My Island Prison

They always say that wealth can be a curse as well as a blessing, but I never really understood it until now. Certainly when I first inherited my millions, I couldn’t see any downside to it. In an instant I was lifted from my 9-5 rut into a life of leisure, glamour and excitement. And the women! My god, I was really playing in the major leagues now. Women who, I’m sure, would never have looked twice at me when I was a working stiff suddenly seemed to find me endlessly fascinating. Did it bother me to think it was just my money they loved? Not really. I was having sex with fantastically beautiful women on a regular basis, and as someone once said, as shallow and meaningless experiences go, it’s one of the best.

None of them really meant anything until Anne, though. I can’t remember where we met – some charity function I should think. I’m sure there were dozens of glamorous women there, but I could see no one but her. I went over to talk to her, and was suddenly seized with a fear that my newfound confidence with women would desert me now when it mattered most, and I’d go back to being the old me, this boring schlub who women hardly seemed to notice. I needn’t have worried. She seemed just as fascinated by me, and before long we had rented a room in the same hotel.
The next few weeks passed in a blissful haze. I had to admit that sex with someone I cared about (as well as fancied like mad) was a richer experience. Best of all, she seemed instinctively to understand what I liked. She was always quite dominant in bed, never asking what I wanted her to do but taking the lead and telling me what to do. Most thrilling of all, although she would always get at least one orgasm, our encounters would sometimes finish without me getting any release. If I asked whether I could also cum, she’d smile sweetly and say “Maybe next time, honey.”
Once, as we lay together in each other’s arms afterwards, I admitted that I found it really thrilling the way she took charge, and especially how she would sometimes deny me orgasm. Best of all was the uncertainty. We’d start making out, my levels of sexual desire would go through the roof, and I’d never know whether it would end in release or being told I had to wait until next time.
She smiled. “I know that, honey. That’s why I do it to you. You see, I’m always doing what you want, even when I seem to be denying you. Of course…”
“Yes?”
“Well, I was going to say… if you want, we could take it even further.”
“How?”
“Well there are devices they make which lock around your cock and balls. Chastity belts, in other words. Don’t get me wrong, I’m not saying that you’d jerk off to get sexual release when I deny you, I know you’d never do that. It’s just that the thrill for you would be so much greater knowing not just that you wouldn’t, but that you couldn’t. That you were completely in my control.”
I think it was those last few words that did it. The idea of being completely in her power, hoping for an orgasm but unable to do anything but appeal to her for mercy, made my head swim. I can’t even remember if I actually said yes to it, but within a couple of weeks she announced that the belt she had ordered over the internet had arrived. Looking back, I think she must have ordered it before discussing it with me, counting on the fact that she could talk me into it.
I must admit I was shocked when I saw it. I suppose I had imagined something symbolic, just something to remind me of her power over me, all the more thrilling since no one else would know I was wearing it 24/7 under my clothes. What she was showing me looked more like a medieval torture device. There was a thick metal waistband, attached at the front to a metal tube for my penis and a ring which locked around my scrotum.
“Wow, this is a serious piece of kit,” I said. “I presume there are two keys?”
“Yes,” she said with a teasing smile, “And I’m keeping both of them!”
“But in an emergency…”
“In an emergency, you call me. Come on, there’s no point to this if you have a key, you know that. You could just let yourself out and jerk off whenever you wanted.”
“I would never do that!” I protested.
“I know, honey. But like I said, the thrill is knowing not just that you wouldn’t, but that you couldn’t. Trust me, you’ll see.”
My god, she was right about that. I had never seriously considered jerking off after she had denied me release. But there was a world of difference between knowing at the back of my mind that it was there as a last resort and knowing that it wasn’t, and I had no chance at all of cumming without her permission. Just as she said, the thrill when she denied me was a thousand times more intense, knowing that her word really was final.
To make matters worse she started denying me more and more often, making my need to cum, and my frustration when she denied me yet again, all the greater. Very gradually, denial had gone from being the occasional, thrilling exception to an otherwise satisfying sex life to being the norm – now being allowed to cum was the exception, and I was always securely tied up so that she’d have no trouble locking the belt back on me afterwards. I had to admit that the orgasms when she finally did relent were mindblowing – but knowing that only made it all the more frustrating when she said no.
