“Tickets and resort booked using your credit card. Await further instructions on packing.” Mistress Victoria’s message flashed on my phone.

I was buzzing with excitement for our weekend getaway to the island. Mistress Victoria and I were headed to a secluded resort in the Atlantic. It was a sex-positive, clothing-optional paradise. The thought alone was enough to make my cock throb with anticipation.

For the last ten days, I had been locked in chastity. My balls aching and my body desperate for release. It had been torture, but I knew this weekend would be worth it.

We were scheduled to leave on Friday evening, returning Sunday evening. All week, I couldn’t stop dreaming about the trip, fantasizing about the wild adventures that awaited us.

Thursday evening, a new message from Victoria arrived: “Pack your toiletries and any necessary medications. Bring 1 thong, 1 jockstrap, and wear a sissy panty and a dress of your choice for travel. Do not remove the chastity cage.”

The list sent a thrill through me. It was clear I would be nearly naked for the whole weekend. My cock twitched in its cage again.

I groomed myself thoroughly and packed everything in a small backpack. I couldn’t contain my excitement. Sleep came fitfully, my mind racing with kinky thoughts.

Friday

I met Victoria at the airport. She was stunning in a scarlet red loungewear set that hugged her curves, emphasizing her thick thighs, shapely ass, and large breasts. She wore heels that lifted her rear even more, making it impossible for anyone to ignore her.

I bowed my head in greeting when I saw her. She didn’t acknowledge it, but I didn’t expect her to. The flight would be short, but we had a ferry ride ahead of us once we landed. From there, a buggy would take us to the resort.

By 9 p.m., we were on the island. The resort was luxurious, occupying a large part of the island with pristine beaches surrounding most of it. As we checked in, I noticed a middle-aged couple strolling around naked, beers in hand. The decor was unabashedly kinky, with framed photos of erotic art on the walls and sex toys displayed in glass cases. I even saw a woman on a leash, led by a muscular man, with a plug clearly visible in her.

We were shown to our suite, a spacious first-floor room with a pool and beach view. The suite had two bedrooms and a large living area with a bar counter and mood lighting in shades of blue, red, and green. A retractable screen covered all sides of the suite, offering unobstructed views. I could already see the beginning of some intimate activities happening in the rooms nearby.

Once inside, Victoria commanded me to strip.

“From now on, you will remain naked. I hold the key to your cage. I will unlock it when necessary, but you do not need to ask permission for the bathroom,” she said, her voice firm. “Shower once a day, but I will let you know if you need more. Your room should always be open, and the screens should stay retracted. I won’t repeat myself.”

I nodded obediently.

“You can relax now. We’re waking up early tomorrow. Be awake by 7 a.m.,” she added, before walking off to her room.

Saturday

I woke up at 6:30 a.m., took a quick shower, and waited for Victoria. I stood facing the pool, admiring the view.

“Put on your thong. We’re heading to the pool,” she said, stepping out of her room.

I quickly slipped on the thong, securing it over my locked cock.

Victoria was dressed in a robe over her swimwear, carrying a pool bag. We walked to the pool area, where many guests were sunbathing in the nude or topless.

Victoria found a pool chair and settled down, her white bikini drawing appreciative glances from many of the men. She had a commanding presence that seemed to attract attention wherever she went. I stood beside her, awaiting further instructions.

“Stand facing the pool. Remove your thong. Kneel next to me,” she commanded.

I obeyed, the feeling of being exposed to the crowd making my cage twitch. A few guests noticed, some staring openly, while others seemed to go about their business. My knees began to ache from the position, but I stayed still, trying not to react. Victoria fastened a collar around my neck.

After what felt like an eternity, Victoria spoke again. “I’m going for a swim. You can either sit here or get a drink, but do not remove the collar or thong.”

I didn’t feel like drinking, so I stayed by her side, stretching my legs out on another chair. Victoria swam for a while, chatting with people at the pool bar. Some of the men glanced my way, but most seemed content to enjoy their own activities.

When she returned, I helped her dry off, but she had another order for me.

“Get on all fours,” she said, her voice leaving no room for disobedience.

I complied, and she inserted a medium-sized buttplug, which made me gasp. I could feel it pressing into me, the discomfort turning into something darker, more thrilling.

“Let’s go for a walk around the island,” she said, snapping the leash to my collar.

I walked behind her like a dog, my humiliation growing with each step, but there was also a part of me that reveled in it. We passed by the reception, the restaurants, and finally arrived at the beach. I could hear the sounds of the ocean, the laughter of other guests, and the occasional moan in the distance as I crawled in the sand, my cock leaking precum.

Victoria sat down on a beach chair, and I knelt beside her, my body aching from the prolonged position.

