Sizequeen Resort Pt. 01

Chapter 1

"Are you sure you want to do this?"

Rachel looked at me with her deep brown eyes while playing with her hair visibly a little uncomfortable.

"I thought it could be a great chance for us to both have a great vacation and explore our sexuality... but if you don't want to go is fine."

I smiled back to her trying to stay natural, but I was incredibly uncomfortable as well, driven only by pure lust.

"But you know, it's an incredible place just take a look at these pictures, isn't this the best beach you have ever seen? We can completely avoid all the kinky staff if you want."

Between us, laying on the bed, there was my computer, open on the "Sizequeen Resort" website, one of the world's finest in term of sexual tourism.

"I don't know Jack, it truly looks incredibly fancy, but I have so many questions. Can we afford this? Are you sure you want to indulge in this fantasy of yours? Is it liking a safe space? What if someone sees us?"

I immediately started holding her hand. Her puppy eyes showed more fear than excitement, but I was too deep on this project at this point to give up.

"Cutie pie calm down, it's going to be fine. I thought about everything: the place is very well known for its safety standards and privacy so don't worry about it; a thorough process is used for admitting every single client. Yes, security and privacy come with a price, but we never celebrated your graduation from college, and I am ready to spend a little more for some holidays this year. We can easily do that at the beginning of April to avoid the busy season, even though I doubt we could ever meet some friends of ours in such a tropical island."

I took a deep breath a started caressing her chestnut hair, making eye contact with her for the first time since the beginning of the conversation.

"Plus, we will both simply enrol as swingers, the place is very sex friendly, but of course nobody will force you to do anything, if you won't feel like it we will simply have a great time in a tropical paradise."

"I mean if you put it like this..."

She moved away from my hand and took the computer, scrolling focused on the beauty of the enterprise.

"What is a size queen?"

As she innocently asked the question, she leaned forward to the computer showing off her incredible cleavage, a DDD cup if not an F, which I couldn't avoid glazing at, as always, sparking new waves of excitement in me.

"So, the peculiarity of this resort is that only very endowed men can join as swingers or bulls. When we started fantasizing about this kind of stuff, we both agreed that someone big would have been perfect for trying this kind of lifestyle, so I thought..."

"And are you sure you could pass the bar?"

Rachel knew I liked SPH, but this time it was not done on purpose in a sexual context, but a genuine concern. The honesty of the question truly made me feel humiliated, but I was aware that my scarce 15 cm had no chances to be considered for a swinger role, let alone a bull position.

"We will have to send some pictures, worst case scenario I will have to sign up as a cuck. A little bit kinkier for us, but in the end this is the reason I would like to go and everything else I said before would still apply. No sex if you don't want to!"

"Alright, alright, you won. Let's do this. But you could have told me before! April is in one month and I am fat."

Rachel threw the computer away and started checking herself in the big mirror next to the bed. She was 1.65, slightly chubby, but in a way that simply made her hotter. She was an Angela White type, only a bit thinner and with a latina type ass. It was incomprehensible for me that she had just a glimpse of insecurity, but probably if it wasn't for that, I could have never pulled her off.

I got immediately up and hugged her from behind, gently kissing her neck.

"You are not fat; you are beautiful, and you know it. Actually, I think you should get fatter in the next month, otherwise everybody inside the resort will only have eyes on you".

She chuckled tightening the hug and gave me a big kiss on the lips.

"You know I love you so much."

"I love you too."

And so, the deal was struck. By the end of the day, I had rented a room for two for three weeks and sent all the necessary documents for registration, with Rachel helping me to take some dick pics trying to make it look bigger than it actually was. It came as no real surprise the mail that came a couple of days later informing me that: "Unfortunately I did not fit the requirements for the position I applied to, but I was more than welcome to try the other options.".

At the end we both knew that complaining was useless and we decided to go for the package "Introduction to cuckolding" thinking it was the softest options for newbies like us. It was only way later that we found out that that was actually quite the opposite. To be frank if I had known from the beginning the full extent of such a bundle, not even my deepest impulses would have made me accept it.