Things came to a head one hot summer night. I knew that the next morning she was flying home to stay with her parents for a week, so I thought surely she would let me cum this time, especially as she had denied me the last three times. She started to kiss me, but the thought of getting so turned on and then not getting a release yet again was more than I could bear. I pulled away from her kiss.
“Honey, before we start… I would REALLY appreciate it if you would let me cum this time.”
“Come on, you know how this works. No guarantees. If you know in advance, it’s like Russian Roulette with no bullets in the gun. Where’s the thrill in that?”
“Sure… but lately it’s been like Russian Roulette with five bullets in the gun and only one empty chamber! The thrill of uncertainty is all very well, but sometimes I need the thrill of actually cumming too!”
“I know that honey, and you do get to cum sometimes. But not every time, and certainly not when you demand it. That’s not how this works at all. Trust me, I know what’s good for you.”
She started to kissing me again to prevent any further argument. I really thought that she might let me cum this time, but instead I just got that smile again as she said, “Maybe next time, honey.”
I tried to hold myself together, but a single tear rolled down my cheek.
“What is it, honey?”
“It’s just that… you’re going away. I won’t even see you for another week. I’ll be so frustrated by then.”
“Mmm,” she agreed, “and of course you have no guarantee that I’ll let you cum then either.”
For the first time, the full helplessness of my situation dawned on me. I had no guarantee that I would ever cum again. It was purely down to the whim of a woman who clearly got almost as much pleasure from denying me as she did from the orgasms she had herself. There was nothing I could do but hope and pray for her mercy.
Well, almost nothing. Nothing was ever said about it, but I noticed that my success rate definitely improved if I showered her with expensive gifts, both surprise gifts and things she had none too subtly hinted that she wanted. I don’t know if it was a deliberate policy on her part to reward me for doing what she wanted, or whether being in a good mood just made her more likely to take pity on me.
Whichever it was, I soon learned never to say no whenever she asked for something. I guess I should have suspected that it was really my money she was in love with, but that was the last thing on my mind. Nothing mattered beyond getting out of this infernal belt as often as possible. So I didn’t bat an eyelid when she suggested that my bank account be put in both our names. After all, she said, she was so often buying things which I ended up paying for (which was undoubtedly true) that it was simpler if she had access to the account directly. I don’t suppose I really accepted this logic, but I was in no position to argue.

However, I couldn’t hide my surprise at one suggestion she made a couple of years into our relationship. She announced that she’d found the perfect get-away-from-it-all holiday destination, a tiny island, hundreds of miles from anywhere, completely unspoiled by tourism. There were no cars on the island and nothing you could really call a road, she explained, and no hotel, but that didn’t matter as she’d found a cottage we could rent for a couple of weeks.
I was amazed. She was such a city girl, loving the bright lights, luxuries and pampering. Could she really have this other side to her that longed for the simple life? It seemed very unlikely, but I knew better than to argue. And in truth, the idea of us just being alone together for two weeks with no distractions reminded me so much of when we first got together, I guess maybe I hoped things would go back to the way they had been back then. I was certainly encouraged when, just before we left for the airport, she produced the key and started to remove my chastity belt. Seeing the look of joy and excitement on my face, she laughed and said,
“You dumbass, this is just so you can get through the metal detector at the airport! This baby’s going straight back on when we’ve landed, believe you me.”
She was as good as her word. She even insisted on standing right outside the bathroom door on the plane when I had to pee. “I don’t want you coming back 5 minutes later with some story about how there was a queue and you had to wait,” she said. I remember thinking that I was so desperate I could probably cum just as quick as I could pee anyway.
Once we landed and got our suitcases back, she took me straight away into the airport bathroom and locked the belt back on me, just as she’d promised. I saw also that she hadn’t been lying about the island. The airport was little more than a tin shed, with no bar, restaurant or gift shop, only the basics that every airport had. The island itself was windswept and barren. To get to our cottage, we had to hire a local with a cart pulled by a donkey, which bumped slowly over a rutted dirt track for more than an hour before we got there. Once again, I thought to myself – this is her idea of fun?
