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 at her, trying to stay natural. Still, 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, lying on the bed, there was my computer, open on the ‘Sizequeen Resort’ website, one of the world’s finest in terms 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 like 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. Still, 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 on 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 enroll as swingers. The place is very sex friendly, but of course, nobody will force you to do anything. If you don’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. Still, I was aware that my scarce 15 cm had no chance of being 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 to me that she had just a glimpse of insecurity. Still, probably, if it wasn’t for that, I could have never pulled her off.

I got up immediately 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. I 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.’

In the end, we both knew that complaining was useless, so we decided to go for the ‘Introduction to Cuckolding’ package, thinking it was the softest option 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 usual, when someone just started a career and wanted 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 to explore 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. 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 two planes before arriving at a small airport on a Caribbean Island.

Traveling 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 for 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 traveling. It was quite clear to me that, for the time being, leisure was all she was planning for.

Arriving at our destination, surprisingly refreshed, we took a cab for four hours that led us to a small private dock owned by the same resort company. There, 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 to go in the 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, and she surely was incredibly hot: she fits the vibe of her companion, with long blonde hair, 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. At the same time, we were quite tired from 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 quieter than usual.

Finally, we arrived at our destination. On the small wooden dock, a bald guy full of muscles wearing nothing but a pair of swimming trunks 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 dress up properly. 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 lunchtime; the sun was shining brightly over the bright white sand and dream-like sea. In front of us, surrounded by deep vegetation, a fancy-looking wooden 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 from 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 signaled to the local authorities immediately.”

He stopped and smiled at 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, the 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 one 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 males and females is purposefully kept the same.”

We reached the entrance of the 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 you are 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, who ran to repairs and checked 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 the boys go with Jennifer on the right. The bureaucratic part will have to wait.”

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

“I will be back in a second.”

Unsure of what to do and still processing what was going on, I stayed still, my eyes looking into the void. Well, my eyes were 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? There’s no point in doing that soon; it will be on display for everyone.”

I looked at him, trying to gobble up an answer.

“I have been visiting 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, aha aha aha.”

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 had changed his attitude towards me in a matter of seconds, and I had to go 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, a flat stomach, a perfect bubble butt, a toned body, and a 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 has 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, no. Rule number one, on this island, respect is important; as you are at the beginning of your cuckold journey, you will refer to anyone as ma’am and sir, understood?”

“Yes, ma’am.”

“Good hubby, I read here that your girlfriend told you nothing about her preparatory exercises and the modules she filled out in the past week. Correct?”

“Yes, ma’am.”

“Good. Did she share with you any information about life in the complex?”

“No, ma’am.”

“What a good girl. I read here in your file that you have a 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 have chosen this bundle in a long time. I really can’t wait.”

She took a moment to look intensely at my body before starting again to write in 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 on the highway, unsure of what to do. There was 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 about it, and she acknowledges and approves 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 made 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 wait too long, so allow me to introduce you to the resort. While I am 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 with the hygienic requirements and wearable gadgets as you are in the middle of the process. We require our visitors 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 for 2 minutes, then go wash over there.”

She pointed at one shower stall at 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 trouble recognizing him. He will be here tomorrow afternoon. The same thing applies to 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.

“This leads us to our final category, cucks and hotwives, well, in this case, hot girlfriends. 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 also be wearing a silver necklace 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 molesting behavior, 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.”

I looked at her with my eyes widened. I was speechless. I had fantasized about chastity and bought one for a while when I was younger, but exposed like this? in front of everyone?? Fuck, what I had signed myself into. Crazier than that, the fact that Rachel knew all along, agreed, and did not tell me anything about that.

“S-so you need to shave me off?”

She looked at me like I was the dumbest person on earth.

“What do you think we just did? Come on, go, and wash yourself off. Unbelievable.”

Now, I actually felt pretty dumb.

I quickly moved to the stall and started showering with warm water. While the lotion was being removed, my hair came off with her. In the end, I felt my soft, hairless skin. It felt like Rachele’s skin whenever she went to the beauty salon. Only this time it was me. Suddenly a rush of blood went directly to my cock, making him extremely hard and sensitive. Jennifer looked disappointed in my naked body.

“You see, I am glad you are enjoying this, but it clearly shows why this is necessary.”

