Roommates Pt. 01-04

I wrote this a few years ago and posted it on reddit once, but never got around to publishing it more seriously. I'd like to post it here and to see if other people enjoy it. Hopefully, that would give me some motivation to keep the story going. I had plans to continue but it's too easy to be lazy! Please let me know what you think, and let me know if you're interested in reading more!

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 1^st, 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 friendly, fun, and smart. She told me that Eva could wingman me and would stay up late with me, talking through my non sequiturs and dollar-store philosophy. 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. When she did that, I always slammed my laptop shut, red faced and grabbing at 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, inevitably 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. I remember her vaguely leading me to the bathroom, helping me wash my face, the look she gave me as she pulled the covers up to my chin that made me feel like my heart beat slowly and the world was all right there in front of me.

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). She was in amazing shape, toned and lithe. I couldn't help but stare at her butt every time she walked away from me, and she surely knew how hard it was for me to avoid looking at her perfect boobs when she was facing me. She was, without a doubt, the most beautiful woman I had ever talked to.

This fact of perfection 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. 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 couldn't quite ask anyone out on my 56^th 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 considered me, to be honest. I mean, I think I'm good looking. I'm 5'10", 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 how could I ever think she'd look twice at me? 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 in it, but perched on the very edge of the couch and leaning into the armrest--basically, I was as far away from her feminine side of the couch as I could be. I know some of you will get 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 see staring at you, I instantly looked away.

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

"Hey Charlie," I heard her speak and tried to pretend none of that happened. I nonchalantly, nervously glanced over as she asked me "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, comfy couch; are you actually not going to use it?"

As she said that she was laying down, stretched out, with a blanket on. She took up a huge majority of the couch, with her feet inches away from my thigh. I could feel the warmth coming off them, feel how scared even her feet made me feel. 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, "is the shy boy afraid to come sit by the girl?"

"I-I'm not afraid, it's just that... I don't want you to..." My cheeks flushed.

"You're seriously scared of me? 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 you feel awkward. Or uncomfortable"

"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, only knowing how absurdly beautiful 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, how lonely I was, how desperately I always needed her touch. I realized Eva was waiting for me to answer.

"Yes," I spoke more softly and admitted more pathetically than I thought I ever could, "I could use some cuddles, please, Eva."

My cheeks flushed and it felt humiliating, but somehow wonderful to say.

She lay back down on the couch and, eyes still locked on mine, 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.

"It's okay to like cuddling like this, Charlie. I know it's what you needed, deep down." When I didn't say anything I felt her stop touching my hair. "Isn't it?"

"It's okay to like cuddling this. It's what I needed, deep down." As I said the words back to her, a warm relief spread up my body and she resumed running her hands through my hair. It truly felt like heaven.

"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, Eva." 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. Chivalry is not dead).

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 woke 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 stared at me. I tried to stare back, with some success. But her icy blue eyes made me feel smaller and smaller until I looked down at my plate and kept picking at the remnants of my food. 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 harshness 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. Time to be a man" She held her arm out.

I grabbed her soft hand and my heart jumped. I tried hard not to make it obvious how happy her simple touch made me.

"Three. Two. One." She counted us in and I pushed a little bit, not trying too hard. Of course, I didn't want to embarrass her. Her arm didn't even move. I tried a little more, but it was like pushing against a wall. 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 it suddenly stopped moving a quarter of the way back.

I really tried with all my might and my elbow came off of the table, even as I watched her hand remain still. 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 as I yelped in surprise, "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 sweatpants to hold my dick. I heard Eva pull in her breath slightly as I did this. I blushed harder and looked down and when I glanced at her for a moment she was looking at me strangely, thoughtfully.

3

I could only do 15 pushups, and Eva laughed when my arms gave out at the last one. 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 1^st. 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 skin-colored tights, a dark checkered skirt and a pale white blouse. I looked in my mirror again and saw someone cute and small, someone who Eva had just held down and overpowered. I felt warm and happy and couldn't help but smile. I spent some time playing with my skirt, watching it move in the mirror and float in the air 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 from the living room into Eva's room, right across the wall from my headboard, as I remained frozen in a blouse and skirt with my hand under my tights, gripping myself. I was so unbelievably hard and horny but I didn't dare move. It became 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 happened. Smell it. Feel it. Understand it.