I, too, find the oddity of virginity loss baffling. I'm actually working off of Evil's first post to give clarification as what i'm talking about:
From an anthropological standpoint, the loss of virginity is one of the keypoints in a person's life. I mean, it is still a major point that our society revolves around, even if we don't say it in as many words. Yes, its all "sex, sex, sex", but there's a rarely discussed point about virginity, other than if you're still over over a certain age (depending where you are), you're something of a loser.
Most of the time, when someone loses their virginity, its a fumbling effort, where someone is apologising and trying to clean up a little earlier than expected. No one talks to younger people about the need for foreplay and why taking a day or so for foreplay makes sex even more fun.
And with regards to the idea of pain during the first time, its less to do with the breaking of the hymen and more to do with the vagina (theoretically) being unused to the shape of the penis, as well as, if her partner is also a virgin, then chances are, he's kinda brute forcing it (not literally, but you can understand that during a first time, a guy isn't going to know the best position for his partner, everything else comes from experience).
But from a storytelling aspect, its wish fulfilment. Everyone wants to have their genitals fawned over (well, there are some people who liked getting humiliated, not my thing but they do them). In a strange way, if the virgin looks at the guy's dick and she shows a little fear, it kinda boosts the guy's ego. Everything about the fantasy of taking someone's virginity is a form of wish fulfilment: "Its so big!" or "It did hurt a little bit, but now it's starting to feel better!". And if you feel metal enough, hey, you got blood over your dick. Throw the horns.
And at the end of the day though, its a porn game trope. Its something players expect - much like someone having monster dicks and fighting monster dicks.
Just putting it out there, i'm bi-sexual and lost my v-card with a best friend (male), who at the time was a virgin (among other things that we won't talk about it).
But what I've learned growing up in a rural Florida area, the stigma of masculinity is that anything girly or flamboyant behavior is seen as "unmanly" and deemed to be a black mark sign of the plague in the same vein as "he's is unworthy of your golden cunt!" Anything that deviated from the mindset are also of the kind of homophobic people that are sure to treat you like a leper for being a non-straight person. With this in mind for context to where i'm taking this:
The people I've known that are virgins were scared into believing that their feelings of being intimate with their feeling with their partners was considered unmanly and uncouth and that their fathers, brothers, uncles and other types of male role models tell them to be as down-and-dirty as they can get. Either it was intentional or not, my parent's generation shifted after my generation in a weird way in which virginity is treated as a trend, a fad, or something that's less important as people begin "coming out of the closet" and declaring themselves publicly as gay, trans-gendered, lesbian or associated. The original mindset was "This is the holiest of holy you're playing with, boy! Fuck them like a real man!!" to "Oh, you're a virgin? That's fine, i guess? Can i continue now or are we done here?"
When i lost my v-card together with my ex, we were understandably nervous about it and it felt better than i thought it would have which essentially had broken the mold on what i thought the treatment of virginity was meant to be like. I thought i had to be a burly man, i have to get down into the dirt and grime and plow that rich grove soil and plant my seed into that fertile womb! But when i i lost my v-card, it was just me and him in a hot tub talking and leading to a freeing moment that we were actually able to express how we felt as friends which he climbed on top and got to work. The intimacy was there and it was palpable, there wasn't aggressive hair pulling or forcing my manhood into them, calling them a dirty butt slut it was just a calm, sensual experience that didn't need the words to express our love and comfort in each other's presence.
There was a sense of obligation, when we had sex, where i wondered if this is what it was like to no longer being a virgin - too scared to be yourself and that changing yourself to fulfill the arcane justification of masculinity for us men. It felt wrong that i had to fit the bill of being the ideal man, that what i wanted to do was wrong and i was shamed for wanting to do it that way. I chalk it up to growing up with really mean assholes that never got laid or never stayed together with a person more than two weeks, but these ideas of power fantasies where we have to treat sex as a game that needs to be won instead of being gentle and patient about sends the wrong message. The generation i'm watching now has been ostracized and castrated.
Women from #MeToo and the Neo-Feminism movement are formed by enraged by the treatment of "men", LGBT takes a backseat, policies are reformed to suit the public outcries of a movement that adds toxicity and fuels distrust in relationships between men and women. Men aren't allowed to be gentlemen anymore, flirting in the workplace is seen as a form of sexual harassment, and i think it stems from my previous generation being overzealous about power fantasies in the bedroom that eventually lead to the new generation being so polarized and emasculated to how to take sex and taking someone's virginity. Just listening to my co-workers talk about sex with a few partners younger than them talking about how they don't care if the guy takes their v-card or an extreme case: one co-worker being a virgin doesn't want to have sex with any woman because of how public views have since changed to where women will put them in jail or not being good enough for them.
Obviously, my co-worker is out of his mind for thinking this but it got me thinking: if our sons in elementary school are being expected to be like their girl classmates and their treatment to be more feminine, what's that doing to people like my co-worker when he sees a woman he wants to be with? The tables have flipped.
We have gone past the foreplay and we're paying for it because we didn't teach our younger generation to be more intimate and actually giving a real heart-to-heart talk about sexual without all the sugarcoating and the cold calculative clinical terminology. We've grown up through trial and error, there wasn't a book to teach us the proper way to be regardless what the damn Church says, nobody knew what they were doing and we've procrastinate around the issue long enough. We've taught the new generation enough of the wrong things that they don't know what the fuck to do and we don't know how to help them because even we haven't figured it out.
There's men and women out there in the world in their fifties and sixties still virgins that were treated like garbage and ashamed while some were treated like gods placed on a pedestal but fail to understand why they were placed there in the first place. Virginity IS an important issue deeply rooted but never talked about because it is TABOO and it is because of that, nobody bothered to changed the rules of tropes we seen in porn, movies or video games. It's going to stay like that until someone has the balls (or tits) to bring up the topic and force people to talk about it without hamfisting Political Correctness down our fucking throats.
Again, sorry for the rant. This was i topic i wanted to talk about for a long time but never found a reason to.