Sizequeen Resort 2

By arandom.

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 organization, 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 program 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 eight 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 program 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. Still, 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 unknown 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!”

“Aaahhh, my face, it’s all over the place; I should have put on the waterproof makeup 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 a bright smile. 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 unforeseen.

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

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, 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 meet the man behind this wonderful woman finally.”

“It was a pleasure meeting you, Jacob. I was delighted to hear that she also told me a lot about you.”

“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 and 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 program you signed up for. Is it okay?”



“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 seven 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?”



“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?”

“Mmm, 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 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 you said actually makes sense. You surely know what you are talking about. I have 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 have an open relationship. The key is completely separating love from lust.”

“I see, I see.”

“One thing is understanding, and one thing is absorbing 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 soft size 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?”


“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 pussy 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 centimeters away from her face, still soft. She was almost drooling. 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 monstrous 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 halfway, 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 realized that I had to be careful; my dick was so sensitive that I could have cum 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.”


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…”

“Mmm, babe, what are you talking about?”

She was going deeper and deeper.

“I don’t know if…”

“Babe… Aaahhh… Don’t be silly now… Aaahhh.”

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… never mind, 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 ten and a couple of cm of dick more, she had already cum.

Jacob looked at me and showed me one finger.


Jacob started moving again.

“Aaahhh…AAH… Aaahhh”

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 cum 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-mannered 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.

“Mmm…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 realization 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?”

“I was waiting for you.”

Her face relaxed, and a condensed but sweet smile filled it.

“Come here and kiss me.”

I didn’t need to hear it twice; I crawled on the bed and started kissing her passionately. We embraced in a hug, and we started rubbing our bodies. I was hard as a rock, but I could feel that she was wet herself. I couldn’t wait much; I got on top of her and went straight for the pussy. My cock entered immediately, both for the copious amount of lubricant and because it was still stretched from the morning.

It was a weird sensation; my cock couldn’t fill her from all sides as usual, but I had to choose one.

Without stopping to kiss her, I grabbed her amazing ass and started fucking her in a missionary position.

After no more than 20 seconds, it was already over. With a loud sigh, I exploded inside her in a liberating orgasm.

I fell to the side, panting, as she started caressing my hair. After a couple of minutes of silence, she got up and went to the bathroom to clean herself up.

“You are officially a cuck, love; how are you feeling?”

“I feel… satisfied, actually. And you?”

“Oh, I feel satisfied as well, ahhh.”

“Did you like the sex with Jacob?”

“Well, we can say that.”

“It was mind-blowing, wasn’t it?”

“The best sex of my life easily; I don’t know how many times I cum, and each one was more intense than the previous one.”

“You know that he didn’t even finish?”

“For real?”

“He said you weren’t ready yet and to consider this as a first taste.”

“Oh my, he had more? We must have gone at it for almost an hour.”

“Actually, no more than 10 minutes.”

“You serious? Damn…”

“And what do you feel about me after this? Do you think you feel farther away from me?”

“Actually, quite the opposite. I am so happy I am here with you now, decompressing. I now know more than ever that you are my safe space. And you? Do you see me as a slut?”

She came back to the bed, slipped below my right arm, and hugged me tight.

“Why would I ever think that? I asked for it! And you were so beautiful during the act–a pornstar’s almost.”

“Ahaa, your pornstar’s.”

“Yes, my pornstar’s. I feel closer to you than ever. There is nothing I feel I could ever hide from you at this point.”

“Same for me.”

We spent the rest of the evening cuddling in bed, decompressing, and watching TV. This experience had actually brought us closer on an emotional level, even though we were not yet comfortable enough to talk extensively about dirty sex. We were to talk about how it made us feel. Like the day before, we had an amazing time together and fell asleep only late at night.


Chapter 5

The following day, we both got woken up early by a knock on the door and a familiar voice outside.

“Wake up, lovebirds. I will wait for you at the bar for some breakfast and to plan the day ahead.”

We both got up, grunting, and got prepared for the day. I dressed as the previous day, as the clothes were almost untouched, while Rachel put on an incredible green one-piece swimming suit that covered as much as a thong on the ass while being small enough in the front to show some serious sideboobs.

After putting on her chocker and bracelet and securing my cock in his cage, she kissed me and opened the door, ready to go out.

We ventured to our usual spot, where Jacob was waiting for us with the table already filled with food. He was dressed in nice kaki shirts and the same old sunglasses. He lay comfortably on the recliner, legs spread open, showing the world his pride, which was lying comfortably on the seat.

