Orlando Business Trip to Remember

Part 1

A sliver of light shown through the blackout curtains. Waking up naked and flat on my back I quickly looked around the room, finally awake enough to remember where I was: in a hotel in Orlando. In a mental fog, I crawled out of the bed and made my way to the bathroom. As I walked the short distance I suddenly realized that my ass was sore as hell, and then I felt something beginning to run down my legs. 

After showering and throwing on some shorts, a T-shirt, and flip-flops, I headed out of the room. I desperately needed some coffee. The truth was I was confused and yes, afraid. I was in the midst of some sort of amnesia. I had hoped some caffeine would bring some clarity to what had taken place in that room and on that bed. But I did’t know if I really wanted to remember!

While taking the elevator to the lobby I replayed in my mind the night before. I had left Chicago for a business meeting. I arrived late in Orlando. Because of bad weather I had missed my connecting flight in Atlanta. Fortunately, I was able to get a later flight. After getting checked in at the hotel, I headed straight to the bar. I needed a stiff drink to relax after a stressful trip. Evidently, I must have had one too many Jack Daniels on the rocks, because as hard as I tried, that’s all I could remember of the previous night.

Getting off of the elevator I entered the hotel restaurant and looked for table. It was Spring Break and the place was packed. I saw families with little children there to visit Disneyworld and college-aged kids there to party at the nearby beaches. I sat at a table in the corner, facing the whole room. I downed a cup of coffee and asked for another; I didn’t know if I could stomach any food. Hearing a commotion I looked up to see a family being led to the table directly across from mine: a husband, a very pregnant wife, and two toddlers. Accompanying them were what appeared to be the grandparents. The husband sat directly in my view. I made eye contact with him. He smiled at me, and then he quickly looked away. Holy shit. That smile . . . Mr. Man-of-Few-Words! A piece of the puzzle fell into place. I remembered him from the night before: 

* * *

As I sat there at the bar he had approached and sat one stool away from me. He ordered a beer and made small talk with the bartender. He was hot! I tried not to be too obvious but I couldn’t help checking him out. He was masculinity personified. Looked like he was in his early thirties. He was around 5.8” tall, with dark brown hair and a neatly trimmed beard. He was wearing a loose tank top, board shorts, and a Chicago Cubs ball cap on backwards. He looked like he was a regular at a gym. Tattoos covered his muscular shoulders. Every now and then he would look my way. I finally smiled and gave him a wink. Nothing gained nothing lost. But I got no reaction out of him. In fact, after that he avoided looking in my direction. 

I decided to call it a night. I got up to leave and as I turned away from the bar he made eye contact, talking to me with his eyes, or so I hoped. On the way out of the bar I headed to the restroom to take a quick piss. Feeling relief after I had emptied my bladder I turned to leave. The door swung open and in he walked. Wasting no time he came right up to me and looked straight into my eyes. If ever I had seen the look of lust he sure had it. He quickly grabbed the back of my head and planted his lips on mine and jammed his tongue into my mouth. While passionately kissing me, he had his other hand on my dick, which I didn’t have time to tuck away. He dropped to his knees, pulled my pants down, and took my cock into his mouth. Even though I had quite a bit to drink my dick sprang to life and I immediately became hard as a rock. The guy went absolutely wild. Licking the head and sides of my penis, he positioned himself to get my balls into his slobbering mouth. He then stuck a finger up my ass as he deep throated me. Unfortunately, I quickly lost control. I took the back of his head into my hands and began pumping my hot cum into his mouth. He sucked even harder and when he finally pulled off he lovingly licked me clean. If ever there was a cock worshipper this guy certainly was one! And as quickly as it started it was over. He stood up, gave me a kiss, sticking his cum coated tongue into my mouth. He stared into my eyes and smiled. “Thank you. I needed that,” he said, and was out the door.

* * *

And now less then eight hours later there he was sitting at the table with his wife on one side and his mother on the other, surrounded by the rest of his beautiful family. If only they knew! I took one more swallow of my coffee, threw cash on the table for my tab, and made my way past his table. I paused to say hello to them and told them I hoped they were enjoying their stay in Orlando and asked how long they would be staying. Dared I hope for a repeat of the night before? 

