My Roommate's Maid Pt. 01

I never thought I would lose the bet.

One year ago, I was at Uni and rooming with three other guys. None of us knew each other before becoming roommates. We just all happened to pick the same set of apartments and were placed in together.

We got along all right.

To be honest, we didn't see each other that often.

Marshall mostly stayed in his room playing games. Antonio was always out with his girlfriend. I don't know where Tomas went, but he was rarely there either.

That was until the lockdowns of 2020 happened.

There was nowhere to go. Nothing to do. We couldn't leave the apartment and we couldn't invite anyone else over. Suddenly, we were seeing a lot more of each other. Marshall was fine. His life as someone with 1,000 hours in Stellaris was basically unchanged. But the rest of us started to chafe. Antonio's girlfriend had moved out of state to stay with her parents during lockdown and you could tell he was pent up. He would snap occasionally if the dishes weren't done or if laundry was sitting out for a couple days.

But at least Antonio was mostly quiet about it. Tomas would loudly bemoan the current lack of pussy in his life. It was unclear to us how much he was actually scoring pre-lockdown. It was beside the point. None of us were now.

I had dated off and on through college but never more than a few months. I was skinny, shy, and had a hard time approaching girls. Some were into me anyway but I was never in the right headspace to date. The last person I was involved with was Kim, a girl from one of my econ classes. I had gotten to second base with her just a couple weeks before lockdown.

Little did I know that'd be the farthest I get with a girl for a long time.

-

Maybe it was the being home all the time or the anxiety from the world around us, but the apartment started getting messier. Dirty dishes, yesterday's doordash, dirty laundry, you name it. None of us were great at cleaning it turned out. I'll admit, it hadn't been one of my priorities. The whole time I was just trying not to fail online school.

One morning, Antonio came into the living room and stopped dead in his tracks. I was studying and Tomas was playing some racing game there. It wasn't in the best state. Our one and only table was covered in papers and fast food bags. The floor was carpeted in blankets and clothes. I noticed Antonio was scanning over it all.

"All right, we need a maid," he declared.

"Sure," Tomas said, not really hearing him.

"No I mean it," said Antonio, a slight growl in his voice, "This is place is a pigsty."

He motioned at me. "Go get Marshall. We need to have an roommate meeting."

I ran off to Marshall's room, the farthest room in the apartment. The door was open and he was staring blank-eyed at his computer. It was some game where you play as Sweden in the 1400s. His room was somehow messier than the living room. I couldn't even make out his bed.

"Hey Marshall," I said, "Antonio wants a roommate meeting."

"In a bit," he said, not looking away from the screen.

"I think he means now. He seemed a bit upset."

After some cajoling, I was able to get Marshall away from his paradox game and into the living room. Tomas had turned off his racing simulator and he was standing there with Antonio.

"We need a maid," Antonio repeated.

"Yeah we get it," Marshall said, yawning, "Be better at cleaning. Whatever."

This hadn't been our first roommate meeting. Previous meetings had ended with us all promising to do our best and that promise then lasting all of four days.

"No this is different," Antonio said, "All four of us cleaning hasn't worked out. We need one person to do it."

"You volunteering?" Marshall scoffed.

"No, hear him out," Tomas said.

Antonio continued, "We need to have one dedicated maid who does the cleaning. That way it gets done."

"And who would this be?" Marshall asked.

"We'll decide that. Fairly."

No one said anything for a few seconds. I didn't know who to look at so I just stared at the hoodie-covered floor.

"How?" I finally said.

"That was Tomas' idea," said Antonio, motioning at the lanky student next to him, "Do you want to explain it?"

Apparently they'd talked it over while I was with Marshall.

"Sure!" Tomas' face lit up, "Basically, it's like a hierarchy. Since no one wants to do the cleaning, that means the maid is at the bottom. They'll take orders from the rest of us."

"And so, you might be asking, 'what is this hierarchy based on?' Well, the same thing all good hierarchies are based on: manliness! And how better do you measure manliness than with dick size?"