A few meters from us, I identified Dan and his partner sitting at another table with two unseen couples. From my angle, I could only see one platinum blonde girl, extremely thin, who looked like she could have been from Russia with blatantly fake boobs, and one guy in his late 20s with curly hair and a great pair of mustaches. I was trying to get a look at the other couple, but Jacob brought attention back to our table.

“Slept well?”

“Like a baby.”

Rachel promptly replied.

“Great, I was sure I had left you well relaxed.”

Rachel chuckled, embarrassed, and sat down. I followed suit. While eating my eggs, I tried to talk about something different from our past afternoon.

“What did you do after you left?”

“I went to meet the other couple, took part in some group sex, and got drunk in front of a bonfire. I had a great evening, actually. Did you stay in the room?”

“Yes, we had to decompress.”

“Understandable. I guess you had time to talk about what happened.”


“Any feedback?”

We looked at each other, and Rachele replied.

“Only positive feedback.”

“Great! Ready for today’s activities?”

“Looking forward to it!”

Rachel was truly excited, and I was a bit worried about what that man was capable of.

“Great, so this morning, you will have your first introduction to etiquette. Let’s start with the basics. In any cuckold relationship, regardless of whether there is only one bull or many, it is always important to remember that it is the couple, most specifically the cuck, that is the first one to require some assistance. Hence, they are the ones who have something to give back in the relationship. Do you see yourself in that?”

“Yeah, actually, it was Jack who tried to introduce me to this in the first place and looked for the resort.”

“You are the perfect example, then. So it is very important for you, Jack, to show some recognition for what I am doing, as I don’t need to be here. I have plenty of girls with whom I could have a good time right here right now. Does it make sense to you, Jack?”

“Yeah, it does make sense to me.”

I was starting to get horny again. The humiliation of having to be thankful to a guy for fucking my wife was driving me insane. I also saw that Rachel was starting to get worked up. Probably, the dominance that was happening in front of her was turning her on.

“Happy we can agree on that. So now, a couple of general rules for you, Jack, to follow that can apply to all bulls:

Please refer to all bulls with the title they prefer; use sir when you meet them for the first time. I asked both of you to use teacher before, but you can both use sir and master as an alternative. Rachel, I would love it if you said Daddy.”

“Yes, daddy, I like that.”

Rachel replied, chuckling, clearly enjoying the conversation.

“Is it ok for you, Jack?”

“Yes, sir…”

“Great. Most bulls like to call the cuck by different titles, the most common being cuck, cucky, and hubby. It is safe to say that if this happens, the cuck needs to accept it. Clear cuck?”

“Yes, sir.”

I responded submissively. I looked to the right, and I noticed how this display of power was working Rachel more and more. From my seat, I could see that her swimsuit was starting to get soaked.

“Good cucky. The second basic rule is: as we said, the bull is here for you; make sure you treat him like your best guest. Rachel always stays smooth and ready for him. Dress hot. Cuck, help her do so. Try the kinkiest lingerie and buy some provocative dresses. If you can afford it, pay him dinner or call him an Uber home. Make sure he wants to come again.”

“You hear that, Hubby, we should go do some shopping together! I heard they have a very spicy shop here!”

“Alright, alright, always looking for an excuse, don’t you?”

“Third basic rule: when all three of them are hanging out, it is good that the cuck does not disturb if the hotwife and the bull are flirting. You asked for this to happen; you are the one enjoying it the most. Please don’t make it all about yourself. I, for example, truly enjoyed chatting with both of you today, but if we started getting worked up, I wouldn’t want you to ruin the vibe.”

“Yeah, that makes sense. I will try to respect this rule the best I can.”

Rachel started biting her lips and opened her legs. Despite being in public, she could have jumped on Jacob on the spot. He was noticing it and avoiding her eye contact, focusing on me and humiliating me with every word.

“To finish some personal rules that I like my couples to follow, There are actually many that I will tell you when the time comes, but two are very important for me. The first one is that when in public, I like that the cuck introduces me to any new friend as “the person who fucks my wife.” Is it okay for you, cuck?”

I looked at him with my eyes wide open. He wanted what from me? to expose and humiliate myself in such a way just for his pleasure?

“Come on, hubby, everyone will know anyway! Is it so hard for you to show some basic recognition? We just talked about it!”