I made my way to the restroom and entered one of the stalls, leaving the door partly opened. With my shorts and briefs down and my cock a full mast I patiently waited. And sure enough I heard someone enter and footsteps came my way. There he was, with that same lustful look in his eyes. But this time I wasn’t drunk and I decided to make him work for it. Dropping to his knees in front of me, he grabbed my ass and pulled my crotch into his face. Hands free he quickly went down on me. He kept deep throating me and gagging himself multiple times. It was becoming an extremely sloppy blow job, saliva drooling down his beard. He looked up at me with his dark brown eyes, pleading with me to give him what he wanted so badly. Not wanting it to end, I finally gave in and let loose multiple shots of my seed down his throat. Finished, he wiped the tears out of his eyes and the remnants of cum off his chin and beard. With his appetite satisfied, he quickly got off his knees, and with that smile on his face, left me standing there with my shorts at my feet. Out the door he went, without even a thank-you this time.

I walked through the restaurant on the way to the elevator. I looked back and saw Mr. Man-of-Few-Words back at the table with his family. I thought, “Wow, what a business trip this is turning out to be.” But then I had fleeting feelings of guilt, and even sadness for him and for his family.

As I rode the elevator back to my floor I knew the real question remained unanswered: “What the hell took place last night on my bed?” 

Part 2

It was a beautiful Orlando day and since I didn’t have any business meetings until the evening I decided to go to the pool and enjoy the sun (and the view of any hot guys who might be sunning themselves). I put on my favorite skimpy red speedo, wrapped a towel around my waist, and headed down to the pool. I was happy to see that there weren’t any annoying kids in the pool shouting “Marco Polo.” In fact, the pool area was just about empty being that it was still early in the day.  I stretched out on a lounge chair, plugged in my ear phones, and put on my sunglasses. Because I didn’t get much sleep the night before (God only knows why) I promptly fell asleep. 

I don’t know how long I had slept before I was rudely awakened by loud shouts and splashing of water in the pool. I sat up to see six guys throwing a ball around. A bunch of frat guys, jumping up and down in the water, grabbing at each other; a super abundance of testosterone, a gay man’s wet dream. One guy in particular got my attention as he got out of the pool right in front of me. His tight swimming suit was clinging to his toned body and I couldn’t keep my eyes off his bulge. Suddenly, my eyes focused on to something that appeared very familiar to me: a tattoo of a smiley face peeking out from the top of his swim suit. I looked up at him and he grinned, turned around, shook his butt at me, and jumped back into the pool. Just that quickly the memories of the previous night started flooding back: 

* * *

Returning to my room that night after the first encounter with Mr. Man-of-Few-Words, I was too wired to go to sleep. After tossing and turning in bed, I finally had decided to get up for a while. I grabbed my bottle of Jack Daniels (which I always travel with) and poured myself a generous drink. It was past 2 a.m. and after one too many drinks I picked up my phone and began to surf the net. Finding nothing interesting, for the hell of it I clicked on the Grindr app. To my surprise I had a message from someone 0 feet away from my room, “Hey, let’s fuck.”

There wasn’t any photo, just a smiley face emoji. But his profile stated: “19, 6’4”, bicurious, very discrete, athletic.” I responded immediately with “Where you at.” He answered, “Room 708. Can’t host.” “LOL,” I replied.  “You’re in a room down the hall from mine! Come out into the hallway. I’ll meet you.” I opened the door and looked down the hallway. A door opened and a tall young guy came out and very quietly closed the door behind him. I couldn’t believe my eyes. He was stark naked with just a backpack slung over his shoulders! Seeing me, he slowly walked in my direction. His cock stood straight out as if pointing the way. I was certain he was checking me out and deciding whether or not to keep coming or to turn around and head back. Although I was around 20 years older than him with some grey in my beard and hair, he kept walking toward me. I opened the door all the way and he entered without hesitating. 

He had a smooth, lean, swimmer’s body and he had blue eyes and blond hair. He had one tattoo: that of the smiley face emoji just between his belly button and his shaved pubes. Looking at him I could sense that he was very nervous. I put my hand on his shoulder and told him to relax. He smiled a little, dropped the backpack on the floor, and then walked over to the bed. My mind was racing. “What should I do?” I asked myself. He answered that question for me. 

