My Best Work Trip Ever

It was Monday morning and I was dreading the start of another week. Work had been insane and I was starting to feel all the frustration and pressure of everyone relying on me to do their jobs. Even my boss was sending me out of town on a trip that he was supposed to take, but I tried to hope for a couple of relaxing evenings while I was gone. I’d never been to Portland before so at least I’d get to see someplace new.

I was already packed and ready to head to the airport for the morning flight. At least I had one day to travel and get settled with no work. I’d only be gone three nights but I almost wanted to call in sick for the whole thing.

The flight was boring and I was looking forward to getting to the hotel and getting settled. I got my bags and found the spot for the hotel shuttle.

As I was sitting on the bench waiting I noticed an older incredibly attractive stud of a man walk up to the waiting area. He had to be the sexiest man I had ever seen. I was usually only attracted to guys around my age, I was 26 at the time, and this man must have been the in his fifties. He just had such a masculine air about him and he looked ripped for a man of any age. His chest looked incredibly built under his jacket and had a buzzed head. Even his legs looked like they were muscular under his jeans. I couldn’t help it and my eyes wandered to check out his package. I could see the outline of his cock through his pants and it looked huge. I’m not exactly small and it looked as big as mine on my hardest day. I had been single for far too long, and my most recent fuck buddy moved away over three months ago. I probably could have found an easy hookup, but I had always preferred something with, at least a tiny bit of substance. Of course, feeling this way about it typically left me extremely horny and jerking off constantly.

I had sunglasses on, but his package was perfectly at my eye level, and I’d been missing cock for so long, my stare was very obvious. I think my jaw might have been a bit dropped as I was in awe.

“Beautiful day, isn’t it” I heard and it broke me from my trance.

“Oh, um yeah it is. Very nice.” I mumbled as his forwardness surprised me. “First time here, so I can’t complain.” I continued as I looked up at him.

Holy shit, he was so chiseled. His scruff was a light silver and his smile gave me that shiver of excited nervousness all through my body.

“Oh, very nice. I’ve been here a few times. It’s a cool place. Did you come for work or pleasure?” He asked.

“Work really, but I hope to find a bit of both since I have a couple of days to check things out,” I said

“I’m here for work for the week too,” he said “but it’s a fun city and I can usually find something fun to do while I’m here.”

I swear he had seen me checking out his package and his kind smile hid something that was becoming quickly obvious behind that wall of innuendo.

“That’s cool, any good suggestions for the downtown near the Hilton? That’s where I’m staying” I asked

“Good choice, that’s where I’m staying too.” He said as his smile slightly grew. “Always good brewery choices here, and we will be fairly close to the waterfront. You’re welcome to join me for a beer later if you have time, after all, we are staying close.”

“Oh that’d be cool, would be nice to kind of have a tour guide,” I said as the shuttle pulled up.

We were the only two waiting for that hotel shuttle and the driver got out to help us load our luggage. We got on and he picked a seat against the window. I wanted to keep talking with him so I sat across the center aisle from him and the driver headed out. The seats were all facing forward but he turned and put one knee up on the seat so he could face more towards me.

“I’m Tom by the way. So, what kind of beer does the younger crowd enjoy these days?” he asked as he turned and put one leg up on the seat next to him.

“Hey Tom, I’m Kevin. Seems like IPA’s are all the rage.” I said as I looked over.

His knee was up on the seat and he was turned to me so I could clearly see his package outline pressed against his jeans. Holy shit, his cock looked huge from that angle. It was long and against his leg and almost looked like it was uncomfortable being so restricted by his pants in that position. It was as if he was making a big effort to let me check it out again. I caught sight of it as I looked over and couldn’t help but linger there for an obvious second before I looked up and met his eyes. He noticed my paused stare at his cock and gave me a sly smile as our eyes met.

“IPA’s hmmm, I do see a lot of those around.” He said as he shifted in his seat and reached down to reposition his cock. I looked down as he did and he saw me follow his hand. My interest was now unspokenly clear to both of us. He left his hand on his cock and moved it through his pant leg as he watched me stare.

“Maybe we can even get you into something you haven’t tried before.” He said with a low slow confidence as he put his arm on the seat back and angled his bulge so I could see it even more.

Now that we both knew all the innuendo was clearly about his cock, I felt a nervous excitement well up inside me. I wanted him to take it out so I could see it right there on the shuttle.

“I’m game for something new,” I confirmed as our eyes met. “I’ve always wanted to try something that’s been aged perfectly.”

“You do look like you could learn to drink on a more mature level,” he responded.

The overtones had become pretty thick but we were both enjoying the banter, and now that there was no confusion about it, I was starting to get extremely excited.

“I definitely would like to, everything I’ve had so far has been more like young party beers. I’ve always wanted to try something with more depth.” I said.

He gave me a sly smile and said “I’m sure I could show you a few that would hit the spot.”

“I’m in for that,” I said, as I felt a surge of energy flow into my cock. “I haven’t even had a beer in months, much less something new,” I said. His look had intensified and I could feel his masculine energy starting to flow towards me from across the aisle.