Once we arrived, I carried our suitcases into the cottage, while she arranged for the donkey cart guy to come and get us in two weeks and take us back to the airport, since as she explained we’d have no other way of contacting him as there was no phone. Once she came inside, without a word she pounced on me, practically ripped my clothes off and threw me onto the four poster bed. The next week was, just as I had hoped, exactly like when we first met. With no distractions, we could hardly keep our hands off each other, and we had sex five, six or seven times every day. With one tiny but important difference. I didn’t get to cum. Ever. Every time, when I thought she would finally relent, she simply smiled that smile again and said “Maybe next time, honey. And after all, next time will only be in a couple of hours, so why worry!” she laughed.
After a week of this I was seriously beginning to wonder whether a person could go insane from sexual frustration. Finally, I broke down. I pleaded with her. I said I would do anything, absolutely anything, if she would only let me cum. She seemed to consider it for a while, then said, “OK, I guess you’ve been pretty patient. To be honest I’m amazed you didn’t crack before now!” She disappeared into the other room and came back with that glorious key and put it in the lock. Or rather, she tried to. It wouldn’t go in.
She looked at me, seemingly in genuine puzzlement, and then said “Oh my god.”
“What?!?” I said.
“When we were packing, at the same time as I took off your belt and put it in the suitcase, I was thinking about padlocking my suitcase shut. You know, to make sure the baggage handlers couldn’t go through my things. I must have got the two keys mixed up.”
“So?” I prompted her. “The key you thought was for the padlock will actually open my belt.”
“Well that’s just it. I didn’t lock my suitcase in the end. I left the padlock and the key for it at home. Or rather, it looks like I actually left the key to your belt at home.”
I couldn’t speak. Hot, salty tears rolled down my cheeks and I become to sob uncontrollably.
“I am sorry, honey, I really am. I can’t believe I was so stupid. But I promise I will unlock you the moment we get home. Hey, isn’t it a shame we found out? Now the second week won’t be as thrilling for you as the first.”
“Thrilling?!?”
“Yeah, you know, the thrill of not knowing, wondering if you’ll get to cum this time. Now you’ll know for certain that you won’t!”
I began to sob all the more. The next week was pure hell for me. She insisted that we had sex just as often as before. If I refused, she reminded me that even when we were back home the key would still be in her possession, and I should think very hard before pissing her off. By the end of the two weeks I was as crazed and frustrated as she was relaxed and satisfied.
“Thank god there’s only one day to go,” I said. “What time does the donkey cart guy get here?”
“I told him noon,” she replied. “That should get us to the airport in plenty of time for… oh my god!”
“What is it?”
“The metal detector. You’ll never get through. They won’t allow you on board!”
“Metal detector? Do they even have one here?” I said, trying not to let the panic I felt show in my voice.
“Of course they do. Every airport does, however small. They have to.”
I couldn’t speak. She was right, of course.
“Look don’t worry, as soon as I get home I’ll mail… no, there’s probably no delivery here. OK then, I’ll grab the key, turn around and fly straight back. Oh wait, there’s only one flight a week. Well I guess there’s nothing else we can do, you’ll just have to stay here one more week. I’ll call the owner and arrange to extend the rental. I got the impression people weren’t exactly beating down her door to rent it, so there shouldn’t be a problem.”
“I’m really sorry, honey, it looks like there’s no other way. But it’s only a week, that’s not so long. And after all, you won’t have me here driving you crazy, eh?” she added with a laugh.
The next day, as I sat on the bed and watched her packing her things, it was all I could do not to cry. Just before closing her suitcase, she pulled out a thick hardback book and handed it to me saying:
“I’m worried you’re going to be bored staying here on your own, what with having no TV, so why don’t I leave you the book I’m reading. It’s really pretty good, and certainly long enough to keep you busy for a week. I might be a bit bored on the plane without it, but I’m willing to make that sacrifice since it was my screw up in the first place.”
