The Disaster That Was My First-Time Sex, and the Lessons Learned

What My 20 Year-Old Self Thought She Knew and What She Should Have Known

The first time I had sex, I felt as though my whole body was engulfed in fire, raging from my cervix straight to the back of my skull. Buckets of sweat and tears were involved, and more than once I asked myself why people pretended to like sex. I may have wondered if there was something wrong with my vagina. 

I hadn’t planned it. I had been making out with my ex-boyfriend for months now and that day was supposed to be another regular Make Out Day. I also thought I knew what to expect, having grown up immersed in romance novels. From the moment I read my first Harlequin romance at the age of ten – a tale of a wealthy, handsome man entwined with a demure virgin – until I had sex for the first time, just two months shy of my twentieth birthday, I’d consumed hundreds upon hundreds of romance novels. My romance novel conquest spanned across various subgenres: billionaire romances, mafia dramas, small-town tales, enemies-to-lovers plots, historical adventures, queer romance, feminist romcoms. I even enjoyed my fair share of paranormal and dystopian love stories, despite not being particularly fond of fantasy. 

I’d devour steamy pages in the most unlikely of places – the bathroom, during Church services, even during class while my mathematics teacher droned on about complex equations, the book discreetly hidden within my maths textbook. Between the age of twelve and seventeen, I’d already had more than a few orgasms that had left me breathless and on the edge of my bed in the middle of reading romance novels that have since faded from memory. In fact, I considered myself a teenage sexpert, teaching my friends who were already having sex, about sex. So sex wasn’t foreign territory to me. I’d read books and watched TV shows depicting every possible kind of intimacy, from various orgasms and positions to first-time experiences. 

Yet, armed with this wealth of knowledge, nothing could have truly prepared me for the reality. 

The Reality of First-Time Sex 

In MLW romance novels, first-time sex on the woman’s side – it is always the woman who is inexperienced – goes like this: They kiss hotly, maybe throw in some oral sex and skillful fingering. The man says some variation of, “I’ll be gentle, I’ll make you feel so good.” He’s our hero so true to his word, he does make her feel good. He wraps her legs around his neck or hooks his arms around her knees, and “thrusts” in. There’s a jabbing or shocking or pinching pain the first few times. But just like that, the pain subsides to earth-shattering, toe-curling pleasure. Her eyes are rolling to the back of her head. She can hardly breathe. She’s seeing stars. She’s seeing Jesus Christ in heaven. She’s begging for more. 

Well, I begged for less. 

My ex-boyfriend was kind and warm and funny, and that translated in bed. He was genuinely patient. When I said “wait,” he waited. When I needed a break, or to come up for air, he rolled away. There is nothing he did not offer to ease my pain, but my pain could not be eased. 

First, nobody tells you how ridiculously painful penetration is. I was exceptionally wet, and aided by a very fine lube, I might add. Still, my vagina refused to be penetrated. At some point I looked down at my vagina and cried, “WHY?” I suspected my vagina was broken, or was just wrong, or something in my biology was certainly askew somewhere. 

There was also a lot of blood. We exhausted a roll of tissue. We changed the bedsheet. It was a blood festival. A weaker man – and frankly a weaker me – would have been scarred.  In fact, my first time wasn’t even a ‘first-time’, because my partner couldn’t get all the way in. He would kiss me, encourage me, ask me. He would go in, and the pain would shoot to the back of my skull and I would be unable to breathe and I would shout, “Stop, stop, stop!” 

We went at this for two hours. The most we went was halfway before I grew terribly exhausted, drenched in sweat, and called it a day. For two days afterward, I couldn’t walk straight. My bones were chiming and my body was on fire. Everywhere hurt. Physically, yes, but inside my chest hurt from the treachery too. Woe to all my romance novels! They’d betrayed me. And a few days later when I rewatched Saoirse Ronan’s character in Lady Bird have sex for the first time, while on top, I wanted to slap all of them through the screen. 

Navigating Expectations: Culture vs Personal Experience 

To be fair, probably nothing could have prepared me for my first time. Anyone could have told me, “It’ll be really painful,” but how really painful? Is there a universally accepted sex-pain scale? Anyone could have said, “You’d bleed a lot,” but how much is a lot? No two people experience sex the same way, even if both of their sheets are soaked in blood. I’ve never been scared of needles and never understood having a fear of blood, of the very thing that courses through your veins. Still, I was impossibly horrified by how much blood I was losing in the name of sex – or an attempt at sex, at least. 

We are also living in the most sexually liberated climate in the history of humankind. Sex is everywhere. On social media, within the pages of our books, on our TV screens, in the music we bob our heads to. The media is constantly telling us what sex should feel like: pleasurable and glorious and back-blowing and breathtaking. 

But what about the less glamorous aspects of sex? What about challenging the ideals portrayed in the media? What about being more open and honest about these unsexy parts? 

Sex is fantastic and delectable, and frankly as a begrudging, intermittent Christian, I often doubt that such a perpetually furious Biblical God designed it. I bet it was right after that He rested. A 10/10 invention. But sex, especially our first few experiences, can also be painful and messy. 

Societal norms, however much we rage against them, still often overshadow individual experiences, which is why it’s so important to shed light on the less glamorous aspects of sex. Everyday, we’re bombarded with idealised portrayals in the media, but the ugly and bloody parts are just as real and valid. Embracing these aspects doesn’t diminish the thrill of sex; it adds depth to our understanding, and authenticity to our expectations. 

My own reality, though marked by horror and uncertainty, ultimately led to a deeper appreciation of the multifacetedness of sex. Despite the challenges, my first-time experience was success-ish (third time was the charm, hurrah), not because it mirrored the fantasies of romance novels or what I’d seen on screen, but because it was uniquely mine. 

As we continue to explore the goldmines of sex and intimacy, let us always remember that every first-time experience, no matter how messy or unglamorous, is valid and worthy of acknowledgment. 

Shalom Esene is a 2024 Adventures Writing Creator and a culture journalist who focuses on feminism for mediocre, bad, and ordinary women. Her work is featured in OkayAfrica, Lolwe, Black Ballad, and others.