Roommates [Femdom] [M/F]

Roommates

1

When most people say “I’ll never forget the day I met —-,” it’s usually for some corny reason like “the way her eyes caught the sun” or “how I knew she was who I was destined for.” I’m not saying that’s all bullshit, but the reason I’ll never forget the day I met Eva is simple—it was June 1st, the same day every other lease I’ve ever had has started.

Well, maybe it would be more accurate to say that’s why I remember the date. As much as I hate to admit it, I’ll never forget walking into the New York City apartment, nervous about meeting my new roommate, nervous about having my first ever woman as a roommate, thinking about moving in my couch, and suddenly walking into the bluest eyes I’d ever seen.

These eyes weren’t a pale blue, not a dark blue, but **blue**. Blue that smiled with you and shone bright when she laughed, and blue that was like ice, like steel, so hard that you knew you could break on it with nothing you could do about it.

All of these thoughts were rushing through my head and rammed into my eyes, my ears, nose, mouth, trying to escape, when I realized that she was looking at me, half-laughing and half-puzzled. She had been holding out her hand for at least a minute. I grabbed it and shook it.

“Hi.” Her voice rang high and sweet. “I’m Eva. I hope you’re Charlie, and not some random man who’s just come in to stare at me?”

“Um.” I stuttered and stumble despite my mother’s best warnings about using that word around women. I tried to recover. “No! I mean, yeah! I’m Charlie! Actually, I’m your new roommate who’s come to stare at you.”

She laughed at that, and I thought I might die. My heart was trying to beat its way out of my chest.

“Well, good then. Plenty of staring to be done over the next year.” She pointed to a room, the bigger one. “I’m taking that one. Come help me move in my stuff and then I can help you with yours.”

I followed her out of the apartment.

Eva and I had met through our mutual friend, Hannah. Hannah was an old hometown friend of mine and a sorority sister of Eva’s. We were both moving to Queens for work and Hannah assured us that we were a perfect match.

She informed both of us that each was each friendly, fun, and smart. She told me that Eva could wingman me and would stay up late talking about my random bullshit. She told Eva that I was sure to be respectful – “it’ll be like living with your little brother. He’s cute like that.”

Once I got over the initial shock of meeting Eva, I found that she was all that I had hoped for and much more. She had great music taste, left me alone enough, came into my room and rescued me when I needed to get out (I always slammed shut my laptop whenever she came in, red faced and grabbing my covers. Of course, she never knocked, and always looked at me with a half-teasing, half-pitying look). We watched TV together every night and she always chose the shows, inevitable something that I liked so I never minded it. We worked out at the same times.

Even the first weekend we spent together was amazing. We stayed up drinking bottles of wine and talking before I blacked out and she put me to bed.

Not to mention, Eva was stunningly beautiful. It wasn’t just the eyes that had stopped me in my tracks. She had light brown wavy hair, wasn’t too short but not too tall (we’ll say 5’8” if you’re looking for a measurement, but I never had the nerve to measure her), an amazingly toned body with perky, beautiful tits that were just the right size and a jaw-dropping juicy ass just right in proportion to her tits. She was, without a doubt, the most beautiful woman I had ever talked to.

This fact made it so much easier for me to tell myself “it’s alright, you’ve got no shot, so don’t make it awkward. She’s just like a sister to you, so be a good, loyal friend and a good, polite roommate.”

And just like that, we became great friends over the next two weeks. She even tried to help me talk to girls on Tinder but she would always just shake her head as I refused to close the deal on my 56th message, persevering with my lecture on Hemmingway and saying “if she’s really the one, she’ll be okay with talking all night before we meet.

I don’t know why she ever even considered me, to be honest. I mean, I suppose I think I’m good looking, I’m 5’11”, I have blue eyes, I’m skinny but I run and stay in shape. Maybe I could even be considered to be smart. But come on. I’m your skinny awkward little brother; funny, but not a comedian; outgoing, but not confident; fun, but not a boyfriend.

