"Michael, come in here right away and bring the Debussey file with you."
Even though I'd been working here for 4 months, I still jumped every time I heard his voice. Partly because I was still getting used to the fast-paced, demanding work that comes with being the personal assistant to the CEO of a major corporation. But mostly because his deep, resonant voice still made the hairs on the back of my neck stand on end, remembering that morning in his office.
I had gotten a help desk call to come to Mr. Walden's office early one morning back in September and it ended with the best sex I've had in my life. Oh, and a promotion. I took the job, and it had been non-stop training and adjusting to a very different work life. I was wearing a shirt and tie to work every day now. I hated it, but at the same time kind of liked the way I looked. It definitely made me stand out in a crowd, which got me a lot more attention than usual.
Unfortunately, I wasn't getting the kind of attention I really wanted. I guess I had just assumed that I would be performing a lot of "special duties" for Mr. Walden, serving his incredible cock as needed. But nothing had happened since that first time, not even an acknowledgement that it had even happened! I would be lying if I said I wasn't disappointed. He was everything that turns me on in a man...a hot daddy bear with a spectacular beard. Oh, and that cock. Damn it was amazing and he knew how to use it! I guess his wife was giving him everything he needed now, so I was left out in the cold.
Truth be told, I wasn't all that cold. I had no problem hooking up with guys when I wanted sex. I was pretty hot, if I do say so myself. More of a cub, I guess. People tell me I project a lot of self-confidence...I have a Mohawk and a nose piercing, so I'm just intimidating enough to be interesting! I was 26, but most people thought I was in my 30's. I was pretty versatile when it came to sex, up for anything hot with the right guy. But right now all I could think about was dropping to my knees and taking Mr. Walden's thick, hard cock down my...
"Michael! Are you coming?"
Shit.
"Yes Mr. Walden, sir." I had completely spaced out for a moment.
I hurried into his office with the file, and quickly poured him a coffee. It was his fourth but I knew he needed it. He was sitting at his desk, leaning back in his chair reading through a stack of papers. His jacket was off and his tie loosened. I still got butterflies whenever I saw him. He had such a sexy daddy look...a buzzed head, beautiful beard, piercing blue eyes, and a bulge in his pants that could stop traffic.
"I was beginning to wonder if you were still here" he quipped.
"I'm sorry, sir. Just took me a little longer tha expected to get what you needed. Here it is."
I handed him the file, and put the coffee down on his desk. He reached for it instinctively and started reading. I waited a moment, and not hearing any additional orders, turned to leave.
"Just a minute, Michael. I need to talk with you about something before you go."
I stopped and turned back towards his desk, always a bit nervous. Had ai Screwed something up? Was he mad that it took me so long to get the file he needed? It's his own fault for being so damn distracting...
"Michael, the kids are out of school for a few days so we are headed over to our place in Hawaii for a long weekend. Need to get away from this weather and soak up some sun. We will leave Thursday and get back late Monday night."
"Yes sir," I replied. "Is there anything special you need me to do while you're gone?
He looked at me rather puzzled, his beautiful eyes squinting a bit with a bit of a frown.
"What are you talking about" he asked.
"Well sir, I just thought perhaps there were some special things I could help with while you're..."
"Michael, when I hired you for this position I told you that when I travel, you travel. A vacation is never really a true vacation. I'll be working most of the time, and will need you there with me. That isn't a problem, is it?"
"No sir, not at all. That's kind of amazing. I've never been to Hawaii."
"Well, keep in mind you'll be working so it won't be completely relaxing for you. Get IT to issue a laptop you can bring with you and be sure they set you up with a VPN. Well, you know all of this stuff I guess...that used to be your job."
"Yes sir, I understand completely. Thank you, sir."
I couldn't believe I was going to Hawaii. The next two days flew by. Everything was all set for the trip. Mr. Walden arranged for a car service to pick me up to take me to the airport Thursday. The whole family was there at the gate when I arrived. They really were kind of sickingly cute. Handsome dad, beautiful mom, and 3 well-behaved, adorable children.
I'd met Mrs. Walden a few times when I had to stop by their house to drop off things from the office. She was quite stunning. She was a tall, strong latina woman with an amazing body. She was probably close to 50 herself, but was in great shape. Clearly she spent a lot of time at a gym. I never really paid a lot of attention to women's bodies, but I knew a hot one when I saw it. She had beautiful tits...and she always dressed to show them off!
The flight was long but uneventful. I had never been in first class before, and it was pretty awesome. Nice to see how the other half lives. We had an entire meal, plus snacks to keep us occupied. The flight attendant was cute, and gay, and the booze was all free, so yea, I got a little bit of a buzz. And yea, I was horny as fuck.