I turned my head to Rachel, and I saw her smiling at me. She was serious. Her swimsuit was soaking wet. She was into this 100%.

“You are right… Okay, sir, if you want, I can do this for you.”

“I knew you were a great couple from the get-go. Now the second one, which, in this case, I think would also be greatly beneficial for the scope of the program. I like to be in charge of the key to the chastity device. Would it be okay for you two?”

I looked at Rachel; she would have jumped out of a window if he had asked at this point, considering how horny she was.

Should we really give this guy the key to my dick? She looked me in the eyes and started saying yes with her head, trying to convince me. I looked back at Jacob.

“I am not too sure about this…”

“I know what you think. Why should I give this guy the keys to my cock? The answer is easy. First, it creates a line of trust between us: we can trust that as long as I am around you, you will not need to use your dick. Second, remember what I told you yesterday about you getting hard while we have sex? It is something that goes against your interests. During the program, I will teach you how to get pleasure properly, which is actually a matter of this afternoon. By trusting your key to me, the teaching will be more effective. I have 15 years of experience, for god’s sake. Are you willing to try for just seven days?”

“I mean, if you put it like this…”

“Great choice, cucky.”

Without waiting for confirmation, he gestured to Rachel. She removed the chain where the key was and gave it to Jacob, who put it on his neck with a victorious smile.

“Amazing! With this gesture of trust, we finish the morning class; now, before the afternoon classes, I will require you two to do some homework.”

“Yes, Daddy…”

Rachel’s pussy was soaking wet; she was almost eating him alive.

He got up and scratched his anaconda, which was now exactly in front of our noses. My love’s eyes got stuck on it as he was happily wiggling it in front of her.

“Cuck, it is now time for you to put into practice what I told you this morning. Go to the shop, which is on the other side of the island, and make your woman ready for me. We will meet in front of your bungalow by 6 p.m. If someone asks, proudly say you are doing shopping for the man who fucks your woman. If you do a good job, I will consider letting you out later.”

As he finished talking, he wiggled the key in front of me. He was not playing around. A wave of excitement hit me; my cock responded and tried to get hard once again, finding the cold metal. Rachel was horny as fuck, but the idea of shopping was more powerful than the one of cock; she finally snapped out of the spell of Jacob’s dick and looked at me excitedly.

“Finally, some new clothes!!”

“Yes, baby, take a new swimming suit for tomorrow, as well as something nice for tonight. I have reserved a very romantic spot for the three of us in a secluded space where we can watch the sunset and nobody will disturb us. If you need me, I will spend the rest of the day surfing with some friends in the north of the island. See you later!”

I got up and left for the beach. I turned to Rachel, and of course, she was excited. Was I forced to go shopping for her? Sometimes, dreams come true.

She jumped and took my hand, leading me in the opposite direction Jacob had just gone. She started talking about the kind of dress she wanted, not even aware if it was available or not, while I silently started looking around, pretending to be listening. It was the first time I was actually seeing the island; my fear of being seen had prevented me so far. After two days, I was feeling a bit more comfortable going around like this, but I still tried to lower my t-shirt as much as possible to hide my cage.

We walked in front of a bar and a swimming pool, where two people were very obviously having sex under the surface of the water. We passed in front of a sunbathing area where we saw pretty clearly Dan having sex with a Brunette MILF with some huge boobs, and finally, we reached our destination and the furthest part of the island.

The shop was a small white building with big windows displaying all kinds of erotic toys and skimpy clothes, situated right next to what I assumed was the tattoo shop.

Inside, we found only a clerk and a girl browsing. She was quite petite, 1.60 max, brunette, brown-perceiving eyes, and a perky C-cup breast that was held high by a micro bikini. Overall, her figure reminded me of a gymnast, with surely fewer muscles and incredibly big boobs for her size.

She looked at us and smiled.

“Ooh, I haven’t seen you yet. It’s very nice to meet you! My name is Lucy. Are you looking for some spicy clothes for the party tonight?”

“Hello! My name is Rachel! Actually, we had no idea there was a party; we are here because…”

She touched me and looked into my eyes, reminding me about our assignment.

“Very nice to meet you, Lucy. I am Jack, and we are here because… I am buying the love of my life some nice clothes for the man who is going to fuck her tonight.”

“Oooooh, you are the cuckold couple, my bad. I should have noticed that!”

She replied, chuckling and pointing at my caged dick.

“No worries! Actually, I really like the dress you are looking at; I think it is very brave.”

