Resort Sizing Up: Pt. 3
Apologies for the delay and shorter follow-up. I became stuck and needed inspiration to carry on. Your reviews and input are invaluable in fueling my creativity. If you have any suggestions or feedback, please don't hold back.
Chapter 7
Rachel settled onto a bench beside our instructor, inviting me to sit down beside her. Once I had joined her, she wrapped her arms around me and nestled her head on my shoulder. This signified that she now wanted affection from me.
This was quite relaxing for me, instead of feeling humiliated, I found satisfaction in now being the one eying him with defiance.
He seemed uninterested, gazing out toward the nearly set sun while finishing his glass of wine. I felt the need to ask for my key, but didn't want to be the first to break the silence.
Luckily, Jacob intervened.
"Apologies for my behavior, I was supposed to instruct both of you, but Rachel... she was so seductive. I couldn't resist."
I noticed the smile on her face; it was her strategic move in collaboration with Lucy.
"Nothing to apologize for, in fact, it just spiced things up a bit."
She gave me a peck on the cheek and smiled. This stoked my libido further.
"I was actually quite surprised by your reaction. Usually, this kind of humiliation is something couples come to me to arrange. You, Jack, handled it well. You promptly cleaned up afterwards with nary a complaint. You seem to be natural at this."
My face flushed from embarrassment. I was flattered by hisdouble-edged compliment.
"Just following the flow. Glad you thought I performed well."
"Very well, indeed. I've been contemplating the potential for more with you. The chastity seems to have shaped your behavior. I'm starting to think we can progress even more."
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I smirked curiously. What else could he possibly teach me?
"Let's not jump the gun. For now, let's focus on the evening ahead."
I hesitated, as participating in the party terrified me. Seeing her excitement, however, reassured me.
"We could."
I anticipated Rachel.
"Great! Since Rachel needs to clean herself up first, why don't you enjoy the sunset and have a sip of wine with me? I know there's a major party tonight we'll all attend."
She accepted, dashed off to change her clothes, and disappeared down the beach. I remained, apprehensive about Jacob's intentions.
I obliged, poured us more wine, and he ended the deafening silence.
"After today's experience, there's no turning back for you and Rachel."
"How do you mean?"
"You've discovered your hidden desires. Stamping your previous humdrum lives would be difficult."
"But it's always worked so far..."
"But she's not the same Rachel. You've awakened her appetite. I suspect she'll demand more bulls from now on."
"I like it, she likes it. We can experiment more."
His face lit up.
"There's another way to gratify yourself if the chastity causes discomfort. Many cuckolded men enjoy anal pleasure. I advise you explore that. Many men claim to have the orgasm of their lives from anal-only sex."
I sighed in response, already knowing what he was implying but couldn't do it with Rachel present.
"And if you free yourself from that cage, all these feelings will vanish, as will your candor."
"What if I don't want to abandon this experience?"
"Trust me, this is in your best interest."
The patronizing remark frustrated me. I wanted to argue, but realized I was the root of this predicament. With a sigh, I acknowledged my mistake.
"Fine, I trust you."
Jacob grinned.
"It's vital you understand that I have no intention of releasing you before the week's training is complete."
"Wait, you said..."
"I promised I'd do what's best for you, and trust me, this is it."
I felt deflated. I longed to scream back, but I realized it would have been futile. It was my blunders that resulted in this predicament.
There's a 50/50 chance that he continues practicing celibacy or expresses eagerness to try anal stimulation with his partner. Regardless, the instructor tells him to remain chaste the entire training week.User 0: In case you're wondering how to make demand for change, the thing to remember is everybody's life and progress takes different time and challange. Some people take a mob to the street, some people make a revolution without literally changing place. There's the 50-50 percent on choices made for a reason. What about you? What would you rather chose and why?User 1: In this specific situation, I'd choose the experience of ramming my dick into his adorable ass rather than trying to break my chastity. We can all be free, but at least some of us enjoy living a life in captivity.User 0: You can also make rules for your soulitions but only if you communicate with people, their boundaries could be similar. Although i like the idea of making people experience what it feels like to not live on their own best, that's a point. If not for pain, then for pleasure.User 1: It might be difficult, knowing how hard it can be to respect people's choices. I know I'd probably struggle to tell someone they can or can't have sex (cries), but I get that it's for their own good. In the end, as long as consent is the focus, then no one should have any complaints.User 0: I don't think it ever was about not scoring or getting naked. It's like learning to do it in a group or watching someone doing something they enjoy around you. He's not the first one that found enjoyment in it, i guess. I am super curious on how far people will go for a challenge, i glad he found out something new. We can justify it anyhow if that's the engery that excites you the most. The bottomline is to know what you wantUser 1: I agree, it's not about the act of sex itself but seeing others do it or trying it myself to see what it's like. It's a new experience and one to be a lot more respectful for. In the end, as long as full consent and respect is maintained, then we can't really go wrong
After that, he made me switch the subject and I forgot about any chance of being liberated anytime soon. For the following half an hour, we engaged in a conversation about our lives and football. We actually got along quite well and Jacob displayed once again that when he wasn't aroused, he was an incredibly enjoyable person to engage in conversation with. We were in the midst of a passionate back and forth over who would win the title this season when Rachel returned with a brand-new makeup.