Tomas smiled. No one returned the smile.

"I don't love it," Antonio said, arms crossed, "But I've done more than my fair share of picking up after the rest of you. And I'll admit it's a fair way to decide things."

After a while, it became clear that Antonio and Tomas were serious about this. Marshall too was entertaining the idea.

"And so one person would do all the cleaning?" he asked.

"Yea pretty much."

This is crazy. How long would this situation even last? But I guess if everyone is on board...

I looked over my roommate's faces. Everyone seemed to be doing the math in their head. Since Tomas suggested the idea, it's likely he has a big dick (what am I thinking?) but that doesn't say anything about the other two. Mine was a perfectly respectable six inches, average. And if I had average, there was a good chance one of the others was smaller than me.

And the prospect of either Antonio or Marshall cleaning up after me did sound pretty good.

"I'm good with it."

"Seriously?" Antonio asked.

"Hell yeah!" exclaimed Tomas.

"Me too I guess," said Marshall, scratching the back of his head.

Tomas rubbed his hands together. "Now, once we agree on this, there's no going back. The smallest dick will have to clean for us for the rest of the semester."

We all agreed, either with a 'yes' or a nod of the head.

"So do we just whip them out?" asked Marshall, holding the waistband of his sweats.

"I guess," said Antonio.

"On three."

I had been so sure.

Six inches was respectable, I told myself. I thought the math was on my side.

One after the other, my roommates undid their jeans or pulled down their sweats. Marshall's cock extended over seven inches. Antonio's, easily eight. Thomas was over nine.

My cock, only partially hard, was nothing compared to theirs.

Antonio, Marshall, and Tomas looked between each other.

I was going to be their maid.

My tasks started pretty much immediately.

Right as the four of us zipped up our pants, Antonio stared straight at me.

"Start cleaning."

I wanted to protest, to make up some excuse, but his tone and the embarrassment I had just endured shut me up. I started picking clothes off the floor.

It was awkward at first. I always felt the other three guys' eyes on me while I cleaned. That quickly subsided though and I fell into a rhythm. Once an area was clean, it wasn't actually that difficult to keep it clean. I sorted papers, wiped tables and countertops, swiffered, dusted, washed dishes, took out the trash, and collected loose clothes.

I was surprised how easily I was able to balance it all with my schoolwork. If anything, having the chores to do made me more productive with studying. Discipline or something like that.

The dynamic between the roommates didn't change much either. Tomas would still excitedly tell me some fact (probably untrue) he read online. I'd talk history with Antonio (that was his major). Marshall still kept to himself most of the time. The only difference was the new phrase, "Clean that."

After they would finish a dish or spill something, I'd have to rush over and clean it for them. The orders from them were never harsh, but they were firm. To me, it was a momentary disruption in our conversation. I'd stopped to clean for a minute or two and then we'd be back to talking about sports or history or whatever.

A few days passed and I considered backing out of the agreement. The apartment was a lot cleaner than before, sure, but the embarrassment and obligation of that first night had worn off for me.

It was tough. The others had gotten used to me cleaning. And I kinda had too.

I put up with it for a few more days, sweeping, mopping, and cleaning our communal bathroom, before working up the courage to talk to everyone. I was about to call another roommate meeting when Tomas called one first.

Tomas, Antonio, and I gathered in the kitchen. Marshall came in a few minutes later, sporting eyebags from a late night of gaming.

"So, I was thinking," Tomas said, "And I talking it over with Antonio. We want to stay in the apartment over summer. I personally don't want to be spending lockdown trapped with family."

"Fuck no," said Antonio.

Tomas looked at me. "I'm sure you're getting sick of cleaning and I get that. But Antonio and I talked it over, and we're willing to cover your portion of the rent over summer if you stay on as a maid."

My eyes widened. What timing! I was just about to quit. Can I really pass up this offer though?

"It's not much extra," Antonio said, "And Tomas and I will be pulling in money from remote work in the summer."