Suddenly, he grabbed my head with both hands and pushed me down on to my knees and forced my face into his crotch. The message was clear. He was in charge and he knew exactly what he wanted. As I breathed in his manly scent, his beautiful, large, uncut cock, that was already dripping with precum, slapped me in the face. I looked up into his eyes and then took the tip of his cock into my mouth and swirled my tongue around it. But he was having none of that. He pushed his hips at me, forcing his hard cock deep into my mouth, so much so that I started to gag. He was intent on face fucking me. I held tightly on to his legs, trying to steady myself so I would not fall over. Back and forth he went with his whole body, until he suddenly climaxed. He pumped his hot cum again and again down my throat.

I realized then that it was probably a first-time blow job for the horny young man. I sat down to catch my breath. My jaw ached and I needed a break. But he had other ideas. He literally picked me up like a sack of potatoes and threw me face down on to the bed. He pulled me back into position, pulled down my boxers, and started to push with his hard dick at my tight hole. There was no way he was going to get that big cock of his up my ass without some lube. I reached back to stop him and yelled, “Kid, take it easy. You need to lube up first.” “Sorry,” he quietly said. He backed away and reached down to his backpack on the floor. After rummaging around in it he pulled out a tube of lube and squeezed some out on his dick and on my hole. 

I won’t recount everything that happened next, except to say I was fucked multiple times in every position possible. I lost count of the times the stud came in my sore ass. His youthful stamina and enthusiasm finally was too much for me. The combination of the alcohol, the lack of sleep,  and the intensity of the fucking pushed me over the edge and I blacked out.

* * *

He and his frat buddies ended their antics in the water and left the pool area, leaving me with a raging hardon in my speedo. I stayed at the pool side for about a half an hour when I decided to get something to eat. I went back to my room to change. Opening the door I spotted a piece of paper on the floor that someone had slipped under the door. The note read: I NEED YOU TO FUCK ME. It included a phone number and a smiley face :). 

Part 3

I had trouble getting my speedo off after reading the note. I knew I had some business work to get done in the afternoon before meeting with the clients that evening, so I texted him with simple reply: 12 MIDNIGHT. It was a challenge to keep myself focused on my work as I sat at the desk finishing up the presentation for the meeting. The vision of his bubble butt in that wet swimming suit kept popping into my mind. I started to make a mental list of the things I wanted to do to him and that sweet cherry hole of his, considering that the night before he had made me into his personal cum dump. 

The dinner meeting seemed to drag on forever. I limited myself to a couple of glasses of wine during the meal, wanting to make sure I would be on the top of my game at midnight. The meeting was a success. I landed a big contract with a new client for the company, and they wanted to celebrate. Not wanting to be rude or ungrateful to them I finally had to break the party up at 11:30 p.m.

Returning to my room I quickly showered and got dressed for my guest. I put on my sexiest underwear I had with me. Next I got on my tightest faded blue jeans; a thin white T-shirt that showed off my pecs; and my favorite pair of slip on shoes. He was going to have to undress me if he wanted any action. 

I sat on the sofa and poured myself a Jack on the rocks to quiet my nerves a bit. And then waited. Will he show up? Or will I end up drinking myself to sleep? Precisely at midnight there was a soft knocking on the door. I thought I’d play with him a little so I did not open the door immediately. After a few seconds he knocked again, this time with more force. I laughed to myself, “I guess he’s determined.” I quickly opened the door and motioned him into the room. 

He had clothes on this time: a loose tank top that hung over silky blue athletic shorts, flip-flops on his feet, and that back pack on his shoulder.

“This your first time getting fucked?” I asked. In a quiet voice he answered yes. “What’s your name?” He hesitated and finally said, “Eric.” “Well Eric, my name is Brandon and I’m pleased to finally know the name of the stud that fucked my brains out last night.” I held out my hand and we shook hands. I asked, “Ready?.” Eric grinned and then loudly announced, “I’m down. Let’s do this.”

