My Roommate's Maid Pt. 03

It was 9AM. After a quick breakfast, I was starting my routine for the day.

I stripped out of my short shorts and crop top. Using a makeup Youtuber as reference, I put on foundation, winged eyeliner, gray eyeshadow, mascara, blush, and glittery setting spray. Then I pulled on lacy white panties, a sheer white lace bra, white-topped fishnet stockings, and a short little french maid dress. I tied the bow on the dress's back and was ready to start my day.

To be honest, I hadn't fully considered my situation up to that point.

Here I was, wearing something and doing things I would never have considered a few weeks ago. How had it become my daily routine to dress up as a maid and obey my roommates as masters?

I told myself that it had been all out of my control. But that wasn't exactly true.

I had agreed to everything, sometimes reluctantly but other times enthusiastically.

There were so many times where I could have backed out or said no, but I didn't. Not when the bet was first made. Not after a few days of cleaning. Not after Tomas suggested I wear a maid dress.

And not even after I sucked Antonio's cock.

Maybe I liked this.

The day wasn't terribly busy and I quickly finished all the chores assigned to me. I had plenty of time to do schoolwork, read, and watch TV.

Later in the day, as I was wiping the counter and about ready to change out of my maid uniform, Antonio grabbed my arm. He didn't say anything. I was about to speak but nothing could get past my lips.

There was a glint in his eyes. He led me quickly and quietly back to his room.

"I wanted to do it with you in the maid dress," he said with a smile.

Antonio put down a folded throw blanket. Without having to be told to, I knelt down onto it.

I opened my mouth.

"Good maid," he said with a smile.

This went on for about a week uninterrupted. Whenever Antonio wanted, he would grab me and pull me discreetly into his room. He would give me something to kneel on (usually a blanket, once it was a pillow) and then he would have me suck his cock.

I felt so safe and comfortable when he was giving me orders. And then I felt so attractive and powerful when I made him cum.

Every time, he came in my mouth and made me swallow. I started to get better at it, taking more and more of him into my mouth. I knew exactly where to lick and kiss to make him feel good. After each time, he'd take me and we'd cuddle on his bed for a while. Being wrapped in his arms was always the best part of the day.

It wasn't romantic.

Antonio, though polyamorous, had a girlfriend out of state who was always going to be his primary partner. It made me excited to wonder if she was in on it though. Was Antonio telling her the extent of everything? About how he had turned one of his roommates into a maid who was sucking his dick daily? I should have been horrified at the idea of someone outside the apartment knowing what was going on. But instead, the possible exposure turned me on.

I asked him once when we were cuddling in bed.

"Does your girlfriend know about me?"

Antonio chuckled.

"Yeah we're open," he said like it was obvious, "Just as long as we keep our main focus on each other, we're allowed to explore other options. She has a girlfriend out of state licking her pussy while we're apart. And I have you."

I liked the way he said that, "I have you." I blushed a little. It was weirdly hot to be treated like an object by him.

One night after a long day of laundry and vacuuming, I decided to surprise Antonio. It had been a month to the day since I made that fateful bet that turned me into a maid. One month of cleaning. And three weeks since I had to start cleaning in a maid dress.

I dolled myself up with tasteful eyeliner/mascara and light-pink eyeshadow. I put on some lipgloss. Then, I changed into the most risqué girl clothes I had. I hadn't worn these particular ones out of the pile Antonio had given me. They were one of the two sets of lingerie his girlfriend had left behind (the other being the mauve bra/boyshorts, pink stay-up stockings, and teddy I had worn when I first *served* Antonio).

This set of lingerie was black. A lace push-up bra, snug hipsters with a bow in front, a lacy garter belt, sheer black stockings, and arm-length sheer nylon gloves.

I felt so sexy with it and makeup on.

Without thinking about it much, I struck several poses in front of my room's mirror and took some photos of myself (I guess Marshall was rubbing off on me).

Then, I got back in bed and tried to strike an even sexier pose. Antonio usually came by around this time and I wanted to see how he would react.

When he didn't stop by immediately, I started scrolling on my phone. I quickly became bored of quarantine-era Instagram (how many people can make the same post about being stuck at home!) and turned it off.

I sighed.