While pronouncing these words she raised her right hand where she was holding what was a very small chastity cage. It was made of metal, with a lock included inside the ring and a cock part no longer than 3 cm, maybe shorter.

“Do you need some ice, or can you exert some self-control?”

I looked at her, ashamed; I must have been looking truly pathetic, excited from my very feminine skin and soon to be locked up in chastity.

“Actually, some ice would help.”

“I knew that, no worries. You are just at the beginning of your journey, and soon, you will learn how to behave. Now, take the ice to the cage. Suppose it is OK for you in the meantime. In that case, I will give you some basic info about the program you enrolled in and the basic activities inside the resort to distract you a bit.”

“Agreed.”

“Well then, every couple has its bungalow where they can rest and have some privacy. You are, of course, more than welcome to have visitors if you so decide. The resort, as you saw on the website, comes with multiple beaches, a restaurant, a cocktail bar, a spa, two pools, and a gym. Special activities are offered daily by our staff, and you can ask for food and drinks from everywhere on the island. You are free to plan your days as you want, but, as for your package during your first week, you and your partner will be required to take part in some tailored activities; it will not take more than 2-3 hours per day. No phones are allowed inside for obvious reasons. Sexual activities are allowed all over the facility, but please don’t ask the staff to take part in them.”

She pauses, hearing the click of my now-secured device.

“Even though I don’t think I will need to remind you of this, let’s go, shall we? We reserved you and Rachel the bungalow closest to here. It’s less than two minutes by foot, and I think that if you move pretty fast, we can avoid meeting the others, as they should still be having lunch. I am sure you and your loved ones have much to talk about.”

“Yes, please, let’s go.”

I put on a pair of flip-flops and quickly followed Jennifer outside the same door that Dan had used 20 minutes before. I wanted to look around me, but I was too embarrassed to look away from the sand in front of my feet. Too much information to process. Crazy to think that I wanted to introduce Rachel to cuckolding, and now, apparently, she knew more than me, and I was the one to be taken step by step.

After just a couple of steps, I could hear a female voice moaning and some laughs and cheers, which for the first time, made me aware of the restriction on my dick and forced me to walk faster.

As promised, I was soon in front of a very fancy bungalow next to a white beach. Normally, I would have taken my time exploring all the single details, from the patio to the recliner outside, but not now. I rushed to the door and opened it like a fury.

And suddenly, everything else disappeared.

She was there, as beautiful as ever, laying on the bed completely naked except for the chocker and the bracelet.

She looked at me with the purest smile and a lusty smile.

“Finally! Are you happy? Look at what I planned for you!”

I immediately noticed she was incredibly wet and that she was fingering herself. All my rage, my doubts, and my confusion disappeared in an instant and got replaced by a sentiment of complete lust.

“I am so happy, love; I can’t believe you did it all for me.”

“I was hoping you would have appreciated it; it’s like your fantasy, right?”

“Yes, and even more love!”

“Come here. I need your tongue so much.”

Without adding a word, I crawled onto the bed and started licking her furiously. I had never seen her so wet; fluids were pouring, and she started moaning immediately. Her right hand was caressing my head. My nose could feel the curated body air on her pubes. Instinctively my hand rushed for my dick but only found the metal protecting it. The rush of adrenaline forced me to focus on her pleasure, and soon enough, I could see her moaning harder and harder.

One, two, three orgasms in rapid succession.

“STOP, Stop”

She demanded after no more than 10 minutes.

“Wow, baby, which was so intense, maybe the best orgasm… ever.”

She rolled to the side, taking a breath while I put myself seated, my face full of her fluids.

“Ahem.”

“Oh, my baby, I am so sorry! I forgot they put you in chastity; here, let me take it out for you! It must have been so hard for you.”

As she swiftly made the mechanism work, my dick got free and instantly erected.

“OK, let’s solve this, and then we talk, right?”

“Yes, please, baby!”

Smiling, she got her on her knees, ready to start sucking it off, but it wasn’t necessary. After just two strokes, my cock erupted, giving me the best orgasm of my life.

“Well, that was easy.”

She chuckled.

“I must assume you are not really angry with me.”

