Read Part 1 Here
Read Part 2 Here

*****

Chapter 7

Rachel sat on the bench in front of our teacher and invited me to join her. After sitting down next to her, she hugged me tight and laid her head on my shoulder. Sex was over, and she was making clear I was the one she now wanted to cuddle with.

This actually made me feel way better. Now, I was the one looking at him with a smirk.

He didn’t seem to care too much and kept looking at the now almost over sunset while sipping on his wine. I really wanted to ask for my key, but I didn’t want to be the first one to break the silence.

Luckily, Jacob did it for me.

“Sorry, I lost my composure, I was supposed to teach you both something, but Rachel, you were too hot. I had to have you right there.”

I could see her smiling; that was her goal. The plan that she and Lucy had thought about had worked.

“Oh, no worries, I am sure Jack learned a lot.”

She gave me a soft kiss on the cheek, smiling. The comment just built on my horniness.

“I was actually very surprised by your composure, Jack. I might have gone too hard on you. Usually, this kind of humiliation is something that navigated couples ask me. You also cleaned up immediately without complaining, something I wanted to introduce you to slowly in the next few days. You are truly natural at this.”

My face turned red in embarrassment. This was truly a double-edged compliment. At that moment, my mind was just focused on saying the right things to get my key back.

“I mean… I just followed the flow. I am glad you think I did good.”

“Oh, you did very well. Chastity truly brought out your best behavior. I am starting to think we can build on that further than I initially imagined.”

I looked at him in disbelief. What had it meant? Was there more to this? What else could he possibly have to show me? He took a long sip and continued.

“Yeah, yeah, there is surely more than I thought, but let’s not jump ahead. Let’s focus on tonight. The night has just started, and I am beginning to feel hungry. What about grabbing something to eat at the main restaurant? I know there is a big party tonight we participate in all three?”

The idea honestly scared me, but Rachel’s face made me understand she was actually excited about this.

“I guess we could.”

I anticipated her.

“Great! So maybe it would be better if Rachel got her face cleaned first. There is a bathroom not too far from here. Me and Jack can wait here for you, I think it could be a great time for us to bond.”

She agreed, quickly got her clothes back on, and disappeared on the beach. I remained there, uneasy at Jacob’s presence, not really sure what he wanted to talk about with me.

I poured us some more wine, and he finally broke the silence.

“You understand that after this experience, there will be no coming back from you and Rachel, right?”

“What do you mean?”

“You two have found out too much about your desires to go back to your usual boring lives. Do you think you can keep up with that?”

“I mean, it has always worked so far…”

“She is not the same Jack. You woke up our sexual instincts. Now, you have to keep up with that. Are you sure you like this lifestyle? Because I bet she will keep asking for bulls from now on.”

“I mean, I like it, she likes it. I think we can try this out. Not gonna lie. This had been the most erotic 24 hours of my life. The only thing is that this chastity is starting to be bothering me…”

A huge smile covered faces.

“So you are seriously into this, uh? Incredible. Still, you understand if you get out of the cage all these sensations you are feeling will disappear. All this truth you are speaking will go away. Do you want to trash everything you have done today?”

“Yes, but…”

“Listen, there is another way to get pleasure. A lot of cucks love it, and I am sure you could be one of them.”

I knew what he was talking about, but no way I could do that in front of Rachel.

“Anal pleasure is the best way to achieve what you want. I think you should explore it. I have seen people cumming from anal only and telling me that was the best orgasm of their lives.”

I looked at him, bothered. His eyes pierced through me unbothered.

“You do you, but be well aware that I have no intention of releasing you until the end of the training week.”

“Wait, you said…”

“I said I was going to do the best for you and trust me, this is the best choice.”

I felt patronized. I wanted to scream but I knew it would have been useless. I was the only cause of this.

After this, he forced me to change the subject and I forgot any chance to get freed anytime soon. For the following 30 minutes, we talked about our lives and football. We actually got along pretty well, and Jacob proved once again that, when not horny, he was an incredibly delightful person to talk with. We were in the middle of the heated debate on who was going to win the title this season when Rachel finally got back with a brand new make-up.

We both got up and decided to head for dinner.