The following month went by pretty quickly, we were both very busy at work, as per usual when someone just started a career and wants to take two weeks off.

Our sex life was arid, as usual. Ever since I had decided to confess to Rachel my fetishes, she had agreed exploring them with me, but it was pretty clear that it was more for the love for love than lust. The amount of time we had sex had since then diminished significantly, and it was safe to say that in the 30 days preceding our departure the act was performed no more than once a week with no reference whatsoever to the adventure approaching.

Chapter 2

We started our journey early morning as planned. The trip was extremely long, starting from Europe and changing 2 planes before arriving in a small airport in a Caribbean Island.

Travelling first class, this part of the trip was quite pleasant despite being nearly 24 hours long. I was incredibly excited, the idea of finally giving into my lifelong cuckold fantasy kept me awake at night and hard most of the trip. Rachel was excited as well, but only about the beaches and the sunset she had seen online, for this very reason that was the only part discussed during our hours of travelling. It was quite clear to me that, for the time being, leisure was all she was planning for.

Arrived at destination surprisingly refreshed we took a cab for 4 hours that lead us to a small private doc owned by the same company of the resort where a young guy, surely local and unable to speak English, showed us a motorboat.

At the dock we also met a couple waiting for us going in our same direction.

We briefly introduced each other with a bit of awkwardness before starting our sea trip, hurried by an impatient captain. The sound of the waves was too loud for us to talk but we still got the opportunity to do a bit of small talk.

His name was Dan, early thirties, surfer vibe, long blonde air, well built, tattoos covering his veiny arms and a smile maybe even too white, rocking a white tank top and some short jeans.

Her name was Lana as she surely was incredibly hot: she fit the vibe of her companion, long blonde hairs, a white tank top clearly that revealed her small perky tits, similarly her very skimpy shorts left little to the imagination regarding her incredibly toned ass. She was really showing off her body, and she had reason to do so.

Compared to them we were actually a bit funny, they were incredibly energetic and looking forward to the resort, laughing every two words, while we were quite tired for the trip, still wearing the casual clothes we arrived in, no more than a t shirt and a pair of jeans for me and a top and skirt for my love, which was being quieter than usual.

Finally, we arrived a destination. On the small wooden dock, a bald guy full of muscles wearing nothing but a pair of swimming truck was waiting for us.

"Welcome! Welcome to paradise! I hope you can forgive my attire, but I just came back from a surfing class, and I had no time to properly dress up. I hope you all had a nice trip."

With the warm smile of a true professional he helped us exit the boat and started leading us to the reception.

It was almost lunch time; the sun was shining bright over the bright white sand and dream-like sea. In front of us, surrounded by a deep vegetation, a wooden fancy-looking building was the only thing visible surrounded by a deep vegetation.

I held Rachel's hand as we started walking on the stone path leading to the entrance as our host started explaining.

"Welcome to the size queen resort! I am Daniel and I will be responsible for your enjoyment of the next two weeks. Feel free to ask me for anything at any time. All the facilities are on the other side of this building hidden to the boats passing by in order to preserve the privacy of our clients. For this very reason on this side of the island clothes are still mandatory and phones are allowed in case of necessity during your stay.

I am sure you have all read the rules online but here is a bit of a refresher: sex is allowed in all parts of the establishment, consent is always a must, any wrongdoing will not be tolerated, and any transgressor will be signalled to the local authorities immediately."

He stopped and smiled to both me and Dan.

"Boys, I cannot say it enough, please hold your horses, I am sure you will have plenty of fun anyway".

Dan grinned back nodding playfully.

"No kind of clothing is required on the other side, only requirement is that male dicks should always be visible to showcase whether they are bull, swingers or cucks and their relative accessory, but I am sure you all read it in the extensive briefing Jennifer sent you."

My heart sank. Briefing? What briefing? I looked at Rachel in search of explanations, but she kept her head low purposely avoiding my eye contact. Something was going on.

"Waiting for you on the other side there are 12 swinger couples and 1 bull, while we are still waiting for another couple of swingers and a hotwife with her cuck. As you can see the number of sexually active male and females is purposefully kept the same."