We both got up and decided to head to dinner.
We arrived at the restaurant after an uneventful stroll and there we spotted Lucy with her partner Nick. He was a slender, tall man, with dark hair and eyes and very pale skin. I could envision this type of man spending his days in front of a computer in a dark room, he indeed had the nerd vibe about him, but he had a quite attractive face and, of course, a massive dick. He was sporting a white shirt with rolled-up sleeves and a collection of bracelets on both arms. Lucy, on the other hand, had followed through with her promise of a daring dress and was looking exceptionally stunning: she was sporting a very short white skirt, which was frequently revealing half of her ass and her white panties, while her breasts were only "covered" by a semi-transparent strip of cloth that was tied around her chest no larger than 3 cm. By unintentionally gazing at her breasts, I also noticed her pierced nipples, which only added to the kinkiness of her appearance.
After everyone had introduced themselves, the two women persuaded everyone to share a table and eat together. I wasn't too thrilled by the concept, but at that point, I wasn't in a position to voice my opinion. Rachel took the seat in front of Jacob and beside Lucy while I claimed the seat at the head of the table between the two of them.
"So, you managed to get the outfit we agreed on! You appear wonderfully attractive. I hope it had the intended effect."
Lucy began ribbing Rachel immediately.
"Of course! Do you think it looks attractive?"
"It looks incredible on you! I'm sure the boys agree."
We both nodded and Jacob added, chuckling, "It definitely had an effect on me!"
Rachel laughed while I blushed with embarrassment. Nick also nodded and smiled innocently.
"Lucy filled me in on your shopping expedition. I'm so delighted you came up with... this. Also, thank you, Jacob, for assisting, she informed me of its significance in arousing us."
"Oh okay... you're welcome, I suppose. I didn't really do much, to be honest."
"Don't be shameful. You stepped up and helped. I was slightly envious when she informed me of your encounter, but once I considered your circumstances, I felt quite appreciative. You truly possess a talent; you should put it to use more often!"
Jacob chuckled.
"You're absolutely correct; he indeed has great fashion sense. Perhaps I should assume the role of deciding your outfits for the next few days."
"Oh sirs, you're terrible. Don't you tease him enough already?"
Lucy stepped in to defend me.
"He signed up for these lessons. I'm attempting to gain the most from this week. You should have seen the guy; he's naturally a cuck. He's been in that device for over 24 hours now and he remains so tranquil. These are exactly the exercises he needs to show off his self-control. Am I right, Cucky?"
"Well... yes. I must admit that so far he has done everything to demonstrate to me and my companion the best practices for this lifestyle."
Everyone at the table was rattled by the comment, likely not expecting such a submissive nature, even including me. The truth was that the potential threat of a week in chastity had caused me to be remarkably well-behaved. Lucy was the first one to break the silence.
"Oh my goodness, you guys are so fortunate. I wish I had someone like him. He might prove quite useful."
"No, it's not in my interest to mold him into a specific shape. I'm simply trying to coax out what's already there. I must say he has become stunningly submissive. In only a few days, you can see how subjugated he's become. We have five more days, who knows what else will surface from him."
He smirked at me and then, luckily for me, changed the topic to more mundane matters. We spent the remainder of dinner discussing our lives inside and outside the island. Nick and Lucy divulged stories about the wild orgies they participated in and how they considered themselves extremely proud to have had intercourse with almost everyone on the island. They attempted to persuade me into a sex swap with them, but fortunately for me, Jacob talked me out of it by emphasizing how we couldn't engage in swinging until the end of the week. The rest of the evening, aside from a small tense moment, was rather enjoyable. We found out that both our new allies were employed in Banking in Italy and, like most residents of the isles, were regulars at the resort.
