The Captive of San Ramiro

"You will NOT speak unless you are spoken to, and IF you are spoken to, then you will reply 'Yes MISTRESS!'"

"Fuck YOU bitch!" I cried.

"Wrong answer. Sounds like you need to be broken. Slave!" And she slapped me again, this time harder.

Aurora went on, "Ground rules here. First, welcome to Hell. For as long as you are on this island, you are our slave. Your new role is to serve us. NOT the other way around. You follow our orders, no matter how degrading you think they are. Do you fucking understand?"

"Hey look, I, uh, I'm sorry, but can I go now? I don't want to be a slave, really, I don't want to do this, this isn't funny, I..."

"NO!" Then I felt her slap me again, hard. Tears came to my eyes.

Then she reached down, and I felt her grab my dick again, now limp. Barely a minute ago, it had been about to geyser all over the place.

"Look at you, all chained up. Looks like you don't have a choice do you. You belong...all...to me now. You'll LIKE that won't you. My property. My little bitch. We're going to have some FUN."

"Well, uh, I mean, yeah you are pretty hot, but you won't hurt me will you?"

I guess maybe I could get used to this, I thought. She WAS beautiful, and I admit it did give me a pretty perverse, kinky feeling to be ordered around and abused by a hot young girl like this, back upstairs, but now, I wasn't so sure...

She smiled at me then. "If you are a good little slave slut, I'll reward you. But! If you are a bad, disobedient little brat then, I swear I will make it hurt like you've never been hurt before. And now, Kayla and I are going to break you in."

I looked over at the foot of the stairs and standing there was this blonde girl, long hair, gorgeous body (like everyone else here) and dressed like a naughty slutty cheerleader- one of the many girls I had fallen helplessly in love with that night. Only now, she was also holding a whip, and looked far less lovable.

The two girls unshackled me from the wall but took no chances, cuffing both legs together and my arms behind my back. They dragged me to a table and tied me to it, pinning my arms above my head, face down on it. I suppose I could have fought back, resisted, but somehow I didn't. It was almost as if the girls knew I wouldn't. It was as if, they seemed to understand a part of me I hadn't yet come to grips with.

Then I felt Kayla have her way with me with the whip, feeling the sting of each lash. So beautiful, but so cruel, I thought. I learned that night, to block the pain by imagining it being someone else, lying there on that table, someone else's pain, trying to distance myself from her, imagining me somewhere else- upstairs in the pool, with this beautiful blonde girl- whose whip would sting me again and again and bring me back there, helplessly chained face down on that table.

"THANK me properly for breaking you!" she said.

"Thank you mistress."

"You are my worm, my little bitch. You aren't worthy of even licking my feet, let alone fucking any of our guests."

"Yes mistress."

"INFERIOR!" She cried. "Born to serve, bred to obey, not to breed!" SMACK!

After a bit, the girls released one of my hands, and told me to pleasure myself.

"Go jerk it off for us. Let me see you stroke that puny little thing. You better cum for us, because it's going to be the last chance you get for a long while."

Shaking, embarrassed, I began stroking my now limp dick with my freed right hand, faster and faster.

I was visibly shaking. I wanted, desperately, to pleasure myself to orgasm, but I was too nervous, frightened, and self-conscious from what I had just gone through. And, it hurt, all over. They seemed to sense it, too. After several minutes of vigorous rubbing, all I could manage was a half-staff erection, and barely that. And to think that just a couple hours earlier I had felt I could have exploded in my pants. The girls seemed to cheer me on, laughing at my futile efforts to achieve orgasm in front of them.

"Ohhh...that poor little man won't let go huh? So sad... Oh well!" Kayla smirked. "You had your chance. Guess we better lock him up."

"Wait, what are you doing? What IS that?" Aurora had brought out this device that looked like a small metal cage. She kneeled in front of me, and attached it to my balls and penis. She then locked it into place with a small lock. The soft click of the lock seemed like the clang of a prison door.

Aurora stood up, grabbed my hair, and twisted my neck to look at her. "This is how it works. Obviously, your limp little dick isn't going to be of use to anyone here. Your body, however, is. That belongs to us now. We own you now. While you are on this island, you will serve us. Do chores for us, amuse us, and maybe even pleasure us, if we are in the mood. You will not be able to pleasure yourself with that chastity device obviously. In fact, get used to peeing sitting down, ha ha. As a reward for good behavior, we will unlock your device and allow you to orgasm, but ONLY if you are really good...and OBEDIENT. Otherwise, if you DISplease us, if you so much as look at us crosseyed, you get this!"

