My Roommate's Maid Pt. 06

The new rules were harder to follow than I first thought.

I walked back to my room, deliriously horny.

It had been five weeks since I lost the bet and became my roommate's maid. Since then, I was completely at the whims of the three boys I lived with. I began wearing a French maid dress for all of my chores. Then I was no longer allowed to wear boy's clothes at all. I even willingly let my roommate Tomas dominate me.

He gave me eight rules to live by. At the moment though, I only cared about one.

I was no longer allowed to masturbate. Tomas decided when I came.

It had been three days since I last orgasmed. Before the bet, I masturbated almost every day. It was a bad habit but one I was certain I could break. When Tomas first gave me the rules, I thought I could handle orgasming a little less often.

And maybe I could have handled it. That is, if I wasn't subjected to sexual energy multiple times a day.

Whenever Tomas wanted, I had to give him a handjob or blowjob. The same was true for my other roommates Antonio and Marshall.

It was ridiculous. How was I expected to keep from touching myself when I was making other men cum at least three times a day??

What happened yesterday made it even worse. Tomas had given me a buttplug to wear. I could feel it constantly inside of me, rubbing against my g-spot and driving me crazy. To top it all off, Antonio had noticed my plug.

Then he fucked me.

God, it felt so good! I wanted nothing more than to be filled up by him again.

Slowly, my fingers crept towards my skirt. I knew it was against the rules. But they were rather arbitrary anyway. Tomas didn't know how horny I was. I'm sure this time can be an exception.

My dick was still hard. I pulled up my skirt and slid down my g-string. Even this slight touch of my fingers made me shiver and my dick leak precum. I rubbed my stockinged legs together over my sheets. I caressed my hips.

Then I began to lightly stroke my shaft as I cupped my balls. I gasped softly as I moved my hand up and down.

I came quicker than I expected. Sticky liquid exploded onto my stomach and I shivered in post-orgasmic bliss.

I laid there for a few moments, breathing heavily before I got back up. I cleaned myself up, changed into a pink nightie and mauve boyshorts, and got ready for bed.

I was trying not to think of the rule I'd broken when Tomas showed up at my door.

"Hey," he said.

I jumped. "Hey Tomas! I mean, Master?"

"I figured it's been a while if you wanted to cum," he said, not breaking eye contact with me.

My cheeks flushed. I reflexively moved my hands to cover myself.

At first, I thought about lying. But then I paused for too long and couldn't think of what exactly to say. So, I just told the truth.

"I... uh, just did."

His expression was unchanged.

"I'm sorry, I just... I don't know. I didn't think you'd find out."

Why am I apologizing for jerking off? a small voice inside of me thought. This is like the most basic thing to do as a guy.

"Follow me," he said.

Tomas left the doorframe. Nervously, I went after him in just my nightie and panties.

I walked into Tomas' room and found him seated on the bed.

"Are you serious about this?" he asked. When I didn't answer immediately, he added, "About being a sissy?"

I could feel myself blushing now.

"Yes."

"Yes what?"

"Yes, Daddy."

"And you're serious about following my rules, whatever they may be?" he asked.

"Yes, Daddy."

"Then come here and lie down."

His gaze told me he was not joking. I gulped and moved towards him. My breathing quickened.

As I approached him, Tomas put a hand on my back and gently guided me down onto his lap. It was a position I'd never assumed before. My stomach was across his legs, with my arms dangling in front and my legs behind.

He pulled my nightie up and groped my right ass cheek. Tomas moved his fingers into the waistband of my panties and pulled them down to my thighs.

I kept my gaze straight ahead. My dick hardened slightly from the exposure.

"I want you to count them off," he commanded.

Then came a firm spank across my right ass cheek. I yelped and squirmed on his lap.

"Count it off."

"Wuh-one," I managed, breathing heavily.

Tomas spanked my left cheek now. It wasn't as bad when I knew it was coming. His slaps were hard but stopped short of sadism.

"Two."

Spank.

"Three."

Spank.

"Four."

Spank.

"Fi-ive."

Occasionally, Tomas slapped the same cheek twice in a row. I spasmed from the unexpected pain.

"Six. Seven. Eight. Nine. Ten," I counted.

At last, he stopped. Instead of another slap, Tomas grabbed my ass and gently massaged it. It still stung a little but his touch felt mostly good now.