We reached the entrance of building where a beautiful brunette was lazily typing behind a computer.

"Now the beautiful Jennifer will check you in and after I will gladly show you around. In case you did not follow the hygienic standards mandated by company rules she will help you with that, but as your all swingers I am sure there will be no problem with that".

"Actually..."

I spoke up unable to look at Daniel straight in the eyes.

"I think we registered as a cuckold couple..."

The low chuckle from Lisa was immediately covered by Daniel immediately running to repairs checking paper after paper from a pile on the desk.

"Oh my, oh my, I am so sorry... Jack. There must have been a mistake, I thought you two were coming tomorrow. You subscribed to the... just a sec... introduction to cuckolding package... right right... I see that the lovely Rachel completed all the preparatory training wonderful, did you tell anything to your hubby?"

"Not a word as instructed."

I looked at Rachel speechless as she snap replied. She looked at me with a guilty face and put out her usual angelic smile.

"I did it for you, I know how much you wanted this."

"Wha..."

"Relax, relax, I know you must be really confused, this was not supposed to be the way I welcomed you, but it will be easily fixed. Now Ajani will take care of your bags, ladies please come this way into the changing room on the left while boys go with Jennifer on the right. The bureaucratic part will have to wait."

Without a second to think Jennifer brought us in a big changing room where Dan immediately started removing his clothes.

"I will be back in a second."

Unsure to what to do and still processing what was going on I stayed still, my eyes looking in the void. Well, my eyes looking at Dan more than the void. He had removed the two clothes he had on and was now proudly showing off his ripped, skinny body and his huge soft cock hanging between his legs. I tried not to stare but it was the biggest thing I had ever seen live, maybe bigger soft than me fully hard.

"Scared to show your worm, eh? No point in that soon it will be on display for everyone".

I looked at him trying to gobble up an answer.

"I have been vising this place every summer for the last 3 years and I have seen no more than 4 or 5 cucks and they were all deep in the lifestyle. I am very curious to see how you will be introduced to it ahaahahaha."

He gave me a strong pack on the back and headed for the exit without waiting for Jennifer to be back.

"I will enjoy every second with your girl, she is surely a nice piece of ass. So sad you cannot satisfy her."

Another laugh, this one more humiliating than the first.

And with that he left me all alone in the room. I was speechless, everything had happened so fast. Rachel had gone through a month of preliminary training; Dan has changed his attitude towards me in a matter of second and I had to do through some mandatory "sanitary procedure" I had no idea of.

As I was processing all this kind of information I undressed and waited naked for Jennifer, my hands covering my limp dick.

"Here I am, here I am. Very sorry for the delay."

Jennifer showed up wearing a skimpy red two piece. I looked at her like I looked at my first crush. Her body seemed to have been carved by God himself, or maybe a pimp. Big fake boobs, flat stomach, perfect bubble butt, toned body and perfect tan created by her lifestyle.

"Good hubby, I see you already got naked, please make it easy on me.

So, let's see what Rachel have to work with every day."

She took my hands and exposed my now semi hard dick.

"Yep, why did you say it's 15 cm? it's not good to lie! Anyway, now that I see this I understand perfectly why you selected this package. Now please respond to my question with a simple yes or no, you will have time to ask whatever you want whatever you want at the of the process. No worries for your love, Daniel is simply showing her the facility, she will wait for you in the room, and nothing will happen to her... unless she wants to. Understood?"

I felt her natural dominance and replied submissively.

"Yes."

"Nah, nah. Rule number one, in this island respect is important, as you are the beginning of your cuckold journey you will refer to anyone as ma'am and sir, understood?"

"Yes ma'am."

"Good hubby, now I read here that your girlfriend told you nothing about her preparatory exercises and the modules she filled in the past week, correct?"

"Yes ma'am."

"Goood. Did she share with you any information about the life in the complex?"

"No ma'am."

"What a good girl. I read here in your file that you have deep interest in cuckolding, sph with possible bisexuality and feminization, correct?"