A man in his 40s walked toward us, his muscular frame catching my eye. He stopped in front of me, pulling down his underwear to reveal his thick cock.

“You know what to do,” Victoria said.

I obeyed without hesitation, taking his cock into my mouth and beginning to suck, the feeling of it growing hard in my throat sending waves of arousal through me. The taste of precum filled my mouth, and I deepthroated him, gagging slightly as he moaned in pleasure. The crowd around the beach watched, some exchanging murmurs and laughter. I didn’t care. This was what I was here for.

After several minutes, he came in my throat, and I swallowed every drop. He left without a word, and I was left panting, my cock still straining in its cage.

Victoria smiled at me, her dominance clear. “Time to go back to the suite,” she said, and I followed her on all fours.

We arrived back at the suite, and Victoria wasted no time in taking control.

“Sit,” she ordered.

I obeyed, settling on the bed with my legs spread wide. I could feel the plug pressing uncomfortably against me.

“Tonight is going to be fun,” she said, a playful smile curving on her lips. “You’ve been such a good boy so far, but we both know what you really want.”

“I know you want to touch yourself. I can see how hard you are,” she whispered, her breath hot against my skin. “But you’re not allowed. Not yet.”

She moved to the dresser, pulling out a small black bag.

She returned to me, holding a set of restraints in her hands. Without a word, she secured them around my wrists and ankles, forcing me to lie flat on the bed.

“You’ve been locked up for so long, haven’t you?” she asked, her fingers caressing the cage, making my hips buck involuntarily.

I managed to nod.

Victoria turned away and picked up her phone, typing a message.

“Stay like this until 5 p.m. We are meeting some guests at 6 p.m."

At around 5 p.m., Victoria untied my hands and legs. The plug was also removed. She asked me to stretch my body well, as it was going to be a long night. She was wearing her leather dominatrix suit.

At around 5:30, Victoria got up.

“Follow me,” she said. “You can walk.”

We went to the beach, where a bunch of cabanas were set up. These were a bit larger than usual and looked like a play area by the beach for kinksters. It had screens all around. The screens were obviously retracted.

I saw a bed set up in the center of the cabana. The red mood lighting was on, and lounge furniture was arranged around the bed.

The guests started arriving. There were around three couples in attendance, and then the guy I had sucked off in the morning was also present.

Victoria stood and thanked everyone for joining. I was still standing beside her.

“I give you my slave boy today! For your pleasure! Never ask! Just play. This slut will entertain you tonight, and I’ll be the proud domina who will be watching. Let the fun begin!” she said.

She unlocked my chastity cage.

I jumped onto the bed and went into the doggy position. All the guests were devilishly smiling at me.

One of the men walked up to me. He was in his late 50s, a big Caucasian. He removed his shirt, shorts, and underwear. He lay on his back, relaxed, with his arms over his head.

“Suck it, bitch,” he said.

I crawled like a dog to him and started sucking his penis. He was about 6 inches, and I deep-throated it very well. In a few minutes, he ordered me to stop, and when I lifted my head, I saw his partner, nude, sitting next to him. She was a mature woman with ample breasts, a tight ass, and a clean pussy. She asked me to get off the bed.

I got off the bed and crawled toward one of the couches. Another couple took hold of my leash and pulled me toward them. I could hear moaning in the background, and I assumed the couple was fucking hard on the bed.

Now, I crawled toward the couple holding my leash, and they appeared to be from Asia. The woman ran her fingers over my cheeks and slapped me hard, once on the right, then on the left. She kept slapping me very hard for about five rounds, after which a tear formed in the corner of my eye.

She stood up and pulled me by my leash back to the bed.

“Go like a dog,” she said in a thick Asian accent.

She was a tall woman with a lean body and perky breasts. She removed her robe, revealing her full body to everyone.

“Count to 10,” she said.

With her big bare hands, she spanked my ass very hard. I’d never experienced this before. I started wailing in pain after the first few spanks.

“Count louder!” she screamed.

“3…”

Spank!

“4…”

Spank!

“5…”

.

.

.

And 10.

I could feel my ass burning from the spanks, and I knew it would be red by now.

While all this happened, the first couple was fucking hard in doggy style. The guy started cumming and let out loud moans. I was sure his partner had much more in store for the night.

She called me over and said, “Lie on your back. Open your mouth.” I obeyed.

She sat on my mouth. “Drink my husband’s cum,” she said.

I could feel the hot cum of her husband dripping from her pussy into my mouth. I sucked her pussy deep and hard, and she kept moaning all the while.

“You’ve trained an amazing slut, Victoria!” the woman said as I continued licking.

