My Roommate's Maid Pt. 02

Things didn't escalate immediately after Marshall's joke. I kind of laughed it off, finished cleaning, and left. For a few days, we didn't speak of it.

But I was acutely aware of the pictures he had of me now.

How could he do that? I was cleaning his room like he asked, wearing the maid dress like Tomas asked, and then there was that awful click. Followed by more.

Would he send them to anyone? Were they just for him? I didn't like any of the options.

I kept on cleaning though, holding up my side of the agreement. Free rent over the summer was worth it. That's what I told myself at least. The truth is that I had a misplaced sense of obligation, a feeling like I couldn't let my roommates down. This was ridiculous of course. I didn't owe them anything. Yet I kept cleaning.

I didn't wear the maid costume one day but the looks from Tomas were enough to make me put it on again the next.

Since I only had the one uniform, it meant I was doing laundry once every two days. Antonio and Tomas started dropping clothes in my hamper and ordering I wash them. Loading, unloading, and folding laundry was added to my chores.

Laundry was one of the few times in the day when I was wearing boy clothes. For all my other chores, I would be in lace-top fishnets and a maid dress that revealed my ass if I bent over. I avoided this as much as possible, especially if my roommates were around. But while alone, I had to admit I enjoyed it. The clothes felt good on my bare skin, especially the skirt as it swished and moved. I was still happy to be back in boy clothes by the end of the day but I didn't despise the maid situation as much as I thought I would.

Antonio dropped by my room one night as I was already winding down. I was wearing boy clothes by then, a vans t-shirt and some shorts, and had on a facemask. Antonio was carrying a bundle of clothes. I immediately thought this was more laundry for me to do.

"I thought you might appreciate this," he said, placing the clothes on my dorm floor.

I got up from my bed and went over to the pile. Just from looking, I could tell it wasn't Antonio's. He normally wore tanks, shorts, and hoodies.

"What is this?" I asked.

He rubbed awkwardly behind his head. "My girlfriend cycles through clothes really fast. With her being out of state, she told me to just donate these. And I figured you'd want them."

I ran my hands through the pile. It was made up of womens shorts, crop tops, leggings, and even panties, bras, and hosiery.

"I don't know what to do with this." I stepped back.

"Really? I saw the photoshoot you did for Marshall. Plus it was pretty easy for Tomas to convince you to wear the maid dress."

I said nothing and stared at the mass of clothes before me.

Antonio continued, "I'm calling another roommate meeting tomorrow night. Change into something from here for it."

Antonio didn't entertain any negotiation on his commands. He left me to sort through his girlfriend's donated clothes.

The next day I decided to confront Marshall. Unfortunately it was during the day, so I was still in the maid dress.

"Dude, did you share the photos with Antonio?" I asked tersely, trying my best not to look ridiculous in my uniform.

Marshall wheeled around in his chair. There was homework (surprisingly) on one of his monitors and Crusader Kings III on the other.

"I shared them with both Tomas and Antonio," he said, taking a sip from an open soda can on his desk.

"Why?"

My fist was tightly balled. I couldn't understand why he would do this.

"It's not like it's anything they haven't seen. You're in that dress all day. I can add you to the groupchat if you want to see the photos yourself."

I spoke slowly and determinedly, as if that would get the point across. "I don't want to see them. I just don't want you to share them."

"Relax," he said, "They're not leaving this apartment, I promise."

"Oh, and by the way, I heard you started doing Antonio and Tomas' laundry. There's some on the bed if you wouldn't mind." He pointed over at a mess of clothes that he must've been sleeping around or on for the past few nights. "And after you're done with that, vacuum my carpet. Please and thank you."

I grumbled to myself and went over to collect his dirty laundry. Of course he wouldn't use a hamper. I grabbed up his clothes loosely in my arms and went off to wash them.

My schedule for the rest of the day included online class in the afternoon, History of Economic Thought, and then the roommate meeting afterward. I changed out of the maid dress and cast it aside. I'll have to wash it first thing tomorrow, I thought. Remembering Antonio's command, I looked over at the womens clothes he'd given me. I sorted and placed them neatly in one of the empty drawers in my dresser.

At this point, I was aching for anything I could call a win. My mind went into malicious compliance. I picked out the most androgynous clothes from the bunch, a red t-shirt that said 'Hozier' and a pair of short shorts.