"wha.. who told you th..?"

"CORRECT?"

"Yes ma'am."

"Good, good. you are the first couple who choose this bundle in a long time. I really can't wait."

She took a moment and started looking intensely at my body before starting again to write down on her notebook.

"Body skinny-fit, ass: fuckable, cock: 3 cm soft, caged suggested: try micro, fairly hairy. Information sent by wife: confirmed."

She showed me a long, thick-written form.

"You have subscribed to the "introduction to cuckolding" bundle, by signing this you agree to take part in all the activities included in the program with the ability to refuse only the ones not pre-approved by your partner and you wave the resort any kind of legal liability."

I looked at her like a deer in the highway, unsure of what to do. Too much information, too fast. my dream was coming true, but so much so that I was finding myself incredibly scared.

"Listen I know, this can be overwhelming."

For the first time since we had met, she was using a calm and reassuring voice.

"But if I understand correctly this is a big dream of yours and your girlfriend went out of her way to make it true. She knows everything which is about to happen, and she acknowledged and approved it. Do you trust her?"

She was right, Rachel would have never approved anything against my and our best interest.

"Sorry, it's just a lot.

Can you hand me the pen?"

"You did the best choice Jack! I am sure you will both have the best vacation of your life! Now we don't want to make your lady to wait too much, so allow me to introduce you to the resort. While I will be explaining I will start applying a lotion to your body, is it ok for you?"

"Uh.. oh... yes?"

"Thank you Jack you are making this very easy for me. Now please open your legs wide like this and put your arms parallel to the floor. Like this, great. Let us start from the hygienic requirements and wearable gadgets as you are in the middle of the process. We require our visitor to follow some considerably basic rules regarding appearance in order to allow everyone to easily recognize the role of each one and avoid bad accidents during daily activities. As you were told, we are in low season and nearly all the guests are swingers, still rules are rules, and we expect everyone to follow them. Instructions are quite simple: male swingers are required to be well trimmed and you will see them wearing a very thin cock ring, female swingers are required to be fully shaved and to be wearing a gold ring on the right toe as well as a gold bracelet on the right arm. Our shop also offers a temp-tattoo service for our kinkiest clients."

While she was speaking, she had finished covering my body and my skin was now starting to itch slightly.

"Now please stay still 2 minutes, then go wash over there."

She pointed at one shower stall in the angle of the room.

"For bulls, the rules are a bit different, but for your stay there should be only one, named Jacob. I think you will have no troubles recognizing him. He will be here tomorrow afternoon. Same thing applies for single women, they are very rare, and we are very selective with them, if someone books I will let you know".

She could not help but stop and chuckle a little bit when talking about Jacob, at the time, given the amount of information I was receiving, I didn't really pay too much attention to it.

"Which leads us to our final category cucks and hotwives, well in this case hotgirlfriend. Ladies are required to be completely smooth as for the swinger, but they need to keep a single strip of air on the pubes. Your Rachel actually did it on her own."

"For real?? Why didn't she tell me, she knows I love it! I would have loved to fuck her pussy like that at least once before coming here."

I thought to myself.

"When you join her in your room, she will be also wearing a silver chocker and a silver bracelet on her right ankle.

While cucks..."

And there she took a pause and looked at me in the eyes with an amused grin.

"Well, you need to be completely hairless, and your dick must be put in a chastity cage at all times, while you are outside of your room, unless agreed by all people staying in the same area as you."

"W-what? Is that necessary? Did Rachel agree to this?"

"I know it can be surprising for you, usually cucks come well aware of this requirement. This is a great moment for me to explain the first motto of our establishment: "women like it big". As this resort revolves around REAL pleasure, we don't want any little thing like that to roam freely. We had past guests who couldn't resist the passion around them and started jerking off unsolicited. Here we consider it as molest behaviour and I don't need to explain to you our policy for that around here. It is also important to add the importance of such a tool for the program you enrolled in, you will learn a lot and I am sure you will get quickly accustomed to it. So yes, it is necessary, and Rachel agreed to it."