Read Part 1 Here
Read Part 2 Here
Read Part 3 Here

*****

Chapter 10

The following day, I woke up incredibly refreshed; finally, my balls had been emptied.

I kissed Rachel good morning and started getting ready for the day, fully energized. I didn’t know when or if Jacob would show up, but this time I was ready. The program had been tough so far, but the rewards had made everything worth it so far.

A shiver of excitement went through my body as I thought about the previous evening and the powerful orgasms that came with it. I couldn’t lie to myself: I liked what had happened, and I wanted more.

As I was looking at myself naked in the mirror, I was woken up from my thoughts by a strong slap on my right ass cheek and a kiss on my neck.

“Last night was so good… I didn’t know you had this in you.”

Rachel had gotten up, and she was already horny.

“I didn’t know YOU had this in you.”

I replied with a smirk while kissing her back.

“Oh, me neither… But I liked it so much. You have no idea how much it turned me on turning you into my little bitch.”

As she was speaking, I could feel her nails running on my back. My cock got hard again immediately.

“Mmm, you have no idea how much it turned me on to be it.”

“Oh, I have a very clear idea. I saw you yesterday evening, and I am seeing you now.”

She suddenly took a step back and gave me another slap on the ass.

“But stop for now. We will explore your interest another time; we gotta get ready now.”

She was such a tease.

“Alright, alright. Do we have anything to do this morning?”

“I guess Jacob will show up sometime soon. Let’s grab something to eat in the meantime; I am starving.”

We got ready together. Cherishness had substituted the sexual tension that was there before. We pranked each other and laughed out loud together so much that it took us almost an hour just to get ready. The new experiences were making us grow closer than ever, and I was feeling in love like it was the first day.

She put on a very skimpy pink bikini while I went with the usual, but this time, I felt creative and chose a green shirt.

I got secured up again, and we headed out for our usual table, where we enjoyed a light breakfast.

“It’s crazy how it is only our fourth day here, isn’t it?”

“Truly, I have had more sex here in the last 72 hours than in the last two months with you.”

“I mean, it is not my fault.”

“You are right; you insisted so much for us to come here, and now I can totally say I am glad you did. I feel like we are getting closer, and hour-sex life is significantly improving.”

“Easy to say for you; I was the one ass in the air yesterday.”

“Like you didn’t like it.”

“Fair.”

“I started to see what Jacob was saying the first day. Maybe he was right.”

“About our roles?”

“I mean, yeah. I had some of the most intense orgasms of my life these last two days. Maybe this is the right path to follow going forward.”

This statement made me freeze for a second. Sometimes, it is scary to think that your fantasies might become reality. She picked up on my hesitation and added: “Are you not enjoying this? I just said that because I thought… ”

“I am enjoying it so much, you have no idea. It’s just that it is scary to change so much so soon.”

“Totally agree. That’s why I feel so lucky to have chosen Jacob. He is truly an expert. We will also have to share with him what happened last night. I am very curious about his feedback.”

The idea of sharing with another person my little experience terrified me, but in the end, I was aware that this was the way it was supposed to work, and he was here to help us explore these kinks of ours. More than that, it’s not like I have to see this guy ever again after we leave this island.

I nodded and went back to eating, enjoying the sun of this slow morning.

We went on chatting for a while. We discussed in more detail what we liked and what we did not, and we would have liked to experiment going forward. Unsurprisingly, at this point, Rachel was completely drawn by Jacob and ready to experiment with anything he was suggesting while also being incredibly intrigued by my submissive side.

We also discussed the month of preparation that she had done online before coming here, and, to my surprise, my imagination had gone way beyond reality. She had, in fact, simply spent a month learning about the basic terminology and practices of cuckolding while choosing the teacher for the vacation. She was very sad about the secrets she had kept from me, but she was right in saying that if I knew that, I would have probably tapped out before landing a foot on the island.

Our tête à tête was interrupted at around 11 when Jacob finally showed up smiling as always, wearing nothing but a white t-shirt.

He was quite clearly hungover, probably from some party around the island. He took a very long, dark coffee with a full English breakfast, listening silently while Rachel was filling him up with the events of the previous evening.

Only after she was done with everything did he glance at me and give us his feedback.

“So, Jack, you like anal? That’s great news for you! Surely, chastity can become more bearable if you are willing to use your hole as a relief. I told you it was the way to go.”

I turned red, not ready to admit how right he was. Luckily for me, he didn’t wait for an answer.

“I think you should go and buy an anal plug at the shop this afternoon. Actually, this could be your task! Yeah, yeah, I like the idea. Go there, say it is for you, and ask for some suggestions. Maybe you could be a sweetheart and also get a lubricant for me. Of course they will already know your situation and not react as people out there would, but it could be great practice for you when you have to do it in the real world.”

I looked at him with my eyes wide open, then looked at Rachel.

“She… she is not coming?”

“Well, if it is okay for you, I would have other plans for her training this afternoon.”

