Roommate Got My Ey

Note: It seems like people didn't quite like the story as much as I'd hoped, particularly the second part. I'm ending it with the third part (Of course, I'll write more if people like this!) here that hopefully you guys would like.

Thanks to all who read it, and the supportive comments!

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"Yes, Master."

Two words that forever changed the world. Fantasy and reality had crossed paths, and like the images on my phone I watched with rapt attention, I was on my knees with a chastity cage.

He knelt down beside me and spoke just beside my ear.

"Did you think this was an 'accident'?"

The way he said it, with a sultry whisper that was still dominant, sent a chill down my spine.

"I found out about your little fetish ages ago. I've been preparing and waiting for my chance. I knew you wouldn't be able to pass up this opportunity. Now, get ready for bed. Don't you have an early morning tomorrow?"

He jingled my keys in my ear as he got up, and walked away. He stopped at his doorway and looked back at me with a devilish smile. He held up my keys once again, then disappeared into his room, closing the door behind him.

I must have sat there for a good ten minutes before I got up. He was right, I did have an early morning. But sleep? Good luck finding that tonight! The events of this night left me in shock, and I was processing what happened.

The next day passed in a haze. I was no stranger to going to work wearing my cage, so it wasn't really a problem. I wanted to avoid him for a while, so I got up early and left before he woke up. It was hard for me to pay attention to anything, as inevitably, my head was still spinning. I was anxious to go home at the end of the day, and I contemplated going somewhere else for a bit. But in the end, I decided against it. After all, he did have my keys! Not having them did limit my options.

I unlocked the door with trembling hands and peeked inside. The lights were off, and it was all quiet, which meant he wasn't home yet. I was relieved for the moment and I went inside and locked the door. I turned on the lights, and there, in the middle of the room, a package lay on the table.

I walked up to the coffee table and picked up the plain white box that had a note attached at the top. I plucked the note and started reading it.

"Hello, my little slave. Found it difficult to concentrate all day, didn't you? Well, don't worry, I have a treat for you. Make sure I find you wearing that, and only that, when I come into the house.

Don't disobey your master."

I was taken aback. His display of dominance was startling enough, but it was disconcerting to see him step into the role of a keyholder/domme with such ease. I put the letter down and opened the box, which wasn't sealed. Inside was a collar and leash, and panties. I recognized them as mine, which meant he had gone through my 'kink' drawer full of adult toys and clothes.

Just as I'd experienced at every step so far, I was nervous and unsure of whether to take the plunge. It seemed like things were getting out of hand. A couple of days ago, I was a simple chastity enthusiast who locked himself up for small periods of time and fantasized about having a keyholder. But now that I did have a keyholder, it felt much more overwhelming than I'd thought.

He was my keyholder, though, and I'd promised to give it 48 hours, at the very least.

And so, once I'd showered and dried off, I put on my pink panties and put the collar on my neck. I just sat on my bed, waiting, until he came home. I heard him close the door and walk up to my room. He stopped just outside my door, and slowly pushed it open. He smiled when he saw me, the same smile he had used last night. Without saying a word, he walked on to his room and closed the door.

I wasn't sure what I was expecting, but this wasn't it. When he looked at me, I felt his gaze and I felt the tightness as my dick strained against its captor. He left me in a state of uncertainty, though. Should I get dressed, or should I just carry on like this? Would I have to wait for him to tell me something? Was he going to do something?

In the end, I carried on dressed just as I was. I was doing what I do every day, cooking dinner, and completing my tasks, but I'm not usually wearing panties and a collar while doing it. Well, not *just* panties and a collar anyway! I only saw him once more that night, and he didn't even look at me. He went into the kitchen, took something, and went right back into his room.

The next morning, it was the same. I put my 'dress' from last evening back in the box, got ready for work, and left before he woke up. The entire day passed very quickly, as I kept thinking about what would be in store for me today.

