Maid in Enclosed City - Cover

Maid in Enclosed City

by Anonymous (Enclosed City)

Copyright© 2009 by Anonymous (Enclosed City)

BDSM Sex Story: A boy wakes up from a drug-induced stupor in a strange-looking basement. He can't seem to remember who he is, and what's worse, he is now expected to dress like a maid and follow every order given to him. (This story contains gay rape and straight romance.)

Caution: This BDSM Sex Story contains strong sexual content, including mt/ft   Ma/mt   Consensual   Reluctant   Slavery   Gay   Heterosexual   CrossDressing   Fiction   MaleDom   Humiliation   Gang Bang   First   Masturbation   .

I awoke on a soft rug, drooling slightly. I felt woozy, as if I had been drugged. I tried to remember what the last thing was that happened to me, something that might possibly explain where I was.

I couldn't remember much.

"Sit up," said a voice. I wiped my face and rose to look at the world. I was in someone's basement, that much was clear. There was an amusing assortment of old appliances lying around: a microwave, a pottery wheel, and even a NordicTrak. The walls were kind of queer. They were made of big stones, and sloping inwards. It reminded me of a medieval castle I had once seen in Europe-- but I couldn't imagine anyone living in a castle.

The man sitting before me was dressed in a T-shirt and jeans. He looked to be in his late twenties-- a decade older than me. He was tanned, and clean-shaven. Our eyes met, and his stare became a grimace.

"Do you know who you are?" he asked.

I thought a little. I scratched my head. Scraps of memory faded disappointingly into nothingness. I tried to remember my mother and father, but everything came up blank. I couldn't even remember my name. I finally looked at this man, astonished. His face was the only one I knew in the world.

"I want you to know that I did not do this to you," the man told me. "You were kidnapped by other people, and they dumped you here. I am going to teach you how to recover yourself. I will not use drugs on you. I want to make you back into a useful member of society. Tell me everything you remember about yourself."

"I'm 16 years old," I said. My voice was familiar, high-pitched. "My name ... is..."

"You don't need to remember that," he told me. "You're mine now. You have no name."

"Huh?" I hadn't yet grasped the man's true intentions. My senses were still kind of foggy, I was worrying myself over my own mental state, and I didn't know whether he was playing a joke on me.

"Continue. What else do you remember?"

I looked around. "I can't remember anything." I looked down at my feet. I seemed to be wearing some sort of skirt. I ruffled it absently, trying to shake the confusion out of my brain.

"Come on." He tapped his foot impatiently. "Would you rather fuck a boy or a girl?"

My mouth dropped open. "Um. A girl."

"Excellent. From now on, I am going to give you instructions, and you will follow them without hesitating or questioning me. If you do not obey my commands you will be here a very long time and make other people suffer."

Almost as if on cue, a loud noise pierced my consciousness. It was distant, but unmistakable. It was a girl, screaming her lungs out in pain. And it didn't die out slowly-- it was cut off suddenly.

My wandering mind snapped into full consciousness. Immediately, I realized two things. The first was that this was no ordinary basement-- it was enormous. The second was that I was not just some lost boy, but I was a slave, and this was an underground torture chamber.

Now I looked back at this man with a lot more urgency.

"Don't stop to listen to the other sounds here," he told me. "There will be plenty of them. You must do whatever I tell you. Stand up."

I stood up.

"Look at yourself in the mirror." He pointed to a small mirror hung up on a stone pillar.

I looked in the mirror. I had a vague sense of what I looked like, but what I saw in the mirror made me tighten up in horror. My dark hair had grown long and straight, as if I had been asleep for a year, and draped silky behind my neck. There was a frilly white headpiece on the top of my head. My face was smooth and clean, and looked almost shapely. I was wearing a black and white French maid outfit with lace and apron, and on my feet were dark gray thigh-highs and shiny black shoes. It would be hard to tell me apart from a girl unless you looked closely. The whole time this guy had been talking to me, I was dressed like this!

