Sizequeen Resort Pt. 01

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. At 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 at disappointed at my naked body.

"You see, I am glad you are enjoying this, but it clearly shows why this is absolutely 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, 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 had 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, soon you will learn how to behave. Now take the ice at the cage. If it is okay for you in the meantime, 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 own 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 from the website comes with multiple beaches, a restaurant, cocktail bar, spa, two pools and a gym. Special activities are offered daily by our staff, and you can ask for food and drinks from everywhere in 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 to 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 took a pause hearing the click of my now secured device.

"Even though I don't think I will need to remind this to you. 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 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, 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 few 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 her moaning harder and harder.

One, two, three orgasm 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 on 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 laid down next to the love of my life and we started cuddling in the mist of the 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 sighted. 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 ahah."

"And did you like what you found out."

"Mmmmh a little bit."

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

"I still can't believe this was big fantasy from the get-go! Are you sure you are okay with this? You know with me and other men..."

"Yes babe, I really want to test it out. Together. Come on is 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 laying 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 to her and I was amazed by her beauty, she was wearing a gold bikini, same colour of her jewels that truly accentuated her curves. On top a semi-transparent beach robe was completing 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 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 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 for this first week I am out of access. The organisation stressed 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 waters please"

Rachel ordered carelessly from a guy that 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, to 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 by 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 it is that you would like me having sex with someone else?"

"I don't know actually, it's a deep desire I have had in me 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 to Rachel, our meal being 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 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 to find other people, so I opted for some deck chair 10 meters from where we were staying. We both got covered in sunscreen, always available in any corner, and placed ourselves comfortable, her facing the sun and me lying face down trying to hide my exposed caged.

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 a conversation was some new people.

"Oh, so sorry we waked 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 Cleary south American, big arms a bit of a 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, curly black hair, beautiful puffy lips, perfect C cup breast that she was showing proudly topless, 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?"

"Juliaaa, 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 legit question. It will be on display for the next days, so it is better to avoid any kind of rumours 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 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 ahaha."

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

"Thank you! it is the first time someone tells 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.

"Juliaaa, not now please. You truly don't know how to behave"?

"I am sorry cutieee, it's this island, we are having so much sex and it is always soo 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 mins ago, give me a rest."

"Alright, alright. and Rachel 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 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 beautiful boobs.

"Oh wow, are they natural?"

This time was Matis 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 ahhahaha"?

"Heyyy, 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 and 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 in 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".