Suddenly, pain exploded in my crotch. I screamed, and jumped into the air. I was writhing from the burning jolt of electricity that had just been delivered to my genitals.

Aurora waved a keychain in her hand, with a push button device. "You can guess what this is. It can unlock that... (She pointed to the device that now encaged my cock) Or it can..."

"WAIT NO!! I UNDERSTAND!"

...."Do this." She pressed it again.

"PLEASE don't...please...I'll be good, please take this off of me, take it off... Mistress, please...Whatever you want... Can you take it off? Please?"

"She smiled. Maybe if you are good and do good work...but not yet. You have to earn that. Welcome to hell, boy."

And so began my internment as a slave of San Ramiro Island. That night, they had chained me in a cage in the basement, and the next morning, Aurora and I left for the mainland, aboard Ostermann's yacht. I was exhausted of course. All the other guests had gone home. I thought about Melanie. She had to know what had happened to me. I was disappointed and embarrassed. But oddly, the more I thought about my situation, the more I actually found Aurora to be really sexy, in spite of all of this. I still liked her. But did she like me? I knew that I was probably just a plaything for her but somehow that didn't bother me. It was, in a weird way, kind of hot. She kept a close eye on me all the way back to the mainland. We got to chatting, and much as she had been when I first met her, she was now much friendlier, nicer, more normal. I even told her, "I like you much better when you are like this, instead of, you know..."

"Well, thanks, but don't forget- I do hold your key." I had all but forgotten about that. A couple times when I was allowed some privacy, I tried to remove the cage on my cock but it was no use; it was too securely fastened. "And I'll give you a call when we want you back here. We need someone to help with the chores, cleaning, fixing things, and so on- I'll give you a call this week. And you WILL be here."

The first thing I did the very next day was, of course, try to get the chastity device removed. But the problem is, none of my ideas seemed to work. I was too embarrassed to call an actual locksmith, and my own futile efforts to pick the lock didn't work- it was too complex. So I did the next best thing- I went to a novelty sex shop. They would understand the problem, and maybe they would be able to help me, I thought.

As soon as I walked into a shop labeled "Paul's Erotic Boutique" I heard a voice from behind the counter say, "Can I HELP you? Oh wait...it's YOU! NO! I can't! Ha ha ha."

My heart sank. It was Kayla. I had the bad luck of walking into the one sex shop she happened to work at!

"So...we knew you would come here. If you don't want me to tell Aurora you were here, you will march your BITCH ASS OUT THAT DOOR right now" she said. "And trust me- you are blacklisted at every other sex shop in this county- Paul and Lacey have already seen to that. So don't try it. And you really don't want Aurora to know you were here, do you? You wouldn't believe what she can do when she's mad."

So much for my efforts to end my curse these cruel girls had put me under.

At work that week, Melanie seemed strangely distant. She had stopped by briefly, and apologized for what had happened. "Poor Zach, he gets the worst of it" she said. It suddenly all made sense why Zach had seemed so unhappy. "You guys were just too submissive out there." she said. "I know, you thought you were being helpful, polite, but that was just them testing you- I really thought they would let you join, or at least just send you home. I'm so sorry..."

"Yeah, but that girl, Aurora, I mean, she seems pretty cool and all, she's cute, but-"

"Yes, but she's not nice. She will make you do some pretty degrading things. And she will hurt you, if you disobey- Trust me, I know. I just hope you are okay."

"I'll be fine. They will probably let me out of this...you know, this whole deal, pretty soon anyway."

"Well, I hope so. I'm really sorry about the other night. I swear, I really am. I thought the worst that would happen was they'd just tell you no, you know, just send you home. I really didn't want you to end up like Zach, like, you know..."

Dude, I could have had you, right then; fuck, how did I screw that up? I wondered, bitterly, feeling sorry for myself and realizing that with my cock now in locked in chastity, I could no longer have ANYONE now- even if I had the opportunity.

Wednesday, after I had barely got home from work, my phone rang. "Ben. Get yourself to the yacht harbor. NOW" It was Aurora of course. Now despite my instincts telling me to run, I nonetheless planned to head straight there. If I had second thoughts, they were quickly dispelled when a shock to my genitals left me whimpering and doubled over.