Most of the first class passengers had drifted off to sleep but I was wide awake...too excited to sleep, I guess. The flight attendant was walking the aisle to check on everyone. He stopped by my seat when he saw I was awake.
"Can I get anything else for you sir?"
That made me laugh a little. No one ever called me sir.
"Nah, I'm good thanks. I don't think I could handle anything else."
"Ah, don't sell yourself short. You look like you can handle plenty," he replied.
My dick shot up in my pants at that remark, and I shifted a bit to give it room.
"So, have you been to Hawaii before" he asked?
"Nah, this is my first time. I'm super excited. I don't really know what to expect, but I know it will be great. This is kind of a work trip, but I'll find time to have some fun."
"Well, if that guy you're travelling with is your boss I think you will definitely have plenty of fun" he said, motioning to Mr. Walden who was sleeping in the row in front of me. "He looks like he needs a lot of attention!"
"Ha. Yea, he's pretty amazing. And pretty fucking hot. I'm hoping there will be some extra work for me to do for him this week" I said with a wink.
The plane landed and we were in Hawaii at last. First order of business? Find the bathroom and jerk off. I was pitching a tent big enough to sleep a family of 6. I saw the men's room, and headed straight for it. I got to the urinal, and pulled my cock out. Fuck yea that felt good.
I started to stroke, knowing I had to be quick, when another guy came up to the urinal next to me. He pulled out his cock, and yea, I had to look. Shit it was huge. Thick as a beer can, with a hot zero-gauge PA hanging off the end. I knew I needed to be cool, but I couldn't help but stare. He stepped back a bit so I could get a better view. I glanced up and him, and he smiled a little.
A split second later, I was on my knees trying to cram that fucking monster down my throat. He backed me up against the wall between the two urinals and skull-fucked me. He didn't say a word, just moaned as he thrust his meat down my throat.
The PA was hot. I slid my tongue in and around it, as I choked on his cock. His dick head must have been really sensitive, because it was driving him crazy. I was so fucking hungry for this!
It didn't take long...just a few minutes and his load was mine. He thrust that fat dick deep in my throat and let it pour out. As soon as that salty cream hit my throat, my own dick erupted like a firehose. Fuck that felt good. Let's face it. I'm kind of a pig. He zipped up and left without any acknowledgement.
I wiped up as best I could and headed back out to where everyone was waiting for me, somewhat impatiently.
We grabbed the luggage, picked up the car, and were at the house in less than an hour. Their house was spectacular. Huge, open and airy...and right on the beach. There were views from almost every place you stood. The kids quickly ran off to the beach. I was directed to my room and quickly unpacked. I opened the windows and found an incredible view looking out over the backyard and onto the beach.
I stood for a few moments enjoying the view. Mr. and Mrs. Walden came out of their bedroom onto the lanai just past my windows. I stepped back a little to where they couldn't see me. They were already in their swimsuits. She was wearing an amazing fire red bikini that showed off, well, everything. Her tits were barely contained, and the curves of her hips were stunning. Hard to believe this woman had goven birth to three kids!
Mr. Walden was wearing a bright blue speedo, and he was wearing it well. He had a spectacular ass and the swimsuit showed it off nicely. He was semi-hard, so the basket was full in the front. He leaned in and kissed his wife and his hands stroked her breasts. He kissed her passionately, and I could see his dick growing harder. Her hands reached down and pulled his massive cock out of his speedo. I hadn't seen it in a while, and wow, had I missed that beautiful cock!
He put his face down to her tits and began licking them and driving her crazy, I could tell. He pulled her bikini bottoms down and his cock immediately pushed into her cunt. I couldn't hear them, but I knew she has to be moaning in pleasure. Her head fell back and her back arched. He slowly began to pump his cock into her.
His mouth was hungrily devouring her tits as he fucked her. I looked around, trying to see if I could quietly open the windows. I wanted to hear this. I managed to crack one of the windows slightly, just enough to hear a little of the action. God, this was like watching live porn!
He was grinding into her fast now. Pulling almost all the way out of her, and then shoving it back in. He backed her up against a column and began to pound her pretty hard. He was so aggressive, even with her! I could tell he was getting close.
"Yea, baby...take that fucking cock. I'm gonna fucking explode inside your cunt."
He barely got the words out when he did just that. His whole body shook as he unleashed his man juice in her cunt. He held his cock inside her and she clinched down tightly to hold it in. He kissed her as his soft cock slipped out of her dripping pussy.
He quickly pulled up his speedo, and she her bikini. Goddamn. I turned back to my room, feeling a little guilty. But damn. Seriously. That was incredible, and my fucking dick was hard again. I pulled my dick out of my shorts so I could knock another load out. No sooner did I have my dick in my hands when my bedroom door opened and Mr. Walden stepped in.
