Hot Naed Fun!

I just turned 25, and I'm recently single after a 4-year relationship. That's not true; we broke up almost a year ago, and I am at my wits' end with being alone.

My name is Sidney Harrison Newman -- fuck I know my mom was a fan of Harrison Ford and Sidney Poitier, thank God, she didn't name me Paul. Objectively, I'm in great shape, have been told I'm handsome, and generally, am a good guy. I'm 6'2" tall, with blond hair, emerald-green eyes, 44" chest, 30" waist, 8-pack, nice cum gutters, bubble butt, and a decent cock.

My best friend and head of operations for my company, Olivia tells me I'm fucking hot and should use my body to catch a hunk of a boyfriend or at the very least have lots of sex; the problem with that is, I'm not one to sleep around I want a relationship, kids and a future with the one. She keeps telling me that I might have to fuck a lot of frogs to find the prince, not sure I'm interested in that but sex with another human being sounds good as Ronnie Palm and his five brothers have become a bit boring, maybe I should invest in a few toys.

I knock on Olivia's door as she has invited me over for a dinner party with our closest friends that we will be hosting for a two-week vacation in Belize. Fuck I'm so glad I put a nix on her trying to set me up for this vacation, she typically tries to set me up with these incredibly hot, sexy guys that don't have a lot of substance -- the last guy she set me up with told me that his passions were food and video games and that his a most memorable event was playing Assassin's Creed Valhalla for 24 hours when it first came out. He was absolutely stunning but, damn a video game as his most memorable experience as a 28-year-old, oh well, she meant well.

Instead of Olivia answering the door, her twin sister Alicia answers the door, giving me a big hug as she pulls me into the house, telling me to watch myself as Olivia has invited, as she puts it, my forever man. Alicia squeezes my arm and tells me it will be ok -- just enjoy yourself tonight because the vacation Oliva has planned is going to be awesome and it's not worth getting wound up over. I thank her for the heads up, we grab a glass of cabernet, and start to mingle with the different people who are already there. I still have not seen Oliva and asked Alicia about it; Alicia is vague about where she is, but lets me know that she will be back soon. She assured me it was nothing to worry about.

Olivia came in a short time later with 20 beach bags filled with stuff; they all appeared to be made up for a 2-week trip that starts with an 8 AM flight tomorrow to Belize. Leave it to Olivia to have all her guests at a party the night before we leave. While Olivia had planned the whole event, we were flying on my jet and staying on my island getaway. Okay, yes, I'm from money and have made my own as well -- the island I inherited from my grandparents, which caused a commotion, but it was clearly articulated before they both passed that the island was mine. The plane I bought on my own after I sold my first tech company to Amazon for several billion dollars.

As she was handing out the bags, she was also handing out room assignments, which I called a stop to right away, as I would be staying in my room in my home. "Olivia, nice try, but you are not getting my room. Remember I am hosting this little getaway and not charging you a dime - my island, my room, my butt in my room. The remainder of the rooms can be handed out as you see fit." Olivia pouted but went on about her business.

I pulled out the itinerary and was shocked at the introduction -- 'Once you are in your room, you will store your clothes and not wear clothing for the rest of the two weeks unless they are required for safety during an activity.' I was taken aback as this had not been a point of discussion in all of our planning, I'm sure she left that detail out so I could not find a way to back out -- "Olivia dear, have you considered the staff that works on the island and whether they will be comfortable with 20 nude people running around for 2 weeks?"

Olivia openly laughed at me -- "I talked to the staff and they all agreed to be nude as well -- Alex was quite taken with the idea. I think he wants a chance to see you in all your glory, and don't worry, you are not the only bi/gay person attending; half of the group is either gay or bi." "Gee, that makes this sooooo much better. Ok, I'll get on board." I didn't look through the bag, but everyone else was oohing and awing over the contents.

Alicia hooted and hollered about Sid getting on board with a naked vacation with girls and everything. I flipped her the bird; I don't think she really thought I swung both ways, but I definitely prefer the male form -- hard-chiseled and downright amazing. Fuck, makes me hard just thinking about a hot bodied man.