Just as soon, as the time came for me to return home and once again, he wasn't there when I came in. There was, as I expected another box on the table, and this too had a letter on top of it.

"Well done. You followed my instructions exactly, and even though I didn't tell you to keep wearing that all night, you did keep it on. Extra points for that.

What do you know, 48 hours are almost up. We should do something special, shouldn't we? I have a few more things for you today. I'll be back much sooner today, and I want you to wait in front of the door wearing it all, on your knees.

If this is the end of our little arrangement, then we should at least go out with a bang! But I've got a feeling that we're just starting..."

I shivered when I read the last line. I looked at the box and decided I would only look after freshening up. I took a bath, dried up, and looked at myself in the mirror. I'd kept myself in pretty good shape, although I wasn't quite as toned as I wanted to be. The highlight of my naked body was the little pink cage now, though. You certainly couldn't miss it.

I didn't bother to put anything on as I walked to the table, as I knew everything was inside already. I opened the box and emptied its contents on the carpet. There were enough moments over the last two days when I was 'surprised', but that didn't stop me from being so again. There was a furry butt plug tail, the collar and leash from yesterday, and a ball gag. There were also a pair of handcuffs, although I wasn't sure I could put those on. There was also a bottle of lube that I picked up.

I lay down on the carpet and began applying the lube to my asshole. Once it was lubed up enough, I slid the plug down. I'd used butt lugs before, but never this kind. I flexed a bit, getting used to the feel. I got up and went to the mirror in my room. It felt a little weird, looking at myself with a furry pink tail poking out of my ass. I went back to the living room and put on the collar, and attached the leash. Next was the ball gag. I put it in my mouth and locked it behind my neck. Again, I moved the facial muscles a bit to get adjusted to it. I took the handcuffs and went towards the door. I picked my spot -- far enough away from the door so it wouldn't hit me when it opened, and at a slight angle so anyone walking past when he opened the door wouldn't immediately see me in my full glory.

I pulled the rug from in front of the sofa and placed it on the spot. I kneeled on it, facing the door. Then, I put my right hand into the handcuff and locked it. I put both hands behind me after studying the locking mechanism and locked my left wrist into it as well. There was no going back now. I was locked here, helpless, until he came back and unlocked me -- *if* he unlocked me.

It must have been about 20 minutes, but it felt like a whole hour before he came home. He opened the door and looked around. When he spotted him, he gave that smile of his again, and came in, closing the door behind him.

He walked up to me and kneeled before me. He turned his neck to see if I had locked my hands into the handcuffs. The confirmation that I had, indeed, seemed to satisfy him.

"Even the handcuffs? Incredible. You continue to impress me, my friend. You're quite the textbook submissive it seems. Just a few words on a page and here you are, all decked up for me. Of course, we must not forget the contribution of this."

He held up the key to my chastity cage. There was, however, only one key now, instead of two. My eyes grew wide and my brow furrowed as I tried to ask him through my gag where the second key was.

"Worried about the other key, are you? Don't worry, it is in safe hands."

Safe hands? Whose hands was he talking about? Did he give it to somebody else? Panic hit me hard at that point, and I struggled, trying to break free of my shackles. I regretted putting those handcuffs on right now. Meanwhile, he had already gotten up and walked into the kitchen. I could hear his voice, a little fainter, but still clear.

"Oh, I forgot to tell you, we're going to have a guest here today. Remember that cute girl from down the hall you've been trying to ask out for some time? Well, I invited her over for dinner!"

Oh no. 'Safe hands'. He gave her the key, didn't he! For the last couple of months, I'd been trying to ask her out. She lived right down the hall, and I saw her from time to time in the hallway. We'd gone out a few times, but as 'friends', and there was no indication of a date. But I figured that if I'd asked her out after she was comfortable around me, things might go better.

All that was thrown out the door at this moment. If she saw me like this, all hope I had of making her my girlfriend would disappear. She would not look at me the same way again.