"You LIKE that?" her voice said, over the phone. "Remember, I OWN you. So if you don't want any more of that, get over here now." I realized that even with remote control, she could still activate the shock device. What was the range on that thing? I wondered.

So, with that, Aurora and I hopped on Ostermann's yacht- Paul, ever the congenial host, even offered me a drink and sandwiches for a quick meal (Slaves were still well fed in these parts, it seemed, and he remained friendly) and we headed back out to the island. As soon as we stepped ashore, Aurora went from friendly cute innocent rocker chick to sadistic goddess mode.

There were relatively few guests here on a weeknight. Ostermann had explained that most of the wild sex parties were held on weekends, and on weekdays it was mostly slaves and masters- the male slaves going about their chores, their female tormentors punishing and tormenting them. That was good. They told me I wasn't quite ready to be seen like this, in front of a crowd of hot girls and horny guys at a full party- not yet anyway. Aurora and Kayla would break me in gradually though, promising that I would eventually be ready- ready for what though, I wondered.

I was ushered straight to the dungeon, where Kayla was waiting for us, again dressed in that naughty cheerleader outfit. "Strip naked for me." She said simply.

"Here are your slave clothes. You will wear this uniform as long as you work here. Put these on."

The shirt wasn't too bad- a pink flannel vest, fairly warm in case of the occasional cold windy days on the island, but the pants- they were the worst. They were tight, pink lacey britches with hearts on the buns- totally meant to be utterly feminizing and humiliating, but the thing that struck me was, there was a huge hole in the rear, right where my ass crack was. I thought I had remembered a couple people had been wearing a similar outfit the other night, but I had dismissed it as simply being part of the wild lifestyle out here.

"Good, now model them for us. Strut around. Shake it." Aurora commanded, after I had dressed. I blushed, but obeyed.

"Ohh, isn't he cute! What a piece of meat!" And I felt Kayla slap my bare ass, hard. "Now get to work. Scrub our toilets for us. We want our bathrooms clean enough to lick off the floor. Cleaning supplies are upstairs. There are eight bathrooms, but you better take your time."

So with that, I spent the next couple hours scrubbing toilets, floors, and shower stalls. The place was fairly clean to start with, so it wasn't too gross or hard. Not my ideal way to spend a Wednesday night but- hey at least I was on an island with two hot girls- right? That kind of made it bearable.

Well, more than two- Lacey was here, as was Zach's "Girlfriend" Erika, and a tall dark brown haired girl I didn't recognize- all of them dressed to the nines, in the skimpiest, sexiest outfits ever. Except they wore leather and boots, rather than frilly skirts and bikinis, I noticed, and all but Lacey seemed to have a particular "toy" to boss around. As for Zach himself, I spotted him out the window picking up trash outside and maintaining the electrical and water treatment systems, as was his job duty. Aurora had filled me in on the scoop on the way out. We weren't really supposed to speak to anyone else on the island unless spoken to, or if our jobs required it, including fellow slaves (under threat of corporal punishment) but I did exchange glances with one other poor soul, carrying a load of laundry down to the basement.

Eventually I went and found Aurora and told her I had finished. To which, she responded by smacking my buttocks, hard, with a leather thong. "You will kneel in my presence when you see me." She said. "In fact, you need more training on slave protocol. I'm going to leash you up right now. Pull down your pants."

She left me kneeling there in the ballroom, naked except for my shirt, and returned a short time later with a leather leash. She hooked the leash to a loop on my caged cock and yanked on it, dragging me into the men's restroom. God, she looked gorgeous in that skimpy leather outfit. My cock strained against its cage. It was a bit painful, the way she tugged on it as she dragged me, on my knees. "Let's see how you did!" She said. I could think of all kind of things I wanted to do with her, but right now- I only wanted to make her happy. And not just because of my cock being locked up and not because of the fear of punishment, either.

She dragged me, kneeling, in front of the toilet and lifted the toilet lid. I felt a boot on the back of my head force me into it. "Lick." She ordered.

What??

"You heard me. Lick it. You said you cleaned it, right? If it's not clean enough to lick, then it's not clean! Is it?"

"Well, yes but... I mean..."

"So. So you won't obey orders??"

