Weekend Work Trip Pt. 01

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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. escort topkapı 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 escort kocaeli 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.”

I composed myself and took another small hit, holding it in before letting it all out and looking over the railing at the beach. I turned to hand the joint back to him. Mr Anderson lay on the long lounge chair, his rippling muscular body shimmering in the hot sun. He was wearing only a tiny powder blue speedo and I did my best not to let my eyes linger on the outline of his thick pronounced cock, bulging hard in the front pouch of his swimsuit. I felt my erection twitch involuntarily and tried to make small talk.

“So… when do we have to be at the conference?” I asked

Mr Anderson laughed again and flashed a goofy look. “Yeah… well as it turns out the conference has been canceled.”

“What do you mean?” I asked, confused. “But we came all the way here.”

He shrugged. “Yeah, who’d have thought? I mean, it happens all the time, it’s not a huge deal.”

“Well what does that mean for us?” I asked.

He smiled again, handing me the joint, “What that means is you and I have a whole day to do whatever we want.”

He passed the joint back to me as I tried to process this news. So what was the point of coming down here then? If the conference was canceled then this was all for nothing. I took another hit resulting in another coughing fit and I began to feel the weed’s effect.

“Man, you are terrible at that.” He laughed, taking the joint from me and motioning for me to come closer. He held it between his teeth and gripped my wrist, pulling me down to the lounge chair. Suddenly I was on my knees, straddling him, my smooth thighs around his. “Here… now lean in and inhale when I tell you.” He placed the joint backwards in his mouth, his hand caressed the back of my neck and he pulled me down until my lips were inches from his. Mr Anderson nodded and blew a thick stream into my mouth, I inhaled slowly. The smoke was much smoother this time and I pulled as much as I could into my lungs and held my breath as he released my neck. “Now hold it….” He said as I straightened up and tilted my head back. My head was swimming as the sensation of the weed took a hold of me, my body tingled as the warm druggy feeling washed over me. I was instantly stoned. I felt my cheeks flush and eyes narrow as he snubbed the joint out in the small ashtray on the table beside him. I felt his warm hand on my chest and slide slowly down my smooth stomach. “See? Isn’t that better?”

I nodded, relishing the swimmy sensation of the weed and my eyes focused back on him as his hands slipped over the thick erection bulging in my bikini briefs.

“Oh my!” He laughed, “What’s this?”

I blushed and stammered, “Oh, sorry! That’s… that’s because…”

“Shhhhhh…. It’s ok… I always get hard when I smoke weed too.”

I made a half hearted attempt to get up but his other hand held firmly on my hip as he caressed my throbbing bulge. He slid down slightly on the lounge chair and guided my body lower until my smooth lycra bulge pressed against his. He hadn’t been kidding, he was rock hard too.

“See?” He asked with a wide smile and I nodded slowly, staring into his blue eyes. We stayed frozen like that for a moment, looking at each other, feeling the pressure of our hard cocks pressed together as his hands held my hips. WIthout even thinking I began rocking my hips back and forth, slowly grinding my smooth bulge against his, my heart pounding through the druggy haze as waves of excited confusion raced through my body. It felt so good.

“Mmmmm….” He moaned as his thumbs slipped under the thin waistband of my tiny underwear, his hands gripping my smooth thighs as I rolled my pelvis against his. I placed my hands on his smooth muscular chest to steady myself, dizzy, confused and incredibly turned on.

“Yessss…. Thats good…” He whispered as he gently caressed my ass, pulling me closer to him, our hard smooth cocks separated only by the thin material of our skimpy briefs as they pressed together.

“I’m not gay.” I blurted out, instantly feeling embarrassed that I’d said that. “I mean… I’m not… I have a girlfriend…”

Mr Anderson smiled warmly, “That’s ok. I’m not gay either.” He said with a laugh, “And there’s nothing wrong with men appreciating each other’s bodies… is there?”

I shook my head, unable to speak as I pressed down harder on the shape of his hard cock.

“Straight women do things şişli escort bayan like this together all the time, ” he continued, his hand caressing my cheek before sliding it through my short brown hair. “And that doesn’t make them gay, does it?”

