The Roommate Ch. 02

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Monica makes me the girl of my dreams.
1.9k words
4.52
49.8k
28

Part 2 of the 4 part series

Updated 06/07/2023
Created 10/31/2015
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Cordellia
Cordellia
59 Followers

I woke up on the couch in the middle of the night, about 1am. My head ached. My back was even worse. On the coffee table lay a tipped wine glass, stained red, alongside four empty bottles of pinot noir.

My chest felt tight. I reached up and felt the strap of a bra. What?

The activities of the night before came flashing back. The dressing up. The make-up. The kiss. Oh shit, the kiss.

I must've passed out on the couch. Monica was kind enough to take off my shoes (or rather her shoes) place a blanket over me and turn off the light, before she went to bed.

I got up, and stumbled to the bathroom. In the mirror I saw a beautiful girl who looked like she'd had a rough night, hair knotted and make-up smudged across her face. I grabbed some of Monica's wipes and removed the evidence of last night's entertainment.

I went to my room, slipped out of the dress, removed the bra, and collapsed onto my bed.

I was woken several hours later by a knock on the door.

"Wake up sleepy head! It's midday and I've made you some breakfast."

"Ugh, thanks."

"Are you decent? Can I come in?"

I climbed under the duvet and pulled it up to my shoulders.

"Yip, come in."

The door opened and Monica entered my room, holding a tray. As always, she looked amazing. Monica wore an oversized t-shirt which just covered her bum. Her hair tied up in a loose ponytail. Effortlessly gorgeous, I thought. She placed the tray down on my lap and sat down on my bed next to me.

"Thanks, you shouldn't have," I said looking at the plate of crisp bacon and fried eggs on toast, next to a cup of dark coffee.

"So, you look different this morning," she laughed.

"Ha, what happened last night?"

"Really, you were that drunk?"

"I dunno. All I know is I woke feeling awful and looking even worse."

"Come on, you couldn't have been that drunk. And trust me, you looked good."

"Um, yeah, sure."

"No, really you did. I hope we can hang out like that again."

"I don't know about that."

"Oh come on! You looked like you were having such a good time. And it's fun to hang out just as two girls."

I took a sip of the coffee and began cutting a bite of food.

"Hey, be honest with me, was last night the first time you'd dressed up? You didn't put up much of a fight - I'd almost think you secretly wanted to wear my clothes."

I slowly chewed my mouthful of bacon and eggs, swallowing with a gulp.

"Well um, I guess I had before. Girlfriends in the past have got me to put on one of their dresses and sometimes even done my hair and make-up. In a weird way I always kinda enjoyed it - but I wouldn't admit it or dare indulge my interest in it, because I'd feel so, ya know, emasculated. Real guys don't do that sort of thing, you know?

"Well if you want to dress with me around the house, you should, if that's what you'd like. No one else will ever know."

"Alright, maybe. I don't know. Thanks anyway."

Another week rolled around. I hated my job, stacking groceries at the supermarket. It was only a temporary thing, I hoped, as I looked for something better. Monica, on the otherhand, had landed on her feet and found a job at a legal firm.

By Friday I was shattered, and had planned to stay in for the night. Monica had other ideas.

"Let's go out for a drink," she suggested.

"I'm knackered. And I'm broke."

"Come on, it will be fun."

"Alright, maybe. Let's just have a few drinks here first."

A few drinks became eight drinks, and before long Monica and I were giggling like schoolgirls.

"Hey, how about we play dress up again?" she suggested.

"Really?"

"Yeah, it'll be fun."

"Alright then. To be honest I was hoping you'd suggest it!"

"Ha, you're so keen! Alright then. Anything in particular you want to wear?"

"Let's see your wardrobe."

I sat down on Monica's bed as she pulled dress after dress from the wardrobe and held them out for me to see. Monica had an impressive selection of dresses and skirts. She had flowing dresses to dance in and formal skirts for work, summer dresses to show off her slender legs and tight dresses to flaunt her figure. And of course her black dress. But another dress immediately took my fancy.

"That one," I said as she held up a navy dress with tiny polka dots.

"Really? Actually I think it will suit you. I haven't worn this in years. In fact you can have it."

"Really? Um, thanks."

"Well then, take off your clothes!"

"Um, ok. Always nice to have an attractive woman say that!"

"Sorry buddy, but I've got no interest in what you've got underneath your clothes!"

"Ouch, that hurt!"

I took off my shirt, then my jeans and socks, before hesitating at my boxers.

"You won't need those, I'll find you some panties."

I stood naked in the centre of her room as she rummaged through her drawer. She returned with a pair of black panties and a matching bra. She looked me up and down.

"You know, you've got a nice body. For a guy."

"Um, thanks, I guess."

"You'd make a nicer girl though," she said, handing me the underwear.

We went through the same routine as last week. Monica did my make-up, and shaved my legs and arms. Tonight I wore dark red lipstick and Monica gave me the longest imaginable eyelashes. My hair she tied up in a pony tail. Monica passed me the same pair of heels I'd awkwardly worn before.

"You need to practice walking in these," she said.

"Why?"

"Otherwise people will be able to tell you're not a woman."

"Um who are these people? No one else is seeing me like this!"

"Come on, you said you might like to go out for a drink later. Well, now is later! So let's go to town!"

