Part 1 of 3.
FRIDAY.
I was honestly surprised that my boss, Mr. Anderson even knew my name. I'd only been working at the company for a few weeks at that point and I hadn't really made much of an impression yet.
"Are you available to work this weekend, Aaron?" He asked as he leaned over my cubicle wall.
Mr. Anderson was in his mid forties, tall, clean shaven with short greying blond hair. I nodded without thinking, eager to please as this was my first "real" job after graduating. I was sure he wanted me to work on the massive data entry project that me and my fellow office drones had barely made a dent in.
"No weekend plans or anything?" He asked.
"Nope. I'm free. Do you need me to work on all this data entry?" Patting the large stack of papers beside my keyboard.
He smiled, "No it's something else. I've got a conference to attend and my assistant Bryan won't be available. I need you to fill in for him, is that ok? We'll be back on Sunday."
"Sure!" I blurted out, excited to prove myself and show that I was able to rise to new tasks.
"Great! We leave right after work, our flight is at seven."
"Wait, flight?" I asked confused.
"Yes," he said, taking a sip from his coffee cup, "The conference is in Miami. That's not a problem is it?"
"Oh...no. It's not a problem... but I should go home and pack a bag first?"
"Naah, don't worry about all that." He said with a smirk, "Bryan will set you up with everything you need. Meet me down front at five fifteen, ok?"
I nodded and he rapped his knuckles on the wall of my cubicle before turning and heading back to his office.
Ok then. I was excited although a bit nervous to go on an impromptu trip to Miami with Mr. Anderson. Even though I was sure I'd just be fetching coffee and shuffling papers in a hotel conference room all weekend I was picturing how awkward it could be to spend two days working closely with my boss. I texted my girlfriend and told her the news, asking her if she thought any of this seemed strange. She was happy for me and pointed out that this was a great opportunity to prove myself to the higher ups at the company. I realized she was right and my nervousness subsided. It was a bit odd that he didn't want me to pack anything though but as he said, Bryan would make sure I had everything I needed.
At 5:15 I stood waiting out in front of the building as Mr Anderson exited through the glass revolving door carrying a medium sized brown leather overnight bag. "All set?" He asked as a long black sedan pulled up and we climbed inside. As we sped to the airport he handed me my boarding pass and thanked me for stepping in at such short notice. "Usually Bryan comes with me on these things but he has family visiting this weekend," He explained, "And don't worry, it won't be anything horrible, I'm sure you'll be able to handle everything." He laughed and patted my knee.
The plane took off precisely on time. I'd never flown in first class before and after making small talk with Mr. Anderson and downing three glasses of champagne I fell asleep, waking only when the plane jerked as we touched down in Miami. It was dark out and incredibly humid as we made our way to the cab stand and another black sedan whisked us to the hotel. We pulled up at a swanky resort with a huge magnificently appointed lobby. There was a large outdoor pool adorned with palm trees and private beach access for the guests. The clerk checked us in and as we rode the elevator up to our floor Mr Anderson apologized that we'd be sharing a room. "Everything was so last minute..." He explained, "There was only one room available." I understood but felt nervous again as I realized we'd be spending more time together than I'd previously expected.
The "room" was actually a massive suite on one of the the top floors of the hotel. There was a large roof deck, living room with a white leather sofa and a giant king sized bed. Mr. Anderson walked in surveying the room and setting his bag down on the bed. He looked at his watch. "Wow, I didn't realize it'd be so late. I'm gonna get a quick shower, why don't you check out the room a bit." He closed the bathroom door behind him and I heard the shower turn on. I made my way out onto the roof deck, taking in the incredible ocean front view and feeling the night air on my skin. I texted my girlfriend to tell her we'd arrived and she wished me good luck before bidding me goodnight. I heard the bathroom door open and Mr. Anderson stepped out wearing only a tiny pair of black string bikini briefs, his toned muscular arms and chest shimmering from the moisture of the shower as he toweled off his hair.
"I left you some hot water. And something to sleep in on the counter." I felt the need to look away as he spoke. "Make sure you leave your work clothes out here so I can send them out to be dry cleaned." He tossed the towel into the hamper and hopped onto the bed, clicking the tv on.
Okaaaaaaay... I thought as I entered the bathroom and closed the door. Mr. Anderson was obviously very open with his body, kind of strange. Or not. Maybe this was how people were? Maybe it's normal to walk around partially naked with another guy in the room. The sight of him in only his tight underwear flashed in my mind as I disrobed and dropped my boxers, pants and dress shirt on the floor outside the bathroom before turning on the water and getting into the shower.