I looked again at Rachel, and her eyes were begging me to say yes. I knew it was useless to complain.

“Well… alright…”

“Great!”

He immediately got up with renewed energy and offered his elbow to Rachel.

“We shall immediately start then; you take your time. Let’s say we meet here at 4 p.m. Don’t be late, and make sure to be wearing your plug when we meet!”

“Byeee Cuckyyy, I will miss you.”

And like that, they walked away without giving me a chance to reply. I remained baffled for a minute, internalizing the task I had in front of me and the fact that I had more than four hours in front of me to spare.

My mind started running. What were they going to do without me? Sex, of course. Images of Jacob’s huge member inside my girl started filling my mind. A shiver of excitement went through my body as I felt my cock pressing once again against his cage. What kind of man gets horny thinking about his woman with another guy?

I started pondering everything that had been said in the past few days. Maybe I truly was a lesser man; I had to get used to it. One was saying it in the midst of passion, and another was truly accepting it.

I stayed there thinking for at least 30 minutes before waking up from the spell and deciding it was actually time to fulfill my task.

The trip was uneventful; I was used to my exposed cage and stopped caring about people seeing me in it.

I walked again in front of the swimming pool, finding once again people having sex in it, this time Lucy and Nick swapping with the same couple I had seen last time while we were having lunch.

It may have been my imagination, but I am pretty sure that Lucy noticed me and started moaning louder while looking in my direction. I was not really interested in talking with her at that point, and I just kept wandering, keeping my eyes down.

I entered the shop, and unfortunately, another couple was already there browsing for some new kinky ideas.

The guy was taller than me, quite skinny, but toned with visible abs. He had a completely shaved head and piercing black eyes. His body was full of colorful tattoos from the neck down, hidden partially by a white tank top. His cock, needless to say, was huge, hanging freely between his legs.

Next to him, there was a girl who could have been straight out of a porn shooting. Incredibly in shape, her boobs and ass were so perfectly sized that it was quite clear she had had multiple surgeries. Her head was the same: long blonde hair covered a face straight out of a TV show. Puffy lips, a perfect jaw, incredible features, and blue eyes. Both her shorts and tank top were bright pink.

I smiled at them and went straight to the counter, hoping to just get over it quickly.

On the other side, a splendid girl dressed in a “Sizequeen Resort” branded overall smiled at me and asked if she could help with anything.

“Hello! Yes, actually…”

I took a deep breath. “I am looking for…” Just get it out. “A Butt plug for me and some lube for the man who is fucking my girlfriend.”

The couple turned to me and giggled; the lady, on the other hand, froze for a second and then very professionally replied.

“Very well, any preference in size?”

“Uh, I guess small.”

“I see. So for beginners, we don’t have too much choice, but let me take a look… Here.”

From a counter, she grabbed small plugs and displayed them in front of me. They were all in stainless steel; the only difference was in their base: a circle with a red “gem” and a small bell attached to it, a pink heart, and a small rectangle with the word “slut” written on it.

I gulped, looking at the possibilities; none of them were ideal.

“Oooo, the “Slut” one is actually very kinky; do you have it in bigger sizes?”

The girl interrupted my thoughts.

“Hi, sorry to disturb you. I am Tami, and he is my husband, Samuel. I don’t think we have met each other yet.”

“Oh, yeah, my bad. My name is Jack. It’s very nice to meet you.”

I forced a smile on both of them.

“Yeah, actually, we met your girlfriend at the party; we were very curious to finally meet the cuck.”

“Oh, well, here I am, I guess. Unfortunately, I couldn’t join last time.”

“Oh, no need for excuses; we have partied quite a lot with Jacob these last few days. We vaguely understood the situation.”

Samuel interrupted me. Catching my unease, he immediately continued.

“Oh, don’t get me wrong. I think it is super interesting to see what is going on here. My lovely Tami here went through a similar path before, so we are the last ones that could ever judge you.”

I looked puzzled at her, who promptly replied.

“You know, I used to go by the name Tom. Look at me now! I started just like you! With a plug and a chastity cage.”

“Oh, there must have been a miscommunication; I am not in… you know… nothing bad with it, of course, but…”

“Of course! Far from it.”

She replied, squaring up my body.

“If only I had a body like yours when I started… anyway. I don’t want to disturb your absolutely legitimate shopping. If you ever want to talk about… this kind of stuff, we are here, and we would love to help… or play.”

They both smiled fondly and then diverted to the selection of plugs the clerk had taken out for them.

The degree of humiliation was already high enough for me. I quickly opted for the heart plug, thinking it was the lesser evil, grabbed the lubricant, and, after politely saying bye to everyone, left the shop.

I decided that the best I could do was get back to the room, a safe haven where I could rest and prepare for my meeting later.

Once I arrived there, my dreams were shattered. As I was going to the door, I heard loud moans coming from inside. Rachel was quite clearly “training” with Jacob.