Taking him by surprised, I grabbed his head with my hands and planted my lips on his. His reaction was to pull away but I held on tightly and stuck my tongue deeply into his mouth. Suddenly, he tongued me and then very passionately started to kiss me. It was like I had awakened 19 years of pent-up desire in him. He pinned me against the door and pressed his whole body against mine. I could feel his rigid cock as he ground his hips into mine. That was not my plan for the night. I pushed him off me and said firmly, “Get your clothes off now.” He dropped his back pack, kicked off his flip-flops, pulled his shirt over his head, and then dropped his shorts. I was taken aback when I saw he had on a fluorescent pink-striped Andrew Christian jock. Seeing my reaction, the smart ass slowly turned around, whiggled his butt at me, and pulled off the jock, letting drop at his feet. He turned back and with a big grin on his face, held his big dick in his hand and waved it at me. I saw that he had shaved his balls and pubes.

I could hardly control the urge to take that beautiful piece of meat into my hungry mouth. Instead, I commanded him to drop to his knees before me. He had a puzzled look on his face. After some hesitation he slowly got down. Seizing his head, I pushed his pretty face into my crotch and held it there, until he gasped to catch his breath.

I released my hold and said, “All right, you can take my pants off now.” By this time my balls were aching and my penis was leaking precum. While still on his knees he methodically unbuttoned my jeans and carefully pulled the zipper down. He grabbed the waist band and with one swift movement he pulled my pants down to my feet. My cock was straining for release from my tight black bikini briefs, soaking the front of them with an abundance of precum. Without prompting, he buried his face in my crotch and started licking and sucking on my still fabric-covered dick. He looked up at me for permission and I nodded yes.

Eric grabbed the briefs and almost ripped them as he pulled them down. My red, angry looking thick 7-inch, cut penis flopped out into his face.He grasped it with his right hand and seemingly examined it from its tip to my balls. He then opened his mouth, stuck out his tongue, and tentatively inserted my throbbing rod inside. I don’t know what was going in his mind but I was completely turned on, looking down at that young, blond-headed kid with my dick in his mouth. I’m sure my dick was gushing precum. He pulled it out and began licking it from the base to the head, salivating like mad while doing it. He pushed the whole thing back into his mouth and began sucking like there was no tomorrow. For a novice, he sure knew what he was doing. The blow job I was receiving from him knocked me off my feet. I fell back onto the bed and spread out my legs to give him full access. He went hands free and started to deep throat me, surprisingly without gagging himself. Without warning my balls let loose and I released shot after shot of my seed into his mouth and down his throat. He held my penis in his mouth as it slowly deflated. When it finally slipped out he looked up at me, licked his lips, and gave me the biggest smile ever; just like his tattoo. He got up, and leaning over me, planted his cum covered lips on mine, and then laid his hot body on top of me.  

We actually laid there, embracing each other, for a good five minutes. I breathed in deeply his manly scent, burying my face into his chest and arm pits. I licked his nipples, now erect. I held on to his butt, holding his body tight against mine. I finally pulled myself from under him and got behind him, positioning myself between his legs. Before my eyes lay his beautiful virgin ass.

Part 4

The sight of his pink hole surrounded by blond hair that made it’s way up his crack caused me to salivate. I must admit, I absolutely love licking a guy’s ass. Cupping his hard butt cheeks in my hands I dived right in. I started with his taint and slowly worked my way to the prize. Eric began to moan and grabbed the pillows to steady himself. He quietly urged me on: “Yeah, oh yeah.” His reactions made me all the more excited and I stuck my wet tongue as deep as possible into his hole. His ass jerked into my face and he shouted, “Oh my God, Brandon, fuck me now!”

I reluctantly pulled out and stood up. I reached down to his backpack to get the bottle of lube I remembered he had there. “What the fuck!” I said, when I saw the other contents of the bag. Besides the lube I found a butt plug, a douching kit, enough condoms to supply an army of horny guys, and handcuffs. The sweet, innocent-looking college jock had a kinky side!

I had him stand up next to the bed and told him to bend over and spread open his ass cheeks. After  applying a generous amount of lube, I began preparing him for his first-ever anal fucking. With one finger, then two, I began exploring his insides; and locating his prostrate, I began fucking him with my fingers. Eric moaned, expressing his pleasure. His tight hole was opening up nicely and I decided it was time for the main event. 