An hour later, I was saying my goodbyes so I could get packed for the trip, but I was stopped by both Alicia and Olivia. They made it clear that I was not leaving and all my stuff had been brought over with Olivia, and that was why she was late. "Ok, where am I sleeping then? I need to get to sleep to fly us down." Alicia raised her eyebrows and queried about me flying the plane and why there weren't real pilots. I assured her I was a 'real' pilot and that I was fully capable and licensed, but needed to be coherent in the morning, or none of us would be leaving until I was ready. It hit me then that my co-pilot, Bryce, would be staying with us on the island. Did Olivia remember to tell him it was a naked vacation or not? Shit, I was going to be fucked as I had a major crush on the guy and wanted to stuff him full of my cock. How am I going to manage 2 weeks with us naked and not embarrass myself with a full-on boner?

Just then, the front door opened, and in walked Bryce -- 6', brown hair, blue eyes, stunning chest, and what appeared to be a rock-hard physique underneath. It took every ounce of control I had to not attack him when he was near -- not only was he stunningly gorgeous, but he was witty, well-read, and someone who could carry on a conversation beyond a video game. Olivia handed him his beach bag; he took out the itinerary and got a huge smile on his face. If I read his lips correctly, he was asking her how she got this past Sid. I could not see her face, so I had no idea what she said, but he blushed bright red and looked down, smiling the whole time.

I walked up to Bryce and Olivia -- "So where am I crashing?" Olivia smiled her mischievous smile -- "You and Bryce are in the guest room; you know where that is, right? Will you show Bryce where he can crash until you two must head to the airport?" I leaned and kissed her cheek -- 'You are going to pay for this, you know that, right?' She smiled her best smile and winked at me. So, it begins.

I showed Bryce the guest room; I could not tell what he was thinking because it only had a king bed, and I know I was dreading trying to get some sleep, as I tend to cuddle up to a warm body in the same bed; I just love the feeling of closeness. I made quick rounds of good nights and let everyone know the wheels on the airplane would be up at 8 AM sharp, and you all need to be on board no later than 7:30 AM, so don't be late.

When I made it back to the bedroom, Bryce was already in bed, and unfortunately, he was on my normal side of the bed. I went to the bathroom, washed my face, and brushed my teeth; when I turned off the lamp by the bed, Bryce asked me if he could borrow my toothbrush. He hated asking but was lying there feeling less than optimal as he knew he would have a muck mouth in the morning. I laughed openly -- "Bryce, first off, I would say go for it, but there is no reason you would have to use my toothbrush as Olivia has a drawer full to the left of the sink."

Bryce turned the light on his side of the bed and gave me a stern look -- "just for the laughing, I'm going to use your toothbrush." He got up, went into the bathroom, left the door open, and made a big show of using my toothbrush. I shut the bedside light off, so when he came out of the bathroom, the bedroom was dark. He went to crawl into the bed, but I had switched sides to my normal sleeping side. "Come on, Sid, that's not fair." I laughed again and told him it was the price for using my toothbrush; I also let him know that I was going to use one of the new ones in the morning, so he could use that one as his very own. He started laughing when he realized that by using my toothbrush, he was the one who was getting 'sloppy seconds' and that it didn't impact me.

He grumped as he climbed across me, barely missing my nuts with his knee as he settled in, he made it clear that I was likely going to be having him rolled up against me as he always sleeps on that side of the bed. I told him that was fine because if we switched places, I would be the one encroaching on him. We were out shortly thereafter. When my alarm went off at 6 AM I woke to find myself wrapped around Bryce with my morning wood firmly entrenched into the crack of his ass.

I made for my phone, but we were tangled in the covers together, and when I rolled his body came with me. I shut the alarm off and tried to disentangle from Bryce, who whined that he didn't want me to move and that he liked having me snuggled up to him. As the words left his mouth, he stiffened and went to pull away -- "Bryce, hold on. I woke up very concerned that I was plastered to your back, but if I'm being honest, I loved waking up with you wrapped in my arms. I'm sorry my cock is buried in your crack but again if I'm being honest, I can't say any of this is something I haven't dreamed about. You asked me not to move before you fully woke up, so I'm hoping that half-conscious response was the real you and not the one that was making to get away.