I froze at the door, not really sure what to do. I knew they had asked me to meet them later, and I surely didn’t want to join in. Maybe I wanted. Every moan was making me hornier, and I could feel my dick straining against my cage.

I stayed a couple of minutes at the door, completely still, fantasizing about what was going on inside. My hands couldn’t learn from experience and were once again working against my cage uselessly.

Shortly after, I had the lucidity to understand that if someone had caught me in that situation, it would have been too much to explain.

Chilled by the possibility, I started walking, a bit sad about the end of the spectacle.

I wandered around for a dozen minutes before deciding that my best option was moving to the beach. I found myself in a pretty isolated spot and laid down, trying to enjoy some sun. Unfortunately for me, it was too late to simply enjoy the day; I was too horny for that.

For the second time today, images of Jacob’s huge dick and Rachel’s face kept filling my head.

I went straight to my new toy. Without thinking twice, I lubed it up and inserted the cold piece of metal in my hole. It slipped in quite easily, thanks to the stretch of the previous day, and when it fit, a wave of pleasure went through my body.

I was now caged and plugged on the beach, horny, thinking about another man fucking my girlfriend—an absurdity just a month prior.

I looked around, making sure nobody was close. Then, I slowly started playing with it with one hand while squeezing my nipples with the other.

The low levels of pleasure coming from these two moves were devastating for my horniness. The more I moved, the more I thought about Rachel; the more I got horny, the more I got desperate for relief.

After what felt like hours, I had to force myself to stop. There was no way I could spend my afternoon just doing that.

I got up while leaving the plug in me and went for a bath, hoping that the cold water could help.

It did. I was finally pacified, and I was able to go back to my spot and get drowsy under the sun.

“Look at who’s there! How does my favorite cuck doing?”

The voice of Lucy drew me back to reality.

“Oh… hi, Lucy. I am doing just fine, and you?”

“I am doing super! I am waiting for Nick to join me on the beach. That guy takes hours to get ready. Like if he needs to wear anything to go out. Would you mind so much company?”

“Uh, not at all. I am actually trying to kill a couple of hours.”

“Oh, I see. Where did you leave your girl? Fucking with the stud?”

My face turned red at the question.

“Actually… yes. I am pretty sure. They said they were doing some training.”

“Ahh… Some training… I see. I hope Jacob will train me some time soon. Does it train you as well?”

As soon as she said that, I squeezed my ass, and the plug reminded me of his presence. Fuck. There is no way she is seeing me with that on. I awkwardly adjusted myself to hide it better while trying to scramble an answer to this impertinent girl.

“Yes, I mean no, I mean yes, but not the same training.”

“Actually, about that. How does it work in your weird relationship? He fucks her, and you say, Thank you?”

Too much is going on; I was going to tilt soon.

“No, no. It is way more than that. He is like a teacher. He is, like, trying to expand our horizons in terms of sexuality while trying to make us discover our likes and dislikes. He is strengthening our relationship by showing us how to accept our kinks and indulge in them.”

“So… He fucks her, and you say thank you because this is what you like?”

“Pretty much, yeah.”

“Cool. She is a lucky girl.”

“We can say that.”

“And you are a lucky guy. With a small dick like that, how did you land her in the first place?”

“I… uh… my charisma?”

“She didn’t like to fuck with you, didn’t she?”

“She never complained.”

“How often were you doing it?”

“Once every two weeks.”

“Ouch.”

“Come on. It is not like that.”

“Oh, it is. I am happy for her; she found a good dick. You should be happy as well.”

“Can you stop molesting this poor guy?”

Nick’s voice emerged behind him. Never have I ever been so happy.

“I am not molesting this guy. I am helping him fit his new role. He invited me to join him.”

“For real?”

“Uuh, we can say that, I guess.”

“Plus, this pervert loves getting humiliated. That’s what his girl said, remember?”

“She said what?”

“She was really drunk. I am sure she was joking. Come on, Lucy, let’s leave him alone.”

“We were having so much fun! Also, he said he had a couple of hours to spare because Jacob and his girl were fucking like crazy, and he was not invited. Come on, sit with us.”

Nick couldn’t hide a smirk from this last statement and agreed to join. At this point, I was trapped by social conventions and surrendered to the idea of spending the afternoon with the couple.

They sat in front of me, Nick with his legs open and Lucy next to him. As soon as he sat down, she started caressing his dick while being unable to keep her eyes away from my cage. I sat, careful not to show what I was hiding, and tried to have some small talk with them.

It worked for a bit: we talked about soccer and what activities are available on the island, but inevitably, the topic went back to my condition. This time, Nick was the one to bring it back.

“Does it hurt?”

“What?”

“The cage.”

“A bit, but only when I get hard. At least try to get hard.”

“Oh, that must suck so much. Why are you wearing it?”

“Island policy. Cucks aren’t allowed to just go around and bother girls with their small dicks.”

Lucy felt the need to reply.