"Okay, I will, but... I'm sorry." My tongue was already about to touch the porcelain- it had to be reasonably clean, right? I thought to myself, panicking. But instead I felt a jerk on my cock and felt her dragging me, back through the ball room, through the back office, and back down to the basement. We passed Kayla, who giggled with a girlish innocent laugh. "Wait, what are you... I'm sorry, I'll finish right now..." I stammered.

"Too late." Pain exploded in my groin as a jolt of electricity ran up my cock and down my legs, and I doubled over in agony. A second shock left me in tears. With Kayla's help, Aurora grabbed my arms and legs and shackled me to the basement wall, facing the wall.

"You fucked up, big boy!" WHACK! I felt the sting of her whip. "This is what we do to bad slaves who fuck up." WHACK!

"I'm so sorry Aurora, I didn't mean to..."

I could feel the sting of each lash, as she berated me for failing to do my job to her satisfaction. It hurt, but oddly, the physical pain was only a part of the pain I felt by displeasing her. For some reason I had desperately wanted to make her happy, and it wasn't just the fear of punishment. I mean, when we had chatted on the boat over here, I LIKED this girl. Plus, she was sexy. I mean, REALLY sexy. I was also surprised by how much of a huge turn on it was, to see this young, beautiful girl be so kickass and brutal. She would be strong, and I wanted to be strong for her. Each painful lash made me more and more aware of how much I relished her strength- but wait, how fucked up is that, I mean, this girl was fucking crazy, surely I can't be LIKING this?

"Aurora, I'm sorry, please, you don't have to hurt me..."

"Oh but I do. Maybe now you will learn how to please me, so maybe I won't have to make it hurt anymore."

"Okay..." I was nearly in tears of relief. My heart was pounding. I felt like I had just ran a marathon. The whole thing was really exhilarating, in a weird way.

"Can I go back upstairs and finish now?"

"We'll have Zach finish your job for you since you are too pathetic a slave to do it. Now, you need to get out of our sight. Your boat home is waiting."

Would you believe I actually felt jealous of Zach right then? Disheartened, I returned home that evening, my head full of confusing feelings and thoughts.

As the next couple weeks went by, I spent more and more evenings out at the island. I began to enjoy the tasks, and the attention I got from the girls, and loved the interaction I had with these sexy, powerful, and beautiful women. Especially Aurora, who had by default, become my chief "mistress" and commander, if you will. By the fourth day, one Monday evening after a wild party (I had not yet been invited to a full function yet) she had added a new twist. As soon as I arrived I met her in the basement, quickly dressed into those awful pink shorts with my butthole exposed, and knelt in front of her as she ordered. It was then that she had inserted a rubber plug in my butt. I felt it slide in, felt it violating my insides, filling and stretching me. I winced, unsure whether I could take this.

The sensation was awkward and uncomfortable, to say the least. Not to mention, embarrassing- but also in a weird way- I wanted to be strong for her. She told me it was a form of training and preparation, although for what, I dared not guess. After my chores, she had me strut around in front of the assembled crowd of slaves and girls, all of them giggling. "Look at him, walking like a little bitch!" cried one girl, a red bikini-clad model whose name I remembered as being Danielle. "Shake it for us!" she cried. When I didn't do so satisfactorily, I felt a hard swat on my butt. With the plug inserted it felt doubly painful. "Walk like a slut! Strut it. Pretend you are wearing a skirt."

"Wow! If I was a guy, I might want to fuck him!" Kayla exclaimed gleefully. They had me parade in front of them until they were satisfied and bored, then with a swat, Aurora ordered me to get to work.

During those visits to the island, Aurora and her twisted friends had other entertainments for me, some of them painful, some embarrassing, but I remember this one in particular as a foreshadowing.

Afterwards, I was down in the basement again. She ordered me on my knees. Kneeling in front of her, gazing at her leather boots. She had been, for the first time, happy enough with my work that she did not see fit to punish me, although wearing the anal plug had seemed like punishment enough. For several minutes I lay there in a state of awe and ecstasy. This gorgeous, strong, young girl, that insanely beautiful body, how I longed to touch her, lick her, kiss her- but merely being close in her presence like this, beneath her, was heaven enough. I could sense her standing over me, silently, as I groveled at her feet.

So this was love, I thought.

I felt a smack, not hard, but enough to make me wince.

"You may remove your plug." She told me. I did so.

"Mistress? Aurora, goddess?"

I could hear her smile.