Maybe she did think I was cute like a little brother. But really, come on. This is a Goddess of New York City we’re talking about.

Either way, things started to happen. Slowly at first, but they happened.

The first thing I remember happening was about a month into living together. We were watching some anime she knew I’d like. I was engrossed, perched on the very edge of the couch and leaning into the armrest—basically, I was as far away from the feminine side of the couch as I could be. I know some of you will know the feeling I’m describing, either from living it or watching it.

Suddenly, I felt her gaze drilling into me. I looked over and she was staring at me. Her eyes were laughing and she was grinning.

As you do with pretty girls who you catch staring, I instantly looked away.

A couple seconds later, long enough to be painful, I looked back saw her staring and looked away again. Just like that.

“Hey Charlie,” I heard her speak and tried to pretend none of that happened as I nonchalantly nervously glanced over, “aren’t you uncomfortable? You look like you’re about to fall off the couch.”

“I’m fine.” I was extremely uncomfortable.

“Seriously?” She sat up a little. “We have this nice couch, are you seriously not going to use it?”

She said this as she was laying down, stretched out, with a blanket on. She took up a huge majority of the couch. I stuttered, not knowing how to tell her this. Eva was not the sort of girl you contradicted.

“Aww…” I couldn’t tell if she was being sweet or teasing me, a little meanly. “Is the shy boy afraid to come sit by the girl?”

My cheeks flushed.

“You’re seriously scared? What, sweetie, you think I’m gonna bite your head off?” She gnashed her teeth together and made a biting sound as she said this, and it was so cute and beautiful and awful I thought about how scared I was and how she could bite my head off and I’d say: “Thank you Eva. Can I do anything else for you?”

“I’m not scared. I… I just don’t want to make anything awkward here.”

“Why would it be awkward, Charlie?” She sat up. She stared at me and held the silence and I looked away trying to think of what to say, knowing how absurdly out of my league she was.

“Look at me.” I looked at her and her eyes were a solid blue, calm, unmoving.

“You’re like a little brother to me, right?” She waited until I answered yes. “And so how would it be weird for a little brother and a big sister to cuddle, like old times? I know you could use some cuddles.”

She babied her voice at the end, and though I usually hate that, it made me realize how long it had been for me and how lonely I was. I realized Eva was waiting for me to answer and so I softly admitted that, yes, I could use some cuddles. My cheeks flushed and it felt humiliating but somehow wonderful to say.

She lay back down on the couch and, still looking at me, she patted her lap. Maybe I should have pulled her into me, put her legs over mine, something. But I pulled the blanket up and slipped under, curling a little and resting my head on her lap.

“That feels nice, doesn’t it?” I didn’t say anything and she put her hand on my head. “Doesn’t it feel good to rest your head on your big sister’s lap?”

“Yes. It feels really nice, Eva.” I said as she started idly running her hands through my hair. I couldn’t focus on the TV anymore; I could only close my eyes and feel pleasure radiate from her hand as she stroked my head. I had to adjust to hide my erection.

“I like that your hair is long.” She was idly playing with a strand.

“Mmm.” I had to make sure I wasn’t drooling.

“You look cute with it this long. Keep growing it out.”

“Mkay.” I nuzzled my face into her leg and fell asleep.

2

After that night on the couch, Eva started being, well, more sisterly. In a big sister way. She’d tease me, prune me before I went out, remind me to do the dishes even as I was doing them. I didn’t really mind it. It was nice to have her notice me like that. And every night, we’d watch TV as I curled up on her lap and listened to her talk about her day, ask me about mine, tell me about the TV show, tell me what I needed to do the next day (I always took the trash out and got the mail. Thanks for nothing, chivalry).

She started getting more competitive, too. I usually ran, say, once in a blue moon. But with her prompting I started running every other day and going for long walks, with or without her, the rest of the week.