*****

Chapter 3

I lay down next to the love of my life, and we started cuddling in the midst of post-orgasm bliss.

She was the first one to break the silence.

“So, you are not angry with me?”

“Why should I be?”

“I lied to you.”

“I brought this to myself, didn’t I?”

“Yes, you did, but still. I know it is a lot.”

I sighed. It was, in fact, a lot. But in that moment, nothing mattered; we were together, and I was in peace.

“I guess sometimes you have to be careful of what you wish for. I am so glad we are doing this together, though.”

I hugged her tightly.

“So, what else do I need to know.”

She chuckled.

“Oh, they sent me a lot of material. I truly think this first week will be very educational for the two of us.”

“Ooh, look at you, the experienced hotwife.”

“Oh, I am pretty sure I know more than you.”

“And did you like what you found out?”

“Mmmmh, a little bit.”

She said it in a lusty voice. I could see she was getting excited thinking about it.

“I still can’t believe this was a big fantasy from the get-go! Are you sure you are OK with this? You know, with me and other men…”

“Yes, babe, I really want to test it out together. Come on, it’s only three weeks.”

“Yeah, sure, only three weeks…”

“So, spill the tea. What do I have to expect in these coming days.”

She escaped my hug and sat in front of me, her boob jiggling right in front of my eyes. Her eyes were now full of energy.

“So, yes, they give me instruction on what to tell and not tell you. Trust me, it’s all for the sake of the experience. If you are not comfortable with something, you just tell me, and we stop, OK?”

“Very clear.”

“So, the first thing is that when we are outside, you have to call me mistress, and I will call you hubby.”

“Oh, wow, kinky.”

“Understood, hubby?”

“Yes, mistress.”

I chuckled. It was so hot and weird.

“Shall we discuss the rest in front of some lunch?”

“Yes, please. I am actually starving.”

“Let’s go then! But remember to put back on your cage.”

“Oh, right.”

The small metal object was still lying on the floor, far from the bed.

“Is it comfortable?”

“Sigh, I will get used to it”.

“Good. You know cucks are better locked.”

I looked at her in shock. Was this my girlfriend? She noticed my expression and shrugged it off with a laugh.

As I was sitting on the floor readjusting my cock in his new home, I saw her getting dressed in the glimpse of an eye.

When the work was done, I looked up at her and was amazed by her beauty. She was wearing a gold bikini, the same color as her jewels, that truly accentuated her curves. On top, a semi-transparent beach robe completed the outfit.

“Like it? It’s only missing one thing.”

She said while spinning for me. She took the key to my cage and attached it to a chain that she put around her neck.

“So now it is perfect. I feel so hot! Well, for you, it’s going to be a bit more difficult. I knew most of the clothes you were going to bring were going to be useless, so I took the liberty to bring some more. You can either go outside naked, which I know is a pretty common solution for the boys around here, or you can try this crotchless boxer swimsuit with a shirt on top.”

The choice was pretty obvious. Despite the lack of privacy, there was no way I was going outside fully naked. I prepared with the outfit suggested and made myself ready to venture outside for the first time.

“Come on, let’s go; the dining hall will probably be empty by now.”

“I truly hope so.”

She took my hand and set foot outside. Her, a goddess, looking as sexy as ever, and me, with my compressed cock hanging between my legs exposed to the world.

I tried not to think about my situation and followed her.

“So, all the people of the island know that I am out of access for this first week. The organization stressed that it is very important for us to do the classes first in order to get in the right mindset.”

“Oh, so we have… classes?”

“Sort of.”

“OK, good to know.”

“Still, there is no need not to be friendly.”

“Right, I guess.”

“Common, nobody is going to care about what’s under their trust me. It’s going to be fun!”

“Alright, alright. Never been a party pooper, not going to start now.”

“I think we could sit here.”

She indicated a table near the dining area with two recliners, a bit apart from the main area and closer to the sea. Luckily, she was right, and nobody was around, even though I could see some silhouettes far away in the ocean.

“So, you click here.”

She said while pushing a button on the recliner.

“And the waiter arrives in 3 mins.”

“Oh wow, what a luxury.”

“Best gift ever!”

She chuckled while sending me a flying kiss.

“So, let’s address the elephant in the room. Jacob will be our trainer for this first week.”

