In Love with my Roommate Ch. 01

"So, uh, do you mind if I wear a dress?" Alex asked with trepidation.

"Not at all! Wear whatever you're comfortable with. You're in university now! You're free!"

I thought my speech was rousing. He smiled again and dug into a new box. He pulled out a forest green dress. Standing up, he unzipped his lime green hoodie and took off his black tank top. Standing there in just his panties, I took the time to admire my roommate. He had a very delicate and feminine frame.

He had freckles on his smooth and hairless chest with two subtle nipples. Even I had to admit that he had a really nice ass as well. He put the dress down and stepped into it, sliding it up and over his hips, then over his shoulders. It was a halter dress that had a zipper in the back and cinched at the waist. It flared outwards from his feminine hips and fell almost to the floor. He turned his back to me and asked me to zip him up.

Putting my hand onto the zipper and tugging upwards, I completed the look. He turned to look at me, and my jaw opened. Wow, he looked good! The dress complimented his feminine hips, and his butt. He did not have the bust to fill the dress out, and his rat's nest of a haircut gave him a hard rock edge that made the look very androgynous. It was a good look.

I slipped on my brown loafers, and he put on a pair of grey and blue ballet flats that he produced from another box, and we were off to explore Ottawa.

We walked for a grand total of ten minutes before stumbling upon a marketplace of bars and clubs. We had moved in on a Wednesday night, and the clubs weren't exactly hopping, so we settled on a mid-tier pub named after a generic Irish fellow. When the server asked for our ID, I saw Alex bristle. She looked at the photo of Alex and then at the man in a dress in front of her and handed him back the card. Motioning for us to follow her, we moved deeper into the pub.

I ordered a glass of red wine and a side of cauliflower bites. Alex ordered a cosmopolitan and some fruity dessert that I had never heard of. While we were waiting for our food, I had a million things going through my head. I wanted to break the ice with Alex and let him know that I was going to be a chill roommate. "So, do you wear dresses all the time? Or is it just a Wednesday thing?" I asked.

"Well, that depends. Do you want the full story or the condensed version?"

"Honestly, I'd love to hear the full story. In the fine-arts world you don't get very far with a closed mind, so consider me all ears!"

Alex stopped to collect himself and took a deep breath.

"Well, then I guess you can start by calling me Alexa. My parents haven't come to terms with it yet, even though it's been years since I've dropped the bomb on them. But I've known that I was a woman since I was little. And moving to Ottawa presented me with an opportunity to finally get the medical support that I needed. Treatment is covered in this province and in Québec, but it's a lot harder to get in Manitoba. That isn't to say that Winnipeg doesn't have a super supportive community, but it's a different mentality, you know, especially if you're from the French-quarter?"

I just nodded along. This was a lot to take in, but man, this guy was brave. Wait, this girl was brave.

"So uh, it's a thing now, and I should ask, what are your pronouns?"

"Oh, uh, you can call me Alex or Alexa. I don't really care if you call me 'he' or 'she' yet, because I haven't started treatment yet, but in French I'd prefer to be called by 'elle'. But tomorrow I have an appointment to start hormone therapy, and at that point I'd like to be referred to in the feminine in both languages."

"Alright," I said. "Got it."

"So, you're going to transition. That's awesome!"

"Yeah, I've got an appointment in two days! I am both nervous and excited. I have been dressing as a woman for the last two months, and if you're cool with it, I will probably stay dressed as a woman now on a go-forward basis. It's who I am."

Well, that explained why he was in a guy's dorm. He had zero parental support and hadn't met with a medical professional yet to be considered a woman.

"Hey, I have no problem with that whatsoever!" I responded. "One of the playwrights we studied in Cégep was a Russian named Stanislavsky. He believed in method acting, where you cannot be the person you want to become unless you live their movements and life as they did. So, if you truly are a woman, just consider this a return to form."

"Thanks for the support, Pierre. But uh, will you have any trouble sharing a bedroom with a woman?"

"Nah, I don't think so. If you want some private time just let me know. But I'm pretty flexible. I intend to join the theatre group on campus, so that should occupy my time."