Bryce relaxed into me and pulled my arms around him -- "Fuck this feels right, I have been perving on you for a couple of years and I will admit I hated that douche nozzle you were dating; he was a tool and didn't deserve you. God, I hope you are a top or at a bare minimum very versatile because

I so want to feel you inside me at some point in the future." We agreed to snuggle for 10 more minutes, and that we would see where all this mutual attraction would take us. I will admit that I did cop a feel of his cock, as I pointed out to him it was only fair because he could feel what I was packing as it was wedged in his ass crack. I would estimate he was 8 inches and decently thick.

When the 10 minutes were up, I asked if he wanted to go first or second. He playfully responded 'both', okay, so he wanted to shower together; so, I pulled him out of bed with me and we showered together, exploring each other's bodies as we soaped each other up. I did use my cock to clean his ass crack -- it took everything I had not to sink my cock balls deep in his supple ass. If this worked out, I had hit the jackpot -- gorgeous, hard body, 6-pack abs light dusting of hair on a hard slab of pectoral muscles, and an ass I could get lost in for days. I did tell him that I'm not that versatile < and his smile fell>, but I quickly let him know I would only bottom for the right guy, but I prefer to top; he ate it up -- he was mostly a bottom and would top for the right guy on occasion. We both said in unison -- 'jackpot'

We dried each other off, dressed, and headed to the airport. We both used the same toothbrush for those who were wondering.

We checked the plane and finished pre-flight at 7:15 AM, which left us 15 minutes before everyone was supposed to arrive. We had an opportunity to talk about my ex, his ex, and what we were looking for in a life partner. We both realized what we were looking for in a life partner, the other exuded from every fiber of their being, and we were both more of 'take it slow and see how things develop without sex in the mix.' I asked him to bunk with me in the master suite, which he quickly agreed to. I did make it clear that if something happened between the two of us, I was interested, but I was hoping this could be a long-term thing. He agreed just as Olivia and the rest of the group arrived.

Everyone stored their carry-on as there was going to be a limited need for clothing. Before Olivia took her seat, she asked us how we both were feeling this morning. It was clear that she had peeked in on us on her way to bed and saw us intertwined together. I made it clear that it was none of her business, and Bryce turned red; 'excellent' was all she said as she made her way to a seat.

I got out of my seat, closed the cabin door, and armed it. I announced that Olivia and Alicia would be serving as Cabin Attendants on the flight. During take-off and landing, you need to be in a seat and buckled in; even though this was a private jet, it would be best to stay belted unless you were heading to the bathroom. I also let them know that if things did get bumpy, we would let them know to buckle up and stay seated. If that happened, Olivia and Alicia both knew how to stow things to prevent injury and damage.

As I closed the door, I heard Olivia yell out, 'Make sure you grab the right stick, Sid.' Bryce turned red again. I locked the door and kissed his cheek, letting him know that I found him completely intoxicating and that he needed to stop being quite so distracting. He simply blushed more. As we taxied out, I announced, "We will be leveling out at 41,000 feet and cruising at roughly 575 MPH, and the flight time would be right at 2 hours. For those of you who have not flown on a private plane, we will be flying higher than commercial planes as well as faster because we can fly more directly and not worry about commercial flight paths. So, sit back and enjoy the ride."

Bryce and I taxied forward, and as we turned onto the runway, Bryce announced, "Make sure your seatbelts are fastened as the captain will be putting us in the air very quickly." With that, I pushed the aircraft forward, and we were in the air, climbing quickly to 41,000 feet. When we leveled off, we engaged the autopilot so we could chat. It was crazy how easily the conversation was as we approached Belize airspace, it felt like 30 minutes had passed vs. the almost 2 hours we were in the air.

We went through all post-flight checks and had the plane set to take to the gang hangar my family rented in Belize. The plane would be refueled and checked while we vacationed. We headed through private aviation passport control and were in prearranged limos heading to the dock to grab the boat to the island. Bryce whispered in my ear -- 'In the past, I always stayed here in the city and never went with you to the island. I'm not sure how to act.' I turned to him, and kissed his cheek -- 'like you are someone I'm dating to see if this can last.' He turned red again, it was sweet watching him get so flustered; I was picturing him lying below me with his knees at his ears and my cock buried in his ass. Bryce squeezed my hand -- 'So you're picturing me naked with your cock in my ass, aren't you?

