Cabin Chronicles #2: Strip Pool (Patreon)

After the intro post this weekend, I'm starting this series off with a bang, and it's one you can't miss. Read it here, or for VIP members, head over to Discord to see the embarrassing photos and videos posted throughout. This is one of my favorite tropes, and I hope your pool cue is just as hard as the one I had to use...

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“Okay Ian, let’s go- it’s our turn to play pool.”

Grabbing one of the other pool cues, I just nodded even though I knew that Rob and I were both awful at this. John’s first cabin vacation with us a few years back had been eye opening because we finally saw what a real game looked like instead of just randomly shooting the cue ball around the table. After Rob broke, sending the balls skidding around the table, I decided to aim randomly and see what happened- all I did was send the cue ball careening directly into a pocket on the other side of the table.

“Oh my god!”

“C’mon John, be nice, it wasn’t that bad of a shot.”

“No, it wasn’t that, I just realized who you two look like!”

John had said for years that Rob looked like Prince Harry even though the only similarity was a matching hair color.

“You look like Prince Harry…” The groans from all of us almost drowned him out, but he kept going. “As I was saying, you look like Prince Harry when he got caught in that strip billiards scandal when he visited Las Vegas.”

It took me a second to remember, but once it came to me, I realized that I’d printed out the cover story from some English newspaper a decade ago… wait, did my crush on Prince Harry extend to why I’d first dated Rob? Looking up at him again, I realized that the answer was probably not since I still couldn’t see what John was seeing.

“I’d like one night with his crown jewels!”

Aiming his next shot, Rob sent a spray of balls across the table without getting a single one in. I lined up for my turn, but before I could, Rob had put down his pool cue and started to lift his shirt up, revealing his pale, stocky chest. I thought he’d drop it back into position with a laugh, but he continued pulling it off before throwing it over at John who caught it like it was the garter at a wedding.

“Your turn.”

That was all he had to say.

Taking my shot, I actually aimed this time, but one of the striped balls missed a pocket by just a millimeter, and I had a choice to make. Would I be a stick in the mud, or would I have some fun that I’d been neglecting for months? Even though my brain was yelling one thing, my arms were moving of their own accord.

Reaching up to grab the bottom of my tank top, Rob just wagged his finger at me.

“I’m feeling naughty- your shorts are your first item.”

“I didn’t get to pick your item!”

“Too bad…”

This was supposed to be a fun week away… this was supposed to be a fun week away…

Repeating those words, I decided not to say anything else as I pushed my shorts to the floor and stood there in nothing but my white briefs below my waist. The other guys gave me the same catcalls that they’d yelled at Rob so I knew that this was all in good fun, and I decided to say fuck it to my inhibitions.

Rob was up next, and I was too busy fantasizing about him joining me in my underwear that I didn’t even see him aiming his ball. He shot the cue ball across the table and directly knocked one of the solid balls into a pocket with a resounding swish sound.

I think I was being hustled.

Keeping my mouth shut, I walked across the room and saw that I actually had a shot! Lining up my pool cue, I took my time and made my shot… missing completely.

“Now you may remove your shirt”

Looking over at Rob with disdain, I just got it over with. We’d all seen each other in various stages of undress through the years, so this wasn’t a big deal at all, right?

Grabbing a hold of the top of the tight shirt, I pulled it up and over my head with no theatrics. I was now only wearing a tiny piece of thin white fabric, and I was all business.

Rob’s turn again, he again lined up his shot, and the ball sailed effortlessly into a pocket. I needed to do the same thing to stay alive, but I knew in my heart that I was about to be naked. As I shot the ball and missed, my hands were almost at my waistband until I heard the sound across the table. That ball that I’d missed earlier had been tapped unintentionally and fallen in, and as the guys started laughing, I was just relieved not to be hearing catcalls again.

Rob was back at it again, and I was standing opposite from him now, near the pocket that he was aiming at. Right before he released his pool cue, with everyone’s eyes on him and not me, I eased up an inch and rested my bulge on the table, right in his eyeline. His shot erred to the left, and I was acting normal again before anyone else noticed.

Catching my eye, he just gave me a wink as he untied the drawstring of his shorts and let them fall to the ground. Stepping out of them, we were tied up, each wearing nothing but our skivvies. He was wearing a tight, navy pair of trunks that framed his ass just right. His bulge up front was substantial, but he wasn’t aroused yet.

“Okay Ian, I’ve still got on socks as well, so for your next miss-”

“What if I don’t miss it?”

“-For your next miss, you can just tug your cute little briefs under that ass of yours.”

“I’m going to nail this shot just to prove you wrong now.”

As I lined up and aimed, I did not miraculously become good at pool- I still missed the ball. Hanging my head in shame, I knew that I was done for, and I just admitted defeat. Grabbing onto my waistband, I quickly slid them below my ass, giving a view to the peanut gallery beside me. I definitely didn’t have an ass like Charlie who once let it slip that he sent a picture to a fellow chef he was hooking up with a spice bottle balancing on the top of his bare ass as he stood up, but I had enough for the slightest of jiggles. I thought about turning around and jiggling my ass for Rob to distract him again, but he actually missed on his own this time.

He didn’t have as many good shots since he had less balls on the table, and this one veered right to the left of the hole. The catcalls were getting louder now, and he leaned down to reach for his socks until he heard me.

“Wait, I thought we got to choose what item each person took off?”

I was feigning an innocent expression now, and the smirk on his face was worth it.

“If you make me lose my underwear now, then you’ll regret it after your next loss.”

Looking down at the table, I realized that we hadn’t set any parameters. Would the game end once I lost my underwear? Even though that was a formality at this point, it still hadn’t stopped being any less humiliating. Would he make me dance? Bend over? Worse?

No, I couldn’t chance that, so I let him take off his socks as the guys, with John the loudest, started booing. As Rob threw the socks my way, I wondered if he’d actually be lenient on me once the game ended, but it turns out that my humility might have been for nothing. Once I missed on the next ball, Rob loudly yelled for me to lose my underwear. My friends were chanting loud enough for me to be glad that we didn’t have any cabins close by, but that unfortunately wasn’t close to being the biggest problem for me. As I stepped over to face them, hands over my crotch, there was no hiding that my bulge was bigger now than before.

I wasn’t fully hard yet, but the imminent exposure had caused me to chub up a bit, and I was panicking. I was stalling now, not even knowing what to do with my hands, when I finally grabbed onto the thin waistband and pushed my briefs down my thighs. My thick cock tumbled into view, and I was mortified- absolutely and irreversibly mortified.

We’d seen each other in college dorms and locker rooms, and we’d of course run into each other in states of undress accidentally when visiting. But this… this was a new level. I tried to cover up, but Rob, continuously making up the rules as he went, said I had to stay visible for three more seconds. Those three seconds took hours, but finally, I was able to cover up as Dennis and John scrambled to play a normal game next as I got dressed.

Falling into the couch beside Charlie, he just put his arm around me and gave me a squeeze. There were no words to be said, and even the drink that Rob brought me, who was still somehow only wearing his undies, would only help ease the embarrassment a bit.

I’d be fine after a good night’s sleep, and I could ham it up in the morning to diffuse it a bit, but I knew that this would be one of those core nights that came to me in memories for quite a while. If only I knew that this week was far from being over…