"You will be wearing this every day for the foreseeable future," he said. "You are lucky to have such a dignified outfit. You will see other people here without such luck.

"Your name is now 'maid.' I will not give you any other name. If you come up with another name for yourself, I will hurt you until you forget it. Sit down."

I sat down, eagerly moving out of the way of the mirror.

"Maid, I am your master. You do not need to know my real name. You will call me Master. Is that clear?"

"Yes."

BAM! His hand came down on my face, and I saw stars. "IS THAT CLEAR?"

"Yes, Master."

"Good. Take off your panties."

Was he serious? I reached up my skirt and felt a thin piece of underwear. I looked up-- he was watching me to see if I obeyed. My face turned red. I pulled down the panties slowly, careful not to expose myself. They were white, with a bow at the front.

"Lift up your skirt, maid."

Now my heart was really pumping. With my panties dangling off of my right foot, I lifted up my skirt, exposing a limp, uncircumcised dick. I looked at him, sweating, awaiting some sort of confirmation.

"Stroke it."

I reached my hand under my skirt, cautiously.

"That is not good enough, maid. You must be able to come on command, within three seconds. Stroke harder."

I closed my eyes and started to jerk off. I couldn't remember anything to fantasize about.

"What are you thinking about?"

"Nothing."

BAM!

"Nothing, Master," I said, keeping my eyes closed.

"Open your mouth, maid."

I did so, and before I knew it there were hands gripping my long hair, and something big, warm, and moist was in my mouth. This was so wrong. Why was this happening to me?

"Suck on it, maid. Use your tongue."

Squirming against the force of his hands, I wrestled my tongue into position. He began thrusting in and out, and I could feel his cock growing inside me, taking up my whole mouth. Despite myself, my cock grew big and hard in my hands, and soon I was ready to come.

"Don't come unless I tell you to."

I slowed down my movements and focused on sucking his cock. I almost gagged on his head, and moved my tongue up and down his shaft faster, hoping I could make it end. I closed my eyes tight but I couldn't get myself away from the sensations attacking my long hair, my mouth, my cock. I almost came again and stopped my hand. The thrusting got faster now, and I felt like his cock was the only thing in the world, pressing itself down on my tongue, filling my mouth.

"Get ready to come, maid."

I jerked my hand up and down, fingering my head.

"NOW."

I gasped for air as I came, but suddenly he gripped my head and my mouth was filled with warm, salty stuff covering my tongue. I tried to spit, but he slammed my jaw shut with his hands.

"Swallow it, maid."

He stooped down and looked me in the eye, still holding my jaws shut. Frightened, I closed my eyes again and scraped Master's cum off my tongue with my teeth. It ran disgustingly down my throat. I ran my right hand down my wet cock as I tried to swallow it all. My fingers became sticky and I wiped them on my leg. My mouth was still salty. He took his hands off my head and I gasped for air. I fell backwards, coughing.

I felt a sponge slap against my inner thigh. "Clean yourself up and put your panties back on. Understood?"

"Yes, Master."

"You are my maid. You have no other purpose and no other name."

I took the soggy sponge and wiped off my dick and the inside of my dress. Somehow my dress seemed a lot more important to me now. Finally, when my dick shrunk back to normal size, I pulled up my panties. They still got a little wet.

"Stand up," said Master before I even thought. I stood and he put his hand around my arm. "I am going to take you to your bed now," he said. "Be grateful you have a bed, maid. You will not speak unless spoken to. You will not take off your clothes unless I tell you to. You will obey these rules even in my absence. Do you understand?"

"Yes, Master," I said placidly. No matter what was going on in my head, I could not betray anything to the outside world.

He started to walk towards the wooden door, carrying me by the arm. Outside the door there was a hallway. We were clearly in the largest room in the basement; we were at the end of the hall, and the other doors were right next to each other. It looked like they were dark inside, and as I passed by one of them I heard a girl's voice crying:

"No, no ... AHHH!"

