29 year old virgin

Online dating is a goddamn nightmare. Full of left-swipes, ghosting, and unsolicited dick pics 🍆. After years of trudging through the digital dating wasteland, I had pretty much given up when I matched with Josh.

Josh wasn’t like the others. No sleazy opening line, no gym selfies, no desperate "Hey beautiful" followed by radio silence 12 hours later. His messages were thoughtful, sweet, and surprisingly funny. The conversation flowed naturally, without that awkward forced vibe most dating app exchanges have. He was interested in me — my job, my favorite foods, my childhood dog’s name — and seemed genuinely invested. It was so unlike the usual routine that it almost made me suspicious.

And then were his pictures.

Holy. Shit.

Tall, dark, and stupidly handsome 🔥. He had that effortless I woke up like this sexiness — tousled dark hair, deep brown eyes, and the kind of jawline you could sharpen knives on. Six-foot-seven and built like a professional athlete, with arms that looked like they could pin me against a wall and make me forget my own name. He could have been a model or a rugby player or some hybrid of both. And yet, his messages didn’t reflect any of the usual arrogance that came with that level of hotness. If anything, he seemed almost… shy 🥺. It was a confusing and intriguing combination.

They say you shouldn’t put too much stock in someone’s profile pictures because filters and angles can work miracles, but Josh was the real deal. When he walked into the bar for our first date, I nearly choked on my drink. He was even better-looking in person — tall enough to command attention, but with a softness in his expression that made him seem approachable.

But the moment he sat down, he started fidgeting. His eyes darted around the room, and he barely made eye contact. His hands rested awkwardly on his thighs, like he wasn’t sure what to do with them. The contrast between his intimidating exterior and shy demeanor made him strangely more attractive. Here was this god-like man, clearly uncomfortable and nervous in a way that made him seem… human.

The date itself was surprisingly sweet. He was polite, asked questions, listened — all the things that are shockingly rare in the modern dating world 🙃. He paid for the drinks, walked me to my car, and gave me a brief hug before saying goodnight. No kiss. Not even an attempt. Although I totally would have welcomed it.

The second date followed the same pattern. Drinks at a cozy bar, pleasant conversation, a lingering goodbye hug — but nothing. No teasing hand on my thigh, no slow brush of his fingers down my arm — not even the kind of accidental touch that sends a shiver straight between your legs. By the third date, it was starting to feel like we were stuck in foreplay purgatory, and I was ready to start a fire myself 🔥.

Josh wasn’t shy about setting up dates or expressing interest in seeing me again, but there was a distinct lack of physical escalation. Either he was trying to be respectful, or he was completely clueless. I decided it was time to take control — and make him want it.

After our third date, I invited him back to my place. He hesitated for a second, then followed me inside. He stood awkwardly by the door, hands in his pockets, as I hopped up onto the kitchen counter and pulled him toward me. His eyes widened slightly, but he didn’t resist when I wrapped my legs around his waist and kissed him.

It was immediately clear that this was a mistake.

His tongue shot out like a rogue eel, clashing against my teeth, and I’m pretty sure he full-on licked the side of my face at one point. His head bobbed and weaved, always in opposition to mine, and his whole body was stiff as a damn ironing board.

But I was already committed, so I decided to give him a chance to recover. Maybe he just needed to loosen up. I pulled him toward the bedroom, guiding his hands to my waist as I lay back on the bed and invited him to join me. He climbed on top of me, his body stiff and heavy. His arms were planted on either side of my head, like he was about to start doing push-ups.

He stared down at me, breathing heavily. His body pressed down with the weight of a small car, and my ribs started to ache. His movements were mechanical, like he was trying to follow a step-by-step instruction manual but had skipped the chapter on finesse. He started awkwardly sliding up and down my body like a malfunctioning robot, his face inches from mine, breathing directly into my mouth.

All I could think about was that scene from the Inbetweeners where Will looks like he’s planking his way through sex with Charlotte — except this was somehow worse because it was happening to me.

Every awkward thrust pressed his full weight into my chest, and I was seconds away from suffocating. His eyes were locked on mine, intense and glassy, like he was trying to telepathically figure out what to do next. My ribs screamed. My face screamed. My vagina was preparing its letter of resignation. This was not just bad sex — this was catastrophic sex.

Hoping to salvage the situation, I rolled onto my stomach and suggested he try from behind. He nodded enthusiastically, positioned himself, and then —

Pain. Blinding, searing, excruciating pain.

Josh had missed. Completely.

His very sizable p — which under different circumstances might have been an asset — had slammed at full force into a place that was absolutely not prepared for penetration. The shock of it ripped through my entire body. I screamed. My legs gave out beneath me as my hands flew to my lower back.

Josh froze. His face paled. "What happened?"

Blood. So much blood.

My body tensed up instantly. My hands were shaking, and I was furious. Josh’s face went pale, his eyes wide with horror 😨. It was hard to wrap my head around how he thought that was okay — even if he wasn’t sure what I meant, common sense should have kicked in. How would he like it if someone shoved a giant apparatus full force up his backside?

"You need to drive me to the hospital," I managed.

I hobbled in agony to the car, mortified and humiliated. I curled into the passenger seat as tears ran down my face. The pain was unbearable, and the sight of the blood made it worse. We didn't speak the entire way to the hospital.

At the ER, the nurse’s expression was sympathetic but unsurprised. She handed me a clipboard while casting a side-eye glance at Josh, who looked like he wanted to melt into the floor.

The doctor’s face remained neutral as he examined me. "You’ve got a pretty severe tear," he said casually, like he was talking about a scraped knee. "You’ll need stitches."

STITCHES.

I almost fainted right there on the exam table.

I lay on the exam table, listening to the doctor calmly explain the aftercare instructions — no strenuous activity, no sex for several weeks (yea, duh), antibiotics for infection. It was the single most humiliating moment of my life.

When we left the hospital, Josh didn’t say a single word the entire drive back to my apartment. He just sat there, hands gripping the steering wheel like he was trying to crush it, eyes glued to the road like he was in a hostage situation. I stared at him for a minute, waiting for him to say something — an apology, an explanation, a desperate offer to cover my medical bills — but nothing.

Finally, I broke the silence. "So… you wanna explain what the fuck just happened?"

He stutted "I… I’ve never done that before."

My head snapped toward him so fast I nearly gave myself whiplash. "You what?"

He glanced at me, his face completely drained of color. "I’ve never had sex before."

"Dude." My mouth practically unhinged. "You’re a virgin?!"

It suddenly all made sense — the awkwardness, the stiffness, the cluelessness. A 29-year-old virgin with the face and body of an underwear model. The complete disconnect between his looks and his inexperience was almost comical. If I wasn't in so much pain, I'd probably feel sorry for him.

Josh texted a few times afterward, saying he wanted to "make it up to me". And that’s when the neediness kicked into overdrive — constant messages, fishing for reassurance, asking why I wasn’t into him anymore. Like, do I really need to spell it out for you, babe? You torn me a new one, literally.

Obviously that was the end of Josh and I. And doggy? Let’s just say that position is off the table indefinitely 🐶🚫.