The clothes around her immediately absorbed Rachel.

Lucy was looking at an incredibly kinky piece of clothing. Red, very short overall, and visibly very tight. The chest area was fully open, leaving the breasts of the person wearing it completely exposed.

“True! This is the only place you can freely wear stuff like this. It would be a shame not to take advantage of it! Were you looking for something similar?”

“I don’t know… What do you think, hubby? Do you think I should be daring? I bet you would love it if I pulled off an outfit like that with you.”

“Yep, not going to lie. I would go crazy if you showed up with something like that on a date. I’m not very sure I would love everyone looking at your exposed breasts.”

“I am sure Daddy won’t mind.”

Rachel quickly replied, burying me in shame. She then looked at me and added:

“I am so happy you can help me choose the dress for tonight! Just help me understand what you would like, and I will add a kinky spin to it.”

“Well, I don’t know if I want to do that.”

“Come on, hubby! We just talked about this! You have to learn to be thankful. Daddy just asked for a little favor from you. Is it really so hard? He is doing a lot for us; you know that.”

“You are right; you are right.”

In all of this, Lucy was giving the back and browsing the clothes, pretending not to be listening but clearly amused. She decided to jump back into the conversation.

“How slutty are you willing to go, Rachel? There are so many options here!”

“Mmm, I am not sure.”

“How bad do you want his dick?”

Rachel got slightly red at the question but replied shamelessly.

“Oh, I want it really bad.”

“So you need to go the extra mile, sweety! No worries, I can help you with that, and your cuck is going to be the perfect judge for this! He can sit outside, and from his reaction, we will be able to see what will really hit the mark.”

She made me a gesture with her hand, and Rachel nodded, smiling. It was useless to complain, so I exited the small shop and sat on a chair right next to the entrance, waiting for them to call me back.

I could hear them giggling, but it was not very clear what they were talking about. I looked at the ocean, and I tried to calm down.

The idea that I was supposed to help Rachel get all fancy for Jacob was driving me crazy, but at the same time, I knew I was horny, and I was feeling my penis pressing against the cage. Weirdly, I was feeling pleasure; maybe that’s what he was talking about.

After almost an hour, Rachel finally showed up. I looked at her, and I was left breathless. She was gorgeous; she was wearing a very short black dress with a deep v-cut on the front that allowed a mind-blowing view of her huge chest.

She sat in front of me and looked at me.


“You look great, mistress…”

“I told you it’s not daring enough; look at his face; we can surely do better.”

Lucy came out of the door and cut me off.

“You are right; he likes him, but I want him drooling. Be right back, cucky!”

They disappeared again for countless minutes.

The second time, Lucy came out first, triumphant, and with a theatrical gesture of her hands, she introduced Rachel, who came out like a model.

This time she was wearing some very short ass shorts that were leaving half of her ass out, on top of a black semi-transparent blouse that was clearly showing a black micro-bra that was covering nothing but her nipples.

I could not stop looking at her incredible breasts, and I could feel new blood trying to flow to my cock. Rachel was waiting for a comment, and I was too distracted to notice that. Once again, Silvia broke the silence.

“I told you the semi-transparent was the way! Look how dumb he is looking! If you try the one I showed you before, you are doing a jackpot.”

“You were right!”

Rachel giggled, pressing her boobs and sending me a flying kiss.

“Stay still, cucky; I am sure you will love the next one.”

And they were right. After 15 more minutes, they got out again, and Rachel was wearing the kinkiest and daring dress I had ever seen her put on.

She was wearing a very tight black bodysuit, as short as the pants she had worn before. Like the shirt before, it was very transparent and showed everything below. The only parts of her clothing that covered something were a very thin black G-string and a micro bra.

I felt immediate pain in my crotch area as lust filled my body. Never before did I want to jump on my woman so badly.

They both looked at me and smiled in satisfaction.

“This is the face we want, Rachel!”

“You are absolutely right; now I see it. I am just not sure if it will have the same impact on Daniel. You know his standards are way higher.”

She made a spin, showing off her beauty, and then addressed me.

“Why are you not talking, cucky? Tell me, do you think Daddy will like it?”

“I… I… You look absolutely gorgeous; I don’t think anybody would be able to resist you like this.”

She took a step forward and got closer to me. Everything from her body posture screamed confidence. I couldn’t stop looking at her tits.

