Sizequeen Resort Pt 05

Chapter 13

We both woke up late in the morning after one of the most satisfying sleeps of my life.

I knew we had the full morning completely for ourselves, so we decided to take full advantage of all the amenities of the resort that we had avoided so far.

We hit the gym for a light morning workout. Training with my cage on was kind of annoying and must have looked quite goofy, but luckily for me no one was around to really notice. Rachel, on the contrary, took her time at the gym quite seriously, hitting a very intense full-body workout.

After the sweat came the relaxation: sauna, swimming pool, massages, sun bathing--we did the whole wellness tour completely unbothered.

At around 1 pm I was as relaxed as hungry, so we hit our usual spot for some healthy food as a cherry on top of our morning.

While eating, we started talking for the first time about what was said the night before.

"So you sure you don't want to be a sissy?"

"Quit it."

"Alright, alright. I didn't want to ruin the good mood."

"You haven't, sweety."

I smiled at her, trying to pretend I wasn't actually pissed.

"It's just the third time in 3 days I have heard this suggestion. I don't think it is really that plain and simple."

"I mean, it's just that I saw you with the dildo and then the hearth plug."

"Don't you realize how weak of a connection between the two things is? Tami just got in your head. Or maybe you just want to see me like that?"

Rachel raised her eyes up, but I knew I had hit the spot. She tried to deny quite quickly, but she couldn't keep up the facade too long.

"Maybe, and I say MAYBE, it excites me the idea of seeing my beautiful boyfriend in some skimpy clothes. MAYBE."

"You could simply ask."

"Would you wear some pants for me?"

"No."

"Uffff. I open up, and that's how you treat me? Can't I have a little kinky fantasy?"

"You are having quite a bunch of them lately."

"Look who's talking. Whose idea was this?"

"Whose enjoying it the most?"

"Hard to tell. Still, you had your request, and I made it reality."

"Yeah, yeah, but I indulged in everything you proposed after that. Moreover..."

I leaned close to her and put both my hands on the table, pretending to be making a scene.

"My original request had never been turned into reality."

"Wait, what?"

"Don't you think it is crazy I tried anal before you? After all this time."

"Again with this story... It's just not really my thing."

"How convenient..."

"Ok, here I am. I will give you my ass, but..."

"But..."

"Quite dumb of you to bring this out while we are here."

"Uhm. Maybe I got carried away."

"You know quite well you have a competitor. So you will have to earn this trophy."

"Ah shit."

"How little faith you have in me. It is quite easy to win, and you have all the advantages you can have."

"What do I have to do?"

"You just have to challenge him at something and win."

"At what?"

"At whatever you want, silly."

"Oh. Well, you were right, quite doable."

"Everything goes. I just want to feel like I am the prize. It is so nice to have guys fighting for you. I will not tell him anything. Think about what you want to do and do it whenever you see fit. Just make it a challenge where I can see the struggle. At least a bit. No rock, paper, scissors, let's say."

"You think I would bet your anal verginity at rock, paper, scissors??? Now you are having no faith in me."

"We'll see."

She giggled.

The challenge was now on. We spent the rest of lunch talking about something else, but my mind was there. I had to challenge Jacob and win; it was only about finding the right discipline. He was bigger than me, an ex-athlete, and yada yada, so something physical was too risky. I was aware that I had to beat him at something; it had to be about using my mind. But what?

The only game I was playing quite a lot was poker. I had played so much in my life that I was confident I could have beat at that, especially if I had the opportunity to call my shot whenever I wanted. I just needed to convince him to play and wait for the right hand. Easy peasy. I just had to organize a friendly game.

After lunch, we went to the beach to relax a bit. A lot of people had our same idea, in fact, we found the place crowded for the standards of the resort. I was quite worried to see both Jacob and Tami there, as well as other, never-before-seen people, but to my surprise, nothing special happened.

Nobody made jokes, nobody did anything remotely sexual, nobody was really feeling kinky. We went for a swim, we played beach volley, I introduced myself to the blonde girl I had seen before, Katya, without her asking a thing about my situation. A perfect afternoon. I should have been happy and relaxed, but I was not. In the back of my head, the idea that I had to prove myself was consuming me. Everything I was doing was reminding me how much Jacob was a better man than me. He was better at volleyball, swimming faster, and making funnier jokes. After a couple of hours, I exploded, set my plan in motion, and started organizing the poker game.

