This is the first of what will probably be 9 or 10 stories from a recent Hawaiian vacation. Names have been changed to protect the guilty. If you are not an adult or if the place where you live takes a dim view of hot man on man sex you are in forbidden territory.
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HAWAIIAN VACATION – Part One
Matt and I met the old fashioned way, in a bar. I noticed him right away. He's a tall, lean dark-haired looker with piercing brown eyes and a 5000 watt smile. His soft British accent was charming, and his pullover shirt showed off a perfect lean torso. The attraction was instant and mutual, even though he's just 24 and I'm a little more than twice his age.
At first I wondered if I was attracted to his body and he was attracted to my money, but, to my surprise and delight, that didn't turn out to be the case. He didn't mind me spending money on him, no doubt, but that wasn't the only thing he was after.
"I noticed you the minute you came in," he said. "That's an amazing chest." He's not the first guy to say that. My chest is probably my big selling point: 46 inches of solid muscle on top of a 32 inch waist.
Matt was not shy. He ran his hand over my pecs and squeezed them a couple of times. Then he took my hand, put it on his upper thigh, and said, "Feel how that turns me on."
When I moved my hand over his crotch I didn't know if I was feeling a very big penis or a full grown cucumber. Damn it felt big. I wanted him right then. No need to plan dinner in two weeks, or a movie sometime that weekend. This needed to happen now.
I slammed down the rest of my drink and said, "There's no point in staying here. Let's go some place we can be more comfortable."
We got a cab back to my place to "get to know each other better," which of course meant we had animals in the jungle type sex. As great as he looked in clothes, Matt looked even better out of them – the perfect V-shaped torso, a dusting of chest hair, perky nipples and enormous balls. And then there was the main event: a big fat uncut eight inch cock, a thick piece of meat that tapered slightly from the base to the head and as nice as any I've ever seen.
While I was admiring his manhood Matt pulled my shirt over my head and began massaging my pecs. "Now that's what I call a chest," he said, then leaned over and began sucking on my nipples. They are hot wired to my cock and Matt soon learned this. After just a few minutes of his chest torture I threw him on the bed and reached into the nightstand for a condom.
"Put that on yours," he cooed. "I want to feel you inside me."
We didn't get much sleep that night. I fucked him twice. He came both times without even touching his dick.
Matt and I understood from the beginning that our age difference and being at opposite stages of our careers would make having any kind of committed relationship difficult. But we enjoyed each other's company, and on a scale of 1 – 10 the sex was an 11. So even though we weren't exclusive we saw each other very regularly. Matt is mostly a bottom and loves taking my cock, but I eventually learned to take his as well.
After Matt graduated from law school he had four months before starting with a big Wall Street law firm. It was the perfect time, and probably the only chance we'd have for four or five years, to take a month long vacation together. One night over a steak and wine dinner I pulled two airline tickets out of my coat pocket. Matt was so happy I thought he would give me his ass right there in the restaurant.
We landed in Hawaii two years to the day after our first night together. The first half of our vacation was going to be spent on Kauai, the northern and westernmost of the major Hawaiian Islands. It was not a lay on the beach or at the pool type trip. We were there to do a lot of hiking, bicycling and surfing. The first three days we spent hiking and camping on the Kalalau Trail, eleven grueling miles of paradise with breath-taking views along the Pacific Ocean.
I knew that after roughing it in the great outdoors we'd be ready for some pampering and creature comforts, so I booked a suite at a five star spa-resort on the north shore of the island. I'd like to tell you we spent the first night there having earthquake causing sex, but the truth is we were just too tired. After a great dinner we went back to the room, kissed each other goodnight and fell asleep right away.
The next morning was when the fun began. I woke up about six a.m. to find Matt between my legs and my fat six and a half inch cock between his lips. He started, as he just about always did, by working on the head of my dick. Once he'd gotten me rock hard he deep-throated me, then sucked on my very full balls. In a matter of minutes he had me nearly ready to come. Knowing how close I was he backed off, grabbed the lube off the nightstand and began to prepare my cock for a joyride in his super tight boy hole.
Then there was a knock on the door.
"Room service," a male voice said.
"Damn," I said. I'd forgotten that the night before I'd ordered breakfast in bed as a surprise for Matt.
My boy, who'd gotten very horny while blowing me, looked disappointed. But I had an idea how to make lemonade out of these lemons. Maybe I could make it a memorable morning.
"Want to have some fun?" I asked him.
"I was just about to have a lot of fun," Matt said. "And so were you."
I knew Matt had an adventurous and exhibitionist side. "Go answer the door," I told him.
"But I'm naked and hard as a rock," he said.