Eva went to the gym every morning, without fail, but no matter how much she pressured me (“the chicks will dig it!” she’d say as she wrapped her hand almost completely around my bicep) I always refused to go.

One Saturday morning, I was up earlier than normal at 10:30.

“Oh wow, early riser today!” Eva looked at me over a cup of coffee. She was up at 8 every morning and never seemed to get tired or feel hungover, or otherwise show weakness.

“Yeah, I thought I might do something productive since I felt awake.”

“Gym! Gym! Gym!”

“Not that productive, Eva. I was thinking more like read or write something.”

“Aw!” She frowned and pouted.

Suddenly, she stood up and walked over to the table where I was eating and started at me. I tried to stare back, with some success. I could smell her lightly fruity shampoo and was already vaguely hard. I tried to think about something else but I never could.

“You know, I bet you’re a real weakling. You never work out.” This sudden meanness was out of character for Eva and it stung a little bit.

“I’m a man. I don’t need to; just look at me. I’m like Hercules!” I flexed and smiled.

Eva didn’t laugh and just kept looking at my arms. Suddenly she sat down.

“Arm wrestle me. Right now. Loser has to do 25 pushups and the dishes.”

I pushed my cereal bowl back. I didn’t want to embarrass her. I’m not that competitive, anyhow.

“Well, I—”

“Come on. Right now. I wasn’t asking you, Charlie.” She held her arm out.

I grabbed her soft hand and my heart jumped.

“Three. Two. One.” She counted us in and I pushed a little bit, not trying too hard. Her arm didn’t even move. I frowned and decided to just beat her. I put more effort in and that made her hand move a bit, so I piled the force on. But suddenly, it stopped moving a quarter of the way back.

I really pushed and my elbow came off of the table. All of the sudden Eva’s left hand pushed it back down. My left hand, unfortunately, was gripping the table in an attempt to provide leverage.

I looked up, sweating, and saw her smiling at me.

“Wow,” she pushed my hand all the way down to the table in one easy motion, “you really are so weak!”

She laughed her sweet laugh as I sat there humiliated, still holding her hand, getting more turned on for some reason. I had no clue what to say and a million thoughts ran through my empty head.

Suddenly, Eva grabbed my other hand and pinned both of my wrists on the table. I barely tried to move them, but I knew even if I did, it wouldn’t have made a difference.

“And to think that I thought moving in with a man there would be some protection for me!” She laughed again. “But it looks like I’ll do the protecting in this apartment. That’s okay though.”

“I’ll still protect you!” It was a stupid thing to say with my hands pinned down. I was rock hard under the table, probably harder than I’d ever been.

“Aw. I’m sure you will, cutie.” She scrunched her nose at me. “You’re sweet for thinking that.”

For some reason, at this moment, I was struck with a sudden, overwhelming urge to kiss her as she pinned my hands down and laughed at me. She stared at me like she felt the same thing too. But it made me scared and I just looked down.

She held my hands for another eternity before releasing them.

“Okay. Pushups.” She stood up and looked at me expectantly. I was still fully erect in my sweatpants.

“I… uh… I can get to them later; I need a minute.” I felt my face flush.

“No, you’ll do them now, like I said.” I felt her staring at me again.

I knew I had to do them so slid from the chair to the ground as quickly as possible and tried to adjust the waistband of my pants to hold my dick. I heard Eva pull in her breath slightly as I did this.

3

I could only do 15 pushups, and as I sat there on the floor panting Eva reminded me that I needed to do the dishes and then left for the gym. I said I’d do the dishes and go on a run or a walk as she went out the door.

As soon as it shut, I got up and bolted to my room. In my closet shelf was a box I had been sure to carry in myself on June 1st. I took it down and opened it.

Inside lay the spoils of living by myself for 2 years—a pleated skirt (my favorite), cheap but cute panties from Amazon, thigh high socks, tights, a dress, and a few loose, thin blouses.

I have loved crossdressing since, well, since before I can really remember. It was arguably my first fetish. I also hated it.

