Sizequeen Resort Pt 04

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 have shown up, but this time I was ready. The programme 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.

"Yesterday 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.

"Mmmh, 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 mean time; 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 yesterday night. I am very curious for 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 were liking and what we were 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 for the secrets she had kept 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 hangover, probably for 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 he glanced 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 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, internalising 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 fulfil 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 colourful 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 hairs covered a face straight out of a TV show. Pluffy 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 splendind 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 buttplug 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 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.

"Oooh, 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 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 got 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. Evey 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, fantasising 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 for 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. 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 a way I could spend my afternoon just doing that.

I got up while leaving the plug in 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 is my favourite 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 have you left 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 has a couple of hours to spare because Jacob and his girl are 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 carressing 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. Cuck's 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 tonnes 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 in 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 hypnotised 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.