Chapter 28 - 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.
What the fuck is wrong with you?
"What's the date today?" I asked in an attempt to distract myself from the horrific emotional morass in which I'd become mired.
The four girls raced to check their phones, but Ashley crossed the finish line first with the information.
"March fifteenth!"
I grunted. "The Ides of March."
"Hey! Julius Caesar!" Ashley said.
"That's right. Anyway, mark your calendars, because on this date, you all accomplished something pretty fucking significant, in my opinion. And you did it for the last time."
"Wait, what did we do?" Ashley asked, and the other three pelted her with pillows.
"We got laid, genius," Courtney said derisively.
Ashley looked at me confused. "But you said we did it for the last time."
"I meant you had sex for the first time." She still didn't get it. "You can't have sex for the first time ever again. You can only...you know what, forget it. You got laid, and I'm certain you'll get laid lots and lots more times in the future."
"OH! I get it now!" she said and fell backwards in a fit of giggles as more pillows flew her way.
I had a thought and went to the fridge to collect the last of the beers. We'd gone through most of a twelve-pack, but two remained. I brought them with a sleeve of red Solo cups back to the table and distributed the contents of the cans between the five of us. When everyone had a cup, I lifted mine to offer a toast.
"Here's to your first times."
"The First Timers Club," Kayla said.
"The First Timers Club!" everyone shouted.
I drained my cup and suddenly felt incredibly weary. Kayla had kept me up for most of the previous night and I'd had vigorous sex with the rest of them for most of the day. I knew I wouldn't last much longer. Brittney noticed the second time I yawned and gave me a look, but I tossed her an okay symbol and she grinned and quietly clapped her hands.
Why had I agreed to have sex with her tonight? It had seemed such a no-brainer idea at the time, when she'd clung to me with that dreamy post-orgasmic look on her face and fuck-me eyes, with my cock throbbing for release, but now I regretted it. Maybe she'd be up for a cuddle? She could be the big spoon.
Kayla and Courtney received numerous text messages from their parents until, finally, they had to pack up and leave. Brittney tossed Kayla her car keys and the four girls hugged and promised to meet back at the pool house by noon the next day.
When they'd gone, Brittney and Ashley attempted to teach me to play Magic the Gathering, but I had no idea what I was doing and they easily mopped the floor with me until I begged to sit out and just look at the artwork on the cards while they played against each other. This turned out to be a good idea, because it was far easier for me to pick up on the nuances of the game's strategy by watching two proficient players go at it.
Finally, the time had come for the two of them to go as well. Clay would be home soon and it would be better if they were in the house when he did, so there'd be no excuse for him to come looking for Ashley. I gave them hugs and whispered to Brittney that she shouldn't leave the butt plug in for too long. After a quick pitstop to the bathroom, she emerged and subtly let me know she'd left it in there.
I flicked off the lights and climbed to the mezzanine, thoroughly exhausted. After plugging in my phone, I set my head on the pillow and promptly fell asleep.
Chapter 29 - Irish Massage
A series of message alert awakened me from one of the deepest sleeps I'd had in years. I peered at the screen's dim glow through a barely cracked eyelid and knew who it would be. Another alert brought me closer to full consciousness and I reached for the phone to check the messages.
Ash is asleep
U still up or did u crash?
Packing up to come over
Be there in a few
Bringing goodies
I went downstairs to unlock the slider for her and then crawled back into bed to wait. I heard the slider open and shut and the click of the lock and the creak of the stairs as she ascended to the loft.
"Oh, you're awake," she whispered when she found me browsing my phone. It amused me that she and Kayla had both felt the need to whisper.
"Your messages woke me up," I said in a normal voice, setting the phone down and turning on the bedside lamp. I noticed she had a large reusable shopping bag in her hands. "What's that?"
She looked at it and her face brightened. "Oh, I noticed your shoulder seemed to be bothering you earlier." She reached in and pulled out a bottle of baby oil. "Thought you could use a massage."
I could have kissed her. I'd almost texted her back to ask for a rain check and now I'm glad I hadn't. She set the oil on the bed but more items filled the bag.
"That sounds amazing. What else you got?" I asked.
"Some snacks and stuff from the kitchen. I noticed the fridge here was just about empty and you've barely eaten anything for days, so I brought you a bunch of chips and cookies and stuff. I know it's not very healthy, but hopefully it's better than nothing."
It could have been rendered hog fat for all I cared. My stomach grumbled at the mere mention of food and I held out my greedy hand for the bag of cookies she pulled out. While I stuffed my face with shortbread chessmen, Brittney sat primly on the edge of the bed to watch me. I held out the bag to her and she took a cookie to nibble on. I tilted the bag back to slide the last two into my mouth, then tossed the trash onto the nightstand.
"Oh man, that was great," I said. The carb hit perked me up and I felt more energetic. I noticed Brittney's outfit. A matching set of pink fleece pants and a zip up hoodie. "What's up with you and sweats?" I asked her as I dug into a bag of pretzel sticks.
She looked down at her attire and shrugged. "It's hard to find clothes that fit my body," she said. "Plus, they're comfy."
I lifted my eyebrows and tilted my head from side to side. "Makes sense, I guess. You look way better naked though. Why don't you take them off?"
Her eyes twinkled and she stood and unzipped her top, then pulled down her pants and kicked them both under the bed. She hadn't bothered with underwear. She took the shopping bag from me and pulled out a box of tampons and a large beach towel. The tampons went onto the nightstand, and she waited with the towel for me to move.
I stood while she pulled the duvet and top sheet down to the footboard and spread out the beach towel in the center of the bed. Then she picked up the oil and flipped open the top.
"Lay down."
I didn't want to let the bag of pretzels go, but I wanted a massage more. I laid down on my back and put my hands behind my head.
"On your stomach," she laughed.
