My boss is a big dude, and tonight I finally confirmed he’s big everywhere. Having only worked for John for a few months, I was still learning how the mild-mannered man managed to get everyone to do what he wanted all the time.
John’s company is relatively small at 15 employees, but the man paid well and demanded the world from those on his team. I thought it was odd that our only female was a vivacious, curvy Italian woman with big tits and bigger hair. While the only female employee, Audriana was a ball buster and the only person John backed down to. I often wondered how she had so much control over my boss, but I figured they probably fucked at some point and he still had the hots for the married mother of four.
I walked into the office on a Friday morning with my coffee and my gym bag and waved at Audriana as I passed by her big desk by the entrance as she told someone on the phone she needed four spots for tonight. Figuring she was making reservations for a double date later, I didn’t think anything of it and made my way to my desk outside John’s office.
“Jake, come in here please,” John’s voice carried from his office as I stood and entered.
“Morning, John,” I said holding my coffee as I stood at the side of his desk next to where he was sitting.
“Close the door,” he said gesturing toward the open solid wood door.
I closed the door and returned by John’s side. He finished typing and turned toward me on his swivel chair. His eyes didn’t hide the fact that he was looking at my bulge in my well-fitting khakis on this casual Friday. It was nothing new for John to openly stare at his male employees, but being a big guy, I figured he was always just super into fitness.
“Let’s have drinks after work today,” John said as his eyes finally met mine. “I want to get to know you better.”
I was a bit shocked. While John was always nice to me, he’d never seemed to give a shit about me or how I was liking my job. Hell, I knew I was making good money, so I had zero complaints about what I was doing.
“Sure thing, John,” I said taking a sip of my coffee while adjusting my crotch with my free hand.
I looked back at John and realized he was watching me rub my bulge. I guess I knew what I was doing on some level but wasn’t trying to seduce the guy or anything — it just happened.
“Paul and Adam are coming with us,” John said turning back to his computer screen as he now gave his bulge a good adjustment. “Be ready at 4.”
I walked to the door and opened it before John stopped me.
“Oh, and go ask Audriana for your bag,” John said without looking at me.
I walked to Audriana’s desk as she turned and looked at me while she filed her nails. She put the file down and bent down in her seat and pulled up a fancy black shopping back without anything on it. She put the bag on the top of her desk and picked her nail file back up without saying anything.
“Open it now?” I asked looking at her.
“Fuck, no,” she snapped at me as she scowled with a face that said you’re an idiot. “Don’t look in the bag until John tells you to look in the bag,” she said shrugging her shoulders like I wasn’t understanding basic math.
“What a bitch,” I said in my head as I walked back to my desk.
I passed Adam’s desk while he talked on his cell phone and noticed his black bag was on the floor under his desk next to his drawers. I followed his lead and did the same. The rest of the day was pretty busy but uneventful.
“You ready?” I heard John say behind me as I turned to see him standing there with Paul and Adam who were both holding their black bags.
“Yes,” I replied standing up and folding my laptop and putting it in my backpack.
I put my backpack on and bent to pick up my black bag before I felt John’s hand on my shoulder.
“Leave the backpack,” he said before walking to the door.
I dropped my backpack where the black bag had been and ran to catch up with the guys.
“Have a good weekend, Audriana,” John said without looking at her as he passed.
“Yep,” she said, “enjoy fellas.”
Her stare as we each passed her was moody and annoyed.
“Why is Audriana being such a bitch today?” Paul asked Adam ignoring me.
“No idea, bro, but she wouldn’t even look at me when I picked up my bag,” Adam responded.
We followed John’s big ass down the stairs a few flights until we reached the small lobby. He held the door for us and watched our asses as we each passed by. The three of us waited for John to tell us what we were doing.
“So none of you have gone for drinks with me in this smaller group yet, so I figured this would be a good group,” John said making eye contact with each of us.
“This guy’s been here for five minutes and already the invite?” Paul gestured at me without looking at me.
“Do you and your shitty attitude want to go back upstairs and finish the day in the office?” John asked.