“Yes, but not only that. My teacher said that it is very useful for me to understand the power dynamics and redirect my sexual energy.”

“Oh, interesting. And how is it redirected?”

Nick’s interest peaked.

“To pleasuring others.”

I saw a small bump on Nick’s cock. Lucy caught that as well and redirected his attention to it.

“Please tell me more.”

“I mean, it is quite simple. He is teaching me to deny myself and use that energy in pleasuring them during the act, as it couldn’t be any other way.”

Lucy had now begun stroking with one hand, his cock right in front of me. He, on the other hand, was keeping eye contact like nothing was going on.

“So, you are saying that, as you can’t please your woman, he is teaching you the best way to act while someone else is doing so.”

“I mean, I take part. Not the active part.”

“You don’t do the fucking.”

“I don’t. Yes.”

The conversation was clearly arousing Nick, who was now sitting fully hard in front of me.

“Wow, this is so erotic; do you mind if…”

He grabbed Lucy’s head and gently pushed it on his dick. She was clearly quite horny herself and started immediately sucking passionately.

“Oh, not at all, please.”

“You are very kind; I would offer to share, but you know.”

“Understandable.”

“And how do you deal with that?”

“With what?”

“With the fact that you are not man enough to fuck your woman properly,”

The sudden aggressiveness took me off guard. I didn’t really know how to answer that.

“I am sorry. I am sorry. I got carried away. Lucy’s mouth brings out the worst in me. It is not your fault if you have a small cock. But cheers! I am sure you are learning tons of ways you could help without using it.”

“We haven’t really started on that yet, but I hope soon.”

“Ah, Jacob is slacking around. You should let me fuck Rachel. I could teach you so many things. Me and Lucy, actually.”

After saying those words, he grabbed Lucy by the hair and removed her from his cock by force. She nodded at him, then licked her lips while looking at me. He grabbed his dick and smacked it on her cheeks before slamming it back into her throat.

“So… What do you say? Let me fuck your girl. I swear, I am making her cum like never before.”

I was frozen by the situation but also hypnotized by the sex in front of me. Lucy had turned from quite dominant in the conversation to absolutely submissive in Nick’s legs, the man the other way around. The lust building was also making my head foggier once again.

“I mean, we still have three days and a half of full training with Jacob. Then I guess you should ask her.”

“Ah, great! I will remember that. Now sorry. I really have to fuck this bitch. You can stay and watch if you want. I mean, that’s all you can do, isn’t it?”

Without adding a word, he grabbed her by the neck and threw her on the sand. She obediently put her ass up and moved her swimming suit, revealing her soaking wet pussy. He turned her head to me and looked straight into my eyes as she started taking the pundit.

Nick was rough. Rougher than I could ever expect. She started fucking her doggy style hard and fast from the get-go. Lucy was clearly enjoying herself, moaning hard at every thrust, losing interest in me almost immediately.

It was better than porn. I had the impression he was actually trying to film one, and I was carrying the camera. Every couple of thrusts, he would stop just a second and slightly tilt his back, allowing me to have a complete view of what was going on for just a brief moment. Then, he would smile like he was proud of what he was doing. I would have been really proud of myself if I were in his shoes.

My first instinct was to touch myself–maybe even play with my plug–but there was no way I was doing it in front of them. Instead, I remained watching, hypnotized, for a couple of minutes, then slowly got up and left the two of them to their business, covered in shame.

At least they didn’t see me plugged.

I went back to our usual table. It was almost 3 p.m., and I hadn’t touched food yet. I ordered alone and waited for the other two to show up.

*****

Chapter 11

At four, they finally did. Rachel was clearly happy and was almost jumping around him; Jacob, on the other hand, was playing it cool like always. He looked at me from far away and waved at me.

“Hello, hello. How are you doing? I hope you didn’t get too bored during our absence.”

“Oh, I am great. Actually, no, I enjoyed some quality time. What have you been up to?”

“Well, I explained to her the activities we will be doing together as well as additional instructions for them. We might have also started a bit ahead of time; I was hoping you would have joined us.”

They looked at each other and smirked.

“Actually, I heard you outside the door; I thought you didn’t want to be disturbed.”

“Ooh, you really are the perfect hubby!”

Rachel hugged me tight and kissed me on the neck. Jacob smiled and continued.

“We wouldn’t have minded; actually, I was hoping to see you there; we would have condensed these afternoon activities into one session only. Well, too bad.”

“What are the activities for the afternoon?”

“We are having lesson 1 of the Cuckold Kamasutra. I’m teaching you all the ways you can be part of the sex between your girl and the bull. I’ll tell you more back in your bedroom.”

I got up and led the way to our bedroom, but after just a couple of steps, Rachel burst into laughter.

“OH MY. I forgot about the plug. Look how cute he is, Jacob!”

I turned red in embarrassment as she got closer to me, spanked my ass, and spread my cheeks to better show my toy.