I tried to hurriedly stuff my dick back in my shorts, but I knew it was too late. He laughed a little.
"Did you enjoy the show, son?"
I was a little taken aback to learn that he knew I had been watching...but I was also suddenly weak in the knees. He hadn't called me son since that morning when he fucked me. God that made me melt.
"I. um, I'm sorry I..."
"Don't worry about it. I knew you were watching. I wanted you to see us."
He walked over to me and reached out his hand to touch my face. Fuck, it was electric. I looked up at him. Those eyes that had first captured my attention were so incredibly blue. That hairy chest. The dad belly covered in fur. And Jesus Christ, he was of course hard again.
His hand grabbed the back of my head and pulled my face to his. His mouth opened up and hungrily engulfed mine. His tongue pushed its way into my mouth as he pulled me closer. I felt his hard daddy dick push into me.
He pushed me to my knees, and pressed his fat bulge against my face. God, I had been waiting for this moment for months. I reached up and pulled his speedo off. His thick hard cock sprang out, catching me by surprise. I had forgotten how impressive it was. It was still sticky and wet from fucking his wife which made me insanely hot.
I pressed my face in close. I could smell her cunt juices on his cock. It surprised me how much that turned me on. Daddy grabbed my face in his hands and pushed his cock down my throat.
"That's my boy. Show dad how hungry you are for his fat cock."
His meat pushed deep into my throat, cutting off my air for a moment. It was intense. His hands closed in around my throat, bringing me just to the edge of blacking out before he released his grip and slowly pulled his cock out. I gasped for air, and then hungrily dove back down on his cock.
"Fuck yea, son. You ready to take dad's load?"
I didn't bother responding, and instead just worked faster. He closed his eyes and moaned softly, as I sucked his massive bone. I alternated form fast to slow, and swirled my tongue around his cock head each time he pulled back. I could tell he was close.
I went down deep on his throbbing shaft and pushed it down my throat just as he exploded. He was so deep down my throat I couldn't really even taste it...it splashed against the back of my throat and I swallowed every fucking drop. I have no idea how he was able to produce this much cum, but damn it was amazing.
I stood up, shaking just a bit. He grabbed me by the shoulders to help me steady myself. I turned to grab my shorts but he stopped me and kissed me. It was a long, hard passionate kiss and it drove me crazy. God I wanted this man so bad. He pushed me up against the wall of the bedroom and then slowly dropped to his knees.
So, um, yea. This was new. I had no idea what he was going to do, but before I could give it a second thought I felt his beard against my boy cock. His mouth opened up and he began to suck me. Holy shit. My cock jumped at the feeling of his warm, wet mouth, as he took me down to the nuts. I had no idea how to respond to this. It felt amazing, but totally caught me off guard.
He grabbed my hips and pulled me into him. Even on his knees sucking my dick, he was totally in charge.
It didn't take long. In less than a minute, I felt it happening...almost like an out of body experience. I wanted to tell him I was going to cum, but only managed to get out a brief "Oh god" before I erupted.
The first shot caught him by surprise, but he pulled me in deeper and swallowed every drop of my boy load. He sucked every drop out of me, as my dick went soft in his mouth. He slowly stood, and kissed me. I could taste my cum on his breath. He clinched his hand tightly around my throat and looked deep into my eyes, and then turned and walked out without a word.
I stood there for a moment, unsure what to do. Or really, what even had just happened.
After a few moments that seemed like an eternity, I grabbed my shorts and managed to pull them up. I walked out onto the lanai. It truly was breathtaking, but I had work to do. I had to remind myself that this was not technically a vacation for me. Not easy to do when you're surrounded by all of this!
It was just starting to get dark. Mrs. Walden decided to take the kids out to get shave ice and explore a little bit. I gathered some reports together to review with Mr. Walden. With the time difference, there was still time to get his signature on a few things that I could scan and send back to the office.
I wandered around the house looking for him...wasn't sure where he was, and the place was enormous. I heard some noise in the kitchen, and headed that way. I turned into the entryway and nearly ran into him, emerging with two amazing looking cocktails.
"Michael! I was just coming to find you. Here, taste this. It's my own secret Mai Tai recipe."
I took a sip. It was amazing, and strong! I think his "secret recipe" was half a bottle of rum.
"Come on, Michael, let's take these outside and enjoy the sunset while we can."
I followed him outside and down to the beach. On his way, he grabbed a blanket which he tossed down onto the sand. He sat and motioned for me to do the same.
"It is an amazing view, isn't it?"