The Asian woman was watching all this silently as she held my penis tightly. It started getting hard. I felt her large hands squeezing my penis and retracting my foreskin to reveal my cockhead. She continued doing it, and I started moving my hips in pain. My cockhead was dry, too. I moaned as I kept sucking the pussy in my mouth.

The woman on my mouth stood up and went back to the couch, settling next to her naked husband.

When I slightly lifted my head, I saw the Asian woman wearing a black strap-on. It was huge on her petite body. She climbed onto the bed, lay on her back, and poured a boatload of lube on her strap-on.

“Ride it like a bitch in reverse cowgirl,” she ordered.

I got into position and slowly pushed the strap-on into my hole. It was painful at first, but then it slid down. The Asian woman held me by my hips and started thrusting.

“Fuck it like you want it, bitch!” she screamed.

I started moving my hips up and down faster, moaning as I did. I was facing the audience, and I noticed people around the cabana were also watching what was going on. I made eye contact with almost everyone as I kept getting fucked by the dildo. I moaned like a slut, and my thrusts became harder and harder. I was getting closer to orgasm. My body was tightening, and the Asian woman asked me to stop.

She quickly removed her strap-on and pushed me onto the bed, jerking me off very fast. I let out a loud moan as I came. The Asian woman collected my cum in her hand and rubbed it all over my face.

I was very exhausted by now, glued to the bed. In the next few minutes, the guy I had sucked earlier in the morning walked up to me.

The third couple had been silent up until now. They stood up and walked toward me. The third couple was of African descent, and both of them looked ripped, younger than the other couples. The black woman approached Victoria and kissed her deeply. Then, the black woman started sucking Victoria’s breast and slowly caressing her pussy as well.

The black guy and the guy I sucked earlier climbed onto the bed. They made me go into doggy style again. The black guy stood on the bed and started ramming my mouth with his thick black cock for 10 minutes. I could taste his precum. Then, the black guy lay on his back and asked me to continue sucking his dick. My legs were spread apart, and my ass was penetrated by the huge cock I had sucked earlier in the morning.

All my holes were filled with thick, veiny cocks, and I was being used in an island full of kinksters. This was the dream.

In a few minutes, the black man left, and his partner replaced him. She asked me to suck her pussy until she came.

I was getting rammed from behind, and my cock was leaking. I was getting close to my next orgasm, and I came in no time. I was shaking as I came, but the guy held my hips tight and kept fucking me, while the black woman buried my face in her pussy.

I could hear both of them moaning, and I knew they would cum soon. My face was fully wet with her cum, and my ass was getting filled with hot cum as well.

Both of them left, and after a few minutes, Victoria stood up and walked toward me.

“Thank you, everyone, for joining today. I hope you enjoyed using this slut.” Everyone nodded and acknowledged.

“Well, you have my contact. Reach out to me if you need to use him anytime in the future,” she said.

With that, the cabana began emptying out. I could feel my hole very wet and dripping.

“Get on all fours and come with me,” Victoria said.

I was again paraded around the island with my face and hole covered in cum. Cum was still oozing out of my hole. We eventually reached our suite.

“Rest,” Victoria said and walked into her room.

I drank a full bottle of water, took a shower, and slept for the night.

Sunday

When I woke up, it was around 11:30 a.m. I was starving, and when I went out, to my surprise, the dining room had a breakfast platter. Victoria was having breakfast as well, and she asked me to join her.

While I sat down for breakfast, she removed the collar from my neck.

I gobbled up the pancakes, the eggs, and drank some juice. It was refreshing.

“Q,” Victoria said.

“Yes, Mistress,” I replied curiously.

“You did well yesterday. I’m proud of you. And I’m proud of how you’ve evolved in this relationship,” Victoria said, keeping her hand on my cheek.

I smiled.

“Today, we leave here at 3 p.m. I’m giving you your reward. You are free for the next three hours and can do whatever you want. But not alone, we will be together as equals,” she said.

I started crying with overwhelming joy. “Thank you, Mistress,” I said.

“Call me Victoria until we leave here,” she said.

“Let’s go for a walk, Victoria,” I said.

I wore my jockstrap alone, and Victoria was in a black bikini today. We strolled around the island, got some fresh air, and talked about a lot of things, spending some quality time together.

We had a beer together at the beachside bar, both of us very relaxed. As we reclined in a chair with a view of the beach, I slowly grazed my hand over Victoria’s bra and felt her nipples harden. She let out a breath as I grazed it, and she removed one side of the bra to expose her breasts.

I went ahead and sucked slowly. Victoria let out sweet moans as I did, and I caressed her hips.