I glanced at Rachel, attempting to decipher her motives, but her single-minded focus on Jacob left me baffled. I had to speak up.
"So, are you planning to attend the party?"
"Oh, yes! It sounds like fun, doesn't it?"
"I'm not entirely convinced."
"No one's forcing you."
Jacob stepped in.
"Perhaps you should return home, Rachel. You can't just be around her all the time you know."
I glanced at Rachel, hoping to persuade her, but her expression suggested she was in agreement.
"You've never enjoyed parties, Jackie. Jacob has a point there. Why don't you just go home and let us have our fun?"
"I'll keep an eye on her," I said, attempting to assuage her concerns. "I'll never allow her to be with anyone but you, Jacob."
Lucy interjected.
"Go home, cuck. Your lady is in good hands."
Jacob nodded, then commanded, "Let's make sure of it." He glared at me, gripping one of Rachel's breasts while gesturing towards home.
Subdued, I grudgingly got up and bid farewell, as they continued celebrating, their laughter reverberating in the background. My journey home was accompanied by a steady stream of shouts and teasing.
Arriving at our home, I was struck by my empty house. I had nothing to do, and the escalating anxiety of what Rachel was doing weighed heavily on my mind. Concurrently, my desperation and repressed sexual tensions were gnawing at me.
In an attempt to quell these feelings, I turned on the television, navigated to a porn channel, and began rubbing myself through my underwear. However, watching women engulfed by huge phalluses only inflamed my cravings.
The thought of Rachel and Jacob across the street at the party consumed me. I leapt to my feet and sought out Rachel's purse, promptly discovering numerous sex toys within. My eyes lingered on a tiny clear dildo that caught my attention. I inspected it intently, then went to the bathroom to prepare.
Once ready, I kneeled before the TV, my legs apart, and inserted the dildo into my rear end. I now recognized the pain and discomfort, with accompanying thoughts of disdain for women who enjoyed anal sex. However, the moans from the porn stars grew louder, gradually dominating my apprehensive ruminations.
I contorted my body, aware of painful stretches and tightness, followed by a growing sense of ease, pleasure, and satisfaction. Unable to comprehend how Rachel could endure this, I persisted, hoping to understand. As I continued, a newfound joy invaded my consciousness. The dildo's entrance and removal eventually transcended my mind, with my focus shifting to the scenes on screen, mimicking the ladies therein. Determined to reach climax through this unconventional method, I pushed myself harder, faster, until ultimately reaching a scintillating orgasm.
After completing this unusual encounter, I had no way of discerning how long it lasted.
Chapter 8
Rachel reentered the house stumbling, red-eyed, and hiccupping. Finally, after a considerable delay, I confronted her with a calm demeanor.
"So... you're back?"
Laughter erupted from her as she pulled herself together.
"Oh... My... Goodness..."
As I stood, she studied my face for a moment before bursting into gut-wrenching laughter. The accusations projected in her voice confirmed my suspicions.
"I... I can explain."
"Explain how it doesn't look like you're fucking a dildo in front of TV?"
My eyes wandered between the shattered pieces of my shattered life.
"... I... I was preparing for when you returned."
"When I returned," she snorted. "You were clearly preparing for your friend."
Increasingly furious and drunk, she stormed towards me, her fingers digging into my cheeks.
"So you think it's so great to fuck yourself in front of porn? Do you envy her?"
Her anger was palpable, unclear if it was fueled by alcohol or betrayal.
"Thank goodness for Jacob. He's going to satisfy both of us."
She continued to glare at me, seemingly amused by her statement.
"I'll make sure of it," she sneered.
A note from the author:
In this story, the narrator is a cuck who spies on Rachel and Jacob while they have sex. He becomes sexually aroused and decides to try dildos, so he prepares by watching porn and inserting one in front of the TV. When Rachel arrives home, she discovers him and mocks his behavior, driving his dejection further.
I was left speechless, a whirlwind of emotions swarmed me all at once. I sat on my bed, my buttocks still full and an enraged, tipsy partner in front of me. I needed to stabilize the situation, as much as possible, at least.
"Honey, I'm not jealous, you know we're here just to make you feel good."