I proposed the activity to Rachel, and she said yes immediately, in part because she loved playing as well, in part because she had noticed my frustration. She suggested that I could

Ask Daniel for some help to organize it.

I left our companions and went on my quest. The person responsible for the activities was quite happy to help me set up the game, probably impressed by someone actually proposing something not related to partying and having sex.

He made sure to contact everybody at the resort and to collect their participation while coordinating with the shop for some prizes for the winners, more specifically 2 vouchers of different values for the two players with the most wins at the end of the tournament.

In particular, he made me know that Jacob had accepted.

At 4pm, 9 people showed up at the table reserved for us, who were on a patio next to the beach with a crazy view of the sea: me, Rachel, Jacob, Daniel, Nick, Jim, Matis, Gulia, and a guy who introduced himself as Adam.

I set down next to Rachel, on the opposite side of Jacob, and we started playing.

The resort had put at our service a member of the staff who, very professionally, served as a dealer the whole afternoon.

The game started very lax, with low bets and a lot of talking. Everybody was mostly talking about their recent crazy sexual experiences. Jim had had a threesome, Giulia had a ganbang, foursome anal for Nick, and so on...

Everybody was quite relaxed by days of sexual release, but not me. All these stories were just reminding me of how much on a mission I was in that moment.

After about 45 minutes, the worst happened: Matis asked Jacob if he had any crazy sexual experiences lately.

"I mean, I have been doing a bunch of stuff lately. Yesterday I had a threesome myself."

He said, smirking at me.

"Oh, really with whom?"

Matis asked while folding his hand.

"With the great couple in front of me."

"Oh really, so even Jack is having sex these days?"

"Oh no, no. He helped quite a lot with his tongue."

I buried my face in the cards as a fragurous laughter erupted around me.

Matis continued.

"Poor guy. Rachel, aren't you treating him a bit too harshly? Is he getting a little bit of pussy once in a while?"

"He is, sometimes. For a couple of pumps."

Once again, laughter. Never in my life had I been humiliated so publicly and without a reason. The conversation kept going as I folded hand after hand.

Everybody was quite interested in me and Rachel, and she was sparing no details about the activities of the previous days.

I was starting to get angry, but I knew I had to stay calm. This table was the perfect place to finally get a victory.

My moment finally arrived while Jacob was talking about the cuckold kamasutra: a pair of aces in hand.

Now it was my turn to talk trash.

"Come on, you talk like you have never been in my position before."

I said while raising pre-flop.

"Sorry, what?"

Jacob replied, calling my bet. Most people at the table folded, except for Nick, who joined the fun.

"You wanna tell me that a man of the many kinks like you have never watched is girl getting fucked before?"

I replied calmly as the dealer drew a king, a five, and a three.

"Nah man, honestly, I can satisfy my girlfriend."

Everybody laughed as he started looking at me straight in the eyes. My attempt to make him mad just made me fume. Too bad, I knew I had the winning hand.

"I am not too sure about that."

I replied, betting a considerable amount of my stack.

"Oh, I see, someone woke up in a bad mood. We are just joking; no need to get worked up like that. How much do you have there? I want you all in."

I looked at him quite surprised. Lucky day for me, apparently. Nick immediately folded as I set up my trap.

"Woke up in a great mood actually. I call your all in, and I want to bet even more."

"Daring, aren't we? What do you have in mind?"

"If you win, you will get Rachel's anal virginity."

A loud uuuh came from the table.

Rachel looked at me with dead eyes.

"What the fuck are you doing?"

She whispered.

I touched her leg with my hand and looked at her with an incredibly cocky gaze.

"Chill."

"But if you win?"

Jacob continued.

"I will fuck her in the ass, and you will do with us this great cuckold kamasutra you talk so much about."

An vven louder sound came from the table. I looked at him in the eyes, smiling. I was eager to see the pressure in his eyes.

But I never saw it. On the contrary, he started laughing like crazy and snap-called.

He threw on the table a pair of kings: trips. Only an ace could have said me.

Everybody started screaming and laughing while standing up next to the croupier, who professionally went on dealing the cards.

Dead in the eyes, the world stopped around me.

A two of hearts.

A 4 of spades.

A roar around the table.

All the boys jumped on Jacob, laughing with him.