It felt amazing… After a few minutes, I sat on her lap with both legs around the chair and removed her bra. I started working her breasts with my hands, alternating between sucking on each nipple.

She was very aroused. I also lifted her arms and licked the sweat off her armpits.

I loved the salty taste of her sweat. I gently pinched and pulled both nipples, and Victoria let out a loud moan.

Our eyes met, and we smiled at each other. I rested my head on her bare breasts and hugged her tightly.

We stayed like that for a while and walked back to the suite.

Once we entered the suite, Victoria closed all the curtains and kept only one bedside lamp on in her room. She took me into her room and started stripping. I removed my jockstrap as well.

We were both naked and lustfully looking at each other's bodies. Victoria handed me a bag inside which there were so many sex toys. This was a signal that I could use any toy present in the bag.

Victoria walked near me and kneeled. I was able to see her curves in a more sexy way. With her left hand, she very softly caressed my balls, and with her right hand, she held my cock.

I’ve never spoken about my cock. I have a 6.5-inch uncut cock with decent girth. She looked into my eyes and licked the tip of my cock head. This sent a shock through my body, and my cock began to get fully erect. She pulled my skin back and gave me a blowjob gently. Her warm pink lips were wrapped around my cock, and she sucked it.

I let out a moan, and she seemed to enjoy giving me a blowjob.

A few minutes later, I helped her onto the bed and French kissed her deeply as I slowly rubbed her clit. She let out soft moans. I took a clit-vibrating toy and placed it on her clit as I worked around her body. I kissed her neck and licked it. I smelled her armpits and tasted her sweaty pits. I slowly licked all around her breasts and then sucked on her nipples. I then put my tongue into her navel and sucked it.

By now, I reached between her legs and started licking her wet clit. It tasted and smelled amazing. I also shoved two fingers into her pussy. It was warm and wet. I massaged her G-spot and finger-fucked her pussy as I worked on her clit.

Victoria let out moans, started squirming, and I observed her body tightening. She closed her eyes tightly and let out her first orgasm. I let her relax for 2 minutes, then got her into doggy style. I was able to see her huge right cheek and perfectly curved, mature ass.

“Can I use your ass, Victoria?” I asked her.

“Yes,” she said.

I spread her cheeks and licked her asshole with the tip of my tongue. She let out a moan. I buried my face in her ass now and started wildly playing with her asshole. I flicked my tongue, pushed it into her ass, and kept licking and sucking. While I was at it, I grabbed both of her breasts and squeezed them as well. Her moans were slowly getting louder.

I put two fingers into her mouth, and she sucked them like a hungry and horny woman. I took out my fingers and pushed them into her asshole. Initially, it was tight, but then they moved in. I fingered her asshole slowly, increasing the pace. In the meantime, I took a thick vibrating dildo and pushed it into her pussy, keeping it on maximum vibration.

Victoria held onto the sheets of the bed very tightly, and her moans slowly turned into screams of pleasure. I didn’t stop fingering her ass, and now I was pushing in three of my fingers, fast and rough. She had her second orgasm in the next couple of minutes. She let out a loud scream this time.

My cock was leaking uncontrollably from everything that was going on.

She was still in doggy style, shaking from her last orgasm. I went near her ear and whispered, “What do you want now, Victoria?”

“I want your cum in my throat,” Victoria said.

“Should we go to the balcony?” I asked her.

“Yes!” she said.

I removed the dildo and plugged her ass with a medium-sized plug. We both walked to the balcony.

The pool and the pool bar were busy as always.

As we both stood naked, we saw a few pairs of eyes turning toward us.

Victoria got into doggy style with her ass facing the transparent glass of the balcony and started cleaning my cock out of all the precum. I let her hair free and clutched it tightly.

By now, she took my cock into her mouth, and I started to fuck her mouth. I could hear murmurs and cheers coming from the pool. I closed my eyes and fully indulged in the act. My cock was growing hard in her mouth, and Victoria didn’t close her mouth once.

I started thrusting into her mouth hard, and she began gagging. Her saliva leaked from her mouth to her breasts and to her pussy. I continued to thrust, and she started giving out loud moans.

I knew that the full crowd was watching us now. I was getting close to orgasm as well. With a couple more hard thrusts, I came deep in Victoria’s throat and let out a wild moan.

Both of us smiled back. I kept my cock in her mouth until all the cum was drained. I knelt down and thanked Victoria.

We then went to the shower and planned to take a dip in the tub along with a bottle of champagne. We sat opposite each other, relaxing and playing with each other's legs.

Time was up.

I got out of the tub and got on all fours.

I asked Victoria, “What’s your next order, Mistress?”

Mistress Victoria smiled at me as she drank her glass of champagne.

It was one unforgettable island weekend!