Having been fucked already multiple times by Eric without any condoms I decided to go in raw. I knew I was clean, having been tested just a few weeks ago. Massaging his back, I could feel how tense he was. I said to him, “Eric, you are going to love this, but you need to relax. I’m going to go very slow.” I rubbed my cock up and down his crack and added my leaking pre-cum to the lube covering his cherry hole. What I don’t have in length I have in width so I really had to push hard to gain entrance. The head finally popped in, causing him to cry with his face in the pillow, “Fuck! That hurts!” “I know,” I said, “but soon the pain will be mixed with pleasure.” I pushed, he moaned. I pushed again, and he moaned louder. God, he was tight! When I finally bottomed it was heaven for me; not so sure it was for him. After a couple of minutes without moving, I asked, “Eric, are you okay? Should I pull out and give you a break?” 

His response was to suddenly move his hips and start to fuck himself. In utter amazement, I just stood there as he began to loosen himself up on my rock hard dick, pushing his butt back and forth, using his left hand to push against the bed and his right hand to jack his dick. He cried out loudly with each push, “Fuck yeah!” 

I came to my senses and realized that he was using me just like he did the night before. Using my penis instead of my hole! That’s not how I envisioned the way that it was going to go down that night. I abruptly pulled out, reached down to his backpack, and grabbed the handcuffs. Before he knew what was happening I slapped the cuffs on his wrists, pulling his arms behind his back. I put both of my hands on his back and pushed him hard down on to the bed. I then bent over and put my face next to his and said to him, “Eric, I’m going to do the fucking and I’m going to fuck the shit out of you now!” 

I grabbed his hips and pulled his ass up and positioned myself between his legs. I wasn’t going to go slow this time. I lined up my cock and with one swift movement stuck it all the way into him. His whole body jerked in response. I took a couple of seconds to catch my breath, and then I started rocking my hips back and forth as I began to fuck him. I increased the speed, giving myself a real physical workout. I grabbed him by his neck and pulled his head back for leverage. Drops of sweat began dropping off my head, falling on to his sweaty back. I plowed as deeply as I could, my balls slapping his butt.

Eric suddenly got into it, and between his deep moans started to cry out, “Oh yeah, oh yeah, fuck me, fuck me.” He arched his back and buried his face into the mattress. Jeez, for a virgin the kid sure knew how to take dick!

I had to see his face. I unlocked the handcuffs as quickly as I could, and with my cock firmly planted in him, I flipped him on his back. I held his arms down as he wrapped his legs tightly around me. Looking down at him I saw the look of pure lust in his steel blue eyes. There was not a hint of submissiveness to be seen in his face. 

Fuck! The stud was challenging me. He began working the inner muscles of his hole, grasping my cock every time I pulled out. I began to wonder if I would outlast him. I tried repositioning myself. going in at different angles until finally I managed to find his prostate. I knew I was hitting the right spot because Eric’s legs began to involuntarily shake. I began to pound him like my life depended on it when suddenly his cock exploded, sending shots of cum over his head, on his face, and on his chest. 

His hole was completely loosened up. It felt fantastic as I now slowly worked my way in and out. With the abundance of my pre-cum and the lube filling his insides, my cock was now in a happy place. I let his arms go and laid on his now totally relaxed body. He wrapped his arms around my back and hugged me tightly. I put my head on his cum-covered chest and listened to his heart beating. At that moment the whole experience changed for me. I felt one with Eric. In a quiet voice he cried out, “Oh Brandon, please fill me with your cum.” That set me off and my body responded immediately. I pumped load after load into him and then finally collapsed back into his arms.

Eric grabbed my head and pulled my lips to his and gave me a tongue fucking. His cock was still rock hard against my own. I finally broke the kiss and rolled off him. We laid there quietly next to each other for a good 5 minutes. He spoke first, “Brandon, that was awesome! Fuck me again, please.”

Before I could answer there was a knock on the door. Eric quickly got off the bed and said he would go to the door. As he opened it I heard him say, “Hi Mike, glad you could make it.” I sat up and looked. “What the fuck!” In walked Mr. Man-of-Few-Words, aka “Mike.”