“Wha..”

“Yes, the bull coming tomorrow was actually kind enough to spend the first week of his vacation teaching us the cuckold lifestyle and more.”

I looked at her, speechless. I know we were going to do it, but like this? A trainer? For a full week?

“Two salads and two glasses of water, please.”

Rachel ordered carelessly from a guy who materialized behind me.

“What?”

“You don’t want salad?”

“Don’t play dumb with me.”

“What? It is an “Introduction to cuckolding” What were you expecting?”

“I mean, I thought we would have taken our time.”

“And we will hubby! That’s why we have a trainer!”

“Who is even this guy?”

“Oh, no worries, I went through some rigorous selection process.”

“YOU CHOSE HIM?”

“I am not going to go with the first random guy that comes around!”

“Oh well… why didn’t you tell me??”

“You know why! It was part of the program!”

“Off, I can’t even be mad at you.”

“Yep, you planned for it. Oh, look at our salads.”

I looked at her, grabbing a first bite. That was my idea all along and now she was the one trying to convince me.

I followed suit, too hungry to complain.

“So, what can you tell me about this guy?”

“So., so… so…”

She said enthusiastically, maybe a bit too enthusiastically.

“His name is Jacob, he is 35, and he has 15 years of experience as a bull.”

“Oh wow, he started young.”

“He surely did. He is a fitness model now.”

“Oh wow, you choose it well.”

“I surely did. Don’t be jealous, or maybe be.”

She chuckled with a mischievous grin.

“Choon honey, don’t make that face; you know you are the man of my life. It will only be sex.”

“Yes… I know.”

“I thought you wanted to see some big cock filling this pussy.”

I felt blood flowing to my dick. At least it tried. A weird flow of excitement went through my body, my dick tried to get hard, but the cage was so tight that it didn’t move an inch. It was a new and unique sensation. I instinctively tried to grab my dick, but once again, I found my cage there. I tried to shrug it off carelessly by pretending to be adjusting, but it was very clear what had just happened.

She chuckled, clearly amused.

“You know, I have never seen you reacting like this; it is so weird. How is it that you would like me to have sex with someone else?”

“I don’t know, actually. It’s a deep desire I have had for as long as I have memory. Maybe it is related to the fact that I see someone I love feel good.”

“That’s actually very sweet.”

“You know it is so weird for us to talk about something like this so freely.”

“You don’t like it?”

“It’s actually… liberating.”

“I am sure we will learn a lot of things about ourselves this week.”

I smiled at Rachel; our meal was over. A heavy weight was removed from my chest. I looked around: the sun was shining, and a slight breeze was coming from the sea. Still, no one was in sight.

“Come on, let’s go sunbathe!”

I got up refreshed.

“Yay, let’s go enjoy this paradise!”

She followed immediately, but we didn’t go far. I was still worried about finding other people, so I opted for a deck chair 10 meters from where we were staying. We both got covered in sunscreen, always available in any corner, and placed ourselves comfortably, her facing the sun and me lying face down, trying to hide my exposed cage.

After no more than 5 minutes, I fell asleep, tired from the roller coaster of emotions.

“So, you are Rachel. Very nice to meet you!”

A deep voice woke me from my dreamless sleep.

“The pleasure is mine, Matias.”

I turned my head, confused, trying to understand what was going on. Next to me, Rachel had woken up and was striking up a conversation with some new people.

“Oh, so sorry we woke you up. I am Matis, and she is my wife, Julia; we just wanted to come and introduce ourselves to the newcomers.”

Matis was standing naked; he was clearly South American, with big arms and a bit of belly fat but a very funny and reassuring face. Like everybody else, his huge soft dick was swinging between his legs, maybe even bigger than Dan’s. Julia, right next to him, was gorgeous, light-skinned, with curly black hair, beautiful puffy lips, perfect C-cup breast that she was showing proudly topless, and her perfectly shaped ass accentuated by a white thong.

“Oh, no worries at all, I am Jack; very nice to meet you.”

I got up, trying to shake his hands.

“Ooh, you are the cuck! I heard a hotwife had arrived today!”

“Yes, that is… us.”

I stood up, my caged dick right in front of his huge member was a pathetic vision, but now it was too late to go back down.