When I had lived on my own in Baltimore, I bought all these clothes and loved it and dressing up. But I always ended up feeling so ashamed, I pledged that when I moved and got a roommate, I would throw them out and use my new roommate to hold myself accountable to the norms of society.

But, like any crossdresser could tell you—purging just doesn’t work. Maybe you can make it a year, even two without feeling any urges. But you’ll want too, need to, dress up again, cave, and buy clothes and revel in it.

So, rather than throwing out my fourth skirt in four years, I had ultimately decided to keep my clothes this time. I’d just put them in a box and leave them there and I could forget about that chapter in my life.

But living with Eva had made it hard. I started watching porn I said I wouldn’t watch again. I started fantasizing about being pathetic, about being feminized, about being whatever someone else wanted me to be. And now, after getting proven to be so thoroughly weak, I just had to dress up again. At least jerk off in some panties. Just one thing to revel in how weak, submissive, and feminine I had just been.

I started by putting on a pair of panties, but because it was late summer I hadn’t shaved my legs. I looked in my mirror and felt disgusting, so I took them off and put on some tights and my skirt and a blouse. I looked in my mirror again and saw someone cute and small, someone who Eva had just held down and overpowered. I spent some time playing with my skirt, watching it move in the mirror and float in the hair before I finally reached under it.

All of the sudden I heard the door bang open. I froze, thankful that my door, which was open a crack, didn’t show this part of my room.

“Come on!” I heard Eva say. “We have like 30 minutes until he gets back. I want you to fuck the shit out of me. NOW.”

I heard a man laugh and say something soft and low and then I heard kissing. It moved into Eva’s room, right across the wall from my headboard, as I stayed frozen still in a blouse and skirt with my hand under my tights. I was so unbelievably hard and horny but I didn’t dare move. It got quiet, aside from Eva’s occasional moan, beautiful even from a distance and through a wall.

Before long I started hearing Eva’s headboard begin rhythmically slamming into the wall. Moans started coming in from across the apartment and through the wall both our beds butted up against, now louder and with more regularity, making me realize just how thin the barrier between our beds was. I cringed when I thought of how much porn Eva must have heard me watch but those thoughts were drowned out by the noises coming from the other side of the wall.

“Ohh… fuck Jack.” I heard it clearly now as the pound kept going steady. Jack, whoever he was, was clearly a force of nature. I crept over to the wall and put my ear against it.

“Oh my God Jack! You fuck me so good!” This time I heard him answer her exclamation with a couple of grunts and my hand, which was still down my skirt, started moving back and forth.

I listened to the rhythmic thud… thud… thud… and almost forgot to play with myself as I strained to hear any sweet sounds Eva made, anything that would bring her perfect body and her shampoo and her hands pinning down mine back into my head, riding on some imaginary cock even though all I cared about was her face, her eyes closed, smiling in pleasure, lightly moaning, reaching down to touch me…

I was about to cum to this thought when the pounding turned up a notch to wall-shaking, the man grunted, and then everything stopped. I stopped moving my hand instantly in the silence and my cock squirmed as a little dribble came out from my ruined orgasm. I heard them moving, obviously putting on clothes, and I crept back behind the door, wondering why the fuck I hadn’t even taken off my skirt.

“That was fun, Jack. I’ll walk you back to the subway stop.”

I heard the door open and close.

4

Although the logical thing to do would be to take off the skirt and the blouse and try to come up with some sort of solution to the conundrum I found myself in, something took hold of me and I crept out of my room. I stood in the living room and the smell of sex brought me to Eva’s door. I peered through its slight crack. I just had to see where those sounds, that beautiful thing of Eva in ecstasy, had just happened. Smell it. Feel it. Understand it.

In the darkness of her room I saw crumpled piece of lingerie. Taking one last look at the safety of the living room, I stepped through Eva’s door.

