Wangst involved, but in a subversion, They Do.
 * 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).

Live Action Television
"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!"
 * 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.

"Carly: I'm sure it'll happen... when I meet the right person."
 * 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.
 * He did though, once fall asleep in the same room with her accidently and then in the morning bragged falsely to other boys who thought he had had sex with her. In other words he selfishly played with Topanga's reputation in a way that would once have been worth his life. Fortunately he has the integrity to at least confess to it which saved Topanga's reputation as a "nice girl". More astoundingly he was forgiven by Topanga which was really more than he deserved. A bit of a pity because Cory is usually a nicer person.
 * Willow and Oz in Buffy the Vampire Slayer. An interesting example, as it's the female who wants to jump Oz's bones, but Oz declines, saying it's just to make Xander jealous, and she's not ready. They do finally make love in a Crowning Moment of Heartwarming 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
 * 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.
 * 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.
 * Seth and Summer on The OC. 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 wish 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.
 * 7th Heaven.
 * 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.
 * Donna and Eric in That 70's Show. 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!"
 * 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.
 * Fez's attempts to lose his virginity were pretty much a Running Gag.
 * 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).
 * In season two of True Blood, Hoyt and Jessica lose their virginity to each other. Then later, they later found out when they 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.
 * 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,
 * iCarly parodies this in iGet Pranky with Carly's first prank:


 * 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 because A Man Is Not a Virgin. 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 highly 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).
 * A groundbreaking example comes from 1978, when—in possibly the very first Prime Time example of this trope—the titular James Hunter of James at 15 lost his virginity to Christina Kollberg, a Swedish exchange student, prompting the change of the show's title to James at 16. It also prompted nervous executives to forbid even the euphemism "responsible" for birth control and to require that James feel bad about it afterward.

Music

 * The All-American Rejects' "Dance Inside" is a good example of this.

Visual Novels

 * 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 Shirou calling her by last name... even while coming.
 * Also happens in each route of Katawa Shoujo. The most glaring example comes in 's route, where , but  . (Not helped by how.
 * Goes more smoothly in 's route, where

Web Original

 * 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.
 * 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.

Western Animation

 * 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.
 * An episode of Pepper Ann mirrors this plot, except that the first time in question is a First Kiss.