We continued talking for another two and a half hours. I ordered another two glasses of wine, and Alexa ordered another two cosmopolitans. By the time midnight rolled around we were both pretty drunk. All the exercise today coupled with our limited appetites meant that we were both a giggly mess when we paid the cheque to the server and left.

It was a nice summer evening and enamoured with the lights from the Parliamentary district and the monuments, Alexa slipped her arms into mine and we walked back to our dorm. When we arrived back at the residence, I was JUST sober enough to be thankful for those two technicians that had fixed the elevator. Miracle workers, both of them.

By the time we had made our way up to our room, a wave of exhaustion had passed between us both. I was ready to hit the hay and looking at Alexa I could tell that she was as well. We both brushed our teeth in silence, before I left to get back to our shared room. I kicked off my shoes and peeled off my shirt and pants. I usually slept naked, but considering the present company, I figured I would leave my boxer briefs on. It was the least I could do.

Standing there in just my underwear, I threw an additional blanket onto my bed and added the pillow. I had unpacked all my clothing earlier, but my bedsheets were the last item to store away. Alexa, or her parents, had already made her bed. When I turned around, Alexa had come back into the room. She had shed her shoes and turned her back to me.

"Pierre, will you unzip me?" she asked in a voice that conveyed exhaustion with a hint of intoxication.

I put one hand on her exposed shoulder, and with the other tugged the zipper down her back. She pulled the halter over her head and let her arms slip out of the dress. It cascaded down her lithe form to pool at her feet. In my intoxicated state I looked down at her ass, encased in her powder blue panties.

Turning around she wrapped both her arms around my torso and embraced me in a hug. I couldn't help but get a slight erection as her tummy rubbed into my package.

"Thanks for being so understanding about this," she said to me.

"No problem, Alexa. We can chat more in the morning."

"Bonne nuit Pierre," she spoke.

"Toi aussi, Alexa," I responded.

I watched her climb into bed, checking out the way the panties covered her ass, until she flicked the switch to turn off the lights.

She must have fallen asleep pretty quickly, as her breathing was rhythmic and calm. However, I couldn't sleep. Was I gay? I was totally turned on by my roommate - and it was day one of university. I had a TON of questions. Eventually, I fell asleep.

I woke up to the sound of parents and students in the hallway outside of our dorm banging boxes and shelves into doorframes. It was clearly day two of move-in. I stood up and stretched, looking over at Alexa, still asleep in her bed. Her reddish hair was splashed over her pillow. She looked cute.

That thought gave me a weird feeling in the pit of my stomach.

I threw on a green dress shirt and my jeans from yesterday. I paired them with a pair of black loafers that were my comfy walking shoes and set off in search of the school cafeteria. I debated asking Alexa if she'd like to join me, but there would be plenty of time for that throughout the school year.

I grabbed my student card, that also contained my meal plan, and set off in search of the cafeteria. The minute I was out in the fresh air, I whipped out my cell phone and dialed my sister. It went eight rings before she picked up.

"Hey stud, how's university? You get laid yet?"

"Stéphanie, how did you know you were a lesbian?"

"...uh, okay. Um, this got heavy quick. Are you somewhere you can talk?"

"Yeah, I just swiped into the cafeteria. I'm alone at a table. Everyone else is either exploring or moving in, I'm basically the only one here. Also, if you hear crunching, I'm eating a waffle."

"Right. Well, I've always known, Pierre. Like, when I looked at a woman when I was a teen there was always an attraction there. I never felt drawn to men, or anything really masculine, you know? Why are you asking? You didn't hook up with a guy, did you?"

I took fifteen minutes to explain the situation with Alexa, and that when we had walked home together arm in arm it felt good, and then when she had hugged me, I became aroused. I know it sounds weird, but my sister was studying to be the doctor in the family, and we had more than enough love between us to share this detail without judgement.

"So, now I am worried that I'm gay and I am just generally confused right now," I finished.

"Alright, you're in fine arts, so I can't imagine being gay would put you at any significant disadvantage," she started. "And also, how could you possibly be gay if you're attracted to a woman?"

"But she hasn't even started transitioning yet!"

"So? You're already calling her by female pronouns. In your head, do you see her as a woman, or a man?"

"She's a woman."

"Exactly! Gender is a social construct, Pierre. If she's dressing and acting like a woman, and she identifies as that, then she is one."