I stayed up, alone, in silence, well aware that I had just fucked up badly.

I looked right at Rachel, and she was fuming.

"My maaaan, what were you training to do??"

Jacob couldn't stop laughing, understandably so.

I wanted to reply and say something back, but I was at a loss for words. I endured minutes of roaring excitement, unable to look at Rachel. Finally, she was the one that grabbed me by the arm and took me away from the situation.

I could hear everybody screaming and laughing as I turned my back and followed her just a couple of steps away from the table.

"WHAT THE FUCK WHERE YOU THINKING ABOUT?"

"I... I had a winning hand..."

"YOU DID NOT YOU FUCKING MORON."

"But..."

"YOU HAD TO IMPRESS ME, NOT SELL MY FUCKING ASS AWAY."

"I am so sorry."

"SORRY, SORRY! YOU KNOW HOW FUCKING BIG HIS COCK IS. NOW BECAUSE OF YOU, I WILL HAVE TO TAKE IT MY ASS. YOU ABSOLUTE IDIOT."

"You... you don't really have to do it."

"Of course I have to do it. AND I WILL FUCKING TAKE IT. YOU... YOU... CAN'T YOU NOT FUCK UP FOR 5 MINUTES?"

"I... I... pair of aces... unlucky."

"GO BACK TO THE ROOM. I REALLY CAN'T STAND YOUR FACE RIGHT NOW."

I wanted to say something back. I want to earn my forgiveness, but I knew I had messed up badly. I looked back at the people at the table. They were visibly grinning, pretending not to hear what was going on, but clearly listening to every single word.

I nodded and went on my way. I couldn't stop thinking about what had just happened. I wanted to get in Jacob's head, but clearly he entered mine. I walked back, reliving the cards being shown and Jacob laughing at me.

I entered the room and layed on the bed silently. I got naked and turned on the TV. It was quite early, but I just wanted to sleep and forget. The hours passed, and both Rachel and Jacob were nowhere to be seen.

At an indefinite hour, I fell asleep, hypnotized by the meaningless content I was absorbing.

My dreams turned out the same as reality.

I saw Rachel. I saw Jacob. They were having fun with me. How little of a man I was. They started having sex; I was powerless. I turned and turned. I was losing my woman both in my dreams and in reality. They were fucking so hard. She was having such a good time, and I was so far away, looking from above. Then slowly getting closer to them. Her face is getting clear in my mind. Her spasms of pleasure are getting clearer and clearer. Finally, I was almost next to them. I could feel her hand on my chest while she was getting split open by her lover.

Wait.

I can really feel the heat on my chest.

I can really feel the moans intensifying.

"He really has a deep sleep. There is no fun in this."

I slowly opened my eyes.

Rachel was bent over naked next to me, her hand grabbing mine. Behind her, Jacob was towering.

"Here you are, cuck. I thought this could be a nice surprise for you. Also, I know this is totally cool for you."

Jacob grinned as he kept fucking Rachel.

A wave of shame mixed with excitement woke me up immediately. I looked at Jacob without really knowing what to say.

"Actually, now that you are awake, would you mind moving to the chair? I need room in this bed."

I remained silent for a couple of seconds, too confused to really understand what was going on. Rachel grabbed my arm harder as her moans intensified. Jacob was clearly putting all his effort into this performance.

I knew this was both Jacob's victory lap and Rachel's petty revenge for what had happened before. There wasn't much I could have done in that situation.

I stood up, evading Rachel's grip, and silently went my chair in the corner as instructed.

From that position, I could see only my love's feet and his lover's ass while the sounds of pleasure were filling my room. Slowly the excitement started building, and my cock began his now ordinary, but useless, fight against its metal prison. I started massaging it while silently watching the couple have fun. I couldn't help but feel different from the other times this had happened. I was used to receiving some sort of attention from either one of them; Rachel used to put on an amazing kinky show for me. Not this time. The two were absolutely focused on one another while I was left out.

For the following 30 minutes, they kept changing positions on the bed, but I never had the possibility to see either some action or Rachel's beautiful face. Only once I tried to get up to have a better view, and I was immediately scolded by Jacob, who ordered me back to my place. Rachel knew that ignoring me was the most proper and humiliating punishment given the situation. Finally, I heard my master grunting, and the action was over.

