This story is a work of fiction, but is based on real people in my life. It contains sexual material suited for adults and should be read by adults only.
This trip was about 15 years in the making. I and four of my friends had finally graduated high school and as a reward to ourselves, we opted to take a trip to Hawaii and bask in the sun and forget life for a few days. But before I get to that, let me give you a history our friendship. While growing up, we were "that" group of kids, always finding new ways to keep ourselves entertained and in doing so, we kept the neighborhood on their toes. It wasn't unusual to see us biking through fields or putting together a go-cart, only to launch it off the biggest ramp we could put together.
I had lived in that neighborhood all my life. I guess you could say I was the beginning of the trouble. When I was about 7 or 8 years old, Chad moved into the neighborhood and our similar interests of dirt bikes and the like drew us together. We began our reign of terror in the neighborhood, much to the dismay of our parents. Several years later, Toby moved in a few streets over and quickly became a part of our now growing group of friends. Finally, when we were about 12 years old, Bryan completed our circle of friends.
Just a run-down on who we are, my name is John. As clichéd as it sounds, I'm just your run-of-the-mill kind of guy: about 6 feet tall, light brown hair and average build. Not a toned jock or anything, but in shape and happy. Chad is a wrestler and is the shortest of the group, standing at about 5'6", but he's built like a blonde Adonis. Tobey is very similar to me. In fact, some say we could have been brothers, with is light brown hair and similar build. Bryan was a soccer player and had a well-toned body and abs you could do your laundry on.
Now, after eight plus years of living life, family issues, and the drama that comes along with high school, the four of us set out on what was to be one of the most interesting experiences of our lives; one we weren't soon to forget.
As with any long flight, our journey to Hawaii was uneventful to say the least. We kept ourselves busy with music and reading, as well as talking about our last year of high school and all our accomplishments, or in some cases...the lack of accomplishments. After over five hours of flying, we finally reached our destination, Honolulu and Waikiki Beach.
As we stepped off our plane, we were greeted by gorgeous local women offering up the traditional leis.
"Hey! I've only been on the islands for five minutes and I've already been lei'd!" You could always count on Tobey to take the obvious joke and actually make it funny.
"Tobey and I will go over and get our rental car, you and Bryan wait here with our bags," said Chad as the two of them went off to the rental counter. After several minutes, the two returned and the four of us piled in to the compact car and headed to our hotel on Waikiki Beach.
Being that we got to our hotel later in the afternoon, we quickly grabbed some food at a local restaurant and headed down to the beach, which was just a stone's throw from our hotel. The beach was crowded, but the people were thinning out as they were all headed off to the take part in the night life of Waikiki. We all stripped down to our board shorts and took our first of many swims in the beautiful waters that Hawaii has to offer. After some time, we began to get into our usual groove of having fun and raising a bit of hell.
"Let's bury John in the sand and give him a giant pair of tits!"
"That's a grand idea Bryan!" Chad hollered back.
Before I knew it, I was on my back and the sand began piling on top of me. The three teens slowly but surely loaded the sand all over my body. Once they were done, Bryan, Toby and Chad stood back to admire their work.
"I've got another great idea," said Bryan, as he slowly walked back towards me and my big sandy boobs and before I knew it, he had lost his board shorts and was on top of me (with a whole bunch of sand between us) and began to dry hump the mound of sand on top of me, his bare bubble butt there for the world to see. I couldn't help but laugh and join in on the fun.
"Oh yeah, Bryan! Do my harder!" I screamed, much to the dismay of the dozens of people trying to enjoy their dinner at a beach-side café. Needless to say, that little antic didn't last very long and we made our way down the beach to have a little more fun.
After a few more hours, the sun had gone down and our fun had ended up in a nice relaxing swim and watching the incredible Hawaiian sunset. We decided to head back to our hotel and get cleaned up and head to bed, as we were all dead tired from the flight and the time change.
"I get first shower!" called out Chad. He grabbed his things and headed into the bathroom. Toby, Bryan and I plopped down on the beds and clicked on the television. We began to talk about the many things we wanted to check out while in Hawaii.
"We have to go over to Hanauma Bay to do some snorkeling."
"Of course we'll head over there Tobey, but after we hit up Pearl Harbor," I said.
"Oh and we have to head up to the North Shore!" Bryan added.
"Yeah, I've heard the local chicks up in the North Shore are hot. Can you imagine hooking up with a chick like that?"
