The First Timers Club

“Wait! Back it up, like, fifteen seconds. No, you went too far. Stop! Forget it, just play it from there. This is fine.”

We’d watched Courtney’s video for the past hour, and for the sixth time, my cock penetrated her pussy for the very first time and for the sixth time, Courtney cried. Kayla rolled her eyes and hid her face in a pillow, while Ashley and Brittney quietly discussed video game strategies they planned to employ later that evening.

“I think we’ve watched it enough. How about we do something else now?” I suggested.

She glanced at me and sighed. “Fine. Let me just watch the money shot one more time.”

I fast forwarded to a medium shot of her jacking me off onto her tits, and I had to admit that Kayla had done a great job of capturing the moment, even incorporating a slow-mo effect to draw out the ejaculation and splashdown. And Courtney’s onscreen tits did look spectacular covered in my cum.

When the video finished, I resumed the porn playlist and lowered the volume. The sun had finally set and we all pretended that in a few short hours, we wouldn’t have to disband and go our separate ways until the next day. I could have hung out with the four of them for days and days, and the realization of that made the looming melancholy even worse.

I stood and winced from the pain in my shoulders. Carrying Courtney to the lounger had proven to be the proverbial straw, and it now felt like a troop of tiny cub scouts had built a campfire between my shoulder blades. I rotated my arms and took my spot in front of the television. The idle chatter diminished until they all sat quietly waiting for me to say something.

“Hopefully, this doesn’t sound too stupid,” I began, and Brittney flourished her hand.

“Just say what you feel,” she said, impersonating my voice, and I pointed a finger gun at her and winked.

“That’s really great advice,” I said and collected my thoughts. “I just wanted to say that the past couple of days have been amazing, and I’m grateful to have gotten the chance to meet the four of you. You’re some of the smartest, funniest, kindest, and sexiest women I’ve ever had the privilege to know and I feel honored that you invited me into your circle. There’s no doubt I’ll cherish this experience for the rest of my life.”

I watched four smiles fade as they exchanged glances and my stomach sank. Had I said something offensive? Had it been too much? Why were they looking at me like that?

“What’s wrong?” I asked.

“Are you leaving us now?” Ashley asked.

“What? No! I was just thanking you all for an amazing time so far. Why? Do you want me to leave?”

“No!” Courtney shouted, leaping to her feet. “Are you fucking kidding, dude? I’m trying to figure out how to sneak you into my bedroom. You’re really not leaving?”

Reassured that I hadn’t said something stupid, I laughed. “Fuck no, I’m not leaving! We’ve just gotten started.”

The look of relief on their faces sent a flood of emotions coursing through me that I hadn’t felt in ages. I contemplated that I would have to leave them at some point, and the realization of that filled me with an overwhelming sense of impending loss. I didn’t usually form these kinds of bonds with the women I slept with. If any one thing defined me, it was my stubborn refusal to get attached to anyone. I cherished my independence and preferred to remain aloof and emotionally unavailable. But at that moment, and for the first time in a long time, I imagined a future that included these four girls and it shook me.

There could be no future for us, of course. I was well over twice their age. I’d already lived out my youth while they still had theirs ahead of them. We just happened to share this particular slice of time together, and when it ended, that would be it. We’d go our separate ways, and only remember each other during particularly sentimental moments that would inevitably fade from memory for months at a time to start, but then for years thereafter.