Feeling only a little skimpier than normal, I walked to the living room for the roommate meeting. To my surprise, Tomas, Antonio, and Marshall were already there.

I could see Antonio looking at me. I couldn't tell what his expression meant.

"Please, sit down," Tomas said.

I did so. They were all sitting on the couch across from me. It felt weirdly like a job interview.

"You're already staying for the summer, that's decided," Tomas said.

I'm getting some mixed feelings about that.

"There's one more thing," said Tomas.

What could it be this time?

"We think you shouldn't wear boy clothes anymore," he said, "And we think you should incorporate makeup."

"Why would I do that?" I asked, "Isn't cleaning enough?"

"It'd just be nice for this apartment to have a woman's presence," Marshall added.

"But I'm not a woman!"

"I know you're not," said Tomas, "You're something else. You're a maid. And you do as you're told."

He smiled. I blushed and my cock went a little hard in my shorts. I crossed my legs to cover it.

Tomas continued. "And I think you'll do it. For one, you'll do it because you like being told what to do. If I'm wrong, tell me now and you can stop cleaning. We'll go back to normal and say goodbye at the end of the semester."

I stayed silent for a while. I tried to hide my blushing and my half-hard erection.

"...I guess," I finally said, barely audibly.

"I need you to say it," Tomas said, staring directly at me.

"What?"

"Say you're our maid. You'll do whatever we say."

I have no explanation for how or why those words came out of my mouth. But they came nonetheless.

Slightly louder, I said, "I'm your maid. I'll do whatever you say."

Tomas nodded seriously. Marshall stifled a laugh. Antonio placed both hands on his knees and stood up.

"First order," Antonio said, "Put all your boy clothes in a bag. You're not to wear anything from it while living here. During the day, you wear the maid dress. At night, you change into some of the clothes I gave you."

I realized I was slightly shaking now, half from anxiety and half from excitement.

"OK." I nodded my head.

"OK what?"

I tugged at the hem of my short shorts.

"From now, refer to me as sir," Antonio said.

I gulped. "Yes sir."

Antonio smirked and walked out of the living room. As he was going, he looked back and said almost casually, "Remember, you did this to yourself. You agreed to the bet, to the uniform, and now to this."

At that moment, a wave of humiliation washed over me. I couldn't meet the eyes of anyone.

Soon, Tomas and Marshall got off the couch to leave.

"To be clear, I want to be referred to as 'sir' too," said Tomas, "Antonio doesn't get special treatment."

"Me too," Marshall said with a smirk.

I looked up slightly, my eyes about at chest level.

"Yes sir. And yes sir," I said meekly.

From then on, I had three masters.

I slept in the t-shirt and short shorts Antonio had given me. The next day, right after my servitude had been made official, I changed into the maid dress and pulled the fishnets up my legs. The feel of the freshly washed panties drove my cock crazy so I had to carefully tuck it between my legs. With that, I went to Marshall's room to vacuum. I also brought him his newly washed clothes, folded and sorted into underwear, shirts, and bottoms.

Without even greeting me, he pointed to a spot in the carpet.

"Before vacuuming, scrub that out."

Marshall must've spilled the off-brand cola he always drinks next to his desk. I was a little angry about his tone and lack of thanks but I nodded anyway.

"What do you say?" He looked at me, arms crossed.

"Yes sir," I said, averting my gaze sheepishly.

"Good. Now get it done quick. I have class in an hour."

I was surprised Marshall even went to class. He rarely talked about it and when he did, it was mostly to complain about unfair attendance policies.

I went to the kitchen to get cleaning supplies and paper towels, stopping by the closet to pick up the vacuum on my way back.

The cola came out easily enough. Just a lot of rubbing and spraying. I slowly and methodically worked the stain out of the carpet. Behind me, Marshall stood in the doorway and scrolled on his phone.

Next, I started vacuuming. I don't think the carpet had been vacuumed since we moved in so it picked up a lot of dust and other stuff. His room was small so luckily that chore didn't last long.

As I was about to leave, I remembered last night's conversation and how it had cemented my place among the roommates. "I'm your maid. I'll do whatever you say" was echoing through my mind. Why did I say that? Why wasn't I putting up more of a fight? And most horrifying of all, Am I actually enjoying this?

So, anticipating what my new masters would want me to do, I curtsied and said, "Anything else, sir?"

