Sizequeen Resort Pt. 02

This is the second part of an ongoing story, it will not make much sense if you don't read the first one.

I really appreciated both the positive and negative feedback on the first part and I tried to improve based on it. Feel free to leave more down here: I read everything :)

The story is contains heavy cuckolding, humiliation, chastity and sph. It will also contain feminization and forced bi in the future. Be advised.

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Chapter 4

We spent the rest of the night cuddling and talking. So much kinky activity required some time together to make up for it. Neither of us had any intention to risk ending up in the middle of an organisation, so we ordered food in the room and talked about our feelings. We were both enjoying it quite a lot. The new-found dominant side of my partner was unexpected but very welcome. We both had just had the best orgasms of our lives, and we were excited to see what else the programme had in store for us, as I found out this was the only activity she had received specific instructions for. We found ourselves laughing and joking for hours before setting up a movie on TV and falling asleep while hugging.

The following day, I woke up at around 8 and was incredibly refreshed. We decided to get breakfast in bed and plan the day. I knew that today Jacob would have arrived and the real programme would have begun, so I tried my best to stay in the room as much as possible to get some normal time with my love. She seemed a little nervous as well. I knew that they had already chatted before, but she kept avoiding any kind of question about the extent of these conversations by saying that they just followed the guidelines provided by the website and just made sure to be compatible before meeting in real life. This thing was making me super jealous, but Rachel was very good at reassuring me that it was all about sexual chemistry and nothing and nobody could have ever replaced me as his partner. Jacob's shadow followed me around all morning, despite my best attempts not to think about it.

We kept the same strategy as the day before, and we tried to avoid all the other people in the resort. The plan succeeded quite well for the morning. Rachel dressed up in another bikini, red this time, very similar to the first one. I, on the other hand, decided to try something else to make my chastity device less visible: the crotchless swimming trucks, this time paired with a long t-shirt that could have partially covered my exposed parts.

We went for a swim and enjoyed some sun in the same spot as the day before. We briefly met another couple, Jim, a 45-year-old businessman with a dad bod and, of course, a huge dick, and Sakura, a 20-year-old petite Japanese girl. Luckily, after learning about our current situation, they were not too interested in chit-chatting and left us to our morning. The meeting was surely less traumatic than the one the previous day. The experience with Matis gave me the strength to not pay too much attention to the questions or comments.

After that, we decided to head for lunch, but I noticed that Rachel was becoming more nervous. No question needed to be asked; I knew why.

We took a seat once again at the extreme corner of the restaurant. We could hear some unkown voices from the other side of the place, and we tried to lay low to avoid any attention.

When Rachel touched the button for ordering the food, the waiter informed us that, unfortunately, we would have to wait 10 minutes before getting it as someone would have joined our table.

My heart sank, and a mixture of fear and excitement grew in my body. I did not expect it to be so sudden. Rachel had the same reaction, and I saw her starting to touch her hair.

"Oh my, I just went swimming. Do you think I look hot, hubby?"

The question left me speechless. What was I supposed to say? That you are beautiful for another man?

I replied in a semiautomatic voice, too much used by years of relationship.

"Of course you look hot, honey!"

"Aaah, my face, it's all over the place; I should have put the waterproof make-up on better."

"I too think you are beautiful."

From the same corner, the waiter had just disappeared, and the man who later completely changed my life appeared.

He was as described and more. He was tall, at least 1.90, with military-cut black hair, a strong jaw, and bright smiles. He was built like an athlete, nearly ripping out of the half-open white Lyne shirt, which was the only thing that he was wearing apart from his sunglasses. Between his bulky legs, an anaconda was wiggling at every step, probably the same measure as my fully hard cock. Moreover, something above everything else stood out, as Rachel had failed to mention it. The guy in front of me was black, which gave an interracial spin to my expectations that was truly unforseen.

"Jacob!! I am so happy to finally see you in person!"

Rachel got up from the chair with the excitement of a high schooler seeing her crush and ran towards him. She almost jumped on him, trying to put her arms around his neck. He grabbed her from the lower back, and the two exchanged what could have been seen as a hug between long-time friends if it weren't for Jacob's naked monster rubbing against her leg.