And as is almost always the case, a conversation among teenage boys turned to sex. By this time, Chad had come out of the shower wearing just a t-shirt and some basketball shorts and Bryan had gone off to shower. The remainder of us sat quietly on the beds and watched the hotel's information channel on what to do while visiting. Tobey and I had taken our turns in the shower and the four of us, in our t-shirts and basketball shorts or lounging pants, sat back and watched the television, waiting for sleep to come; which it never did.
After some time, Tobey, who was not shy about his love of porn, tossed out the idea of watching one of the flicks that the hotel had to offer and it didn't take much convincing to get everyone to agree. Being that we had grown up together, we were not shy about being naked in front of each other, as our activities on the beach earlier that day suggest, so it didn't take long for Bryan and Toby to drop their shorts and take the situation into their own hands, so to speak. Chad and I opted to keep things covered up, at least for the time being. After a few minutes, Bryan breaks the silence (save for the moaning and slapping of the movie).
"Hey Tobey. What are you working with over there?"
"What do you mean?"
"You look like you've got quite the tool there. Have you ever measured it?"
Chad and I, out of curiosity of course, had to take a look. Tobey was not afraid to be naked in front of us, but none of us had ever seen him with an erection before and we were all taken back by its size. Bryan on the other hand, wasn't shy at all. I'm pretty certain we'd seen more parts of his body than his doctor had. He was not lacking in the size department either and he was quite proud of it.
"No, I've never measured it before. No need to! The girls all know it's BIG and that's what counts!"
Bryan couldn't live with that answer and tossed out yet another grand idea.
"Well, I've measured mine. Come over here and we'll put them together to see whose is bigger."
After a bit of hesitation, Tobey walked over to where Bryan had stood up and the two teens stood dick-to-dick. Seeing my two friends together like set something off in my head. At the time, I had a curiosity about other guys. It was not something I had ever acted out upon, but I couldn't deny that seeing a good looking male gave me a bit of a stir inside. And now that I was all horned up and two of my best friends were standing in front of me with impressive boners, I was more than curious.
"Hey John, what are you looking at there kiddo?" asked Chad, who had remained rather quiet during the exchange. Damn...busted.
"Why don't you have John come over and take a closer look, make sure things are fair."
"Awesome idea," Tobey said, with a sly grin.
Without looking too excited about the idea, I slowly walked over and sat on the bed next to the two of them.
"How big are you Bryan?" I asked. I wasn't sure if I was asking for my own curiosity or for the sake of the measurement.
"I'm just shy of 8 inches," he said, with a hint of cockiness (sorry for the pun).
"Well, I hate to break it to you, but it looks like Tobey is just a bit bigger. He's probably right at 8 inches."
"Damn! Well I bet mine tastes better!" and with that, Bryan swung to the side and grabbed the back of my head. Before I could realize what had happened, I had the head of his cock in my mouth. Out of all my friends, Bryan was the one that I most wanted to "be curious" with. So I feigned a bit of resistance in the beginning but eventually pretended to give in to the idea, trying not to give away the fact that I was in heaven. Bryan slowly began to move his hips back and forth, every once in a while pushing in a bit further. Before long, I was able to take in most of his almost 8 inches. While I was happily gobbling Bryans cock, Chad had come over and sat next to me and had pulled Tobey over to him and the two of them began mimicking what Bryan and I had started.
Bryan pulled his cock out of my mouth and leaned down to kiss me. His soft lips met mine and we kissed passionately for several minutes. He stood back up and I grabbed his man pole once again. This time, I went after his balls, which were hanging low beneath his penis. I took them in one at a time and massaged them with my tongue, much to his delight, eventually turning my attention back to his hard dick.
"It's your turn now," he said softly and he knelt down between my legs. He wasted little time in taking my hard 6.5 inches into his heavenly mouth. He quickly bobbed his head up and down and I couldn't help but think he had done that before. But my attention was drawn elsewhere as Tobey and Chad had climbed on the bed, one on each side of my face and began alternately feeding me their hard slabs of meat. Chad's 6 inches easily slid into my mouth after having fed on Bryan's dick. It was quickly replaced by Tobey's large member. In my mind, I felt like I had been sent somewhere close to heaven, with three of the most beautiful males I'd ever laid eyes on were taking part in my "curiosity."
After going at it in that manner for some time, we began a rotation of sorts. I moved my attention to Chad while Tobey's mouth found its way around my manhood. Bryan wound up standing on the bed face-fucking Chad with happy vigor. The room was filled with moans and grunts of muted pleasure, only adding to the excitement of what was happening.