We reached the restaurant after an uneventful walk, and there we met Lucy with his partner Nick. He was a very skinny, tall guy with dark hair and eyes and very pale skin. I could see this kind of guy spending his days on a computer in a dark room, he truly had the nerd vibe, but he had a quite handsome face and, of course, a huge dick. He was wearing a white shirt with rolled-up sleeves and a series of bracelets on both arms. Lucy, on the other side, had fulfilled her promise of a very daring dress and was looking truly gorgeous: she was wearing a very short white skirt, which was constantly showing half of her ass and her white panties, while her boobs were only “covered” by a semi-transparent strip of tissue tied around her chest not larger than 3 cm. By my inevitable look at her breasts, I also noticed her pierced nipples, which only added a kinkiness to her outfit.

After everybody had introduced themselves, the two girls convinced everybody to sit at the same table and eat together. I was not too excited by the idea, but in that moment I was not in the situation to have my voice heard. Rachel sat in front of Jacob and next to Lucy while I got the seat at the head of the table between the two of them.

“So, you actually got the outfit we agreed on! You look absolutely splendid! I hope it got the effect you were hoping for.”

Lucy started immediately teasing Rachel.

“Of course! Do you think it looks good?”

“It looks gorgeous on you! I bet the boys agree.”

We both nodded, and Jacob added, chuckling:

“It sure affected me!”

Rachel chuckled while I turned red in shame. Nick also nodded and smiled innocently.

“Lucy told me about your shopping expedition. I am so glad you came up with… this. Also, thank you, Jack, for helping. She told me how valuable your input was regarding how to work us up.”

“Oh well… you are welcome, I guess. I didn’t do much, to be honest.”

“Don’t be humble. You took one for the team! I was a bit jealous when she told me about your encounter, but when I realized your situation, I felt very thankful. You really have a gift; you should do it more often!”

Jacob laughed from the side.

“You are absolutely right; he truly has great fashion taste. Maybe I should step up and make you choose all the outfits for the next days.”

“Oh guys, you are so bad, especially you, Jacob. Aren’t you teasing him enough already?”

Lucy intervened in my defense.

“He subscribed to these classes. I am just trying to get the most out of this week. You should have seen the guy. He is truly a natural cuck. I would go crazy with just a minute in a chastity device. He has been there for over 24 hours now, and look how calm he is. These are exactly the kind of exercises he needs to prove his self-control. Am I right, Cucky?”

“Well… yes. I have to say so far, he has done everything to show me and my love the best practices to follow for this lifestyle.”

Everybody at the table was surprised by the answer. Probably nobody was expecting such a level of submissiveness, myself included. The reality was that the subtle threat of a week in chastity was making me behave quite well. Lucy was the first one to break the silence.

“Oh wow, you guys are so lucky. I wish I had someone like him, I guess he might become quite handy. Are you training him to become a servant?”

“Oh no, it is not in my interest to shape him in any specific way. I am just trying to get out what’s already inside of him. I must say he is very predisposed to that realm; in just a couple of days, you can see how submissive he has become. We have five more. Who knows what else can come out of him.”

He smirked at me and then, to my pleasure, changed the topic to more mundane things. We spent the rest of the dinner talking about our lives inside and outside the island. Nick and Lucy told us about the crazy orgies they participated in and how they were very proud to have fucked almost everyone on the island so far. They tried to convince me to have a swap with them, but luckily for me, Jacob got me out of the trouble by underlining how we were not allowed to do any kind of swinging before the end of the week. Apart from this little moment of tension, the rest of the dinner was quite pleasant. We found out that both our new friends were working in Banking in Italy and, like most people on the islands, were regulars on the resort.

After finishing to eat they made clear that they were going to the daily “party” at the pool in the middle of the island.

I looked at Rachel, trying to understand what her intentions were, but she was too focused on Jacob to answer me, so much so that I had to speak up.

“So, do you want to go to the party?”

“Yep! Sounds fun, doesn’t it?”

“I am not sure about that…”

“Nobody is forcing you to come.”

Jacob intervened.

“Actually, it might be better for you to go back home. You cannot always be around your girl, you know.”

I looked at Rachel with puppy eyes, but from her face, I could see she was agreeing.

“You have never been a party guy, Jackie. Jacob has a point here. Just go home while me and the others have fun, no need to push yourself on this.”

“I will keep an eye on her, no worries! I will not allow her to fuck anybody else than Jacob, ahah.”

Lucy intervened, but I did not doubt that her ‘eyes’ were going to do much.

“Go home, cuck, come on, you lady is in safe hands.”

Jacob sealed the deal. He looked at me straight in the eyes and grabbed one of her boobs while indicating the way home with the other hand.