It was the sound of pain, not pleasure. Without thinking I gripped my other hand around Master. He continued to walk down the hall, unhesitantly. How cute we would look to the outside world: a young man and his delicate teenage maid. But I wasn't a girl! I swallowed, and felt more of his cum running down my throat. And then he stopped and turned me towards a door, which he opened. Inside was a mattress, a pillow, and a sheet on the floor, surrounded by more stone walls. There was no light.

"Go inside, maid," he told me, and I obeyed. He held the door open, and I faced him. "Today you learned to obey me, if only a little. Tomorrow you will learn to want. It will take a long time, and it will be hard work, but when you have learned to want, then your training will end and you will be given a reason to enjoy your work. Are you prepared to learn?"

"Yes, Master," I said, although I had no clue what he meant.

"Then take off your shoes and sleep," said Master, and he closed the door.

Questions circled in my head. I knelt down and unfolded the sheet. Where was I? What country on Earth could this movie dungeon possibly be in? How could I ever enjoy working in this sadistic place, where I had to watch my every move, wearing a maid outfit and getting fucked by other men? Was the "reason" going to be a more intense punishment? I felt filthy, and my face was oily with sweat. I kicked off my shoes, and my maid costume itched, but I knew if I took it off he would do something sick. For now, I just wanted to sleep.


2


A light came on and shone in my face. I rubbed my eyes and tried to roll over. Then I got some of my long, silky hair in my mouth, and I remembered where I was and what had happened to me.

The light was coming from a ceiling lamp outside the one window in my room. While I had slept well enough, for all I knew, it was the middle of the night. I hadn't seen daylight since I arrived here. Somewhere close to me, I heard a door open, and an older female voice:

"Don't say a word. Stand up and come with me."

I slowly sat up in bed, wondering who my next-door neighbor might be. Suddenly it occurred to me to look out the window. But right next to that room was a bend in the hallway, and as soon as I had stumbled over and peered out they were already gone.

The door to my room slammed open and Master came in. Today he was wearing a dress shirt and tie. I put on my shoes. He lowered his arm and I put my dainty hand in his. He led me back towards the basement room where I had woken up before, but then turned and took me up a dimly lit spiral stone staircase. After going up one floor, we entered another hallway, and he opened the door to an immaculate, tiled bathroom with a medicine cabinet and a toilet.

"Do you remember who you are?"

"I am your maid, Master." Every time he made me say it I felt more crushed.

"Do you call yourself anything besides 'maid'?"

"No, Master."

"Are you my slave?"

I thought about it. "I am your maid, Master," I repeated.

"Good answer," he acknowledged. "You are not my slave. You must learn to care for yourself as well as me. Wash up quickly. With your clothing, do you think you should look like a boy, or a girl?"

I narrowed my eyebrows. "A girl, Master."

"Make sure you look like a girl, then. Across the hall is a kitchen. Meet me in there when you are done." He closed the door, leaving me alone.

I looked at myself in the mirror. So he was giving me some semblance of real life. That was nice and all, but ... why did he have to choose me, and not a girl? This was still fucked up beyond all belief. I brushed my teeth, then slipped the shoulders off of my outfit and scrubbed my armpits with deodorant. Someone had shaved them. Was it Master? On the sink was a razor, and I shaved myself meticulously. There was a tube of lipstick there, too. Oh, no. Was he expecting me to put it on? I took off the top and looked at myself in the mirror. My headpiece was crumpled (I tried to straighten it), and I had the faintest traces of jawbone, but otherwise I looked entirely feminine. My eyes were big and wide, my nose inobtrusive. I must have been picked specially for this job. I applied the lipstick carefully and smiled at my reflection, taking perverse pleasure in my looks. If I had to do this, I should at least do it well. I took a comb and ran it slowly through my hair. Then I remembered my instructions, slipped the top half of my outfit back on, and went across the hall.

The kitchen was unusual. There were stainless-steel countertops and big, industrial-size sinks. It seemed like it was built for a restaurant, or to accomodate large parties. In front of me were some vegetables and a carton of eggs.