Instantly I was overwhelmed by its smells. I had smelled Eva and I had been in her room before but this was something else—like an overpowering suggestion she was still here. Then I saw how her room, usually so tidy and neat, was messy and scattered. I thought about what had gotten Eva, usually so controlled and level excited enough to disregard herself and her standards like that.

Finally, I reached the lingerie. I bent down and picked it up and looked at it.

As if I expected anything else, it was classy and cute and sexy all at once. A black lace onesie piece, I couldn’t help but imagine in on her body. I saw dark stains near its chest and brought the whole thing up and breathed in. It was salty, sweet, Eva, somebody else, the lace of the fabric, the picture of her wearing it, the idea of wearing it—it was all too much and I started furiously stroking myself, mouth open and lingerie held up to my face.

Suddenly, right as I was about to cum, I heard the front door slam open and Eva walk in. They couldn’t have been gone for a minute. I heard her stride across the apartment and suddenly there she was, standing in the door, seeing me in all my perverted glory.

If the image of her roommate crossdressing, hand on his dick while holding her lingerie, phased her at all, she didn’t show it. She just stared at me with solid, unmoving blue eyes.

“Yup! Your phone’s in here! Just go get the elevator again and I’ll be right back out!” She shouted as she walked over to an iPhone that was laying on the floor and grabbed it. The whole time, her eyes never left me. I stayed frozen. I prayed with all my heart that I could be invisible, just this once. She walked over to me and took her lingerie from my hand. She looked it up and down, and then looked me up and down, too.

“You. Don’t move.” I didn’t move as she walked around me. Suddenly I heard her whisper in my ear. “When I get back, you had better be ready for us to have a talk about this. And clean up the mess you made in here.”

Then she was gone and the front door shut again.

Although I had literally only picked up and put down her underwear, I furiously spent the next few minutes tidying up her room—making her bed, picking up clothes, tidying up her desk.

After that, I went back into my room and put my girl clothes away. No thoughts about even trying to finish myself off in the skirt this time. I looked around my room and straightened that up too. I was like I was in trouble with my mother all over again. My heart was pounding and my head was spinning. I could only imagine what would happen. Surely, I would have to move out. She would tell Hannah, who would tell all my friends from home, and they would tell everyone, and everyone in NYC would know how much of a perverted roommate I was.

I was starting to tear up when I heard her walk back into the apartment. I stood up to go say something to her but I didn’t know what to do. I heard her walk into her room and move around for a couple minutes. Then I heard her come to my door and open it.

“What do you have to say for yourself, Charlie?” I looked up and she was staring at me with her arms crossed and her eyes like ice, boring into me.

“I don’t—”

“You don’t what? You don’t think I get it? You don’t what?” Her tone was like a knife in my soul.

“Eva, I’m so sorry. I just—”

“You just? This is that simple? Just a misunderstanding? Something like that?” She walked into my room and stood in front of where I was sitting on my bed. “Stand up and look at me, Charlie. At least take some ownership of this.” Her voice softened just enough that I was relieved to do what she asked.

“You think this is acceptable? That this is okay? This is something remotely appropriate to do?” Her anger was palpable and it made me start to shake.

“No, Eva. I’m sorry.”

“I trusted you like a brother, he turns out to be a pervert. Isn’t that right?”

My cheeks were hot and I stared at the floor.

“Look at me, Charlie.” I looked up at her and I could feel tears welling in my eyes. She looked sad. “Are you a pervert?”

“No! I’m just, I guess I, I thought… I’m…” I stalled out and she let me dig myself deeper.

“So what would you call a boy who jacks off in a skirt, smelling their roommate’s used lingerie? Moments after she was fucked in it? What would you call someone who can’t resist the smell of a real man and woman, who spends all his time just jacking off to porn? Is that a normal person?”

My cheeks had holes burning in them and I started crying and looked away from her.

“No. I didn’t say you could look away from me. I didn’t say we were done.”

I looked back up at her, crying, and suddenly she stepped in closer to me and gently caressed my check with her hand.