Out of boredom, I rubbed my legs together. The nylon felt so good against my bare legs and body. I started to take notice of how the whole set felt. The clasp of the bra against my back was firm and tight. The hipsters were snug and comfortable over my penis. My gloves glided smoothly as I ran them up and down my body.

The encounters with Antonio rarely focused on me but I still got a lot of sexual satisfaction out of it. Feeling sexy and making someone else cum was enough for me. Thinking about his big cock in my mouth, I started to get hard in my panties.

I moved my gloved hand down and brushed the edge of my cock. It instantly sprung up. Looking at it now and comparing it to Antonio's massive cock, I realized how average it actually was. I'd been so naive to make that bet a month ago.

I slowly ran my hand up and down the shaft of my penis. The texture of the glove felt so good. With my other hand, I gripped the sheets below me. My cock got even harder.

Then the door opened.

I sat up quickly. This isn't how I wanted Antonio to see me.

"I figured I'd drop off laundry now so you can start with it tomorrow morning..."

He trailed off. It wasn't Antonio.

It was another of my roommates, the tall, scrawny jokester Tomas.

Tomas looked down at my exposed cock and then met my eyes. He smirked.

"I texted the groupchat. I guess you were preoccupied."

I looked anxiously over at my phone. I had been so caught up in the moment that I hadn't noticed the notification bar at the top of the screen.

"I can explain," I started.

Tomas put up a hand. I quieted. He dropped his laundry in my hamper by the door.

"Put on something to cover up your lingerie," he commanded, "And then come by room. I expect you there in five minutes."

He left before I had a chance to respond.

XXX

I don't know if it was his confident tone or my incredible embarrassment at getting caught but I didn't dare disobey him. I put on some of the loosest fitting girl clothes I had (an old sleep shirt and sweatpants) and nervously left my room.

I shuffled down the hall. Luckily, his room was right next to mine so I didn't have to pass by Marshall's or Antonio's.

My heart was beating in my ears. I formed a fist to knock at Tomas' door but stood there motionless for half a minute.

Finally, I knocked as quietly as I could.

There were a few more seconds of interminable quiet and stillness before Tomas opened the door.

"Come in."

Tomas sat down on his bed and watched me close the door after myself. I stood sheepishly in front of him.

"Take off your coverings."

I did so slowly, first taking off the sleep shirt to expose my bra and then stepping out of the sweatpants to reveal my stockings. My cock was still semi-hard under my black panties.

He looked me up and down.

"So you're really into this crossdressing thing, huh?"

I stammered but didn't say anything.

Tomas put up a hand to quiet me again. "Chill. No need to be embarrassed. I just thought maybe you were doing it out of obligation, the whole cleaning and dressup. But no one told you to dress up like this."

I shifted nervously to one side. I felt so exposed standing there in front of him.

"I'm going to ask you a few questions and I want you to answer honestly," Tomas said. He sounded calmer and gentler than normal.

"OK," I said, not knowing what was coming.

"I enjoyed making you wear the maid dress and Antonio's girlfriend's old clothes. Never expected you to say yes. So, how would you feel if I ordered you to do other things?"

I blinked back at him.

"It's all right. You can answer any way you want. I won't judge."

"What kind of things?" I asked.

Tomas smiled deviously.

"So, I watch a lot of porn." He seemed weirdly proud of that fact.

"And for a while now, I've been wanting a sissy. Dominating girls is great but I can't really do that during quarantine. And there's something so hot about turning a boy into a girl and having him serve your every need. And with you here, I have the perfect candidate."

Sissy? Every need?

"What do you mean?" I asked quietly.

"Well, there would be more rules to follow. I would use you however I pleased."

I felt trapped, unable to protest or move. But I also felt excited. My mind filled with all the possibilities of what Tomas was suggesting.

"It'd be like what you're doing with Antonio but more," he said.

"You know about that?" I exclaimed in shock. Reflexively, I covered myself with my hands.

"It was kinda clear with how much time you were spending in his room. And he confirmed it when I asked him."

I stood there, completely frozen. This can't be real.

"So you want me to suck your cock?" I asked in a harsh hiss. My teeth were gritted and my fists balled at my sides.

Tomas smiled. "That and other things."

I gulped.

"It'd be different with me though," Tomas said, "Antonio's just getting off. I'd be in control of you. You'd be my property."

"Property?" I spoke at barely above a whisper. It was like saying it out loud would make it real.

