The Roommate Ch. 01


I had only just moved to the city, moving into an apartment with my best friend from school, Ryan, when he had got a job offer in another city. Ryan hated his job and the offer was too good to refuse, so he had to go – and I had a month to find a new flatmate. But three weeks passed, and still no one replied to my online flatmate wanted ad. I was starting to get concerned. That was until I got a text from Monica.

I wasn’t sure if I wanted to get a girl in – what if it got awkward? I’ve got a long track record of getting it wrong with girls, I’ve often got the wrong message and ruined many good friendships with women because of this. Nonetheless, I desperately needed someone else to move in as I wouldn’t be able to afford the rent by myself, so I invite Monica to check out the room.

The following day, I spent all morning cleaning the house, wary that no one woman would want to live in the pigsty Ryan and I had happily called home. The doorbell rang just after midday, and I rushed to the door, stubbing my toe on the vaccum cleaner I had failed to put away. Shit, I murmured to myself, chucking the vaccuum cleaner behind the door. The door bell rang again.

I opened the front door and felt the air sucked from my lungs. Monica was gorgeous. Her shoulder-length black hair framed a soft face, her eyes dark and her lips a rich red. She wore a black dress, low cut, her pale arms exposed. Her legs wrapped in black tights, her feet in stylish ankle boots. Immediately I knew I would fall for her.

“Sorry I’m late,” she said.

“Hey, you’re not at all, come right in.”

I showed her around the house, her room, the living room, the kitchen, the bathroom. She said it was what she was looking for, close to town, decent sized, a lot of natural light. She had only just moved to the city, and was looking for a new job and new friends.

“I’ve just got out of a long relationship and I figured I needed a new start,” she told me over coffee on the deck. “It will good to meet new people and move on from the past.” I told her I was new to the city too so we’re in a similar situation.

Monica moved in one week later. We hit it off quickly, sharing a lot of interests and she got my sense of humour.

After a few drinks one Friday we started talking about past relationships.

“So did you have someone in your last city?” She asked.

I told her I’d been single for a few years, apart from a few one-night stands I’d struggled with women recently. Shit, I’m hardly playing it cool, I thought, so figured I should change the subject.

“How about your last relationship, if you don’t mind me asking?”

“It’s xslot alright,” she replied. “We were in different stages in life, we wanted different things. I wanted to travel, go to new places, while she was settled with her job and was keen to stay where she was.”

Did she just say she?


“Oh, yes, she, I’m a lesbian. I hope that’s not a problem?”

“Oh, no, that’s fine. Perfect in fact.”

“Perfect? Um, why?” She seemed uncomfortable.

“Oh, no, not like that. It’s just, well…”

“Well what?”

“Well, when I first saw you I thought you were gorgeous. And I had hoped you wouldn’t be.”


“Because I didn’t want to fall for you. I needed a flatmate and I wanted us to get along, without me falling for you and ruining everything. But I think now I might have made it awkward anyway!”

“Of course you haven’t,” she reassured me. “I’m used to having attention from guys, and having to let them down. You’re such a sweet guy I’d hate things to get awkward with us. I know I’ve only known you a short time, but I feel I can really trust you. I can see us becoming really good friends.”

“Glad to hear it.”

I was relieved. I really didn’t want to have to find another flatmate, and Monica had become a good friend – and I didn’t have many of those in the city.

The next night, we were having a few wines together again. We didn’t know many people and it was cheaper to drink at home. Monica was wearing the same black dress she’d worn when I first saw her.

“I like that dress,” I told her.

“Thanks,” she responded. “What do you mean you like this dress? You know I’m gay, right?”

“Oh, of course! I mean you look great in it. It was the one you wore when you first came here, and you looked gorgeous. Sorry if that across weird, maybe I’ve had too much wine!”

“No no, sorry for taking it the wrong way, thanks, I’m rubbish at taking compliments. It’s my favourite dress, I’m glad it suits me.”

The room went quiet for a moment, a weird tension remaining after my awkward compliment. But it was only to get more awkward.

“Would you like to try it on?”


“The dress, would you like to try it on? I mean, if you like how it looks on me, I’d like to see how it looks on you.”


“Because it would be fun. Have you worn a dress before?”

“No,” I lied.

“You’ve got the figure. I mean that as a compliment.”

It was a weird compliment. Monica and I had similar builds, not too skinny, but slim.

“Alright, let’s put it on then.”

“Wow, you’re easily convinced. xslot Giriş Alright then, girlfriend.”

She unzipped the back and dropped the dress to the floor. She stood there in the middle of the living room, exposed apart from her matching maroon bra and panties, and looked up at me.