“Ah yes, I forgot. I asked you to do that. Very well. An interesting choice as well, and I am sure you will get very attached to it very soon. Did you also get my order?”

“Yes, teacher. It’s here.”

I handed him the bag, completely humiliated by Rachel’s reaction. Jacob didn’t make any other comments and continued on his way. My girl, instead, kept teasing me all the way through, keeping her hand on my ass for the whole short trip.

We entered the room and immediately noticed that it was incredibly messy. There was nothing I could say about that. Just a reminder of the situation I was in. Rachel sat on the bench as Jacob took the lead.

“So, cuck, we have covered the basics, but now it is time to put into practice the etiquette you have learned and expand on it. Sounds good?”

“Yes, sir.”

“So, we are going to act out a scene. We would act like I would like to be treated if this were a regular encounter between me and your girl. I have already given her instructions; you will notice it might be a notch over the usual fantasies, but you also need to be flexible. I will now go back to my room and pose the lubricant, as we will need it next time. This will give you plenty of time to prepare.”

I nodded, and Rachel did the same. As soon as he left the room, she jumped up and started giving me instructions.

“Come on, Jack, we have little time. Do the bed as I put on a touch of make-up. We need to make this place presentable.”

I silently nodded and got to work. She moved to a table next to me and started doing her make-out as she continued explaining.

“When he knocks, you are going to open, greet him properly, and I mean properly, then invite him in. After he has said hi to me, you are going to offer him some water, coffee, or wine; that’s all we have. If he says yes, you go; if he says no, you don’t say another word if not asked and go sit in that chair in the corner, understood.”

“Alright, alright.”

“Sorry, what?”

Her eyes pierced me.

“Understood, mistress.”

“Good boy. As soon as you are done, go in my luggage and look for some lingerie for me, the naughtiest you can find. Jacob bought me a bunch before, but I would like you to pick your favorite.”

“Yes, mistress.”

The now familiar sense of dizziness induced by horniness had started filling my whole body. I was in a trance.

I complied without saying another word. After cleaning up the mess I had done in the morning, I moved to the bag, where I found out what she was talking about. I looked at the possibilities despite the fact that there wasn’t much to look at. I scrammed around, trying to understand what these small pieces of cloth were supposed to be until I came up with a plausible outfit.

I went for the classics: white stocking and garter belt, white thong, and matching bra. It was not the naughtiest choice for sure, but Rachel went along with it.

I brought it to her, and she ordered me to help her put them on.

As she was securing the bra. I got on my knees and slowly helped her fit both stockings. I moved to the garter belt. The excitement was almost tangible. Her dripping wet pussy was inches from my face. I wanted to lick it so badly, but I behaved. Finally, it was time for the panties. I moved to her feet to put them on, but she gestured that they weren’t necessary.

Finally, she picked a pair of white heels from the closet, which I happily helped her fit. The outfit was complete.

I remained on my knees, observing how beautiful she was as she spun for me.

“What should I wear?”

“You? Nothing, of course! He likes having his cucks completely vulnerable.”

I wanted to complain, but a knock on the door silenced me immediately. She made the gesture, and I quickly removed my shirt before going to open it.

He was standing there, wearing a suit, against the rules of the establishment. His muscles were almost exploding in his tight overalls. He smiled at me.

“Good afternoon, sir. I’m so happy to see you here. Please come in.”

“Thank you, cuck. Ready for the occasion, I see.”

I took a step forward, and he gestured for me to remove his jacket as he locked her eyes on Rachel.

“You are truly gorgeous.”

As soon as I grabbed his jacket, he reached for her and started a passionate kiss while grabbing her ass right in front of me.

I silently hung his jacket and remained silent, waiting for them to be over.

“Can I offer you something, sir? Unfortunately, we just have water, coffee, and some fresh white wine.”

“Bring two glasses of wine. It’s crazy hot with this thing on; surely it will refresh me a bit.”

I left the two alone and went to the small kitchen. In the fridge, I found a bottle, probably bought by Rachel.

I quickly filled two cups and went back to the room, where I found them sitting on the edge of the bed, kissing. Rachel had one leg open on his lap, while Jacob had one hand deep in her pussy.

I gave them both a glass and obediently went to the chair in the corner. From my position, I could only see them halfway, but it was clear that the wine hadn’t stopped his hand.

They giggled and flirted for a couple minutes, but it was obvious that the sexual tension was peaking.

Suddenly, Rachel raised her glass over her head. I immediately made a step forward and grabbed it.

With now-free hands, she lowered her head, unzipped Jacob’s pants, and uncovered his monster.

Jacob tilted slightly towards me, giving me a better view of her servicing him, and started talking to me.

“Your girl has such a nice mouth. Does she ever do this for you?”

I looked at him, sipping his wine, and replied, drawing in humiliation.

“I know. Not really anymore.”

“Too bad. Come here. Kneel next to her.”

I silently obeyed.