He moved up to me and grabbed my ass. I seized up a little.

"Say 'yes sir.'"

I begged myself not to say it but for some reason, I couldn't stop the words from leaving my mouth. Not meeting his eyes, I whispered "Yes sir."

Tomas grabbed my ass a little harder.

"Now say 'I'm your sissy.'"

"...I'm your sissy."

"Say 'I'm your property. I give you complete control of me.'"

Meekly, I said, "I'm your property. I give you complete control of me."

"Good sissy." He slapped my ass.

I tugged at my garter belt. Why did I just say all that? Am I going insane?

"Head back to your room," Tomas commanded, "I'll go more into detail with my expectations tomorrow morning. But until then, no masturbating. If you do, I'll spank you."

I nodded my head anxiously.

"What do you say, sissy?"

"I understand, sir."

He looked at me expectantly.

I gulped again and then said, "Thank you for making me your property, sir."

"You're welcome, sissy." Tomas smacked my ass again. It stung a little and I yelped. He grinned and said, "I'll see you in the morning."

He leaned back onto his bed and watched me leave.

"Goodnight, sir," I said, still unable to fully meet his eyes.

The short distance between my room and his seemed to stretch on forever. I walked back in only my lingerie.

The morning came quicker than expected. I didn't know if Tomas was going to come to me, so I ended up just heading to his room. I had changed out of the lingerie and was wearing a miniskirt and crop top along with cotton boyshorts.

I was nervous and a little horny. I had followed Tomas' order not to masturbate last night.

He opened the door a little while after I knocked. Luckily, Antonio and Marshall weren't up yet.

Tomas beckoned me in.

"Strip," he commanded.

To this day, I have no idea why I followed Tomas' (or for that matter, Antonio and Marshall's) commands so easily. Maybe it was how he said it or maybe I just sorely needed some structure in my life.

I did as I was told and pulled off my crop top and dropped my miniskirt. He crossed his arms and looked at me, so I slid off my boyshorts as well. My dick wasn't hard and I was acutely aware of how small it looked between my legs.

Tomas scanned my body with his eyes. I felt far more naked than I ever did with Antonio.

"All right, sissy," he said, snapping out of scrutinizing my nude body, "From now on, if you're not calling me 'sir' you are to call me 'daddy' or 'master.'"

"Yes sir." I tried not to think about how terrible of an idea this was.

"I'm going to give you some rules. If you break any of them, I'll punish you."

He continued, "I'll send the word doc. After we're done here, you're going to print it out and display it prominently in your room. That way there will be no excuse for forgetting one."

"Yes sir," I said again.

I shivered slightly. I had butterflies in my stomach from a mix of horniness, shame, and excitement about what these rules would be. It felt like a new movie trailer dropping or reading a tense part of a book right before the climax. I had to remind myself that this wasn't a book or movie, and that these rules were deciding how I would live while I was in this apartment.

Tomas began reading the rules.

"1. You are my property. While I will factor in your enjoyment and your wishes, any command I give, you have to follow," he said, "And once I give you a command, you must thank me for it."

I nodded. "Thank you, daddy."

I felt a weird tingle go through my body.

"2. No more masturbating. From now on, I will supervise all of your orgasms."

"3. While my property, you are not allowed to wear any boy clothes. You will either be naked or in the girl clothes of my choosing."

"4. You will continue performing all cleaning in the apartment and taking orders from Antonio and Marshall."

"5. Your name is now Sophie. When you refer to yourself, you must call yourself either Sophie, Sissy, or Maid. Others will start using she/her for you now."

"6. If you ever have to ask anything of me, you must first get down on all fours and bow."

"7. If I ever punish you, you must thank me after."

"8. You will perform sex acts when asked."

My cock grew a little hard as he said that. I blushed and looked away.

"Just to be clear sissy, from here on out, I will no longer be masturbating either. Making me cum whenever I want is now on your list of daily duties."

I can't believe this. Now I'm a sex toy in addition to a cleaner! I really shouldn't go along with this. It's not too late to back out. Tomas will understand.

But instead of telling him no or saying any of those things on my mind, I simply said sweetly, "Thank you for all the rules, daddy."

Tomas smiled.

"Of course, sissy. Do you know how you can thank me?"

"How, sir?" What am I saying?

"Beg to suck my cock," he commanded.