"Makes sense. But what's a social construct?" I responded.

"Attend your lectures. You'll learn. Listen. Don't overthink it. Someone in my undergraduate degree was with a man who was transitioning from being a woman. She told me that she loves hearts not parts. Don't think about what's in their pants. Think about them as a person. The rest will take care of itself."

"Thanks sis, you always know what to say."

"It's what I do. Listen, before I let you go, one more thing."

"Sure, shoot?"

"She got a nice ass?"

I laughed into the microphone.

"Ha, yeah. She really does."

"Go for it then little bro. You always were an ass man."

"Ugh, bye Stépanie!" I said and ended the call.

God, I loved that woman. But some days she was absolutely too much to handle. I couldn't wait to meet Monique. I wanted to see what kind of woman could make my sister interested enough to settle down even slightly.

I finished my waffle and prepared a coffee to go in my travel mug. Feeling a million times better about myself, and about how I was going to approach living with Alexa, I walked back to my dorm in quiet contemplation. Even though I had done the same thing the day before, I watched the spectacle of parents and new students moving into the dorm with a mix of fascination and consternation. I saw that a lot of people only had one parent there, and some of them didn't even have that. I realized that not everyone had as loving and supportive a family as me - including my roommate.

When I walked back into our dorm, Alexa was in the bathroom, swearing loudly at something. I put my coffee down on our kitchenette counter and kicked off my shoes. I tapped on the bathroom door and asked if everything was alright. "No. Nothing is right. I cannot get my makeup to work!" she exclaimed.

"Uh, do you want a hand with that?" I asked her.

The bathroom door opened to reveal a partially dressed Alexa. She had clearly taken a shower, and her auburn tresses were put up in a towel. She had a pair of yellow panties on her hips with charcoal grey pantyhose pulled up over her feminine hips and trim waist. Even though she didn't really have breasts yet, she had a yellow lace bralette on her chest as well. She looked sexy, and I felt my heart catch in my throat.

"I have never done this. On my last day before moving here I dropped some money on some cosmetics with the intention of living full time as a woman. I never thought that I'd have to learn how to use it!"

I burst out laughing. She had applied her contour and her bronzer first, and she looked like a cartoon character.

"I played some of the boy and girl parts of Ophelia in my Cégep's production of Twelfth Night and did everyone's makeup when we did the Mozart Opera Rock. Let me give you some pointers."

She playfully pouted with me and hopped up onto the counter, as I took one of the wipes from her bag and washed off her cheeks and eyes. I positioned myself in-between her legs so that I could work on her face.

"So, you should start off with a primer. I like gels, but you can get them in spray form too. Sprays go on easier, and people use them in theatre all the time." I added a dab of primer to her forehead and to her nose. "Primers cover up any big pores or fine lines - like the one on your forehead - so that it doesn't look like you applied your makeup with a marker." That line made her chuckle.

"Next, you should even out your face. You can use either a foundation or a concealer. A foundation is meant to even everything out and cover up imperfections. A concealer does the same thing, but in a smaller space; like if you want to cover up acne or a birthmark. I'm going to give you a quick layer of foundation to just even out your face."

"So, once you're done with your foundation, you can accentuate a particular feature if you want. Like, if you want to accentuate your gorgeous blue eyes, you could apply a shadow, or if you want to frame them, you could apply mascara or eyeliner. Personally, now matter what you do you're going to be beautiful."

I could see her lighting up under my compliments. I didn't mean to flirt with her. But, the freckles, and her smile and her blue eyes just brought it out of me.

As I brushed over her face, I could see her looking up at me. I smiled at her and told her that I was going to turn her into a model. That prompted another chuckle from her.

"So, before we do anything else, what look are you going for today?"

"Well, I wanted to wear a cute blue and red summer dress today. It's probably one of the last nice weeks we're going to have before fall, so I wanted to try this look on."

"Okay, so we'll give you a nice femme look that will match your blue eyes."

I gave her a bit of highlight to bring the lighter parts of her face forward and added a bit of blue eye shadow that would look nice with the dress hanging on the back of the bathroom door.

"Lastly, you have really nice lips. You should pick a nice lip gloss, or if you want to really emphasize the look, you can pick a pink or light red matte lipstick."

