Poker Night Dares - Part 3

I have turned in my last assignment, which means that my posting schedule will finally be back to normal! Thank you so much for giving me a few weeks, but I'm ready to finish this series strong. I am having so much fin imagining what to make Conner do next, but in this installment, the focus is unfortunately all on me. VIPs, check out the content in the private Discord server to see that I'm wearing the exact same underwear that's mentioned below... and it's a bit revealing.

“You’re dead meat!”

Conner had finally gotten back inside, and he was blushing and fuming which had caused his whole body to turn red as he fumbled with his shirt to put it back on.

“You texted your neighbor to come outside and look at me?!”

“Absolutely not.” I was calm now as I’d obviously been preparing my response since I’d texted Tim. “I simply told him that I was playing some poker with a friend and to ignore any funny noises he might hear outside.”

“And the squeaky mailbox? You plan that too?”

“Seriously, Conner?” I definitely would have messed with it if I’d known that these dares were happening- I played every game to win and put my all in every time. “You think I’d do that?”

He said nothing, but as I smirked, he knew that he was right. I’d already shuffled, but he grabbed the deck to shuffle himself, which I obviously couldn’t blame him for. Dealing the cards, I saw that I had a great hand- three of a kind.

Laying them down on the table, I prepared to gloat until I saw that Conner had a straight. He’d barely gotten above a pair and a high card all night, and then he laid this down. His next hand was less impressive, but mine unfortunately was as well.

“Time for you to lose those pants, buddy.”

As I began to unzip my jeans, I jinxed myself by being relieved that he hadn’t made me get totally naked or forced me outside like I’d done to him.

“Wait, why are you wearing your grandfather’s underwear?”

Looking down, I saw some completely normal boxers showing through my undone fly.

“Fuck off- they’re comfortable.”

“They belong on a man who mainlines Metamucil every day. Go into your room, grab the naughtiest pair of underwear that you have, and come out wearing nothing else.”

“Fuck off!”

“Want me to go pick out a pair? Because if I do, and I just find those baggy boxers in your drawer, then I’m making you come out naked.”

“I can already see you getting hard at the thought of that.”

I thought I was just messing around with him, but right after I passed by the couch to walk upstairs, I missed him moving his hands in front of his crotch to cover himself a bit.

Heading into my bedroom, I unfortunately already knew what pair I’d be grabbing, but I prayed that I had something better. I normally wore boxers or boxer briefs every day, and I hoped that I could find some pair of briefs that an old hook-up had left behind, but there was nothing. Nothing except for the pair that I knew was in the back of the drawer.

It had been a bachelorette party for one of my friends, and the girls had decided to do a naughty underwear exchange to make the bride blush. I was the only guy there, and I had obviously not brought anything for this exchange. I thought I would just be able to clean up after dinner or top off champagne flutes for the girls, but there was a bag in my chair for me.

I was confused until the maid of honor winked at me, and I knew that she was the culprit behind all of this. I’d met Nicole my freshmen year of college even before I met Conner, and she’d been the one to introduce me to the bride a few years later. We were all friends now, but while Sarah, the bride, was prim and proper, Nicole was a proper slut in the most fun way.

“Okay Ian, let’s see what panties you’ve got!”

Sarah was champagne drunk now and getting into it, and to keep her happy, I pulled out an actual pair of panties from my bag. They were black mesh with white piping around the edge, and I kept turning them around hoping to find actual fabric, but there was none. The girls were hooting and hollering now, and I would have ended up wearing them right then and there if one of Sarah’s sisters hadn’t had the divine timing to run to the bathroom as the champagne finally caught up to her.

But now, after keeping them for all of these years, I was about to finally put them on. Praying that they wouldn’t fit, I slipped them over my legs and looked at myself in the mirror.

“What the fuck?!”

Conner:

I was beginning to wonder if Ian had crawled through his bedroom window to make a run for it, but then I finally heard him coming down the stairs. He walked into the room wearing those boxers again, and I was about to berate him until he slowly lowered the waistband. He was about to give me a show.

“Did you complete your dare?”

“As much as I wish I could say no… I did.”

“Then, let’s see.”

I’d had time to go soft, but I felt my cock growing in my boxer briefs again as he lowered those boxers. I’m blaming it on the bourbon because that’s a lot easier than trying to figure out if my best friend of over a decade is turning me on.

Ian kept lowering the waistband, and for a second, I wondered if he’d just decided to get naked without telling me, but then he finally tugged up on the tiniest little waistband to pull it into view.

“Well, what do we have here?”

As he leaned down to silently lower his boxers to the ground and stepped out of them, I took a second to pull my own boxers a few inches down from my waist to give my dick some extra breathing room.

Looking back up, I’m glad that I did because my friend was standing in front of me wearing nothing but a mesh pair of briefs that left nothing to the imagination. I could see his cock perfectly through the fabric, and he even spun around to show off his ass before sitting back down.

I was speechless, and he knew that. He was the one exposed, but he had the upper hand again, and he knew it.

This night was turning out differently than what I’d imagined, and for the first time so far, I wondered if I was ready for what was about to happen next…