“Poor little Charlie. What’s wrong with you?” The blue in her eyes was overpowering and I had to focus not to look away and I managed to stop crying. She was gently rubbing my cheek and I started to answer her.

“I just think that—”

“Shush, Charlie. Don’t embarrass yourself. This is the problem. You don’t think.” She stepped closer to me, close enough that I was breathing her breath. I backed up and she followed me, still looking into my eyes. I did it again and I hit the wall in my room and she stood right in front of me and I could hear her calm breathing and smell her hair and I closed my eyes again.

“No. Look at me.” More beautiful, hypnotic blue.

“You don’t think. Poor boy. He’s too horny, right?” She paused and waited for me. I nodded and suddenly she grabbed my cock. I sagged down to where I was basically sitting, leaned against the wall, with Eva crouched in front of me.

“Too horny. Look how hard you are, and I’m in here yelling at you. You’re just a pervert, aren’t you? A pervert who can’t help but turning off his brain whenever a girl walks by, right?”

I nodded again as I focused on her mesmerizing eyes and the feeling of her stroking my cheek and holding my cock. It was all too overwhelming.

“Little perverts like you need to be told what to do, or else they break rules, right?” I nodded, but her hand slipped down around my throat and tightened just a little. I felt a rush of blood to my head and could barely think as it turned me on like nothing else.

“Time to speak, little boy.”

“Yes, Eva.”

“Yes, what?”

I could not, for the life of me, remember what she had been saying. Her hands around my neck had wiped by brain clear of any coherent thoughts. I just looked at her and looked down. She quickly tightened her grip around my throat and sighed. She took her other hand off my cock and lightly slapped my face.

“This is what I’m talking about. You’re a pervert who needs to be told what to do. You need me to tell you what to do. Maybe even help you have fun. But from now on, you’re going to listen to me. It’s what you need. It’s what makes sense. Right?”

“Yes, Eva.” Another slap.

“Say more, pervert. You’re not a ‘yes’ machine.”

“Yes Eva.” I tried to think as she started stroking my cock again and her hand alternated from tracing my neck to rubbing my check. “I need you to help me, to tell me what to do. I need you to help me think and keep me from being a pervert.”

She laughed.

“Maybe we won’t keep you from being a pervert. I don’t think that’s possible But I like the innocent thought, cute boy. What else is there?”

She started stroking my cock faster. I couldn’t believe she was touching me and I tried hard not to explode right then.

“I’ll listen to you, Eva. I want your help. I need to know what I should do. I’ll do what you say. I’ll be good for you and make sure you’re happy and I want to be good for you.” She smiled as that all spilled out of my mouth and my heart jumped out of my chest.

“Good boy. That’s a good start… You know, I bet you even want to suck some cock for me.” As I opened my mouth to protest she quickly slid a finger in my mouth and pushed it around my mouth. All I could do was just suck on it and look in her eyes. She fucked my mouth with her fingers, slowly at first, and then faster and faster as she stroked my cock. In no time, I was spurting cum all over the floor and her hand and my sweatpants. She laughed and held her hand up to my mouth.

“Lick it clean.” I instantly leaned forward and sucked her hand clean of my juices. It tasted bitter but not altogether horrible.

“Good boy. I knew you liked to listen from the moment I first set eyes on you.” She stood up and looked away from me for what felt like the first time in a thousand years. It felt like I had been released from a spell, but also somehow empty without her looking at me.

She walked to my door and then turned around.

“Starting tomorrow, there will be some changes. We’ll start easy, but I want you up at 8am sharp making me breakfast. And no fucking porn or jerking off tonight. I know it might be hard, but if I hear anything other than peaceful sleep coming from this side of the wall, I am going to bring hell down on you like you wouldn’t believe.” She smiled at me. “Good night little pervert!”

She turned the lights off and left as I crawled into bed and slept better than I had in years.

Source: reddit.com/r/Erotica/comments/plqu1q/roommates_femdom_mf