"Good morning, maid," said Master, indicating his approval of my looks. "It is not enough to be obedient; you must be useful, too. Do you know how to make an omelet?"

"No."

BAM! I should have known better than that. "No, Master," I corrected myself, clutching my cheek.

"Then I will show you. Repeat everything I do." With mechanical efficiency he went through all the steps, and I copied him, even making toast at the same time. Within ten minutes we were done. "Put the food and two glasses of water on this tray, and take it into the dining room," he said, and left through a fancy double door. I didn't have much of a memory, but I was rather certain I had never been a waiter before. Now I was a waitress. I filled the glasses and took the tray in two hands through the door.

The dining room was, as the large kitchen had betrayed, a fancy piece of work with high ceilings, stained glass windows, and a long table suitable for an upper-crust banquet. Master was already sitting at the front, so I had to walk across the room to reach him. I placed down his breakfast and he motioned to a seat right by his side. I sat down, bemused. I was being treated well for a crossdressed maid. I couldn't reconcile the "training" from yesterday with the treatment today.

"Master?" I asked meekly.

"You will not speak unless spoken to, maid," he said, looking at me roughly. I shrunk in my seat and put my hands in my lap, feeling more effeminate than ever.

"You have to learn to follow my orders," he said by way of explanation. "Do not let your thoughts get in the way of obedience. The longer you take to learn, the longer I will have to train you."

And would would become of me when I was fully trained? I almost opened my mouth to ask him, but remembered his command and returned to my food instead.

But he seemed to read my mind. "When this is over," he said, "you will be comfortable with who you are, even in public. And you will be eager to do what I tell you without any need for punishment."

That wasn't going to happen, I thought. Unless if he drugged me (as he had promised not to) no amount of perversion was going to keep me from being humiliated by my dress, or make me comfortable with being a mindless servant. You can't put a square peg in a round hole. Yet Master said this confidently, as if he had done it before.

How many maids were in this castle, anyway? Was I part of some male maid prostitution ring? I forced myself to finish my omelet and wash it down, even as questions piled upon questions in my head. Curiosity was bad here.

"Wash these dishes," said Master dismissively. "You know how to do that, right?"

"Yes, Master," I said, and went to the kitchen with the tray. As I scrubbed the dishes and glasses clean in the industrial sink, my mind wandered freely. Who ate dinner here, anyway? Royalty? Master came through the door before I could explore this any further.

"That's fine," he said. "Put them on the sanitizer tray." He then led me out the kitchen door and through a maze of corridors. I supposed this was the ground floor, but it was quite a mess.

Finally we were in a small, dark room. He switched on a light; the room was bare except for a drain in the middle. I wondered absently why there was a drain in a spare room. "Sit down, maid," he said. I did so.

"Take off your panties and stroke yourself."

Oh God. I pulled down my lace panties and fondled my tiny dick. My heart was still thumping; I wasn't prepared for this. I closed my eyes again and tried to think of something, but all I could think of was the awful blowjob from yesterday.

"What are you thinking about, maid?"

"Your cock, Master."

Pause. "Are you ready to come, maid?" I heard Master say.

"Yes, Master," I lied, not thinking.

"Then come!"

I gripped my dick hard but nothing was going to happen. Master could tell, and I knew it. I felt ashamed.

"One! Two!"

This was bad. Oh God. I jerked my hand up and down, helplessly.

"Three!"

There was a ZAP and my world went white with pain.


3


"AAAAAAAAARRRGGHHHHH!"

The pain shot all through my body. I felt like every wire in my nervous system was about to snap. It was gone in half a second, but I crumpled on the ground, gagging and tearing up. I could have bitten my tongue off.

"Never lie to me, maid," said Master. "I never lie to you. You are to treat me with trust." He got up. I checked to make sure my arms were working; I slowly sat up again, and he walked to the corner of the room. "Your training will start now."

He switched off the light. I heard the scuffling of feet. The room's atmosphere seemed to change, but I couldn't see anything.