“You are so sweet, hubby! But this is not what I asked for. Let me rephrase: do you think that Jacob will want to fuck me if I show up like this? I see you trying to get erected in your cage; do you think it will have the same effect on his huge cock?”

I looked at her, the lust growing in me now making my mind foggy.

“I am sure he will love it, mistress. But if you want to be sure, you could go braless.”

Lucy erupted in a laugh from the back.

“Look at this guy! You are so lucky to have such a good cuck; that’s actually a great idea! What do you think, Rachel?”

“I think you are being a very good boyfriend! I will surely follow your suggestion later.

Now come in; you got to pay for this and the swimming suit I chose!”

She grabbed my hand and brought me back into the shop. The cashier grabbed her clothing and folded it in the bag where the other two packages were waiting. After asking what it was about, Lucy was kind enough to inform me that they had also chosen an outfit for me, and Rachel really wanted it to be a surprise.

I didn’t ask too many questions. I swiped my card, grabbed the bag, and waited outside with Rachel while Lucy was paying for her stuff.

I could see how excited Rachel was, and weirdly, I was happy for her. She was smiling and chuckling at every word, something I hadn’t seen in years.

We decided to grab something to eat with our new friend. Lunch was quite uneventful; the two girls really clicked together and chatted ominously for a couple of hours about fashion, gossip, and boys—all the things I am not fit to discuss. I took the occasion to have a swim and rest on a recliner, trying to get a tan, feeling happier than Rachel had found a new pal.

At around 4, I was woken up; Lucy had already left, and Rachel told me that I had to come with her as we had to start preparing.


Chapter 6

As Rachel was having a shower, I found myself in the awkward situation of having nothing to do while waiting for her. To make matters worse, I was caged with no way out of it. I turned on the TV, trying to cool down and distract myself, but for the first time, I was feeling a sense of frustration building up. I could not lie to myself; the whole adventure at the shop was extremely erotic, and regardless of how hard I was trying, images of both Rachel and Lucy’s bodies kept filling my mind.

Finally, Rachel finished washing, and we swapped with her staying in the bedroom and getting her make-up.

As I entered, a shower of excitement hit me. Automatically, I tried to jerk off but only found the hard metal cage. I tried again and again to stroke, but nothing. It was impossible to get even the slightest pleasure from it. After 10 minutes of pure frustration, I gave up, and after another 5 minutes of cooling down, I exited the room.

Outside, I found Rachel fully naked, applying make-up on the mirror next to her bed. Grunting, I lay over in the bed next to her and tried to distract myself with some TV. Again, regardless of how hard I was trying, her figure was too distracting, and my mind was getting foggy from the lust. I began massaging my caged dick, trying in any way to feel something. After a couple of minutes, she broke the silence.

“Too horny?”


“Sorry for this, but there is nothing I can do.”

“I know, I know, it’s just a new feeling I have to get adjusted to.”

“You know, I have never seen you with such sexual energy.”

“I can say the same to you.”

“You have no idea how wet I am.”

It was true; I could see she was actually dripping.

“Can I lick it?”


“You heard me right.”

“Are you sure? Isn’t it going to hurt you?”

“Maybe, but I am going crazy here doing nothing.”

“Well, if you put it like that… but I need to finish applying my makeup. You have to come here.”

I looked at her and nodded. I got up and kneeled in front of her. She opened her legs and exposed her fully leaking pussy to me. I started licking immediately.

The feeling was weird; from one side, the burning humiliation of the situation mixed with the lust accumulated in my body. On the other hand, I fully committed to my task, trying my best to satisfy my woman. She immediately started moaning and cum within a couple of minutes. From then on, I kept eating her out softly, allowing her to be focused on her task. I went on for at least 20 minutes, silence filling the room, interrupted by an occasional moan. I was in a cathartic state of constant pleasure mixed with frustration.

Suddenly, she announced she was over, grabbed my head, and ordered it to go faster. Naturally, I obeyed and drove her to a second orgasm before being told that I had to help her with something else.

I stayed on my knees as she gave me both her panties and her body suit.

I slowly helped her get into the G-string as the scent of sex filled my nostrils. I followed immediately with the body suit before helping her put on the shoes, a very fancy-looking pair of sandals she had brought from home.

Finally, I got up and observed her in all her beauty, which was truly breathtaking. She smiled at me, and I smiled at her. Her completely visible boobs would have been a good reason to complain on any other occasion, but I was too horny to say anything. I couldn’t complain; my mind was solely focusing on earning my key back, and to do that, I knew I had to earn it from Jacob.