“Her hair is on her way. Grab them.”

Once again, I silently obeyed. As she was starting to get messy while worshipping his cock, I took all her hair in front, being careful not to put my hands in her way, and used my right hand to keep them in a ponytail position.

As I was there, I had a perfect view of Rachel going up and down on his magnific shaft. The view was straight out of a porno. Her skills must have improved in the previous days, as she was clearly more confident than before, alternating slow moments of licking and teasing of the top with moments of passionate dick-sucking.

My cock was straining against his cage as I watched, in real-time, my love ruining her make-up under a very satisfied Jacob.

After a couple of minutes, it was time to change. Jacob introduced me to the second position of the day.

“Good job, cuck. Now it is time to go to work. Prepare you, girl, for me. Lie down, arms up.”

I nodded and complied. They both got up. Rachel smiled at me before sitting exactly over my face, putting her knees next to my chest and blocking my arms. Her dripping wet pussy was begging for attention, and I got myself to work immediately. I couldn’t see what was going on, but the sounds of gagging were painting a clear picture.

Suddenly, I felt a wet sensation on my chest. My cock tried to get even harder as I realized it was Rachel’s saliva dripping from the blowjob. My first impulse was to touch my cock, even in its condition, then to play with my plug, but my hands couldn’t reach either.

The position didn’t last long; luckily, our teacher had quite a lot to show me.

Rachel moved to the bed and got on her fours. First, he indicated that I should stand straight in front of her, on my knees at the border of the bed.

I was now facing her happy face, completely smeared with saliva, as Jacob was towering behind her.

“The positions I will be showing you don’t have official names, but I have created a couple over the years. I call this one ‘the couple in love.'”

I focused on Rachel. I was, in fact, so much in love at that moment. She was so happy that I forgot about everything else.

She smiled at me. She moved her right hand to my jaw and then kissed me. I closed my eyes, and everything disappeared. The taste of cock filled my mouth, but I didn’t care. The lust built up until now made me lose myself in the deep kiss I was having with the woman I loved. A truly blissful moment was only interrupted by a moan. Then another. Then another.

I opened my eyes and saw that Jacob had started moving behind her, slowly but steadily, while looking straight at me.

I brought my focus back to her. She grabbed my hand and whispered to me:

“It is so good.”

“I am so happy for you.”

I replied before gently kissing her again.

I spent the following minutes like this: caressing and kissing her as I was completely absorbed in every spasm of her face.

“There is a variation of this. Go sit on the chair.”

I snapped out of the spell I was in and silently obeyed. At that moment, I would have done anything for that man.

As soon as I sat down, Rachel followed me. She stood straight in front of me and bent, laying her upper body on my lap. Jacob followed soon and resumed what he was doing.

From this position, I had a real clear view of the action I was missing, and, to make matters worse, Rachel grabbed my almost exploding dick and held it tight, making it bump at every jam.

I endured the situation, as there was nothing else I could do.

Things only got more extreme from there on.

First, while keeping that position, he asked me to spread her cheeks to facilitate his action. Her moans got even louder, and I am pretty sure that this was when she got her first orgasm.

Then Jacob got tired of standing up. She ordered me to lie on the side of the bed. Rachel put her head on my stomach, and Jacob started fucking her missionary-style right over me. First, I was forced to look intensely at his cock fucking her, then he asked me to hold her legs up for him. I lost count of how many times my love said she was cumming during that second position. At this point, I was in automatic mode. I just wanted to cum; I didn’t care about anything else. I also knew that achieving their pleasure was the only way to get mine.

Then, it was time for the grand finale. I lay down in the middle of the bed as my girl put herself in the ’69’ position with shaky legs. Her pussy was right in front of my face. Soon, Jacob’s monster was as well.

“You have been such a good boy for the evening; I think you deserve a prize. When I start fucking her, you are going to lick her clit. In exchange, you are getting out of chastity. Don’t touch yourself if not allowed, and DON’T FUCKING CUM BEFORE TOLD SO. If you do, you forget to cum again on this island. UNDERSTOOD?”

“Yes, master.”

And so the final act began. His huge balls were bouncing on my forehead as I licked passionately. My face was covered in any sort of liquid, but I didn’t care. The click I heard among the screams of pleasure was the only motivation I needed. My cock was finally free.

I felt a soft hand grab it as Jacob started a furious pounding. I was hard as a rock; I just wanted her to move that hand, but she didn’t. She cum again and again until, finally, I heard a groan.

One last pump. One last time, his balls were hitting my face.

Slowly, he removed his cock as a drop of cum hit me right next to my eye.

I had a full view of the gaping hole he had made in my girl. I stopped licking. Finally, it was over. I was ready to move, but Rachel had other plans. She moved her back and once again sat on my face, leading the cream pie straight to my mouth.

“Uff… This, my little cuck, is your last chore. Cleaning her, your girl, at the end of the intercourse is absolutely mandatory. It is the final duty: you both give your lady a final moment of pleasure while also showing your bull true respect. In the end, everything that had just happened was because of you. You truly earned it.”