Tomas pulled my boyshorts up and smoothed down my nightie.

"What do you say?"

I was still on his lap, shaking slightly.

"Thank you... thank you, master."

"Of course, Sophie. I'll always be willing to discipline you when you need it."

Tomas lifted his hands off of me and I warily got back on my feet. I stood in front of him, feeling ironically more exposed now than when he was slapping my bare ass.

My sheer pink nightie stopped at the top of my thighs. Beneath the hem of the nightie, my legs were perfectly uncovered and smooth. You could see the outline of my half-hard cock in my panties.

Tomas eyed me up and down. His gaze was intense and discerning in a way I had never seen from anyone else.

I shrank from his stare. My cheeks went red, now matching the color of my freshly spanked ass.

"Come back here first thing in the morning," Tomas commanded.

"Of course, Daddy," I replied, "Should I wear anything specific?"

"No need," he said offhandedly, "You'll be taking it all off first thing when you enter."

I shivered and said goodnight to Tomas. I went back to my room and tried to go to sleep. My dreams were filled with all the lewd possibilities of what he was going to do to me.

XXX

The next morning, I immediately went to my dresser to get changed. Most of Antonio's girlfriend's clothes were not lingerie and I had my pick of 'normal' options. I put on a simple women's T-shirt and short shorts over some heather gray panties.

I got ready in the bathroom and put on some light makeup. Then, I went next door to Tomas.

He was already awake, though clearly still a little sleepy. He yawned and waved me in.

"Close the door," he said.

I did so and presented myself before him, my hands clasped at my front.

"Strip naked, Sophie," Tomas said, "And fold your clothes in a pile after."

"Yes, daddy."

I pulled my t-shirt over my head and then dropped my shorts and panties in one motion. I precisely folded my clothes and placed my shirt, then shorts, then panties in a stack by the door.

While I was doing that, Tomas was rifling through a small box of his. He took a few items out of it.

"I don't want you to think of this as a punishment," he said, "That's what the spanking was for. This is an opportunity to change your mentality."

Tomas waved for me to come closer. Completely naked, I moved towards him.

Tomas kept meticulous eye contact with me as he spoke, like he was trying to dominate me with his eyes. "It should have been clear after the initial bet. The rest of us have dicks. You don't. The rest of us are men. You are not.

"Of course," he continued, "That's easier to say than to truly believe. I don't blame you for still wanting to masturbate, for still thinking you're a man."

I was frozen there. Something about Tomas' confidence and the way he spoke so definitively about my inner nature transfixed me.

"I want you to repeat after me," he said.

"Yes, sir."

"I don't have a cock."

I gulped. Whether or not I believed it, I said, "I don't have a cock."

"I have a sissy clit."

"I have a sissy clit." What am I saying? What is this?

"My purpose is to please men."

"My purpose is to please men."

"I don't deserve responsibility for my own pleasure."

Finally, I said, "I don't deserve responsibility for my own pleasure."

I felt a strange rush saying these things, simultaneously humiliated and exposed while also being incredibly turned on. My dick twitched a little but didn't become hard. I could try to deny it, but I loved the fact that Tomas was in control of me.

I finally got a good look at the items Tomas had taken from his box. There was a circular metal ring, a long elastic band, and a two-inch long, metal-ribbed cage. I had no idea what to make of them.

"This is a chastity cage," Tomas said, holding it out to me, "It'll stop you from masturbating when I don't allow you to."

I blinked. Is this supposed to go around my... Surely not.

"Ask me to cage you," Tomas said. He kept his eyes on me.

I didn't respond right away but Tomas was unwavering.

"S-sir, could you please cage me?"

"What should I cage, Sophie?"

"My dick, er, I mean my clit."

Tomas smiled deviously at me. "Of course, Sophie. I'd be happy to help. Now, stay still."

Tomas then gently cupped my balls. I flinched at first. He had never touched me like that before. Our relationship had always been very one-sided.

Tomas placed the cool metal ring against my balls. It felt good. Methodically, he moved my balls and then soft cock through until the ring was snug at the base of my penis. I kept my hands at my sides the whole time.

Tomas then connected the elastic band at one side of the metal ring, brought it around the back of my waist, and attached it to the other side. This pulled the ring tight against my body and kept it in place.