“Oh my, what is this? Does it hurt?”

In a glimpse of curiosity, Julia got closer to my chastity and started examining it carefully.

“You could never fit that, right, love?”

“Julia, please show some manners!

I am very sorry for my partner; she is too often without filters.”

Matias grabbed her by the arm and forced her back.

“Nono, it is a legit question. It will be on display for the next few days, so it is better to avoid any kind of rumors from the get-go; plus, I think it is important for you to stop worrying so much about your situation down there, right hubby?”

Rachel had taken the lead of the situation.

“Yes, yes you, you are right, love.”

I felt a soft kick on my leg.

“I mean mistress. So, this is a chastity device; I am not allowed to roam around with my cock freely; management says it is for avoiding unpleasant situations. And yes, but very slightly, only when I try to get hard.”

“Oh woooow, that is so interesting. And who has the key?”

“Right here!”

Rachel pointed it out proudly.

“Wow, you are the owner of his dick! I should buy one for you, sweetheart.”

“You can forget about it, haha.”

“You are always so boring. But you, Rachel, you are truly a powerful woman!”

“Thank you! It is the first time someone has told me something like this!”

“Impossible, you can control your man! I always try, but then…”

She started caressing his dick going in a second from incredibly energetic to extremely excited.

“Julia, not now, please. You truly don’t know how to behave”?

“I am sorry, cutie, it’s this island. We are having so much sex, and it is always so good. Plus, you know that in a week, we will have to be back to our boring lives.”

“I know, I know, but we did it less than 30 minutes ago; give me a rest.”

“Alright, alright. And Rachel is having fun as well?”

“Actually, we arrived this morning; we took part in the “Introduction to Cuckolding bundle,” so for our first week, we will just have activities that will help us set the mood and understand the lifestyle.”

“Ooh, you are sooo lucky, you just arrived. That’s why you still have so many clothes on. Don’t be shy. Having a total body tan cannot be against the rules!”

Rachel looked at me and smiled.

“You know Julia, you are absolutely right. Hubby, can you help me with this? I have always wanted to get a full body tan.”

She got up and gave me the back while facing the couple. I submissively untied the back of the bra and let it fall on the sand allowing both of them to have a clear view of Rachel’s beautiful boobs.

“Oh wow, are they natural?”

This time Matis was talking; once again, I felt the same type of excitement going throw my body and my cock pressing on his tiny home.

“Yep, all natural.”

“You are a very lucky man, Jack. Are you sure you are off-limiting this week? Ah, hahaha”?

“Hey, who would I be supposed to fuck while you have fun???”

In a second, I was completely left out and buried in excitement.

“Come on, Jack, I am joking, I am joking. But you surely have a wonderful girlfriend. Here, let me offer you a beer to forgive this unfortunate choice of words right away.”

Matis padded me on the back and called the waiter for some refreshments.

He made some space next to me, and Julia ended up sitting next to Rachel.

For the rest of the afternoon, we actually had a great time just chatting with them, nothing sexual, apart from some comments from the girl about the great endowments of his partner. They told us they were photographers, about their travels, how they found out about this resort, and how every year they come for three weeks to take the steam off. They told us that the island was bigger than it seemed. With so few people, we could expect to see hardly anyone during the day, information that visibly disappointed Rachel. Still, during the night, most couples would eat out in the dining area, the most fun part of the day, as the dinner would often transform into an orgy.

As the sun was setting, they excused themselves, as they had another couple to meet for some wild sex, and accompanied us to our room.

“Did you see how big his dick was?”

Rachel asked as soon as she closed the door.

“Yep, do you want to go for dinner?”

“Dinner can wait. We have our first activity to perform together.”

“What, really?”

“Yep, you know we have some every day.”

“Oh, so we are going somewhere?”

“Nono, it’s just us here.”

As she was saying that, she hugged me from the back, kissing my neck, her naked breasts pressing on the back of my body. Shivers went through my body.

“How big do you think it was?”

“I… I don’t know… maybe 19 cm hard”.

“I think more. Did you hear how Julia was talking about it? I bet he can fuck her so good.”

“Yes, I heard it. She surely loved it.”

My knees were starting to get weak; the feeling of lust was increasing every second.

“Do you think you can fuck me that good?”

