Confessions of a Virgin on a Dating App

Prologue

“ I t won’t fit.”

Those three words were the first indicator that something was wrong.

Very wrong.

I winced as he struggled above me, his enamored joy twisting into frustration as his face turned red. Tyler was nearly twice my size – a foot taller than me and wrapped in lean muscle from years of athletics and weightlifting. I, on the other hand, was barely five foot two and on the verge of being unattractively thin. A minute ago, I had been fretting about exposing my A-cup breasts and wondering if his pelvis would crush my tiny, protruding hip bones.

Now I had much bigger problems.

I winced as he tried again, attempting to relax my legs as they quivered uncontrollably. This hadn’t been my idea, but after much persuading, I had agreed to let my longtime boyfriend take my virginity. After all, we were that couple, together since freshmen orientation at our tiny Christian college campus. Always at each other’s sides, unwaveringly loyal to each other, and sickeningly in love.

I cheered in the stands at his football games, and he gave standing ovations at my choir recitals. We were a perfect match, and Tyler told me he intended to propose as soon as we graduated.

“So, since we’re going to get married anyway,” he had insisted. “I want to do this now.”

I initially balked at the suggestion, feeling nauseous with betrayal. I was concerned that my loving boyfriend was one of those guys my parents had warned me about. All they want is sex, they’d told me. And they’ll say just about anything to get it.

But over the past few weeks, as he continued to bring it up, I gradually warmed up to the idea. We’ve been together for almost four years. He loves me. And he’s right – if we’re going to get married anyway, what does it matter?

Although my knowledge of the biology behind intercourse was limited, I’d always seen it as a warm, romantic act – the strongest declaration of love in the whole world. My campus’s education on the subject was minimal, focused more on drilling abstinence into students’ heads than divulging any useful information on how it all worked.

For that, I had to turn to the internet. And the resulting web searches nearly flipped my stomach inside out.

But Tyler had insisted that everything would be alright.

“I’ll make it romantic,” he told me. “I’ll put rose petals on the bed, get some nice candles. I’ll even sneak in a bottle of wine.”

His last promise made me even more uncomfortable, as alcohol was strictly forbidden on campus. But as the day came closer and my stomach-turning internet searches intensified, I decided that slight intoxication wasn’t a bad idea.

But I’d never had wine before, and it turned out I was a lightweight. One glass had my head swimming in a hazy fog, and the rose petals strewn across Tyler’s dorm room bed did little to calm my nerves. Even the candle was nauseating; an overly sickly-sweet fall scent that lingered in the back of my throat.

I’d expected it to be unpleasant. My internet searches told me that it might sting, or there might be some blood.

What I didn’t expect was for my vagina to deny entry altogether.

“Maybe we should try another position?” Tyler suggested.

My thighs clenched. I was already nauseous, uncomfortable, and quivering with anxiety. If we were going to do this, I wanted to at least be lying down.

But I loved Tyler, and I wanted him to be happy. So I reluctantly agreed to try more positions. Most of which I wasn’t comfortable with, and all of which resulted in the same issue. I knew virgins were supposed to be tight, but this seemed extreme. It was as if there was a wall at the entrance to my vagina, blocking off all access.

I jolted. Tyler was getting more forceful, taking out his sexual frustration on my shaking body. He tried again, pushing harder this time.

And I screamed.

It burned like I’d never felt before. It was as if my vagina were being torn in half.

“Avery!” Tyler hissed, clamping his hand over my mouth. “You’ve got to be quiet! They’re going to hear you!”

By they , he meant the dorm RAs. My neck craned toward the half-empty wine bottle on Tyler’s nightstand. Like alcohol, sex was forbidden on campus. Which meant we had to be discreet.

“This isn’t working,” I whispered, clenching my throat as I fought back tears.

Relief washed over my naked body as Tyler’s grip loosened. He sighed and shook his head, flopping down on the too-small twin bed beside me.

“It’s okay, Avie,” Tyler whispered in a soothing voice, rubbing my bare shoulder. “I know the first time is tough for girls. Let’s call it a night, and we’ll try again some other time.”

“Okay.”

No amount of throat-clenching helped. The tears cascaded in smooth curves down my cheeks, leaving tiny stains on Tyler’s pillow.

“Hey, hey.” He turned toward me, engulfing me in his tanned, muscular arms. Soothing shivers ran down my spine, like I’d just stepped into a warm beam of sunlight.