She paused her incessant chattering and her face calmed down. She clearly didn't anticipate such a calm response from my side. She pressed her head against mine and I could smell her boozy aroma.
"You always know what to say. I'm sorry, I might've overreacted. I'm just really drunk, and you were so amusing in that position. And Lina was quite the bitch."
"Who's Lina?"
"The bitch we met the first day."
"Ah, I see."
"She was such a bitch."
"Ultimately, yes."
"But it's true, though. She tried to sleep with Jacob. In front of me. I'm not a fucking cuck. Behave, bitch."
"Ouch."
"Oh come on, can I even get some support from you?"
"Of course."
"I also got a gift for you," she whispered into my ear.
"What's that?"
She moved closer to my ear and said:
"I have my father's ejaculate leaking from my vagina, do you want to lick it up while I tell you my evening?"
The query sent shivers throughout my body. I couldn't deny how enticing this process had been in the past or how eager I was to feel these sensations again.
I lay down on the bed, with the dildo still partway up my anus, and she straddled my face. The hem of her dress was ripped open, and the thong was missing, but the area was sticky.
As soon as her vulva was within reach, I immediately began licking up the semen Jacob had left without asking any questions.
She placed both her hands on my chest and gradually started to move back and forth on my face while moaning lightly.
She trailed her fingers on my cage with a laugh before starting her story.
"So, after you left, we started drinking. I normally don't like this sort of thing, but Lucy insisted so insistently that I eventually gave in. We sat at the table for a while, and, boy, I have no idea how much we drank altogether."
She began dancing more swiftly, carried by the narrative.
"Anyway, we left the table and went to dance. I'm not sure where we went, but it was crowded. The music was loud ... Everyone was dancing ... and everybody was having sex ... and you know how horny I get when I'm drunk."
She began grinding more feverishly on my face as I probed for the last traces of semen.
"So we started dancing together and he was all over me, and I let him do whatever he wanted. I was grinding on his dick and felt it stiffen. I teased him so much he completely lost control and broke the zipper on my dress while he was behind me fucking me in the middle of the dance floor."
I sensed my cock yearning against the device. I was so horny I couldn't think. I lowered my hand and began thrusting the dildo into my anus once again as she was speaking.
"It was so steamy, I was there on all fours getting fucked right in front of everyone. Lina was mating alongside me ... that bitch."
She slowed her dancing.
"The audacity to ask me to exchange lovers. Jacob's cock was way better than Dan's. I could tell just by observing him. But I made that bitch pay."
I felt her hand seizing mine, grabbing the dildo and thrusting it in my place.
"I turned to face Jacob and asked him to choose me. It was so scorchingly hot. I was on my back and he was behind me, pounding me ... so hot ... and you were here ... with your little device."
She ceased her dancing and began grinding on my face harder as she masturbated my anus at a more rapid pace. Suddenly, I also felt her tongue on my penis. My ecstasy was at its peak, and I could sense she was in the same state. I started feeling an orgasm brewing in my anal cavity. A new sensation building within my prostate was pervading in my body. I was on the cusp of my long-awaited anal orgasm.
A loud groan escaped from Rachel's lips, she squeezed me tightly, and then stopped moving, permitting me to catch my breath, still not fully satiated.
In the morning, I woke, feeling exhausted and experiencing soreness in my groin.
My imprisoned penis was underappreciating the lack of satisfaction; this morning's erection accentuated its distress.
What's even more upsetting was Rachel's absence. Considering it was almost suppertime, I guessed she must have left the house before me. I didn't like the lack of communication, particularly after what had occurred the night before.
I hopped in the shower, donned a white tee-shirt, and searched for her.
It didn't take long for me to locate her chatting with Jacob at the table we always convened at.
Both of them waved and invited me to sit down.
Before I could even speak, our teacher began talking:
"Jacob, I have to apologize."
"Why is that? I'm wondering..."
"Yesterday's evening was completely unprofessional from my side. Rachel informed me of what transpired between the two of you and I've realized I got carried away, prompting me to ask too much of you. The booze and excitement got the best of me, I hope you can forgive me."
I glanced at Rachel, whose gaze was fixed on the floor as she avoided eye contact. Simultaneously, I felt both angered that she spoke with Jacob in such a manner and relieved at the outcome.
"Before you say anything. I want to reiterate my deepest apologies. Please take a step back and continue your training in a more moderated fashion. Will you accept it?"
"Yes... I suppose that could work."