Absolutely defeated, I got up and said goodbye while more wine arrived at the table. From the path home, I could hear all of them chanting and laughing, and the humiliation was building up in the silence of my walk.

I arrived home alone and realized I had nothing to do. The constant thought of what Rachel was doing was killing me. At the same time, the lust and denial I had built up in the past hours were torturing me.

Involuntarily I did the only thing that made sense to me at that point: I turned on the tv and started watching porn. I went straight to BBC porn and began touching my caged dick while watching gorgeous girls getting drilled by huge dicks. Of course, this just built on my excitement, which was now out of the roof.

After more than 20 mins of porn and denial, an idea struck me. I opened Rachel’s bag, and there I found a multitude of sex toys. I immediately went for the one that suited my needs the most: a small transparent dildo. I got myself in front of the tv, opened my legs, and, almost automatically, proceeded to lube the dildo and put it in my ass. It was my first time, and I had never tried to train my hole before.

A sharp pain hit me and woke me up from the dream state I was in.

What the hell was I doing? How painful is this? How can girls like this so much?

These questions and more started filling my head. But slowly, the pain started to fade, and the moans of the girls on TV became louder than my thoughts.

I put myself in the pose again and repeated the process. This time, slowly, more carefully. I immersed myself in what was happening in front of me. The result was completely different. I low sense of pleasure appeared near my hole. I explored it more deeply; it was new, and I liked it. Slowly, I inserted more and more of the dildo inside me, and the more it was in, the more pleasure I felt. It was an incredible sensation of fullness. I, like the blonde bombshell on TV, was learning to enjoy getting filled. I started moving it slowly, in and out. Then, a bit faster. Soon I was properly fucking myself in front of the tv.

It was not like masturbating, at least not like I was used to, but it was giving the pleasure I was so much seeking. I lost myself in the pure sense of lust this new situation was giving me, fucking myself harder and harder in front of porn, increasingly kinkier, trying to build an orgasm from my ass. Going further with each video and closer with each trust.

I cannot say how long this state lasted. What I know is that it was interrupted by someone opening the door.

*****

Chapter 8

Rachel opened the door and looked at me completely still for a couple of seconds before she started laughing hard. I could tell she was drunk.

His reaction was understandable, considering she just had caught her husband on all fours with a dildo in his ass looking at BBC porn.

“OH… MY… GOD…”

Her tone was a mix of shock and amusement.

“I… I can explain.”

“YES, PLEASE, explain to me how this is not how it seems.”

“…”

“Jacob told me, but I was stubborn. Less than 48 hours in chastity, and you are already with something in your ass? Truly pathetic.”

With every word she was saying, she was taking a step toward me.

“No wonder you couldn’t satisfy me. You were always thinking about someone fucking you, eh?”

She was now in front of me and grabbed my face with her hand. She was getting angry, I wasn’t sure why. Maybe she felt betrayed. Maybe it was the alcohol talking.

“Thank God we have met Jacob. He will be able to take care of us both. He just took care of me you know? While you were here gooning on your own, he fucked me soooo good. I bet you are jealous but of him or me?”

I was speechless. A tornado of emotions was hitting me all at once. I was sitting on my bed, my ass still filled, and an angry, drunk girlfriend in front of me. I need to get the situation back to normal, as much as it was possible, at least.

“Love, of course, I am not jealous. You know we are here just to feel you good.

Relax, let’s talk about this. Everything is alright.”

She paused her overtalking and her face got more relaxed. She sure wasn’t expecting such a calm response from my side. She pressed her forehead against mine, and I could smell the scent of alcohol.

“You always know the right thing to say. Sorry, maybe I overreacted. It’s just that I am so drunk, and you were so funny in that position. And Lina was such a bitch.”

“Who is Lina?”

“The bitch we met the first day.”

“Ah.”

“She was such a bitch.”

“You already said that.”

“But it is true. She tried to fuck Jacob. In front of me. I am not a fucking cuck. Bitch behave.”

“Ouch.”

“Ah, come on, can I have some support at least from you?”

“I mean, yeah.”

“I also got a gift from you. I came home just to give it to you.”

“What is that.”

She got closer to my ear and whispered:

“I have Daddy’s cum leaking from my pussy. Do you want to slurp it up while I tell you my night?”

The question made all my body shiver in excitement. I couldn’t lie about how much this kind of process excited me in the past and how badly I wanted to feel those sensations again.