All my anxiety, fear, and pain melted away under the heat of his touch. Even if sex was an awkward, painful, confusing mess, I couldn’t deny how good his unclothed body felt pressed up next to mine. I curled into his embrace, our arms and legs locking together.

It will be alright . I reassured myself as my eyelids fluttered closed. After all, we love each other. This is just another challenge for us to overcome.

With my nerves settled and my breaths deep and slow, I almost forgot that I wasn’t supposed to be there. I wasn’t supposed to be in the men’s dormitory at a Christian college lying naked in bed with a man I wasn’t married to.

But at that moment, everything felt right. At least, right enough for me to relish our alone time for the next few hours.

Sex or no sex.

We tried again.

And a third time.

And a fourth.

With every attempt, Tyler had new suggestions. Enough lube to drown my entire pelvic region. Lidocaine cream that set my insides on fire and didn’t numb a thing. Every position imaginable, including some that seemed to defy the laws of gravity.

They all ended the same way. With Tyler becoming increasingly irritated, and me still being a virgin.

We decided to try one more time. It was three weeks until college graduation, and my roommate had made a trip home for the weekend, which meant that Tyler and I had my dorm room all to ourselves.

But with that arrangement came problems. Tyler’s bed was at ground level – mine was a loft with barely two feet of clearance to the ceiling. My dorm room was also much smaller, as the women’s dorms were older with awkward layouts.

But it would have to work. Tyler agreed to come over at 9 p.m. By then, the sweltering Florida sun would be well below the skyline, making it easier to sneak into the women’s dorms with a contraband box of condoms.

He’d offered to bring wine again, but I decided against it. I disliked the feeling of being drunk, and it hadn’t blocked out the pain the last four times.

Tyler was optimistic, but I was full of dread. He arrived shortly after the nighttime darkness settled in, slipping silently into my dorm room like a fugitive. From his backpack, he pulled out a large box of condoms and two bottles of lubricant.

“I brought extra supplies,” he chuckled, but it did little to ease my nerves. He sensed my fear and pulled me in for a tight hug.

I smiled, his familiar soothing warmth washing over me as I breathed in the scent of his Old Spice. That warmth caused a faint bit of hope to flicker in my chest.

It’s okay.

Everything will be okay.

You can do this.

It started as it always did – us unceremoniously stripping our clothes with plenty of kissing and cuddles. That part I loved. I could kiss Tyler all night, running my hands over the muscles that lined his back and shoulders. It brought out all the warm, lusty feelings that I knew were supposed to be there.

But then it was time, and every muscle in my body clenched. I had come to expect the pain now, and my body reacted accordingly. It was like a reflex.

We fumbled for a while, trying the same few positions that we always did. Tyler taught me some breathing exercises, and we focused on relaxing my thigh muscles, which were as rigid as steel.

“You’ve got to calm down,” he insisted. “Tensing your body will only make it worse.”

“Easier said than done,” I grumbled.

Tyler tried again. As usual, the wall was up, blocking his access. He readjusted, pushed, and readjusted some more, but it made no difference.

And if he pushed too hard, which sometimes happened, I’d be left screaming in pain with my insides on fire.

“Gah!!” I shrieked, my thighs squeezing his hips like they’d crush them. Tyler grimaced, but this time, he continued pressing into me.

“AH!! Tyler, stop!”

He still didn’t. His face was tight and red with frustration as he pushed deeper.

“You’re hurting me!!”

I went to shove him off me, but he was twice my size and wouldn’t budge. I struggled and screamed under him, my whole body on fire with panic.

I didn’t care who heard me.

I didn’t care if he got upset.

I needed this to stop.

Finally, I managed to pull one leg up to my hip, and a swift kick to Tyler’s genitals sent him tumbling to the floor.

My chest was shaking so badly that I could barely breathe. My mouth hung open, inhaling like I was starved of oxygen as Tyler writhed in pain on the floor.

He turned to face me; his frustration replaced with rage.

“What the fuck, Avery!?”

My blood chilled in my veins.

Tyler never cursed.

“Hello?”

The knocking sound was like a nail being pounded into my ears. I saw Tyler’s face fall in horror.

“Avery,” the voice outside the floor continued. “This is Madison, the RA down the hall. I heard a scream. Is everything okay in there?”

I didn’t answer. Neither did Tyler. It was as if the whole world was melting into a puddle around me.

There was another knock, then the metallic chime of keys.

“Avery, I’m coming in.”

My stomach fell to the floor.

We’d been caught.