“I know, I can have my performances.”

“That is not the question.”

“No… I don’t think I could fuck as good as him.”

“Yes, I agree.”

“How does that make you feel?”

“I… a bit lesser than him.”

“A bit inferior to him, I see and why do you think you are inferior?”

Rachel was at this point rubbing one hand on my chest and with the other my caged dick.

“Because… Because he has a bigger dick.”

“Yes, baby, you have a smaller, tiny, little dick. Do you think you would have looked good next to him if you were free? Your exposed little cock?”

“I think I would have looked ridiculous next to him.”

“Yes, yes. A worm next to a snake. That’s why you stay in chastity, right?”

“Yes, that is why I stay in chastity.”

Rachel was biting my ear after every word, could feel her wet pussy around my right leg. My horniness was out of this world, I wished I could stroke, but I couldn’t. My mind was foggy; I could only think about Matias’ soft dick and my girlfriend’s huge, exposed boobs as the feelings overwhelmed me.

“Would you like to see someone like Matias fuck me? Give me the pleasure I deserve.”

“Yes… Yes, mistress.”

“I knew it. Now kneel.”

As I submissively obeyed, she moved to her bag. She took out a big realistic pink dildo, 19 cm, with realistic balls and a suction cup.

“This will give me pleasure tonight and you know why?”

“Because I can’t.”

“Correct answer, loser, now watch.”

She quickly removed her panties. Sat in front of me and opened her legs, exposing her dripping wet pussy. She lowered her back and pushed the dildo, which slid in effortlessly balls deep. She started moaning harder and harder while trusting the dildo with one hand and playing with one nipple with the other. I was kneeling, having the best view, powerless; I knew blood was trying to pump my dick, my right-hand caressing and trying to desperately stroke my member, but it was all pointless. Moan after moan, I was getting more desperate, and she was getting more satisfied.

“Lesson… mmmh… number 2… aah… cucks…AAA… cum last…. now come here and lick my clit”.

With a rapid movement, she got up, dildo still inside, grabbed me and moved on her right, grabbed my head, and positioned right on her pubes, giving me the closest possible view of the sexual act.

“Mmmh…MMMH.. I SAID LICK”

Her scream was nearly out of desperation. I knew she was close to a huge orgasm. I put myself right to work, licking it with the side of my tongue. She was covered in juices, and I could feel the side of the dildo at every trust going up and down, but J didn’t care. I needed to give her the orgasm she deserved. And I did. After less than 30 seconds, she grabbed my head with full force, removed the dildo from her pussy, and screamed. Her legs started trembling hard, and a tiny bit of juice exited her gaped pussy.

“OH MY… GOD.”

She screamed again. Then everything stopped; I could feel her muscles losing force, and she started painting.

“That was… the best orgasm of my life. Thank you so so much, babe.”

I got up and looked at her, smiling. She had the face of someone who had just seen the stars.

“You are very welcome. I am so happy you liked it.”

“Please take the keys here. You must be exploding. The only thing is… that… you know, I am a bit indisposed at the moment.”

“No worries, babe, I can see that; I will knock one off in the bathroom.”

“No, please do it here, in front of me.”

“Oh… alright.”

“Yeah, get back on your sit, in front of my split open pussy.”

“Yes, mistress.”

I obeyed immediately, too horny to process any thought. I kneeled, dick in my hand, ready to explode.

“Don’t stroke yet.”

“Yes, mistress.”

“You see how open my pussy is?”

“Yes, mistress.”

“You see how satisfied I am?”

“Yes, mistress.”

“Is your dick that did this?”

“No, mistress.”

My dick was leaking and begging for attention. I was truly desperate, ready to do anything just to touch it.

“Could your dick ever do this?”

“No, mistress.”

“Exactly, and that is very important for you to understand. Because rule number 3 is that a cuck can cum when, and only when, his girl is satisfied like this. Is that understood, Jack?”

“Yes, mistress.”

“Good, that is the end of our activity of the day. Please do your thing.”

I didn’t need to hear it twice. Exactly three pumps were enough for me to explode on the floor while having the most intense orgasm of my existence. I groaned loudly before collapsing myself loudly on the side, finally with my balls emptied.

 

To Be Continued…

 

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