Sizequeen Resort Pt. 02

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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 was that 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 own 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 go grab something to eat with our new friend. The 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 have a discussion about. 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 laid 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?"

"Yep."

"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?"

"What?

"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 putting on my make-up. 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 cummed 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 breath-taking. 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 breath-taking view on the horizon, which was now starting to be tainted red by the sunset.

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

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 finally include me. I turned my head and realised 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 at 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 cummed 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."

"I..."

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 favour, alright?"

"Sure."

"Go. Kneel under the table."

I silently obeyed, too horny to think in my own 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, savoury 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. There were so many videos I had watched in the past about this.

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 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 on order not fall. She was now in front of me, her lusty face centimetres away, a dumb smile, saliva, and messed-up make-up 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 at 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 as well looked very tired. I am sure the multiple orgasms had something to do with that. I from the on the hand I 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.

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13 Comments
AnonymousAnonymous8 days ago

Pls add more bbc and jack being humiliated by other women.

Shib7534Shib75348 days ago

Very much enjoyed the journey so far. Please continue the story. Hoping to see jack craving for sissygasms by bbcs.

AnonymousAnonymous15 days ago

This is a fun and sex story. Tropical paradise, away from all of the things like jobs, family, neighbors that keep us tethered in place. The fact that in the first story the action starts with the cuckold’s girlfriend having participated in some programatic deceit, spending a month preparing and leaving him in the dark about it, and then their forgetting to set a safe word actually does spoil some of the pleasure for me. It simply leaves open the possibility that he may feel regret or recrimination. I’d rather he had the safe word and could choose not to use it than have it occur to him to have been an oversight. I don’t know whether these issues resonate with any of your other readers and or if there is any way for the couple to process or discuss these issues or set a safe word as they proceed with their stay at the resort.

Good luck with next chapters

AnonymousAnonymousabout 2 months ago

When are we going to get the next part

AnonymousAnonymous2 months ago

please include watersports and more humiliation

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