Now, it was my turn. The clothes that Rachel had bought for me were nothing too crazy. A simple Lyne white shirt and a pair of jock straps open in the front as well as in the back. The increased exposure of my ass was something I felt like complaining about, considering both my situation and the fact that everybody was naked around me.

As soon as I finished preparing, Jacob knocked at our door, and I went to open it.

“Oh my, you look absolutely gorgeous.”

He looked at her, completely ignoring me.

“You like it?”

Rachel giggled and gave him a spin.

“Cucky really helped this time around.”

Jacob looked at me, smirking, and gave me a nice pat on the back.

“Nice job, man; I am very impressed. I didn’t know you had such a fashion instinct.”

“Oh… no worries. I just did as you asked.”

“And you did amazingly!”

As he was saying this, Rachel got next to him and hugged him from the side.

While both of us wasted the day trying to get fancy for him, he didn’t even change his Lyne shirt, but it was obvious that she didn’t care.

“Shall we go?”

Without waiting for an answer, Rachel grabbed her arm and exited the room, leaving me behind.

I followed suit, but it was immediately clear that I was out of the picture for the time being.

I followed them on the beach, and we walked for around 15 minutes. The two of them flirted in the front for the whole trip, and I, on the side, remained back in silence.

Finally, we arrived at a small gazebo on the other side of the island. It was completely isolated, with a breathtaking view of the horizon, which was now starting to be tainted red by the sunset.

Two bottles of wine and three glasses were waiting for us on a small table, and the only spots to sit were two benches.

Rachel and Jacob sat next to each other, with Jacob putting his big arm on her shoulders and her laying her head on his shoulder. I decided to go in front of them. I was clearly the third wheel.

The couple kept flirting in front of me as we started to sip wine. I could feel my cock trying to get hard, given the humiliating situation. For this reason, I decided to try to focus on the sunset and left the two of them talking.

“Beautiful, isn’t it?”

Jacob decided to include me finally. I turned my head and realized he was now groping one of her exposed boobs while both Rachel’s hands had disappeared under the table.

“Uh, yes, truly incredible. How did you find this place?”

“Oh, just walking around, this place is truly a paradise, you know. I will be happy to show you some more these days.”

Jacob was looking me straight in the eyes, clearly enjoying the empowering situation he was in.

“Oh, you are way too kind.”

He interrupted the eye contact and murmured something in Rachel’s ear. She giggled in response, licking her lips, and nodded. He then came back to me.

“I bet you are horny.”

“A little bit.”

“All day without release must be, though.”

“Yes, a little bit.”

“Oh, don’t play it down; I am so horny right now, and I cum just this morning. I can’t imagine how it must feel for you. Luckily, I have someone to help.”

As soon as he finished speaking, Rachel lowered her hair and disappeared under the table. It was too tall for me to see exactly what was going on there, but the sounds she started making were painting a very clear picture. He grabbed his almost-empty glass of wine and kept talking to me.

“You know I am kind of jealous of you. I wish I had your discipline. I wish I could be strong enough to be in your position and not freak out.”

“I mean, I don’t know what to say.”

I felt my lust growing again, and subconsciously I tried to grab my dick again, but I was well aware of how useless it was.

“There is nothing to say. I am proud of you. You did your job; you prepared her for me, and now you can finally enjoy your prize. Can you pour me some more wine? I would do it myself, but I am a bit busy.”

He offered me his empty glass. I automatically grabbed it, got up, and started filling it up. From this position, I could finally see the back of Rachel’s head going up and down, gobbling on his huge dick.

“You like what you are seeing? Or do you prefer the sunset?”


“You know you could get closer if you wanted; you just have to ask.”


A rush of excitement went through my body. I was horny as never before.

“Can I watch more closely?”

“You sure? The sunset is truly beautiful! Or do you think your girl sucking my big cock is better?”

“I think your cock is better.”

“What a cuck! Alright, granted, but you owe me a favor, alright?”


“Go. Kneel under the table.”

I silently obeyed, too horny to think in my head. I lowered my head, and I saw it. Rachel was gagging on his big cock. Saliva was smeared all around the shaft through his balls. She didn’t stop; she was too focused on worshipping his big pole.

I silently got closer, mesmerized by the vision. My cock was desperately trying to get hard, uselessly. The smell of cocks and sex was filling my nostrils.

The sound of Rachel’s blowjob is filling my ears.