I winked at him and said "I know. What a nice surprise for the guy bringing our food."
Matt stood behind the door as he opened it to allow the room service guy to wheel in the food cart. Our waiter looked to be a native Hawaiian, and a very handsome one. I guessed he was in his early 20s, tall and seemed to have a nice build under the too baggy hotel outfit. He looked at me, smiled and asked where I wanted the breakfast served. That's when Matt, with his eight incher at full staff, stepped from behind the door and said, "We were just about to give the bed a real workout. Why don't you serve it to us there?"
The waiter's mouth flew open when he saw Matt's huge cock and balls, just like mine did two years before when I saw his package the first time. He didn't even try to hide the fact that he was staring. Matt teased him a little, using his muscles to make the weighty penis bounce up and down. I was pretty sure I saw a wet spot on the front of the waiter's slacks.
"Do you like my boy's cock?" I asked. "It's a nice one, isn't it?"
"Yeah," the room service guy replied. "He has a great cock." The waiter licked his lips; I noticed a little sweat building up on his forehead. He wanted Matt's big dick so bad I knew we could talk him into just about anything.
"Why don't you suck it for him?" I said as I climbed out of bed.
"I . . . I don't know," he stuttered. "I need to get back to the restaurant soon."
"It won't take long," Matt said while stroking his fat, long manhood. I've got a four day load built up and my cock is spring loaded and ready to shoot."
That was all the convincing the room service guy needed. Immediately he went to his knees, pulled Matt's foreskin back over the head of his cock and began sucking. Once he built up a rhythm he began to loosen his tie and pull off his own shirt. Before long he was deep throating eight inches of boycock and moaning loudly while he did.
I walked up behind Matt, reached my arms around his chest and began to pull on and twist his sensitive quarter-sized nipples. That made him moan. Then I began kissing his ears and neck, which he loves. My hard cock was right at the entrance to his ass; I slid it between his crack, causing him to shiver.
"How's he doing?" I asked.
"He's got a vacuum cleaner for a mouth," my boy said as he grabbed the waiter's head and began jamming his cock in. "The only way this could be any better is if you were fucking me."
"Well then I guess I need to do that," I said.
Quickly I grabbed the lube, slathered some on my cock and rubbed more into my boy's ass. I placed my cock at the entrance to his hot tight ass and slowly slipped the head inside. I held still to allow Matt to get used to the intrusion. I didn't take him long to start backing his ass onto the full length of my cock until I was balls deep in him. Matt was aching to be fucked and I was anxious to give him what he wanted.
Meanwhile the room service waiter picked up the pace of his sucking. He grabbed Matt's ass, pulling his cheeks farther apart so I could go in even deeper. I noticed he'd pulled his own cock out of his pants and was jacking himself frantically.
Soon we were in a great rhythm, with Matt the meat in a hot fuck sandwich. He and I were both sweating heavily and you could hear our skin slapping together. His asshole was gripping my cock like a vise.
"Fuck me, daddy." Matt panted. "Fuck me hard."
"You like having my cock in your ass?" I teased him.
"Oh yes," he moaned. "Fuck your boy. Jam that big cock into me harder. Wreck my hole. Pound me. Fill me with your hot cum."
I gave him what he wanted. My strokes went from slow and steady to fast and furious.
"How's that, boy? You like the way that cock feels in your ass?"
"Oh god it feels so fucking good." Matt said. "Nothing feels as good as when you fuck me like this. You made me so hot I'm going to cum in this guy's mouth right now."
And cum he did; Matt's eight incher shot seven times into the waiters mouth. It was far too much for him to swallow. Seconds later the thick white stuff was spewing out of his mouth. He wiped his chin with his hand and rubbed Matt's cum on his own cock for lube.
The contractions in Matt's ass when he came sent me over the top. "Awww, Matt," I yelled as I fired my own four day load into his hot rear piping.
After I pulled my still hard cock out of Matt's ass the waiter surprised us when turned Matt around and began sucking the cum from his abused hole. After cleaning my boy up the waiter crawled over to me and stuck my dick in his mouth, licking off the residual cum and Matt's ass juices. While he tended to me Matt and I kissed, our tongues intertwined, our hands all over one another. Both our cocks began to stir again.
"Are you ready for more?" Matt asked as he pulled at my nipples. That's what he always did when he wanted sex. It always worked.
"Let's have breakfast first," I said. "Then we'll put the do not disturb sign on the door. No hiking today."
Before climbing back into bed I gave the waiter a $100 tip – it seemed like the right thing to do – and asked him to serve us the breakfast in bed.
"It will be a pleasure," he said. "And thank you for my breakfast."