"You're too kind, Jacob, but I promise your trust will not be betrayed. First and foremost, I'd like to establish a safe word. What about Uzbekistan?"
"Sounds good for me."
"And me."
"I just want to clarify, I gave the key back to Rachel. She'll keep it until you indicate it's time for her to return it to me. Given your current situation, I'm sure there's much you two need to talk about, so I won't intrude. I'll see you two in the morning."
With that, he stood up and left without uttering another word, leaving us alone at our table.
An eerie silence ensued, with Rachel being the first to break it.
"I'm incredibly sorry about everything... about last night... about this morning..."
"Relax, it's all good. I'm not angry, but there's a lot we need to discuss."
I took hold of her hand.
Gradually, we began working through the situation. Rachel apologized profusely for her behavior during the party and after, attributing it mostly to the alcohol. Convinced to make her understand that I wasn't upset, I explained that it wouldn't have been an issue had I not been so aroused.
We returned to our room at about 3 p.m., relieved to have completed the exhaustive conversation. Up until that time, we hadn't negotiated what had transpired since she returned.
"So, do you like anal sex?"
The query took me off guard and left me perplexed.
"Well, kind of..."
"Men often enjoy it, so it's understandable. I'm simply trying to comprehend if you did it just because you were craving your chastity."
"To some extent, I guess. However, I can't say it wasn't enjoyable."
"Everything?"
"Yes, everything."
Upon hearing my response, my cock instinctively attempted to regain its former erection.
"Sit back. This must be unbearable. Here, let me relieve you of it."
She promptly took the key and removed the cage for the first time in more than 48 hours.
My cock grew hard.
"You truly deserve a reward. Ask, and you shall receive."
As she spoke, she straddled me, exposing her pussy.
My libido was overwhelming, and I could hardly think logically. I immediately kissed her neck and plunged into her pussy, fucking her vigorously in missionary position.
In my lust-induced mentality, my stamina was typically limited to only a few minutes, but she decided to reduce it further.
As I began to believe in her, she forcefully struck my backside with one hand while the other pushed into my anus.
It was too extreme. Just four strokes later, I climaxed forcefully within her.
I collapsed onto the bed, savoring both my clarity of mind and the pleasurable orgasm. Rachel emerged from the bathroom grinning, making a joking remark.
"So, you do appreciate anal stimulation, huh? I now feel less guilty about last night, if I might say so."
"Kind of..."
"Interesting. Believe it or not, I'd be interested in exploring this further. Jacob gifted me a strap-on especially for me," she purred, arousing me anew.
Her fingers toyed with my hair as she stood next to me.
"Do you want to try? Feel what it's like to be fucked from behind?"
I swallowed hard, feeling excited and confused.
"I'm... not against it."
"You're not against it? Naughty boy. Let's see if you aren't against it," she purred temptingly.
She planted a deep kiss on me and then shifted her attention to her belongings. Out of the pile of sex toys, a large strap-on dildo emerged. It was not present the previous night. It was about 16 cm long, larger than me but not as big as the ones I had encountered in the last few days.
She returned to me, brandishing the dildo at eye level.
"Interested in giving it a go now?"
I nodded silently.
She fetched a tube of lube and placed it next to me on the bed. Coming back, she began lavishing me with passionate kisses while her hand roamed over my body and the hard plastic toy pressed against mine.
All of a sudden, a squirt sounded out. Her lubed fingers approached my anus and began slicking it. I let out a silent moan.
Her fingers entered me, one at a time. I used all my self-control not to utter a sound.
After several minutes of foreplay, I was in another world. One hand reached for my penis, but she stopped me.
"Give me a moment."
She murmured.
She climbed off me, slathered the dildo with lube, and slowly slid it into me.
As I felt my anus being stretched wide open, the scene in front of me was beyond my wildest dreams. I lay stomach up, legs spread eagled in the air, with her ample chest undulating gently as she worked her way inside me.
She took hold of my penis and began stroking it. I was in pure bliss.
I rolled my eyes back and cherished every single moment. It lasted for almost 30 minutes. It was slow and sensual, with pauses every few minutes for intimate kisses as my climax grew steadily. When she stopped stroking my penis, I would experience gentle caresses on my hair or stomach. I was in heaven.
Finally, after nearly 30 minutes of anal sex, she freed me. The force of her strokes increased, and before long, I reached a shuddering climax on my stomach.
That marked my first time being penetrated.
To be continued.
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