This legitimately can't be happening. I know you're horny but make better decisions! Stand up for yourself!

A thousand protests rushed in and out of my mind. But the truth is, deep down, I needed someone to dominate me. I just didn't know it before. This wasn't exactly what I was looking for (past, straight me envisioned this happening with a leather-clad dominatrix) but I went along anyway.

I got down on my knees.

"Please sir, let me suck your cock."

"Hmm, I don't know."

"Please daddy, I need it so bad. I'll do anything."

"Anything?"

"Anything, daddy. All I want is your cock in my mouth."

OK, maybe I was overdoing it. But screw it. I want this. I actually want this.

Tomas pulled down the hem of his sweatpants. I caught a glimpse of the base of his long cock.

"Who am I to deprive you then," he said with a smile.

He took his cock out of his sweatpants and started rubbing it. Even flaccid, it was bigger than my cock hard. I remembered back to a month ago when I'd seen it fully erect, the biggest of all my roommates.

I was completely naked. He was completely dressed. I was on my knees. He was standing. The power imbalance could not have been greater.

Tomas took the back of my head and guided it towards his cock.

I hesitated only a little. I started kissing along the side of his shaft and licking down to the base. It quickly grew hard, extending about nine inches.

Completely in awe, I began to massage his cock with my left hand. I licked up the side and kissed the head. My lips came away salty.

"Show me what you learned with Antonio," he said.

I took him deep into my mouth. I licked down and sucked on his balls. He moaned in pleasure and then held the back of my head. I rubbed his shaft and bobbed my head up and down on his cock.

I kept going, sucking him and licking him like it was my only purpose in life. I looked up and made eye contact with him. Tomas looked back approvingly. Something like pride swelled up in my chest.

I'm certain that anyone outside the room could hear it as his cock repeatedly touched the back of my throat. But I didn't care. I wanted to make him cum so badly.

How did this happen? I used to be a normal guy. But for a full month, I've been dressing as a girl and doing all the chores for my roommates. And now, I'm completely naked and sucking one of their cocks!

I was no longer a boy or a girl. I was property. A sissy. Whatever Tomas wanted me to be. I even let him change my name. I was [Redacted]. Now I'm Sophie.

Tomas pulled my head away. His cock was fully hard and dripping with my spit. It twitched in front of my nose.

"Open your mouth," Tomas commanded.

I did so, sticking my tongue out.

"Good sissy," he purred, "Swallow every drop."

Tomas started stroking his dick furiously over my face. Soon, his cock convulsed and sticky hot cum came streaming out. My face was covered in the liquid and some of it splashed into my mouth. I swallowed it quickly and went to wipe away the rest.

"Stop," he commanded. "Leave the cum on your face. Dress back in your skirt and top and keep the cum on until you're in the bathroom and can shower."

I nodded.

"What do you say?"

"Thank you for your cum, sir," I said in a girly voice.

"Good Sophie. After you shower, change into the lingerie you were wearing yesterday."

"Yes daddy."

I did as I was told. I pulled up my panties and skirt and put my top on, being careful not to mess up the sticky liquid on my face.

I looked nervously at the door. I felt unsure about heading into the hall with Tomas' cum on my face. But I knew better than to question him. Going off the new rules, I'd have to get onto all fours and bow if I were to ask anything of him.

With a big breath in, I closed my eyes and opened the door.

Thank God. Neither Antonio nor Marshall were there.

I curtsied and said goodbye to my new daddy. Then, quickly and quietly, I ran to the bathroom to shower.

It felt good to wash up after that. I was super turned on from making Tomas cum. Still, I didn't touch myself. I took his rule about not masturbating seriously.

I don't know why but I accepted all of his rules without much thought.

Maybe the month of obedience and crossdressing had primed me. Maybe there wasn't much farther to fall.

Regardless, the only certainty was what I was now.

Sophie. Sissy. Maid.

Sissy was an identity I had come across but never really associated with. Now that it had been placed upon me, I accepted it wholeheartedly. It just felt right.

Getting out of the shower, I admired my hairless body for a moment before changing into the black lingerie from last night. It felt even better against my skin after drying off from the hot shower. My cock got hard in my panties.

Marshall and/or Antonio might be up by now, but I decided to chance it anyway. I wanted to please my daddy. I left the bathroom to report back to him.