“We need to fix that,” he said. “You should just come up to my room when we get to the hotel. I’m sure there will be something there to satisfy what you’ve been missing. A young man like yourself should enjoy himself more often.”

“I’m game for that, I’ve been thirsty for far too long,” I said as my excitement grew. It was a good thing I was sitting across from Tom and not closer, I wanted to feel his cock so bad I wouldn’t have been able to stop myself from touching him.

“Good,” he said with that dominance in his voice that sent chills of desire through my body. “We’re almost there, you’ll be able to quench that thirst soon.”

He moved his hand back down to his bulge and grabbed his cock as he said it. Of course, my eyes followed his hand and I gazed without apprehension as we both knew what lies ahead.

“How many nights are you staying?” He asked.

“Three, how about you?” I asked as he watched me stare at him running his fingers over his bulge.

“Perfect, I head out Thursday too. This should be an enjoyable week.” He said. “And we’re here.”

“Yeah, I think so too. I’m glad I ran into you,” I responded as we pulled into the hotel.

Thank god we had arrived. My anxiousness was on overdrive and my cock was pushing against everything to get loose. I finally looked away and tried to calm down so I could at least stand up.

“I agree,” he said as we got up.

Thank god I hadn’t got too excited to stand up, but I did have to reach in and shift things a bit as I stood. He watched me shove my hand down my pants and move my cock.

“We need to get those clothes off you soon.” He said as we moved to the door and stepped off.

“Thanks!” Tom said to the driver as we grabbed our bags and headed in.

“Anytime sir,” he said as Tom tipped him.

“That’s for both of us,” he told the driver as I added my thanks.

“Thank man,” I said to Tom as we got through the door.

“No problem, I got you covered,” he said with a smile.

I got checked in and took a seat in the lobby as I waited for Tom to go through the process. I couldn’t stop staring at this incredible man, I was so excited to see his cock I could barely breathe. He finished up and we headed to the elevator.

“What floor?” I asked as we stood next to each other. I was filled with anxious excitement about finally being this close to him.

“Seven. You?” He asked back.

“I’m on five”

“No, you’re on seven, with me.” He said with no hesitation as he grabbed my ass.

“We’ll go dump the luggage and I’ll take you to get something to eat. I’m getting hungry.”

I sighed slowly with relief as I felt his touch. His hand felt big and strong and my ass fit snugly in his palm as he squeezed my cheek. I felt like total putty as his masculine aura engulfed me with that first touch. I had loved sucking cock and being fucked for a few years now. Ever since the first guy I was with I knew I had been made to please other men. Nothing made me feel better, but the comment I made earlier about the young beers was true. I had only ever been with young guys that fucked like rabbits. As I stood next to Tom with his hand on my ass I knew this was going to be completely different. This wasn’t going to be some horny boy I was just getting off for fun. I was going to learn what it truly means to please a man.

As we reached our floor he gave my ass a last hard squeeze before the door opened. I followed him down the hall to his room and we went in. His calm slow deliberate manner was intoxicating. I was almost shaking in anticipation as he slowly took my bag from me and put our luggage on the floor. Then he put his hand around my neck and gently pulled me in, the calm forceful kiss made my body start to feel weak. His lips were strong against mine and his light scruff felt amazing. Our lips began to open at the same time and I felt his strength even deeper as his tongue entered my mouth. The way he kissed me reinforced how different this sexy older man was from any of the boys I had been with before. His powerful dominance made me feel safe and excited to please him. He kissed me with such mature authority, it made me start to softly moan with pleasure.

He moved his hand from my neck, grabbed my ass on each side, and pulled me up just a bit off the floor as his tongue dove deeper into my mouth. I wrapped my arms around his torso and opened my mouth wide to let him have his way. He let out a low moan as we both knew I was his for the taking.

He released me back to support myself and my knees almost gave out as he pulled my shirt up over my head. He threw it to the side and grabbed my ass as he dove back into another deep kiss. I started to pull his shirt up and he raised his arms, grabbed it, and ripped it off himself. His chest was perfect. His strong pecs and his abs were incredibly defined for an older guy, I was so fucking turned on by how sexy this man was. My cock had swelled and was pressing hard in my pants.

We continued kissing as he reached down, unhooked my belt, and pushed my pants to the ground. My cock was rock hard as the air hit my ass cheeks. I had switched to only wearing jocks about a year ago, once I had discovered how much I liked being fucked it just made sense. Plus I liked how every guy that had fucked me since I switched loved how sexy my ass looked in them. He felt my bare ass in his hands and growled with approval as he grabbed it hard and unleashed another passionate wave in my mouth with his tongue.

I finally let myself feel his bulge through his pants and I grabbed for his cock. I could feel it getting hard and started to undo his belt. He pulled back from our kiss and let me watch as his pants fell to the ground. His cock looked enormous through his black boxer briefs. I rubbed it through the material as I gazed and I could tell he smiled watching my excitement grow.

“Go on,” he said, nodding in permission to do what we both knew I was thinking.