“What are you looking at?”

“Nothing, sorry.”

“Well take off your clothes.”

I lifted my shirt off and wiggled out of my jeans. She stepped out of her dress, and kicked it up at my from the floor. I awkwardly stepped into the dress, and pulled it up. Monica reached around behind me and zipped it up.

“Fits perfectly. A little too well. You’ve even got the hips for it. But you’re a bit bare up here,” she said, fondling my chest.

“We’ll have to sort that out,” she said.

She went to her room, leaving me standing there emasculated in the living room. She returned with a padded black bra.

“Really? I’m not wearing that!”

“Come on, you look silly otherwise.”

“I’m going to look sillier with it.”


I relented, lowering the dress from my shoulders so Monica could put on the bra. She slipped in some extra padding to give me two modest breasts.


“Perfect? I feel stupid.”

“Well that’s only because I haven’t done your make-up.”

“No no no, that’s not happening!”

“Please! It’s just you and I, no one else needs to know. It’ll be fun. Don’t you trust me?”

“Of course I do. Fine then.”

She led me into the bathroom and sat me down on the toilet seat. She grabbed her bag and worked away at my face, pointing pencils here and brushes there, ordering eyes closes and mouths pouted.

She then reached for another bag, and pulled out her hair straightener and set to work with my hair. My blonde locks are long for a guy’s, so it wasn’t hard for her to work it into a woman’s style.

She looked me up and down.

“Something is not right.”

“Really?” I said sarcastically. “Where do I start?”

“Ha ha. No, I know what it is. Can I please shave your legs?”

“No way! I’ll look ridiculous.”

“No you won’t. Besides, summer is months away and if you bring a girl home say you swim or cycle or something.”

It wasn’t likely I’d be bringing a girl home any time soon. Bugger it.

“Alright then.”

“Wow, you really are game tonight!”

She lathered up my legs and set to work. She went up passed my knees and up my thighs, lifting the dress as she went. Her hands on my inner thigh got me aroused, lifting the dress higher.

“You’re really enjoying this, aren’t xslot Güncel Giriş you?”

“Hey, how am I not meant to get excited with you up my dress!”

She then got my to lift my arms, and removed the tufts from my arm pits. Once done there she stood up, stepped back and admired her handiwork.

“A few more things.”

She darted back to her room, returning with a couple more items of clothing, and a pair of heeled black ankle boots.

“Put these on,” she said, handing me black panties and a pair of tights.

I didn’t argue, I’d gone so far already, what more is a pair of panties and tights. I slipped on the panties and lifted the tights up my legs. She passed me the shoes and slipped my feet in. They were tight, but Monica and I were remarkably similar in size.

“You look gorgeous.”

“Really,” I again said sarcastically.

“No, really. Look.”

She lifted a mirror to my face.


Looking back at me was a beautiful girl, with dark eyes, rich red lips framed with shoulder-length blonde hair.

“I look …”

“Hot. Sexy even. And I’m qualified to say that,” she laughed. “Come to my room and look at yourself in my full-length mirror.”

I followed her to her room and stood in front of the mirror. I had thought I’d look like a man in drag, but no, I was gorgeous.

“You’re really gorgeous,” Monica said, quietly in my ear.

“I know.” I gulped.

“I hope you don’t take this wrong way, but you’re a better looking girl than a guy. Like, you could get anyone you wanted looking like this.”

“Um, thanks, but I’m not gay.”

“Are you sure? You’re the one dressed like a woman.”

“Haha, very funny.”

“Come on, let’s go watch TV.”

“Um, I’m going to get changed first.”

“Why? You’re so pretty. Come on, stay dressed up for a while. We can hang out as girls this evening.”

“But I’m not a girl,” I protested.

“I wish you were,” she said. “Come on.”

I followed her onto the couch, and we both slouched down with our feet balanced up on the coffee table. What had she meant by ‘I wish you were a girl’? Is she turned on by me looking like this? Yeah, she’s gay – but I’m a guy.

Monica flicked through the channels, settling for a cheesy chick-flick.

“Perfect movie for a girls’ night in.”

I said nothing, still trying to get my head around the situation. Why was I dressed like a woman? And what did Monica mean earlier? I had to admit, I was surprised by how good I looked. And I was secretly enjoying the feeling of the tights on my legs, the bra strap digging lightly into my skin, the slight stickiness of the lipstick. I know it wasn’t right, but it felt so right.

Monica leaned her head on mine, and slid her hand into mine.

“I wish you were a girl,” she said once more. She leaned in and kissed me on the lips.

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