I laid on the bed, with the dildo still halfway into my ass, and she climbed on my face. The base of her dress was ripped open, and the g-string was missing. On the other hand, the area was sticky.

As soon as her pussy was within reach, I immediately started licking up the sperm left by Jacob without asking any questions.

She put both of her hands on my chest and slowly started grinding on my face while moaning softly.

She touched my cage softly with a giggle before starting her story.

“So, after you left, we started drinking. You know I usually don’t like this kind of stuff, but Lucy insisted so much I gave up. We stayed at the table for a while, and, oh boy, I have no idea how much we drank together. A lot for sure, though.”

She started grinding a bit faster, carried by the story.

“Anyway, we got up and went dancing. I have no idea where it was, but so many people were there… and the music was so loud… and everybody was dancing… and everybody was having sex… and you know how much I get horny when I get drunk.”

She was now grinding even harder on my face as I was searching for the last traces of sperm.

“So we got in the middle of the floor, and we started dancing. He was all over me, and I let him do whatever he wanted. I was grinding on his dick, and I felt it getting hard. I teased him so much that at some point, he got crazy and ripped off my dress and started fucking me from behind in front of everyone.”

I could feel my cock aching against the device. I was so horny I couldn’t think. I lowered my hand and started thrusting the dildo inside me once again as she was speaking.

“It was so hot. I was there doggy-style, getting drilled in front of everyone. Lina was having sex as well next to me… that bitch.”

She slowed down on her grinding.

“The audacity to ask me to swap partners. Jacob’s dick was way better than Dan’s, I could tell from a mile. But I showed her.”

I felt her hand reaching mine and grabbing the dildo in my place.

“I turned back and asked Jacob to pick me. It was sooo good. I was up there… and he was there drilling me… so hot… and you were here… with your little toy…”

She lowered her back and started grinding on my face harder as she was fucking my ass with the dildo at an increased pace. Suddenly I also felt her tongue on my penis. I was in absolute ecstasy, and I could tell she was as well. I started feeling an orgasm building up from my ass. A new sensation building up from my prostate was expanding on my body. I was inches away from my first anal orgasm.

A huge moan came from Rachel’s mouth. She grabbed my body tighter and stopped stroking. I licked harder and harder. She orgasmed on top of me while I came short of my much-needed relief.

As soon as she stopped shaking, she climbed down off my face, kissed me on the lips, and hugged me under my right arm. She fell to sleep almost immediately, leaving me next to her, pacified but not fully satisfied.

*****

Chapter 9

I woke the following morning feeling incredibly tired with pain coming from my crotch.

My caged penis was not appreciating the lack of relief, and this morning’s boner was only accentuating this.

More importantly, Rachel was nowhere to be found. Considering that it was almost lunchtime, I assumed she must have gone out before me. I wouldn’t say I liked this lack of communication, especially after what had happened the night before.

I took a quick shower, put on a white shirt, and immediately left the room looking for her.

The search was not long as I immediately found her chatting with Jacob at what had now become our usual table.

As soon as they saw me, they both waved their hand and asked me to sit down.

Before I could say anything, our teacher started talking:

“Jack, I must give you my apologies.”

“Why is that? I mean…”

“Yesterday evening was completely unprofessional from my side, Rachel told me what happened with the two of you, and I now realize I got carried away and asked too much of you. The booze and the excitement went to my head. I hope you can forgive me.”

I looked at Rachel, who avoided my eye contact while staring at the floor. On one side, I was mad she had gone talking with Jacob this way, but on the other, I was relieved that this was the outcome.

“Before you say anything. I want to stress again my deepest apologies. Take a step back and resume your training in a more controlled way. Can you accept that?”

“I… Yes, I think that could work.”

“You are too kind, Jack, but I promise your trust will not be misplaced. First of all, I would like to set up a safe word. We never did that. What about Uzbekistan?”

“Good for me.”

“Good for me as well.”

“Second of all, I gave your key back to Rachel. She will keep it until you ask her on your own to give it back to me if it ever happens. Said that, I am sure you two have much to talk about, and I don’t want to be in your way. I will see you two tomorrow morning.”

He got up, smiled brightly, and left the two of us at our table without saying another word.

An awkward silence fell between us. Rachel was the first one to break it.

“I am so sorry about everything… about yesterday night… about this morning…”

“Woah, relax, everything is alright.”

