Casual Friday (Patreon)

It's time to wrap up this series (check it out under the Collections tab in the top menu) for now, but I can see myself revisiting these guys later. Until then, check out what Trent has cooked up this Friday... 

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“Morning, Austin.”

“Morning, Noah.”

To the people at the desks near us, our greetings seemed completely normal, but they couldn’t see the smirks on our faces. For the past few days, we’d been getting extra stares as everyone saw us in our new underwear. When Austin put a new ream of paper into the copier yesterday wearing his jockstrap, Ben had fallen straight out of his chair as he leaned over to stare. The rest of this morning went a little something like that as well, but this afternoon… it would be different.

“Hello everyone, I thought I’d give a quick announcement now that we’re back from lunch.” Trent was standing right in front of our desks as he waited for everyone to quiet down. “As most of you have noticed, my assistants have been sporting some new workplace attire, and they seem to be getting positive reviews. I think that means that a change should be in order.”

Everyone’s attention was now piqued as they waited to see what Trent would say. Was he about to make us strip off our suit coats and shirts to wear nothing but ties and a thong? Would we ditch our underwear altogether?

“Starting appropriately today, I think it’s a great idea to celebrate Casual Friday!”

Trent just stood there with his arms outstretched in front of him waiting for applause, but he hadn’t been clear enough.

“Ben, come on up here.”

He eagerly got up and walked over, but he probably would have slowed down a bit if he truly realized what he’d been volunteered for. As he stood there with Trent’s arms around his shoulder, I could see him basking in his boss’s aura of expensive cologne and undeniable sex appeal.

“I’ll let you be the first volunteer for Casual Friday- go ahead and strip those pants off for us.”

“Wait, what?”

There were gasps around the room as Ben’s face turned the same shade of red as the fabric covering my cock right now. Everyone had assumed that Casual Friday would be for Austin and I- they never thought that they’d be getting in on it as well.

“I, uh-” Ben was stammering now, trying to find some way to save himself, but his normal stream of words just wasn’t coming to him.

“You seemed to love Austin’s outfit yesterday, so it seemed natural that you wanted that same freedom in the office. Don’t ruin this for me, Ben.”

Trent tightened his grip just a little on his subordinate’s shoulder, and that sent the message loud and clear. He wasn’t asking- he was demanding. And he wouldn’t say it again.

Stepping free, Ben began to unbuckle his belt with shaking hands, and the room was silent enough for everyone to hear the metal hit against his watch in the process. As he pulled his fly down, his phone and wallet in his pocket finished the job he couldn’t do as his pants fell to his ankles. His shirt wasn’t as short as mine, so he was still mostly safe until Trent decided to pull it up for Ben. He revealed a normal, if not a little tight, pair of white Calvin Klein briefs with a trail of hair leading up his tight chest. His bulge was covered at first by his hands until they were swatted away by Trent.

As Ben awkwardly grabbed a chair to pull his pants over his shoes, Trent kept calling up name after name to get the ball rolling. Some of the guys started stripping at their own desks to save themselves the ridicule, but others couldn’t force themselves to do it. One by one, they were brought up by Trent for some motivation of his own.

“More boxer briefs?”

I could tell that Trent had been expecting something exciting after that initial pair of briefs, but he’d gotten three men wearing conservative boxer briefs, one after another. The dark fabric hid any semblance of a bulge, and he was ready for some fun.

“Marcus, you’re next!”

Marcus was Spanish, and he visited his family back home often. He’d post pictures of him and his sexy brother-in-law on the beach in tiny speedos surrounded by other sexy men in tinier speedos. Trent was betting on something just as skimpy as he instructed him to pull down his pants, but he was met with a pair of blue plaid boxers.

“What the fuck, man?” He spun the graphic designer around to face his covered ass to the office space. “Why are you hiding this ass behind that underwear?”

Before Marcus could even answer, Trent had grabbed ahold of the fabric and yanked it down past his thick thighs. His tanned, exposed ass was on display for everyone, and on his other side, Austin and I caught a view of that uncut cock before his hands jumped into action to cover himself. Without a word, he waddled quickly back to his desk with one hand on his growing cock, the other on his ass, and his pants around his ankles.

As Trent surveyed the room, he saw that his plan had worked. All of the men standing to watch were in their underwear, and he couldn’t wait to do performance checks later and get close looks at them as well. One noticeable exception was Brent who seemed to be quiet for the first time in his life as he sat hunched over at his work station. It looked like he was pretending to be above it all, but that couldn’t be further from the truth.

“Brent, it looks like you’re our last volunteer!”

“Sorry boss, I just need to finish this before end of day so I’ll catch you next Friday.”

“I wasn’t asking- I was telling you.”

The noticeable hush made it quiet enough for everyone to hear Brent sarcastically say that he shouldn’t have said volunteer then, but he did get up and walk over, albeit as slowly as possible. He looked taller than normal as he stood next to Trent, and the latter man took great pride in knowing that he was about to take his employee down a few pegs. He leaned casually against my desk, close enough for me to reach forward and palm his impressive ass, but I contained myself. Well, at least I contained my composure… my cock was already stretching the limits of this thong, and I was thankful that Reginald had constructed it himself out of the highest quality materials to keep the seams from snapping.

“You know what to do, Brent.”

He grumbled out some other statement, but no one could hear it or cared to try. They were here for one thing only. Brent pulled open his belt and made a great show of whipping it from around his waist to try and make him seem braver than he was. That act was given up immediately though when he couldn’t force himself to pull down his pants after unzipping them, and we all waited about ten seconds before he finally let go. They hit the floor, and I could see people in the audience craning their heads to get a view of what was hiding under his long shirt. We could see an impressive pair of muscular thighs, but no fabric.

“See folks, this is the style of underwear that I want to see next week- none of those boxers that your grandfathers wore. Go out and buy some like these.” Trent suddenly pulled Brent’s shirt up, and he wasn’t fast enough to cover himself. That gave all of us a view of the “underwear” that Trent had been complimenting.

As laughter rang out, Trent finally looked down to see that Brent had been going commando, and his dick was hanging there for everyone to see. His thick bush dwarfed his cock a bit, but he soon started getting harder to compensate even though he clearly didn’t want to. He was a big guy, but Trent was stronger, and he couldn’t get out of his boss’s grasp. Trent held him there with one arm as the other lifted up his shirt past his nipples to make sure that everyone could see the once cocky man completely exposed.

Trying to get free, he just accomplished getting himself more aroused as his cock wiggled around under the bright fluorescent lights. Nervous sweat began to make his body glisten, and once Trent let go, he practically ran to his desk, tripping on his pants in the process. His meaty ass was now on display as he fell to the ground, and it seemed to ricochet upon contact. Getting up, he grabbed his pants in one hand and ran past his desk right towards the elevator.

“Well, that’s all the show that we’re getting today. Get back to work!”

And with that, Trent took his own sizable bulge back into his office to take care of, leaving Austin and I to relish in the situation. Their exposure didn’t make us any less naked, but it sure made it a lot more enjoyable.