I can tell, your cock is too large to hide when it is erect.'

We arrived at the dock at that point -- Alex and the crew were there to take us to the island. They all shook my hand and welcomed the boss. Alex asked me if I was ok with the 'naked' weeks upcoming. I let him know I was not thrilled but would go along to get along. He let me know the two reluctant staff members were given a couple of extra weeks off so they would not feel uncomfortable. Finally, he made sure I knew that my room had been locked up and was ready for me to move into. I thanked him for his efforts and then asked why he was excited to see me naked. He blushed a beet red, even with his dark tan. I let him off the hook by telling him it was ok to look, he did ask me to introduce him to Olivia, as he kind of had a crush on her based on the interactions they had over the last month. I made the introduction, and they began talking about the activities and the upcoming 2 weeks. I found Bryce sitting out on the bow of the boat, sipping on a beer. I went to sit by him when the boat bounced through a wave, and I wound up sitting on his lap; I went to stand up, and he held tight -- "Sid, you feel good sitting there, you can stay put if you want to or not." I stayed put until we went through another wave and my ass cheek squished his left nut, so I jumped off his lap and offered to rub his nut which he politely declined because he did not want to get a hard-on...

We pulled up to the dock on the island and began to disembark. The employees on the island helped the 20 of us off the boat; as we gathered outside the main structure, Olivia reminded folks that when you emerge from your room, the only thing you should have on is sunscreen, sunglasses, and maybe a hat on but no clothes at all. This was going to be naked fun in the sun. I groaned audibly and caused a lot of chuckles from the group. "Okay, so I'm not a fan of being naked in front of other people. I was teased incessantly as I was growing up for being scrawny, a late bloomer, and needle dick the bug fucker. I'll suck it up and deal."

I walked off to my room with Bryce hot on my heels -- "Will you slow down, Sid? I can't imagine the baggage that comes with what you went through but let me clear up a few things for you -- You are fucking gorgeous, you have a body to die for, your abs have abs and those cum gutters will be the death of me and likely have me hard most of the two weeks we are here and if you tried to fuck a bug with that slab of meat it would wind up in your piss slit, not the other way around. When I saw you this morning in the shower, I was intimidated, but you are a great person, so I did not feel I had to worry about you looking at my little love handles or the lack of an 8-pack. I knew I could just be me and that was enough. I will make sure you know that you are enough just the way you are and honestly even if you were scrawny and had a little dick, I would still be all over you because I like you the person." "You keep that up and naked fun will not be in the sun, it will be me chasing your sexy ass around the room."

We put our few clothes and toiletries away and stripped to our birthday suits. I jumped in the shower and washed the travel away. Bryce joined me. We made out for what seemed like 5 minutes but wound up being about 30. God, he is such an awesome kisser. We dried each other off and applied sunscreen SPF50 to each other, and then headed to the pool. We were the last two to arrive at the pool and as we walked in everyone turned to look at the two of us, I was convinced it was Bryce they were looking at and I'm sure they were but Doug, Alicia's fiancé whistled and a cat called -- "Sid, damn all of that bloomed late, you certainly are not scrawny and I would venture to guess the bug would be squashed by that monster cock swinging between your legs. To be clear, your former classmates are assholes and you have a great body but what sets you apart is your personality and love of your friends -- look around we are all here because of your generosity, never lose you." He jumped up and hugged me, I think he forgot we were both naked because he stepped back and chuckled -- "well color me stupid I forgot we are naked, that is not something I have experienced before."

Alicia was watching all of this carefully and asked a pointed question -- "So Bryce, where did you change? Your room is next to ours, and I didn't see you go in or come out." Bryce was turning red and looking for a place to hide, so I did the only thing I could think to stop the inquisition from getting underway, I grabbed him and pulled him into a deep, passionate kiss, and we got lost. Olivia was screeching -- "See Al (Alicia), I told you the two of them were meant to be. I'm so glad that those assholes are gone. They didn't deserve either Sid or Bryce." When I stopped kissing Bryce, I realized we were both fully erect, well fuck it, this is supposed to be naked fun in the sun. I turned around and found two lounge chairs.