"I like that. Do that more often," Marshall smirked. "And not right now maid, you're excused."

I went about the rest of my daily duties. While I had the vacuum out, I vacuumed the living room. Then I swept and mopped the kitchen and then wiped down the countertop. I did laundry that morning so I was done with chores for the day.

After Tomas had ordered I start wearing makeup, I had ordered some online. Brushes, foundation, concealer, eyeliner, eyeshadow, mascara, lipgloss, and blush were now in the mail. I opened my phone to checked the delivery status.

That's when I saw it.

Notifications from a new groupchat with Antonio, Tomas, and Marshall in it.

I clicked the notifications. The first thing I saw was a video of my backside as I cleaned Marshall's floor. While kneeling, the skirt of the maid dress wasn't hiding anything and my cock was clearly defined in my white lace panties. In the video, I rocked back and forth as I scrubbed the carpet.

My jaw dropped. I didn't know what to say.

The next message after the video was from Tomas. It read, 'Hello Maid. We've added you to this groupchat so you can see what we're posting about you. Also, this will act as a place for us to give you commands and coordinate with each other.'

The next one, again from Tomas, read, 'Keep notifications on. Whatever we say here you have to follow.'

And finally, 'Reply 'yes sir' if you understand.'

I tried not to look down as my cock was growing in my panties. Petrified and slightly turned on, I typed back, 'Yes sir.'

From Tomas: 'Good maid.'

From then, it wasn't necessary for my masters to tell me in person when they needed something done. Single word texts like 'laundry' or 'dishes' or 'dusting' would pop up on my phone and I would promptly rush over to get them done.

Tomas commanded in the chat that I stay completely shaven except for my head. This wasn't really a problem as I was mostly hairless to begin with, but I still followed the order and shaved my underarms and groin daily. My leg and arm hair was so fine and grew slowly enough that I only needed to shave them weekly.

After the makeup arrived, Tomas started sending photos of models and makeup youtubers to the groupchat. 'Start emulating these styles' was the command afterwards.

I had done some makeup in the past (and girlfriends had done some on me too) so I wasn't a complete amateur. Still, it took time before I could draw steady eyeliner or put on even foundation.

It didn't seem to matter much. Even just a little contouring and mascara/eyeliner impressed Tomas and Marshall. The latter exclaimed a long "daaaaamn" when he saw me. Antonio, usually unflappable, said "Looks good" when he saw my new look.

Of course, Marshall started taking photos. I don't know why but I relented when he asked me to pose. I guess I stopped minding.

I mean, they're seeing me like this anyway, I thought. Plus, it felt good to be the center of attention.

A few more days passed and I fell into even more of a routine. I followed all orders. I woke up, attending my early classes on zoom, then changed into my maid dress and put on makeup. Then I spent some of the middle of the day cleaning, breaking for lunch and playing racing games with Tomas, then attended more classes, and later changed into some non-maid clothes for the night.

At this point, it had been just under three weeks since I started as my roommates' maid. This particular night I finished cleaning early, brewed some lemon chamomile tea, and attended my Stats and Econometrics class. I decided to change from my maid uniform into some of Antonio's girlfriend's old clothes I hadn't tried yet. I put on a mauve push-up bra that fit me surprisingly well and coupled it with matching mauve boyshort panties. Finally, some pink stay-up stockings and a sheer, light-pink teddy over top. I still had on winged eyeliner, mascara, foundation, and concealer from earlier. Naturally, I kept my camera off for the class.

I didn't really pay attention though and told myself I'd study the readings a little extra this week. I switched the tab over to Netflix and got ready to watch some Better Call Saul.

There was a knock at the door. It swung open slowly. Apparently I had forgotten to close it.

Standing in the doorframe was Antonio. He was wearing a tight t-shirt that showed off his broad shoulders. He crossed his arms and stared at me.

I looked back at him, meeting his eyes for only a moment before looking down at the floor. I reflexively curled up in my chair, like I was trying to hide from his gaze. At first I thought he was judging me. You're the one who gave me the clothes, dude, I thought, And the one who insisted I wear them all the time!

But I realized his gaze showed something else. Maybe he needed help with a chore.

Antonio beckoned with his fingers. "Come help me with something."