He paused.

“Then, when you think her pussy is spotless, you can get up and reclaim her.”

Say no more. I put myself to work. I licked and sucked. The salty taste filled my mouth. Jacob had clearly cum quite a lot.

While I was doing so, Rachel was slowly grinding on my face while slowly jerking my little cock.

I made a gesture signaling I was done, but Rachel wasn’t with me. Despite what was promised by Jacob, she put even more weight on her lower back and started stroking my dick with a tight grip while riding my face faster.

15 seconds were enough for me.

The orgasm was as intense as the ones I experienced the previous days, only this time, it lasted longer as an incredible new sensation persisted around the plug in my ass.

I zoned out as the devastating post-nut clarity hit me.

*****

Chapter 12

When I recovered, Jacob had already left. Not that he had stayed for long after cumming in Rachel.

We were finally left alone, extremely tired, with no cognition of how much had passed since the beginning of the class.

Rachel hugged me from the side and fell asleep quite quickly in my arms. I followed soon after.

We woke up at around 8 p.m., hungry like crazy. We didn’t talk much; we were still too tired. Shower, some random clothes, that damn chastity belt, and we were out begging for some food. Didn’t even consider the plug this time.

We approached the dining area, and it was there that disaster struck. Right next to where we usually hide from the other vacationers, we found Jim, Sakura, Tami, and Samuel happily enjoying their dinner in their skimpy pajamas.

I immediately tried to change direction, but it was too late. Tami had spotted us and was now waving in our direction.

“Hey guys! It’s so nice to see you! Wanna join us?”

I looked at Rachel, annoyed and saw she was matching my vibe.

“Hey, everyone! We would love to, but we are so tired. We had such an intense day.”

“We did as well!”

Samuel replied this time, with everybody else chuckling behind him before he continued.

“No worries! We are just here for a light talk before calling the night early! You both have been so elusive since you got here, and we would love to get to know you better. We don’t bite, we promise!”

I looked at Rachel. She was thinking about it. He was kind of right about it; apart from some brief conversations and that crazy experience I had with Lucy and Nick, we had done nothing to be part of the daily activities with the excuses of our “program.”

She touched my shoulder, and with a glimpse of an eye, I understood we had reached the same conclusion.

“Well, if you put it like that, how can we say no?”

Rachel smiled, and we joined them.

The beginning of the evening turned out quite well. It was nice to take a break from the cycle of perversion we were stuck in and talk about something different. I discovered that me and Jim were actually doing a similar kind of job, and we spent quite a while a while talking about the possibility of careers, as he had 15 years more experience than me. We also discovered that we had a common passion for trips to exotic countries; it was, in fact, during a trip to Vietnam just six months prior that he met Sakura, who was there in Erasmus for her university of design. The same passion was also shared by Samuel, who spent a solid 45 minutes telling us about the crazy trip he had done around the world. Tanzania, Nepal, Japan, Mexico, Mauritania, and so much more. Crazy what having a fully remote tech job allows you to do. Tami had joined midway through. A childhood friend of Samuel had fallen completely in love with his spirit and, during the years, had allowed him to shape her in many different ways. It was this specific topic that was the turning point for our night.

“So yes, slowly but surely, I went from Tim to Tami, and I couldn’t be happier. I am so free, thanks to Samy, and I couldn’t be happier. Also, look how fucking hot I turned.”

She had a point; she was fucking hot.

“Thinking about how it all began seems like ages ago. But it was like you, Jack, with my plug and a chastity cage. But you already know that.”

I turned completely red in shame. I hadn’t had the chance to tell Rachel about our encounter yet, and being exposed like this was beyond humiliating. Rachel giggled, and both Sakura and Jim looked puzzled at me.

“No… no… I already told you… I am not really into…”

“I mean, the chastity; I can see it from here. Wasn’t the plug for you?”

“I mean… yeah… but Jacob said it was for the training… it was my first time.”

“I mean, it’s not like he is forcing you. I bet you loved going around with it.”

“Tami, come on, stop grilling him. You know that at the beginning, it is hard. Don’t be a douche.”

Samuel intervened.

“Oh, no worries. We are still exploring our kinks; our experience can only be enhanced by such ideas. I gotta say I never thought about my sweet Jack like this.”

Rachel jumped into the topic, seeing me too stunned to speak.

“No, no, Samuel is right. These things are probably coming out of me because I am a bit jealous. He has a body structure that I wish I had. With a couple of touches here and there, he could become such a baddie.”

“I mean, don’t take it wrong, but I would fuck you already.”

I looked at Jim, speechless. This comment hit me in such a weird, flattering, and humiliating way.

“Well, thank you. I guess…”

“Now that you say it, you are right. He has nice buttocks, a lean torso, and nice legs. Damn, I was staying with a hottie, and I didn’t even notice it.”