I stayed seated, not willing to face my member to his, and actually sneakily tried to lower my t-shirt, hiding it better.

"And you must be, Jack. I am very pleased to meet you. Rachel told me so much about you that I couldn't wait to finally meet the man behind this wonderful woman."

"The pleasure is mine, Jacob. I was delighted to meet you. She told me a lot about you as well."

"Oh, I hope not too much!"

Rachel and Jacob shared a complicit look and chuckled.

"Allow me to sit here; I would love to get to know everything about you guys."

We were seated around the table, and he started asking all sorts of questions about us. How we met, what we did, and our lives in general. Despite the fact that I was sure he already knew all the answers, I happily answered all of his doubts. Jacob revealed himself to be a very charismatic, humble, and funny guy, genuinely interested in the conversation and always finding the occasion to make a very respectful joke. We ate together, and for a solid hour, I forgot who he was and why he was there.

"So, Jack, Rachel, I am having a lot of fun with you, but I think it is time for me to start to introduce you to the programme you signed up for. Is it okay?"

"Yes."

"Alright."

"So let's start with the fact that I am a guest like you two; I am not getting paid by the resort. I, like Rachel, received some preparatory training on what to offer you in the coming 7 days. Luckily for you, having nearly 15 years of experience as a bull put me in the position of being able to offer you more, in terms of knowledge and understanding, than your average instructor. In the next week, I will teach you, Rachel, what it really means to be a hotwife and all the benefits that this lifestyle can offer, and I will teach you, Jack, the bliss of being a cuck and how this can have huge benefits for people like you. We will have daily activities together that will teach us more and more about the roles and responsibilities as well as the pleasures brought by a true cuckold relationship. After the week is over, you will both have a day completely to yourselves to discuss what you have learned and what you want. The following two weeks will depend on your desires during those 24 hours. I will often be very dominating, as per my nature, but we will set up together a safe word to be used at any time to stop any kind of action. Everything clear so far?"

"Clear."

"Clear."

"Great, so let's keep knowing each other, but this time let's talk about cuckolding. Rachel, why do you think Jack has an interest in this practice?"

"He told me yesterday because he wishes to see me receiving pleasure."

"Good start, but I think there is more. Wanna add something, Jack?"

"Well, I think that's it, actually."

"If it were only that, toys should be enough, wouldn't they? You brought her to a place called "Sizequeen Resort."Do you like the fact that someone with a dick bigger than you brings pleasure to your girl, don't you?"

"Mmmh, I don't know... maybe."

"It's okay if you cannot admit it in front of me; you are at the beginning of your journey anyway. You see, this desire that you have is absolutely natural. At its core, the cuckolding lifestyle is very simple. A man is not able to satisfy the needs of his woman, which creates problems both in the sexual and emotional spheres of the relationship, so he looks for another man who can do so. The woman, of course, accepts that it is only natural to have your sexual needs satisfied, but she keeps the man close for the emotional bonding, which is way more important than the sexual one. In this kind of relationship, the two needs of the woman are split between her man, to which she grows closer as she solely focuses on the emotional side, and the bull, which can always be the same or changing. Now, Rachel, forget about the bull; where do you think the problem is in this kind of relationship if approached carelessly?"

"The woman is completely satisfied, but the man is not sexually satisfied."

"Exactly! This is very dangerous, and it is the number one cause of the failure of the cuckolding relationship. This introduction is specifically designed to teach you how to fix that. It will be my main duty, Jack, to teach you how to get pleasure from giving pleasure, for every cuck is a little different, but all of them, once they find the right balance, see incredible benefits from all sides of their lives. By trusting me, I promise to make you reach a new level of happiness. Do you trust me?"

"I mean, everything that you said actually makes sense. You surely know what you are talking about. Only one question: How do you keep your emotional life balanced?"

"Me? Oh, I got married young, at 18, with the love of my life, Alicia. She is absolutely supportive of what I do. We ourselves have an open relationship. The key is completely separating love from lust."

"I see, I see."