Suddenly, she decided to step down on the bench and join me on her knees. She stopped sucking just for a second, and I clearly saw her face full of spit and the ruined mascara. She looked at me smiling, grabbed my head, and gave me a sloppy, passionate kiss.

In a trance, I replied to the kiss, the unfamiliar, savory taste of cock completing my sensory overload.

A voice came from above.

“It’s time for today’s lesson, cuck. It’s time for you to learn how to participate in sex. Not like this; don’t distract your girl from her duty. You can either pleasure your woman with your mouth or help her pleasure the bull, but this is something not all bulls will accept. In both cases, you must ask politely.”

I looked at Rachel, who was now back to her duty.

“May I serve you, miss?”

She giggled with the cock still in her mouth.

“Glub, yes, but… glub, first you gotta get these clothes off.”

Hearing these words, Master got up, removed the toy from my love’s mouth, and stayed still next to the table. Rachel followed immediately, got next to him, and started kissing him while stroking his cock.

I got up as well, and while trying not to disturb, I removed the one piece from her and put it on the bench. Rachel was now completely naked, if not for the G-string; her legs were all wet from excitement.

Jacob pointed down, and I immediately knew what I had to do. I have watched many videos about this in the past.

I laid on the floor looking up, and Rachel got on her knees, putting her pussy on my face.

From there, I could see perfectly what was going on, but I didn’t care. All I was caring about now was pleasing my woman like I had just done an hour before. I moved the panties to the side and immediately began licking, putting all my effort into it.

Everything else disappeared; I was in a weird state of ecstasy. From time to time, I could feel saliva from the blowjob above me dripping on my head and getting mixed with her juices, leaving on my tongue a mixed taste of cock and pussy.

After an indefinite amount of time, Jacob announced that he wanted her.

“Get up, and you cuck, kneel in front of us.”

We both immediately obeyed.

She started grinding her ass on her cock, and he started kissing her on the back. His right arm was tight on her neck, and the left one went directly to her pussy. She started moaning, and I could see how much she loved this.

He mumbled something in her ear, and she got even wetter. They both looked at me and smiled. He pushed her back down, and she was forced to grab both my shoulders in order not to fall. She was now in front of me, her lusty face centimeters away, a dumb smile, saliva, and messed-up makeup covering it.

Suddenly, her expression changed: he had entered. She started moaning in pleasure harder and harder. I could see Jacob from behind, moving his hips with a focused face.

Her face was truly wonderful–a blissful expression I had never seen before. This time, I kissed her. Our tongues got together as I felt her head slightly moving with every thrust.

Jacob must have liked what she was seeing and started fucking her faster.

She started cumming time after time, and I was happy for her. I could see in her face how much she was enjoying it, and I was just glad I was part of it. The feeling of excitement was now constant. At every kiss and every moan, it grew a little more, but I focused on my duty and rejected my urge to stroke. After minutes that seemed like hours, Jacob grabbed her neck and pulled her up.

They were now fucking standing up in front of me. I had the full view of her majestic body; her huge boobs were bouncing every second. I looked at Jacob’s face, which appeared right behind her. He smiled.

“Lick her clit, cuck.”

No need to say it twice; I crawled a bit forward and obeyed. I could taste, once again, both her juices and his cock. His balls were bouncing on my chin, but again, I didn’t care. I just wanted Rachel to feel pleasure.

The position must have been incredibly exciting for Jacob, who started thrusting faster and faster in her. She was screaming in pleasure; I could feel her body shaking. Finally, I heard a grunt, and I knew my duty was finally done. I tried to get back, but Rachel grabbed my head and kept it still.

Jacob removed his cock, and my love forced her pussy into my mouth. The salty taste of sperm filled it. I wanted to spit it out; I wanted to say this was too much, but Rachel started caressing my head, and all of my thoughts disappeared. I knew that’s what she wanted me to do, and I was ready to do anything to please her at that point.

I gulped it all up, load after load. Jacob came quite a lot, and I did my best to scoop up any single drop in the trance of lust I was in. Finally, my mistress was satisfied. She let go of my head, and I finally came back to reality.

Jacob was back at the table sipping on his wine, trying to get back from the orgasm. Rachel also looked very tired. I am sure the multiple orgasms had something to do with that. I, on the other hand, was full of energy and in need of a release.

Only one question was now filling my mind: Had I been good enough to earn it?


To Be Continued…


*This story has been edited by AI to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.


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