“Rachel! Stop it already!”

I couldn’t get more embarrassed by the conversation; it seemed, on the contrary, that Rachel was having a good laugh at my expense.

“Come on, everybody. Jack is already going through a lot.”

Finally, Sakura came to the rescue.

“You are right. Still, there is nothing to be ashamed of.”

Tami closed the argument. Once again, she was probably right. I seemed to be the only one to be weirded out by the topic. Everybody else, Rachel included, was talking about it like it was absolutely normal. Probably for people like them, it truly was normal.

“They are learning to expand their horizons. Give them time. By the way, I am very curious about how this whole program works; would you mind sharing a bit?”

I wasn’t really ready to talk so openly about it with strangers, but I wanted to try to match the vibe. I gestured to Rachel, and she started explaining.

“So basically, it is a full immersion cuckold program. I have selected a bull who is also working as a teacher and is introducing us to the world of cuckolding this first week. I was very skeptical at the beginning, but now I am completely sold. Jack is also having loads of fun.”

“Easy being sold to a dick like that.”

Sakura commented, giggling; I could see Tami was agreeing. This time, Rachel was the one turning red.

“I mean, it is not only that. I see it is a selling point for sure, but he is also very good on both the physical and psychological sides of things.”

I had to intervene.

“So what do you do? Stay there and watch. Do you like it so much?”

I was starting to get tired of this sort of question everybody seemed to be having.

“Not only that. I am learning to serve both of them while finding pleasure in being denied. I have to admit I got some of the most potent orgasms of my life.”

It was the first time I was so close to admitting my enjoyment out loud in front of Rachel, and it felt kind of liberating. Both Samuel and Jim seemed pretty interested in what I just said. The first one was the quickest to speak.

“Wow, interesting. So what do you do while they fuck?”

“Mmm… for the time being, not much.”

“Today, you did a bunch of stuff.”

Rachel had less shame than me.

“First, he got me ready for Jacob, licked my pussy while I was sucking his cock, held my hair while I was sucking his cock, cuddled me while he was fucking the shit out of me, licked my clitoral while he was fucking the shit out of me… what else?”

She took a pause and got closer to me.

She was clearly getting hornier while thinking about it.

“He also licked his cum out of my pussy when Jacob was done.”

“Damn, girl! Here you go!”

Sakura was the first one to speak, but clearly, everyone at the table had gotten a bit worked up by the story despite nobody thinking about being in my place.

“I had no idea… well, I, I mean me and Sakura, would love to explore more of this, if you guys are interested.”

“Same for us.”

I looked at Rachel, a bit embarrassed, despite the fact that the fact that I was getting a bit worked up at the idea, despite not yet being ready to admit it.

“I mean, we still have to discuss this. We are still in the training phase, in which we are not allowed to play with anyone except Jacob for the next three days. Still, we will think about it and tell you next time we see each other.”

“Sad.”

“Sad indeed. We will wait.”

Jim and Sakura were truly disappointed. Jim, on the other hand, had still more questions to ask.

“What about that cage? Does it hurt? You must be consistently horny.”

“It does, slightly, and yes, you have no idea how much. My master had been quite generous so far, though, and I must say I was allowed to cum both today and yesterday.”

Only after saying the words did I realize how they sounded.

“Wow. I could never.”

“You truly could never love. I don’t think you could ever fit into such a small mechanism. How long is it? 3-4cm?”

Sakura replied. I looked down and looked at my situation.

“Yeah, not sure, but pretty much.”

“Only small cocks belong in chastity. That’s what Jacob always says.”

Rachel added, smiling with a disarming innocence.

“Real sissies should come from anal only. The sooner you realize that the happier you will be. You can trust me on that.”

Tami finally added. Being called a sissy added injury to the insult. I was starting to get annoyed. One thing was being treated like this in a safe, sexy environment, and the other was being insulted by random guys. I knew neither of them really meant any harm, but I was not ready to receive such treatment. Tami probably noticed this and wisely tried to change the topic.

“What about you, Rachel? Have you done anything new and exciting since the beginning of this training?”

“We have done some varied rough sex for sure, which was new for sure. Tomorrow, we got some very kinky plans, actually, but I don’t want to spoil them for Cucky.”

I looked at her, and a rush of excitement went through my body. Sakura expressed her jealousy of having such an exciting week, with something new for us every day, but neither she nor anyone else kept digging about it, and the argument was dropped. After that, the phase of the night where I was uneasy was over. We went back to average chit-chatting, only a bit kinkier than before. Jim told us about the many BDS experiences he had; we discussed the pleasures of anal sex, something Rachel had never done before, and we closed on “the rush of being in the middle of a gangbang.”.

After that, everyone was quite toasted. We said goodbye to everyone, and we went home. Both I and Rachel agreed that it was a very pleasurable night and we should have done it more often. The spirit was high again, and soon we fell asleep while cuddling.

 

To be continued…

 

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