“I just woke up and felt so bad about it. I didn’t know what to do…”

“Hey, it’s okay, for real… I am not mad, but there is much we got to talk about.”

I grabbed her hand.

There, slowly, we started decompressing. She excused herself so much for the behavior of the previous night, during the party, and after. She attributed everything to the alcohol and sort of believed it. I made sure to let her understand that this was part of the experience, and despite I had felt humiliated, or at least would have if I wasn’t so horny, I was not mad at anybody.

It was almost 3 pm when we came back to our room, relieved from the big conversation. Up until then, we hadn’t still talked about what had happened when she came back.

“So you like anal sex?”

The question came unexpectedly and left me baffled.

“Well, I mean, a bit…”

“It is fine for me, you know. Many men do like it. I just want to understand if you did that only because you were so desperate for your chastity.”

“Yes and no. Surely, that drove me there, but I cannot lie. I enjoyed it quite a lot.”

“Everything?”

“Everything”

As I said that, my cock tried once again to get hard, causing me to try to touch it automatically.

“Oh, poor thing, this must be becoming unbearable. Here, let me get out of it.”

She immediately took the key and freed me for the first time in more than 48 hours.

My cock immediately got hard.

“It must have suffered so much these past few days. I think you truly deserve a reward. Ask, and it will be given to you.”

As she was saying that, she opened her legs and exposed her pussy to me.

I was so horny I could think. Immediately jumped on her, kissing her neck. My cock slid in her pussy effortlessly, probably due to it being now used to bigger things, and I started fucking her furiously in the missionary position.

In this state of mind, I could have normally lasted no more than a couple of minutes, but she decided to make it even shorter.

As soon as I started trusting in her, she smacked my ass hard with one hand while the other went straight for my asshole, playing with it.

It was too much. After four pumps, I exploded in her with an orgasm of unprecedented intensity.

I fell on the side, finally enjoying my head clarity and well-earned orgasm as Rachel went to the bathroom to clean herself.

When she came out, she had a smirk on her face.

“So you do like anal stimulation! I feel way less guilty about yesterday night, to be honest.”

“I mean… a bit…”

“You know, I will be more than willing to explore this more. Jacob gave me a strap-on, just in case. I have always wanted to try it.”

My eyes were full of shame, and my head was saying no, but my cock got immediately hard again, exposing my true preference.

She got closer to me. She was standing as I was sitting on the bed next to her. She started caressing my head.

“Would you like to try? Feel a big dick in your ass? Understand how does it feel to get fucked.”

I gulped, I was getting once again horny as hell.

“I… I am not against it.”

“You are not against it, eh? Naughty boy. We will see if you are not against it.”

She gave me a passionate kiss and moved to her luggage. From the pile of sex toys, a big strap-on emerged. It was not there the previous night. It was slightly more than 16 cm, bigger than me but far from the sizes I had seen this past few days.

She came back to me, the dildo the same height as my eyes.

“Wanna try it now?”

I nodded silently.

She grabbed a tube of lube and put it on the bed next to me. She got over me and started kissing me passionately, her hand rubbing all over my body and the plastic dick pressing over mine.

Suddenly, I heard a squirt. Her lubed hands got near my hole and started lubing it. I softly moaned without moving my mouth from hers.

One cold finger entered me. I felt my dick getting harder. Slowly, she started fingering me, first with one, then with two fingers. I tried with all my willpower not to moan, but a couple escaped my mouth.

After minutes of foreplay, I was in heaven. One hand tried to reach my cock but was blocked by her.

“Let me take care of this.”

She whispered.

She got up, lubed her dildo, and slowly inserted it into me.

As I felt my ass getting spread open once again, the sight in front of me was out of my wildest dream. I was stomach up, legs spread open in the air, The huge boobs Rachel slowly bouncing as she was slowly working her way in.

She grabbed my cock and started to stroke slowly. I was in paradise.

I rolled my eyes back and enjoyed every single second. I don’t know how long it lasted. It was slow, soft, romantic. Every couple of minutes, she would stop stroking my dick to come down to me and kiss me as my orgasm was building slowly. Every time my penis would start twitching, she would start caressing my hair or my stomach. I was a tea, but a blissful one. After almost 30 minutes of pegging, she released me. She started stroking and fucking me faster, and I soon exploded on my stomach in orgasm as intense as the previous one, if not more.

That was the first time I was fucked.

To Be Continued…?

 

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