"One thing is understanding, and one thing is assorbing this concept. If you could lead me to your bungalow, I think we can start with your first activity."

He got up, and Rachel followed suit, visibly excited. I reluctantly stood up, fearful of Jacob's reaction to my caged member, but to my surprise, he paid no attention to it and started chitchatting nonchalantly with my girl, who was leading the way.

I was immediately left behind, and I walked behind them for the entirety of the very short, but humiliating, walk home.

"Now, please, Jack, get naked and remove your chastity device."

I removed my shirt as Rachel removed the lock Once out, my cock got immediately pathetically erected. We were now both standing in the middle of our room, completely naked. It was now apparent that his size soft was nearly the same as mine hard.

"The first exercise is about acceptance. The main reason why the cuck subconsciously suffers is because he cannot accept his role in the couple, despite the incredible benefits that would come from it. The process of acceptance is long and requires constant training. Today, I would like to give you a taste of it and how, even for that, pleasure could come. Jack, why do you think your dick is hard right now?"

"I...I...I..."

"Because you want to compete with me. You get hard, ready to show your girl who fucks better. This process is, I am afraid, absolutely delusional. Rachel, please sit on the bed, and Jack, please face her with me. Without considering any experience in bed, by pure gut sense, which cock do you think could provide you more pleasure? Please point at it."

I looked at Rachel; she was sitting on the bed with her legs crossed, but it was clear that she was incredibly wet. Ever since Jacob showed up, she had kept checking out his dick; even on the island of big cocks, he had the biggest one. She looked at me in the eyes, and I smiled back. Everybody could have known the answer; there was no point in lying.

She slowly raised the finger. The answer was predictable. Ouch.

"And why is that?"

"Because it is bigger..."

"Now, after considering everything else, consider what I have told you about myself and what you know about your husband. Who do you think would fuck you better?"

Once again, the finger was laid on Jacob.

"What do you think, Jack? Do you also think I could fuck your woman better than you?"

A wave of excitement went through my body; my cock was now rock hard and leaking. My mind was becoming foggy from the horniness.

"Y-yes Jacob."

"I also think that. Do you feel the pleasure building inside you? I see you are loving it. This is the sexual pleasure you will learn to ride--the pleasure of knowing your place. Now that you are clearly receiving pleasure, don't you think we should do the same?"

I gulped. I looked at Rachel, and I saw how needy she was. Her pussyc was soaking wet, and her eyes were begging me for it. I understood, for the first time, what he meant.

"Yes, you are right."

"Now comes the more personal part of the lifestyle. Rachel, come here, please."

"Yes daddy."

She replied immediately, almost running on her knees in front of him.

"Jack, do you want your wife to receive pleasure?"

"Yes Jacob."

"Do you want me to give it to her?"

I looked at Rachel; her eyes were fixated on his cock, now centimetres away from her face, still soft. She was almost salivating. How could I even dream of denying this to her?

"Yes Jacob."

"Please call me teacher from now on, as from this moment on, you both truly accept me in this role. You can start."

Without waiting a second, Rachel started licking the cock vigorously. She stroked it slowly with one hand as I saw it grow with my own eyes. The view was out of my wildest dreams, and the love of my life was sucking a BBC right in front of my eyes. The cock kept growing and growing; it was already 18 cm when she started sucking his balls while stroking the shaft with both hands. Our teacher was watching, amused, and keeping eye contact with her.

Soon it reached its full size, a monstruos of 22 cm, and at this point, Rachel abandoned his balls and allowed him to lay the entirety of the shaft on her face.

"Look, babe, how big it is."

"You know it has another couple of cm to spare."

He cut me off. Hearing that information, she started sucking passionately on the head. The cock was long but slim enough for her to take the full size. I knew my girl; she loved challenges, and for this reason, it was almost natural for me to see her trying to take all of it. She kept sucking at an increasing pace, one hand stroking the bottom of the shaft while the other was massaging his balls. Every time she tried to go a little deeper, but soon after half way, she started gagging. She had already found her limits. Seeing this spectacle straight out of a porn movie, I slowly started jerking off. After only two slow strokes, I realised that I had to be careful; my dick was so sensitive that I could have cummed in a matter of seconds.