I was puzzled. She was reading this book? When? I didn’t recall ever seeing her read it, or any other book. Glossy magazines were more her thing. Still, she was right that I would need something to do. I looked at the title. “The Count of Monte Cristo, by Alexandre Dumas. Translated from the French by…” French? Just when I thought things couldn’t get any better.
The donkey cart duly showed up on time, and as I waved goodbye, she turned around in her seat a blew a kiss to me. I trudged back into the cottage and wondered what to do with myself. I didn’t feel much of an urge to start this book of hers. Literature had never really been my thing. But in the absence of anything else to do, I eventually picked it up and started reading.
After a while, I had to admit it wasn’t half bad. It told the story of a man locked up in an island prison called the Chateau d’If. The man who imprisoned him knew he was innocent, but locked him up anyway to hide a guilty secret of his own, which only he and the prisoner knew about.
When I think about what happened next, I am always amazed at how perfect her timing was. A week had gone by since she had left. I was just thinking about what time the plane would land, how long the donkey cart would take, and concluding that she might arrive at any moment with that blessed key. Then I turned a page in the book and found a handwritten note. It had been taped in place to prevent it falling out. I started to read it.
“Hi honey,
If you’ve been following the plot so far, you should have a pretty clear idea of your situation. I won’t be coming back with the key to your belt, at least not for a while, and you won’t be leaving the island. In case you’re wondering, it was about the money, all along. Sorry if your feelings are hurt, but I’m guessing that’s the least of your worries right now. I guess you thought you’d met the woman of your dreams. Well, to coin a phrase, “Maybe next time, honey.” Though it’s hard to see how there can be a next time for you. Even if the island is teeming with gorgeous young women, which I doubt, you’re not that much good to them in your current state, are you? I hope you enjoy your new life on the island. I’ve arranged for some food and other essentials to be delivered to you every week, since the village is such a long walk away. Don’t worry about the cost, it’s my treat! Oh, and the cottage is bought and paid for, so don’t worry about that either.
And don’t worry about never seeing me again. I promised you that you’d be allowed to orgasm sometimes, and I’ll stick to that. I can’t say how often I’ll visit – well, you remember life in the big city, don’t you? So much to see, so much to do, especially when you have lots of money! But I will try and visit from time to time, I promise. And when I do, you’ll get an orgasm – maybe. Hey, that’s doubly thrilling for you, isn’t it? Never knowing when I’ll visit, and not even knowing if you’ll get an orgasm even when I do! I’ll see if I can’t think of some other ways to surprise you too. Did you like that part in the book where the jailer gives all the convicts a severe whipping once a year, on the anniversary of the day they were locked up? Now there’s an idea!
One thing you can count on, though. That belt is only coming off when you’re securely manacled to that beautiful four poster bed, and it will be locked back on before your wrists and ankles are unlocked. No exceptions. You’ll never be free again without your belt on, which means of course you can’t leave the island because of the airport metal detector.
Oh, and at the risk of spoiling the ending of the book for you, he eventually escapes by swimming to another island nearby. In your case the nearest island is more than 500 miles way, so if you fancy trying that I’d suggest you have a couple of practice swims first! Gee, I guess that’s why there are no boats coming to the island either…
So I guess it’s goodbye for a while! Oh, and a word of warning. As you’ve probably guessed, there is a phone on the island, at the airport. Maybe you’re thinking you might phone the police on the mainland and tell them what I’ve done to you? Or call your bank, tell them to suspend my access to your account? Big mistake. If I get the slightest hint that you’ve done anything like that, the keys to your belt are going straight down the nearest sewer. That’s right, you’d be condemning yourself to never having an orgasm, or even an erection, for the rest of your life. Is that something you’d like to do? I thought not. To save your dignity, I’ll be telling people here that you’ve decided to go and live on a retreat, far away from the pressures of the modern world. Do nothing to dispel that illusion, and you and I will get along just fine.
(N)ever yours,
Anne” 

But I could hardly read the bottom of the page, my eyes were so filled with tears. They fell onto the paper, making the ink run. How could she do this to me?