I nodded, even though the view I was enjoying wasn't what he intended. He was wearing a pair of white linen shorts, and it was fairly obvious that he wasn't wearing underwear. I could make out the outline of his thick cock head through the fabric which had me totally distracted. He was shirtless, so I could enjoy staring at his amazing dad belly, covered in fur. He looked more relaxed than I had ever seen him. And more handsome.
I took another sip of my drink. It was already having a nice effect on me. I felt pretty chill and happy. And horny. What else is new, though.
"Come on Michael, let's take a quick swim before the sun is completely gone."
"Well, sir, I didn't bring my swimsuit down..."
He stopped me laughing, as he stood.
"Son, we're alone now...I think it will be okay."
With that he dropped his shorts, and walked down to the water. I stood for a moment, staring at his spectacular ass. Damn.
I pulled my shorts off, and awkwardly tried to hide my erection with my hands as I followed him. The water splashed up against my feet, and felt warm and refreshing.
I was about waste deep in the clear water when Mr. Walden swam up behind me. I felt his hands reach out and stroke my boy ass, half under the water. He stood up behind me and his hard cock pushed into me. His big strong daddy arms reached around and pulled me close, and his mouth found its way to my neck. He lightly bit the back of my neck as his hands gently stroked my face. It felt electric.
I began to push back, rubbing my tight boy ass against his massive daddy dick.
"Mmmm, yea, son. That's my boy" he moaned.
One hand slowly found its way down to my ass, and his fingers began to explore my hole. I felt my as opening up to take his finger, making my dick throb in excitement.
He slowly turned me around until I was facing him. His hands grasped my throat and pulled my mouth to his. He hungrily kissed me, making my entire body shake. I reached down and grabbed his fat cock in my hands and began to stroke it slowly.
He turned and led me back up onto the beach to where our blanket was waiting and pushed me down on my knees. I didn't need any further encouragement. I quickly wrapped my mouth around his beautiful cock, and took as much down my throat as I could.
He fucked my throat gently, pushing it in and holding it there. His hands grabbed my face and held it in place for his thrusts.
He gently lowered me until I was lying on my back. He was on his knees in front of me. I had sensory overload...the sunset, the beach, the daddy. It was like a dream.
He leaned in and spread my legs. He lifted them up and let them rest on his shoulders. I knew what was coming next, and was trying to brace myself. I hadn't been fucked without lube in a long, long time, and his dick was enormous. I knew it would hurt, but I wanted it so badly.
As if reading my mind, he spit onto his cock, using his hand to rub it all over. He then spit into his hand, and used it to massage my asshole. His finger pushed in, making me wet with hunger.
I felt the head of his cock, that beautiful daddy dick, resting up against my tight, pink boy hole. He teased my hole, rubbing his cock head there for a few minutes. He was driving me crazy!
He began to slowly push into me, his thick shaft disappearing into my ass inch by inch. It was definitely rough, but it felt incredible. I hadn't been fucked by a dick this big since the first time he fucked me months ago. It was like being opened up again.
He looked down at me as he pushed all the way in, that last inch inside me. He held still for a few moments, and then began to pull out. Just as the head of his cock breached my boy hole, he pushed back in again. Over and over and over. His rhythm was incredible.
My dick was bouncing against my stomach, harder than it had ever been. I was tempted to stroke myself, but I knew I would cum too quickly if I did. I wanted to enjoy this. He was enjoying my ass, I could tell. His breathing was heavy and measured, and he softly moaned each time he pushed in.
"Son, I'm gonna breed you. I'm gonna shoot my seed deep inside you."
"Yes, daddy. Oh fuck. Yes, sir. Please give me your load, daddy."
He began to pick up his pace, thrusting in quicker and quicker. I didn't know how much longer I could wait before I exploded, but I wanted it to last. He had his eyes closed and was moaning loudly now.
"Goddamn it, son...I'm gonna fucking nut in your boy cunt. I'm gonna fucking make you my whore!"
"Yes sir, please sir. Please daddy. Breed me like a bitch, sir. I need your load, daddy!"
"Oh shit. Michael! Oh fucking shit, I'm gonna..."
With that, I felt his body go rigid as he pushed his fat cock all the way on my ass.
"GODDAMNITFUCKER...!"
He erupted into me, his massive daddy load exploding into my thirsty ass. I felt spurt after spurt come into me as he drained his nuts.
"Oh god, sir...oh god daddy, I'm gonna cum, daddy!"
My dick shot into the air, with the first drop landing in his beard. The rest coated my chest and belly, spilling out everywhere.
I could feel his dick getting soft inside me as the last few drops oozed form my boy dick. He collapsed on top of me, with my load cementing us together.
He kissed me as his dick finally slipped from my dripping hole.
He bit my ear as he gently whispered.
"Welcome to paradise, son."