I got up and followed him. The sheer teddy swished as I moved. This is odd, I thought. Sometimes Marshall would ask me to do chores after my shift was done but Tomas and Antonio were usually good about only bothering me during the day.

Antonio led me back to his room, the closest one to the living room. I followed him in and he closed the door behind me.

Without speaking, he folded a throw blanket twice and then dropped it on the floor. He pointed at it.

"Get on your knees."

I blinked at him several times and started to say something. Butterflies rose in my stomach and I shook a little. Antonio didn't say anything and I couldn't bring myself to say anything.

I smoothed out the teddy and gingerly knelt onto the throw blanket. My heart started pounding in my ears.

"You can say 'no' or 'stop' at any time," Antonio said slowly and calmly. He had his hands positioned at his waistband. "You're going to suck my cock, OK?"

I stammered and my face went red. I didn't stand up from the throw blanket.

I could have protested or said 'I don't want to' but I didn't. At that moment, I wasn't even worrying about myself. "What about your girlfriend?" I asked meekly. I couldn't meet his eyes.

"We're poly," he said. He unzipped his pants, showing the fabric of his boxers underneath. "Besides, this is more like masturbation than anything. She's cool with it."

I tugged weakly at the hem of my pink teddy.

Antonio placed a hand on my cheek and lovingly brushed it. Involuntarily, I closed my eyes and leaned into his touch. His hands were easily two times larger than my own.

"You said it yourself, 'I'm your maid and I'll do whatever you say,'" Antonio said with a reassuring tone, "And it helps that you're hot as fuck in my girlfriend's clothes."

I didn't say anything at first, just staring into space as he caressed my cheek and ran his fingers through my hair.

When I finally worked up the courage, it felt like I didn't have enough air in my lungs to speak. Very quietly, I said, "Yes sir. I'll suck your cock."

He grinned like I'd never seen him before.

"Good maid," he said.

Antonio moved forward, his hand still on the back of my head. With his left hand, he dropped his trousers to the floor. Then he pulled down the waistband of his boxers.

His cock was huge. My close-up view made it look even bigger than when I had seen it during the bet. It started only semi-hard but grew until the head was pointing just inches from the bridge of my nose.

I realize I was staring with my mouth open.

"Go ahead, kiss it," Antonio said.

I moved up onto my knees, closed my eyes, and lightly kissed the head of his cock. It was salty with pre-cum.

He let out a slight moan and said, "Good girl."

I kept kissing the head of his cock, moving my lips around as I did so. I was probably bi but had never really explored that side of myself. My cock grew hard in my panties. I shook my ass slightly and the teddy made a swishing sound.

I put a hand around the base of his shaft and started to gently stroke it. Then I stopped kissing and began moving my tongue around the tip of his cock. He moaned more.

I rubbed my hand up his big cock. With a bit of courage, I put my mouth around the tip. Then I took as much of the dick into my mouth as I could and continued stroking him with my hand.

"Don't neglect the balls," he commanded.

Wordlessly, I kissed down his shaft until I reached his balls. I sucked them one at a time and then together, all while moving my hand up and down the length of his cock. I maintained eye contact and hoped I looked even half as hot as his girlfriend doing the same.

"Oh fuck," he said with a twinge of a moan.

I went back to sucking his cock, bobbing my head up and down. I was able to fit about half of him in my mouth without gagging.

"It's OK, I'll train you better," he said, grabbing my hair in a fist.

I keep sucking him and stroking his shaft. With my left hand, I caressed his balls. In the moment, I didn't even care if my sucking sounds could be heard outside the room.

All I wanted was to serve my master.

I was working my tongue in a way I had only ever done for pussy. I licked all across his super-hard cock and felt it shiver slightly. A splash of cum shot out on my face.

"Put your mouth back over it," Antonio said, breathing heavy.

Continuing my strokes, I wrapped my lips around the head of his cock and took him into my mouth. Antonio started to shake. His dick contracted slightly.

I moved my hand faster and kept caressing his balls. His cock spasmed and warm liquid shot from it. It was salty and more and more came rushing into my mouth. Antonio moaned in a more masculine way than I ever had before. His dick shot one last bit of cum and then relaxed. Antonio pulled it from my mouth.

"Swallow," he said.

Embarrassed and humiliated but more horny than anything else, I did as I was told. I swallowed all of Antonio's cum and then stuck my tongue out as proof. Without even intending to, I wiggled my ass.