"Well, if I wanted to impress a guy, what would you recommend?"

I stammered, "Uh, probably a light red matte."

She rummaged around in her bag and found a pink matte. Popping off the lid, she applied a quick layer to her lips then blotted on a piece of toilet paper. Hopping off the counter, she took her dress off the hook. She slid her feet into the dress and pulled it up. It had five or six buttons in the front and Alexa made quick work of buttoning them up.

I took the chance to check out her butt when I thought she wasn't looking, though I am pretty sure that she caught me looking in the mirror. God, she was beautiful. I'm happy I told her I thought so.

"So, how do I look?" she asked, once the dress was secured.

"Well, aside from your hair still being in a towel, you look positively beautiful," I spoke.

"Aw, thanks!"

I left her in the bathroom and went back to our room to scroll through social media. She emerged fifteen minutes later looking like a vision. She was dainty and petite, and the red hair coupled with the red and blue in the dress was definitely something else, but she looked gorgeous. Yep, it was confirmed. I was attracted to my roommate. Gods help me, Stéphanie would never let me live it down.

We spent the day with Heather and Michelle, the two nursing students living on our floor, and got to know some of the other students too. They had come from pretty much everywhere. The school did a good job of mixing us together, while making sure that there really weren't too many unilingual anglophones on the floor that wouldn't understand the rest of us talking smack about them.

Around six, our Residence Advisor gathered us all in the common room to lay down some ground rules. No parties, keep it down, let everyone study, et cetera. Her name was Karleigh, and she let us all know that it was tradition for first years to all go to Gatineau on the Québec side of the river for their first night and to party it up in the clubs. There was a murmur of approval from everyone in the common room. It appears that our first real night of university had begun.

Around ten that evening, I found myself in the passenger seat of a cab heading over to Gatineau. Michelle, Heather and Alexa had managed to squeeze into the back, leaving me to direct the cabbie to the bar district. I guess everyone thought that I knew my way around because I was Québécois. Little did they know that the last time I had been to Gatineau was when I was ten or eleven for a class trip. Thankfully, the driver knew enough about the city to get us where we needed to go.

He dropped us off outside a two-story club near the river, and Heather gave him a twenty to send him on his way.

There was a short line-up outside of the club. We all flashed our ID to the bouncer. He did not even give Alexa a second glance, despite her driver's permit being clearly marked "male," and here she was looking gorgeous in a blue and red summer dress with her auburn hair done immaculately. Gatineau very much lived up to its reputation. Meanwhile, I waited for them in white khakis and a pink dress shirt with the sleeves rolled up.

Heather, Michelle and Alexa and I had become fast friends. The three girls had spent a bit of time touching up each others makeup and doing their hair. The result was that the shared bathroom of Alexa and I looked like a cyclone had hit it. The upside was that she was feeling a Hell of a lot more like a woman, and I had two other women walking around in club dresses. Alexa only had summer dresses, but given her body, she could pull the look off in a club.

We wound up forking over an absurd amount for cover charge, and Heather immediately led us over to the bar to take some vodka shots. The lights were pulsing, and the bass was heavy with the sound of European dance music and club remixes. Yep, we were definitely in a Québec club. We all took our vodka shots and chased it with a tequila that Michelle had decided was "absolutely necessary" to celebrate our arrival in Ottawa.

Sufficiently liquored up, we made our way over to the dance floor. Heather and Michelle were both wearing standard little black dresses that emphasized their asses and left their cleavage on display. While that would ordinarily attract a lot of attention, the amount of first year students here meant that everyone was pretty much wearing a deviation of the same outfit. That went double for the men, who were all wearing some combination of jeans and a striped shirt with a baseball cap. Evidently, Ottawa didn't do deviation.

Being no stranger to nightclubs in Québec City, I set out to dance with my new friends. Heather, Michelle and Alexa and I all danced together, letting ourselves loose with our newfound freedom. A few guys cautiously approached Heather and asked the blonde to dance. She accepted. Another guy asked Michelle to dance, and the Caribbean beauty went to dance with him. That left me alone with Alexa. She was clearly not comfortable on the dance floor. I mean, it was her first time as a woman standing on a dance floor. But I thought back to what my sister had told me: she's just like any other woman, just go with it.