Finally, Tomas placed the actual cage at the tip of my cock. It became a little hard and he had to gently apply pressure to get it soft again. As he pushed down, my soft cock came to fill out the confines of the cage. Tomas then connected the cage to the ring. Holding it there, he produced a small padlock and firmly locked the two metal pieces together.

He let go. My dick twitched from the first attention it had gotten from another person since the beginning of quarantine.

Unfortunately, I imagined that's all the attention it would be getting.

"Try wearing it all of today for a start," Tomas said, "Let me know if it starts pinching or hurts at any point."

"Yes, daddy."

"From now on, for most parts of the day, you will be locked up and plugged. Got it?"

"Yes, daddy."

"Go back to your room, put your plug in, and change into one of your maid dresses. Then meet me in the living room."

I went to curtsy but remembered I was completely naked. Embarrassed, my dick stiffened and quickly came up against the edge of the cage.

It was a weird feeling. My body wanted to get hard but my actual cock couldn't. It was limited to less than half its full length.

It felt uncomfortable for sure, but oddly arousing too. Which only made my stifled erection that much worse.

Tomas smirked. "Don't worry, your little clit will get used to it. It'll have to."

I blushed and began putting my clothes back on. The panties felt good as I brought them up my smooth legs. The soft fabric slid effortlessly over my newly caged cock and balls. It hugged them tightly and I shivered in a rush of denied pleasure.

I put my shirt and shorts on and left for my bedroom. Once there, I immediately stripped again.

This cage is going to be annoying if I keep getting erections every time I change, I thought.

The plug didn't make it any better. I took out my black buttplug with a flared base, applied a generous amount of lube, and slowly worked it into my ass. As I did so, my dick hardened and pressed up against the end of the cage.

I started to change into one of my maid uniforms. I started with white lace panties and white lace bikini bra. Then, I secured a garter belt around my waist and pulled lace-top white fishnets up my legs. I decided on my fanciest maid dress today, one of the costumes Tomas purchased for me. It was black with a white apron at the front, had a scalloped collar that went up to the middle of my neck, and long, sheer black sleeves. A frilly petticoat filled out its skirt.

Of course, my cock refused to soften during all of this.

Afterwards, I went to the bathroom and put on more makeup. I touched up my foundation, added lipgloss, light red eyeshadow, winged eyeliner, and mascara. I left for the living room.

XXX

Tomas, Antonio, and Marshall were all waiting for me.

My heart beat like a drum as I approached. I moved my fishnetted feet in small precise steps, walking as daintily as possible. I was highly aware of the plug inside me, as well as my caged cock. The cage stayed fixed to my body as I moved. The feeling of lacy panties on top of it and my petticoats swishing back and forth enraged it.

I knew I was blushing. The gaze of my three masters all fell on me.

Tomas patted the armrest of his chair. His expression was equal parts elated and mischievous.

I stood next to him, facing towards Antonio and Marshall, my hands clasped in front of me.

Tomas absentmindedly ran a hand up my leg. My whole body shivered.

"Take off your panties, Sophie," he said. There was a glint in his eye as he looked up at me.

I hesitated. I could not bear to make eye contact with anyone.

"It's not anything we haven't all already seen," Tomas said.

I gripped the hem of my maid dress tightly.

"She doesn't have to do it if she doesn't want to," Antonio said.

"No, I'll do it," I said.

I saw Marshall's face light up with a smile. He pulled out his phone camera.

Gingerly, I lifted the skirt of my maid dress and held up the petticoats underneath. I put my fingers into the waistband of my lacy white panties and deliberately slid them down my legs. I could not keep from shaking. I brought them down to my ankles and then stepped out of them.

"Put your panties into your mouth," Tomas commanded. He kept running his hand up the side of my leg.

I did as I was told, bending down, grabbing the panties, and stuffing them into my mouth. I imagine I looked like I was pouting with them in there.

"Now lift up your skirt and show everyone."

Again, I gripped my petticoats and pulled them to my stomach.

Marshall and Antonio both leaned forward to get a better look. Marshall excitedly took a few pictures with his phone.

Beneath my frilly petticoats was my bare cock, locked up tightly in a chastity cage.

Tomas moved his hand over and gently cupped my balls. I immediately shivered in pleasure at his touch. My moan was stifled by the panties in my mouth.

"As you can see," Tomas said, softly playing with my balls, "I've decided to cage Sophie for her own good. She won't be able to masturbate unless we let her."