I didn't even have enough time to panic before the doorbell rang. He walked up the door without looking at me and opened the door.

"Ah! Our guest of honor is here", he said with a smile. And in she walked. She looked just as cute as ever. She was wearing a short black skirt, and one of the loose white t-shirts she loved so much. She walked in and saw me almost instantly. For a while, her eyes were fixed on me, as if she was studying me. My roommate interjected.

"Now, now, there's enough time for staring, but if you're gonna do it, do it properly."

He locked the door and came up to me. "Stand up", was all he said.

Nervously, I stood up. I almost fell down, as my knees fell weak, but I managed to not retain a little bit of dignity there. He picked up my leash and tugged on it as he began walking. I kept my eyes down as I didn't want to meet hers, and followed him as he led me on my leash. He pushed the coffee table aside and looked at me.

"Stand here."

I obeyed him and stood where he was pointing at.

"Now you can see *all* of him."

I looked up ever so slightly and found her eyes on my chastity cage. This was a topic I was leaving for much, much later. My hope was, that once she'd agreed to be my girlfriend and we'd spent some time in a relationship, I'd bring up chastity as one of my kinks. But now, we'd skipped a few steps and come straight to it. I closed my eyes, and just stood still. Hell, if a good look is what she wanted, then let her have it. This isn't what I had planned for her, but it wasn't like I had much of a choice.

"Wow, this is something."

She spoke for the first time, and I opened my eyes to see a slight smile had crept on her face.

"Isn't it? I told you he was submissive. You wouldn't believe me, but here he is now, all ready for you."

Her smile grew as she walked up to me. She put her hand up to my face, running it against my cheeks. Her touch was enough to arouse me and my cage tightened. She brought her hand to my chin, and suddenly, she held my face in her hand a little roughly. At the same time, her other hand went to my cage. My already straining member went mad, and I felt a tightness that I'd never felt before.

"Oh, you are perfect. Already straining in your cage, are you? Oh, we are going to have so much fun! I wasn't sure if you were submissive or not, but I was confident that I'd be able to turn you into one. All I was waiting for is for you to finally ask me out. Well, your friend here did the job for you, and in fact for me too. What a treat this is!"

Wait, she wanted me to ask her out? This was all new. It was like the two of them had been planning something behind my back that I had no idea about! And to top all of that, she's a domme? This cannot be real.

She let go of me and turned to my roommate.

"Thank you for getting him ready. Now if you don't mind, I'll take over. Of course, you're welcome to use him too..."

He walked up to me, and just like her, he grabbed my cage and balls.

"Oh, don't worry, I'll use him all right. I'm his master alright, and I can see it in his eyes, the desire for submission. Now go on with the girl of your dreams as her little slave. But don't forget about me, I'll have my turn soon..."

He let go of my cage, but his rough touch left a bit of pain in my balls and I winced. He took the end of the leash and handed it to her. She took it and began walking towards the door. I felt the tug and started following her. I panicked when she went to the front door. Was she about to lead me into the hallway!?

My fears were right, as she opened the door and walked nonchalantly into the corridor. The lights were dim, and it was empty for now. I followed on, keeping up pace with her as best as I could. I kept my eyes down, determined not to look at the doors and wonder if they were witnessing my humiliation. She reached her door and fumbled for a few seconds to find her door.

"There it is! The damn key always keeps getting lost. I'm a little scatterbrained when it comes to keys.."

She gave a most wicked smile as she said that and opened the door. I followed her into a place I had been to many times before. But this time, as the door closed behind me, I had no idea what was going to happen. She came back in front of me and picked up the leash again, and led me to her bedroom. I'd been here before. In fact, I was here earlier this week, when we lay on her bed and watched a movie. I hoped to come back as her boyfriend, but I'm here as her slave.

She let go of the leash and reached for the hook of my gag. She slowly unhooked it and took off the gag. She put it on the bed and sat down beside it.