I shut off the faucet and toweled off before looking to see what Mr. Anderson had brought for me to sleep in. On the counter was a tiny pair of new stretchy black string bikini briefs with the shop tags still attached. They were the exact same style as the pair he was wearing. For the second time an image of his thick bulge flashed in my mind. My heart raced. I 'd never worn anything this skimpy before, and certainly not around another guy. I only ever wore baggy boxer shorts but these were incredibly small and I ventured to think, slutty. Maybe he was kidding, like this was a way to break the ice between us or... not? Did he really expect me to wear these? I cracked the door to grab my boxers but they were gone, off to the laundry service I assumed. My heart sank. My only options were to put on the tiny briefs or wear my towel. But that would be strange, I couldn't sleep in a towel.
I sighed and stepped into the tiny briefs and slid them up my legs, pulling them up over my hips. Oh my... I thought. They felt incredible. The tight stretchy material hugging the curves of my hips and holding my thickening cock snugly in the tight front pouch. I looked at my reflection in the large mirror and was glad that my girlfriend had got me into shaving my body completely smooth. I marveled at how I looked, the briefs gripping the curves of my ass, the impossibly thin side straps directing attention down to my hard smooth bulge, the dark material in stark contrast to my pale skin. I looked hot. I snapped the tags from the waistband and took a deep breath as I flipped off the light and stepped out into the room.
Mr Anderson looked up from the tv. "How was the shower?" He asked.
"Good." I mumbled. " I needed that..."
"Yeah, it always feels good after a flight." He gestured to my underwear, "How do those fit? Bryan wasn't sure about your size but I think he nailed it."
"Yeah... they fit good..." I said, not sure where to place my hands or if I should cover myself and my obvious erection. I pointed to the sofa. "Is that me?"
"What? Come on..." Mr Anderson laughed and patted the opposite side of the bed, "I'm not gonna make you sleep on the couch. There's plenty of room up here. Unless that's weird. You can take the couch if you want."
"No..." I stammered, blushing, "No that's cool..." My heart was pounding. Did he really expect me to sleep in the same bed as him? With both of us wearing these tiny "man-panties"? I didn't want to be rude. I felt my shaved cock throb and my stomach flutter as I rounded the bed to my side and slipped under the covers.
"There. See?" He laughed again, "That's much better than the couch. And don't worry, I don't bite."
It was my turn to laugh, realizing I didn't have anything to worry about and the bed was incredibly comfortable. Plus Mr. Anderson wasn't gay. I'd seen his wife stop by the office on numerous occasions and they were very affectionate with each other. Being nervous was silly, I thought as he flipped off the light leaving the room to be lit only by the glow of the tv. I rolled over with my back to him and closed my eyes.
"Get a good night's sleep," He said as I drifted off. "We have a big day tomorrow..."
SATURDAY MORNING.
When I opened my eyes the room was pitch black aside from the sliver of white light coming from the cracked doorway to the roof deck. I was alone in the bed and immediately aware of my massive erection. My dreams had been intense, highly sexual but unfocused. I seemed to have a vague memory of feeling Mr Anderson's body pressed against mine, his breath on my neck as he wrapped his arms around me, grinding his hips into mine as I moaned and he stroked my cock... but that must have been part of the dream. RIght? It couldn't have been real. I wiped the sleep from my eyes and sat up, taking in the strange room in the half light. No, I thought, that didn't happen. It couldn't have. I was just horny from the tight underwear I was wearing and the sight of Mr Anderson in his sexy briefs had worked its way into my subconscious somehow. That must have been it, I told myself.
I stepped into the bathroom and splashed water on my face before brushing my teeth. I looked around for something else to put on but there was nothing. I shrugged and flipped off the light before making my way out onto the deck wearing only my tight little bikini briefs and for some reason still bulging hard. The door swung open and I was hit in the face by the strong smell of marijuana. Mr Anderson turned to greet me, a wide smile on his face as he blew out a huge plume of skunky white smoke.
"Well there he is..." Mr Anderson laughed, "How did you sleep?"
"Good..." I said squinting in the bright morning light and attempting to cover my bulge. "Just a bit groggy..."
"Here." He said handing me the joint, "This'll help with all that."
I laughed and took the joint, holding it to my lips and inhaling deeply. The thick smoke burned my throat and I started coughing. He laughed, "Ha ha, yeah that stuff is pretty strong... I should have warned you."