I immediately dropped to my knees and pulled his boxers down to the floor. His huge cock flopped out and I took a second to just look at it. He was only semi-hard and it was hanging down just below my chin. He stepped out of his underwear and spread his stance just a bit. I lowered my head just enough to reach out with my tongue and bring his cock head into my mouth. It was amazing, his cock filled my mouth as I started to run my tongue along it. I got about halfway down then closed my lips around his shaft and lightly sucked.

“Oh fuck,” I heard him say as his hand ran down the back of my head. His fingers sliced through my hair as I slid my lips further down his shaft and took more of his cock deeper into my mouth. I grabbed his thighs to brace myself as I pushed my head onto his huge cock. I was glad I had worked on my gag reflex, his was easily the biggest cock I had ever sucked but I was still able to get my lips down to the base. He was still getting harder as I started to move my head up and down his cock.

“Ahhhh, yeah boy. Suck that cock.” He moaned as I started to find my rhythm.

“Not too fast,” he added as he put his hands on both sides of my head to control the speed. He held my head in place as he started to fuck my mouth. His rhythm was slower than I was used to, and I could feel the confident control of his movements.

I could feel his cock continuing to grow as he slowly fucked my face. His breathing was becoming deeper and I could hear a faint “fuuuuccckk” as he enjoyed my mouth. He had grown too large and I couldn’t reach my lips to the base any longer. He pushed his cock deep with one thrust and I gagged just a bit.

“Don’t worry, you have impressive skills already,” he said as he backed off just a bit. He became even more controlled and pulled back so his head was just inside my mouth.

“Now relax,” he said, as his cock drove down my throat again. I don’t know what he changed, but he held my head and slowly maneuvered his cock all the way in. I held my breath as he kept it there for a moment before pulling back.

“There you go. Knew you could do it.” He said in encouragement. I felt the satisfaction of his approval and I loved knowing I could suck his enormous dick. He pulled his now fully erect cock from my mouth and I saw what I had just taken. His cock was perfect. Big and thick I loved it being right in front of me and I reached forward to suck the tip again. He could see how eager I was for more and he said “Come here” as he walked over to the recliner. He sat down with his pole of a cock reaching toward the ceiling. I stayed on my knees and made my way over to him. I loved feeling subservient to this incredible stud, I couldn’t wait to make him cum and now I knew better how he liked to be sucked.

I got the chair and ran my hands up his muscular thighs. He spread his legs a bit further apart and leaned back with his arms on the chair in relaxation as I started to suck him again. I loved that he just sat back and let me enjoy his dick. I slowly slid my lips down his shaft and felt his trimmed pubes brush my lips as I took his entire cock. I felt empowered now, being able to feel his pole. I moved my head up and down his cock as he started to moan more loudly.

“Ahhh, fuck yes, suck me” he moaned as started to aggressively make out with his cock. His hips began to move a bit as he was getting into it, and I started to taste his precum on my tongue.

He took my head again and controlled my pace once again, this time moving it up and down his cock as he pleased.

“Fuck, just like that, that’s perfect.” He said as he made my mouth ride his dick.

I was so hard that I reached down and let my cock out of the jock. The relief felt amazing as I couldn’t get enough of his dick.

I started to stroke myself as he went back to holding my head still and thrusting his cock up into my waiting mouth. He was starting to thrust more deeply and got more vocal as his orgasm neared.

“Ahhh boy, suck that cock, fuck yes,” he said louder as his precum continued to flow. I had to sneak in a swallow and almost thought he had already cum with how much there was. It was turning me on so much to be bringing this man such pleasure.

“Oh yes, here it comes, drink it down, boy.” He said as he controlled his last few thrusts.

He growled deeply as his cum filled my mouth. My cock exploded as soon as I tasted his load. It filled my mouth before I could swallow and some leaked down his shaft. I drank his cum as he continued to fill my mouth with more.

“Fuck yes, eat it” he ordered as he watched me struggle to swallow it all.

I had never had a load fill my mouth at the same time I came myself and the pleasure was overwhelming. I loved the taste of his cum and as his organs subsided I kept some in my mouth for a moment before swallowing it all.

“God damn, what a mouth.” He said as his cock left it. I licked the spilled cum off his perfect shaft as he watched. “Yeah, get it all, lick me clean.”

I gave his cock a lick from the base up to the tip. He watched and then sat back and let me enjoy getting every drop of his cum. I took his cock back in my mouth a couple of times as it relaxed. He finally leaned forward and kissed me deeply and I pulled my jock up over my cock.

“Good work Kevin.” He said as I got up.

“Your cock is perfect,” I mumbled as I wandered around looking for my pants.

“And it’s only been in your mouth so far. I can’t wait to fuck your hot young ass next. Let’s go get some food and that beer, then I’ll try not to keep you up all night.” He said as he smiled.

He stood up and found his clothes, came over, and kissed me. Then he brought my head to his nipple and I sucked it.

“Good” he sighed “we’re gonna have fun tonight.”

We slipped our shirts back on and he spanked my ass as we left the room. This had started to be such a shitty day and now I had just sucked the best cock ever. I couldn’t wait to take his dick and feel him fuck me later that evening.