“No, sir,” Paul said as he dropped his head like a child.
“Good,” Paul said putting an arm around me, “then let’s go have some drinks.”
My boss kept an arm around me for the rest of the block as the two idiots followed behind and watched quietly.
“You got a girlfriend?” John asked close to my face.
“Yeah,” I replied, “it’s pretty new though.”
“Mmmm, I bet,” John said as he let go of me with a smirk and bit his lip —something he does when he’s excited.
John took us to a bar I’d walked past a million times and never noticed. Hell, I’ll have to look again to see if there was even a sign. The place was dark with only a few groups of guys dressed in their casual Friday outfits. All eyes were on us as we stood at the bar and John ordered us beers.
“Cheers, guys,” John said as he went around and toasted with each one of us individually.
John moved us to a round high top table next to the bar. If there’s one thing I learned almost immediately it’s that the guys in the office can drink. While not a complete lightweight, I’m a complete amateur compared to these muscle heads.
“Oh yeah, you guys need to take your bags in the bathroom one at a time and come back,” John said as he handed out the new beers he’d ordered.
“I’ll go first,” Paul said bolting to the bathroom with his bag.
“Guess he needs to take a leak,” I said as Adam laughed and shot me a smile.
“You two hung out yet?” John asked looking at us both.”
“Not yet,” I replied as Adam and I made awkward eye contact.
“You will be after tonight,” John said before taking a gulp of his beer.
Just then Paul returned to the table holding his bag but looking the exact same.
“The fuck?” John said annoyed. “Leave the bags in the bathroom,” he remarked before handing Paul’s bag to me and gesturing that it was my turn to go to the bathroom.
I locked the stall door and quickly opened my bag. I had no clue what to expect, but I was like a kid at Christmas. I pulled out a small card in an envelope and read it.
“Put on the underwear in the bag. Leave your old underwear in the same bag. If needed, supplies are included for an enema. Leave your bag in the bathroom.”
Curious if Paul’s said the same, I opened his envelope and read it.
“Switch to this underwear and leave the plug in from this morning. Leave your bag in the bathroom.”
Now I was really confused. My mind was trying to make sense of the note as I pulled Paul’s used briefs from the bag and held them to my nose. Fuck, that jerk has the best smelling underwear I’ve ever perved. I remembered I needed to change and put on the white underwear that ended up being a mix between a jock and a thong. It felt good as I pulled the sexy underwear up my legs and pushed my huge package in the pouch.
Now, I should let you in a secret. While yes, I do have a sort of girlfriend that I’m dating, I’m bisexual— and a major cock whore. I left the rest of the stuff in the bag since I douched before work this morning and walked back to the table.
“All good?” John asked me with a smirk.
“All good,” I replied with my own smirk.
Adam gave me a look I couldn’t make heads or tails of before he jumped up and took his bag to the bathroom.
“I’m getting us more beers,” John said before hastily going to the bar.
Paul and I awkwardly sat at the table unsure what to say.
“You read my note, didn’t you?” Paul asked in a shitty tone.
“Fuck, yeah, I did,” I said before a smile spread across my face. “How can you function with a plug up your ass all day?” I asked with an amused tone and smile.
“Fuck you,” Paul said just as John returned with our beers.
John calmly looked at Paul and the two locked eyes. They almost seemed to have a conversation without saying a single word. John turned and looked at me before pulling me in for a side hug.
“This is fun,” John almost gushed as Paul now looked like he was about to cry.
“I’m having a great time,” I replied before putting my head on John’s shoulder for just a second.
”Fuck, you smell good,” John said to me like Paul want even there.
“All done,” Adam said as he was almost to the table.
We all turned to look at him before he blindsided me with a tight hug.
“I’m glad we get to hang,” Adam whispered to me before returning to his beer next to Paul.
Fuck, now I really wanted to know what Adam’s note said.
“Finish your beers and let’s head downstairs,” John said as we all chugged.
Paul and Adam both stood and the four of us looked around the table at each other.
“Let’s get to know each other and have some fun,” John smiled before walking toward the back of the bar as we followed closely.
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