"Fuck that's so hot," Marshall said.

"Didn't you think this was 'gay as hell' a week ago?" Antonio said.

"I've... changed my mind," said Marshall, still taking pictures with his phone.

Tomas continued, "From now on, Sophie doesn't have a cock. She has a caged little clit. If she refers to it as anything else, feel free to punish her."

Tomas gazed up at me, smiling as he still held my balls in his grasp. I didn't dare look back at him. It took everything I had to not moan audibly.

He took his hand off of me.

"Sophie, how about you go without panties for the rest of today. I want everyone to have full access to your little clitty."

I nodded my head. My breathing was a little choked from excitement.

Antonio stood up with a grunt. "I have some more laundry today for you." He spoke like I hadn't just been exposed before him.

Marshall stood up too. "And I have a gaming session in an hour." He winked at me.

Tomas brought a hand into my skirt again and grabbed my ass. "After you're done with them, come and see me."

I nodded, unable to speak with the panties in my mouth.

After that, the impromptu roommate meeting was finished.

XXX

It took a while for the embarrassment to truly set in. It was unreal in the moment, having my locked cock, I mean clit, paraded before all of my roommates at once. It was only in the mundane moments afterwards, attending class on Zoom, picking up Antonio's laundry, wiping down countertops, when I understood the gravity of what happened.

There had been many turning points in the month since I lost the bet.

Agreeing to wear a maid's dress. Letting Marshall take photos of me. Sucking Antonio's cock. Submitting to Tomas.

This was only one more.

But it felt far more critical than any of the others. As foolish as it was in retrospect, I truly felt I could have backed out at any time.

Now, this was no longer serving my roommates in the privacy of their rooms. This was no longer dressing up or just kinky roleplay. I had willingly stripped before all of them. Now, I was wearing a chastity cage and a butt plug all day.

I saw no way to undo this.

Nor did I want to.

Marshall had me pick up his trash off the floor, wipe down his desk, and vacuum. While I was doing that, he opened up discord and uploaded pictures of my chastity to the #photos channel.

Immediately, congratulatory and degrading messages came rushing in from the other horny men in the server.

Marshall beckoned me over. "Look at the reaction you're getting."

I read over the messages:

> Soooo hot.

> Good girls stay locked up.

> What a pathetic beta

> How long you gonna keep her caged?

> Cage is too big tbh. When she getting downsized

> If I were @Sir-Marshall, she'd never be unlocked

> You should def do a size comparison with her now

"Well how about it?" Marshall said, "You wanna do a comparison?"

I nodded and tried not to blush. "Yes, master."

Marshall took out his phone again. He put a finger into the waistband of his basketball shorts and boxers and slid them down. His half-hard cock flopped out.

He motioned for me to lift up my skirt. I did so.

"Now rub my cock."

Holding my skirt with one hand, I reached down and gripped Marshall's shaft. I diligently worked my hand up and down. His cock hardened and reached its full seven inches.

Marshall grabbed my butt and guided me closer. He then swiveled towards me in his gamer chair. I used both my hands to hold up my skirt.

The tip of Marshall's veiny cock pressed against my thigh. Right next to it, my two-inch caged clit twitched in arousal.

"And I thought you were small to begin with," he said.

His camera clicked three times as he took photos of our cocks next to each other.

"You know what to do now." Marshall pointed down to his lap.

"Yes, master," I said.

I got down onto my knees and crawled under his desk. Marshall slid his boxers and shorts down to his ankles and scooted in towards his computer. I then cupped his balls and started stroking his shaft.

"Do you think I should post the photo of your clit next to my cock?" Marshall asked, looking down at me underneath his desk.

"Yes sir, please post the photo," I said, still rubbing his cock.

"If you insist."

He smiled and quickly uploaded the photo to discord. I heard notifications ping on his phone, no doubt more demeaning messages and lewd suggestions.

I put my glossy lips over the head of his dick and kept stroking him. I played with his balls and enjoyed the grunts of pleasure coming from above me. Interspersed with his moans were the clacking of his keyboard and music from some strategy game.

I stayed down there, bobbing and sucking on his cock. My own caged clit stayed neglected. It was soft in its cool metal confines.

It took a while but I could feel the orgasm building in Marshall's dick. When he was almost there, he pulled me off of his cock.