"No way! What if someone recognised me? This was supposed to be just something between you and I."

"No one will recognise you. You look incredible. Besides, I want to go out and I have no other friends in this city yet. Come on, let's have a girl's night out!"

I felt bad for her. She'd been in the city a few weeks and hadn't gone out, on account of hardly knowing anyone. I guess she was right too, no one would ever recognise me.

"Alright then."

"Really?"

"Yeah, it will be fun."

"Wow, you change your tune quickly! Are you sure?"

"Yip, why not?"

"Alright then, I'll just get ready and call a cab."

What was I doing? This was crazy! Why was I doing this? I knew why. I did look good. I felt even better. And I couldn't stop thinking of Monica kissing me last week. What was I doing?

Monica returned from her room with two handbags.

"You'll need this" she said, handing me one. "I've put some make-up in there so you can touch yourself up this evening. There's a purse inside where you can put your bank cards."

"What if I get IDed?"

"Sweetie, you look over 18. And clubs want girls as hot as you inside."

I checked myself out in the mirror. What was I doing? I'd kill to be able to date a girl as hot as me. But instead, I am my dream date. Seriously, what was I doing?!

"Before we go, we need to come up with a name for you."

"Sure, like what?"

"Well if you were a girl, what name would you like?"

"I don't know, I'd never thought of it before. What sort of name do I look like?"

"How about Jasmine - like the princess?"

"Ha, great film! I like it."

A beep came from outside and the taxi was here. We locked the door and climbed in the back of the car. There was no turning back. 'Jasmine' was hitting the town!

Once in the central city, Monica told the driver to take us to Bar 22.

"I've heard it's the hottest bar in the city," she said. It was the last sort of place I'd usually go.

The line snaked from the door around the corner, but Monica instead went straight to the doorman. He pulled up the rope and waved us in, much to the displeasure of the scores of men queuing.

"Wow," I whispered to her as we entered. "How did you do that?"

"Like I said earlier, clubs like this want hotties like you in here. Otherwise it'll be a sausage fest."

We went to the bar, and Monica ordered two cocktails. It was sweet, a tad sickly, but easy enough to drink. We grabbed a booth and sat down.

We sat closely next to each other and talked for what seemed like hours - although we could barely hear each other over the music. After we finished a couple of rounds of drinks Monica stood and grabbed my hand

"Let's dance," Monica shouted in my ear.

I hate dancing. I don't know how to move my body, like most guys I sway from left to right. Monica grabbed my arm and dragged me to the dance floor. The room pulsed with a generic top 40 hit, the bass reverbing though my body. Monica raised her arms, her hips gyrated - she was taken in with the music. I aped her motions, the dress sliding sensually on my skin as I desperately sought to fit - and not fall over in the heels. Monica placed a hand on my waist and led me in time with the rhythm. I looked in her eyes, she smiled, and shouted something. I couldn't hear her over the music, so leant in. My body now rubbed against hers as we moved. She leaned her head in and kissed me. Our lips locked and she pressed her tongue into my mouth. The tip of her tongue meet mine. Her hand had now moved onto my back and down onto my arse. I brought my arms around her and held her tight. The embrace continued. My thoughts drowned out the music - what was I doing? This wasn't right - Monica's gay and I'm not a girl. But it felt so right.

The night wore on. Monica and I danced till my feet stung. I could barely walk. It was time to go.

"You'll have to get your own shoes that fit," Monica said. "We'll go shopping tomorrow."

We hailed a cab, and made out the whole trip home. Monica fumbled the door open, and we collapsed on the couch in each other's arms. Our lips meet again for a moment, before Monica pushed me away.

"I want you so bad," she said.

"Me too."

"But, well, I just don't think we should."

My heart dropped. I had been here before - although of course this time was very different.

"Yeah, I guess you're right," I said, disappointed.

"Just not yet, sweetie. Just not yet."

What did that mean?

"Good night, Jasmine."

She kissed me on the forehead, got up, and went to her room.

Cordellia
Cordellia
59 Followers
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SissyBoy1WarszawaSissyBoy1Warszawaabout 1 month ago

You write beautifully, Cordelia, maintaining the atmosphere, pace of action and emotions. You develop the individual portrayals of Monica's boy's transformation into a girl and naming her Jasmine in a very interesting way. I am in love with Jasmine, I really like her feminization and submission to Monica.

I can already imagine what will happen while Monica and Jasmina are shopping, what will happen when choosing and trying on underwear, dresses, skirts and blouses.

Will the boy/Jasmina completely surrender to Monica?

ps. Sorry for any errors and linguistic inaccuracies, I don't speak English.

SissyBoy from Warsaw, Poland. 👩🏻‍🦳♀️❤️👧🏻⚧️🧒🏻

AnonymousAnonymousabout 7 years ago

Again, well written!

AnonymousAnonymousover 8 years ago
Poor Jaz!

That's a very frustrating end of a hot night in the city! Waiting anxiously for the shopping spree...

satinshawnasatinshawnaover 8 years ago
Wonderful, keep on writing, pretty, pretty please

What a nice and erotic, sensitive story.

DaveXX80DaveXX80over 8 years ago
Another winner

Great second chapter! That is a night I would love to have!

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