"There are two rules here. First, you must address me as Mistress. Second, you must do everything exactly as I tell you. Is that clear enough?"

I nodded silently in agreement.

She got up and came up to me, roughly holding my face in her hand. Her aggression forced me back a couple of steps before I stabilized myself.

"I asked, is that clear?"

"Yes... yes, Mistress", I muttered.

She let go of me, and said, "Good."

"Now, I will give you a choice. I'll unlock you and I'll give you the greatest fuck of your life, but you'll be locked up for four months straight after. I might release you whenever I feel like it, or if he asks me, but your hands will be locked and there will only be ruined orgasms. Or, I tease you all night and lock you back up, and you'll get to jerk off once a month. Which one do you choose?"

I was absolutely dumbstruck at his point. It was happening. I didn't just have one keyholder, I had two. And this woman, who I'd been mesmerized by for so long, was going to be my mistress. The two choices she had laid out for me were incredible, but despite the long lockup, my choice was clear.

"The first one, mistress."

She smiled as she walked up to her bedside drawer and pulled something out. It was the key to my chastity cage. She walked over seductively and ran the key across my chest before moving towards my cage. She unlocked and took off the padlock, and my cock almost sprang out at her.

"Well, someone's excited..."

She removed the cage and the ring and kept them on the table. Then, from the drawer, emerged one of the biggest strap-ons I'd ever seen. It was certainly bigger than the one I had. She took off her skirt and her tee. Underneath, she had on a sexy lace lingerie set. My cage was off, but it still felt like my cock was straining to get bigger and bigger.

"I said I'd give you a great fuck, I didn't tell you how."

I'd been putting butt plugs up my ass for some time, but I was about to get fucked up my ass for the first time. She took out a bottle of lube and applied it generously to the dildo. She strapped it on and rubbed the lube on it while keeping her eyes fixed on me. She came up behind me and pushed me down so I was bent over the bed. She put some lube around the butt plug and pulled it slowly. Some more lube was put in, and then she began sliding in. One leg came up to the bed, right beside me. Slowly, I felt the strap-on go inside, reaching new depths I'd never experienced before.

As it went in completely, I experienced a sensation I'd never felt before. She reached around with her hand and wrapped her fingers around my incredibly hard cock.

"Well, glad to see you're enjoying it", she spoke into my ear. Her hand on my cock only heightened the feeling, and she began thrusting in and out of my asshole slowly. She began picking up the pace, and her hand began stroking my penis. Precum was oozing out for a long time, but after being locked for two days and being unable to jerk off after all this excitement, I knew I was going to explode very soon.

Just as I felt myself getting closer, though, she stopped thrusting, as if she realized I was about to cum. She pulled out completely and took her hands off my cock.

"Not so fast...", she whispered in my ear. My hands were still handcuffed, and she pulled them up. She took out another contraption from her drawer of mysteries and attached my hands to her bed frame. My hands were now suspended above my head, with no way of moving them. She also attached cuffs to my ankles and connected them to the bed stands. She took the gag that was lying on the bed in front of me, and fit it back into my mouth.

From her drawer, emerged a black riding crop. She lightly ran it all over my body, creating a tickling sensation that I was unable to do anything about. And then, smack! She landed the crop right on my ass, and my cried out a muffled shriek through the gag. My ass stung with pain, and I hadn't had enough time to process the pain before it came down again with another stinging smack. On the third time, there were some tears in my eyes. My first experience with smacking was turning out to be more intense than I'd imagined.

After two more smacks, she put the crop down, and then ran her finger over my ass. She'd put on latex gloves, and the cold material only caused it to sting more. I flinched as she touched me, and all I heard was her laugh. She put some more lube and inserted the dildo back into my asshole. She didn't take quite as long this time before she began thrusting fast. Her hand began stroking my cock, and I couldn't take it for long.

It was the best and the longest orgasm I'd ever had.