"Trade me places, Chad. I want him to eat my hole."
Upon hearing Bryan's request, my heart skipped a beat. He quickly squatted down over me, revealing his pink hole to my eager mouth. I attacked it with glee and was pleased by the squirming and moaning of Bryan as he grinded back and forth. I had reached my breaking point and grabbed Tobey by the back of the head and let loose a large load of jizz into the back of his throat. He groaned with pleasure. Shortly after, Chad began grunting and pulled out of Bryan's mouth.
"Ugh! I'm gonna cum! I'm gonna cum!" and the white goo flew all over Bryan's chest, who wasted no time in lapping the remains of the man juice from Chad's cock.
Tobey, having been lost in my crotch for some time spoke up, "I need to put my dick in someone!" Chad volunteered without hesitation and knelt down on the bed with his tight ass stuck up in the air. Tobey buried his face in Chad's ass, licking and slurping, lubing up the little pink button he was about to fuck.
Bryan had slid down so we were once again face to face and began a furious kiss. We were grinding our hard cocks together, with our hands exploring each other, attempting to find the pleasure spots. My fingers eventually found the hole that I had been tonguing just minutes before and I slowly slid a finger in. Bryan buckled with pleasure.
"Oh fuck! Yeah!" he bellowed. I quickened the pace of the finger fucking, eventually adding a second digit to the party.
Next to us, Chad was groaning with pain and pleasure as Tobey was plowing his ass with his big dick. Chad's hole was obviously providing some pleasure to Tobey as he almost seemed to be smiling as he ground into Chad's little bubble ass.
In between groans, Bryan whispered into my ear "I want to fuck you." He lifted my legs up and he began to lick and wet my hole. Once it was nice and wet, Bryan slowly pushed his prick against my hole, and bit by bit, he slowly slid into me. The pain was like nothing I had felt before, but it felt amazing. Once he had pushed his way in, he just left it there, letting my hole become accustomed to his throbbing stick. He slowly began to move back and forth, pumping into me with increasing speed. I reached back and grabbed his hot ass, pulling him closer to me. His huge balls slapped my ass with every thrust.
After a time, we switched things up again. Tobey lay down on his back and I hopped between his legs and slid my hard and ready cock into his hole. He jumped with surprise, but soon relaxed and took the fucking in strides. Chad cozied up behind me and began to hammer my ass, creating a trio of sweat and skin slapping. Bryan in the meantime, crawled over Tobey, which put the two of them into the "69" position.
The butt humping quickened its pace and the four of us became one mass of sweat and sex. Chad was like a jack rabbit in my ass, going fast and furious. I, in turn, struggled to keep a pace while fucking Tobey, but he didn't seem to mind as he was having plenty of fun blowing Bryan. I could tell that we are all getting close to exploding, as the moans became closer together. Before anyone could lay claim to the notion, I said
"I want you to come on me." So we repositioned to make this happen. I lay down on my back, while my friends circled around me on their knees. The four of us grabbed our cocks and began to finish ourselves off.
Tobey and his large tool were first to blow. "Oh fuck! Oh fuck!" He leaned forward and aimed at my mouth, launching a think wad of cum that landed on my chin. I grabbed his dick and sucked on it to get whatever fluid was left.
Chad opted to straddle my chest and as soon as he did so, I slid two fingers into his hole to massage his sweet spot. "Oh my hell, dude. Yeah!" With one hand, he was beating his meat quickly. With the other, he grabbed my wrist and pushed my fingers further into his hole. With one final grunt, he leaned back and shot a massive load over my head onto Bryan, who looked on in awe. That sent me over the edge, causing me to blast a load of cum on to Chad's back, who had continued to ride my fingers.
Finally, Bryan scoots ups close to my mouth and I take him in, just the same way the night began. He once again face fucked me. "Oh shit, man. I'm cumming!" With one last thrust, he pushed his prick to the back of my throat, shooting a load of his sweet juice into my mouth.
We all laid back, covered in sweat and sex, breathing heavy, trying to take in what had happened; all of us unsure of what to say. After several minutes, Chad, the last person I thought would break the silence, let out a big sigh and said:
"If this happened on the first night we are here, I can only imagine where we go from here. This could be the best vacation of my life."
The rest of the trip we spent the days touring the island and the nights spent ravishing each other's teen bodies. Needless to say, it wound up being an amazing vacation that brought the four of us closer than ever.