He got up and went to the bathroom, leaving the two of us alone in the room. I wanted to say something. I wanted to say sorry again, but I was not given the possibility. Rachel snapped her finger and pointed between her legs. I knew what I had to do.

I got up and silently crawled onto the bed and started my cleaning duties. As soon as I got my face closer to her creamed pussy, I noticed that her ass was filled with a pink plastic plug. While the visible part of mine was hearth-shaped, hers was pink and circular, with the sentence "BBC only" written in big, bold letters. Message received.

Absolutely defeated I started cleaning up obediently all of Jacob's cum with my tongue. I heard him coming back from the bathroom during the process. I felt him entering the bed again. I felt his strong hand pushing my head on her pussy as he started passionately kissing my love.

Finally the hand moved, and I knew I had done a satisfactory job. As soon as I looked at Rachel in the eyes, I understood that this was not nearly enough to get myself pardoned. She moved her head immediately and buried it in Jacob's neck. He, on the contrary, had a smile going from one ear to the other.

"Tough luck, cuck. You can go back to sleep, I think."

I nodded silently and went back to the angle of the bed, giving my back to the two of them. Rachel was in the middle, but hugging tightly my master's body. I could hear them cuddling and kissing for a while; sometimes her legs would touch mine for a brief moment.

That was the most attention I got before falling into a dreamless sleep, exhausted from the terrible day I had just had.

Chapter 14

The next morning I was woken up by sounds of gagging. Rachel had decided not to lose any time and wake him up with a blowjob, treatment that I had always asked and never received.

I turned my head still half asleep and saw Jacob's smiling face looking at me.

"Morning."

"Morning."

I answered a bit grumpily, my cock starting to ache immediately.

"Would you mind grabbing something for breakfast?"

"Not at all."

I got up on from the side of the bed, happy at the idea of leaving them alone for once. Rachel was making as much noise as possible while worshipping his pole, while giving me no attention at all. I knew I had to earn her forgiveness as soon as possible.

I looked at her plugged ass and resisted the urge to slap it.

I got up and exited the room completely naked without saying a word.

Taking my time, I went to the bar and grabbed coffee and croissants for everybody. I really hoped to be back home when the action was already over.

To my disapproval, upon being almost 20 minutes later I was far from correct.

Jacob was still in bed, sitting on its end, reading the newspaper, while Rachel had not left her position and was still bobbling on his huge cock.

When I opened the door, my teacher lowered the journal and smiled at me.

"Here you are; I was just wondering if you got lost."

"Sorry for being late."

I lowered my head in shame.

"No worries; I was waiting for you because I had a thought."

"About what?"

Again, Rachel started gagging loudly, making it difficult for me to hear his words.

"Yesterday night we discussed a lot and I have been thinking about the fact that I might have been too though with you. Yesterday evening you wanted to be splendid in front of everybody, and you got what you deserved, maybe even more. I hate to see my favorite couple in a fight, and I think I could fix that."

I tried to catch Rachel's sight, but she remained down, diligent on her task.

"How would you do that?"

"I can give you back what I won."

"Really?"

My hopes got up immediately.

"Yes, it is worth way more to you than it is for me. Also, training her ass for my dick would be a pain. But I want something in exchange."

My eyes got wider. That was fishy, but would solve my screw up faster than expected. I nodded.

"Come here; coffee is getting colder."

"Oh sorry."

I sat on the side of the bed and put the breakfast next to him. Then, as I watched him grab his coffee, I added:

"So, what do you want back?"

"Suck my cock."

My heart skipped a beat.

"What?"

"Get down and suck my cock until I cum. Now."

I instinctively looked down. To my horror, Rachel was finally paying me attention. My teacher's huge cock was covering half of her spit-covered face; saliva was drooling from her smiling mouth to the bedsheets. Her beautiful eyes were looking into my soul, inviting me to join her.

I looked back at Jacob, who raised his highbrows, waiting for an answer. A fair deal from his side.

A rush of excitement went through my body. Once again, I was considering reaching a new low. Was I really that pathetic? My mind started coping. It was the only way to get Rachel back. Was it though? I looked back at her; she was back at worshipping his cock, now with her eyes open, looking straight at me.

Maybe I wanted to try. I mean, it was so big, so juicy. Rachel was surely enjoying it. No. I was going to do it not for, but just to earn Rachel's forgiveness.