"Keep yourself ready to come on command," said Master's voice. "You will let these men do whatever they want to you." I dropped my hand to my crotch again, my head still throbbing too hard to understand what he meant. Then he said "go," and immediately I was pounced upon and devoured.

I felt five or six men rubbing up against me. One of them unzipped his pants and shoved his cock into my mouth; another took my hand and stuck it down his pants. I started licking the cock in my mouth, and fondling the one in my hand, while still keeping myself erect. Too much was happening at once. I started to zone out, entered the weird realm of utter mindlessness. I closed my eyes and breathed in deep through my nose, even as it was scraped with pubic hair.

Then I felt a cold hand moving up my thigh. I was shoved around, and I felt a bulge underneath my ass. Oh God, no. He wedged his cock, already erect, into my butt cheeks. He felt an opening. No ... not there...

"Mmmmf!" I cried, my mouth still full. Tears welled up in my eyes. He thrusted inside me, and involuntarily I came. Even as my hand left my dick another man was taking it and giving me his own cock to hold. The man pushing his cock into my mouth pushed forward and rubbed my entire face into his chest. I felt someone grab my feet and press them against his growing cock. There wasn't a limb in my body unused. I was utterly and entirely taken care of.

It felt like it went on for days. I could barely breathe. There was the constant grunting, shifting of bodies on top of me and below me. From time to time squirts of sticky cum would splatter on my buttocks, my face. I didn't know how many men were in the room. I didn't hear a single voice.

Finally, from the corner of the room, Master shouted, "Come, maid!"

I dropped my hand from some stranger's cock and jacked off for half a second. But I hardly needed any pressure to come-- nobody had touched my cock this entire time and some man was inside of me. I gasped and convulsed, and my own semen hit me in my face. Then I blacked out.

It couldn't have been five seconds later when I came to but the men were already leaving. The room was dark-- I didn't know if Master was still inside. I tried to sit up, but my ass hurt badly, and I was exhausted. I collapsed on the ground.

I dragged myself to the corner of the room and started to spit. My mouth and throat were caked. My hair, that had been so beautifully smooth when I woke up, was sticky and clumped. The biggest towel in the world couldn't have dried me off-- my maid costume had cum in all of its folds.

I wanted something, anything to call my own. Even my own name would have been an improvement on this. But I couldn't change the fact I was just 'maid', and everything else was forbidden to me. I was a receptacle, a pile of flesh that Master was trying to mold into something.

I smeared my sticky hand on the wall. I wished I knew what this would make me into.

The light came on, and Master was standing in the doorway with a sponge and a bucket of water.

"Clean this room now," he said. "You will clean yourself later."

I took the sponge and looked to see if he would go, but no, he was going to stand there watching me. I couldn't let him see me cry. I scrubbed down the floor, pushed everything into the drain in the middle of the room. I soaked the sponge again and started on the walls. My maid outfit was disgusting. I was disgusting.

Master turned and walked out the door. "Stay here and finish up," he said. As soon as he was gone I collapsed again. Everything ached.

He returned ten minutes later (the walls barely done) with food and water. The food seemed to be someone's first attempt at dinner. I ate it furiously. How many maids were in this castle? How many other people were being forced to go through what I was doing?

I did not have any energy to rebel. I knew the consequences.

Master returned and took me back to my bedroom. "I'm not expecting you to enjoy this," he said. "I'm expecting you to learn what you really want."


4


It had been weeks since it began. I had known nothing but my strict schedule-- breakfast, fucking, and dinner. At some point Master had given me rewards: I was given a padded bra and earrings, and of course forced to wear both of these and jack off while looking at a mirror. I was given perfume, which I was thankfully not forced to use, but I put it on anyway because it smelled better than cum. I was at one point allowed to wash my sticky and stained dress, although he had to watch me, and I still had to wear it in bed. My mind was utterly eroded. My cock was raw from jerking off, although I was the only one who ever touched it. But for some reason, I still felt all the humiliation, all the pain of every punishment. There was some tiny part of me that refused to give in.

 
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