"Get on your fours, bitch."

She immediately obeyed, jumped on the lower end of the bed, moved her bikini, and revealed her dripping wet pussy. Honestly, I had never seen her so wet before. Jacob got closer and started rubbing the head of his cock against what used to be only mine. That was too much. I started jerking my cock. One pump was enough to send me over the edge. I groaned in pleasure as a wave of new pleasure filled my body. My orgasm was long and intense; it seemed infinite, but the post-nut clarity hit hard.

In front of me, the love of my life was moaning in pleasure as a stranger had just inserted the head of his huge dick inside her.

"I... am starting to have second thoughts."

"mmmmh...Why?"

Now Jacob had stopped and was looking straight at me without saying a word. Rachel, on the other hand, had her face on the pillow and was slowly grinding on his cock.

"I just..."

"Mmmh, babe, what are you talking about?"

She was going deeper and deeper.

"I don't know if..."

"Ba..be..mmh..aaah..don't be silly now..aaaah."

The safe word--fuck, we never decided on a safe word. I looked at Jacob; a huge smile was covering his face. He was clearly enjoying every second of this.

The sense of humiliation and excitement started flowing back.

"I... uh... nevermind, sorry."

Rachel was now past halfway on his dick, her moaning getting louder and louder, her pussy juices already wetting the bed.

"Should I fuck your woman?"

...

"Should I give Rachel the dick she deserves?"

"...Yes teacher."

"That's more about it, cuck."

As the words exited his mouth, he very slowly started trusting inside the love of my life, his dick. Her moans were getting louder and louder. My dick was already stiff and asking for a second round.

After no more than 10 seconds of low trust, the moans became screams. After another 10 and a couple of cm of dick more, she had already cum.

Jacob looked at me and showed me one finger.

"OH MY... SO GOOD"

Jacob started moving again.

"Aaah...AAH... aaah"

He was now three-quarters in.

"Now watch. And you better not touch your pathetic excuse of a dick before I am done."

The scene that followed was wild. He started fucking her with increasing intensity. Slapping her beautiful ass every couple of thrusts. She was having an ethereal experience; she couldn't stop moaning, and every couple of minutes she was having an orgasm. I was standing to the side, powerless, watching a spectacle out of this world, my dick as hard as a rock. He must have known that she could not take so much of that intense sex, because after just a couple of minutes, he gave her two full-length pumps, almost giving her the full size, and exited her pussy, leaving her with a gaping hole, shacky legs, and a mess on the bed.

He then looked at me.

"She has already cummed six times; take this as a test drive and consider lesson one over. I hope it was good enough for you to understand your role. Tomorrow we will explore together how a cuck can find pleasure in the sexual act as well as the basics of well-manners in a three-way relationship. The way you behaved today was absolutely out of line, but no worries; it was to be expected, and tomorrow we will start fixing that. See you for breakfast!"

And without saying another word, he grabbed his stuff and, with a bright smile, exited the room.

Rachel slept peacefully for the rest of the afternoon, leaving me alone with my thoughts. I couldn't stop thinking about what had just happened. The scene was so erotic; her face and the voice of absolute pleasure that she made when I asked to stop were images that couldn't leave my head. I spent the following hours reviving the scenes again and again in my head. My cock was rock hard, but I didn't jerk off. Deep down, I wanted to reclaim her for myself.

She woke up nearly at 6, still tired from the rollercoaster of emotions.

"Mmmh...Oh baby, I am so sorry I fell asleep."

She said, yawning.

"Don't worry, I saw how tired you were."

"Did Jacob go away?"

"Over 3 hours ago."

"Oh wow, I slept a lot."

"You fell asleep right as he was over."

"...Oh right."

Her face turned red as the realisation of what had happened hit her. At the same time, I could see from how she was moving her legs that she was starting to get horny again.

"Should we talk about this?"

"Yep, it was intense."

She got seated and looked at me with sleepy eyes. When she saw me leaking, her face woke up immediately.

"Oh my... you didn't cum, didn't you?"