Marshall raised his hand. "If I pitch in, can I have him clean my room?" He talked about me like I wasn't even there.

"Sure!" Tomas smiled, "If he's cool with it."

All at once, my three roommates turned to stare at me.

"So how about it?"

I realized I was blushing terrible. I can't pass up free rent. And the cleaning's not even that bad.

"Um, yeah s-sure," I mumbled.

"Sweet!" Marshall said, "I want you to clean my room tomorrow, OK?"

I nodded and blushed more. Tomorrow was going to suck but free rent was free rent. And I too didn't want to move back home for lockdown.

As everyone was going their separate ways, Tomas grabbed my arm and held me back.

"One more thing," he said quietly.

I looked back at him expectantly. He had a pretty firm grip for such a skinny guy.

"If you do want us to pay for you, there is a condition."

Tomas let go of my arm. I leaned back against the wall and looked at him expectantly.

"Is this from you or Antonio?" I asked.

"Just me, but Antonio is cool with it," he said, "Basically, you'll need to wear a uniform. Nothing crazy, just something while you clean."

Uniform? What is he talking about?

I waited for him to explain. Tomas was blushing a little now too.

"You see, Antonio's girlfriend left behind some of her clothes when she moved. And among those clothes was a french maid outfit."

Shortly after moving in, I had admitted drunkenly that I'd crossdressed a couple times before. I know immensely regretted letting that slip.

"Come on, I know you've done it before. And I feel weird ordering a regular dude to clean up for me. This would make everyone a lot more comfortable with the setup."

Tomas could see I still wasn't convinced so he added, "Besides, no one would even see you except for us. Closed circuit."

I sighed deeply and muttered "fine", anything to get this conversation to stop.

"Amazing!" he exclaimed, "You're gonna look so good. I mean, you basically look like a woman already."

And before I could respond, Tomas had jetted off to his room. I rubbed my arm meekly and dreaded the next day.

The following morning, Antonio brought the outfit on a hanger to my room.

"Tomas said you wanted this."

Wanted was doing a lot of work in that sentence.

"Um, yea thanks," I said, not meeting his eyes.

Antonio left the outfit on top of my dresser. After he was gone for a few minutes, I investigated what he had brought. There was a white lace bikini bra, white lace panties, garter, white fishnet and a french maid dress with a lace fringe and spaghetti straps to hold it up.

I felt a little weird but fought through it. Against my better judgement, I stripped and started to put on the costume.

I pulled the bra over my head and straightened it. It was slightly sheer so you could still see my nipples. Then, I pulled on the panties. They were so smooth and my cock got a little hard as they brushed over it. Then, I secured the garter around my waist and attached the lace-top fishnets to it.

I had to admit, my legs looked great. My cock got a little harder.

Finally, I shimmied into the maid dress. It was made for women so the skirt barely covered my ass. Embarrassed and a little aroused, I left my room and made the long walk to Marshall's.

I knocked and the already open door swung open. Marshall pushed away from his desk when he noticed me. His mouth hung open slightly.

"Holy shit," he said.

I must have been blushing terribly.

"It was Tomas' idea," I mumbled, "You still want me to clean?"

"Sure, yeah, go ahead!"

The room was mostly messy and not dirty. It was a matter of sorting his pile of clean clothes from the dirty ones, folding them, and then doing some other miscellaneous organizing. Not as bad as I was expecting.

I spent about an hour in there while Marshall played his games. I tried not to bend over too much and was constantly readjusting my dress.

But as I was finishing up, bending over to pick up some stray philosophy papers, I noticed Marshall with his phone out behind me. Then, a series of clicks.

I wheeled around, my face going bright red, as I faced Marshall taking photo after photo of me. And to my horror, an erection grew in my panties right then.

There a half-dozen more clicks before he put away his phone.

I pulled my dress down to cover my cock, which was threatening to leap out of my panties.

He smiled. "Relax, just collecting some blackmail material."

I couldn't tell if he was joking.