“N…no…” I mumbled, moaning softly as I arched my back, riding the wave of pleasure coursing through my body. I wasn’t sure I followed his logic but then a fantasy image of my girlfriend doing this exact thing with one of her female friends flashed through my mind and my shaved cock throbbed. His hands were on my back, guiding me closer to him as I gently humped against the shape of his massive erection. His lips planting small kisses on my smooth chest, then higher, kissing my neck, my cheek before taking my chin in his hand and kissing me deeply on the lips. I sucked lovingly on his tongue, melting into his kiss, shocked that I was giving in to this strange new sensation and making out with another guy.

“And why should girls get to have all the fun?” He whispered as his hands found their way back to my tight ass.

I moaned again as I kissed his neck, riding his cock as I submitted to this new desire. He held me close as I humped against him, the sun shining down on our smooth hairless bodies as I licked along his collarbone.

“Mmmm, look how hard you’ve made me!” He whispered and I leaned back, admiring the thick bulge in his tight swimsuit. He was so big, at least eight inches and even through the little speedo I could make out the shape of his thick head. Instinctively my fingers traced the outline of his hard cock and he let out a low moan. I was hypnotized by his hot bulge, unable to look away as I began to stroke him through his powder blue speedo.

“Yesssss….” He purred, “just like that…”

I stared into his eyes with pure lust, shocked that I was doing this but loving every second of it. He was right, there was nothing gay about two men appreciating each other like this. I mean… maybe a bit, but it was just…

Suddenly he spoke, breaking my train of thought.

“Do you want to kiss it?”

My mouth instantly began to water and I nodded. Yes. Suddenly out of nowhere, more than anything in the world I wanted to feel my lips against his hard cock. I kissed his lips again and then his chest, down his stomach, sliding lower on the lounge chair until my face was inches from his beautiful speedo bulge. My lips began kissing and massaging his shaft and head through the soft blue spandex as I wrapped my hands around his thighs. He ran his fingers through my shaggy hair as he moaned, “Yesss…. Just like that… good boy…”

Suddenly he reached down and pulled his tiny swimsuit to the side, his long shaved cock stood fully erect an inch from my lips.

“Do you want to taste it?” Mr Anderson asked and I nodded again.

“I’ve never done it before…” I whispered.

Mr Anderson smiled, “That’s ok baby… you know exactly what to do…”

He was right. In an instant I closed my lips around his thick engorged head, reveling in the sensation as his smooth fleshy thickness filled my mouth. He moaned again as I began swirling my tongue and pumping my lips up and down my boss’ big cock. It was so smooth and soft, so firm as my saliva coated his phallus and I worshipped him with my hungry mouth. It felt amazing. I felt so slutty, so horny, sucking Mr Anderson’s big dick had me more aroused than I’d ever been in my life. I suddenly understood why some people absolutely loved sucking cock and I knew that I’d forever be one of them from now on.

He held my head gently in his hands as I slurped and sucked, imagining what would feel good on my own hard cock, taking my time, alternately dragging my tongue over his smooth balls and shaft and sucking him deep into my throat. Judging by his moans of pleasure, I could tell I was doing a good job. I remember wondering if there had ever been a conference in the first place or if this was Mr Anderson’s plan all along, then realizing I didn’t care either way, lost in the joy of taking his big dick in and out of my wet slutty mouth.

“Such a good boy…” he moaned as I milked him with my mouth, “You love sucking Daddy’s big cock, don’t you?”

His words driving me wild with lust as I looked up at him, gasping for air.

“Yes…. Yes Daddy… I love your big cock…” I whimpered before diving back in, my eyes watering as I took him all the way into my throat. He began gently pumping his hips, softly fucking my mouth as I drooled down his smooth balls. I felt his hips pumping faster and I could tell he was getting close. My tongue became a fury of movement, massaging the underside of his cock head as I sucked harder, my lips stroking his shaft as he gripped my hair and inhaled sharply. His cock began to pulse and he let out a long moan, my mouth was suddenly flooded with his hot salty cum. I swallowed and continued sucking as his erection spasmed between my lips, each pulse accompanied by another spurt of sweet creamy cum. I tried desperately to swallow it all as his juice ran out of the corners of my mouth and coated my chin. Mr Anderson pulled my head from his big glistening cock and guided my mouth to his, kissing me hard, deeply, our tongues swirling his juice between our mouths before I collapsed in his muscular arms.

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